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$3,100,000
3 Beds ⋅ 5 Baths ⋅ 1019351 MLS
No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and superior hardware throughout. The woods in the house are too numerous to list, but some of them are Mahogany, Red Maple, Pecky Cypress, White Oak, Utile (Mahogany type), Amboyna, Birch, Curly Birch, Bubinga, Red Birch, Maple, Maple Burl, and Walnut. All of the baseboards are double or triple layered with different wood species. All of the light fixtures, window dressings, and appliances stay with the home. The gourmet kitchen contains a steam oven, double drawer freezer full-size refrigerator, built in microwave, warming drawer, six burner stove, double oven, ice maker, separate built-in vacuum cleaning system. Additional square footage is on the basement level. This is a wonderful home surrounded by greenery to entertain guests or enjoy your privacy. Please see video link for a virtual tour.

23 Inningwood Road, Ossining
$1,200,000
3 Beds ⋅ 4 Baths ⋅ 1015078 MLS
Wisteria & Wood: A Craftsman Masterpiece in the Heart of Teatown Tucked into nearly an acre of lush, private landscape in Croton-on-Hudson's most coveted enclave, this custom-built Craftsman residence is where architectural intention meets natural serenity. From the moment you arrive — welcomed by a wisteria-draped pergola and a stunning Belgian block driveway and courtyard — it's clear this home was designed with both beauty and purpose in mind. Inside, the open floor plan unfolds with the effortless flow that today's lifestyle demands. Walls of windows flood the rooms with natural light, while rich hardwood floors, recessed lighting, and an abundance of storage on every level create a home that feels both elevated and completely livable. The wood-burning fireplace anchors the living space with warmth and character, and a stunning wall of built-in bookcases adds depth and personality. Just off the living room, a den offers the perfect balance of connection and privacy — ideal as a reading room, media space, or quiet retreat. The chef's kitchen is appointed with top-of-the-line stainless steel appliances and opens seamlessly to both the dining room and living area — a layout made for entertaining and everyday connection alike. Step outside to the back deck and discover a deeply private outdoor retreat, where nature sets the stage for al fresco dining, morning coffee, or simply doing nothing at all. The spacious primary suite offers a true escape with a generous walk-in closet and a spa bath. Two additional bedrooms feature soaring beamed ceilings and large closets, sharing a full hall bath. The entry level delivers exceptional function with a large mudroom with custom coat cubbies, plus a beautifully finished flex space — ideal as a home office, studio, or guest suite — with a brand new ensuite modern bath. Three bedrooms. with the flexibility to live like 4, and three and a half baths. Craftsmanship in every corner. And then there's the setting. Spectacular rock outcroppings and ancient boulders punctuate the grounds with dramatic natural character, while towering mature trees — including a graceful dogwood and a statuesque magnolia — frame the yard in seasonal beauty. Walk to Teatown Lake Reservation for hiking and birding, or be in Croton village, the Hudson River waterfront, and the Metro-North station in just ten minutes — where a 48-minute express carries you directly into New York City. All within the award-winning Croton-Harmon School District. This is not just a home. It is a way of living.

1821 Spring Valley 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
$705,000
4 Beds ⋅ 2 Baths ⋅ 1011605 MLS
Beautifully maintained TWO FAMILY DUPLEX in the cherished, historic Sparta district! Each 1000 sq. foot apartment features two bedrooms, one updated bathroom, living room, kitchen, dining room and large bright 4 season sun sunroom. The full, unfinished basement features two laundry stations, one for each unit plus plenty of storage. Additional features include oak hardwood floors, stucco walls & solid wood trim. The shared backyard features a large hardwood deck for outdoor entertaining. Ample driveway and off-street parking. This home is very well-maintained. Apartments may enjoy some updating, but the bones of this beautiful property are excellent. Enjoy this incredible location featuring a short walk to the Arcadian Shopping, the Scarborough-on-Hudson train station to GCS, and the Hudson River Front. It doesn't get better than this! Taxes don't reflect STAR savings of $1,591 if qualified.

321 Spring Street, Ossining
$439,000
1 Beds ⋅ 2 Baths ⋅ 1015764 MLS
Welcome to 2 David's Lane, where you will find a charming one-bedroom, corner townhouse in Ossining. This home offers a wonderful opportunity to enjoy comfortable, low-maintenance living in a desirable Westchester community. This thoughtfully designed home features a bright and inviting layout with a comfortable living space, a functional kitchen, and a cozy bedroom retreat. The open flow of the main living area creates a welcoming atmosphere, perfect for relaxing at the end of the day or entertaining guests. The kitchen offers convenient functionality with plenty of potential to make the space your own. The spacious bedroom provides a peaceful place to unwind, while the overall layout maximizes comfort and ease of living. Enjoy the benefits of townhouse living with the privacy and convenience of your own home, along with the added appeal of a well-maintained community setting. Whether you’re a first-time buyer, looking to downsize, or seeking a place that offers simplicity without sacrificing location, this home provides the perfect opportunity. Ideally located near Ossining’s vibrant downtown, restaurants, parks, shopping, and Metro-North transportation, this home offers the perfect blend of comfort and convenience. Come see all that this delightful townhouse has to offer!

2 Davids Lane, Ossining
$625,000
3 Beds ⋅ 3 Baths ⋅ 1013828 MLS
A tri-level gem, just minutes from downtown Ossining, this three bedroom home is perfect for those who need more space, but want less maintenance. Park either in the driveway or pull into the garage (with extra storage space). There is additional parking shortly down the street. Entering the home on the first floor, you will find a flexible bonus room, great for storage, an office or more. There are multiple closets here as well. Up one level is the open living and dining room. Centered on a wood-burning fireplace with granite hearth and featuring new floors, this is a wonderful space. There are sliding doors here, out to the rear deck and tree ensconced lawn beyond. The eat-in kitchen is well laid out, with good counter and cabinet space. Off of the kitchen, find the large balcony - a great place to enjoy a cup of tea in the early morning, or something a little stronger at the end of the day. Also on this floor is the hall bathroom and the large laundry closet. Up one more level, we reach the bedrooms. The primary bedroom, with an ensuite bathroom that has a tub and a shower, has a deep walk-in closet. In this room, and every bedroom, natural light shines through oversized windows with views out to trees. The second and third bedrooms share a full hall bath with a tub. In Ossining, there are few options for three bedroom condominiums. The Deerfield community has a beautiful, large pool - a perfect place to sunbathe even if you don't swim. There are also walking trails, easily accessible from this unit. All of this, just a short drive to shopping, restaurants and parks, and easily accessible to commuting by train or highway. What more can you ask for?

83 Deerfield Lane, Ossining
$1,350,000
6 Beds ⋅ 4 Baths ⋅ 1013182 MLS
Built in 1870 and lovingly restored by its current owners, this Queen Anne Victorian at 28 Hamilton Avenue sits in the heart of Historic Ossining. Both yards are planted with apple, cherry, Asian pear, pawpaw, hazelnut, raspberry, blueberry, and strawberry, along with a working vegetable garden — a rare thing to find alongside a home of this character. Approach through a deep front yard bursting with pollinators, wisteria draping the covered porches. The house keeps its greatest surprise for later — the breathtaking views of the Hudson River and the Palisades are revealed as you move deeper inside, unfolding room by room. Cross the double-door vestibule into a gracious foyer with soaring double-height ceilings, rich wainscoting, inlaid parquet floors, and a staircase anchored by an elaborately turned newel post — all presided over by the first of four hand-carved ceramic tile fireplaces. The main level was built for both formal entertaining and comfortable everyday living. Two spacious living rooms, each with its own ceramic tile fireplace, open into a sun-drenched den with a spectacular coffered wood ceiling, three walls of windows, and doors facing each other — one to the front porch, one to the rear. The formal dining room, with its own fireplace and a sweeping Hudson River School-inspired mural, connects to a well-appointed kitchen with an original farmhouse sink, a corner butler's pantry with intact original cabinetry, and discreet service stairs tucked behind. Throughout, the turret windows with their curved glass are a signature of the era, and of this street. Step out the back and the Hudson opens before you — wide, silver, and immediate — framed by a terraced garden and a covered rear porch made for long evenings. This is the river that stirred a generation of painters to invent an American landscape tradition, that carried commerce and dreams in equal measure, that poets and wanderers have stood before and felt genuinely small. It is your backyard now. Upstairs, four bedrooms include a primary suite of nearly 20 by 18 feet, wrapped in a turret bay, with a screened balcony, ensuite bath, and the kind of proportions that are simply not built anymore. The current owners have thoughtfully upgraded the electrical and insulation throughout the attic, creating a series of carefully considered spaces — a serene room for yoga, meditation, or quiet work, a jewel-like sitting room with leaded diamond windows, a full bath, and at the crown of it all, a lookout tower lined with curved bookshelves and wide-plank floors, from which this house has contemplated the mighty Hudson for 155 years. A ten minute walk brings you to Metro North and 45 minutes later, Grand Central. Historic downtown Ossining — its shops, restaurants, and the extraordinary Sing Sing Museum — is at your doorstep. A rare opportunity to live inside a piece of history, on the banks of one of the great rivers of the world.

28 Hamilton Avenue, Ossining
$3,995,000
7 Beds ⋅ 6 Baths ⋅ 1012192 MLS
Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular 7-bedroom main residence, where grand, light-filled rooms showcase timeless craftsmanship and sweeping vistas from nearly every window. Multiple primary suites and en suite bedrooms provide exceptional comfort and flexibility for hosting overnight guests. The property also features a 5-bedroom, 2 bath, caretaker’s home and a historic carriage house with a 5-car garage, horse stalls, a chicken house, and a sheep house—ideal for equestrian pursuits, hobby farming, or simply enjoying the pastoral lifestyle. Whether you envision a private compound, event venue, or generational retreat, this setting offers endless possibilities. With its rich heritage, refined elegance, and serene privacy, Old Dam Farm is more than a property—it’s a place to create memories that will last a lifetime.

433 Arcady Road, Ossining
$639,222
3 Beds ⋅ 1 Baths ⋅ 1011590 MLS
Welcome to this beautifully maintained vintage Colonial, ideally situated on a desirable corner lot in the heart of the village. Combining classic character with thoughtful updates, this spacious home offers comfortable living both inside and out. The first floor features hardwood floors, high ceilings, a bright eat-in kitchen, dining room, an inviting living room, and laundry off the kitchen. Upstairs, you'll find 3 generously sized bedrooms and a hall bath. A walk-up attic and expansive basement provide abundant storage and future possibilities. Outdoor living is equally impressive, with a fully fenced yard, expansive stone patio perfect for entertaining, front and rear porches, and an above-ground oil tank. A detached two-car garage and driveway offer off-street parking for up to four vehicles. Conveniently located within walking distance of schools, parks, village amenities, shops, restaurants, and public transportation, this home offers the perfect blend of historic charm, modern convenience, and exceptional outdoor space. Don’t miss this opportunity to enjoy village living at its best! There are no audio recording devices inside this property.

219 Spring Street, Ossining
$2,500
1 Beds ⋅ 1 Baths ⋅ 1009795 MLS
Bright and inviting 2nd-floor rental apartment located in a well-maintained multi-family home in the charming Town and Village of Ossining. This sun-filled residence offers beautiful natural light throughout the day and spectacular sunset views, creating a warm and welcoming atmosphere. A standout feature of this large apartment is the bonus office room, perfect for working from home, studying, creative pursuits, or additional flex space to suit your lifestyle. Conveniently situated just a 10-minute walk to the Ossining Metro-North Station, providing approximately a 50-minute commute to Grand Central Terminal. Enjoy easy access to local bus lines, parks, supermarkets, laundromats, museums, and a variety of international dining options. Residents will appreciate the vibrant community amenities, including creative arts programs, recreational activities, and access to indoor swimming facilities. This desirable location combines small-town charm with outstanding convenience, making it an excellent place to call home. Don't miss this opportunity to enjoy comfortable living in one of Westchester County's most sought-after river towns.

269 Spring Street Unit #2nd Floor, Ossining
$500,000
3 Beds ⋅ 3 Baths ⋅ 1005194 MLS
Welcome to this beautiful triplex. Taxes do not reflect STAR. It’s a short distance to the Metro North train station and downtown Ossining with it’s restaurants, shops and Farmer’s Market. 3rd floor unit is occupied and can only be shown when the tenant is present for pre-arranged appointments. There is a cistern behind the house with stones on top of it. Please do not disturb it. The garage was probably originally a stable. The water main and sewer lines were replaced in 2025

237 Spring Street, 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
$350,000
1 Beds ⋅ 1 Baths ⋅ 1007742 MLS
Discover The Perfect Blend Of Tranquility And Convenience In This Stunning Second Floor End Unit At Scarborough Manor. This Beautifully Appointed One Bedroom, One Bathroom Apartment Offers Breathtaking Seasonal Views Of The Hudson River, All While Providing A Serene Woodland Ambiance That Makes You Feel Miles Away From It All. Step Inside To Find Soaring 9 Foot Ceilings And An Oversized Living Space That Is Both Inviting And Versatile. The Expansive Living And Dining Areas Create A Warm And Welcoming Atmosphere, Perfect For Hosting Intimate Gatherings Or Enjoying Quiet Evenings By The River. Scarborough Manor Is More Than Just A Home, It’s A Vibrant 24 Hour Gated Community That Boasts An Array Of Amenities, Including A Gorgeous Clubhouse, Heated Pool, Sauna, Gym, Billiards Room, And A Library, All Included In Your Monthly Maintenance Fee. Enjoy Peace Of Mind With Exterior Windows Cleaned Twice A Year And Never Worry About Losing Power, As The Entire Complex Is Equipped With A Backup Generator. Energy Conscious Solar Panels Are In Place To Help Lower Your Electric Costs, Making This Home As Efficient As It Is Beautiful. Conveniently Located Within Walking Distance To Scarborough Train Station, Scarborough Manor Places You Just Moments Away From Fantastic Shopping, Delectable Dining Options, And Vibrant Cultural Attractions. Don't Miss This Opportunity To Experience The Ultimate In Waterfront Living! Schedule Your Private Showing Today And Immerse Yourself In The Unparalleled Charm And Elegance Of This Exceptional Co-Op. Your dream Home Awaits!

16 Rockledge Avenue Unit #2D-1, Ossining
$724,222
2 Beds ⋅ 3 Baths ⋅ 1008140 MLS
Experience turnkey luxury in this beautifully renovated corner unit at The Woods, where every detail has been thoughtfully updated from top to bottom. The heart of the home is the custom high-end Bilotta kitchen, featuring a granite center island with seating, Bosch stainless steel appliances, induction cooktop, pantry, and under-cabinet lighting. The open-concept main level is ideal for both everyday living and entertaining, showcasing a custom fireplace, a sophisticated leathered quartzite bar, a private first-floor office, and a stylish powder room. Additional upgrades include updated electrical, baseboards, windows, recessed lighting, custom blinds, luxury vinyl flooring, and a redesigned balustrade. Upstairs, the spacious primary suite offers a true retreat with a luxurious spa-inspired bath featuring an oversized rainforest shower with marble seat and niche, dual quartzite vanity, and a custom walk-in closet illuminated by a skylight. The second level also includes an updated hall bath, a secondary bedroom with new carpeting, and an enclosed bonus room perfect for guests, a home office, or recreation space. Modern comforts continue with a Navien tankless boiler and hot water system providing efficient, unlimited hot water. Outdoors, relax on the private covered patio surrounded by beautifully landscaped specimen plantings, including Japanese maple and hydrangeas. A significant value-add: the $15,000 roof assessment has already been paid in full. Residents enjoy access to community amenities including a pool and tennis courts, offering a low-maintenance lifestyle in a desirable setting. There are no audio recording devices inside this property.

86 Woods Brooke Terrace, Ossining
$530,000
3 Beds ⋅ 2 Baths ⋅ 1001582 MLS
Full of warmth, character, and timeless appeal, this charming colonial home offers a wonderful blend of classic details, comfortable living spaces, and an exceptional location in the heart of Ossining. Set on a beautiful property with a spacious yard, this special home provides the perfect backdrop for gardening, entertaining, outdoor play, or simply enjoying a quiet evening outdoors. Inside, you'll find inviting spaces filled with character, including a welcoming living room, formal dining room, bonus room ideal for a home office, den, or playroom, and a large eat-in kitchen that serves as the heart of the home. A convenient main-level laundry area, three bedrooms, one-and-a-half baths, and a full unfinished basement complete the home's functional and flexible layout. The outdoor space is truly a standout feature. The expansive yard offers endless possibilities for recreation, gardening, gatherings with family and friends, or creating your own private retreat. Whether hosting summer barbecues, enjoying morning coffee on the porch, or watching the seasons change, this property offers a lifestyle that is increasingly hard to find. Ideally located just minutes from downtown Ossining, you'll enjoy easy access to local restaurants, cafes, shops, parks, and the popular Ossining Farmers Market. Nature lovers will appreciate nearby waterfront parks, scenic trails, and recreation opportunities along the Hudson River. Commuters will love the convenience of the Ossining Metro-North station, offering direct access to New York City while allowing you to enjoy all the charm and community of Rivertown living. Rich in character, filled with potential, and situated in one of Westchester's most vibrant riverfront communities, 33 Maurice Avenue is a place you'll be proud to call home.

33 Maurice Avenue, Ossining
$155,000
1 Beds ⋅ 1 Baths ⋅ 1005870 MLS
Welcome to this beautifully maintained one-bedroom, one-bath co-op in the highly sought-after Highland Terrace complex in Ossining — where opportunities to own rarely become available. Filled with natural sunlight throughout, this inviting home offers a warm and airy atmosphere from the moment you step inside. The versatile entry foyer offers the perfect flex space to suit your lifestyle — ideal as a dining area for entertaining or easily transformed into a comfortable home office or work-from-home setup. The updated kitchen is thoughtfully designed with porcelain tile flooring, granite countertops, a stylish soapstone backsplash, and stainless-steel appliances, creating the perfect blend of elegance and functionality. The spacious living room is bathed in natural light from oversized windows that offer peaceful views of the beautifully wooded grounds while also overlooking the unit’s conveniently assigned parking space. The generously sized bedroom offers a bright and tranquil retreat, featuring three large windows that fill the space with natural light and a spacious closet providing excellent storage and organization. The beautifully appointed bathroom features a full tub and an elegant granite vanity topped with a striking white vessel sink. Three stylish lighting sconces provide a warm, sophisticated ambiance, adding both charm and functionality to the space. Residents enjoy exceptional amenities including a stunning in-ground pool, charming shared front patio, and scenic walking trails that provide a peaceful, park-like setting. The unit includes one assigned parking space along with ample visitor parking for guests. Monthly maintenance covers heat, hot water, taxes, and building/property maintenance, offering excellent value and convenience. (Maintenance does not include the Basic STAR deduction.) Additional conveniences include a laundry room and private storage located in the building just across the courtyard. The co-op is wired for both Cablevision and Verizon Fios and is ideally located close to public transportation, shopping, dining, and Metro-North, making commuting a breeze. A rare opportunity to own in one of Ossining’s most desirable communities — don’t miss it!

125-3 S. Highland Avenue Unit #C5, 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
$299,000
4 Beds ⋅ 3 Baths ⋅ 1004901 MLS
Opportunity knocks on this exceptionally private, 2+ acre parcel tucked away on a serene street ending with a cul-de-sac in the sought-after Town of New Castle. Whether you are looking to take on a complete top-to-bottom renovation or build the custom home of your dreams, this property offers the perfect foundation and acreage for your vision. While you'll feel worlds away in your own private woodland retreat, you are minutes from the best of the Hudson Valley. Commuting is a breeze with easy access to the Taconic State Parkway and both the Ossining and Croton-Harmon Metro-North stations. Enjoy an unmatched lifestyle surrounded by local culture and nature. You're just a short drive from daily conveniences, schools, and parks, as well as other local highlights including Teatown Lake Reservation, Kitchawan Preserve, Sunny Ridge, the North County Trailway, the historic Jacob Burns Film Center and both Sleepy Hollow Country Club and Hudson National. Bring your architect, your contractor, and your imagination. Property being sold strictly as-is.

5 Maria Lane, Ossining
$1,079,000
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
$450,000
3 Beds ⋅ 1 Baths ⋅ 995689 MLS
20 Samstag Ave is the kind of home that sparks ideas the moment you enter. Tucked into an established Ossining neighborhood just minutes from the Hudson River, this classic 2-story Cape-style home with charming dormers and a cheerful red-painted front porch is ready for its next chapter, and for the right buyer, that chapter could be something special. Inside, three bedrooms, a full bath, and 930 square feet of light-filled living space stretch across two levels. The walls have stories to tell, the spaces invite imagination, and every room offers an opportunity to restore, reinvent, or simply bring fresh life to what is already here. The standout living room features warm knotty-pine wood paneling and an incredible mid-century modern built-in shelf and wall divider that feels straight out of another era. It's the kind of architectural detail you simply cannot recreate with a quick trip to a big box store. The kitchen offers a more updated counterpoint with maple-tone cabinetry, a gas range, and tile flooring that flows through the main level, while the upstairs bedrooms tuck under classic Cape sloped ceilings, ideal as cozy retreats or a quiet home office. Outdoors, one of the home's most surprising gifts comes into view: a generous, fully fenced backyard with mature shade trees, a level lawn, and a private rear entry. It's a rare bonus at this price point and a versatile space for entertaining, gardening, or simply enjoying the outdoors. The basement adds another layer of potential. Whether the vision is a workshop, studio, recreation space, or simply more room to spread out, the opportunity is there for someone willing to bring it to life. The location does a lot of the heavy lifting, too. Ossining is one of the Hudson Valley's most loved river towns and one of the smartest commutes north of the city. The Croton Metro-North and other stations on the Hudson Line are just a short drive away, putting Grand Central roughly 45 to 55 minutes from your front door, making this an ideal opportunity. Downtown Ossining is minutes from the house, with its growing roster of restaurants, cafes, and shops, the Sing Sing Kill Greenway, and Louis Engel Waterfront Park where the Hudson and the Palisades stretch out in front of you. Weekends nearby look like the Old Croton Aqueduct trail, Teatown Lake Reservation, Rockefeller State Park Preserve, and the antique-and-eatery rhythm of neighboring Croton-on-Hudson and Sleepy Hollow. For buyers who appreciate homes with character, history, and room to create something personal without giving up an easy commute to NYC, 20 Samstag Ave offers a rare opportunity to shape a space into something truly your own.

20 Samstag Avenue, Ossining
$799,000
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
$699,000
7 Beds ⋅ 4 Baths ⋅ 993813 MLS
Perfect for investor or end-user. Located in the heart of the village, the structure sits on a 4,356-square-foot lot and offers a classic architectural style characteristic of the historic downtown Ossining area. This multi-family, 2 family with accessory unit ground floor unit. Property features 7 bedrooms and 4 bathrooms.

67 State Street, Ossining
$215,000
2 Beds ⋅ 1 Baths ⋅ 991549 MLS
Welcome to Highland Terrace, a light-filled, top-floor end unit in a pet-friendly community. This bright and well-maintained two-bedroom apartment features an updated kitchen with granite counters, newer appliances, and a convenient pass-through to the living and dining area. The spacious living room offers plenty of space and great natural light, while both bedrooms include good sized closets. A flexible bonus space off the entrance is perfect for a dining nook or home office. Highland Terrace is a pet-friendly complex (up to two pets allowed) offering assigned parking, an outdoor pool, basketball court, and beautifully maintained grounds. Ideally located just minutes from shops, restaurants, parks, and the Ossining and Scarborough Metro-North stations, making commuting to NYC simple and convenient.

133-3 S Highland Avenue Unit #5B, Ossining
$550,000
6 Beds ⋅ 3 Baths ⋅ 991931 MLS
Legal 2-family opportunity in the heart of Ossining offering exceptional value, versatility, and upside potential. Priced at $550,000, this spacious property features a 5-bedroom, 3 full bath layout plus a separate studio apartment with its own private entrance—ideal for investors or owner-occupants looking to generate rental income. Set on a 7,405 sq ft lot, the home offers approximately 2,276 sq ft of living space with classic architectural charm including a mansard-style roof, covered front porch, and original details throughout. The property features multiple living areas, generous room sizes, and flexible layout options to accommodate extended living or rental configurations. Interior spaces offer a blend of character and opportunity. Bright rooms with hardwood floors, large windows, and high ceilings provide great natural light. Kitchens and baths are functional with room for updates, making this a strong value-add opportunity. Separate living quarters allow for privacy between units, enhancing rental appeal. The exterior offers a large private driveway with ample off-street parking, a rare find in this area, along with a spacious backyard and patio area—perfect for outdoor use, entertaining, or future improvements. A detached structure and additional outdoor space provide even more potential. Located on a quiet residential street, the property is just minutes from downtown Ossining, shops, restaurants, parks, and the Hudson River waterfront. Commuters will appreciate easy access to Metro-North, offering a convenient commute to NYC. The area continues to see strong demand due to proximity to major employment hubs including White Plains, Tarrytown, and Stamford. With comparable multi-family properties in Ossining selling significantly higher, this property presents a compelling opportunity to build equity and maximize returns. Whether you are looking to invest, renovate, or live in one unit while renting the other, this is a property with strong income potential and long-term growth. A rare chance to own a legal 2-family with a separate studio in a sought-after Westchester location.

41 Ellis Place, Ossining
$234,500
2 Beds ⋅ 1 Baths ⋅ 987888 MLS
Spacious two bedroom light & airy updated END-unit in heart of town offers easy affordable living in a quiet, pet-friendly community. Common charges include taxes, heat, water, buildings/grounds and pool maintenance, insurance & parking. This low-maintenance one-level unit is located on the first floor. Features include an updated Kitchen with quartz countertops, white cabinetry, natural gas cooking stove; high-hat lighting and wiring for Verizon Fios/Spectrum/Cablevision. Multiple ceiling fans and windows in every room; multiple a/c units included. Corner location offers more windows and privacy than most and lets in more natural sunlight. Lovely landscaping, basketball/sports court, outdoor in-ground pool & common-use patios with BBQ set ups, along with well-maintained outdoor seating areas. Ossining's award-winning Schools are known for having the most Intel Science winners year after year along with great Robotics & STEM Programs. This is one of a very limited number of co-op complexes that is pet friendly (2 pet limit). Walk to the Arcadian Shopping Center's stores, banks and restaurants (i.e., McDonald's, Verizon, Starbucks, Capri Pizza, Valley Bank, Stop & Shop Supermarket +) all for your dining & shopping pleasure. If you work in the City, or want to head up north to Bear Mountain and beyond, Highland Terrace Co-ops has easy access to all main thoroughfares. You're only minutes from Metro-North's Hudson train line with less than an hour's commute to Manhattan. Nelson Park is just a block away. Scenic Aqueduct walking trails are nearby; and only seconds from riverfront options to fish or sail on the Hudson! Who needs anything more? Why not say "Welcome Home" to Unit #B3 today.

127-1 South Highland Avenue Unit #B3, Ossining
$699,000
3 Beds ⋅ 2 Baths ⋅ 985026 MLS
This charming 3-bedroom, 2-bath home in the Village of Ossining, is a legal 2 family and is currently being used as a single family. Features include a small backyard, a detached 1-car garage, and a convenient location close to shops, transportation, and amenities.

32 Terrace Avenue, Ossining
$675,000
3 Beds ⋅ 3 Baths ⋅ 977440 MLS
Welcome to 24 Highview Road, a classic Split-Level home offering the perfect blend of privacy and potential on a rare 1.32-acre lot in the Town of New Castle. This 3-bedroom, 2.1-bathroom residence features 1,959 square feet of living space with several recent high-value mechanical and interior upgrades. The main level boasts a spacious living room with a cozy fireplace and a seamless flow into the dining area. Notable recent improvements include: Interior Refresh (2024): Freshly painted rooms and brand-new vinyl flooring throughout the lower level. Updated Bathroom: A newly renovated bathroom adds modern comfort to the home. Mechanical Peace of Mind: Equipped with a Generac whole-house generator (2022) and a brand-new above-ground oil tank (2025). Ample Storage: Featuring two scuttle-access attics and a full basement for all your storage needs. The primary bedroom offers a truly unique feature: a structural rooftop column with a C/O for a telescope, perfect for the hobbyist stargazer. Outside, the expansive property includes a shed and a secondary structure (formerly a coop), offering endless possibilities for gardening or outdoor recreation. Conveniently located in the Ossining school district with an attached 2-car garage, this home is ready for its next chapter.

24 Highview Road, 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

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