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

$2,750,000

5 Beds ⋅ 5 Baths ⋅ 1024290 MLS

Set on more than four private acres at the end of a quiet Bedford Hills cul-de-sac, this five-bedroom custom contemporary was reimagined by NYC architect David Howell in collaboration with local architect Robert Robinowitz. Clean lines, custom woodwork, clerestory windows, expansive glass and wide, light-filled hallways define the home, anchored by a dramatic staircase and an open, airy sense of scale. The main level centers on a large Scavolini kitchen and lounge area with a double-sided gas fireplace, along with a spacious living room with double-height ceilings, dining room, powder room and flexible office/playroom. Two additional bedrooms or offices share a full bath. Off the living room, a large deck steps down to a bluestone patio and fire pit, extending the living and entertaining spaces outdoors. Upstairs, the primary suite features radiant-heated floors, a 38-inch gas fireplace, Carrera marble shower, Blu Bathworks fixtures, Duravit tub and sleek custom closets. Two additional bedrooms, connected by a playful peek-a-boo opening, share a beautifully appointed bath with double vanities. A laundry room completes the second floor. The walk-out lower level provides substantial flexible space, a second kitchen and abundant storage. Outside, more than four acres encompass expansive lawns, mature plantings and irrigation, along with a Wagner pool with automatic cover and a generous poolside patio with an aluminum pergola and motorized louvers. A three-car garage with EV charging and a whole house generator complete this modern property. Exceptionally private yet minutes from Bedford Hills, Mt. Kisco, Bedford Village, Metro-North and major highways, this is a distinctive contemporary combining architectural pedigree, a highly livable layout and a glorious large, level backyard.

116 Davids Way, Bedford Hills

$6,995,000

6 Beds ⋅ 8 Baths ⋅ 1045782 MLS

The ultimate legacy estate offering a premiere year-round resort lifestyle. This architecturally significant residence was magnificently expanded and rebuilt in 2009, ensuring every meaningful system and interior design element meets the highest modern standards. Set on 3 spectacular, ultra-private acres, the property features timeless craftsmanship and bespoke finishes, the floor plan flows effortlessly to create exceptional indoor-outdoor entertaining opportunities, and the grand scale of the home is matched only by the magnitude of its amenities. Step inside the striking foyer to discover stunning millwork and moldings, gleaming hardwood floors, and sun-drenched spaces overlooking the sweeping park-like property. The formal living room with wood-burning fireplace and library are dripping with handsome millwork, and the open concept family room with gas fireplace is the perfect place to relax. The spacious eat-in chef’s kitchen boasts highest-end appliances, stunning custom cabinetry, Thassos marble countertops, and connects directly to a fully-appointed wet bar and dining room, ideal for hosting dinner parties. The main level also includes a guest bedroom with ensuite bath and a separate entrance, fully outfitted mudroom, laundry room, and access to the immaculate three-car garage. Ascend to the second level and arrive at the palatial owner’s retreat, including a cozy gas fireplace, 2 custom walk-in closets, spa-like bathroom with dual vanities and separate water closet, and a private stone terrace overlooking the incredible grounds. Also on the second level are 3 additional bedrooms, one with an ensuite bathroom and two sharing a hall bathroom, a modern office with ensuite bathroom which could also serve as a bedroom, and attic storage space. Downstairs, the finished lower level is an ultra-luxury sanctuary unto itself, including a professional-quality gym opening to a saltwater infinity pool, fully-appointed pool cabana, screening room, guest suite, playroom, and an additional office and laundry room. Outside, the lush gardens and grounds include privacy trees and landscaping, multiple patios and terraces, and a brand-new Sport-Tech acrylic tennis court. Ideally located in the prestigious Sterling Ridge section of Harrison, 383 Woodlands is minutes from restaurants, shopping, parkways, private airport, Metro North to Manhattan. Create your own legacy at this remarkable estate. --

383 Woodlands Road, Harrison

$9,950,000

5 Beds ⋅ 6 Baths ⋅ 1033223 MLS

A Contemporary Estate Shaped by Light and Wood on 3.5 Serene Acres An exquisite modern compound designed for expansive living, this residence is distinguished by its rare collection of purpose-built structures and amenities: a custom-designed Japanese tea house, separate party barn, dedicated pottery/art studio, European KLAFS sauna suite, in-ground pool, and serene Zen-inspired grounds — all set across 3.5 private acres. Leading custom team including renowned builder Jim Pousada (Crescent Construction) and architect Justin Minieri the 7,447 sq ft black barn-inspired structure is defined by large industrial Marvin custom windows and a disciplined, modern profile. The architecture is organized around a carefully conceived U-shaped floor plan that embraces a central open-concept living space overlooking a contemplative garden. Soaring double-height ceilings — reaching approximately 20 feet — define the primary living volumes. Rare 20 inch wide-plank oak flooring on main floor, exposed timber beams, and expansive steel-framed glass reflect a quiet wabi-sabi sensibility. The kitchen, appointed with stone countertops and integrated Gaggenau appliances, centers around a generous eat-in island and features custom Leicht cabinetry and display shelving — a true chef’s kitchen. Living and dining areas open to a covered slate terrace complete with infrared heating and wood-burning fireplace. A glass and wood open-riser staircase provides a sculptural connection between levels. The primary suite occupies a private wing with direct garden access, a luxurious light-filled spa bath with freestanding tub, two custom walk-in closets, and a European KLAFS sauna with Moroccan-inspired shower and European IKONNI slat wall accents. On the opposite side, a dedicated pottery and art studio, complete with a glass mechanical garage door and architectural windows, provides creative flexibility. A four-car attached garage, mudroom with custom cabinetry, and spacious laundry with Leicht cabinetry complete the main level. Select high end fixtures include Rocky Mountain hardware, Brizo faucets and accessories, Julien sinks and Toto Neorest toilet. Three additional light-filled bedrooms with walk-in closets are located on the upper level — two en-suite and one with an interconnecting bath adjoining a large play or lounge area overlooking the garden. Anchoring the garden is the tea house, wrapped in Accoya Saguaro wood (delta black color) and crowned by a dramatic IKONNI slat wall ceiling, with custom tatami mat and minimalist detailing that reinterpret traditional Japanese design principles through a modern lens. The separate party barn includes its own kitchen and entertaining space opening to an organic garden. The home is showcased in a major motion feature that is being released in September 2026, reflecting its architectural presence and distinctive design. A true modern compound, 3031 Purchase Street offers estate-scale living within close proximity to Manhattan, premier clubs, Westchester airport including private terminal and top schools offering an opportunity for unrivaled elevated living.

3031 Purchase Street, Purchase

$800,000

4 Beds ⋅ 2 Baths ⋅ 1053621 MLS

LOOKING FOR SPACE? THIS IS NOT YOUR ORDINARY CAPE! Prepare to be wowed when you walk into this home where thoughtful design, incredible space, and an amazing flow come together perfectly for everyday living and large family gatherings. The completely open floor plan flows effortlessly from the raised family room overlooking the spacious dining room and into the fully renovated chef’s kitchen, then continues into the fabulous great room featuring fireplace, a soaring cathedral beamed ceiling. The dream kitchen is truly the heart of the home, complete with **top-of-the-line GE MONARCH appliances, a gas range, lots of upgraded cabinetry, expansive counters, and a large center island perfect for meal prep and entertaining. Beautiful "Augusta" wide-board hardwood floors, a wood-burning stove, and a fireplace add warmth and character to this inviting space. The wonderful flow continues outdoors, where you’ll find three levels of wraparound decking, a hot tub, pool, and a beautiful, tree-shaded backyard, creating an exceptional setting for summer entertaining and relaxing. With four bedrooms, including TWO ON THE MAIN LEVEL, this home offers plenty of flexibility. A main level full bath completes this floor. One of the upstairs bedrooms is currently being used as an office and features a very large walk-in closet. It can easily be converted back to its original spacious bedroom. The lower level adds even more possibilities with two NEWLY RENOVATED fully finished rooms WITH BRAND NEW LVP FLOORING , including one with a SEPARATE ENTRANCE, ideal for a home office where clients can enter directly, a guest space, hobby room, or additional living area. There are also possibilities for an IN LAW SUITE! And the location? Hard to beat! Tucked away on a tree-lined street at the end of a cul-de-sac, yet conveniently close to the Taconic Parkway, Routes 202 and 6, and Lakeland schools.

3494 Overlook Avenue, Yorktown Heights

$680,000

4 Beds ⋅ 2 Baths ⋅ 1054250 MLS

Picture perfect front lawn frames this freshly painted, spacious split level home located in one of Yorktown's most desirable neighborhoods and the perfection continues in the back yard where you will enjoy hours of fun next year in the inground pool....The home has been lovingly maintained by the long time owners for many years and features a 2 year old roof, newer windows in most rooms of the house, fairly new heating system-approx 5 years old and the driveway was recently done and you will appreciate both of the updated baths but the house does need a bit of cosmetic updating! With a bedroom on the first level along with a full bath it might be perfect for your Mom or Dad so they can live with the family yet have their own space....And wait until you see the spacious kitchen with a great dining area overlooking the patio and pool area and there's even a cute deck off the kitchen where you can enjoy your morning coffee...This home offers so much- town water and sewer, gas heat/ gas cooking, fabulous level property and convenience to all- Taconic Pkwy, shopping, schools, restaurants in a quiet neighborhood location....Make your plans now to see this place and make it your own!! Get in by Thanksgiving and host in your own dining room then relax by the fireplace in the family room- this house has everything you have been looking for!!

280 Somerston Road, Yorktown Heights

$455,000

2 Beds ⋅ 2 Baths ⋅ 1053845 MLS

Tucked away above the Hudson River in the private Liberty Knoll community, this two bedroom renovated end-unit townhouse offers approximately 1,452 square feet across three levels. Dual exposures bring abundant natural light throughout, while the main level features a renovated kitchen, bright living and dining areas, a powder room and a rear deck. Upstairs, a spacious primary bedroom is joined by a renovated full bathroom and an additional bedroom offering flexible living space. An attached one-car garage opens directly into the finished basement, adding everyday convenience and additional space for a rec room or office. Liberty Knoll residents enjoy a community pool and clubhouse, plus a weekday reimbursement program for transportation to the nearby Scarborough Metro-North station. Close to shopping, the Hudson River and the Rivertowns, 13 Knoll View offers the ease of townhouse living with the space, flexibility and updates that make it an exceptional find.

13 Knoll View, Ossining

$1,495,000

5 Beds ⋅ 5 Baths ⋅ 1041208 MLS

Set high on 2.94 landscaped acres in South Salem, This home is a distinctive Yates Colonial that feels equally suited to everyday life as it does to a weekend country getaway. Freshly painted inside and out, the home retains the unique architectural character that makes it memorable. A cedar shingle multidimensional roofline, custom copper-topped turret, shaker shingle siding and a welcoming covered front porch. The dramatic two-story foyer sets the tone with a guest closet & half bath. A graceful staircase with newly installed runner & landing carpeting ascends within the turret with large windows leading to a large open second-floor landing overlooking the entry. This space creates a quiet sitting area, reading nook or game table spot. From the foyer the home flows naturally into the formal living room and dining room, connected by a double-sided wood burning fireplace and framed by large windows and french door with side glass panels that open to a balcony. The spacious chef’s kitchen looks out toward the pool and landscaped grounds. With an abundance of cabinetry, a large center island and a generous eat-in area that leads to the patio & pool, this kitchen can easily accommodate a large gathering. Directly off the kitchen is the cozy family room featuring custom built-ins, high ceilings, large windows overlooking the front grounds and the third wood burning fireplace. A first-floor bedroom ensuite with its own entrance from the pool area offers flexibility for guests, or a private office, while the adjoining full bath and first-floor laundry add everyday convenience. Upstairs the primary bedroom ensuite is privately positioned, with vaulted beamed ceiling, walk in closet, separate shower & soaking tub, double vanities. Three additional bedrooms are naturally separated and share a renovated hall bath. The home continues downstairs with approximately 1,425 square feet of space, multiple large walk-in closets, a half bath, full walkout access to the property, offering additional room to work, play or simply spread out. Outside is where your next summer experience begins. A freeform Gunite pool and stone patio create a private setting for swimming, dining and lingering into the evening, surrounded by mature landscaping and the natural beauty of the property. The pond that is on the property had been part of the owner’s lifestyle with everyone enjoying time out on the water. It has not been used lately and the stone path can easily be cleared back again. The attached two-car garage and thoughtfully placed storage throughout the home add to its practicality. The setting provides a true Northern Westchester country experience without giving up convenience. Close to restaurants, shops and daily amenities, with easy access to Ridgefield and Katonah. Leon Levy Preserve and Onatru farm park are both conveniently less than 2 miles away. A true move-in ready home.

195 Kitchawan Road, South Salem

$2,950,000

5 Beds ⋅ 5 Baths ⋅ 1015705 MLS

Exceptional Georgian Colonial elegance meets private resort living on 3.18 beautifully landscaped acres in exclusive Rock Rim Ponds. Behind a gated entry, this remarkable Pound Ridge estate offers timeless architecture, refined craftsmanship and exceptional privacy, yet is minutes from Bedford Village, Stamford, the Merritt Parkway and I-684. A dramatic double-height foyer introduces elegant interiors with cherry hardwood floors, custom millwork and cabinetry, three masonry fireplaces and gracious spaces for both formal and casual entertaining. The professionally equipped chef’s kitchen features a well-appointed butler’s pantry with sink, refrigerator, wine cooler and dishwasher. Five bedrooms include a vaulted primary suite with luxurious bath and a private first-floor guest wing. A bonus room above the three-car heated garage adds flexibility. Outside, rolling lawns, mature specimen trees and lush plantings create a serene backdrop for expansive terraces and a multilevel Brazilian Ironwood deck. The Gunite pool, spa and waterfall, covered patio and charming gazebo offer an extraordinary setting for entertaining or relaxing. Beautiful walls, walkways and steps complete this private oasis—a sophisticated Pound Ridge retreat designed for exceptional living.

11 S Eastern Farm Road, Pound Ridge

$1,175,000

3 Beds ⋅ 2 Baths ⋅ 1054284 MLS

Tucked away on two private acres, this distinctive mid-century modern chalet feels like a world of its own. Set well back from the road and enveloped by mature trees, the home has the rare feeling of a true retreat—peaceful, private and deeply connected to its natural surroundings—yet is remarkably convenient to town, trains and commuting routes. Inside, soaring 18-foot ceilings and dramatic walls of glass fill the living spaces with natural light and frame the wooded landscape beyond. Warm wood tones, clean architectural lines and custom doors add character throughout, while expansive wraparound decks extend the living space into the treetops, creating an effortless indoor-outdoor flow. The private setting continues outdoors with a pool, traditional wood-fired sauna and landscape lighting, making the property equally suited to quiet mornings, summer afternoons and evenings under the stars. Thoughtful investments and updates, a first floor primary and whole house generator. With easy access to the Merritt Parkway and I-684, as well as nearby train stations in Stamford, Mount Kisco and Bedford Hills, this hidden sanctuary offers the best of both worlds: the feeling of getting away from it all, without actually being far away.

380 Long Ridge Road, Pound Ridge

$2,495,000

6 Beds ⋅ 7 Baths ⋅ 1053438 MLS

DISTINGUISHED 1940’S ESTATE. First time listed in decades! One of the original area estate properties. Circular drive to 3.6 manicured acres with remarkable age-old trees, verdant lawns and flowering shrubs. Impressive Stone and Shingle Country House dating to the 1940’s with many original details perfectly preserved. Stunning formal Entrance Hall with sweeping staircase. Powder Room with original art-deco fixtures. Beautifully proportioned Living Room with high ceiling, curved window wall and fireplace. Wood-paneled Library with fireplace, wet bar and door to slate-floored Sunroom. Formal Dining Room with dramatic recessed ceiling, soffit lighting and wood parquet floor. Kitchen with Breakfast Area. First floor Primary Suite with two Baths. Three additional spacious Bedrooms plus Two additional smaller Bedrooms. Lower Level Recreation Room with fireplace. Fabulous awning-covered Terrace for outdoor entertaining. Swimming Pool with Cabana next to the tennis court. Conveniently located with easy access to the Hutchinson River Parkway, I-287, I-684, I-95 and the Westchester County Airport. A truly rare offering!

51 Kenilworth Road, Rye

$899,000

3 Beds ⋅ 2 Baths ⋅ 1053601 MLS

Welcome to this truly special Mount Kisco property, featuring a charming 3-bedroom main home and a 1-bedroom stone cottage. Set on over 1.5 acres, this one-story ranch and charming guest cottage are complemented by a spring-fed pond and a 20x40 cement pool with a large patio. The cottage features its own independent driveway and utilities, which was successfully rented through June. Filled with natural light, the main home features hardwood floors throughout, has generously sized bedrooms with closets galore and even has laundry located on the main floor. The kitchen boasts solid wood cabinets and a perfect sitting area with vaulted ceilings and skylights behind exposed wood beams, while the serene slate-floor sunroom invites you to relax and admire the picturesque views. Overlooking the tranquil pond - alive with painted turtles and local wildlife - the property feels like your own private sanctuary right from the living room. Even the expansive, flat backyard offers endless potential for a grand vegetable garden, lively outdoor entertaining, or a dreamy play space accompanied by a spacious ride-in barn that's equipped with electricity and a second-story storage loft. Downstairs, the basement presents a fantastic footprint for expansion, complete with convenient walk-out sliding glass doors and easy plumbing access. There are two convenient garage bays that offer dedicated storage space on the right alongside a remote-opening door on the left for easy pull-in access. Take a left out of the driveway and in about two miles you'll find yourself at the train station, restaurants, shopping centers, and everything you could possibly need! Schedule a private tour today and experience this property for yourself.

109 Pines Bridge Road, Bedford Corners

$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

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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.