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Homes for Sale with a Pool in Westchester, NY

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

$999,999
4 Beds 2 Baths 1027547 MLS
Welcome to your Dream home on a Huge .49 Acre of Level land. Resort Style Backyard with your own Private Swimming Pool- A BEAUTIFUL 4-bedrooms, DEN- (POSSIBLE 5th BEDROOM) 2 Full Bathrooms - This home offers perfectly blend timeless elegance, everyday comfort, and is a one of a kind - Well-maintained ranch-style residence, perfectly situated in a peaceful and highly desirable neighborhood . Offering the ease of one-level living with no interior steps, this exceptional home combines comfort, elegance, and functionality throughout. Designed with an open and inviting flow, the home features a spacious living room highlighted by a charming fireplace, a Huge formal dining room ideal for entertaining, and a beautifully updated eat-in kitchen appointed with granite countertops, stainless steel appliances, and ample cabinetry. The private primary suite offers a spacious retreat with 2 Spacious Walk-IN Closets complete with its own full bath, while three additional generously sized bedrooms and a Nicely, Updated Full Hall Jacuzzi bath. This Home offers plenty of room for family and Guests! Enjoy gathering in the warm and inviting Den or step outside to your own private backyard oasis—perfect for relaxing, outdoor dining, and entertaining. Well- maintained and move-in ready, this home offers the perfect blend of style, comfort, and convenience. Ideally located close to shopping, dining, parks, transportation, and all that the area has to offer, this is a rare opportunity to own a truly special home in a prime location. A must-see property that showcases pride of ownership throughout.

208 Woodhampton Drive, White Plains

$1,250,000
5 Beds 4 Baths 1023996 MLS
Perfectly perched in one of Mount Pleasant's most desirable neighborhoods, this extraordinary 5-bedroom, 4-bath Colonial commands breathtaking western horizon views and offers a rare double-lot setting that delivers the privacy, space, and resort-style lifestyle few homes can match. Every inch has been thoughtfully reimagined with exceptional craftsmanship, designer finishes, and uncompromising attention to detail, creating a residence where luxury and functionality exist in perfect harmony. A charming breezeway/mudroom provides seamless access to both the attached garage and the main home before unveiling an interior that is nothing short of spectacular. The sun-filled living room welcomes you with a classic brick wood-burning fireplace, oversized picture window, and warm, inviting atmosphere. A first-floor bedroom creates the perfect guest suite, au pair quarters, or home office. At the heart of the home is a showstopping chef's kitchen designed to impress. Outfitted with premium stainless steel appliances, sleek glass-front cabinetry, striking glass tile backsplash, endless quartz countertops, a generous extended island, farmhouse sink, and a garden window perfectly framing the stunning western views, this space is both sophisticated and functional. Designed with effortless flow, the open-concept layout seamlessly connects to the inviting living room and gracefully transitions to the elevated dining room, creating an exceptional backdrop for everyday living and unforgettable entertaining. Upstairs, the luxurious primary suite is a private retreat featuring an expansive walk-in closet, spa-inspired ensuite bath, and direct access to a private balcony where morning coffee and spectacular sunsets become part of your daily routine. Three additional spacious bedrooms and a beautifully updated hall bath complete the second level. The walk-out lower level elevates this home even further, offering incredible versatility with an expansive family/media room, an impressive summer kitchen, a designer full bath with an oversized walk-in shower, and direct access to the backyard. Whether hosting, entertaining guests, or creating the ultimate recreation space, the possibilities are endless. Occupying its own separate deeded lot, this private outdoor sanctuary is truly one of a kind. The heated saltwater in-ground pool is surrounded by premium paver patios, lush landscaping, and complete privacy behind secure fencing. A built-in barbecue, authentic pizza oven, and multiple entertaining spaces transform every gathering into a vacation-worthy experience, while unforgettable sunset views create a backdrop that feels worlds away from it all. Adding to its appeal, this exceptional home is designed for modern efficiency with leased, transferable solar panels and a state-of-the-art Mitsubishi high-efficiency mini-split heat pump system, delivering year-round comfort and impressive energy savings. Located within the award-winning Mount Pleasant School District, residents enjoy access to the town pools, library, parks, recreation, shopping, dining, major parkways, and Metro-North for an easy commute. This is more than a home, it's a lifestyle, a private retreat, and a rare opportunity to own one of Mount Pleasant's most exceptional properties.

121 Marietta Avenue, Hawthorne

$500,000
2 Beds 1 Baths 1015097 MLS
Set back from the road on a picturesque, tree-lined property, this inviting home welcomes you with classic charm, lush landscaping, and exceptional curb appeal. Step inside to a welcoming foyer that opens into a cozy living room featuring a wood-burning fireplace and a decorative wall niche, perfect for displaying treasured photos, artwork, or decor. Down the hall, you'll find two comfortable bedrooms, each offering generous closet space and endless possibilities to make them your own. The kitchen is equipped with stainless steel appliances and ample space to prepare your favorite meals. Just beyond, the formal dining room provides a warm setting for everyday meals and special gatherings while offering convenient access to the unfinished basement, complete with a laundry area and abundant room for storage, a home gym, workshop, or future expansion. Indirect hot water heater with lifetime tank warranty. Additionally, the attic offers approximately 700 square feet of storage space, providing plenty of room for seasonal items, holiday decorations, and other belongings. Off the dining room, a versatile den creates the perfect space for a home office, playroom, or cozy retreat. From the den, step outside onto the spacious back deck, ideal for outdoor dining, entertaining, or simply relaxing while overlooking the backyard. Follow the deck stairs down to your own private oasis, where a large above-ground pool provides the perfect place to cool off, host family and friends, or enjoy sunny afternoons all season long. This home includes a one-car detached garage and a spacious driveway offering ample off-street parking for multiple vehicles. Ideally located for commuters, the home is just 10 minutes from the Taconic State Parkway, only 5 minutes from the Bear Mountain State Parkway, and approximately 15 minutes from the Peekskill Metro-North train station, providing convenient access to surrounding towns and an easy commute to New York City.

77 Baron De Hirsch Road, Crompond

$1,650,000
3 Beds 4 Baths 1024567 MLS
Beautifully set on a level, fully usable 2-acre property in one of Armonk's most desirable locations, this exceptional home offers the perfect blend of privacy, modern updates, and everyday convenience. A rare second access from Creemer Road provides added flexibility and ease of entry. Designed for today's lifestyle, the home features an open-concept floor plan with hardwood floors, abundant natural light, and spacious living areas ideal for both everyday living and entertaining. The recently finished 1,384-square-foot walk-out lower level, complete with a full bath and direct outdoor access, provides exceptional additional living space perfect for a recreation room, home office, gym, guest suite, or media room. The private backyard is a true retreat, highlighted by an in-ground pool surrounded by expansive, level grounds with endless possibilities for recreation, gardening, or future enhancements. Extensive recent improvements include a new roof (2019), updated siding and gutters (2018), interior painting (2026), bathroom renovations (2025), new pool pump (2024), new pool filter (2025), 80-gallon hot water heater (2024), and a new electrical service panel (2023) wired for an EV charger. Additional features include central air conditioning, propane cooking, and a Special Features Sheet and survey available in the documents. Lives like 4 BRS. Enjoy the best of Armonk living, just minutes from the charming downtown village with its boutique shopping, acclaimed restaurants, cafes, parks, and year-round community events. Located within the highly acclaimed Byram Hills School District, this home also offers convenient access to the North White Plains Metro-North station with approximately a 48-minute express commute to Grand Central Terminal, as well as nearby Westchester County Airport and major parkways for effortless travel. Move-in ready and offering the ideal combination of space, location, and lifestyle—this is a rare opportunity to own a beautifully updated home in one of Northern Westchester's most sought-after communities. —don't miss it!

461 Bedford Road, Armonk

$2,137,500
4 Beds 6 Baths 1025674 MLS
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 owner to bring vision, updates and restoration to make it truly their own. Set on approximately 6.97 acres, the grounds are what make this offering so special: a private pond, mature trees, landscaped stonework, concrete pool, hot tub, cabana, open lawns, wooded surroundings and an extraordinary sense of seclusion. Additional improvements include a detached guest cottage situated above a three-car garage, plus a second three-car garage with a private pine-paneled retreat and a private meditation space with a stone fireplace, offering endless possibilities for guests, extended family, office, creative or recreational use. This is a property for someone who wants more than a house. It is for the buyer who wants a setting, a lifestyle and the chance to restore and personalize a truly special estate in one of Westchester’s most sought-after school districts. Rare, private and impossible to duplicate, 82 Shingle House Road is ready for its next chapter.

82 Shingle House Road, Millwood

$599,000
2 Beds 2 Baths 1025735 MLS
Privately set and beautifully maintained three-level end-unit townhouse in the highly desirable Chapel Hill community, offering comfort, functionality, and a private wooded setting<< PLUS $5,000 FLOORING ALLOWANCE >>The main level features an entry foyer, a dining area, and a beautiful living room highlighted by a fireplace, two remote-controlled skylights that fill the space with natural light, and sliding glass doors leading to a private 18' x 20' Trex deck overlooking the peaceful open space. The first floor also offers a spacious bedroom and a beautifully remodeled full bathroom (2022) with dual access from both the bedroom and hallway. Upstairs, you'll find a second bedroom with its own full bath, a walk-in closet, and a spacious loft area that provides excellent flexibility for a home office, den, guest space, or additional living area. The lower level offers even more usable space, additional storage opportunities, and access to the oversized one-car garage equipped with automatic door openers and built-in storage cabinets. A newer roof provides and freshly paved roads and driveway added peace of mind for the next owner. Wonderful Location! Residents of Chapel Hill enjoy access to exceptional community amenities, including a clubhouse, two swimming pools, tennis courts, pickleball courts, and a basketball court, making it one of the area's most sought-after neighborhoods. Combining a versatile layout, private setting, and outstanding community features, this home offers the perfect blend of comfort and convenience.

3501 Homestead Court, Peekskill

$1,100,000
3 Beds 4 Baths 1023729 MLS
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 (lives like a 4BR), 3 Full Bathrooms and one half bath, the bedroom level is just a few steps up from the sunny Main Level. You'll enjoy useful open spaces including: Large foyer, Eat-in-Kitchen, Dining Room, Office/Den, Living Room with Fireplace, open Great Room with high Cathedral Soaring Ceiling plus Sunroom/Greenhouse with sliders to outdoors - just steps to the private, tucked-away Pool area (refurbished in 2019). Down from the Main Level is a charming space with attached half bathroom, second fireplace and sunny window seat - ideal for a number of options: Guests, In-Law or Au Pair, Playroom/Gaming/Exercise/Office. And Still More Flex-Space! One more level features a large open room suitable for playroom/gaming/theater/exercise/office. Plus Sauna (like new, recently re-done), laundry, fantastic storage, shelving, closets and mechanicals. About 8 minutes to Scarborough Train Station for a 50 minute Scenic ride along the beautiful Hudson River to Grand Central Station. Close to the Village, Schools, Library, Village Pool, Camps, Tennis, Paddle, Pickleball and other Recreation; also close to the Hudson River, Rockefeller State Park, Championship Golf, shopping, music, film and more. Briarcliff Manor Schools & Recreation. Come see our changes before it's gone!

120 Cedar Drive E, Briarcliff Manor

$2,295,000
3 Beds 5 Baths 1018990 MLS
Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz Lange engaged noted designer Jonathan Adler to appoint the interior. The chef's kitchen features all Viking appliances, custom cabinetry, marble countertops, a center island with breakfast bar, and provides easy access to the outdoor terrace—ideal for everyday living and entertaining. Expansive, level lawns lead to hidden walking trails at the rear of the property, while a private in-ground pool and cabana create a peaceful outdoor retreat. This home is brimming with charm and distinctive character throughout. Additional highlights include a formal dining room, an elegant living room with a fireplace and custom built-ins, a sweet sunroom, and a versatile den/home office. The second-floor features three beautifully appointed bedrooms, an additional office, and a spacious primary suite with an ensuite bath. Professionally landscaped grounds enhance the property's setting, offering a peaceful and picturesque backdrop. Conveniently located just minutes from the Villages of Katonah and Ridgefield, with easy access to major commuting arteries. This home is located within the award-winning Katonah-Lewisboro School District. This is one you won't want to miss!

137 Boway Road, South Salem

$4,999,000
6 Beds 9 Baths 1022813 MLS
Beyond a tree-lined private drive and sweeping circular motor court lies one of Purchase Estates' most exceptional residences. Privately set on 2.16 exquisitely landscaped acres, this stately brick Colonial offers timeless architecture, exceptional privacy, and commanding curb appeal. A dramatic two-story foyer with a sweeping staircase introduces interiors of remarkable scale, refined craftsmanship, soaring ceilings, elegant millwork, and beautifully proportioned rooms. Designed for both grand entertaining and everyday living, the first floor features a sunken formal living room with fireplace, an elegant library/study with custom built-ins and wet bar, an oversized formal dining room with butler's pantry, and a spectacular chef's kitchen with professional-grade appliances, abundant custom cabinetry, oversized center island, and spacious breakfast room. French doors from both the breakfast room and dramatic family room with floor-to-ceiling stone fireplace open to the expansive slate patio, creating seamless indoor-outdoor living. A private guest suite with private patio access, oversized laundry room, mudroom, and service entrance complete the main level. The luxurious primary suite is a true retreat featuring a sitting room with custom built-ins and coffee bar, tray ceiling, gas fireplace, dual custom walk-in closets, and a spa-inspired bath with Jacuzzi tub, oversized shower, and dual vanities. Four additional ensuite bedrooms, each with a walk-in closet, an upstairs library/playroom, and a rear staircase complete the second floor. The walk-out lower level offers a finished storage of a recreation room with kitchenette, fitness room, abundant storage, and expansive unfinished space ready for a wine cellar, golf simulator, home theater, wellness retreat, or additional entertaining space. The spectacular grounds are among the finest in Purchase Estates. Beautifully level and impeccably landscaped, the resort-style backyard features a stunning pool, expansive slate patio, sprawling lawns, and mature specimen trees, creating the perfect setting for everyday enjoyment or grand-scale entertaining. Rarely does a property offer this level of privacy, beauty, and usable outdoor space. Ideally located just minutes from country clubs, golf courses, award-winning schools, and major parkways, this extraordinary estate offers a rare opportunity to own one of Purchase's premier luxury residences.

12 Magnolia Drive, Purchase

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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.