Why choose a Mid-Century Modern Specialist as Your Agent?

Ellen Hilburg offers a unique vision of Mid-Century Modern Homes with  an unusual passion for the history, architecture and the designer/architects of the mid-century contemporary homes in the lower Hudson River region of New York.

Ellen will become your “personal shopper,” opting to show you the best listings as they pop up on the market. Remember, not all Mid-Century homes are the treasures you’d hope to expect. Some have been “updated” so much that the original beauty cannot be rediscovered. Others have become orphans of style in the midst of deteriorating or vastly changed locations. Ellen will pass on knowledge not only of period design, but of location, the state of repair/disrepair, and the value of your investment.

PROPERTIES

1306 Grants Lane, Ossining, NY 10562 (MLS # 1023302)

(all data current as of 7/24/2026)
Price $1,700,000
Beds 2
Baths 2 Baths
Home size 1,590 sqft
Lot Size 17.45 ac
Days on Market 10
Status Active
Some homes are simply built. Others are designed to change the way you experience nature. This extraordinary 1956 residence by renowned architect David Henken, one of Frank Lloyd Wright's most celebrated apprentices, is one of those rare homes. Privately nestled on more than 17 breathtaking acres above a babbling stream near Teatown Lake Reservation, the home embodies the timeless principles of organic architecture, where walls of glass, natural materials, and thoughtful siting dissolve the boundaries between indoors and out. Built from Philippine mahogany, stone, slate, and glass, every detail was carefully considered to create harmony with the surrounding landscape. The result is a 2 bedroom 2 bathroom home that feels remarkably current nearly seventy years later. Inside, soaring glass walls frame the changing seasons while a dramatic stone fireplace anchors the main living space. Original built-ins, slate floors, rich mahogany, and a signature wraparound deck celebrate Henken's vision, while the thoughtfully updated kitchen and recent improvements allow the home to function beautifully for modern living. Designed using passive solar principles decades before sustainability became mainstream, the home captures the low winter sun for natural warmth while deep roof overhangs provide cooling shade throughout the summer additionally geothermal heating, solar, and other thoughtful updates bring modern all-electric comfort to the home. Complementing the main residence is a beautifully reimagined 1,200 square foot studio that expands the property's possibilities. Completely renovated, the space now offers a bedroom, full bath, living area, kitchenette, and a stunning spa-inspired sauna suite finished with terrazzo tile, warm Aspen wood, and premium contemporary materials throughout. Whether used as a guest retreat, artist's studio, wellness space, home office, or income-producing guest accommodation, it offers the same thoughtful design and craftsmanship found in the main home. Recent improvements, including a newly constructed carport, estate-style gravel driveway, high-performance siding, Energy Star windows, updated insulation, and new mechanical connections to the studio, ensure the property is ready for years of effortless enjoyment. The setting is every bit as extraordinary as the architecture. Wander your own seventeen-acre landscape, listen to the year-round stream, or spend the afternoon exploring nearby Teatown Lake Reservation. Just beyond, you'll find some of the Hudson Valley's most celebrated destinations, including Blue Hill at Stone Barns and The Farmer & The Fish. Nearby towns of Ridgefield, Pound Ridge, Katonah and Bedford, offer exceptional dining, galleries, farmers markets, and hiking. Metro-North provides easy access to New York City, making this an extraordinary full-time residence or one of the region's most remarkable weekend escapes. Architecturally significant homes of this caliber rarely become available. This is more than a residence"”it's an opportunity to own a living piece of mid-century design history, thoughtfully preserved for the next generation.

Property Type(s): Single Family

Last Updated 7/15/2026 Tract n/a
Year Built 1956 Community n/a
Garage Spaces n/a County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #1023302)

131 Deertrack Lane, Irvington, NY 10533 (MLS # 1025460)

(all data current as of 7/24/2026)
Price $845,000
Beds 4
Baths 2.5 Baths
Home size 2,398 sqft
Lot Size 26,136 sqft
Days on Market 25
Status Active
Tucked away at the end of a private cul-de-sac in one of Irvington's most desirable neighborhoods, this authentic Mid-Century Modern offers a rare opportunity to own a truly special home. Lovingly cared for by the same owner since it was built, this cherished home is being offered for sale for the first time, making it a once-in-a-generation opportunity. Surrounded by other distinctive Mid-Century Modern residences, it sits in one of the most unique and sought-after settings in Westchester. Inside, vaulted ceilings, exposed beams, and expansive walls of glass fill the home with natural light and create a seamless connection to the surrounding landscape, hallmarks of classic Mid-Century Modern design. Rich with original character and timeless architectural details, the home presents the perfect opportunity to update and make it your own while preserving its distinctive style. Whether you're a Mid-Century Modern enthusiast or simply appreciate exceptional design, this is a rare chance to own an architectural gem in Irvington. Just five minutes from Irvington's vibrant Main Street, you'll enjoy easy access to restaurants, boutique shops, parks, and Metro-North. As a bonus, the property offers the best of Irvington living while benefiting from Tarrytown property taxes.

Property Type(s): Single Family

Last Updated 7/16/2026 Tract n/a
Year Built 1962 Community n/a
Garage Spaces 1.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #1025460)

41 Mead Road, Armonk, NY 10504 (MLS # 999973)

(all data current as of 7/24/2026)
Price $4,495,000
Beds 6
Baths 8 Baths
Home size 10,824 sqft
Lot Size 3.98 ac
Days on Market 71
Status Active
Modern Vision for Classic Suburban Living 41 Mead Road is an exceptionally custom-built residence that blends architectural sophistication with serene natural beauty. Sitting on 3.98 acres with a total interior area of 10,824 square feet with expansive open-concept living areas designed for modern luxury living. Offering 6 generously sized bedrooms and 7 full bathrooms with 2 additional half baths, thoughtfully designed for everyday comfort and entertainment. Surrounded by lush greenery, the floor to ceiling windows seamlessly blend indoor and outdoor living showcasing abundant natural light and serene views throughout. Features include plentiful storage throughout, including a well-appointed mudroom designed for effortless everyday functionality and organization. Beautiful office space with a balcony overlooking nature. Additional convertible spaces provide exceptional flexibility for customized lifestyle and entertainment areas, with the potential for a private sauna, cinema, recreation lounge, wellness retreat, or expansive secondary living spaces. A unique opportunity exists to expand the outdoor entertaining space with a potential 3,500-square-foot rooftop deck. Additional highlights include proximity to the Armonk town center and North Castle's nature preserves, hiking trails, and golf courses. Convenient access to White Plains, Greenwich, and NYC makes this home a rare offering in one of Westchester's most sought-after communities. Some Pictures are Virtually Staged

Property Type(s): Single Family

Last Updated 7/15/2026 Tract n/a
Year Built 2026 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Corcoran Legends Realty

(view all details for MLS #999973)

12 Tallwoods Road, Armonk, NY 10504 (MLS # 1009019)

(all data current as of 7/24/2026)
Price $1,860,000
Beds 3
Baths 3 Baths
Home size 2,406 sqft
Lot Size 2.30 ac
Days on Market 12
Status Active
Built in 1962 in the spirit of Usonia, this exceptional mid-century modern residence is being offered for the first time by its original owners. Designed through a unique collaboration with renowned architect Edgar Tafel, Frank Lloyd Wright's longtime apprentice, the home showcases soaring lofted ceilings, a dramatic custom walnut architectural ceiling feature, striking stone accents, and a stunning floor-to-ceiling stone fireplace. Privately set on 2.3 acres on a quiet dead-end road, this architectural gem offers 3 bedrooms, 3 full baths including a primary ensuite, a den, a finished walk-out lower level and expansive decking. An attached two-car garage with a bonus of a separate car barn with additional space for 6 cars, ideal as an artist's studio, workshop, or creative retreat. A rare opportunity to own an architecturally significant home that beautifully honors the principles of mid-century modern design while preserving the vision of its original owners. A truly special offering where architectural history and timeless design come together. Home as art.

Property Type(s): Single Family

Last Updated 7/14/2026 Tract n/a
Year Built 1962 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Houlihan Lawrence Inc.

(view all details for MLS #1009019)

3461 Route 9G, Rhinebeck, NY 12572 (MLS # 1026060)

(all data current as of 7/24/2026)
Price $4,250,000
Beds 7
Baths 5 Baths
Home size 4,496 sqft
Lot Size 10.11 ac
Days on Market 40
Status Active
The Canopy House Named for the towering canopy of mature trees that defines its landscape, The Canopy House is a home shaped as much by light as by architecture. Here, the forest is not simply the backdrop, it becomes part of daily life. Walls of glass frame the changing seasons while sunlight filters through the leaves, casting shifting patterns across stone, wood, and slate throughout the day. Set on 10.11 wooded acres just minutes from the heart of Rhinebeck Village, the property offers a rare balance of privacy and connection. Masterfully reidesigned in 2019 by the acclaimed design-build firm The Art of Building, the main residence is a remarkable expression of craftsmanship and thoughtful design. Mid-century modern architecture is complemented by an understated palette of warm woods, natural stone, dark architectural accents, and expansive glass, creating interiors that feel sophisticated, welcoming, and deeply connected to their surroundings. Throughout the home, there is a quiet appreciation for proportion, natural light, and finely crafted detail, reflecting a philosophy of design where beauty is found in simplicity and every space feels intentional. Designed for effortless single-level living, the home's flowing floor plan balances expansive gathering spaces with private sleeping quarters. The soaring great room is anchored by a dramatic double-sided floor-to-ceiling stone fireplace, while three interconnected living spaces, wrapped in walls of glass, create a seamless connection to the surrounding landscape. The chef's kitchen opens naturally to the adjacent living and dining areas, creating an ideal setting for both intimate evenings and effortless entertaining. The primary suite is a true sanctuary, complete with a soaking tub, walk in shower, and views of the surrounding landscape. Three additional bedrooms are thoughtfully positioned in the main house to provide privacy and exceptional livability. Privately positioned beyond the main residence, the 1,132-square-foot guest house functions as a home unto itself, offering two bedrooms, a full kitchen, generous living spaces, a wood-burning stove, an attached bonus room ideal as a studio, gym, or office, and its own outdoor living area. Outside, a 20-by-50 heated gunite pool is nestled among mature trees and layered plantings, creating a private setting and remote setting. Historic stone walls weave throughout the landscape while generous lawns unfold beneath the canopy, reinforcing a setting that feels both timeless and distinctly Hudson Valley. Located just seven minutes from Rhinebeck Village, twelve minutes from Amtrak, and approximately ten minutes from the future Soho Farmhouse Hudson Valley.

Property Type(s): Single Family

Last Updated 7/14/2026 Tract n/a
Year Built 1975 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Upstate Down

(view all details for MLS #1026060)

24 Lafayette Road, Tappan, NY 10983 (MLS # 1026237)

(all data current as of 7/24/2026)
Price $510,000
Beds 3
Baths 2 Baths
Home size 1,196 sqft
Lot Size 9,584 sqft
Days on Market 11
Status Active
Beautifully updated and lovingly maintained, this 3-bedroom, 2-full-bath ranch offers the convenience of one-level living. This move-in ready home features an open floor plan with a comfortable flow between the living, dining, and kitchen areas. The updated eat-in kitchen offers access to a private, flat backyard, perfect for outdoor enjoyment and entertaining. The primary bedroom includes an ensuite bath, with two additional bedrooms and a second full bath providing plenty of space and flexibility. Thoughtfully updated throughout, this home offers true comfort, functionality, and easy living. Located in the desirable town of Tappan with South Orangetown schools and easy access to hiking trails, parks, shopping, dining, and transportation. A wonderful opportunity to enjoy true turnkey living in a sought-after community!

Property Type(s): Single Family

Last Updated 7/15/2026 Tract n/a
Year Built 1940 Community n/a
Garage Spaces n/a County Rockland
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Realty

(view all details for MLS #1026237)

27 Castle Road, Piermont, NY 10968 (MLS # 1017797)

(all data current as of 7/24/2026)
Price $4,195,000
Beds 4
Baths 4 Baths
Home size 3,800 sqft
Lot Size 3.16 ac
Days on Market 12
Status Active
KoiHaus, a mid-century modern home on 3.16 acres, tucked away on a secluded road near the banks of the Hudson River"”just a stone's throw from the legendary 1890s McKim, Mead & White masterpiece, Lord's Castle. This architectural gem is a masterclass in organic design, orchestrating a brilliant dialogue between mid-century modern aesthetics and the spiritual heritage of Japanese landscaping. KoiHaus is more than just a luxury residence; it is a living sanctuary where home and nature exist as one. The landscape is as important as the architectural design. The landscape architect designed the gardens from inside out - thru its 100 windows. There is harmony between the home's natural setting and the architectural design. The home rises from the site line as one approaches it, going past the 13 ft tall steel elephant in the front yard, that moves naturally by the wind. True to the legacy of Frank Lloyd Wright, KoiHaus utilizes clean lines and geometric shapes, that are softened by its Japanese gardens and landscape. The structure is composed of five interconnected boxes, wrapped in an exterior palette of concrete, stucco, stone, and rich hardwood, all capped by a durable, 50-year roof. What truly defines the exterior, however, is its relationship with light. Its many windows of varying shapes and sizes, framing shifting natural portraits throughout the day. Every detail leans into sleek minimalism. Broad, flat moldings complement natural stone walls, while pocket doors are utilized throughout to maximize room volume and echo Japanese sliding screens. Premium finishes include polished bluestone countertops KoiHaus' defining engineering feature is its split-foundation design. Technically it is two independent structures joined by a dramatic glass-and-steel bridge. Beneath this bridge flows a continuous, sprawling koi pond that meanders under and around the house. From almost any vantage point, residents can look out to watch Nishikigoi"”the "living jewels" of Japan"”swimming gracefully in their natural habitat. In Japanese philosophy, the koi represents perseverance, strength, harmony, and transformation. Spanning approximately 5,800 sqft of meticulously planned living space, the estate balances Grand-Scale entertaining with intimate comfort: 1) Main & Upper Levels (3,700 sqft): Features a massive chef's kitchen with a vast walk-in pantry, a dining room perfectly positioned for sunset views, and bamboo flooring throughout. 2) Walk-Out Lower Level (2,000 sqft): This level is above-grade on two sides, large fitness room with a wall of windows (could function as another den), home theater, wet bar room and full bath. A hot tub is conviently located outside its back doors. 3) The Annex: A 1,000 sqft semi-finished space w/climate control offers endless options. Currently used as a practice room for the band! 6,800sf total. Property Specifications: Total sqft: 5,800 + 1,000sqft in the annex. Bedrooms, 4 (possible 6 to 7). Baths, 4. Outdoor living, 1,500sqft of premium IPE decking. Garage: 2 car with duallifts to accommodate 4 vehicles. Climate Control: full zoone heating and central air conitioning throughout. The structure was designed by the acclaimed bi-coastal architect Brian Spence, AIA (NYC & LA), and the landscape was designed by renowned Japanese garden expert Asher Browne. While KoiHaus feels like a world unto itself, it is remarkably connected. Located near the historic Hudson Riverfront village of Piermont, it offers from five-star dining, local marinas, vibrant farmers markets, and a pristine 700-acre state park. Commuting is effortlessly simple: it is a mere 6 minutes to the Mario Cuomo Bridge (connecting to Metro-North for a straight shot into Grand Central) and just 15 minutes to the George Washington Bridge into Manhattan. For the connoisseur of art, architecture, and mindful living, it becomes instantly clear upon arrival: KoiHaus. Nothing Compares.

Property Type(s): Single Family

Last Updated 7/13/2026 Tract n/a
Year Built 2006 Community n/a
Garage Spaces 4.0 County Rockland
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Ellis Sotheby's Intl Realty

(view all details for MLS #1017797)

353 Mountain Road, Irvington, NY 10533 (MLS # 1022183)

(all data current as of 7/24/2026)
Price $2,995,000
Beds 4
Baths 5.5 Baths
Home size 4,774 sqft
Lot Size 2.31 ac
Days on Market 17
Status Active
Ultra Private Country Estate - Only 40 Minutes From NYC - The Perfect Setting - Peaceful 2.3 Acre Horticultural Oasis - Irvington, NY - Luxurious Mid-Century Modern Home With Pristine Gardens & Grounds - Majestic Shade Trees, Flowering Shrubs, Specimen Plantings & Athletic Field Sized Lawns - Generously Proportioned Rooms, King-Size Outdoor Decks & Abundant Parking Make This Home Ideal For Formal Entertaining or Accommodating Out-Of-Town Guests || GENERAL INFO || ** 5,500 sq ft, 4 bedroom, 5.5 bath home on a lush 2.3 acre oasis ** Sunny & bright 4,700 sq ft main living area ** Plus an additional 800 sq ft two-room office suite w/full bath, wet bar & separate parking area || MAIN LIVING AREA || ** Entry hall with coat closet & powder room ** Grand LR w/floor-ceiling windows, 16' cathedral ceiling, wood burning fplc hdwd flrs & French doors to king size (650 sq ft) ipe wood deck ** Formal dining room ** Huge skylit gourmet kitchen w/designer cabinets, granite countertops & top-of-the-line appliances ** Adjoining breakfast dining area with SGD to x-large (600 sq ft) ipe wood deck ** Skylit library with granite fireplace & built-in bookcases ** Home office with built-in workstation, bookcases & large windows overlooking backyard || BEDROOM WING || ** Hall bath w/tub ** BR #1, BR #2, BR #3 (former MBR) with WIC & luxury bath w/marble counters, twin vanities & spa shower || 2nd FLOOR MASTER BEDROOM SUITE (844 sq ft) || ** Spacious master bedroom with cathedral ceiling & extra large windows overlooking lush backyard ** Two extra-large WICs ** Luxury bath w/marble counters, twin vanities, non-slip floor, jacuzzi & walk-in spa-style shower || LARGE EXERCISE ROOM || ** Hallway w/two cedar closets & full bath ** Extra large (450 sq ft) solarium-fitness room w/vaulted ceiling & 12' wide SGD doors to large bluestone patio ** Heated Endless Pool (7' x 14') ** Independent climate controlled HVAC system || TWO-ROOM PROFESSIONAL OFFICE SUITE (800 sq ft - potential guest, in-law, nanny suite) || ** Private professional office with closet ** Waiting room with private entrance ** Full bath ** Wet bar ** Independent HVAC system ** Separate 6-car parking area || ADDITIONAL FEATURES || ** Meticulously maintained inside & outside ** No-step entry ** Main floor bedrooms ** Attached two car garage with additional 2-car parking apron ** 2 fireplaces ** 2 king-size decks ** Extra-large bluestone patio ** Automated irrigation system ** Three independent HVAC systems ** Propane-fueled generator ** Fire sprinkler systerm ** Additional 6-car gravel parking area ** Spacious walkout storage basement ** Centrally monitored security system ** Town of Greenburgh ** Town park privileges ** Irvington School District ** Short walk to 400 acre Irvington Woods & Irvington Nature Center ** 40 minutes to NYC by train or car ** 10 minutes to Mario Cuomo Bridge ** 20 minutes to downtown White Plains

Property Type(s): Single Family

Last Updated 7/8/2026 Tract n/a
Year Built 1960 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Realty

(view all details for MLS #1022183)

We're sorry, but we couldn't find MLS # 1019928 in our database. This property may be a new listing or possibly taken off the market. Please check back again.

481 Mount Airy Road E, Croton-on-Hudson, NY 10520 (MLS # 996386)

(all data current as of 7/24/2026)
Price $1,675,000
Beds 5
Baths 5.5 Baths
Home size 5,600 sqft
Lot Size 1.22 ac
Days on Market 39
Status Active
A thoughtfully curated contemporary retreat where architectural character meets modern comfort. Enter through an expansive foyer, where a dramatic curved staircase sets the tone for the home's distinctive design that draws you up to a vaulted open-concept living space, featuring light cherry wood floors, original hand-hewn exposed beams, and a striking floor-to-ceiling concrete fireplace that anchors the room with quiet sophistication. European-inspired kitchen is both functional and sculptural, centered around a 12-foot recycled quartz peninsula; minimalist and a striking, artful aesthetic. Moroccan plaster finished floors add warmth and texture, while an adjoining pantry provides exceptional storage and direct access to the side garden. Designed for seamless indoor-outdoor living, the main level opens to a raised flagstone patio overlooking the rear garden and deck. Within this free-flowing layout is a spacious dining area with oversized windows and whitewashed exposed brick walls that further enhance the home's natural light and layered character. The home offers multiple ensuite bedrooms, including a truly private primary suite set in its own wing. This inviting sanctuary features a high-efficiency wood-burning fireplace insert, providing exceptional warmth and energy efficiency.. Expansive east- and west-facing windows with treetop views, and a private wrap around walk-out terrace. The spa-like bath includes radiant heated floors, a free standing soaking tub, and an oversized zero entry shower. A generous walk-in closet and additional storage complete the suite. Two additional bedrooms on this level include one with its own terrace, along with a beautifully renovated full bath. A separate upper-level ensuite bedroom with walk-in closet and full bath provides ideal accommodations for guests or extended family. Off the foyer, a flexible suite of rooms complete with a full bath offers endless possibilities, additional sleep quarters, in-home office, creative studio, with French doors leading to the garden. This home offers a rare balance of warmth, scale, and modern minimalism with seclusion. Featured in Westchester Magazine for its thoughtful architectural details as a curated contemporary retreat. There is winter reservoir views. Express trains from Croton Harmon to GCT 45 minutes.

Property Type(s): Single Family

Last Updated 6/23/2026 Tract n/a
Year Built 1933 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Realty

(view all details for MLS #996386)

44 Woodlands Trail, Clinton Corners, NY 12514 (MLS # 1010034)

(all data current as of 7/24/2026)
Price $2,150,000
Beds 3
Baths 2.5 Baths
Home size 3,060 sqft
Lot Size 5.41 ac
Days on Market 38
Status Active
Modern Design. Sustainable Living. Hudson Valley Serenity. Tucked away on 5.41 private acres in the heart of Clinton Corners, this custom-built contemporary retreat seamlessly blends modern architecture, energy efficiency, and a deep connection to nature. Thoughtfully designed for today's lifestyle, the home offers more than 3,000 square feet of light-filled living space surrounded by mature trees, curated landscaping, and peaceful Hudson Valley scenery. The home's striking Western Red Cedar exterior, standing seam metal roof, and clean architectural lines create an immediate sense of arrival. Inside, polished radiant-heated concrete floors, soaring vaulted ceilings, and expansive windows establish a warm yet sophisticated atmosphere. Natural light pours into every room while carefully framed views connect the interior to the surrounding landscape. At the heart of the home is an open-concept kitchen, dining, and living area designed for both everyday living and entertaining. The chef's kitchen features custom cabinetry, quartz countertops, stainless steel appliances, and a large center island, while the living room is anchored by a propane fireplace and walls of glass overlooking the property. One of the home's most memorable spaces is the screened porch, where a dramatic stone wood-burning fireplace creates the perfect three-season retreat to relax, entertain, or enjoy the changing seasons. Outside, the Trex deck and Bullfrog Spa provide the ideal setting to unwind and take in the natural surroundings. The home offers three bedrooms, a dedicated home office, and a separate home gym, creating flexibility for remote work, wellness, and modern living. The primary suite serves as a private retreat with a spa-inspired bath featuring a freestanding soaking tub, oversized walk-in shower, and tranquil views. Designed with sustainability in mind, the property includes radiant heated floors, heat pumps, solar panels, and an EV charging station. More than 40 varieties of trees, raised-bed gardens, open lawn space, and wooded privacy complete the setting. Conveniently located near Rhinebeck, Millbrook, Pine Plains, and the Taconic State Parkway, 44 Woodlands Trail offers a rare opportunity to own a thoughtfully designed modern retreat in one of the Hudson Valley's most desirable locations.

Property Type(s): Single Family

Last Updated 6/17/2026 Tract n/a
Year Built 2018 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Serhant LLC

(view all details for MLS #1010034)

56 Lauren Court, Woodstock, NY 12401 (MLS # 1012176)

(all data current as of 7/24/2026)
Price $2,300,000
Beds 3
Baths 3 Baths
Home size 3,481 sqft
Lot Size 4.39 ac
Days on Market 45
Status Active
Exceptional 3 bedroom, 4 bath light-filled contemporary home offering refined nouvelle living set on over 4 private acres in Woodstock, NY. This home has had a complete interior high-end designer renovation that has been thoughtfully curated with sophisticated finishes and fine craftsmanship blending seamless luxury, comfort, and architectural elegance. A dramatic great room framed by soaring glass windows fills the interior with natural light where sliding glass doors open to expansive outdoor decks, creating an effortless indoor-outdoor lifestyle. The open floor plan, featuring a chef's kitchen -- beautifully appointed with premium Thermador appliances, custom cabinetry, and sleek designer finishes -- and living area are tailored for both entertaining and everyday living. Hand-crafted built-in bookshelves enhance the office, great room, and loft, where the upper-level lounge overlooks the stunning main living space below and to the tall wall of windows. The private primary suite is situated on the top floor with a spa-inspired bathroom featuring radiant heated floors, a deep soaking tub, shower and Toto toilet...Two additional bedrooms are on the mid-level which features a full bath, soaking tub, shower, Toto toilet and radiant heat, this floor also includes an additional half bath. The full finished walk-out basement is set-up for an entertainment room, gym, artist studio or or bedroom, the basement also has another half bath. This residence offers 2,613 square feet of living space plus the additional 868-square-foot fully finished basement. Details include mini-splits in all living spaces, propane forced air and baseboard heat, refinished heart-pine flooring, propane fireplace in the great room, a two-car garage with electric and a framed out future living space above, a whole-house on demand generator, new windows, alarm system, freshly painted exterior, and a beautifully updated saline pool with new heater and a pool house. An extraordinary turnkey property offering privacy, style, and luxury in a serene natural setting, perfect for year-round living or a woodsy retreat just minutes to Village of Woodstock and central to the City of Kingston. A 3D Walkthrough Tour is available in the digital Lookbook or by request.

Property Type(s): Single Family

Last Updated 6/11/2026 Tract n/a
Year Built 2002 Community n/a
Garage Spaces 2.0 County Ulster
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Village Green

(view all details for MLS #1012176)

17 Eastwoods Road, Pound Ridge, NY 10576 (MLS # 1001204)

(all data current as of 7/24/2026)
Price $2,650,000
Beds 5
Baths 5.5 Baths
Home size 5,662 sqft
Lot Size 3.35 ac
Days on Market 47
Status Active
Fabulous Country Retreat. Absolute serenity! Long drive through scenic woodlands to peaceful privacy. Fabulous high site with glorious sunset views. Beautifully landscaped grounds with an array of fine and flowering plantings, fenced for deer. Free-form Swimming Pool with spa and two waterfalls. Perfectly positioned Tennis Court. Architect-designed Country House with contemporary and traditional elements. Stunning interior spaces with beautifully scaled rooms, vaulted ceilings and walls of windows. Exceptional craftsmanship with substantial millwork, wide board oak floors and high-end finishes. Nearly 5700 square feet of finely appointed living space. Fabulous open floorplan with impressive main rooms for entertaining. Chef's Kitchen with center island, custom cabinetry, marble counters and high-end appliances. Five Bedrooms include a spectacular Primary Suite with Dressing Room, Office, Gym and Two Baths. Lower level Recreation Room. The ultimate estate for the most discerning buyer.

Property Type(s): Single Family

Last Updated 6/9/2026 Tract n/a
Year Built 1978 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Ginnel Real Estate

(view all details for MLS #1001204)

164 Eastwoods Road, Pound Ridge, NY 10576 (MLS # 1007263)

(all data current as of 7/24/2026)
Price $15,000,000
Beds 5
Baths 5 Baths
Home size 5,500 sqft
Lot Size 38.63 ac
Days on Market 51
Status Active
EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

Property Type(s): Single Family

Last Updated 6/4/2026 Tract n/a
Year Built 1976 Community n/a
Garage Spaces 4.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Ginnel Real Estate

(view all details for MLS #1007263)

2 Stonecreek Road, Woodstock, NY 12498 (MLS # 1004041)

(all data current as of 7/24/2026)
Price $4,000,000
Beds 4
Baths 3.5 Baths
Home size 2,750 sqft
Lot Size 8.31 ac
Days on Market 60
Status Active
Stonecreek is a one-of-a-kind newly constructed turnkey furnished designer residence conceived and designed with Dichotomy Interiors, brought to life through a collaboration rooted in design, craftsmanship, and a deep connection to the surrounding landscape, set on 8.3 private acres within 101 acres of protected conservation land just five minutes from Tinker Street in Woodstock. This fully realized four-bedroom, three-and-a-half-bath contemporary retreat offers approximately 2,800 square feet of thoughtfully curated interior living space, complemented by over 2,000 square feet of outdoor entertaining terraces surrounding the heated gunite pool and landscaped grounds. Included in the offering are all brand new designer furnishings, decor, rugs, lighting, cookware, serveware, bedding, towels, window treatments, and outdoor furnishings - creating an exceptionally rare move-in-ready luxury experience in the Hudson Valley. Expansive Weathershield windows, a dramatic 4.5-foot glass pivot entry door, and oversized sliding glass doors frame the surrounding landscape while filling the home with natural southern light throughout the day. At the center of the residence, a soaring 16-foot oak ceiling in the great room is anchored by a suspended wood-burning fireplace. The kitchen features White Oak millwork by Rex Hill Studios, thick Taj Mahal quartzite countertops, a 12-foot island, matching quartzite backsplash and sculptural hood, a six-burner Wolf range, integrated wine refrigeration, and a fully equipped secondary butler's kitchen with additional refrigeration, sink, dishwasher, and speed oven. White Oak millwork carries throughout the home alongside French White Oak flooring, hand-troweled eco-friendly lime plaster walls, artisan wall coverings by ;litis France, bespoke lighting, custom drapery, remote-operated window treatments, and fully outfitted closets by Scarlett Rising Designs. Bathrooms and laundry spaces feature bespoke vanities, Taj Mahal quartzite and Noisette Fleury marble surfaces, floor-to-ceiling stone walls, radiant heated stone flooring, and wall-mounted Toto toilets. The primary suite offers a spa-like retreat with a terrazzo freestanding soaking tub set on bush-hammered limestone flooring overlooking the surrounding landscape, a nine-foot vanity, expansive walk-in closet, and layered natural materials designed to create a calming connection to the outdoors. A curated collection of contemporary fine art by notable New York and Hudson Valley artists selected specifically for the residence to complement the architecture and interiors is also available separately for purchase. Outdoor living is equally considered, with over 2,000 square feet of porcelain-paved patio space, an 18x35 heated gunite pool with automatic cover, architectural and landscape lighting, irrigation, steel planters, specimen tree plantings, original stone walls, deer-proof fencing, and a wood-burning fire pit designed for year-round entertaining. Additional features include low-maintenance eco-conscious NewTechWood siding made from recycled materials, seamless metal roofing and gutters, ducted HVAC, tankless water heaters with recirculated hot water, Smart WiFi Lutron lighting, six Ring security cameras, a generator with dedicated propane tank, EV charging station, separate laundry room with sink off the mudroom, a 2.5-car carport with attached storage shed, and a private road setting moments from the center of Woodstock. A rare opportunity to acquire a fully realized designer residence offering privacy, architectural integrity, & true turnkey living in one of the Hudson Valley's most sought-after settings.

Property Type(s): Single Family

Last Updated 5/26/2026 Tract n/a
Year Built 2026 Community n/a
Garage Spaces n/a County Ulster
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #1004041)

365 Tower Hill Road, Wassaic, NY 12592 (MLS # 1002180)

(all data current as of 7/24/2026)
Price $16,500,000
Beds 4
Baths 6.5 Baths
Home size 7,500 sqft
Lot Size 138.42 ac
Days on Market 65
Status Active
Introducing Sky House. This 7,500-square-foot modern estate atop 138 acres of meadows, woodland, and rolling hills in Millbrook's storied hunt country is a study in serenity and design intelligence. Conceived by the celebrated firm Resolution: 4 Architecture and completed in 2019, the residence rises from the landscape with a long, linear silhouette tempered by floor-to-ceiling glass that invites the outdoors into its interior vocabulary. Here, architecture does not compete with nature; it offers a refined frame through which the Hudson Valley unfolds. A long private drive reveals the home as a subtle, sculptural form set against a panorama of the valley. The approach is intentionally understated; a cinematic progression culminating in the soaring glass foyer at the center of the home. The first floor unfolds as a sequence of generous, light-filled spaces, beginning with a great room defined by a dramatic blackened-steel fireplace surround and a monumental 20-foot retractable wall of glass that allows the room to open completely to the landscape beyond. Outside, an expansive covered terrace unfolds beneath a contemporary pergola, where shifting light and shadow animate the space throughout the day. Conceived as a true outdoor living room, the terrace offers multiple seating areas oriented toward panoramic views of the surrounding fields and distant mountains. Beyond lies a media room with its own fireplace, a handsome retreat for film, music, or winter nights. Just beyond, the office appears as a hushed sanctuary bathed in soft natural light. With views stretching across the landscape, it offers a beautiful connection to the world outside. The home features a chef's kitchen with contemporary millwork, discreet storage, and professional-grade appliances. Adjacent are a pantry, mudroom, powder room, and back-of-house spaces designed to support both intimate daily living and large-scale entertaining. A staircase of clean lines and floating geometry leads to the second level, though an elevator links all floors with ease. At the top, a spectacular outdoor terrace extends the living space into the sky. With lounge seating arranged around a sleek outdoor fireplace, it becomes a natural stage for twilight cocktails, summer dinners, and stargazing. The primary suite occupies its own wing, conceived as a restorative retreat. The bedroom, wrapped in glass and soft morning light, is complemented by dual dressing rooms, a massage and treatment room with fireplace, and a spa-inspired bath anchored by a sculptural soaking tub positioned toward the horizon. Separate indoor and outdoor showers offer a choice between privacy and open-air immersion. Three additional en suite bedrooms provide comfort and independence for guests, each with its own view and sense of calm. The outdoor amenities are equally sophisticated. A pool house with kitchen and lounge stands beside an infinity-edge pool and spa that appear to slip toward the valley below. A three-car garage, designed with the same architectural restraint as the main residence, adds practicality without compromising aesthetic integrity. Beyond the immediate grounds stretch acres of meadows, forested trails, and open fields suited for riding or walking. Though utterly private, the property is minutes from Millbrook's charming village center, local farmstands, dining, and regional hiking and riding trails. Yet its true allure lies in the equilibrium it creates between monumental design and whisper-soft landscape, between contemporary precision and the timeless calm of country life. More than a residence, Sky House is a living composition of light, terrain, and modern craft; a place for contemplative mornings, lively weekends, and the rare sensation of inhabiting a home that is simultaneously shelter, sculpture, and sanctuary.

Property Type(s): Single Family

Last Updated 5/21/2026 Tract n/a
Year Built 2019 Community n/a
Garage Spaces 3.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #1002180)

115 N Smith Road, Lagrangeville, NY 12540 (MLS # 999874)

(all data current as of 7/24/2026)
Price $999,000
Beds 3
Baths 2 Baths
Home size 1,976 sqft
Lot Size 9.82 ac
Days on Market 72
Status Active
Looking for something unique? Perched atop a scenic knoll overlooking Sky Acres Airport, this extraordinary earth-sheltered home offers a rare blend of eco-friendly living, modern luxury, and breathtaking panoramic views. Designed to maximize southern and western sun exposure, the home is earth-bermed on the north, east, and roof, featuring nearly two feet of earth insulation and a 27-inch overhang for exceptional energy efficiency "” keeping annual oil usage remarkably low at just 200-300 gallons per year while maintaining comfortable year-round temperatures between 50-78 degrees. Completely renovated throughout, the home showcases a stunning gourmet kitchen with soft-close cabinetry, granite countertops, and LG stainless steel appliances. The beautifully updated primary and guest bathrooms combine comfort and style with high-end finishes. Offering 2-3 bedrooms plus a dedicated office, the home is filled with warmth and character, including exposed natural wood beams and a striking Russian fireplace that elegantly separates the living and dining areas. Spectacular views of Sky Acres Airport along with sweeping 40-mile vistas stretching south and east to the Shawangunk Mountains. New Anderson windows throughout flood the home with natural light, while a sliding glass door off the living room opens to a spacious brick patio "” the perfect place to relax and watch planes take off and land against the stunning countryside backdrop. Aviation Enthusiasts Welcome! Additional features include a 2-car garage and a 2 story 24 x 24 barn with loft space, all situated on 9.8 private acres. Comes completely furnished, potential airbnb. Enjoy the ultimate aviation lifestyle with the airport just a short stroll away "” offering the freedom to fly virtually anywhere right from your home.

Property Type(s): Single Family

Last Updated 6/6/2026 Tract n/a
Year Built 1981 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with BHHS Hudson Valley Properties

(view all details for MLS #999874)

476 Carpenter Hill Road, Pine Plains, NY 12567 (MLS # 885787)

(all data current as of 7/24/2026)
Price $2,995,000
Beds 4
Baths 4 Baths
Home size 4,103 sqft
Lot Size 19.07 ac
Days on Market 376
Status Active
Modern Minimalist Masterpiece on 19 Bucolic Acres in Dutchess County. Welcome to a rare offering in the heart of the Hudson Valley, where striking modern architecture meets timeless pastoral beauty. Completed in late 2024, this extraordinary estate sits on over 19 acres of flat, fenced farmland at the picturesque intersection of Bethel Cross and Carpenter Hill Road. Perfectly sited on a south-facing rise along the Shekomeko Creek, this newly constructed home is a serene, sophisticated sanctuary just two hours from New York City. A bold fusion of modern, industrial, and eclectic design, the residence offers over 4,700 square feet of light-filled, open-concept living on one level, including 3,057+/- sq ft main house, a stunning 1,046+/- sq ft attached greenhouse-conservatory that brings year-round indoor-outdoor living to life and a 1,423 sq ft +/- heated garage/studio/guest apartment. Every detail was curated with intention; from yaki sugi siding and a metal Kemper roof to polished concrete floors and walls of glass that frame unspoiled views of nature. The heart of the home features a bespoke chef's kitchen with live-edge shelving, custom cabinetry milled from trees on the property, concrete countertops, a butler's pantry, and a beverage bar. Double primary suites offer en suite wood burning stoves, spa-like baths with cast iron tubs, Italian tile, and handcrafted metal vanities. Both are complimented by airy bathrooms with natural light and industrial fixtures.A gas fireplace in the ample living room, vaulted ceilings, clerestory windows, and art lighting throughout create a harmonious blend of warmth and style. This is a home designed not just to live in, but to live fully. Outside, the entire 19-acre estate is bordered by classic white 4-board oak fencing, ensuring both privacy and visual continuity. A one-acre, 10-foot-deep pond and expansive flat pastures make this a dream property for equestrians, polo enthusiasts, hobby farmers, or anyone seeking a deep connection with the land. Zoned as a horse farm within an agricultural district, it offers rare potential for animal lovers and breeders alike. Car collectors and creatives will appreciate the oversized, fully heated garage and studio space outfitted with track lighting, storage, and the flexibility to serve as an art gallery, workshop, or one-bedroom apartment. With a 3,000 sq ft unfinished basement, covered porches, multiple patios, and estate management partners already in place, the property is as functional as it is inspiring. Additional features include an Endless Pools heated performance pool in greenhouse. The home has a sustainable, passive solar design and was constructed to allow for a future living roof/rooftop deck. New well, septic, and underground utilities. Energy-efficient systems throughout. Surrounded by horse farms and wildlife. Just minutes from the town center and Mashomack Polo Club. Whether you're an artist, gardener, equestrian, or collector, this unique Hudson Valley estate delivers a modern lifestyle without compromise. Offered for the discerning buyer seeking privacy, sophistication, and natural beauty in equal measure.

Property Type(s): Single Family

Last Updated 5/6/2026 Tract n/a
Year Built 2023 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with William Raveis Lifestyles Rlty

(view all details for MLS #885787)

33 Ford Road, Chatham, NY 12136 (MLS # 991875)

(all data current as of 7/24/2026)
Price $3,995,000
Beds 6
Baths 4.5 Baths
Home size 5,019 sqft
Lot Size 10.00 ac
Days on Market 85
Status Active
CEDAR HILL - Architectural Country Living at its Finest - is the embodiment of 21st-century modern luxury. Elevated on 10 private acres with sweeping mountain views, a gracious mix of open and wooded landscape, a serene spring-fed lily pond, and an organic vegetable garden, this newly expanded and reimagined six-bedroom home is set in Old Chatham, one of the most coveted corners of New York's historic Hudson Valley. The home engages seamlessly with its natural surroundings through walls of glass that draw in the changing seasons - from spring's first blooms and summer's golden light to autumn's rich palette and the quiet beauty of snow-covered peaks. Abundant natural light and warm finishes create interiors that balance architectural precision with a sense of comfort and ease. The grounds include a 50-foot heated in-ground Gunite salt-water pool and spa, surrounded by expansive bluestone patios. Thoughtfully positioned just beyond, a cedar-clad spa pavilion - with sauna and custom sleek stainless hot tub - is connected to the house by a breezeway, creates a natural extension of the home while preserving a sense of privacy. Southern light fills this entire setting throughout the day, enhancing both the interiors and outdoor living spaces. A deco-turf night-lit tennis court built by a premier tennis contractor in the Berkshires complete the private, resort-like atmosphere, ideal for restorative retreats, entertaining, or quiet relaxation. The formal living room, with soaring 22-foot ceilings, anchored by a wood-burning fireplace flows effortlessly into a gracious dining area, an open kitchen and butler's pantry and a secondary gathering room with its own wood-burning fireplace. A game and media room opens directly to the pool terrace, while the main level also offers a first-floor bedroom, full plus half- bath, along with a beautifully designed mudroom with breezeway access. Upstairs, the primary suite serves as a private sanctuary, with glass doors opening to a deck that captures mountain vistas with south and west exposures. Four additional bedrooms, bathroom, a flexible-use room with grand terrace, and a second laundry provide ample space for guests, work and wellness. The property, rebuilt and expanded over a multi-year renovation, was completed in 2023. Designed for year-round, sustainable modern living. Solar power, radiant heated interiors, a three-car heated garage, and multiple EV charging stations ensure comfort and efficiency in every season. Underground utilities further enhance the natural setting. Surrounded by the natural beauty of the Hudson Valley and the Berkshires, Cedar Hill offers access to hiking, skiing, farm-to-table dining, and cultural destinations - while remaining a peaceful retreat to relax and recharge.

Property Type(s): Single Family

Last Updated 6/27/2026 Tract n/a
Year Built 1992 Community n/a
Garage Spaces 3.0 County Columbia
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Brown Harris Stevens HV LLC

(view all details for MLS #991875)

213 Vail Lane, North Salem, NY 10560 (MLS # 986322)

(all data current as of 7/24/2026)
Price $1,149,000
Beds 4
Baths 2.5 Baths
Home size 2,896 sqft
Lot Size 3.27 ac
Days on Market 115
Status Active
Tucked away on a quiet lane in North Salem, this one-of-a-kind contemporary home offers a rare blend of privacy, design, and natural beauty. Set amidst a breathtaking perennial garden with meandering paths, the property invites you into a serene, zen-like retreat complete with a tranquil pool and hot tub. Inside the approximately 2,900 square foot residence showcases an open, airy floor plan highlighted by abundant natural light, numerous skylights, and two fireplaces that anchor the living and dining spaces. The kitchen flows seamlessly onto an inviting deck-perfect for morning coffee or effortless outdoor entertaining. The home features four bedrooms and two-and-a-half baths, including thoughtfully designed details such as Japanese toilets. An upper-level space provides flexibility for a home office or yoga room, adding to the home's versatility. The grounds are equally captivating, with cleared areas ideal for vegetable gardening-where abundant harvests have thrived. The architecture evokes a timeless, Frank Lloyd Wright inspired aesthetic, harmonizing beautifully with the surrounding landscape. Located just 55 miles north of New York City, this property offers convenient access to trains and major highways, making it ideal for both full-time living and weekend escapes. North Salem's renowned equestrian culture and expansive open spaces further enhance the appeal of this exceptional offering. A truly special and well maintained hidden gem - this home is where nature, design, and lifestyle come together in perfect balance.

Property Type(s): Single Family

Last Updated 6/3/2026 Tract n/a
Year Built 1982 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Realty

(view all details for MLS #986322)

39 Old Snake Hill Road, Pound Ridge, NY 10576 (MLS # 823299)

(all data current as of 7/24/2026)
Price $3,995,000
Beds 5
Baths 5.5 Baths
Home size 4,718 sqft
Lot Size 5.78 ac
Days on Market 93
Status Active
Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake "” a setting that feels worlds away, yet sits just one hour from Manhattan. Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams "” a rare marriage of architectural integrity and contemporary refinement. The result is a home that feels both timeless and entirely of the moment. The main residence offers four bedrooms and has sweeping water views that define the property. A detached guest studio with two-car garage provides flexible accommodation for visitors or staff, while the heated gunite pool and pool house "” complete with full bath, wet bar, and huge fireplace "” create an effortless setting for both quiet evenings and elevated entertaining. An additional detached two car garage rounds out the offering. Outside, the grounds have been as thoughtfully curated as the interiors: new landscaping, artisan stonework, full irrigation system, patios, and mature tree work frame the lake and connect seamlessly to the Pound Ridge Land Conservancy "” a permanent buffer that ensures the privacy and natural beauty of this property endure. Truly turnkey. Completely one-of-a-kind.

Property Type(s): Single Family

Last Updated 7/1/2026 Tract n/a
Year Built 1967 Community n/a
Garage Spaces 4.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Houlihan Lawrence Inc.

(view all details for MLS #823299)

258 Hardscrabble Road, North Salem, NY 10560 (MLS # 959925)

(all data current as of 7/24/2026)
Price $1,895,000
Beds 4
Baths 3 Baths
Home size 2,300 sqft
Lot Size 6.01 ac
Days on Market 162
Status Active
Tamoset. A truly magical setting overlooking a scenic pond. Long drive to peaceful privacy. Six spectacular acres with rolling lawns, old stone walls, ornamental trees and perennial gardens. Sophisticated Country House originally built in the 1930's. Spectacular renovation with airy loft-like spaces. Sun-filled rooms with vaulted ceilings, random-width pine floors and custom lighting. Walls of windows capture natural light and scenic views. Dramatic Great Room with floor-to-ceiling stone fireplace. Dining Area with doors to two decks with a fabulous water view. Gourmet Kitchen with custom backlit cabinetry, granite and stainless countertops and professional appliances. First floor Primary Suite with door to private terraced garden. Two additional Bedrooms, one with loft sleeping area. Guest Room with Bath and doors to Screened Porch and two sun decks. Lower Level with pine-paneled Family Room, Sauna, and Wine Cellar. Covered porch with automatic screens, cold plunge tub, and hot tub. Covered Lap Pool with swim jet and automatic phantom screens. Detached Outbuilding with Gym. Fabulous location just moments from the apple orchards. Truly remarkable!

Property Type(s): Single Family

Last Updated 6/23/2026 Tract n/a
Year Built 1930 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Ginnel Real Estate

(view all details for MLS #959925)

2 Lakeridge Drive, Armonk, NY 10504 (MLS # 971207)

(all data current as of 7/24/2026)
Price $3,225,000
Beds 4
Baths 4 Baths
Home size 4,925 sqft
Lot Size 4.56 ac
Days on Market 114
Status Active
Modern Luxury Meets Lakeside Serenity. Experience a rare blend of privacy and year-round recreation in this custom-built Armonk home set directly on the water's edge. Designed for effortless living, it offers kayaking, swimming, and peaceful mornings from your private dock. Outdoors, a lakeside fire pit, outdoor shower, and secluded hot tub are framed by panoramic water views. The home is thoughtfully designed to blur the line between indoors and out. Floor-to-ceiling windows and bi-fold glass doors open to expansive decking and striking dry-stack stonework, creating seamless flow. Inside, wide-plank flooring and a dramatic two-story great room with a floor-to-ceiling stone fireplace establish a warm, refined atmosphere. The space connects to a chef's kitchen with premium appliances, walk-in pantry, and wine refrigerator. The primary suite is a private retreat with its own fireplace, deck access, and spa-like bath. Upstairs, three bedrooms surround a flexible lounge ideal for a media room or play space. The finished entry level includes a home gym, theater, and large mudroom. Minutes from town yet completely private, this exceptional property offers a true modern lakefront lifestyle.

Property Type(s): Single Family

Last Updated 6/15/2026 Tract n/a
Year Built 2016 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Houlihan Lawrence Inc.

(view all details for MLS #971207)

890 Bald Mountain Road, Austerlitz, NY 12017 (MLS # 948729)

(all data current as of 7/24/2026)
Price $4,950,000
Beds 6
Baths 4.5 Baths
Home size 6,309 sqft
Lot Size 85.51 ac
Days on Market 200
Status Active
Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes, on 84 acres, has been listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, glass, wood and stone panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past the homes, beyond the two crystal clear ponds are the jaw-dropping 360 degree views and another possible building site. Overlooking 3 states, situated between The Hudson Valley and The Berkshires, the possibilities are endless!

Property Type(s): Single Family

Last Updated 5/27/2026 Tract n/a
Year Built 2007 Community n/a
Garage Spaces 2.0 County Columbia
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with The Kinderhook Group, Inc.

(view all details for MLS #948729)

111 Philipse Brook Road, Garrison, NY 10524 (MLS # 962616)

(all data current as of 7/24/2026)
Price $1,300,000
Beds 4
Baths 2.5 Baths
Home size 2,294 sqft
Lot Size 5.20 ac
Days on Market 144
Status Active
A rare opportunity to own over 5.9 acres across three separate parcels in the heart of Garrison. The main residence at 111 Philipse Brook Road is a 4-bedroom, 2.5-bath Colonial built in 1987, offering approximately 2,294 square feet of living space on 1.83 acres. The home features a gracious layout with spacious living and dining areas, wood-beamed ceilings, two fireplaces, a finished lower-level recreation room, open and screened porches, and an attached two-car garage. Included in this offering are two additional separately deeded parcels: 2.25-acre lot 1.83-acre lot All three parcels together provide flexibility for estate expansion, compound living, long-term investment, or preservation of privacy. The combined acreage offers a rare opportunity to control surrounding land in this highly desirable Garrison location. Located within the Garrison School District and just minutes to Metro-North, hiking trails, the Hudson River, and the cultural attractions of Cold Spring and Beacon. A unique offering with exceptional potential "” available as a package with all three parcels included in the sale.

Property Type(s): Single Family

Last Updated 3/3/2026 Tract n/a
Year Built 1987 Community n/a
Garage Spaces 2.0 County Putnam
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Julia B Fee Sothebys Int. Rlty

(view all details for MLS #962616)

48 Raafenberg Road, Sleepy Hollow, NY 10591 (MLS # H6335041)

(all data current as of 7/24/2026)
Price $12,000,000
Beds 5
Baths 5.5 Baths
Home size 7,538 sqft
Lot Size 42.17 ac
Days on Market 474
Status Active
Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central core is a great room with 20 foot ceilings and walls of glass facing the river. Equestrian facilities include a 14-stall stable, indoor and outdoor riding arenas, six fenced paddocks and two grooms's apartments. A manager's house, greenhouse, carriage barn and equipment garage are all well located to support the stable, main house and property. Direct trail access from the property is provided through north and south gates to the 55-mile carriage trail network of the 1,800 acre Rockefeller State Park. Winterburn Farm is an extremely rare opportunity offering a pristine architectural house amid a beautiful landscape of unparalleled privacy.

Property Type(s): Single Family

Last Updated 4/7/2025 Tract n/a
Year Built 1973 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #H6335041)

7 Ferris Lane, Poughkeepsie, NY 12601 (MLS # 918376)

(all data current as of 7/24/2026)
Price $825,000
Beds 5
Baths 3 Baths
Home size 4,100 sqft
Lot Size 19,602 sqft
Days on Market 299
Status Active
Situated on Poughkeepsie's prestigious south side, find this rare opportunity of a single family home w/supplemental office space zoned for home occupation. Incredibly unique mid century modern features attractive open floor plan ideal for entertaining. Huge center island kitchen w/custom maple & cherry cabinetry, granite counters & stainless appliances. Kitchen flows seamlessly to family room and first floor office. Massive dining room/living room combo featuring wood burning fireplace & wall of glass incorporating sliding doors to rear patio. Second floor includes master bedroom w/custom closet & updated ensuite bathroom. Four additional bedrooms all with access to expansive balcony overlooking backyard. Loaded with attractive finishes such as brick floors, hardwood floors, recessed lighting and fresh paint throughout. Lower level professional office space includes reception area, restroom and several examination rooms or offices. Ideal for attorney, accountant, spa, music production or artist studio. Fully fenced & private backyard with storage shed & 2 patios. Enjoy the conveniences of municipal water, sewer & natural gas for heat, hot water & cooking. Situated on a double lot and centrally located just minutes from colleges, hospitals, Vassar Farm Ecological preserve, Poughkeepsie waterfront & train station. A truly unique opportunity not to be missed.

Property Type(s): Single Family

Last Updated 9/29/2025 Tract n/a
Year Built 1960 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with BHHS Hudson Valley Properties

(view all details for MLS #918376)

105 Sand Hill Road, Dover Plains, NY 12522 (MLS # 932753)

(all data current as of 7/24/2026)
Price $450,000
Beds 1
Baths 1 Bath
Home size 805 sqft
Lot Size 7.18 ac
Days on Market 261
Status Active
The Geosphere is a convergence of visionary design, tactical investment and natural sanctuary. Set on 7.18 secluded acres in the heart of Dover Plains, this fully legal, architect-designed geodesic residence and studio building give you something unmistakably distinctive: a home that feels like art, and a property that can perform like an asset. Inside, the striking residence is fully winterized, featuring commanding glass and skylights, a custom-crafted interior and a cozy wood stove that makes efficiency luxurious. The main geodesic dome is complemented by a studio seamlessly integrated into the landscape "” perfect for an art studio, office, or workspace. The infrastructure is robust: on-grid power with off-grid capability, a dedicated well and full septic system. A spring-fed natural swimming pond, aerated and stocked with fish, doubles as a functional fire-safety reservoir (an insurance-advantage you rarely see). A new half-mile gravel driveway ensures privacy and serenity from the main road. Zoned and fully permitted as a short-term rental through Dutchess County, The Geosphere Retreat is income-ready if that is what you seek. Comparable homes in the region are generating $1,000-$2,000 per week. With further subdivision potential (2-acre minimum lots), and agricultural tax incentives available, this isn't just a home "” it's a platform for both current income potential"”and future upside. Positioned in Dover, NY, two hours from New York City, in an area where growth is quietly gathering pace, including nearby Silo Ridge, and One&Only in development, complete with commuter-link access via Metro-North's Harlem Line. The Geosphere awaits to deliver a statement, a sanctuary, and a truly unique value proposition.

Property Type(s): Single Family

Last Updated 4/22/2026 Tract n/a
Year Built 2025 Community n/a
Garage Spaces n/a County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Hudson Modern Co

(view all details for MLS #932753)

"Arc House" Bulls Head Road, Clinton Corners, NY 12514 (MLS # 955667)

(all data current as of 7/24/2026)
Price $2,385,000
Beds 4
Baths 3.5 Baths
Home size 3,127 sqft
Lot Size 13.84 ac
Days on Market 150
Status Active
Arc House, conceived by Palette Architecture, is a refined exploration of balance - where modern form meets the quiet beauty of nature. Designed as a to-be-built retreat for the post-urban lifestyle, this home blends architectural precision with a warm, elemental materiality, offering a deeply restorative escape just moments from the Taconic Parkway and the cultural heart of the Hudson Valley. Set atop a gentle rise and enveloped by forest, the home's distinctive upwardly curved roofline introduces a graceful sense of movement, lifting the structure toward the canopy while echoing the contours of the surrounding landscape. A natural cedar wood siding box sits atop a stone base to ground the architecture in the site, allowing the home to age beautifully and harmonize with its environment. From a distance, its profile feels both intentional and unobtrusive"”modern, yet timeless. The 4-bedroom, 3.5-bath residence spans approximately 3,100 square feet and is carefully sited to ensure privacy and immersion in nature. Upon arrival, interiors unfold with quiet drama: expansive European windows frame rolling wooded ridgelines, flooding the home with natural light and dissolving boundaries between indoors and out. Social spaces appear to float above the terrain, creating an elevated vantage point from which to experience the seasons in constant motion. A dedicated work-from-home office offers a thoughtful separation between professional focus and domestic calm. Throughout the home, a restrained palette of natural materials, warm woods, marble, and hand-crafted tile cultivates a sense of clarity and ease. Outdoor living areas extend seamlessly from the interior, offering a series of curated environments - sun-drenched decks, shaded retreats, and intimate gathering spaces - each designed to foster connection with the land. An optional in-ground pool package further enhances the retreat experience, transforming the property into a private resort for summer living and entertaining. Additional options such as supplemental solar, a fire pit, and other bespoke enhancements allow owners to tailor the home to their lifestyle. Highlights include high-efficiency panelized construction, natural wood and stone cladding, triple-pane European windows and sliding doors, expansive decks with cable railings, wide-plank oak and stone/tile flooring, custom cabinetry, Miele appliances, a wood-burning fireplace, and integrated recessed lighting. Located near Rhinebeck, Red Hook, and Millbrook, "Arc House" represents a thoughtful convergence of design, nature, and modern comfort - an elevated yet grounding place to call home.

Property Type(s): Single Family

Last Updated 2/25/2026 Tract n/a
Year Built 2026 Community n/a
Garage Spaces 2.0 County Dutchess
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with BHHS Hudson Valley Properties

(view all details for MLS #955667)

3031 Purchase Street, Purchase, NY 10577 (MLS # 962804)

(all data current as of 7/24/2026)
Price $9,950,000
Beds 5
Baths 5.5 Baths
Home size 7,447 sqft
Lot Size 3.51 ac
Days on Market 148
Status Active
A Contemporary Estate Shaped by Light and Wood on 3.5 Serene Acres An exquisite modern compound designed for expansive living, this residence is distinguished by its rare collection of purpose-built structures and amenities: a custom-designed Japanese tea house, separate party barn, dedicated pottery/art studio, European KLAFS sauna suite, in-ground pool, and serene Zen-inspired grounds "” all set across 3.5 private acres. Leading custom team including renowned builder Jim Pousada (Crescent Construction) and architect Justin Minieri the 7,447 sq ft black barn-inspired structure is defined by large industrial Marvin custom windows and a disciplined, modern profile. The architecture is organized around a carefully conceived U-shaped floor plan that embraces a central open-concept living space overlooking a contemplative garden. Soaring double-height ceilings "” reaching approximately 20 feet "” define the primary living volumes. Rare 20 inch wide-plank oak flooring on main floor, exposed timber beams, and expansive steel-framed glass reflect a quiet wabi-sabi sensibility. The kitchen, appointed with stone countertops and integrated Gaggenau appliances, centers around a generous eat-in island and features custom Leicht cabinetry and display shelving "” a true chef's kitchen. Living and dining areas open to a covered slate terrace complete with infrared heating and wood-burning fireplace. A glass and wood open-riser staircase provides a sculptural connection between levels. The primary suite occupies a private wing with direct garden access, a luxurious light-filled spa bath with freestanding tub, two custom walk-in closets, and a European KLAFS sauna with Moroccan-inspired shower and European IKONNI slat wall accents. On the opposite side, a dedicated pottery and art studio, complete with a glass mechanical garage door and architectural windows, provides creative flexibility. A four-car attached garage, mudroom with custom cabinetry, and spacious laundry with Leicht cabinetry complete the main level. Select high end fixtures include Rocky Mountain hardware, Brizo faucets and accessories, Julien sinks and Toto Neorest toilet. Three additional light-filled bedrooms with walk-in closets are located on the upper level "” two en-suite and one with an interconnecting bath adjoining a large play or lounge area overlooking the garden. Anchoring the garden is the tea house, wrapped in Accoya Saguaro wood (delta black color) and crowned by a dramatic IKONNI slat wall ceiling, with custom tatami mat and minimalist detailing that reinterpret traditional Japanese design principles through a modern lens. The separate party barn includes its own kitchen and entertaining space opening to an organic garden. The home is showcased in a major motion feature that is being released in September 2026, reflecting its architectural presence and distinctive design. A true modern compound, 3031 Purchase Street offers estate-scale living within close proximity to Manhattan, premier clubs, Westchester airport including private terminal and top schools offering an opportunity for unrivaled elevated living.

Property Type(s): Single Family

Last Updated 6/24/2026 Tract n/a
Year Built 2022 Community n/a
Garage Spaces 4.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Julia B Fee Sothebys Int. Rlty

(view all details for MLS #962804)

95 N Broadway, Irvington, NY 10533 (MLS # 961739)

(all data current as of 7/24/2026)
Price $3,450,000
Beds 5
Baths 5.5 Baths
Home size 4,696 sqft
Lot Size 13,504 sqft
Days on Market 161
Status Active
An Architectural Statement of Light & Glass in Irvington Village - A rare fusion of steel, stone, and warm wood, this custom-designed residence serves as a private sanctuary in the heart of Irvington. Perfectly positioned just 0.2 miles from Metro-North and moments from the Hudson River, this 5-bedroom, 5.5-bath estate redefines luxury village living on 0.31 serene acres. A dramatic double-height foyer makes a bold first impression, featuring a sculptural floating oak staircase and front-to-back sightlines through massive walls of glass. The chef's kitchen is a masterclass in design, anchored by an Arabescato stone island, custom cabinetry, and professional Wolf and Sub-Zero appliances. A "Glass House" experience with radiant-heated floors that lead to La Cantina folding doors, which erase the boundary between the interior and a private entertaining terrace. The primary bedoom retreat offers a treehouse-like atmosphere with a private fireplace, custom dressing room, and a spa-level marble bath featuring a steam shower and freestanding soaking tub. Experience the pinnacle of Westchester modernism.

Property Type(s): Single Family

Last Updated 5/27/2026 Tract n/a
Year Built 2020 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Julia B Fee Sothebys Int. Rlty

(view all details for MLS #961739)

890 Bald Mountain Road, Austerlitz, NY 12017 (MLS # 948729)

(all data current as of 7/24/2026)
Price $4,950,000
Beds 6
Baths 4.5 Baths
Home size 6,309 sqft
Lot Size 85.51 ac
Days on Market 200
Status Active
Located in a private gated community of large acreage land holders, this exquisite enclave of 3 homes, on 84 acres, has been listed in Interior Design magazine. The main house is a stunning post and beam contemporary home, combining steel, glass, wood and stone panels. It overlooks the gunite pool, surrounded by stone walls and the two additional designed and inviting cottages. Continuing past the homes, beyond the two crystal clear ponds are the jaw-dropping 360 degree views and another possible building site. Overlooking 3 states, situated between The Hudson Valley and The Berkshires, the possibilities are endless!

Property Type(s): Single Family

Last Updated 5/27/2026 Tract n/a
Year Built 2007 Community n/a
Garage Spaces 2.0 County Columbia
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with The Kinderhook Group, Inc.

(view all details for MLS #948729)

94-3 Somerstown Road, Ossining, NY 10562 (MLS # 933442)

(all data current as of 7/24/2026)
Price $1,899,000
Beds 4
Baths 3.5 Baths
Home size 2,693 sqft
Lot Size 1.51 ac
Days on Market 258
Status Active
Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is a brand-new community of to-be-built, high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated and private-ranging between 1 1/2 and 3 acres. Masia, is the first of three luxury residences to be offered. Set on two acres and encompassing four bedrooms and three and 1/2 baths, the house is designed all on one level. Rendered in open plan, the kitchen, dining and living rooms are surrounded by floor to ceiling windows and three outdoor exposures-all centered on a free standing, wood burning fireplace. 9 1/2 to 10 1/2 foot ceilings with high clerestory windows and skylights flood the interior with natural light. High quality finishes include wood clad Andersen windows, Restoration hardware bathroom vanities, Herman Miller lighting, five-panel solid fir interior doors, and five-inch white oak floors. A dedicated laundry room, walk-in kitchen pantry, two-car garage and roof top deck are additional amenities. Designed and being built by local Westchester developers, Atelier Atlantic, the new community is conceived as modern homes for the new century. Principals Jennifer and Pascal Smith Couti, who live and work in the Ossining, are leveraging their extensive experience as home designers to bring the project to life and to skillfully integrate the residences into a cohesive and elegant new community. The project is an extraordinary opportunity to fulfill the dream of purchasing a newly-built modern home on a wonderful parcel of beautiful land.

Property Type(s): Single Family

Last Updated 11/11/2025 Tract n/a
Year Built 2026 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #933442)

44 Benedict Hill Road, New Canaan, CT 06840 (MLS # 24126532)

(all data current as of 7/24/2026)
Price $2,750,000
Beds 5
Baths 3.5 Baths
Home size 1,600 sqft
Lot Size 4.60 ac
Days on Market 313
Status Active
Welcome to the iconic Evans House - a striking work of mid-century modern architecture. Designed in 1961 by renowned architect James Evans, this one-of-a-kind residence showcases a striking hyperbolic paraboloid roof that allows for a completely open main level filled with soaring floor-to-ceiling windows. Every room is immersed in natural light and surrounded by serene wooded views, offering unmatched privacy and a sense of retreat. The main level features an effortless open flow with a primary suite, living room, dining room with a see-through fireplace, office/study, powder room, and expansive sliding doors that connect seamlessly to the wraparound deck. The fully finished, walk-out lower level offers four additional bedrooms, two full bathrooms, a dedicated laundry room, and storage. This rare architectural gem is not just a home, but an experience in design, nature, and modern living.

Property Type(s): Single Family

Last Updated 9/15/2025 Tract n/a
Year Built 1960 Community n/a
Garage Spaces n/a County Fairfield
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listing courtesy of Harbor Bridge Realty

(view all details for MLS #24126532)

4800 Congress Street, Fairfield, CT 06824 (MLS # 24104335)

(all data current as of 7/24/2026)
Price $15,000,000
Beds 7
Baths 8.5 Baths
Home size 9,129 sqft
Lot Size 38.91 ac
Days on Market 395
Status Active
The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

Property Type(s): Single Family

Last Updated 6/25/2025 Tract n/a
Year Built 1965 Community n/a
Garage Spaces 6.0 County Fairfield
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listing courtesy of William Pitt Sotheby's Int'l

(view all details for MLS #24104335)

4800 Congress Street, Fairfield, CT 06824 (MLS # 24104335)

(all data current as of 7/24/2026)
Price $15,000,000
Beds 7
Baths 8.5 Baths
Home size 9,129 sqft
Lot Size 38.91 ac
Days on Market 395
Status Active
The Ultimate East Coast Sanctuary, Where Privacy Meets Pinnacle Luxury. Surrounded by high stone walls, a fortress of modern architecture is invisible from the street and engineered for the world's most discerning buyers who demand seclusion with proximity to NYC. This 38.91-acre compound is a one-of-a-kind Fairfield County estate. The former home of Richard Rodgers, composer of The Sound of Music, the mid-century main residence has been masterfully reimagined to incorporate 7 private bedroom suites, all with views over the landscaped property. The bespoke renovation was executed with uncompromising attention to detail and a true no-expense-spared philosophy, incorporating commercial-grade infrastructure, superior materials, and artisan-level craftsmanship throughout, as if cost were no consideration. Lofty ceilings and walls of glass are a perfect setting for an art collector. Separate wings radiate off the main rooms, each space private and thoughtfully composed. A hidden screening room, a stunning Moroccan lounge, and a guest wing allow for A-list entertaining. The barn pool house with full kitchen, bath and pro-grade gym, the pool, and a heated paddle court make this a perfect athlete's compound. Property includes renovated stone guest/caretaker cottage and a private office pavilion. The landscape offers open vistas, an orchard, and allowed equestrian use. Live in ultimate style and privacy surrounded by a 155-acre nature access to NYC, Greenwich, Westport and airports.

Property Type(s): Single Family

Last Updated 6/25/2025 Tract n/a
Year Built 1965 Community n/a
Garage Spaces 6.0 County Fairfield
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listing courtesy of William Pitt Sotheby's Int'l

(view all details for MLS #24104335)

1 Red Rock Road, Wawarsing, NY 12489 (MLS # 873040)

(all data current as of 7/24/2026)
Price $4,364,000
Beds 4
Baths 5 Baths
Home size 3,400 sqft
Lot Size 5.46 ac
Days on Market 418
Status Active
This contemporary mountain home designed by Mapos Architects offers sophisticated living in perfect harmony with its natural surroundings. Thoughtfully divided into three distinct sections to preserve the landscape's integrity, this 3,400 square foot residence provides both luxury and connection to nature. The main living area features warm cedar cladding and a distinctive green roof deck that extends the natural landscape. Floor-to-ceiling triple-pane sliding glass doors open completely to transform the space into a seamless indoor-outdoor environment, perfect for entertaining or peaceful relaxation. The bedroom wing extends dramatically outward from the slope, creating a floating effect above the landscape. The primary suite includes a private, deck with unobstructed mountain views, while three additional bedrooms, each offer their own bath and tranquil setting. A separate guest wing, constructed of poured concrete that echoes the surrounding stone terrain, provides privacy for visitors and includes its own elevated roof deck with panoramic vistas. Built with premium sustainable materials and meticulous attention to detail, Slide Mountain House represents exceptional mountain living with modern comforts. This property balances architectural significance with practical luxury"”an investment in both lifestyle and legacy in one of the Catskills' most desirable locations.

Property Type(s): Single Family

Last Updated 6/4/2025 Tract n/a
Year Built 2026 Community n/a
Garage Spaces 2.0 County Ulster
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Village Green

(view all details for MLS #873040)

4 Red Rock Road, Wawarsing, NY 12489 (MLS # 873106)

(all data current as of 7/24/2026)
Price $3,926,000
Beds 3
Baths 3.5 Baths
Home size 3,060 sqft
Lot Size 3.87 ac
Days on Market 418
Status Active
This exceptional mountain property showcases innovative architectural design that respects and enhances its natural setting. This 3,100 square foot home offers sophisticated living spaces with direct connection to the surrounding landscape. The main living area runs parallel to the natural slope, partially integrated into the terrain for energy efficiency and protection. Floor-to-ceiling triple-pane sliding glass doors open completely to create a seamless transition between indoor comfort and outdoor living, with panoramic mountain views from every angle. The primary suite occupies a premium position extending outward from the main structure, providing exceptional privacy and commanding views. Its private deck creates an elevated vantage point above the tree canopy toward distant mountain peaks. With three bedrooms, three and a half baths, and a versatile den that can function as a fourth bedroom, the home accommodates guests with ease. The thoughtful floor plan balances communal spaces with private retreats. Premium materials throughout include warm cedar cladding and architectural concrete elements that complement the natural surroundings while providing exceptional durability and minimal maintenance. Kaaterskill House represents a rare opportunity to own a significant architectural property that delivers both everyday livability and a meaningful connection to the mountain landscape. Modern luxury meets natural beauty in this thoughtfully designed mountain retreat.

Property Type(s): Single Family

Last Updated 6/4/2025 Tract n/a
Year Built 2026 Community n/a
Garage Spaces 2.0 County Ulster
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Coldwell Banker Village Green

(view all details for MLS #873106)

48 Raafenberg Road, Sleepy Hollow, NY 10591 (MLS # H6335041)

(all data current as of 7/24/2026)
Price $12,000,000
Beds 5
Baths 5.5 Baths
Home size 7,538 sqft
Lot Size 42.17 ac
Days on Market 474
Status Active
Historic Winterburn Farm is a spectacular 42 acre estate compound with sweeping views of the Hudson and Palisades beyond. Located in Westchester's bucolic hamlet of Pocantico Hills, the property offers the beauty and serenity of the country within 30 miles of Manhattan. The main residence, designed for Rodman Rockefeller by Architect Richard P. Donahue, is mid century modern. The home's central core is a great room with 20 foot ceilings and walls of glass facing the river. Equestrian facilities include a 14-stall stable, indoor and outdoor riding arenas, six fenced paddocks and two grooms's apartments. A manager's house, greenhouse, carriage barn and equipment garage are all well located to support the stable, main house and property. Direct trail access from the property is provided through north and south gates to the 55-mile carriage trail network of the 1,800 acre Rockefeller State Park. Winterburn Farm is an extremely rare opportunity offering a pristine architectural house amid a beautiful landscape of unparalleled privacy.

Property Type(s): Single Family

Last Updated 4/7/2025 Tract n/a
Year Built 1973 Community n/a
Garage Spaces 2.0 County Westchester
Total Parking n/a

Listing information deemed reliable but not guaranteed. Read full disclaimer.

Listed with Compass Greater NY, LLC

(view all details for MLS #H6335041)

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The data relating to real estate for sale or lease on this web site comes in part from HGMLS. Real estate listings held by brokerage firms other than the publisher of this website are marked with the HGMLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker. The information appearing herein has not been verified by the Hudson Gateway Multiple Listing Service, Inc. or the Hudson Gateway Association of Realtors, Inc. or by any individual(s) who may be affiliated with said entities, all of whom hereby collectively and severally disclaim any and all responsibility for the accuracy of the information appearing at this web site, at any time or from time to time. All such information should be independently verified by the recipient of such data. This data is not warranted for any purpose. Copyright 2015 Hudson Gateway Multiple Listing Service, Inc. All rights reserved.

Updated: 8th May, 2017