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

$1,950,000

5 Beds ⋅ 4 Baths ⋅ 1039863 MLS

Stunning new construction in a private, exclusive Somers community. This beautifully reimagined and expansive home features 5 bedrooms, 3 full baths, and 1 half bath on the main level. The fifth bedroom also offers flexibility as a second-floor media room or family room. With 4,425 square feet of living space, this home also includes a walkout unfinished basement with rough plumbing already in place for a future fourth full bathroom, offering exceptional expansion potential. Set on a private 1.6-acre lot, the property is perfect for outdoor entertaining and peaceful backyard gatherings. It also comes with approvals in place for a future in-ground pool, making it easy to create your own private retreat. Currently under construction, this is a rare opportunity to envision and customize your dream home in an exceptional setting. Conveniently located close to schools, shopping, and fine dining, and just 10 minutes from Metro-North.

5 Boulder Pond Drive, Somers

$2,200,000

7 Beds ⋅ 7 Baths ⋅ 1039583 MLS

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 overlooking the grounds. A 2026 spacious chef’s kitchen with center island and adjoining butler’s pantry is equally suited to everyday living and entertaining. The private quarters offer remarkable flexibility. The spacious primary suite enjoys elevated views toward the lake, while additional bedrooms accommodate family and guests. A dedicated home office and private theater provide exceptional work-from-home and leisure spaces, and the uppermost level offers two expansive rooms ideal for additional bedrooms, studios or creative space. Beyond the main residence, an impressive five-car garage connects by breezeway to the stable complex. A completely remodeled one-bedroom apartment above the stable wing and a separate two-bedroom stone cottage create exceptional possibilities for guests, extended family, private offices or independent living. With nearly 18 acres of landscaped grounds, mature trees, nature paths, substantial level lawn, pool, private lake, stonework and multiple outbuildings, Rose Lodge offers the increasingly rare opportunity to create a true private compound in the Lower Hudson Valley, combining the space and serenity of country living with convenient access to New York City.

83 Somerstown Road, Ossining

$895,000

4 Beds ⋅ 4 Baths ⋅ 1039790 MLS

BEAUTIFUL 4 BEDROOM COLONIAL WITH EXTENSIVE UPDATES THROUGHOUT! This well maintained 4 bedroom colonial offers numerous recent upgrades and modern amenities. The home features new windows with a transferable lifetime warranty, a fully renovated open concept first floor with an amazing Island, and fresh interior paint throughout the entire home, completed within the last year. Major mechanical improvements include a 10 year old boiler, new above ground oil tank, updated first floor electrical, a new electric panel with generator hookup and water storage tank that has never been used. The home also includes a propane range for cooking convenience. Additional living space can be found in the renovated basement, while all three bedrooms have been tastefully updated. Outdoor features include a newly fenced and private backyard, a renovated covered deck, screened gutters and a fireplace for added comfort and charm. Move in ready and thoughtfully updated, this home combines classic colonial style with modern improvements and exceptional value!

3123 Douglas Drive, Yorktown Heights

$999,000

7 Beds ⋅ 4 Baths ⋅ 1039591 MLS

A fantastic opportunity to own a versatile three-family property in the heart of Port Chester, offering an ideal setup for investors, owner-occupants, or multi-generational living. Situated on a desirable corner lot, this triplex features three separate units, with the third unit spanning the top two floors and offering a spacious multi-level layout. The property offers multiple porches and a patio, creating plenty of space to enjoy the outdoors, while the above-ground pool adds another great spot for relaxing and entertaining. A detached two-car garage provides additional parking and storage. Conveniently located close to the Port Chester Metro-North station, as well as shopping, dining, and local amenities, this property combines flexibility, outdoor space, and a commuter-friendly location in one exceptional opportunity!

318 William Street, Port Chester

$1,350,000

4 Beds ⋅ 3 Baths ⋅ 1037289 MLS

Welcome to 50 Sabbath Day Hill Road, a warm and inviting Colonial with contemporary flair, beautifully set on more than two private acres in desirable South Salem. Thoughtfully updated inside and out, this home offers a wonderful combination of timeless character, modern finishes and comfortable everyday living. The updated exterior creates an impressive first impression and introduces a home that has been carefully enhanced throughout. Inside, the beautifully renovated kitchen is the heart of the home, featuring rich and stylish cabinetry, quartz countertops, high-end appliances and abundant workspace and storage. The kitchen flows seamlessly into the spacious family room, where a striking stone-and-wood fireplace is framed by dramatic floor-to-ceiling windows, filling the room with natural light and bringing the outdoors in. The main level continues with an elegant formal dining room, gracious living room and a versatile den ideal for a home office, library or quiet retreat. An updated powder room and convenient mud/laundry room complete the first floor. Upstairs, a distinctive bridge-style hallway leads to the serene primary suite, featuring a beautifully renovated bath finished with quality materials and sophisticated details. Three additional bedrooms share an equally impressive updated hall bath, providing plenty of space for you and your guests. Updated interior finishes throughout give the home a fresh, move-in-ready feel while preserving its warmth and character. The outdoor setting is truly special. More than two acres of professionally landscaped grounds provide privacy, recreation and room to entertain. A tiered deck overlooks the property and leads to a beautifully fenced in-ground pool and gazebo—creating the perfect setting for summer gatherings, outdoor dining or simply relaxing at home. Perfectly located near Ridgefield, Bedford and the many wonderful surrounding communities, this South Salem setting offers an ideal combination of privacy, convenience and access to shopping, dining, recreation and everything the area has to offer. With its updated exterior, renovated kitchen and baths, refreshed interiors, wonderful floor plan and exceptional outdoor amenities, 50 Sabbath Day Hill Road offers the space, style and setting today’s buyers are looking for. A special South Salem home ready to be enjoyed.

50 Sabbath Day Hill Road, South Salem

$2,950,000

5 Beds ⋅ 6 Baths ⋅ 1031026 MLS

Meticulously maintained by its original owners and available for the first time, this brick Colonial combines elegant interiors, an exceptional floor plan, and outstanding outdoor living in the desirable Park Lane Reserve community, ideally located in West Harrison. A stone walkway leads to the grand covered portico and double front doors, opening to a classic home with quality finishes throughout. The triple-height foyer creates an impressive first impression with a sweeping curved staircase and dramatic chandelier. Formal living and dining rooms filled with natural light flank the entrance, with the dining room leading through a well-appointed butler's pantry to the chef's kitchen. Custom Mauser cabinetry, premium integrated appliances, a generous center island, and a sun-filled breakfast nook overlooking the backyard create an inviting and functional kitchen space. The adjoining family room, with its wood-burning fireplace and soaring ceilings, opens directly from the kitchen, while a private home office, full bath, mudroom, laundry, and powder room complete the main level. The second level is centered around a spacious primary suite entered through its own private vestibule. A sunny sitting room overlooking the backyard, a wall of windows, three walk-in closets, linen closet with built in hamper, and a spacious spa-inspired bath create a private and beautifully appointed suite. An additional ensuite bedroom, two further bedrooms sharing a generous hall bath, and a private king size guest suite with its own ensuite bathroom provide comfortable accommodation for family and guests. Set on level, professionally landscaped grounds, the outdoor amenities truly set this home apart. The backyard is designed around a heated PebbleTec pool and spa, with an expansive stone terrace, fully equipped outdoor kitchen, and broad, level lawn framed by professionally landscaped gardens. With its tree-lined streets and generously sized properties, Park Lane Reserve residents enjoy access to a private clubhouse with a fitness center, billiards room, banquet space, and seasonal swimming pool, fostering a welcoming sense of community. Updated with modern systems and conveniences, this home is truly move-in ready. Ideally located in one of West Harrison’s most coveted neighborhoods, it combines the tranquility of suburban living with convenient access to White Plains, major parkways, Westchester County Airport, and New York City.

48 Stonewall Circle, West Harrison

$839,000

3 Beds ⋅ 3 Baths ⋅ 1038194 MLS

Welcome to 61 Ganung Drive, a spacious 3-bedroom, 3-bath home situated on .65 acres in the Town of Ossining. Offering privacy, versatility, and exceptional outdoor living, this property has so much to offer. Step inside to a welcoming sunken living room with skylights and a dining room featuring a wood-burning fireplace, filling the space with natural light while creating a warm and inviting atmosphere. The downstairs offers additional living space with its own private entrance, full bath, living room, office, and wood-burning stove, making it ideal for a variety of uses. A Certificate of Occupancy is currently in progress for a possible fourth bedroom on the lower level, offering even more flexibility and potential. Central air adds comfort throughout the warmer months. The backyard is where this home truly shines. Ryder Park borders the rear of the property, creating a wonderfully private setting with no homes directly behind you. The fenced-in yard is designed for entertaining and everyday enjoyment, featuring a heated above-ground pool, two decks, gazebo, basketball court, and plenty of space to relax and gatherings. A newer shed, approximately four years old, provides additional outdoor storage. A two-car garage, cobblestone-lined half-moon driveway, and ample parking add to the home’s convenience. Enjoy your own private retreat while remaining conveniently located just 2 miles from the train station. With its spacious property, incredible outdoor entertaining areas, privacy, flexible living space, and commuter-friendly location, 61 Ganung Drive is a home that truly needs to be experienced.

61 Ganung Drive, Ossining

$949,000

3 Beds ⋅ 3 Baths ⋅ 1038981 MLS

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. This home offers tremendous value and proximity to multiple highways. Sitting on .75 acres, featuring a patio (with shower) and inground pool, which can easily become your ultimate summer oasis. Bring your own style, color palette and finishes to transform this wonderful space into your dream home. High potential property with affordable Mt. Pleasant taxes and Briarcliff Manor Schools.

107 Stephenson Terrace, Briarcliff Manor

$1,295,000

5 Beds ⋅ 3 Baths ⋅ 1038924 MLS

Welcome to 120 Harrison Avenue, a meticulously maintained legal 2-family home (5-bedrooms/3-bathrooms) offering an ideal combination of comfort, flexibility, and investment potential. Perfect for an owner-occupant, multi-generational living, or investor, this property offers a ton of versatility. The home features a private pool, a custom paver driveway providing ample off-street parking, and ductless heating and cooling throughout. The finished basement with a full bathroom provides additional living, recreation, office, or guest space. Energy-conscious buyers will appreciate the LG 370W solar panels, which help keep electricity costs remarkably low while providing long-term energy savings. The property offers prime location, with convenient access to I-87/New York State Thruway, Saw Mill River Parkway, Cross County Parkway, Bronx River Parkway, Sprain Brook Parkway, and Hutchinson River Parkway. Commuters will also appreciate nearby Metro-North service at Yonkers Station, providing convenient access to Manhattan and Grand Central Terminal. Shopping, dining, and entertainment are easily accessible, including Ridge Hill and Central Park Avenue. 120 Harrison Avenue is an exceptional opportunity for both homeowners and investors. This property is not to be missed!

120 Harrison Avenue, Yonkers

$4,400,000

8 Beds ⋅ 8 Baths ⋅ 1031136 MLS

A truly rare opportunity in Rye. Set on nearly 5 spectacular, estate-like acres in the Rye City School District, this is one of those properties that simply cannot be replicated today. The breathtaking grounds create a private retreat complete with an in-ground pool, expansive lawns, mature landscaping, and endless space to entertain, relax, or play. At the heart of the outdoor experience is an exceptional pool house that lives like a true second home—a pristine, newer residence featuring approximately 1,600+ square feet, three bedrooms, three full baths, a beautiful modern kitchen, spacious living area with fireplace, and covered patio overlooking the pool. Whether used for extended family, guests, an au pair, home office, or multigenerational living, it is a remarkable amenity rarely found at this level. The stately Colonial offers nearly 5,000 square feet with an outstanding floor plan, generous room sizes, sun-filled living spaces, a grand foyer, formal living and dining rooms, private office, spacious family room with stone fireplace and wet bar, sunroom, and five bedrooms including a gracious primary suite. The home has been meticulously maintained and presents the perfect opportunity to update and customize to your own style while preserving its exceptional layout and timeless character. An added bonus—and a major value enhancement—is the property's new connection to public sewer, eliminating one of the biggest concerns associated with estate properties while providing long-term peace of mind. Just minutes from downtown Rye, beaches, parks, marinas, restaurants, Metro-North, and award-winning Rye City Schools, this is a once-in-a-generation opportunity to own an estate-sized property with a true second residence in one of Westchester's most sought-after communities. Properties offering this combination of acreage, privacy, flexibility, and location are extraordinarily rare.

415 Grace Church Street, Rye

$900,000

3 Beds ⋅ 2 Baths ⋅ 1037965 MLS

Welcome to this beautifully renovated 3-bedroom, 2-bathroom classic home in the desirable Gedney Park neighborhood of White Plains. Thoughtfully updated throughout while preserving its timeless character, this charming residence offers a wonderful blend of old-world appeal and modern luxury. As you enter, you’re greeted by a warm and inviting living room featuring a brick-faced fireplace and beautiful bay windows that fill the space with natural light. The dining area flows seamlessly into the kitchen, creating an ideal layout for everyday living and entertaining, with convenient access to the side yard. The home features recessed lighting throughout, three bedrooms, and two full bathrooms. A main-level bedroom and full bathroom provide exceptional convenience for guests, or one-level living. Upstairs, two additional bedrooms share a luxurious full bathroom featuring a top-of-the-line Woodbridge soaking jet tub with skylight above, Kohler toilet, and Lutron light switches—thoughtful details that elevate everyday living. The basement offers even more possibilities, with a separate laundry room and an NTI on-demand heating and cooling system, providing efficient comfort throughout the home while offering valuable additional space for storage, hobbies, or future use. Step outside and discover your own backyard haven. A beautiful stone patio with fire pit sits across from the above-ground pool, creating the perfect setting for summer entertaining, relaxing evenings, and memorable gatherings. Enjoy the peaceful surroundings as the sounds of birds chirping create a tranquil backdrop. The expansive front porch offers yet another inviting space to relax and take in the charm of this beautiful property. Truly a special home that has been renovated with care and is ready to be enjoyed.

26 Gedney Terrace, White Plains

$1,749,000

4 Beds ⋅ 4 Baths ⋅ 1037920 MLS

Welcome to this spacious contemporary home offering 3,562 square feet of living space, beautifully situated on 1 acre in Harrison. This light-filled four bedroom and three-and a half bath residence offers generously proportioned living spaces and a wonderful flowing layout designed for both comfortable everyday living and entertaining. The private bedroom wing features four generously sized bedrooms, including a spacious primary suite with an en-suite bath, Juliet balcony and ample closet space. Outdoors, the property becomes a private retreat with an in-ground swimming pool surrounded by mature landscaping—perfect for summer entertaining, relaxing poolside, or enjoying time with family and friends. A wonderful opportunity to make this exceptional home your own.

444 West Street, Harrison

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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.