Ossining, NY Houses for Sale

**FREE EGGS!** Seize the opportunity to own this incredible farmhouse, perfectly designed for those who dream of expansive property, vibrant gardens, lush fresh berries, and the delight of raising chickens right in your backyard. This enchanting antique farmhouse, originally built in 1868, has undergone a meticulous renovation that seamlessly integrates modern conveniences while preserving the

Cindy Kief Corcoran Legends Realty

Charming & Surprisingly Spacious Cape in Briarcliff ManorDon’t let its unassuming exterior fool you—this 5-bedroom, 4-bath Cape-style home in the heart of Briarcliff Manor’s desirable Neighborhood Park neighborhood is full of unexpected space, comfort, and charm. Located within the sought-after Briarcliff School District and enjoying full access to Briarcliff recreation, this home offers the

Wendy Phillips Corcoran Legends Realty

This spectacular 4,662 sq ft renovated home features an open concept with soaring cathedral ceilings, fantastic natural light, four bedrooms and 4.2 baths has everything you have been searching for including an end of a cul-de-sac location all within the sought after gated community of Rosecliff. Soaring 20ft ceilings with multiple skylights, a gorgeous renovated kitchen with stainless steel

Jamey Gelardi Houlihan Lawrence Inc.

Sprawling Cape Cod style home with first floor primary suite on a fabulous, private setting. Kitchen has stainless appliances and stone counters, formal dining room has large bay window looking out at the fenced-in property, and living room has high ceilings and a fireplace. Sun Room off the kitchen has 3 skylights and the covered patio off the kitchen overlooks the lush landscaping, backing up

Mark Seiden Mark Seiden Real Estate Team

Welcome to 38 Ganung Drive in Ossining, where flexibility, space, and location come together in one exceptional property. This 4-bedroom, 3.5-bath home offers a versatile layout that works beautifully for a variety of needs. Whether you're looking for a mother/daughter setup or need space for extended living with a separate in-law suite, this home provides options that are hard to find.Set in an

Alex Mashkin Keller Williams Realty Partner

Welcome to 3 Waterview Drive, an elegant Colonial nestled in the prestigious Waterview Estates of Ossining. This recently constructed, light-filled gem spans over 3,400 square feet and embodies sophisticated modern living at its finest. Enjoy seasonal river views from the windows of your primary suite, relax on the charming porch or back patio, or venture out to the nearby Aqueduct Trail and

Yarden Ronen-van Heerden Compass Greater NY, LLC

Welcome Home!To this beautifully maintained five-bedroom, three-bathroom home which offers ample space and modern amenities for comfortable living and entertaining. Located in a serene neighborhood, it blends timeless charm with contemporary features.Key Features:- Spacious bedrooms, including a main suite with a private bathroom and ample closet space.- Two full bathrooms and a half bath with

Feliciano Ortiz Call it Closed Intl. Realty

Eagle's Nest. Perched majestically on a breathtaking property overlooking the Hudson River, this historical architectural masterpiece will leave you amazed. A true marvel, this 5-bedroom, 4.5-bathroom single-family home was built for the legendary 1920s theater and film star, Jeanne Eagels. Prepare to be transported to a world of unparalleled charm and craftsmanship as you step into the

Nancy Kennedy

Luxurious Hudson River retreat on a private cul-de-sac. Experience elevated living in this extensively upgraded residence, perfectly positioned on a quiet cul-de-sac with breathtaking views of the Hudson River. From the moment you step inside, soaring cathedral ceilings, an open-concept floor plan, and spacious, light-filled rooms create an atmosphere of modern elegance and comfort. At the heart

Eric Bernstein Compass Greater NY, LLC

Welcome to this beautifully maintained Center Hall Colonial, perfectly situated at the end of a peaceful cul-de-sac in Briarcliff Manor. Set on .94 acres of level land, this spacious home offers more than 3,000 square feet above ground, with four generous bedrooms, two and a half baths, and a private main-floor office. From the moment you step inside through the newer steel front door with leaded

Suzan Zeolla Houlihan Lawrence Inc.

Welcome to this truly special 3-bedroom, 2-bathroom Victorian home, gracefully nestled in the heart of Ossining’s desirable Chilmark neighborhood. A rare blend of timeless charm and modern updates, this residence invites you to step into a world where classic craftsmanship meets today’s comfort and style.From the moment you arrive, the home’s character captivates — a nod to its historic roots

Heather Bouza William Raveis-New York, LLC

Nestled at the end of a serene cul-de-sac, this extraordinary custom-built home in Briarcliff Manor welcomes you with a grand tree-lined circular driveway. Spanning nearly 10,000 sq. ft., this home is a masterclass in luxury, craftsmanship, and thoughtful design.Step inside to discover a beautifully appointed main level, where a custom gourmet eat-in kitchen, complete with a butler’s pantry, sets

Hillary Landau Compass Greater NY, LLC

Set back from the road, this mid-century modern home features three bedrooms upstairs and a guest room downstairs. The spacious primary bedroom has a full bath ensuite. The living room with a fireplace is open to the dining room with a slider leading to a deck overlooking the yard. The kitchen was recently remodeled with new countertops, backsplash, sink with sensor faucet and instant hot

Margaret McMullen Keller Williams NY Realty

Welcome to 16 Forest Avenue, an elegant retreat nestled in the charming enclave of Ossining, NY. This beautifully appointed residence offers an exquisite blend of sophistication and comfort across a generous 1,488 square feet.Step inside and be greeted by gleaming hardwood floors that lead you through a spacious layout featuring four well-appointed bedrooms and two pristine bathrooms.

Korab Krasniqi Compass Greater NY, LLC

Set on 2.5 tranquil acres of open spaces, lush woods, waterfalls and meandering stone walls, this one-of-a-kind, artfully designed residence offers a seamless connection to nature. Cross a bridge over babbling Sparta Brook to the wrap-around deck, where you can take in the serene beauty of your own secluded retreat. A welcoming entry foyer opens into the dramatic, beamed and vaulted Great Room,

Matthew Valvano Berkshire Hathaway HS NY Prop

Welcome to 25 Highview Road, a charming and well-maintained colonial-style home nestled on a picturesque cul-de-sac in the desirable New Castle area of Ossining. Making its debut on the market, this hidden gem seamlessly blends space, comfort, and accessibility, offering an ideal setting for your next chapter! Resting on a green acre, the property boasts abundant outdoor space for relaxation and

Yarden Ronen-van Heerden Compass Greater NY, LLC

Nestled in the heart of the picturesque Hudson Valley, this stunning Tudor-style mansion is a true dream estate. Boasting an impressive 9,481 sq ft of living space, this magnificent property is situated on 50 acres of meticulously landscaped gardens, making it one of the most sought-after locations in the county.The estate features a 3-acre lake with a charming boathouse, a sparkling pool, a

Dalia Valdes Julia B Fee Sothebys Int. Rlty

Welcome to 43 Ganung Drive, a beautifully updated home nestled in the heart of Ossining—just a 10-minute drive to the Metro-North station for a quick and easy commute to Grand Central. Located near the scenic Hudson River, this home perfectly blends charm and modern style.Step into the heart of the home—a renovated open-plan kitchen thoughtfully designed for the home chef. Outfitted with modern

Deirdre Coffey Compass Greater NY, LLC

Welcome to this beautifully maintained Colonial, ideally situated less than a mile from the heart of Briarcliff Manor. Thoughtfully updated and tastefully appointed, this home features exquisite custom woodwork, built-in cabinetry and high-end finishes throughout.The bright, eat-in kitchen opens through elegant French doors to a stunning stone patio and a level backyard surrounded by mature

Susan Slotnick William Raveis Real Estate

Welcome to 12 STONE AVENUE. . and this Elegant Ranch-style home nestled in the village neighborhood of "FOREST PARK." Specimen shrubbery and perennial plants have been carefully maintained and compliment the grounds. You enter into the Bright & Airy Living Room and Dinning area. Hardwood flooring is hidden under the wall-to-wall carpet in this room - but exposed in the three Bedrooms. The

Greg Kane Kane & Associates

Welcome to 2 Jenkins Ct, located on a quiet, cul-de-sac, just 1.3 miles to the Ossining Metro North Station, walking distance to local elementary and middle school; and also within minutes to local shopping, restaurants and several parks. Large entry foyer with half bath, Living room with fireplace, formal dining room and eat-in-kitchen with access to the rear patio and fenced in yard, make

Tina Ciufo William Raveis-New York LLC

This charming 4-bedroom cape cod in the sought after "Indian Village" on a cul de sac offers the perfect blend of cozy and convenient living. With its warm and inviting atmosphere, you are sure to feel right at home. The classic design of the house gives it a timeless appeal that you'll appreciate for years to come. Outside, you will find a large private backyard that is perfect for outdoor

Rose Asprea Houlihan Lawrence Inc.

Charming ranch offers a bright and spacious living room with built-in shelves, an eat-in-kitchen with an island, granite counters and stainless steel appliances. Privacy abounds in this spacious, fenced-in yard. One car garage. Storage room in the basement. Ample off-street parking in the driveway. Close to shops, parks, and transportation. The Croton Aqueduct Trail is one block away. Three

Maureen McEnroe Joyce Realty Corp

Welcome to this sun-filled and spacious 3-bedroom home that lives like a 4-bedroom, offering the perfect blend of comfort, versatility, and convenience. Situated on a cul-de-sac, this home features a private, level, fully fenced-in yard, ideal for outdoor enjoyment, play, and entertainment. Inside, you’ll find a flexible bonus room, perfect as a home office, nursery, or gym, plus an additional

Jo Ann Reilly Julia B Fee Sothebys Int. Rlty

Come view this immaculately kept gem located in Ossining Village. First time to market in 45 years, this charming 4 bedroom, 2 full bath classic Cape boasts a new kitchen and updated baths. First floor features a bedroom with full bath for primary use or potential guest suite. Second floor has three rooms and full hall bath. Third room on this level perfect for nursery or home office. Basement

Kathy Kane Coldwell Banker Realty

This inviting ranch-style home offers breathtaking Hudson River views from the moment you step inside. The open, flowing floor plan is perfect for modern living. The light-filled dining room leads into a newly renovated kitchen (2022) with quartz countertops, stainless steel appliances, and direct access to the outdoors. The spacious living room features a cozy brick fireplace, and the

Zachary Zweibon Compass Greater NY, LLC

The Roy O. Allen House on Marlborough Road is arguably one of the most renowned modern homes in Westchester County and a celebrated icon of mid-century glass architecture worldwide. Featured prominently in Architectural Digest, Dwell, GQ, The New York Times, and TV shows like Fallout and Hunters (Amazon Prime), this 1957 International Style pavilion is a masterwork of design. (In fact, these

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

Great project! Perfect for a new flipper! Lots of work has already been done. Located close to everything downtown Ossining has to offer. Lower level includes a large flex space plus a full bath with tub. Wonderful backyard space will be perfect for entertaining friends and family. Stairs/Walkway and garage require extensive work. House sold "As-Is" with violations on garage. Please be

Derek Greene Greene Realty Group

New Construction Home – 3 Sherman Pl, Ossining, NY – 65% Complete!Situated on a quiet street, this spacious home features 4 bedrooms and 2.5 bathrooms, an open-concept layout, The sun-drenched living area boasts large windows, high ceilings, and sleek hardwood floors, creating an inviting atmosphere for relaxation and entertaining. Upstairs, the primary suite offers a generously sized and

Arif Baksh YourHomeSold Guaranteed Realty

Welcome to Boxwood: A Timeless RetreatBoxwood offers a unique blend of classic Williamsburg Colonial architecture and thoughtful modern upgrades, creating a warm and inviting home that caters to both comfort and elegance. Situated on 3.895 acres of beautifully maintained grounds, this gated property provides a peaceful escape while remaining functional and accommodating for modern

Timothy Hegarty Houlihan Lawrence Inc.

Nestled in a peaceful and picturesque neighborhood in Ossining, NY, 15 Cooper Drive offers a beautiful blend of comfort and convenience. This spacious 5-bedroom, 4 1/2 -bathroom home is perfect for families seeking a retreat that still provides easy access to everything you need. With generous living space, this home provides an ideal layout for both relaxation and entertaining.The

Bopaul Sookdeo YourHomeSold Guaranteed Realty

Luxury Meets History: Discover 36 Revolutionary Road, a true Westchester Treasure. Welcome to this private 3.83-acre estate that is perfectly positioned between the Hudson River and Sleepy Hollow Country Club. World-class dining, shopping and train are nearby, blending convenience with serene privacy. The stately home boasts five spacious ensuite bedrooms, including a spectacular primary

Elaine Wasserman Houlihan Lawrence Inc.

Experience Refined Luxury and Unparalleled Lifestyle in Briarcliff Manor. Discover this exceptional 5-bedroom, 3.5-bath colonial, masterfully reimagined by prominent Westchester County builder with exquisite attention to detail. Perfectly situated on a large lot in the prestigious River Road neighborhood, this home offers a seamless blend of elegance, comfort, and modern living. Step inside to

Lindsay DiLoreto Houlihan Lawrence Inc.

Classic Stoneface Ideal Colonial Cape on Lovely .25 acre lot with Stone Patio and Large Outdoor Masonry Ovens to make your Outdoor Entertaining Epic! This 3,000 s/f House has a Full Bathroom on each of the Three levels. First Floor Bedroom and Bath, Kitchen with nice Cabinetry with New Stainless Appliances & Granite Counters, Formal Dining Room, Living Room with Fireplace and Beautiful Sun Porch

Thomas Nigro Schatz Realty Group

Waterfront!!! Experience your own slice of paradise in this charming colonial with direct Croton River frontage and access. This well-maintained home features spacious rooms, a renovated kitchen, and a walk-up attic, combining comfort and character. The level yard is ideal for outdoor activities, with kayaking, fishing, and bird watching just steps away. Ideally situated minutes from the Aqueduct

Ken Wile Redfin Real Estate

Seize this rare opportunity to own an iconic estate rich in history, dating back to the 1890s. This distinguished property, known as “The Manor House,” was built for and live in by Walter Law, the founder of The Village of Briarcliff Manor. Constructed on Brier Cliff Farms, originally acquired from James Stillman, then-President of National City Bank (now Citibank), the estate at 139 Scarborough

Elana Zimmerman Julia B Fee Sothebys Int. Rlty

Calling all antique lovers! On the hilltop of Ryder Road in Ossining sits an historic property going back centuries, on the market for the first time in decades. The 33 Ryder Road 1826 farmhouse, claimed to be Ossining's oldest residence by The Citizen Register of 1936, is oozing with original charm, including its huge rocking chair front porch, 7' high ceilings, wide plank hardwood floors and

Lynn Harmonay North Country Sothebys Int Rlt

Charming Tudor on a tree-lined street with tons of potential. Rooms live large - huge living room with fireplace, kitchen with center island, study/den bonus room on the main level. Full sized unfinished basement where the possibilities are endless, and a full-height attic. Two-car detached garage is perfect for a workshop. Oversized deck and great year. Don't miss the opportunity to turn this

Tracy Salciccia ERA Insite Realty Services

Experience breathtaking, panoramic views of the majestic Hudson River from this exceptional sanctuary in Briarcliff Manor, NY. Reimagined and completely rebuilt in 2011, this unique home seamlessly blends elegance with serenity, offering a true connection between indoor and outdoor living. The property is designed to immerse you in nature’s beauty, with every space thoughtfully crafted to elevate

Elizabeth Hargraves Julia B Fee Sothebys Int. Rlty