Homes for Sale with a Pool in Westchester, NY

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Welcome to your dedicated resource for homes for sale with a pool in Westchester, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Westchester, NY agent, Tierra Stanback specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Westchester, NY

$2,790,000

6 Beds ⋅ 6 Baths ⋅ 1035591 MLS

An extraordinary original Myron Goldfinger commission, documented in the architect’s archive as the 1991 Leff Residence, Architecture in the Landscape #7. This exceptional 8,200-square-foot contemporary residence showcases Goldfinger’s signature geometric design, dramatic curved ceiling, sculptural floating staircase, and expansive walls of glass that connect the interiors to the surrounding landscape. Six bedrooms and five-and-a-half baths include an exceptional main-level primary suite, offering a private retreat with a spectacular boutique-style walk-in dressing room featuring multiple custom closets, thoughtfully designed storage, and dedicated display spaces for shoes, handbags, and accessories. A truly special luxury feature not to be missed. The updated kitchen respects the integrity of the original architecture. Resort-style amenities include a private pool with two built-in grills, fitness room, and private tennis court, plus a four-car attached garage. Set in a remarkably private wooded setting in the Chappaqua Central School District, including Horace Greeley High School, with approximately 50-minute Metro-North access to Manhattan. A rare opportunity to own a significant work of architecture where privacy, nature, and extraordinary design converge.

20 Bessel Lane, Chappaqua

$500,000

2 Beds ⋅ 3 Baths ⋅ 1052914 MLS

Set in the heart of a neighborly community, 3 Brooke Club Drive, Unit 4, is on the cusp of two great worlds. Just minutes from transportation, restaurants and schools, yet in its own private oasis on a non-thru street, surrounded by natural beauty, this is the home you have been looking for. Park in the large driveway, large enough for two vehicles, or the garage, which contains the updated mechanical systems of the home. Approach the front door through the gate and down the plant lined path, passing a quiet sitting area as you do. Entering the home, you will find an expansive living room, with windows looking out to the trees beyond. A wood-burning fireplace at the head of the living room is a perfect spot for the approaching fall months. Sliding doors in the dining area, which is wonderfully open to the living room, lead to a rear deck - a perfect place to sit and watch nature beyond. Turning around, find the the bright kitchen with plenty of counter space and updated cabinets that meet all of your storage dreams. Toward the back, a convenient laundry closet and beyond, the garage. Also on this level is the updated hall bathroom and a deep closet, which can hold many treasured items. Up the architecturally striking staircase, illuminated by shafts of light from a wall of windows, you will find a large loft space, suitable for an office, den or more. The cathedral ceiling here soars twelve fee above. Past the loft is the deep primary bedroom with extra closets and its own vaulted ceiling. The ensuite bathroom features a tiled bathtub, glass shower and skylight. Also on this floor is the bright second bedroom, with its own attached full bathroom. Beyond what is inside this wonderful home, we are just a short jaunt to the clubhouse, with a wonderful indoor pool and convenient gym. All of this, just three minutes to the Croton Harmon Train station and moments to downtown Ossining, with all of its shops and attractions. You are a stone's throw from the Hudson river and scenic trails and just fifty minutes from Grand Central Terminal. What more could you ask for?

3 Brooke Club Drive Unit #4, Ossining

$8,750,000

7 Beds ⋅ 9 Baths ⋅ 1048353 MLS

A truly exceptional Scarsdale estate where refined design, exceptional craftsmanship, and resort-style living come together on nearly one acre of beautifully landscaped grounds. Custom built by Healthy Home Builders and professionally designed by The Fox Group, this extraordinary residence offers 7 bedrooms, 7 full and 2 half bathrooms, 6,839 square feet of main living space, and an additional 2,503 square feet of finished lower level. Thoughtfully curated interiors feature 10-foot-plus ceilings, custom millwork, bespoke wallcoverings and carpets, four fireplaces, and an exceptional collection of finishes. The custom kitchen is appointed with Calacatta marble, Waterworks fixtures, Sub-Zero and Wolf appliances, and a beautifully designed butler’s pantry, while the primary suite offers de Gournay wallcovering, a gas fireplace, custom dressing rooms, and a spa-like bathroom. The fully finished lower level, designed by Smart Playrooms, offers an extraordinary collection of spaces for play, creativity, recreation, and relaxation. Whole-home amenities include two generators, premium water and air filtration, smart security, integrated audio, and a Tesla charging station. Outside, the property takes on a resort-like feel with a heated gunite pool and spa, Calacatta marble pool terrace, covered veranda, stone fire pit, custom playground, mature landscaping, and exceptional privacy. An extraordinary residence where sophisticated design, exceptional amenities, and seamless indoor-outdoor living create a truly elevated Scarsdale lifestyle.

27 Murray Hill Road, Scarsdale

$1,850,000

5 Beds ⋅ 4 Baths ⋅ 1053340 MLS

The home you've been waiting for has arrived! This charming and beautifully appointed renovated 1927 Dutch Colonial is located on one of the most sought-after streets in the Village of Croton-on-Hudson. Offering approximately 4,200 square feet of spacious living, this 5-bedroom, 3.5 bath home blends timeless character with inviting everyday living. A stunning wraparound covered front porch with a swing welcomes you home, while elegant French doors add classic architectural charm throughout. The private outdoor setting is equally impressive, featuring a beautiful in-groundpool, gardens, stone walls, a deck and plenty of space for entertaining and relaxing. A generous 3-car garage with an upper loft provides exceptional convenience and storage. A rare opportunity to own a substantial, character-filled home in a truly desirable Sunset Park neighborhood offering a walk-to-all lifestyle.

28 Observatory Drive, Croton-On-Hudson

$6,675,000

7 Beds ⋅ 10 Baths ⋅ 1052921 MLS

New Construction, this is the last available new home at exclusive "Sarosca Farm Estates" in Purchase. Built with the highest standards of quality & craftsmanship, this home has an open floor plan and features a gourmet kitchen with center island, coffee bar/butlers pantry, family room with fireplace, living room, home office, guest bedroom with a full bath, mud room with custom built-ins, and a back staircase complete the main level. The second floor has an incredible primary suite with a vaulted ceiling, fireplace, slider to a terrace with breathtaking views of the grounds, spa like bath room, and 3 walk in custom closets. Four additional en-suite bedrooms and laundry room complete the second floor. The lower level is a finished open recreation area with high ceilings, can be custom finished to include a golf simulator room, theatre, gym, bedroom, or wine cellar. The private backyard is spectacular and includes a gunite pool, stone patio, and a covered porch with an outdoor fireplace, perfect for entertaining. Amenities include 10 ft ceiling on the 1st floor, dramatic large windows & sliders, sleek moldings, fixtures & hardware, spacious custom closets, high efficiency heating and cooling system, still time to customize this home and make it your own.

5 Stone Bridge Road, Purchase

$999,999

3 Beds ⋅ 3 Baths ⋅ 1051677 MLS

Welcome to this beautiful fully updated single family home on cul de sac in Yonkers, offering approximately 1,874 square feet of comfortable living space. The inviting main level features a full updated kitchen and dining area, perfect for everyday living and entertaining. Step outside to your private, fenced-in backyard oasis, complete with a sparkling pool with new liner, expansive stone paved entertaining area with fire pit & Gas outdoor BBQ on beautifully landscaped grounds—ideal for summer gatherings and outdoor enjoyment. Additional features include new boiler & hot water heater, Lovely basement and sub basement. Attached garage, stone paved driveway, and walkway that enhance the home’s curb appeal. A wonderful opportunity to own a spacious home with exceptional indoor and outdoor living spaces in a desirable Yonkers location.

43 Nimitz Place, Yonkers

$3,995,000

7 Beds ⋅ 10 Baths ⋅ 1044834 MLS

A rare opportunity to reimagine one of Harrison’s most distinctive estates. Set on 5.21 beautifully landscaped acres, this custom-built brick residence offers exceptional scale and complete privacy—all just minutes from downtown Rye, the Metro-North train station and major highways. Ideal for an end user with the vision and resources to renovate and maintain a true estate, the property may also present an intriguing opportunity for a builder or developer to explore redevelopment or subdivision potential, subject to municipal approvals and independent due diligence. Offering more than 10,000 square feet across the first and second floors not including the livable bouns space on third floor, plus an approximately 2,000-square-foot lower level, the home is centered around a dramatic front-to-back atrium with soaring ceilings, marble floors and walls of glass. The expansive first floor features formal living and dining rooms, a richly paneled library, chef’s kitchen with breakfast areas, spectacular great room with fireplace and wet bar, and a private two-bedroom guest wing. Upstairs, the palatial primary suite includes a fireplace, radiant-heated sunroom, two marble bathrooms, extensive fitted wardrobes and distant Long Island Sound views. Additional ensuite bedrooms, an office or optional bedroom, upper-level laundry and a third-floor guest or recreation suite offer exceptional flexibility. The lower level includes a full bowling alley, gym, wine cellar, workshop, additional bedroom suite and access to the attached seven-car garage. The resort-like grounds feature a heated infinity pool, pool house, separate guest house, full clay tennis court, indoor-outdoor Jacuzzi, expansive patios, rolling lawns and magnificent mature trees. An elevator, generator, multi-zone heating and air conditioning, heated driveway areas, security system and irrigation complete this truly one-of-a-kind Harrison estate.

7 Rockledge Road, Rye

$2,799,000

4 Beds ⋅ 5 Baths ⋅ 1042009 MLS

Privately set on over an acre overlooking picturesque Pocantico Lake, this distinctive four-bedroom contemporary residence offers an exceptional combination of privacy, natural beauty, and sophisticated living. The property is framed by lush lawns, established gardens, mature plantings, and protected parkland, with captivating water views enjoyed from multiple vantage points. The home’s design emphasizes light, volume, and a strong connection to the surrounding landscape. Floor-to-ceiling windows, clean architectural lines, natural finishes, and thoughtfully designed open spaces create a modern yet inviting atmosphere. The main level features gracious living and dining areas, three fireplaces, a well-appointed eat-in kitchen, and a comfortable family room that opens directly to a large rear terrace overlooking the lake. A spacious primary suite occupies the first floor and includes a private outdoor terrace and full bathroom. Three additional bedrooms, a flex room, and two full bathrooms are located upstairs, providing excellent separation between private and entertaining spaces. The walk-out lower level adds an entirely different dimension to the home, with an indoor swimming pool, sauna, wet bar, full bathroom, and office. Located in sought-after Pocantico Hills, the property offers a peaceful Hudson Valley lifestyle with easy access to the area’s many attractions. Rockefeller State Park Preserve is nearby, offering miles of scenic trails and carriage roads, while the villages of Tarrytown, Sleepy Hollow, and Pleasantville provide restaurants, shops, cultural destinations, and everyday conveniences. Metro-North service makes Manhattan accessible while the surrounding landscape provides a welcome sense of escape. With its remarkable waterfront setting, private grounds, exceptional recreation spaces, and convenient location, this is a truly uncommon opportunity to experience the best of modern country living in Pocantico Hills.

21 Kings Grant Way, Briarcliff Manor

$1,388,888

3 Beds ⋅ 3 Baths ⋅ 1044782 MLS

A Private Hudson Valley Retreat Where Luxury, Location & Lifestyle Come Together. Discover an exceptional hidden gem in coveted Briarcliff Manor, where timeless charm, sophisticated living, and an enviable Village location create a truly special place to make home. Tucked away on a quiet cul-de-sac, this beautifully well-loved residence offers the feel and flexibility of an estate while remaining just moments from the heart of the village. Set in the picturesque Hudson Valley and served by Briarcliff Manor’s highly regarded schools, this spacious home offers 2,736 square feet of thoughtfully designed living space, including 3 bedrooms, 3 full baths, bonus 1,000 sq ft finished lower-level, an attached 2-car garage, 20 X 40 inground pool and a legal accessory apartment above the garage. With town sewer and natural gas, the property combines everyday convenience with an extraordinary sense of privacy and retreat. The main level is designed for effortless living and entertaining, featuring an updated kitchen with granite countertops, custom cabinetry with soft-close doors, and island seating. A striking stone-accented wood-burning fireplace anchors the open-concept living spaces, while a sunken living room and walls of windows and glass sliders create a light-filled connection to the spectacular backyard. The main level also features a luxurious primary suite with a versatile sitting room, ideal as a private office, reading room, or tranquil retreat. A second bedroom and beautifully appointed Jack-and-Jill bath complete the level, with a spa-inspired Jacuzzi tub and dual sinks and toilets. The expansive walk-out lower level, offering more than 1,000 extra square feet, provides exceptional versatility and privacy. With its own private entrance, this level can easily accommodate an au pair or in-law suite, extended household, guest quarters, or an impressive entertainment and recreation space. Features include a den, dining area, summer-kitchen area, bonus guest room, full bath with tub, office, and a spectacular media room with cathedral ceilings, skylight, and direct access to the pool and backyard. An unfinished area provides additional storage, laundry, and mechanical space. Adding yet another layer of flexibility and value, the property includes an accessory apartment above the garage, complete with a living room, sleeping area, kitchen, and full bath with tub ideal for generating income or guest suite. Step outside and discover your own private backyard oasis with a mature landscape and gorgeous flowering magnolia tree. The flat, beautifully usable grounds and gunite pool create an idyllic setting for summer entertaining, relaxing poolside, and enjoying the best of outdoor living. The peaceful cul-de-sac setting enhances the feeling of privacy while keeping the village’s many amenities remarkably close at hand. And the location is truly exceptional. From this sought-after setting, it’s an easy stroll to the charming village center, with its shops, restaurants, library, town pool, tennis, North County Bike Path, and more. Scarborough Station is just a five-minute drive away, offering scenic Metro-North service along the Hudson River to New York City. Enjoy easy access to Rockefeller State Park Preserve, Trump National Golf Club Westchester, the Jacob Burns Film Center, Tarrytown Music Hall, cycling trails, restaurants, shopping, and premier Briarcliff Manor schools. A rare opportunity to enjoy the privacy and versatility of an estate-like retreat with the unparalleled convenience of village living. At 15 Tulip Road, the Hudson Valley lifestyle is yours to savor.

15 Tulip Road, Briarcliff Manor

$869,000

5 Beds ⋅ 2 Baths ⋅ 1024428 MLS

Total move-in condition meets architectural elegance in this beautifully expanded, fully renovated five-bedroom, two-bathroom home. The sophisticated main floor design showcases an oversized living room anchored by a sleek, see-through dual-sided fireplace that serves as an intelligent room divider. Flow effortlessly into the elegant formal dining room, comfortable family room, and a modern eat-in kitchen boasting a center island and granite countertops. Two spacious main-floor bedrooms and a beautifully updated bathroom offer great versatility for guests or main-level living. On the upper level, discover a sumptuous primary bedroom retreat complete with a walk-in closet and a Jack and Jill bathroom featuring a jacuzzi tub. Two additional large bedrooms offer great closet storage, while the oversized landing provides a massive bonus space that could easily be converted into a dedicated home office or a sixth bedroom. The exterior is a true extension of the home, featuring a large, level, and beautifully landscaped property. The fenced-in yard includes a wonderful patio perfect for entertaining and gardening, with more than enough room left over for a pool. Complete with a four-car driveway and eco-friendly solar panels, the property is situated in a quiet, tree-lined neighborhood just minutes from the Metro-North train for a quick commute to New York City, local restaurants, shopping, and schools.

4 Manitou Trail, White Plains

$1,995,000

4 Beds ⋅ 5 Baths ⋅ 1042303 MLS

Captivating North Salem Retreat. Enveloped by rolling emerald lawns, verdant tree canopy, masterful gardens, and a spectacular lagoon-style pool oasis - this special property is an enchanting botanical paradise. The main home showcases a compelling architectural design, rich with enduring charm. Floor-to-ceiling walls of glass flood the interiors with extraordinary natural light - framing breathtaking, panoramic views of the breathtaking property from every angle. Exquisite hardwood floors flow continuously throughout, opening into expansive, beautifully scaled living spaces - suitable for both grand entertaining and intimate living. The stunning chef’s kitchen features custom cabinetry, Taj Mahal countertops and a delightful eat-in area that opens to a serene back deck and balcony overlooking the sweeping meadows beyond. Anchored by a magnificent fieldstone fireplace, the living room flows seamlessly into an intimate den, offering a series of cozy spaces and quiet nooks to unwind. A showstopping home office/ library boasts soaring beamed cathedral ceilings and extraordinary custom built-ins. Upstairs, the primary bedroom suite offers incredible vista views, a custom bathroom with soaking tub, and a large dressing room. Across the hall, there is a full bath and spacious guest room. Downstairs, the fully-finished lower level offers a family room with stone fireplace, two guest bedrooms with two full baths, sauna, laundry, and french doors out to a stone patio. Tucked away in a sanctuary of mature plantings and deep greenery, the pool area delivers an unparalleled outdoor entertaining experience. A beautiful gunite lagoon pool and spa take center stage, paired seamlessly with an elegant pool house villa - complete with an outdoor grill area, indoor kitchen, living and dining spaces, a bathroom, a refreshing outdoor shower, and an attached greenhouse. Every detail crafted for bespoke country living. A rare gem in today’s market, this exceptional property offers a profound sense of peacefulness and is located in one of North Salem’s most desirable areas.

278 Hawley Road, North Salem

$5,750,000

6 Beds ⋅ 8 Baths ⋅ 1017994 MLS

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks a scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

24 Trails End, Chappaqua

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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.