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$1,700,000
2 Beds ⋅ 2 Baths ⋅ 1023302 MLS
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.

1306 Grants Lane, Ossining
$975,000
3 Beds ⋅ 3 Baths ⋅ 1022746 MLS
This charming renovated farmhouse offers 3,000 sq ft of living space and is nestled at the very end of a quiet cul-de-sac providing exceptional privacy and adjacent to protected parklands with scenic walking trails, and the Hudson River. The home features a newly added first floor primary suite complete with a tray ceiling, recessed lighting, oversized walk-in closet, and an adjoining home office all on its own HVAC system, creating the perfect private retreat. The custom kitchen offers granite countertops, custom cabinetry, GE appliances, and a sunny breakfast alcove. The kitchen flows seamlessly into the formal dining room and inviting living room with a wood-burning fireplace and access to the charming covered front porch. The separate and spacious family room on the south side of the home is filled with natural light from a wall of windows with access through sliding glass doors to the patio and fully fenced rear yard. Upstairs you will find two generously sized bedrooms and a versatile bonus room, ideal as a fourth bedroom, home office, laundry room or den. Additional features include a large detached two-car garage with expansive storage, newly installed generator, alarm system with video cameras, multiple laundry hook-ups including a second washer & dryer in the basement. There is also a cover front porch, and two patio areas around the property. Located just 1.5 miles from the Ossining train station! The location is truly exceptional. Situated at the entrance to the Crawbuckie Nature Preserve, this home offers immediate access to appx 20 acres of woodlands with walking trails winding through mature forest along the Hudson River. Enjoy scenic overlooks, observation platforms, and year-round hiking and nature just steps from your front door. This unique combination of character, modern updates, and an unparalleled natural setting makes this home a rare opportunity.

44 Beach Road, Ossining
$929,000
3 Beds ⋅ 2 Baths ⋅ 1011357 MLS
Why wait for vacation when you can enjoy a retreat-like lifestyle every day? This exceptional, fully renovated Colonial with farmhouse charm is a rare Sears Roebuck Kit House circa 1927, seamlessly blending historic character with modern comforts. Thoughtfully updated throughout, the home features central air conditioning, remote-controlled blinds, renovated baths, and hardwood floors that enhance its timeless appeal. At the heart of the home is a beautifully designed custom kitchen featuring a stunning Viking range, soapstone countertops, and a large maple butcher block island. Whether preparing meals, entertaining guests, or gathering with family, this inviting space is as functional as it is beautiful. The spacious great room offers warmth and character with a wood-burning fireplace, creating a cozy setting for crisp autumn evenings and winter nights. Designed for both relaxation and entertaining, the expansive deck spans the length of the home and overlooks the picturesque barn and tranquil pond, creating a private outdoor oasis with a peaceful, country-inspired feel. The primary suite features custom built-in closets and an en-suite bath with a walk-in shower. Two additional bedrooms and a renovated hall bath complete the second level. The finished third-floor attic provides flexible space ideal for a home office, fitness studio, playroom, or creative retreat. The unfinished stone basement offers abundant storage, a laundry area, and direct access to the attached garage via a convenient walkway. Nestled on one of the area's most scenic and sought-after streets, this special property offers the perfect balance of privacy and accessibility, just minutes from the Taconic State Parkway, Metro-North, shopping, dining, and everyday conveniences. A truly unique opportunity to own a piece of history while enjoying all the comforts of modern living.

28 Inningwood Road, Ossining
$995,000
1008929 MLS
Site plan approved subdivision on historic Somerstown road in Ossining. Three lots each with a beautiful building site being all sold together. Roughed in driveway will become common drive to three homesites. Great opportunity to build.

94 Somerstown Road, Ossining
$750,000
3 Beds ⋅ 2 Baths ⋅ 1008226 MLS
Welcome to the peace and tranquility of Morningside Drive. Nestled in a highly desirable location, this well-maintained home offers expansive frontage, ensuring exceptional privacy and a serene setting on almost 1 acre. The spacious primary suite features a private bath and walk-in closet, while beautiful hardwood floors run throughout the home. The inviting living room, anchored by a stunning stone fireplace, creates the perfect gathering space for holidays and special occasions. Sliding glass doors open to a deck overlooking the quiet, picturesque property, providing the ideal place to relax and enjoy nature. Recent updates include a new oil tank (2026), furnace (2024), Corian kitchen countertops offering peace of mind for years to come. The fully finished lower level adds extra space not included in the Sq Ft, totaling 2400sq ft of versatile living space, ideal for a recreation room, home office, gym, or potential in-law or au pair suite. Conveniently located near parks, shopping, dining, and major highways, this home combines privacy with accessibility. Car enthusiasts and entertainers alike will appreciate the oversized two-car attached garage and abundant parking. Enjoy the convenience of walking to Ryder Park, featuring three ball fields, a picnic pavilion, basketball courts, tennis and pickleball courts, walking trails, and a playground. A rare opportunity to enjoy spacious living and a peaceful setting in a sought-after neighborhood.

110 Morningside Drive, Ossining
$3,500,000
10 Beds ⋅ 6 Baths ⋅ 999615 MLS
Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing sophistication or convenience, this is the ultimate retreat. From the moment you arrive, the estate feels transported from another era. A winding cobblestone driveway crafted from salvaged historic Bronx street stones loops through rolling lawns, curated gardens, and towering trees before revealing the magnificent manor overlooking its own private 3-acre pond. The original boathouse sits at the water’s edge, while a heated pool, tennis court, Japanese garden, orchard, vegetable and berry gardens, greenhouse, and heated pottery studio create a lifestyle reminiscent of a private European country estate. The nearly 9,000-square-foot residence is rich with warmth, grandeur, and unforgettable architectural detail. The awe-inspiring Great Room is nothing short of spectacular, anchored by a massive stone fireplace, soaring 40-foot oak-beamed ceilings, and dramatic walls of glass opening to sweeping pond views. Every room tells a story, from the stately oak-paneled library and elegant entertaining spaces to intimate sitting rooms, hidden carved staircases, and beautifully preserved plaster walls that showcase the home’s old-world craftsmanship. Designed for luxurious multi-generational living and grand entertaining alike, the estate features 10 bedrooms spread across thoughtfully designed wings, including guest accommodations and private caretaker quarters. The newly renovated primary suite rivals a five-star hotel, complete with its own fireplace, lounge/office with kitchenette, spa-like bath, dressing room, and tranquil views over the grounds. Nearly every fireplace throughout the home is operational, bringing warmth and romance to every season. Three separate tax lots, including an additional lot near the guest house, add a level of rarity and long-term value seldom found in estates of this caliber. Modern upgrades quietly support the property’s timeless elegance, including heated garages, multiple propane generators, upgraded well systems, mixed central air, and extensive utility and storage spaces. Private, historic, and impossibly romantic, this is more than a home. It is a destination, a lifestyle, and a once-in-a-generation opportunity to own one of the Hudson Valley’s most magical estates, all within easy reach of New York City.

335 Croton Dam Road, Ossining
$1,750,000
9 Beds ⋅ 8 Baths ⋅ 1005133 MLS
Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining
$1,085,000
4 Beds ⋅ 3 Baths ⋅ 1002953 MLS
Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping, dining, and everyday essentials. The Croton-Harmon Train Station is even closer, while convenient access to Route 9A and the Taconic State Parkway makes commuting throughout Westchester and beyond easily accessible. Thoughtfully redesigned and extensively reconstructed under architectural plans, the home features spacious light-filled living areas, a dramatic vaulted great room ceiling, and an architect-designed wall of glass that brings natural light and the surrounding landscape into the heart of the home. Multiple Marvin door systems were designed to create seamless indoor-outdoor flow and future deck integration. The home was designed with a similar footprint across both levels, resulting in an exceptionally large lower level that dramatically expands the usable space of the home and offers substantial flexibility for workshop space, storage, recreation, future finishing, home business use, gym space, or other expanded uses rarely found in the area. The kitchen and main living spaces were rebuilt from the foundation up during the 2008 reconstruction and create a true chef’s kitchen experience, featuring radiant heated flooring beneath large-format tile, custom-built cabinetry, an oversized 5’ x 7’ island, a large built-in KitchenAid refrigerator, KitchenAid dishwasher, and a Thermador professional oven. The kitchen was intentionally designed with exceptional spacing and flow for cooking, entertaining, and everyday living, creating an openness rarely found in homes of this style. A large high-ceiling lower level was also added during the reconstruction, offering excellent flexibility as a workshop, workspace, storage area, gym, hobby space, or potential future finished area. The lower level also includes a second laundry setup with an additional washer and dryer. The spacious primary suite addition includes a large ensuite bath with jacuzzi tub, oversized shower, and private water closet. A second primary-style bedroom offers its own ensuite bathroom with shower and direct access to the backyard, creating excellent flexibility for guests, extended family, multigenerational living, or private workspace use. A second primary bathroom was also fully renovated in 2025. The rare 4-car tandem garage configuration, expansive multi-driveway parking setup with space for approximately 20 vehicles, and oversized lower level create exceptional flexibility for car enthusiasts, collectors, hobbyists, workshop use, home business needs, or anyone seeking substantial additional storage and utility space rarely found in northern Westchester. Additional highlights include a central vacuum system with multiple in-wall outlets and kitchen kick-plate crumb sweeper, fireplace-ready buildout with propane option, generator-ready electrical infrastructure, alarm system, updated water systems, and numerous structural and mechanical improvements completed over the years. A unique opportunity to enjoy peaceful acreage, architectural character, exceptional utility space, commuter convenience, and a level of flexibility rarely found in one property.

54 Allapartus Road, Ossining
$2,295,000
4 Beds ⋅ 4 Baths ⋅ 1002298 MLS
Phase Two at Moradia is now offering a fabulous to-be-built new modern on Lot One. 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 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. MIES is the second of three luxury residences to be offered. Set on two acres and encompassing four bedrooms and three and one half bathrooms the house is designed to take advantage of the natural surroundings. Rendered in open plan, the kitchen, dining and living rooms are surrounded by large windows and three outdoor exposures-all centered on a free standing, wood burning fireplace. 9 1/2 to 14 foot ceilings with high clerestory windows and skylights flood the interior with sunlight. A covered deck is adjacent to the living area. 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 closet, kitchen pantry, two-car garage are additional amenities. Designed and 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.

94 Somerstown Road, Ossining
$850,000
2 Beds ⋅ 2 Baths ⋅ 996003 MLS
A Rare 200-Year-Old Log Cabin Sanctuary with Subdivision/Expansion Potential! Step back in time without sacrificing an ounce of modern comfort in this enchanting, hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history, contemporary ease, and incredible future value with a potential buildable lot included. The interior showcases exceptional craftsmanship, featuring original wide-plank wood floors, a majestic stone fireplace, and a genuine Dutch door. The versatile layout includes two bedrooms plus an alcove and 1.5 baths highlighted by a hand-painted sink. A large, vintage-inspired country kitchen serves as the heart of the home, boasting a herringbone-patterned original brick floor, 1940s decor, and modern appliances including a dishwasher and washer-dryer. The exterior is a true nature lover's sanctuary, featuring a cedar shingle roof, a classic porch with Adirondack furniture, and a sophisticated bluestone slate patio. The expansive grounds are home to a picturesque pond and babbling brook that attract magnificent wildlife. While providing total seclusion, this property is remarkably accessible, located just five minutes from the Croton-on-Hudson train station and local supermarkets. Enjoy being minutes away from Hudson River dining, boating, and Teatown Lake Reservation, with an easy commute of less than one hour to New York City and a 50-minute drive to Thunder Ridge skiing. It is located in a Historic area near Old Croton Aqueduct and Senesqua Park. The community offers 17 parks, including a Westchester River Walk, hiking trails, views of the Hudson, and the Haverstraw-Ossining Ferry. Amenities include an indoor town pool, a Farmers Market, and local dining options. Community events include the Hudson River Music Festival and Teatown Annual Hudson River EagleFest.

227 Cedar Lane, Ossining
$1,095,000
5 Beds ⋅ 3 Baths ⋅ 977120 MLS
This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning grounds showcase a harmonious mix of wooded areas, meandering walking trails, expansive lawns, curated gardens, and beautiful stonework, all connected by a thoughtful network of driveways, pathways, and steps. Multiple terraces, patios, and outdoor seating areas are perfectly positioned across the property to capture its remarkable natural surroundings. The thoughtfully designed Main house layout features an expansive family room with wood-burning fireplace perfect for everyday gathering, first-floor bedroom with a full en-suite bath, ideal for guests, along with a dedicated laundry room. The main floor features walls of windows showcasing the sylvan setting and a formal dining room that flows seamlessly into a spacious living room. The eat-in kitchen, complete with a charming breakfast nook, is easily accessible and well-suited for casual dining. This level also includes three additional bedrooms, including one with a private en-suite bath, two bedrooms share a well-appointed hall bath, and a laundry room. The Detached 3 car garage with guest quarters and guest patio with built-in wood grill and woodland views add to this retreat.

27 Allapartus Circle, Ossining
$2,900,000
7 Beds ⋅ 7 Baths ⋅ 942815 MLS
Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country setting less than an hour on the express train from NYC. The main residence features a warm and welcoming checkerbox marble foyer opening to elegant formal rooms, and flowing to a cozy bar and family room overlooking the grounds through walls of windows. A sparkling chef’s kitchen, convenient butler’s pantry, and finely restored period details make the home ideal for both everyday living and entertaining. Upstairs, there is extensive accommodation, including a spacious primary suite with elevated views of the private lake, along with three additional bedrooms and multiple baths. A generous home office and dedicated home theater provide exceptional flexibility for work and leisure. The uppermost floor offers two more expansive bedrooms, or flex space for a creative studio. Beyond the main residence, the estate includes a 5-car garage connected to a stables complex by an elegant breezeway. An additional and completely remodelled 1-bedroom apartment above the stable wing, and a charming separate 2-bedroom stone cottage provide versatility for guests, multigenerational living, or rental/Airbnb income. Landscaped grounds with nature paths, sweeping lawns, and exceptional stonework make this a true retreat. Located in the quaint riverfront community of Ossining, known for its scenic Hudson views, vibrant downtown, and abundant parks and trails, this property offers a rare opportunity to own a thoughtfully preserved and modernized Hudson Valley estate.

83 Somerstown Road, Ossining
$1,899,000
4 Beds ⋅ 4 Baths ⋅ 933442 MLS
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.

94-3 Somerstown Road, Ossining
$825,000
3 Beds ⋅ 3 Baths ⋅ 888472 MLS
Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with possibility for in-law situation. The handsome house has cedar siding and lots of windows. Ground level has a 3 season porch, 2 rooms with kitchen, plus bath, utility room, laundry and potting room. From outside the beautiful stone steps lead to a large covered porch with entrance to a large room with stone fireplace and wood burning stove insert; there is also a large closet. Massive fireplace and center island are the focal points of the kitchen with terracotta tiling and walls of windows and door to a deck. 20'x24' Living room has a third fireplace and French doors to a slate patio and door to a second potting room that leads to a woodland path. Circular staircase leads to the private quarters; primary bedroom with spa bath including sauna and whirlpool tub. Second bedroom, hall bath and huge bonus room with fireplace and reading room/office/nursery. Please wear suitable shoes for walking the property. Amenities worth mentioning; cast iron baseboard radiators, hardwood floors, high ceilings and new oil burner. 7 mins drive to Croton Harmon RR Sta. Cash Purchase Only. Proof of Funds required before appt can be booked,

81 Glendale Road, Ossining

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.