Homes with Pools for Sale in Ossining, NY

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COMING SOON

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Discover an exceptional opportunity within the highly sought-after Liberty Knoll Town Home Community. Whether you are a first-time homebuyer seeking an entry into the Westchester market, a commuter desiring convenience with a walk to the Metro North Train Station or looking to downsize without compromising on quality and community, 3 Davids Lane presents a sophisticated, low-maintenance lifestyle. The main level boasts gleaming stainless-steel appliances in the kitchen updated powder room and built-in cabinetry with beverage center. The open layout extends to a private balcony which is perfect for al fresco dining or enjoying quiet moments. The upper level provides a tranquil retreat, featu

$375,000

1 bed1.5 baths1,158 sq ft

3 Davids Ln, Ossining, NY 10562

Private balcony • Walk-in closet • Exceptional storage

Listing by Corcoran Legends Realty

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
A rare Hudson Valley country estate, Rose Lodge offers exceptional privacy, scale and versatility on 17.9 acres, with a private lake, beautifully sited pool, terraced gardens, sweeping level lawns and multiple residences, all less than an hour from Manhattan by express train. Rich in history and once owned by the Gilded Age Van Cortlandt family, the beautifully restored 1840 main residence is not landmarked, allowing its historic character to coexist with modern living. Inside, a striking checkerboard marble foyer introduces gracious, light-filled rooms with beautifully preserved period details. Elegant formal spaces flow naturally into a welcoming family room and bar surrounded by windows

$2,200,000

7 beds6 baths5,502 sq ft

83 Somerstown Rd, Ossining, NY 10562

Terraced gardens • Multiple residences • Private lake

Listing by Julia B Fee Sothebys Int. Rlty

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Welcome to this spacious and sun-filled two bedroom co-op in the beautiful Highland Terrace! Step into a welcoming foyer, currently arranged as a home office but easily adaptable as a dining area or flexible bonus space. The generously sized kitchen offers abundant cabinet storage and stainless-steel appliances. Just beyond, the bright and airy living room features large windows that fill the space with natural light. Down the hallway, you will find a spacious primary bedroom with ample closet space, along with a second bedroom that functions as a guest room, home office, or additional living space. The tiled bathroom is complete with a full bathtub. Outdoor enthusiasts will especially love

$230,000

2 beds1 bath950 sq ft

129-1 S Highland Ave Unit B3, Ossining, NY 10562

Large windows • Ample closet space • Home office

Listing by Howard Hanna Rand Realty

3D WALKTHROUGH

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details, including wide-plank pine floors, original farm doors, hand-crafted millwork, and three fireplaces. Offering exceptional versatility, the estate is ideally suited as a private country retreat, equestrian property, or multi-generational residence. Set on over five picturesque acres, the grounds are a t

$1,350,000

5 beds3.5 baths4,828 sq ft

15 Inningwood Rd, Ossining, NY 10562

Three fireplaces • Five acres • 5.12 acre lot

Listing by BHHS River Towns Real Estate

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Welcome to LIBERTY KNOLL. . . This attractive 1 BEDROOM, 1.5 BATHS Tri-level townhouse is ready for its next owner! The Eat-in-Kitchen has ceramic tile flooring, a Frigidaire gas oven/range/microwave & dishwasher. The large Living Room leads to an inviting Deck that overlooks the rear yard. You'll find the Powder Room as well. The upper level showcases a generous size Bedroom that offers a walk-in closet and second closet. The clothes Washer/Dryer are located in the adjacent hall closet and next to the full Bathroom that offers a much appreciated double sink vanity. The Lower Level offers unfinished storage and potential living space at some point. Driveway parking along with an assig

$425,000

1 bed1.5 baths948 sq ft

17 Davids Ln, Ossining, NY 10562

Eat-in-kitchen • Unfinished storage • Community pool

Listing by Kane & Associates

Property at 61 Ganung Dr, Ossining, NY 10562, 3 beds, 2.5 baths

$839,000

3 beds2.5 baths1,792 sq ft

61 Ganung Dr, Ossining, NY 10562

Listing by K. Fortuna Realty, Inc.

Property at 41 Campwoods Rd, Ossining, NY 10562, 4 beds, 2 baths

$649,000

4 beds2 baths2,260 sq ft

41 Campwoods Rd, Ossining, NY 10562

Listing by Kane & Associates

Property at 119 S Highland Ave Unit 5E, Ossining, NY 10562, 2 beds, 1 bath

$229,222

2 beds1 bath900 sq ft

119 S Highland Ave Unit 5E, Ossining, NY 10562

Listing by Mark Seiden Real Estate Team

Property at 42 Hudson Watch Dr, Ossining, NY 10562, 1 bed, 1.5 baths

$620,000

1 bed1.5 baths1,195 sq ft

42 Hudson Watch Dr, Ossining, NY 10562

Listing by Julia B Fee Sothebys Int. Rlty

Property at 135 S Highland Ave Unit 5D6, Ossining, NY 10562, 2 beds, 1.5 baths

$242,000

2 beds1.5 baths950 sq ft

135 S Highland Ave Unit 5D6, Ossining, NY 10562

Listing by eXp Realty

Property at 129-3 S Highland Ave Unit A2, Ossining, NY 10562, 1 bed, 1 bath

$150,000

1 bed1 bath750 sq ft

129-3 S Highland Ave Unit A2, Ossining, NY 10562

Listing by Douglas Elliman Real Estate

Property at 127-1 South Highland Ave Unit B3, Ossining, NY 10562, 2 beds, 1 bath

$234,500

2 beds1 bath950 sq ft

127-1 South Highland Ave Unit B3, Ossining, NY 10562

Listing by Howard Hanna Rand Realty

Property at 23 Inningwood Rd, Ossining, NY 10562, 3 beds, 4 baths

$3,100,000

3 beds4 baths6,091 sq ft

23 Inningwood Rd, Ossining, NY 10562

Listing by Woodfront Realty, Inc.

Property at 117 Highland Unit 4F, Ossining, NY 10562, 1 bath

$124,900

Studio1 bath650 sq ft

117 Highland Unit 4F, Ossining, NY 10562

Listing by Amo Realty

Property at 433 Arcady Rd, Ossining, NY 10562, 7 beds, 5.5 baths

$3,995,000

7 beds5.5 baths5,700 sq ft

433 Arcady Rd, Ossining, NY 10562

Listing by Houlihan Lawrence Inc.

Property at 36 Revolutionary Rd, Briarcliff Manor, NY 10510, 5 beds, 6 baths

$2,995,000

5 beds6 baths7,931 sq ft

36 Revolutionary Rd, Briarcliff Manor, NY 10510

Listing by Houlihan Lawrence Inc.

Property at 51 Pinesbridge Rd, Ossining, NY 10562, 9 beds, 7 baths

$1,750,000

9 beds7 baths5,337 sq ft

51 Pinesbridge Rd, Ossining, NY 10562

Listing by William Raveis Real Estate

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ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Welcome to 385 Yorktown Road! This Raised Ranch offers 4 bedrooms and 3 bathrooms with a versatile layout and plenty of space. The beautifully finished lower level offers an ideal setup for extended family, with excellent potential for a mother-daughter or in-law arrangement. The home features hardwood floors, an attic, and bright, inviting living spaces filled with natural light. Step outside and enjoy the deck, fenced yard, and pool, perfect for relaxing and entertaining. Driveway parking adds everyday convenience. Situated in the Croton-Harmon School District with easy access to the Taconic State Parkway, shopping, dining, schools, and local amenities. A wonderful opportunity with space,

$699,999

4 beds2.5 baths1,700 sq ft

385 Yorktown Rd, Croton-on-hudson, NY 10520

Fenced yard • Raised ranch • Driveway parking

Listing by Keller Williams Realty Group

COMING SOONFLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Briarcliff Manor perfection. Vacation at home in the resort like property complete with an infinity pool, hot tub, and outdoor kitchen with a custom built contemporary offering stunning interiors. No detail or comfort overlooked. Set at the end of a private cul-de-sac, this grand Briarcliff Manor residence offers an exceptional blend of luxury, comfort, and resort-style outdoor living. A dramatic two-story entry welcomes you into beautifully appointed interiors featuring hardwood floors, custom built-ins, skylights, and two fireplaces. The spacious living and family rooms are designed for both relaxation and entertaining, while the elegant dining room leads to a stunning eat-in kitchen with

$2,950,000

4 beds4.5 baths5,382 sq ft

6 Canterbury Ct, Briarcliff Manor, NY 10510

Hot tub • Custom built-ins • Infinity pool

Listing by Houlihan Lawrence Inc.

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Bored with all the standard cookie cutter houses out there? If so, we excitedly invite you to come see this 1 owner uniquely built home. Bring your imagination and elbow grease to take advantage of this great opportunity to own a larger home, built in 1983, in southern Westchester at an accessible price point. Come see a home built for entertainment as it sits in a class of its own. Nestled at the end of a tree lined cul-de-sac. DON’T JUDGE THIS BOOK BY ITS COVER OR YOU WILL MISS AN AMAZING OPPORTUNITY. This 3 Bedroom 3 Bath home is the last house on a peaceful cul-de-sac with no through traffic. Enjoy an abundance of natural light from skylights throughout the home. This home offers

$949,000

3 beds3 baths3,375 sq ft

107 Stephenson Ter, Briarcliff Manor, NY 10510

Uniquely built home • No through traffic • Affordable taxes

Listing by ERA Insite Realty Services

VIDEO TOUR

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
You have found Nirvana. The ultimate escape that is private, peaceful, undisturbed & uncomplicated. Nestled up a long driveway this comfortable & inviting home awaits. Spacious open floor plan focuses on the lush grounds and inground pool. Easy living on one floor with a focus on natures surroundings. Primary bedroom suite offers a large room sized walk-in closet and spacious bath. A few minute drive into the center of town and the parkway. Under 40 minutes from NYC.

$1,500,000

4 beds3 baths2,634 sq ft

100 Crow Hill Rd, Mount Kisco, NY 10549

Open floor plan • Natures surroundings • Walk-in closet

Listing by Keller Williams Realty Group

FLOOR PLAN

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
Newly Refreshed and Improved - Now is your opportunity to get into a pretty home in Briarcliff School District! Located in desirable Briarcliff Manor in the heart of Westchester, this spacious home includes open and versatile spaces that are perfect for gathering with friends and relatives. Set back from a quiet sought-after street, this home sits pleasantly on a beautiful professionally landscaped acre of property that includes Pool, decking, open lawn and fabulous old rock walls. The interior has been Freshly Painted and Quality Hardwood Floors have been refinished to reveal the gorgeous wood grain. Built in 1957, the home's sprawling design uses minimal stairs. Featuring 3 Bedrooms (liv

$1,100,000

3 beds3.5 baths2,624 sq ft

120 Cedar Dr E, Briarcliff Manor, NY 10510

Sunny main level • Sunroom greenhouse • Minimal steps

Listing by Corcoran Legends Realty

ABOUT THIS HOME
Home with a Pool for sale in Ossining, NY:
A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection. Originally dating to 1762, the property has evolved over time and offers a unique combination of old-world charm, generous space and exceptional flexibility. The main residence features spacious living areas, a large chef’s kitchen, fireplaces, beautiful natural light and peaceful views of the grounds. While the home offers great bones and many modern day appealing features, it is ready for the next

$2,137,500

4 beds4.5 baths4,340 sq ft

82 Shingle House Rd, Millwood, NY 10546

Private mini-estate • Multiple fireplaces • 6.97 acre lot

Listing by Century 21 Elite Realty

Property at 308 Half Moon Bay Dr, Croton-on-hudson, NY 10520, 3 beds, 3 baths

$1,395,000

3 beds3 baths1,845 sq ft

308 Half Moon Bay Dr, Croton-on-hudson, NY 10520

Listing by Julia B Fee Sothebys Int. Rlty

Property at 32 Beechwood Way, Briarcliff Manor, NY 10510, 3 beds, 3 baths

$1,100,000

3 beds3 baths2,432 sq ft

32 Beechwood Way, Briarcliff Manor, NY 10510

Listing by The Foxes Real Estate

Property at 18 Brookview Dr, Pleasantville, NY 10570, 3 beds, 3.5 baths

$1,399,000

3 beds3.5 baths3,434 sq ft

18 Brookview Dr, Pleasantville, NY 10570

Listing by Houlihan Lawrence Inc.

Property at 12 E Mount Airy Rd, Croton-on-hudson, NY 10520, 6 beds, 4.5 baths

$1,450,000

6 beds4.5 baths5,107 sq ft

12 E Mount Airy Rd, Croton-on-hudson, NY 10520

Listing by Compass Greater NY, LLC

Property at 4 Annes Wood Ln, Mount Kisco, NY 10549, 2 beds, 2.5 baths

$995,000

2 beds2.5 baths1,903 sq ft

4 Annes Wood Ln, Mount Kisco, NY 10549

Listing by Houlihan Lawrence Inc.

Property at 185 Jefferson Ave, Thornwood, NY 10594, 4 beds, 3.5 baths

$1,320,000

4 beds3.5 baths3,100 sq ft

185 Jefferson Ave, Thornwood, NY 10594

Listing by Westchester Realty Consultants

Property at 2 Timberland Pass, Chappaqua, NY 10514, 3 beds, 2.5 baths

$839,999

3 beds2.5 baths1,586 sq ft

2 Timberland Pass, Chappaqua, NY 10514

Listing by Dorothy Jensen Realty, Inc.

Property at 986 Cliff Ave, Yorktown Heights, NY 10598, 3 beds, 3 baths

$859,900

3 beds3 baths2,016 sq ft

986 Cliff Ave, Yorktown Heights, NY 10598

Listing by William Raveis Real Estate

Property at 33 Greenbriar Dr, Chappaqua, NY 10514, 3 beds, 4 baths

$2,249,000

3 beds4 baths6,115 sq ft

33 Greenbriar Dr, Chappaqua, NY 10514

Listing by Houlihan Lawrence Inc.

Property at 17 Lila Ln, Chappaqua, NY 10514, 3 beds, 3 baths

$1,590,000

3 beds3 baths2,576 sq ft

17 Lila Ln, Chappaqua, NY 10514

Listing by Compass Greater NY, LLC

Property at 29 Beechwood Way, Briarcliff Manor, NY 10510, 3 beds, 2.5 baths

$999,900

3 beds2.5 baths2,443 sq ft

29 Beechwood Way, Briarcliff Manor, NY 10510

Listing by Compass Greater NY, LLC

Property at 17 Deforest Dr, Cortlandt Manor, NY 10567, 2 beds, 2.5 baths

$975,000

2 beds2.5 baths2,200 sq ft

17 Deforest Dr, Cortlandt Manor, NY 10567

Listing by Houlihan Lawrence Inc.

Property at 150 Old Farm Rd N, Chappaqua, NY 10514, 5 beds, 6 baths

$4,500,000

5 beds6 baths7,608 sq ft

150 Old Farm Rd N, Chappaqua, NY 10514

Listing by Julia B Fee Sothebys Int. Rlty

Based on information submitted to the MLS GRID as of Tue Sep 01 2026. 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.

Homes with Pools for Sale in Ossining

There are currently 17 homes with pools for sale in Ossining at a median listing price of $612K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Ossining stay on the market for 24 days and receive 12 offers. Popular neighborhoods include Sparta, Central Briarcliff West, and Scarborough. This map is refreshed with the newest listings in Ossining every 15 minutes.

In the past month, 14 homes have been sold in Ossining. In addition to houses in Ossining, there were also 13 condos, 2 townhouses, and 8 multi-family units for sale in Ossining last month. Ossining is a moderately walkable city in New York with a Walk Score of 63. Ossining is home to approximately 24,560 people and 6,377 jobs. Find your dream home in Ossining using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Ossining are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Ossining. Our Ossining real estate stats and trends will give you more information about home buying and selling trends in Ossining. If you're looking to sell your home in the Ossining area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Ossining with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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