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

$15,000,000

5 Beds ⋅ 6 Baths ⋅ 1007263 MLS

EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

164 Eastwoods Road, Pound Ridge

$5,850,000

6 Beds ⋅ 8 Baths ⋅ 1002371 MLS

Set majestically on nearly three gated acres in Armonk’s coveted Wrights Mill Estates, this extraordinary hand-cut stone manor with over 12,000 sq ft of classic architecture, artisan craftsmanship, and resort-caliber living. A breathtaking foyer leads to the two-story great room with an impressive window wall and fireplace. A richly paneled study and sunlit conservatory offer space for dual home offices. A family room, dining room, chef’s kitchen with pantry and breakfast room, complete the main level. The upper level offers a grand primary suite, a luxurious retreat featuring a fireplace, dual spa baths, separate dressing rooms, and a third-floor private wellness space with sauna. Additionally, upstairs, four ensuite bedrooms, laundry room and den are joined by a dramatic enclosed bridge leading to a private guest wing. The lower level rivals a private club with lounge, wet bar, wine cellar, theater, gym, hot yoga studio, bedroom, bath and second laundry. Outdoor amenities are designed for both relaxation and entertaining, featuring a beautifully integrated pool, an independent spa, expansive terraces and patios and a built-in outdoor grill. The flat, beautifully manicured grounds are complemented by an elegant courtyard with eight garage bays providing generous space for prized automobiles and collections alike. Combining timeless-inspired grandeur with modern luxury, this remarkable estate presents a rare opportunity to enjoy a private country-club lifestyle just minutes from downtown Armonk and Greenwich, with convenient access to New York City. A truly exceptional opportunity for the most discerning buyer.

9 Terrace Circle, Armonk

$1,320,000

4 Beds ⋅ 4 Baths ⋅ 1008632 MLS

Welcome home to this lovely Colonial located in the highly desirable Thornwood section of Westchester County! Situated on an oversized, level corner lot of more than 10,000 square feet, this beautifully maintained home offers the perfect blend of space, comfort, and functionality. Step through the new front entry door into a bright and inviting first floor featuring a formal living room with new LED recessed lighting, custom blinds, and hardwood floors. The updated eat-in kitchen is designed for both everyday living and entertaining, showcasing dark cherry wood cabinetry, all-new stainless steel appliances, and ample counter space. The main level also includes a formal dining room, spacious den, convenient powder room, and a first-floor bedroom. Sliding door access leads directly to the backyard oasis. The second level features a large primary suite complete with a private en-suite bathroom, along with two generously sized guest bedrooms offering abundant closet space. Hardwood floors continue throughout the home, and the walk-up attic provides excellent storage or future expansion possibilities. The fully finished walk-out basement adds valuable living space and includes a brand-new full bathroom, making it ideal for a family room, home office, recreation area, or extended living arrangement. Additional highlights include a new washer and dryer, new hot water heater, and plenty of storage. Step outside and enjoy your own private backyard retreat featuring brick paver patios, a gazebo, multiple seating and entertaining areas, an above-ground pool for summer enjoyment, and a storage shed and lawn sprinkler system. Conveniently located near major highways, shopping, restaurants, parks, and transportation, this move-in-ready home offers everything today’s buyers are looking for. Don’t miss this exceptional opportunity to own a beautiful home in one of Westchester County’s most sought-after communities!

185 Jefferson Avenue, Thornwood

$1,198,000

3 Beds ⋅ 3 Baths ⋅ 1007115 MLS

Nestled on two private acres, The Owl’s Nest is a striking 3-bedroom, 2-bath mid-century modern chalet that blends architectural character, privacy, and modern convenience. Surrounded by nature, the home feels like a secluded retreat while remaining easily accessible to nearby towns and commuting routes. The heart of the home is a dramatic living room with soaring 18-foot ceilings and wall-to-wall windows that flood the space with natural light and bring the outdoors in. Warm wood tones, clean lines, and custom doors reflect the timeless appeal of mid-century design, while wraparound, treehouse-like decks create a seamless indoor-outdoor living experience. Outside, the property features a pool, landscape lighting, and a traditional wood-fired sauna, creating a private oasis perfect for entertaining or quiet evenings under the stars. The home also includes upgraded systems throughout, including a modern boiler, water pump, smart home controls, and a full-house Kohler generator for year-round peace of mind. Conveniently located with easy access to the Merritt Parkway and Interstate 684, The Owl’s Nest is just 15 minutes from the train station in Stamford, with additional nearby access in Mount Kisco and Bedford Hills for convenient travel to New York City and beyond. More than a home, The Owl’s Nest is a private sanctuary with timeless design, modern comforts, and an extraordinary connection to nature.

380 Long Ridge Road, Pound Ridge

$895,000

5 Beds ⋅ 4 Baths ⋅ 1005890 MLS

Welcome to 90 Timberlane Court! Make this lovely home with a legal two-bedroom accessory apartment yours. 90 Timberlane Court sits perfectly at the end of a quiet, private cul-de-sac, and can be the home of your dreams! This raised ranch contemporary has plenty of living space with a total of 5 bedrooms, 3 in the main part of the home plus another two bedrooms in a roomy accessory apartment. The bright and airy main living room has a soaring ceiling and wood burning stove. Plus, there is a cozy family room with fireplace for casual gathering. The dining room (with sliders to the spacious deck) opens to a well-appointed kitchen. Head upstairs and behind mirrored bi-fold doors is the perfect office space. The spacious primary bedroom has an en suite bath and large walk-in closet. Two bedrooms and a large hall bath complete the upstairs. The expansive outdoor deck and private yard with above ground pool are the perfect features for entertaining or private enjoyment. The property offers plenty of tranquil forest views as it borders acres of town land. Summer fun is waiting for you! The accessory apartment has its own entrance from the driveway and has a full eat in kitchen, living room, two bedrooms and full bath...perfect for extra living space! Major updates include a new roof and new vertical siding. This home has both great curb appeal and infinite interior possibilities. The front and side of the home have an irrigation system, and the yard has an electric pet fence system in place. There is a hook up for a portable full house plus accessory apartment generator. 90 Timberlane is convenient to all...shopping, major highways, entertainment and cultural events. This home is in "ready to move in" condition and waiting for you!

90 Timberlane Court, Yorktown Heights

$1,746,000

5 Beds ⋅ 5 Baths ⋅ 1007480 MLS

Spacious contemporary single-family residence situated on approximately 1.5 acres in Dobbs Ferry. This property offers approximately 4,120 sq ft of living space with 10 total rooms, including 5 bedrooms and 5 bathrooms. Features include an attached 1-car garage and expansive grounds providing potential for outdoor enhancements. The home is currently vacant and presents an opportunity for renovation and customization. Convenient location with access to local amenities, transportation, and major roadways. Property is being sold as-is. Buyer to perform all due diligence

200 Judson Avenue, Dobbs Ferry

$899,000

6 Beds ⋅ 4 Baths ⋅ 1007027 MLS

Welcome to 138 Arthur Avenue, a rare opportunity in the heart of Thornwood offering flexibility, space, and tremendous upside potential in one of Westchester County's most desirable communities. Lovingly maintained and cared for by the same family for more than 40 years, this is the type of property that buyers wait for. While the home offers tremendous value as it stands today, it also presents an exciting opportunity for a new owner to add their own personal touches and create something truly special. One of the most unique features of the property is its versatile layout, offering two distinct living areas that create an ideal setup for multigenerational living. Whether accommodating extended family, creating private guest quarters, or simply enjoying additional flexibility, the layout provides options that are increasingly difficult to find in today's market. The home also benefits from separate central air systems serving the different living areas, providing comfort and functionality throughout. For buyers with vision, there may also be an opportunity to explore conversion to a legal multifamily property, subject to approvals and requirements through the local municipality. Buyers are encouraged to conduct their own due diligence regarding future use possibilities, but the potential exists for those willing to navigate the process. Outside, your private backyard oasis awaits. The saltwater pool creates the perfect setting for summer entertaining, family gatherings, and relaxing weekends at home. Combined with the spacious outdoor areas, this is a property designed to be enjoyed both inside and out. What makes this opportunity especially compelling is the balance between current value and future potential. The home has been exceptionally maintained, yet there remains room for cosmetic updates and personalization that could significantly enhance both enjoyment and long-term value. For the buyer who can see beyond paint colors and finishes, this property offers the chance to unlock substantial equity through thoughtful improvements while benefiting from a location that continues to see strong demand. Situated in the highly sought-after Mount Pleasant community, you'll enjoy easy access to shopping, dining, parks, recreation, major highways, Metro North transportation options, and everything that makes Westchester County one of the most desirable places to live in the region. Whether you're searching for a multigenerational living solution, a property with future income potential, or simply a well-built home with outstanding upside, 138 Arthur Avenue delivers a combination of flexibility, location, and opportunity that is rarely available. Bring your vision, make it your own, and don't miss the opportunity to secure a property with exceptional long-term potential in one of Westchester's most desirable communities.

138 Arthur Avenue, Thornwood

$1,025,000

3 Beds ⋅ 3 Baths ⋅ 997307 MLS

Private access to the scenic North County Trailway, offering miles of paved trails for walking, running, and biking, is just one of the many highlights of this beautifully maintained home. Not to be missed, this sun-filled 3-bedroom, 3-bath raised ranch offers a comfortable layout ideal for both everyday living and entertaining. Set privately on over 1.3 level acres and screened from the road by a row of mature trees, the property provides exceptional privacy and a peaceful setting. Enjoy summers by the in-ground pool, a spacious backyard perfect for play and gatherings, and the convenience of a 2-car garage. Ideally located in the heart of Millwood, close to shopping, restaurants, and major parkways and in Chappaqua Schools, this home offers the perfect balance of privacy, recreation, and convenience. New AC!

568 Saw Mill River Road, Millwood

$4,595,000

7 Beds ⋅ 9 Baths ⋅ 956753 MLS

A charming bucolic retreat just moments from the city, 15 Sarosca Farm Lane is privately set at the end of a tree-lined lane on 5.89 spectacular acres. Rich in character and historic architectural detail, this 7-bedroom, 9-bath home offers a rare combination of privacy, scale, and resort-like amenities, including a sweeping driveway, tree house, tennis court, in-ground pool, half basketball court, vegetable garden, apple orchard, and a stone tower once used to supply water to the home. Inside, the 9,549-square-foot residence is designed for both gracious entertaining and everyday living, with an expansive eat-in chef’s kitchen, formal dining room, seven fireplaces, and a four-season room opening to an adjacent patio. The home also features a built-in barbecue, generous mudroom with laundry, upstairs recreation room, six en-suite bedrooms, gardener’s potting room, artist’s nook, and lower-level sporting storage. A detached heated 3-car garage and 1,040-square-foot gym further elevate the offering. A private oasis unto itself, the upstairs primary suite includes two walk-in closets, two bathrooms, and a large office. A rare and remarkable offering in Purchase, not to be missed.

15 Sarosca Farm Lane, Purchase

$999,000

6 Beds ⋅ 5 Baths ⋅ 1006585 MLS

Lovingly owned by the same family for more than 30 years, 26 Glen Avenue is a rare Port Chester offering that blends original warmth with exceptional space, versatility, and outdoor living. This expansive 6-bedroom home features 3 full bathrooms and 2 half bathrooms, along with over 3,000 square feet of living space that includes multiple bonus rooms ideal for today’s needs—home offices, workout areas, creative studios, or flexible recreation spaces. The bright, flowing layout provides practical everyday living with room to grow, refresh, or personalize over time. Natural light highlights the home’s timeless character, while the generous floor plan easily accommodates multi-generational living or anyone seeking abundant space in a central location. The outdoor setting is a true private oasis. A patio and deck highlight the in-ground swimming pool, creating a resort-like environment perfect for summer gatherings, entertaining, or quiet relaxation. The property also includes a detached 2-car garage and a driveway that accommodates up to 5 additional vehicles, offering exceptional parking and storage—an uncommon convenience in this area. Ideally situated just half a mile from the Port Chester Metro-North Station, the home provides quick access to NYC and the region. You’re moments from the village’s vibrant dining scene, shopping, entertainment, and all the amenities that make Port Chester such a dynamic and convenient place to live. With its combination of size, location, and decades of thoughtful ownership, 26 Glen Avenue is a well-loved residence and a wonderful opportunity for buyers seeking a spacious home to enjoy now and update over time. This is one you’ll want to experience in person.

26 Glen Avenue, Port Chester

$725,000

3 Beds ⋅ 2 Baths ⋅ 1000807 MLS

Welcome to this charming Colonial nestled on a quiet cul-de-sac enclave, offering privacy, convenience, and exceptional value in a highly desirable New Rochelle location. Featuring 3 bedrooms, 2 bathrooms, and flexible living spaces throughout, this home is designed for both comfort and functionality. The main living areas flow seamlessly, complemented by a finished basement ideal for recreation, a home gym, or extended living. A dedicated office/den/flex space on the main floor provides the perfect solution for today’s lifestyle needs—whether working from home, hosting guests, or creating a playroom. The updated kitchen (April 2020) is thoughtfully designed with practical upgrades, including deep cabinet storage, a butcher block countertop , and a beautiful picture window inviting an abundance of natural light . The kitchen is perfect for maximizing both space and convenience. Step outside to your private backyard retreat—highlighted by an above-ground pool (new liner installed last summer) and a patio ideal for relaxing or entertaining. Notably, this is one of the only homes in the area with a pool, making it a rare find. The property also benefits from a unique rear setting backing up to a schoolyard, offering added privacy with no direct neighbors behind. Additional major updates include: Water heater (2025) with 6-year warranty. Windows (2017) plus updated front window and sliding glass doors (2020) with lifetime transferable warranty. Roof estimated under 10 years old. A one car garage completes the home’s functional features. Location truly sets this home apart—enjoy a walkable lifestyle with easy access to shopping, restaurants, parks, and recreation, including Glen Island Beach & Park, D’Onofrio Ballfield, Neptune Park, Davenport Park, and Eddie Foy Park, along with nearby yacht clubs and marinas. Commuters will appreciate the short drive to Metro-North and major highways, making this an ideal blend of suburban living and city accessibility. Taxes reflect STAR discount -

38 Emmett Terrace, New Rochelle

$1,750,000

9 Beds ⋅ 8 Baths ⋅ 1005133 MLS

Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining

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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.