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

$2,395,000

4 Beds ⋅ 5 Baths ⋅ 1019519 MLS

Welcome to this exceptional Colonial residence, perfectly situated on the iconic Esplanade—one of Pelham's most prestigious and sought-after addresses. Lined with elegant homes and mature trees, this distinguished street is celebrated for its timeless beauty, architectural character, and enduring appeal, making it one of the village's most coveted locations. As you step inside, the welcoming entrance foyer leads to a spacious living room with high ceilings and detailed crown molding, creating an inviting atmosphere for both everyday living and entertaining. The formal dining room provides the perfect setting for memorable gatherings, while the well-equipped eat-in kitchen offers abundant space for casual meals and daily life. Featuring a gas range, microwave, dishwasher, and dryer, it is thoughtfully designed for everyday convenience. On the second floor are four spacious bedrooms and four-and-a-half bathrooms, including an expansive primary suite with a private primary bathroom. On the third floor is a finished space currently being used as a lounge area and bedroom. The lower level also features a finished room with a fireplace, along with a gym in the garage area. Don't miss the opportunity to make this exceptional home your own.

514 Esplanade, Pelham

$785,000

4 Beds ⋅ 3 Baths ⋅ 1020457 MLS

Experience the advantages of newer construction, Welcome to 140 Winthrop Avenue! Built in 2017, this beautifully maintained 4-bedroom, 2.5-bath Colonial style home is a rare opportunity to own one of the area’s newer homes offering today’s most desirable features. Inside, nearly 2,000 square feet of thoughtfully designed above-grade living space features a bright, open layout, a beautiful kitchen with granite countertops, stainless steel appliances, and seamless flow into the dining and living areas—perfect for everyday living and entertaining. Upstairs, the spacious primary suite with custom built closet and private bath is joined by three additional generously sized bedrooms, a full bath and a fully loaded laundry room. Outside, enjoy a own private backyard retreat, featuring a fully fenced yard with an above-ground pool, spacious patio, built-in grilling area, and a children's playset—perfect for summer entertaining, outdoor dining, family gatherings, or simply unwinding at the end of the day. An attached garage adds everyday convenience and additional storage. Every square foot of this home is dedicated to finished, above-grade living space, creating an efficient floor plan designed for comfortable everyday living and easy maintenance. SCHEDULE YOUR SHOWING TODAY!

140 Winthrop Avenue, Elmsford

$2,600,000

4 Beds ⋅ 6 Baths ⋅ 1010978 MLS

Privately sited at the end of a cul-de-sac close to downtown Armonk, this modern residence is a masterful expression of design, scale, and light. Conceived for sophisticated living and exceptional entertaining, the residence showcases soaring 13-foot ceilings, grand open spaces, and dramatic walls of glass that create a seamless connection between the interior and its breathtaking natural surroundings.The home provides gallery-like interiors ideally suited for the display of fine art, while maintaining a warm and inviting atmosphere. Every room is thoughtfully proportioned and flooded with natural light, creating a sense of effortless elegance throughout. Resort-caliber amenities include a sparkling pool and spa, tennis court (needs restoration) and expansive outdoor spaces. Offering the tranquility of a secluded retreat with the convenience of a premier location, this exceptional property is just moments from town, schools, transportation, and all the amenities of refined suburban living.

6 Hunting Trail, Armonk

$3,100,000

3 Beds ⋅ 5 Baths ⋅ 1019351 MLS

No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and superior hardware throughout. The woods in the house are too numerous to list, but some of them are Mahogany, Red Maple, Pecky Cypress, White Oak, Utile (Mahogany type), Amboyna, Birch, Curly Birch, Bubinga, Red Birch, Maple, Maple Burl, and Walnut. All of the baseboards are double or triple layered with different wood species. All of the light fixtures, window dressings, and appliances stay with the home. The gourmet kitchen contains a steam oven, double drawer freezer full-size refrigerator, built in microwave, warming drawer, six burner stove, double oven, ice maker, separate built-in vacuum cleaning system. Additional square footage is on the basement level. This is a wonderful home surrounded by greenery to entertain guests or enjoy your privacy. Please see video link for a virtual tour.

23 Inningwood Road, Ossining

$7,995,000

6 Beds ⋅ 6 Baths ⋅ 1015115 MLS

Tucked away at the end of a long private drive, hidden from view and unknown to many who pass nearby, this extraordinary waterfront estate offers a rare combination of privacy, history, and lifestyle in one of Rye’s most coveted neighborhoods. Originally built in 1856 as part of the area’s original homestead and thoughtfully expanded and enhanced over the years, the property spans 1.59 spectacular acres along Milton Harbor with direct access to Long Island Sound. A world apart from the ordinary, the 5,233-square-foot residence is surrounded by breathtaking gardens, mature specimen plantings, and a series of enchanting outdoor spaces that unfold from one destination to the next. Multiple terraces invite al fresco dining and entertaining—from morning coffee overlooking the water, to sunset cocktails by the pool, to gatherings at the dock as boats return from a day on the Sound. With six bedrooms, five full and one half baths, four garage bays, a waterside pool, and a private dock accommodating a vessel up to approximately 32 feet, the property delivers an unrivaled waterfront lifestyle. The setting evokes a distinctive “Bedford meets the water” feel—an uncommon blend of estate-like grounds, privacy, and natural beauty rarely found on the shoreline. While the home enjoys all the benefits of the vibrant Hix Park neighborhood community, it lives as its own private sanctuary. This is not a cookie-cutter property. It is for the buyer seeking something truly unique: a place with history, character, extraordinary land, stunning gardens, a dock, pool, water access, and a sense of discovery that cannot be replicated.

87 Hix Avenue, Rye

$6,790,000

7 Beds ⋅ 9 Baths ⋅ 1005728 MLS

Cosseted within the gates of the exclusive Conyers Farm association with 24hr security, this baronial French Normandy chateau is poised on more than thirteen park-like acres. Hospitality sets the tone from the entrance through the grand foyer to the dual living rooms, an impressive formal dining room for large-scale entertaining and a warmly paneled library. The heart of the home is the luxurious kitchen with butler's pantry, breakfast room and adjoining family room with fireplace. French doors open to the immense terrace, perfect for outdoor dining. A true sanctuary, the primary suite features two bathrooms, two sizable walk-in closets, a dressing room and a romantic sitting room with balcony overlooking the naturally secluded, private backyard. Six additional bedrooms offer abundant space for guests or family. Creating captivating vignettes of multifunctional living, the lower level features a home theater, sitting room with fireplace, full bar with kitchenette, gym, indoor resistance pool and a hot tub. Outside the terrace overlooks beautiful, level lawns and a pool with spa. Peace of mind is the directive for this characterful estate, with its reassuring security in a guard-gated enclave and its luxury leisure amenities.

4 Cowdray Park Drive, Armonk

$775,000

4 Beds ⋅ 1 Baths ⋅ 1016615 MLS

Welcome to 29 Saint Joseph Street, New Rochelle — a beautifully maintained and spacious home nestled on a quiet dead-end street. Situated on an oversized double lot in a two-family zone, this property offers space, flexibility, and endless potential. Inside, enjoy a sun-filled layout featuring hardwood floors throughout, a spacious living room, formal dining room, and an eat-in kitchen perfect for everyday living and entertaining. The second floor offers four generously sized bedrooms, while the fully finished attic provides bonus space for a home office, gym, guest suite, or playroom. A walk-out partially finished basement adds even more versatility. Step outside to a private fenced backyard ideal for entertaining, featuring an above-ground pool sitting beautifully on a lush green lawn, an enormous driveway that comfortably fits four cars, an oversized three-car garage, and a charming front porch perfect for relaxing. Conveniently located minutes from major highways, shopping, dining, and the New Rochelle Metro-North Station with direct access to Grand Central in approximately 30–40 minutes. Enjoy nearby waterfront destinations including Glen Island Park, offering scenic views, walking paths, beaches, and vibrant outdoor recreation. Residents also benefit from easy access to renowned Michelin-star dining throughout Westchester and nearby Manhattan. Move-in ready and perfectly located — don’t miss this exceptional opportunity in the heart of New Rochelle! Note: Eligible for STAR program (New York State tax benefit that reduces the school tax portion of property taxes for eligible homeowners who use the home as their primary residence). Contact the Assessor’s Office to file a tax grievance.

29 Saint Joseph Street, New Rochelle

$1,199,000

4 Beds ⋅ 3 Baths ⋅ 1017839 MLS

Renovated 4-Bedroom, 3-Full-Bath Residence — Luxury Living & Entertaining. Welcome to this beautifully renovated home featuring four bedrooms and three full bathrooms. The expanded interior offers ample living space, including a living room with fireplace, a formal dining room, and a family room with an attached den—ideal for remote work. The chef-inspired kitchen showcases top-of-the-line Viking appliances, solid cherry cabinetry, granite countertops, and a large center island perfect for entertaining. Step through the new sliding glass door to your private oasis: a manicured, secluded backyard with mature fruit-bearing trees and a heated fiberglass in-ground pool—perfect for summer gatherings and relaxation. This home blends luxury, comfort, and convenience—ideal for entertaining and everyday living.

74 Elaine Terrace, Yonkers

$5,495,000

5 Beds ⋅ 7 Baths ⋅ 1010043 MLS

Rockridge is an extraordinary hilltop estate situated on one of the highest elevations in all of Bedford. Offering 25-mile panoramic vistas across The Hudson Valley to The Palisades of New York, the property is quite simply stunning. Gated, fenced, and accessed by a quarter-mile long driveway, the residence is perfectly sited on over 11 acres of spectacular rolling land. The house centers on a brand-new award winning Leicht kitchen. The great room with a massive stone fireplace is under an exposed beam and cathedral ceiling. The first floor primary suite is a private wing and includes separate walk-in dressing rooms and partner bathrooms. A wonderful outdoor salt-water pool shimmers amid pristine stone terraces ideally scaled for coffee, cocktails, dining and large scale entertaining. Separate from the main estate are a two-bedroom guest house, an apple and pear orchard and a raised bed vegetable garden. This is a rare and incredible opportunity to live the dream at your own private oasis just 30 miles from Midtown Manhattan.

20 Meeting House Road, Bedford Corners

$4,700,000

5 Beds ⋅ 7 Baths ⋅ 1016358 MLS

Tucked away at the end of a long private drive and completely hidden from the road, this extraordinary contemporary estate offers one of the most private and captivating settings in Scarsdale. Set on two breathtaking acres bordering Fenway Golf Club, the property is surrounded by mature specimen trees, lush landscaping, a resort-style pool, and a spectacular koi pond home to hundreds of koi, creating a setting that feels worlds away from everyday life. Designed with exceptional craftsmanship and remarkable architectural vision, the residence is defined by soaring ceilings, dramatic walls of glass, abundant natural light, and a seamless connection to the outdoors. A striking copper roof and oversized copper entry door introduce a home that is both architecturally significant and effortlessly livable. The thoughtfully designed floor plan balances grand entertaining with comfortable daily living. A private primary suite serves as a true retreat, complete with dual walk-in closets, a dressing area, and a spa-inspired bath. A separate bedroom wing provides three additional bedrooms and generous accommodations for guests. Formal living and dining rooms frame picturesque views of the pond and grounds through floor-to-ceiling glass, while the expansive eat-in kitchen features custom cabinetry, granite countertops, premium appliances, and a butler’s pantry. At the heart of the home, a spectacular double-height family room invites gathering and relaxation. Vaulted ceilings, tiers of skylights, custom built-ins, walls of glass, and a dramatic stone fireplace create a space that is both impressive in scale and warm in character. The walk-out lower level offers exceptional flexibility, with recreation space, guest accommodations, gym or studio options, abundant storage, and direct access to the outdoors. Outside, the estate unfolds as a private sanctuary. Japanese-inspired gardens, stone terraces, multiple entertaining areas, level lawns, and tranquil water features create an atmosphere rarely found in Westchester. Attached and detached garages provide space for four vehicles, complemented by extensive guest parking and a private driveway that enhances the estate’s exclusivity. Just 32 minutes from Manhattan and located within the highly acclaimed Scarsdale School District, this is a rare opportunity to own one of Scarsdale’s most distinctive residences, an architectural retreat offering exceptional privacy, natural beauty, and a lifestyle unlike any other.

41 Murray Hill Road, Scarsdale

$787,000

3 Beds ⋅ 3 Baths ⋅ 1016600 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bath home, perfectly situated on a quiet, sidewalk-lined street in Yonkers. Offering a wonderful blend of comfort, space, and convenience, this home is ready for its next owner to move right in and enjoy. Inside, you'll find a bright and inviting living area filled with natural light, complemented by hardwood floors throughout. The updated kitchen offers ample cabinet space and room for dining, making it ideal for both everyday living and entertaining. Three generously sized bedrooms and two full and a half baths provide a practical and comfortable layout. Additional features include an indoor garage and a partially finished basement, offering flexible space for a recreation room, home office, gym, storage, or future customization. Step outside to your own private backyard retreat featuring a fully fenced yard, perfect for gatherings, outdoor activities, gardening, or simply relaxing. The private pool and jacuzzi create the perfect setting to enjoy warm summer days and evenings at home. Conveniently located near shopping, dining, parks, schools, and major transportation routes, this well-maintained property offers a fantastic opportunity to enjoy all that Yonkers has to offer.

18 Arden Place, Yonkers

$1,999,000

4 Beds ⋅ 5 Baths ⋅ 1003883 MLS

Welcome to 26 Century Ridge Road, a charming and expansive split-level home with classic Colonial character, ideally situated on a quiet dead-end street in the heart of Purchase, set on approximately one beautifully landscaped acre. Originally built in 1958 and extensively rebuilt in 2001, this special property blends warmth, character, flexibility, and exceptional outdoor living in a setting that is increasingly difficult to find. The home features 4 bedrooms and 4.5 baths thoughtfully arranged across multiple levels, creating a layout that offers both openness and privacy. Two en-suite bedrooms are located one split level from the main, while two more spacious bedrooms and a large bathroom are one level above. At the center of the home are inviting gathering spaces including a welcoming living room with fireplace, formal dining room, and a bright kitchen that opens to the family room and rear deck. One split level down, a substantial home office and additional flexible spaces offer endless possibilities for work, fitness, hobbies, or storage. Another level below, the enormous recreation room, remodeled in 2015, features a second fireplace, summer kitchen, wet bar, and direct access to the rear patio, creating the perfect setting for entertaining, extended guests, or flexible living needs. An inviting breezeway connects the home to the attached garage, providing both convenience and architectural charm while offering seamless access to the home's front and rear outdoor spaces. Outside, the setting is truly exceptional. The 36' x 17' in-ground pool, installed in 2018, is surrounded by elegant stone patios, expansive level lawn areas, and magnificent mature landscaping featuring flowering cherry blossom trees and beautiful specimen plantings that create exceptional privacy and seasonal beauty. Unlike many properties, the grounds offer substantial usable space both in front of and behind the home, creating a true estate-like feel. Multiple outdoor living spaces make the property feel like a private retreat—from the inviting front porch, perfect for morning coffee and peaceful views, to the elevated deck overlooking the pool and manicured grounds, along with the spacious patio below designed for entertaining and summer enjoyment. Additional improvements include three updated condensers installed within recent years, along with abundant storage throughout the home to accommodate a variety of lifestyle needs. Located in one of Purchase's most desirable residential neighborhoods, the property offers an exceptional balance of privacy and convenience. Enjoy proximity to Anderson Hill Road, Purchase Street, area colleges, premier golf courses, country clubs, and parks, while downtown White Plains—with its renowned dining, shopping, entertainment, and Metro-North service—is just minutes away. I-287, the Hutchinson River Parkway, I-684, and Westchester County Airport are all easily accessible. Surrounded by prestigious homes and set on a rare, level acre with outstanding outdoor living, 26 Century Ridge Road presents a unique opportunity to enjoy timeless charm, expansive living space, and a private retreat-like setting in one of Westchester's premier communities.

26 Century Ridge Road, 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.