Homes for Sale with a Pool in Westchester, NY

Welcome to 24 Trails End, an unparalleled private resort estate redefining luxury living on over 9 pristine, park-like acres. This majestic brick Colonial, quietly positioned at the end of a prestigious cul-de-sac, overlooks a scenic, spring-fed pond. Inside, classic architectural sophistication meets modern design, highlighted by a soaring double-height great room, dual home offices, and a rich mahogany billiard room with a wet bar and fireplace. The heart of the home is an expansive chef's kitchen, with an oversized marble island, and a sunny breakfast area. The lower level is an extraordinary recreation destination, boasting a 2600 sqft indoor sports court lined for basketball and pickleball, alongside a full home gym. Step outside to your private backyard paradise with an inviting heated Gunite pool, integrated spa, and a pool house/cabana surrounded by sprawling bluestone terraces and meandering walking trails. Two firepits located around the property and a serene pond with an island, an additional firepit and two docks for unmotorized boat usage complete this spectacular picture. An ultra-private lifestyle compound in the award winning Chappaqua schools, just under an hour from Manhattan.

24 Trails End, Chappaqua

$1,199,999

3 Beds ⋅ 2 Baths ⋅ 1045466 MLS

Experience the elegance of this exquisite ranch-style residence situated in the heart of Valhalla, boasting nearly 3,000 square feet of meticulously updated living space. The home is adorned with gleaming hardwood floors throughout, creating an ambiance of warmth and sophistication. The main level offers effortless living with three generously proportioned bedrooms, including a serene primary suite, a laundry area, and a second full bathroom. The beautifully updated eat-in kitchen features stainless steel appliances and provides an inviting space for culinary pursuits. The formal dining room and an inviting sitting area also enhance the perfect setting for refined entertaining. The expansive lower level adds over 1,000 square feet of versatile space, ideal for family gatherings, a home theater, or a private retreat. Step outside to your private sanctuary featuring a fully fenced, in-ground pool accented by elegant stonework, complemented by a dedicated patio area perfect for outdoor dining and barbecues. The immaculately landscaped lawn, situated on just under one acre, enhances the home's enchanting curb appeal. Additional amenities include a spacious two-car attached garage and an elongated driveway, offering ample parking. This exceptional residence seamlessly combines luxurious comfort with timeless style in a coveted Valhalla location.

72 Eastview Drive, Valhalla

$379,999

2 Beds ⋅ 2 Baths ⋅ 1050130 MLS

Welcome to 3 Waterview Estate in Peekskill! This fully renovated, move-in-ready condo offers a bright and modern interior with updates throughout. The brand-new kitchen features white shaker cabinetry, quartz countertops, subway tile backsplash, stainless steel appliances and modern black fixtures. The spacious living area offers new flooring, fresh paint, updated lighting and sliding glass doors leading to a private outdoor patio. Both bathrooms have been beautifully updated with contemporary finishes, and the unit also features in-unit laundry, generously sized bedrooms and excellent closet space, including a walk-in closet. Waterview Estates offers community amenities including an outdoor pool and tennis courts, all while being conveniently located near shopping, dining, transportation and major commuter routes. Nothing to do but move in and enjoy!

3 Waterview Estate

$575,000

1 Beds ⋅ 2 Baths ⋅ 1049345 MLS

Welcome to The Brooke Club, an established residential community offering a wonderful combination of comfort, amenities, and convenience. Beautifully upgraded and thoughtfully maintained, this attached single-family home offers a flexible and distinctive floor plan complemented by a substantial list of meaningful improvements. On the main level, at the heart of the home, is a renovated chef's kitchen featuring quartz countertops, updated flooring, and a suite of Bosch appliances. Separate living and dining areas provide wonderful spaces for everyday living and entertaining as well as a fireplace. There is also a renovated full bathroom, separate laundry closet, pantry and direct access to the attached garage. The 2nd level offers an impressive primary suite providing a private retreat, complete with a beautifully renovated full bathroom and custom cedar-lined walk-in closet. The dramatic lofted mezzanine is multi-functional with cathedral ceilings adding architectural interest and valuable living space, plus a bonus room which can easily serve as a second bedroom. The home lives comfortably like a 2-bedroom, with excellent flexibility for guests, a home office or den. The private rear patio provides an inviting extension of the living space for outdoor dining, entertaining, or simply relaxing with park-like views and breathtaking seasonal sunsets. An attached garage plus 2 in driveway, offer the convenience of 3-car parking. Numerous upgrades and improvements have created a truly turn-key home designed to be enjoyed today and grown into for the long term, allowing its next owner to move in with confidence and make it their own for years to come. Residents of The Brooke Club enjoy updated community amenities, including an indoor pool complex and fitness center. Conveniently positioned near major parkway access and Metro-North, this location provides easy connections throughout Westchester, to New York City, and points north and south.

5-03 Brooke Club Drive, Ossining

$5,150,000

6 Beds ⋅ 8 Baths ⋅ 1049142 MLS

READY TO MOVE IN!! 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

$5,795,000

5 Beds ⋅ 7 Baths ⋅ 1033235 MLS

Where timeless architecture meets resort-style living. Set within Scarsdale’s coveted Murray Hill Estate Section, this distinguished Georgian Colonial offers a rare combination of scale, privacy, craftsmanship, and refined luxury. Encompassing 1.41 acres at the highest elevation in Scarsdale, this gated legacy property is an exceptional private sanctuary, thoughtfully designed for both gracious living and effortless entertaining. From the moment of arrival, the home’s commanding street presence and enduring architectural character is evident. Grand proportions, high ceilings, oversized windows, rich hardwood floors (exposed and under carpet), elegant Greek dentil moldings, and stone fireplaces create a sense of permanence and sophistication throughout. At the heart of the residence is a remarkable St. Charles kitchen, appointed with custom hand-carved cherry wood cabinetry, granite countertops, and a distinctive stone fireside lounge—an inviting setting for intimate gatherings or memorable entertaining. Enjoy a seamless transition between indoor and outdoor living with a 2500 square foot flagstone courtyard, offering an exceptional setting for al fresco dining, entertaining, and effortless indoor-outdoor flow. The home’s extraordinary amenities rival those of a private resort. A heated indoor gunite diving pool anchors the wellness and recreation wing, complemented by a jacuzzi, dedicated spa room, sauna, and steam shower. The finished lower level offers additional living and entertaining space, a fireplace, exterior access, and additional plumbing lines, providing exceptional flexibility for future customization. With five bedrooms, seven full bathrooms, and two office/flex spaces, the residence offers an abundance of space for family, guests, work, and relaxation. Two generously sized attics provide substantial storage and additional possibilities. Outside, the expansive level grounds offer an extraordinary canvas for creating a true private resort. There is ample room to add an outdoor pool, tennis or basketball court, putting green, or other recreational amenities, while the estate’s elevated setting provides an exceptional sense of privacy and serenity. The property is equally impressive from a utility and infrastructure perspective, featuring a four-car garage, motor court accommodating up to 15 cars, Generac 80kW whole-house generator, five-zone HVAC, central vacuum, automated front gate, whole-house water purification, integrated sound system, home security, and extensive video surveillance system. This is more than a residence—it is a lifestyle. A rare opportunity to experience private, resort-inspired living in one of Scarsdale’s most prestigious estate enclaves, while remaining conveniently close to Scarsdale Village, top-rated schools, major highways, and transportation. Manhattan is less than an hour away by car, with Metro-North providing 30-minute access to Grand Central Terminal. A truly exceptional Scarsdale estate where timeless elegance, sophisticated amenities, and extraordinary privacy converge.

109 Mamaroneck Road, Scarsdale

$2,250,000

4 Beds ⋅ 4 Baths ⋅ 1048139 MLS

OVER 14 PEACEFUL ACRES. Located off a quiet country lane, the perfect private refuge. Exquisite setting with level lawns, Ornamental Grasses and remarkable plantings. Incredible Weeping Cherry, Cut-leaf Maple, Dogwoods, Mountain Laurel, Lilac and Andromeda. Heated, gunite Swimming Pool surrounded by colorful perennials. Classic Country Colonial with warm and inviting living space. Beautifully scaled Living Room with fireplace. Library with extensive built-ins – the perfect spot for reading or working remotely. Comfortable Great Room with fireplace and wet bar. Skylit Sunroom, with window seat, brick floor and doors to the deck for easy indoor-outdoor entertaining. Well-designed Kitchen with center island, pantry and breakfast area. Spacious Primary Suite with fireplace and Bath. Guest Suite with Bedroom and Bath. Two additional Bedrooms. Multi-purpose Bonus Room with rear staircase. Garages for four cars. Convenient location moments to Scotts Corners, the town park, local schools and the library. Easy drive to New Canaan, Stamford and Bedford Village as well as I-684, the Merritt Parkway and Metro North trains. First time listed in over 40 years!

29 Bender Way, Pound Ridge

$3,295,000

9 Beds ⋅ 5 Baths ⋅ 1047567 MLS

Gracing an impressive 4.28 acres overlooking the Hudson River, this exceptional nine-bedroom Tarrytown estate offers a rare combination of historic character, resort-style living, modern sophistication, and timeless elegance. Built in 1929 and affectionately known as Whitehall, the residence has been meticulously updated and maintained, preserving its architectural integrity while embracing the comforts, style, and expectations of today’s most discerning buyer. Spectacular water views span the entire home, providing an extraordinary backdrop for Hudson River sunsets. Distinctive gates mark the entrance to a private approach through beautifully landscaped grounds designed for a resort-caliber lifestyle, featuring a private pool and hot tub, expansive terraces, an impressive pool house with full kitchen, recreation room, steam and outdoor showers, private tennis court, tranquil pond, mature gardens, and winding stone paths. Inside the 8,329-square-foot haven, stained glass, arched openings, sweeping verandas, striking wood paneling, stately fireplaces, wrought-iron details, hidden doors, and other distinctive architectural elements preserve the home’s heritage, while thoughtful updates create a seamless blend of historic character and contemporary luxury. At the heart of the home is a magnificent, all-new kitchen with exquisite hand-selected quartz countertops, custom cabinetry, and top-of-the-line appliances. The generous floor plan offers gracious spaces for everyday living and entertaining, including a formal dining room, butler’s pantry, breakfast area, expansive screened porch overlooking the Hudson, and versatile spaces ideally suited for home offices or studies. All nine bedrooms are beautifully appointed, while the luxurious primary suite features a spacious ensuite bathroom with high-end finishes, a walk-in closet with custom built-ins, a meditative sitting room, a wood-burning fireplace, and a Juliet balcony with spectacular water views. New windows were recently installed complementing the home’s thoughtful updates, including beautifully refinished wood flooring, a reverse-osmosis water filtration system, and an eero mesh Wi-Fi system providing seamless whole-home connectivity. A sophisticated climate-control system with 17 HVAC zones provides year-round comfort throughout and a generator offers added peace of mind. A three-car garage, upper-level laundry, and expansive driveway add modern convenience. With direct access to the Old Croton Aqueduct and close proximity to Patriots Park, Wilson Park, Tarrytown Lakes, Tarrytown, and Sleepy Hollow, Whitehall is an unparalleled private Hudson River oasis offering a lifestyle of extraordinary beauty, privacy, and distinction.

57 Cobb Lane, Tarrytown

$2,750,000

4 Beds ⋅ 6 Baths ⋅ 1048807 MLS

This award-winning, architect-designed masterpiece is beautifully set on over four acres of professionally landscaped grounds in a private North Salem cul-de-sac, with seasonal views of the Titicus Reservoir. Timeless Shingle-Style Victorian architecture is complemented by exceptional craftsmanship and thoughtful custom details throughout. The gracious, sun-filled interior features 10-foot ceilings, solid wood doors and custom moldings, inlaid hardwood flooring, transom windows, French doors, and two fireplaces. Elegant formal living and dining rooms provide beautiful spaces for entertaining, while the gourmet kitchen serves as the heart of the home. Generously proportioned living spaces offer exceptional versatility for everyday living, entertaining, working from home, and gatherings. The finished walk-out lower level, complete with a built-in bar, further expands the home's entertaining space and opens directly to a spectacular outdoor retreat. Surrounded by lush, park-like grounds, the heated in-ground pool and spa with a waterfall edge create a private, resort-like setting—perfect for morning coffee, afternoon swims, and evenings spent entertaining under the stars. From its distinctive architecture and fine craftsmanship to its privacy and breathtaking grounds, this exceptional residence captures the essence of sophisticated country living. Peaceful and private, yet conveniently located near Metro-North, schools, shopping, dining, and major commuting routes, this is a rare opportunity to enjoy the very best of North Salem.

4 Little Mountain Road, North Salem

$849,000

4 Beds ⋅ 3 Baths ⋅ 1046525 MLS

Welcome home to Apple Hill. This center hall colonial is set on more than an acre of level grounds in a cul-de-sac where space, comfort, and thoughtful improvements come together beautifully. The cul-de-sac provides privacy, quiet and a sense of security. Inside, recently refinished hardwood floors bring warmth to the living and dining rooms, while fresh paint and natural light create a bright, welcoming feel. The remodeled kitchen is the heart of the home, with new cabinetry, quartz countertops, a coordinating backsplash, and tile flooring that flows through the entry hall. Beyond what you see, there's comfort in knowing much of the important work has already been done: a newer roof, central air, three-zone hot-water baseboard heat, newer hot-water heater, a whisper-quiet water pressure pump, updated gutters and downspouts, and septic improvements. Outside, a large Trex deck invites morning coffee and summer dinners, while the above-ground pool and expansive level lawn create a backyard made for long days outdoors. Upstairs, has a practical layout with the primary suite to the right. It includes both a walk in closet and a standard closet for all your storage needs. The primary bath has both a soaking tub and standing shower. The hall bathroom has a tub/shower combo. The additional 3 bedrooms are all generously sized with just the right amount of natural sunlight. Thoughtful conveniences, including attic storage, a traditional laundry chute, central vacuum, hardwired fire and security system, storage shed with circuit breakers, and garage-door upgrades, make everyday living that much easier. Warm, welcoming, and thoughtfully improved, this is a home ready to be lived in and enjoyed from day one.

5 Rome Court, Cortlandt Manor

778 Sleepy Hollow Road, Briarcliff Manor

$9,750,000

6 Beds ⋅ 8 Baths ⋅ 1029073 MLS

Welcome to 778 Sleepy Hollow Road, an extraordinary custom Colonial estate nestled on 10.72 private acres in the heart of Briarcliff Manor. Originally built in 1996 and extensively renovated with uncompromising attention to detail, this exceptional residence seamlessly blends timeless elegance with today’s most sophisticated luxury amenities. The estate was also featured in Netflix’s The Diplomat, adding to its distinctive appeal and cinematic presence. Boasting 6 spacious bedrooms, 6 full bathrooms, and 2 half baths, this magnificent estate offers an unparalleled lifestyle. A grand approach leads to beautifully designed interiors featuring exquisite craftsmanship, sun-filled living spaces, and state-of-the-art technology throughout. The spectacular chef’s kitchen has been completely redesigned with premium finishes and top-of-the-line appliances, while every bathroom has been luxuriously remodeled, including elegant Japanese smart toilets. A distinguished mahogany-paneled study, featuring rich mahogany walls and ceiling, provides an elegant and sophisticated setting for work or private retreat. The stunning primary suite serves as a private sanctuary, complete with a breathtaking spa retreat featuring a hot tub on the terrace overlooking the iconic Manhattan skyline—creating the perfect setting to unwind while enjoying unforgettable sunsets. Designed for both grand-scale entertaining and everyday living, the home features a fully renovated lower level with an impressive entertainment lounge and custom bar, acoustically designed home theater, professional home gym, and beautifully updated mudroom. Five automatic Mendota fireplaces add warmth and ambiance throughout the residence. Outside, the resort-style grounds rival those of a private country club. Enjoy a spectacular swimming pool with pool house, tennis court, guest cottage, expansive terraces, and meticulously landscaped grounds offering complete privacy. A six-car garage provides abundant space for collectors and enthusiasts alike. No detail has been overlooked in the extensive capital improvements, which include a sophisticated Lutron lighting system, automatic custom draperies, a state-of-the-art Bowers & Wilkins sound system, Honeywell Vista 128 security system, 32-camera surveillance system, 2N Verso gated entry with keypad and vehicle camera monitoring, all-new windows and doors throughout the home, updated designer lighting, custom cast-iron staircase railings, new well water filtration system, and countless additional enhancements. An exceptional advantage of this remarkable property is its Mount Pleasant taxes while enjoying a prestigious Briarcliff Manor address, along with the unique opportunity to choose between the Pocantico Hills or Briarcliff Manor school districts. This is a rare offering where timeless architecture, cutting-edge technology, resort-caliber amenities, and one of Westchester County’s most desirable locations come together to create an estate unlike any other.

778 Sleepy Hollow Road, Briarcliff Manor

$1,350,000

3 Beds ⋅ 3 Baths ⋅ 1017900 MLS

Welcome to 16 Stephen Drive, beautifully situated on .40 acres along a wide, picturesque street in the desirable Pennybridge neighborhood in Tarrytown, NY. This classic center hall Colonial offers generous space throughout in a wonderful setting with an exceptional backyard. A proper entry foyer sets the tone, opening to a gracious living room with wood-burning fireplace and a formal dining room. Continue through to the heart of the home, where the open, dine-in kitchen features crisp white cabinetry, granite countertops, a Thermador range, Thermador refrigerator, breakfast bar and plenty of room for casual meals. A sliding glass door opens directly to the backyard patio, creating an easy connection to the heated pool and outdoors. Just beyond the kitchen, a cozy, tucked-away family room offers another comfortable place to unwind, while the side-entry mudroom with laundry and storage makes everyday living easy. Upstairs are three spacious bedrooms, including a generous primary suite with a bright, expansive primary bath with double vanity, large whirlpool style tub, and excellent closet space. Hardwood floors throughout, crown molding, wainscoting and two-zone central air add to the home’s classic appeal. Outside is where this property truly shines. The expansive, fully fenced backyard feels like a private retreat, complete with an in-ground heated pool and sport court. Backyard pickleball anyone? There's plenty of room to play and entertain, this is the yard where everyone gathers. An oversized two-car garage, connected to the mudroom by a covered breezeway, provides even more room for cars, bikes, gear and storage. All this in the Irvington School District, with Tarrytown’s vibrant shops, restaurants and waterfront close by. Enjoy Tarrytown recreation opportunities (tennis, pool, fitness center, parks), plus resident train parking and a 40-minute weekday express to Grand Central, while the nearby Old Croton Aqueduct trail offers miles of nature just moments from home. A special opportunity to bring your vision to a home with the space, setting and location you have been waiting for.

16 Stephens Drive, Tarrytown

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

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