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

$875,000

3 Beds ⋅ 3 Baths ⋅ 990992 MLS

Welcome to your own private retreat! Nestled on 0.66 lushly landscaped acres, this stunning contemporary home offers sophisticated design, modern comfort, and a spectacular in-ground pool. Inside, vaulted ceilings and custom windows flood the home with natural light, creating bright, sun-filled spaces. At the heart of the home, the custom kitchen features soapstone countertops, custom cabinetry, premium stainless steel appliances, a farmhouse sink, and island seating, flowing effortlessly into the dining area and dramatic living room anchored by a striking brick fireplace. The main level includes a serene primary suite with an en-suite bath, two additional bedrooms, and a skylit hall bath. The finished lower level offers exceptional flexibility with polished concrete floors, a spacious recreation room, large home office, full bath, mudroom with laundry, abundant storage, and direct access to the attached two-car garage. Outside, the property truly shines. Recent improvements—including a new pool liner, custom stonework, and an expanded patio—have transformed the backyard into the perfect setting for relaxing and entertaining. Enjoy summer days by the pool, gather with friends on the patio, or unwind on the screened porch overlooking the private backyard. Additional updates include a new roof (2023), screened porch improvements, a garden path, a mounted fire guard, and more. Optional membership in the Lakeview Homeowners Association offers access to a private lake, beach, tennis courts, playground, and picnic area. Conveniently located near Metro-North, major highways, Charles Cook Pool, shopping, and dining, this exceptional home offers the perfect balance of privacy and convenience—all less than an hour from New York City.

27 Lakeview Avenue W, Cortlandt Manor

$2,490,000

5 Beds ⋅ 5 Baths ⋅ 1014768 MLS

Welcome to this extraordinary Tudor masterpiece in the heart of the coveted Cotswolds neighborhood of the award-winning Edgemont School District, just a short walk to schools, downtown Scarsdale shops and the Metro North train for a 32 minute commute to Grand Central. Thoughtfully renovated from top to bottom, this exceptional home seamlessly blends timeless architectural character with sophisticated modern living. The stunning chef's kitchen is the centerpiece of the home, featuring premium appliances including a Wolf six-burner range with griddle and double ovens, Sub-Zero refrigerator/freezer, Wolf microwave, KitchenAid dishwasher, wine refrigerator, and striking quartz countertops with a waterfall breakfast bar. The kitchen flows effortlessly into the family room, where French doors open to a patio overlooking the spectacular saltwater pool, lush level backyard, and beautifully curated specimen trees and plantings. A spacious roof deck above the garage provides an additional outdoor retreat for dining, entertaining, or simply relaxing. The first level also includes a beautifully renovated powder room, large coat closet, butler's pantry, formal dining room, and an impressive living room with soaring cathedral ceilings, original exposed beams, and a dramatic wood-burning fireplace with stone surround. The open-concept layout offers the perfect balance of elegant entertaining spaces and comfortable everyday living. The second level features a luxurious primary suite with a renovated marble bath, large walk-in closet, and two additional closets. Two additional spacious bedrooms and a beautifully updated hall bath with marble finishes complete this floor. The third level offers two more bedrooms with oversized walk-in closets and a renovated hall bath, providing exceptional flexibility for guests or as a home office. The walk-out lower level is equally impressive, anchored by a gorgeous recreation room with luxury vinyl flooring, built-in kitchenette with beverage refrigerator and bar sink, and large sliding glass doors that create a seamless connection to the pool and backyard. Original stone walls add warmth and character, while a hidden subterranean wine cellar tucked inside a large walk-in closet offers a unique and memorable feature. An additional playroom, full bath, and laundry room complete this bright and inviting level. Recent improvements include conversion from oil to gas heat, refinished hardwood floors, interior painting throughout, extensive pool upgrades, new open kitchen/family room, all new baths and numerous additional enhancements. A two-car attached garage, heated driveway, front walkway, and stairway ensure year-round convenience and ease. Set on a beautifully landscaped property with a magnificent slate roof, expansive level play space, and an A+ location in one of Edgemont's most desirable neighborhoods, this turnkey home offers the rare combination of architectural beauty, modern luxury, and exceptional outdoor living. A truly special Edgemont offering.

14 Withington Road, Scarsdale

$799,999

5 Beds ⋅ 3 Baths ⋅ 1014347 MLS

Spacious colonial-style single-family home located in the desirable Bryn Mawr section of Yonkers, sitting on a 50 x 100 lot offering ample space both inside and out. The main level features a foyer, living room, dining area, kitchen, half bathroom, and a family room perfect for everyday living and entertaining. The second level offers an extremely large primary bedroom created by combining two rooms, along with three additional bedrooms and a full bathroom. The third level features a walk-up attic with a large open space, ideal for extending living space or creating a home office, gym, or additional bedrooms. The finished walkout basement offers even more flexibility with an open layout, kitchenette, and full bathroom, ideal for extended living or recreation. Additional highlights include solar panels, a two-car garage, driveway parking, and a private fenced backyard perfect for BBQs and entertaining, including a deck with an above-ground pool. Conveniently located near Tuckahoe Road with access to local shops, eateries, and public transit. Close to major roadways including the Bronx River Parkway, Saw Mill River Parkway, and I-87 (Major Deegan Expressway), providing easy access to New York City and surrounding areas. Nearby Ridge Hill Mall featuring retail stores, dining, and everything needed for everyday convenience.

26 Normandy Road, Yonkers

$7,495,000

6 Beds ⋅ 8 Baths ⋅ 878004 MLS

Hamptons lifestyle meets Westchester location! Introducing Four Winds, a spectacular private estate offering the scale, beauty, privacy and resort experience of the Hamptons, right here in Westchester. Truly one of a kind, the residence is set on 3 magnificent acres in Harrison’s prestigious Sterling Ridge. Extensively expanded and comprehensively renovated in 2009, it presents a rare combination of architectural distinction, sophisticated modern design, remarkable privacy and resort-style amenities seldom found in the area. From the moment you arrive, the property is breathtaking. Sweeping park-like lawns frame a saltwater infinity pool, expansive terraces, multiple patios and a new environmentally friendly Sport-Tech acrylic tennis court. Every element has been designed for recreation, relaxation and entertaining—all just minutes from Manhattan. Inside, walls of glass fill the home with natural light and create an effortless connection to the magnificent grounds. A bright, beautifully detailed foyer with seamlessly integrated hidden doors leads to an inviting library and an impressive living room with a striking architectural ceiling. The showstopping chef’s kitchen features Thassos marble countertops, a sunlit breakfast area and sleek center island, flowing effortlessly into an onyx-clad wet bar and super-chic dining room. A fabulous family room, private-entry au pair suite, full bath, outfitted mudroom, laundry room and direct access to the three-car garage complete this level. Upstairs, a luxurious lounge anchors three beautifully appointed bedrooms, including two ensuite. Privately positioned at one end of the floor, the serene primary suite offers a private terrace, two walk-in closets and a spa-like bath. At the opposite end, closer to the additional bedrooms, a sunny modernist office may also serve as an additional bedroom and features an ensuite full bath. Attic storage completes this level. The lower level rivals a private club, featuring a luxe home theater, sprawling gym opening directly to the pool, stylish cabana, guest suite, second office, playroom and an additional laundry room. Featured as the setting for two hit television series, Four Winds is a truly singular offering—an incomparable setting for extraordinary living, entertaining and making memories for generations to come.

383 Woodlands Road, Harrison

$1,895,000

5 Beds ⋅ 4 Baths ⋅ 1012163 MLS

STUNNING RENOVATION. Crisp clean lines and sun-filled spaces. Creative re-imagination of a traditional ranch. Bleached oak floors with a matte finish, clean white walls create a fresh living space. Light and airy spaces with walls of windows showcasing property views. Warm and inviting Living Room with fireplace. Formal Dining Room with picture window overlooking the grounds. Absolutely stunning Kitchen with custom cabinetry with mitered Quartz counters, high-end appliances, a center island and doors open to a stone porch for easy indoor-outdoor entertaining. Spacious Family Room with stone fireplace and wet bar. Five Bedrooms include Primary Suite with luxurious Bath. Gym/Yoga Room, Home Office. Two Laundry rooms, one on each level. Oversized 3 car garage with 12 ft Ceilings. Large flagstone terrace with covered dining/seating area. Over two finely landscaped acres with incredible stonework, rolling lawns and flowering perennials. Incredible free-form swimming pool with spa awaiting restoration. Located in the heart of Bedford Corners, just moments from the shops of Bedford Hills, Mount Kisco and Katonah. Easy access to the Sawmill Parkway and the Metro North train.

736 Croton Lake Road, Bedford Corners

$5,150,000

6 Beds ⋅ 8 Baths ⋅ 1004715 MLS

Completely rebuilt and exquisitely expanded, this exceptional new construction Colonial seamlessly blends timeless architecture with sophisticated modern living on a beautiful level property featuring a sparkling pool. Ideally situated in the heart of coveted Fox Meadow, this remarkable residence is just moments from top-rated schools, parks, shops, restaurants, the library, and Metro-North. Designed for today's lifestyle, the home showcases soaring ceilings, abundant natural light, and beautifully curated finishes throughout. At the heart of the home is a spectacular custom chef's kitchen with state-of-the-art appliances, an oversized center island, and sleek designer details. The kitchen flows effortlessly into a dramatic family room with cathedral ceilings and walls of glass overlooking the patio and pool, creating the ultimate setting for seamless indoor-outdoor living and entertaining. The thoughtfully designed first floor also features an elegant dining room with butler's pantry, a gracious living room with fireplace, a private office with cathedral ceilings and access to a covered porch, a first-floor en-suite guest bedroom, and a custom mudroom with built-in cubbies leading to the attached two-car garage. Upstairs, the luxurious primary suite is a true retreat, highlighted by vaulted ceilings, two walk-in closets, and a spa-inspired bath. Four additional en-suite bedrooms and a conveniently located laundry room complete the second level. The expansive walkout lower level offers exceptional flexibility with a large recreation area ideal for a gym, media room, playroom, or all three, along with direct access to a full bath for pool guests. An additional en-suite bedroom provides the perfect space for guests, an au pair, or extended family. A rare opportunity to own luxury new construction in one of Scarsdale's most prestigious neighborhoods, just minutes from the village, train, shopping, and Scarsdale High School. This extraordinary home offers the perfect combination of elegance, comfort, and convenience.

65 Fox Meadow Road, Scarsdale

$759,000

3 Beds ⋅ 3 Baths ⋅ 1012840 MLS

Beautiful 3-bedroom, 1-family home in a prime Yorktown Heights location! Features 1 full bath and 2 half baths, including a private half bath in the primary bedroom, hardwood floors, an eat-in kitchen with stainless steel appliances, and updated bathrooms throughout. The finished walk-out basement offers a cozy fireplace and bonus room, perfect for additional living space, a home office, or recreation area. Enjoy outdoor living with a fenced-in above-ground pool and deck, plus a spacious 2-car garage. Conveniently located near the Taconic State Parkway, Franklin D. Roosevelt State Park, shopping, hiking trails, major highways, and excellent schools. Move-in ready and close to everything!

1019 Fox Meadow Road, Yorktown Heights

$3,995,000

7 Beds ⋅ 6 Baths ⋅ 1012192 MLS

Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular 7-bedroom main residence, where grand, light-filled rooms showcase timeless craftsmanship and sweeping vistas from nearly every window. Multiple primary suites and en suite bedrooms provide exceptional comfort and flexibility for hosting overnight guests. The property also features a 5-bedroom, 2 bath, caretaker’s home and a historic carriage house with a 5-car garage, horse stalls, a chicken house, and a sheep house—ideal for equestrian pursuits, hobby farming, or simply enjoying the pastoral lifestyle. Whether you envision a private compound, event venue, or generational retreat, this setting offers endless possibilities. With its rich heritage, refined elegance, and serene privacy, Old Dam Farm is more than a property—it’s a place to create memories that will last a lifetime.

433 Arcady Road, Ossining

$2,650,000

5 Beds ⋅ 6 Baths ⋅ 1001204 MLS

Fabulous Country Retreat. Absolute serenity! Long drive through scenic woodlands to peaceful privacy. Fabulous high site with glorious sunset views. Beautifully landscaped grounds with an array of fine and flowering plantings, fenced for deer. Free-form Swimming Pool with spa and two waterfalls. Perfectly positioned Tennis Court. Architect-designed Country House with contemporary and traditional elements. Stunning interior spaces with beautifully scaled rooms, vaulted ceilings and walls of windows. Exceptional craftsmanship with substantial millwork, wide board oak floors and high-end finishes. Nearly 5700 square feet of finely appointed living space. Fabulous open floorplan with impressive main rooms for entertaining. Chef’s Kitchen with center island, custom cabinetry, marble counters and high-end appliances. Five Bedrooms include a spectacular Primary Suite with Dressing Room, Office, Gym and Two Baths. Lower level Recreation Room. The ultimate estate for the most discerning buyer.

17 Eastwoods Road, Pound Ridge

$3,500,000

10 Beds ⋅ 6 Baths ⋅ 999615 MLS

Hidden behind a storybook cobblestone drive and set across 45 breathtaking acres in the heart of the Hudson Valley, this extraordinary 1932 Tudor estate is the kind of property that rarely comes to market - a true legacy compound offering cinematic beauty, complete privacy, and effortless access to Manhattan. For the city buyer dreaming of a refined countryside escape without sacrificing sophistication or convenience, this is the ultimate retreat. From the moment you arrive, the estate feels transported from another era. A winding cobblestone driveway crafted from salvaged historic Bronx street stones loops through rolling lawns, curated gardens, and towering trees before revealing the magnificent manor overlooking its own private 3-acre pond. The original boathouse sits at the water’s edge, while a heated pool, tennis court, Japanese garden, orchard, vegetable and berry gardens, greenhouse, and heated pottery studio create a lifestyle reminiscent of a private European country estate. The nearly 9,000-square-foot residence is rich with warmth, grandeur, and unforgettable architectural detail. The awe-inspiring Great Room is nothing short of spectacular, anchored by a massive stone fireplace, soaring 40-foot oak-beamed ceilings, and dramatic walls of glass opening to sweeping pond views. Every room tells a story, from the stately oak-paneled library and elegant entertaining spaces to intimate sitting rooms, hidden carved staircases, and beautifully preserved plaster walls that showcase the home’s old-world craftsmanship. Designed for luxurious multi-generational living and grand entertaining alike, the estate features 10 bedrooms spread across thoughtfully designed wings, including guest accommodations and private caretaker quarters. The newly renovated primary suite rivals a five-star hotel, complete with its own fireplace, lounge/office with kitchenette, spa-like bath, dressing room, and tranquil views over the grounds. Nearly every fireplace throughout the home is operational, bringing warmth and romance to every season. Three separate tax lots, including an additional lot near the guest house, add a level of rarity and long-term value seldom found in estates of this caliber. Modern upgrades quietly support the property’s timeless elegance, including heated garages, multiple propane generators, upgraded well systems, mixed central air, and extensive utility and storage spaces. Private, historic, and impossibly romantic, this is more than a home. It is a destination, a lifestyle, and a once-in-a-generation opportunity to own one of the Hudson Valley’s most magical estates, all within easy reach of New York City.

335 Croton Dam Road, Ossining

$12,995,000

5 Beds ⋅ 7 Baths ⋅ 1008597 MLS

Red Horse Farm. An unparalleled opportunity to acquire 102 private acres in the heart of North Salem Equestrian Country. The approach is nothing short of captivating - with a winding driveway enveloped by lush greenery, rolling fields, classic stone walls, 360 degree panoramic views, and a sense of profound peacefulness. The spectacular 9,500 sq ft main residence exudes understated luxury - at its finest. Walls of French doors throughout the home blur the line between exquisite interior spaces and outdoor beauty. Upon entry, you are graced by an elegant, airy foyer with soaring ceilings, a stunning mahogany staircase, and striking molding and paneling throughout. The sensibility is one of old world charm & extraordinary quality, with a modern understanding of living and incredible room scale. The main floor includes a light filled living room with fireplace, formal dining room, a cozy paneled library with fireplace, family room with fireplace, butler’s pantry, wet bar, and a state-of-the-art chef’s kitchen with two inch thick marble countertops, viking appliances, and custom fixtures and cabinetry. French doors lead from the kitchen to a large screened-in porch with a massive stone fireplace, all positioned to survey the breathtaking views beyond while overlooking the enormous 30’ x 65’ Gunite pool & spa, with expansive terrace and entertaining area. Also on the main floor, there are two powder rooms, a light-filled mud room/ potting room with side entrance, wide back staircase, access to the three car garage and a well-designed laundry room. Located in its own wing on the main level through a private entry hall, the marvelous first floor primary bedroom suite offers a true refuge with outstanding his and hers bathrooms and closets, as well as french doors to a private seating area. Upstairs, there are two en-suite guest bedrooms, as well as two family bedrooms with a sitting area and full bath. There is also expansive attic space, additional storage rooms, and a lower level basement with 12 ft ceilings for endless possibilities of additional expansion. This remarkable property has served as a thriving alpaca farm for the past decade, with several Equestrian structures and possibilities still in place. Presently, there is a King Construction built 14 stall main barn with two wash stalls, two powder rooms, an office, a tack room, multiple outdoor shedrow barns, 17 grass turnout paddocks, a 180’ x 72’ Indoor Arena, a 135’ x 300’ site for an outdoor arena, two 1 bedroom, 1 bath grooms’ apartments, a commercial size 6 bay storage garage, plus a 3 bedroom, 2.5 bath Caretaker's residence. The property has coveted direct North Salem Bridle Trails access, abuts Olympic caliber stables and significant estates on all sides, and is located 1.7 miles from Old Salem Farm and within close proximity to other top area horse shows. Minutes to highways and the train, one hour from NYC. A rare and unreplicable offering.

364 Hardscrabble Road, North Salem

$1,150,000

4 Beds ⋅ 3 Baths ⋅ 1008352 MLS

Arriving at the end of the cul-de-sac and the wonder begins. Circular drive leads you to an elegant covered front entrance way. The grand hall greets you and the decision which way to go is intriguing. The enormous great room is quintessentially great! Soaring ceilings, fantastic bar, and enough room for a party of 60. The massive fireplace gives a warm, cozy atmosphere to compliment the expansive space. Wandering through the home is mesmerizing, be it the cozy office, family room or timeless eat in kitchen. All the bedrooms have whimsical nooks and crannies to explore. The lower level is ready for your ideas to create even more living space. The heated, free form pool with spa, feels like a vacation resort. All this set on a shy two-acre property with the ultimate in privacy yet convenient to town and NYC by either car or train.

2341 Blue Spruce Drive, Yorktown Heights

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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.