Homes for Sale with a Pool in Westchester, NY

778 Sleepy Hollow Road, Briarcliff Manor

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

$7,995,000

6 Beds ⋅ 9 Baths ⋅ 1017441 MLS

The Definition of Luxury. Designed Without Compromise. Made for Extraordinary Living. Built by MXN Development in collaboration with renowned architect Teo Siguenza and distinguished Landscape Architects Benedek & Ticehurst. Expertly crafted and designed with incredible detail, when every detail matters. Hand Selected Stone & Lap Siding, Vermont Slate Roof, and Architectural Windows. First floor 10' Ceilings, 9'+ on Second, and 9’ in the lower level. Chefs Kitchen, Concealed Walk-In Pantry w/Appliance Bar, Two Home Offices, and endless details throughout. Luxurious master suite with couture-inspired closets and bespoke marble clad bathroom. Four additional en-suite bedrooms on the second floor. Equinox inspired Gym with Infrared Sauna, Cold Plunge, Himalayan Salt Room w/Red Light Therapy and Steam Shower. Expansive lower level recreation area with built in bar and glass wine enclosure. Additional Ensuite Bedroom. Advanced Smart Home Automation including Sonos, state of the art Security System w/Cameras, WiFi Lighting + HVAC and so much more. Infrared Heated covered porch w/fireplace, TV and outdoor kitchen. In-ground Salt Water Pool with Auto Cover Included. Expansive bluestone patio and entirely flat yard. Radiant Heated Garage with lift capacity for 6 cars. Elevator ready w/access to all 3 floors. The most impressive new construction opportunity available located within coveted Sterling Ridge. Why Settle for Anything Less. Estimated Completion Summer 2027. Buyer pays NYS transfer tax.

113 Woodlands Road, Harrison

$2,900,000

5 Beds ⋅ 5 Baths ⋅ 1037090 MLS

Set behind stone pillars at the end of a meandering private drive, this custom-built stone manor draws its inspiration from a 19th-century English manor house. This home features a rare blend of Old World craftsmanship and modern-day comfort on more than four private, lushly landscaped acres, just about an hour from New York City. Built in 1988 and thoughtfully updated since, the residence features Five fireplaces anchor the home's principal rooms. The living room, a soaring 39' x 24' space with 12' coffered pine ceilings and a massive floor-to-ceiling stone fireplace, sets a formal yet inviting tone, while the library's built-in cabinetry and Art Deco lighting bring a warmer, more contemporary counterpoint. The gourmet kitchen is a true tour de force, outfitted with Neff cabinetry, Viking appliances, and its own floor-to-ceiling stone fireplace. A library with French doors opens directly onto a stone terrace, ideal for quiet mornings or evening entertaining. Upstairs, the primary suite is accessed through a generous sitting room/office with its own fireplace and continues into a bedroom with a tray ceiling and another fireplace, as well as a dressing area with a lovely walk-in closet and a spacious primary bath. Three additional bedrooms and a bath complete the sleeping quarters. Outdoors, the grounds are just as considered as the interiors: an oversized heated gunite pool and spa, surrounded by extensive stone terracing, formal and English gardens, and manicured lawns. The detached three-car garage includes a heated guest, staff, or au pair suite with a full bath, offering flexible space for visitors, live-in help, or a private studio/office. Notable amenities include marble and granite finishes throughout, gleaming hardwood floors, and 9' and 12' ceilings. Every detail reflects a home that was built without compromise and maintained the same way. Zoned for the highly regarded Katonah-Lewisboro School District, including Meadow Pond Elementary School, John Jay Middle School, and John Jay High School, this is a rare offering for buyers seeking a full-time residence or a refined weekend retreat within easy reach of Manhattan.

295 Salem Road, Pound Ridge

$1,780,000

4 Beds ⋅ 4 Baths ⋅ 1044050 MLS

Welcome to this beautifully maintained almost 3000 sq ft 4 bedroom 4 bath Colonial set on a private, sun-filled one acre property framed by mature trees, a classic stone wall , and meticulously maintained landscaping and plantings. Elegance and craftsmanship are evident throughout with beautiful hardwood floors, generously sized bedrooms and a primary suite with private en-suite bath. At the heart of the home, the kitchen opens to an inviting sitting room with a gorgeous stone fireplace and double doors leading to a seamless indoor-outdoor living experience. The finished walkout lower level offers exceptional additional living and entertaining space, complete with a bathroom and built-in ceiling speakers (with surround sound), plus direct access to the grounds and pool area. Outside, enjoy your own private retreat featuring a 40' X 16' heated in-ground fiberglass pool with sunning deck and full Certificate of Occupancy along with a new patio and fire pit under the deck. The pool is professional maintained weekly, and the propane tanks for the pool heater were recently filled. Additional improvements include a freshly painted exterior and deck (August 2026), new hot water heater and refrigerator (2024), septic cleaning (June 2026)and an EV charging port in the two-car garage. There is an alarm system in place. Thoughtfully maintained and move-in ready, this home combines timeless craftsmanship, modern conveniences, and resort-style indoor-outdoor living in a beautiful and private setting.

406 Bedford Road, Chappaqua

$15,995,000

8 Beds ⋅ 13 Baths ⋅ 1036802 MLS

The Bluffs at Premium Point represents a once-in-a-generation opportunity to acquire one of the most significant waterfront estates on Long Island Sound in the award-winning Mamaroneck school district. Set on 1.3 acres at the crest of Premium Point’s coveted 24-hour guard-gated peninsula, this newly completed residence commands extraordinary 360-degree views across the Sound and Premium Mill Pond. One of the enclave’s landmark “Big Four” properties, it offers an irreplaceable combination of scale, privacy, elevation, water frontage and proximity to Manhattan. Built by Cum Laude Group, one of Westchester’s premier luxury builders, the residence reflects an uncompromising commitment to craftsmanship, materials and execution. Portions of the original stone estate remain within its footprint, while a new slate roof, copper gutters, and entirely new systems, finishes and surfaces bring modern refinement and full builder warranty. More than 13,000 square feet of beautifully finished living space unfolds across multiple elevator-served levels, with eight bedrooms, 10 full and three half baths, a heated and cooled three-car garage, pool house/guest suite and dedicated fitness level. Walls of glass, expansive Marvin windows, high ceilings, white oak floors, sculptural stairways and custom millwork frame sweeping water views from nearly every principal room. The main level is anchored by a dual-island chef’s kitchen with custom white oak cabinetry, dramatic marble surfaces, Wolf and Sub-Zero appliances, two Bosch dishwashers, extensive pantry storage and a sunlit breakfast bay overlooking the Sound. A separate butler’s pantry with wine refrigeration connects to the formal dining room, while the living and family rooms open through multiple sets of glass doors to expansive bluestone terraces and uninterrupted water views. The primary suite is a private retreat with panoramic Sound views, gas fireplace, two boutique-scale walk-in closets and a spa bath with steam shower, freestanding tub, and marble finishes. Additional ensuite bedrooms, a flexible office/guest suite, second-floor laundry, third-floor recreation room and private guest accommodations provide exceptional versatility for entertaining and extended stays. Outdoors, professionally landscaped architecture, a Belgian-block motor court, broad waterfront terraces, pool and spa, private neighborhood beach access, boat slips and a covered outdoor kitchen with Lynx appliances create a complete setting for waterfront living. The separate two-story pool house adds a guest suite, pool bath, dedicated laundry and dramatic custom gym. Infrastructure is equally impressive, including seven-zone high-efficiency HVAC, radiant heat in select areas, Lutron RadioRA 3 lighting, Sonos audio, commercial-grade network/WiFi, 400-amp electrical service, upgraded water and gas service, fire sprinklers, and whole-house generator. Rarely does an offering combine this caliber of construction, architectural finish, waterfront presence and privacy within a short commute to New York City. The collaboration of an irreplaceable Premium Point setting with the craftsmanship of Cum Laude Group elevates The Bluffs beyond even the exceptional. It is a legacy property in one of Westchester’s most tightly held enclaves, created for a buyer who recognizes that true luxury is ultimately defined by what cannot be duplicated. For those with the ability to choose among the finest homes in the world, this is the kind of property that stands apart not simply for its quality, but because opportunities of this caliber on this setting are seldom available at any price.

104 Premium Point, Mamaroneck

$1,700,000

4 Beds ⋅ 4 Baths ⋅ 1031198 MLS

This distinctive contemporary on 3.0 acres was originally built as a country weekend retreat and has been lovingly maintained by the same family for more than 30 years. Its architecture, generous entertaining spaces and exceptional outdoor amenities reflect the thoughtful craftsmanship of its era, while offering the next owner an opportunity to refresh and reimagine the interiors for today. The outdoor chef’s kitchen, bar, heated Gunite pool and expansive patios are thoughtfully positioned among natural rock outcroppings and lush landscaping on 3 acres. An abundance of privacy, flat usable land and multiple gathering areas create a relaxed country lifestyle designed for gatherings, and enjoying the outdoors. The first-floor layout lends itself to easy living and entertaining. The kitchen with bar seating creates the heart of the home, flowing naturally into the family room with fireplace and solid honey toned built-ins. French doors lead directly to the pool, extending the kitchen and living spaces outdoors. The large solarium, with three sides of glass, provides a wonderful setting for dining while taking in views of the surrounding landscape and pool. The formal dining room, with oversized windows, flows to the formal living room, two steps down and designed as a versatile multi-function space. A substantial fireplace is flanked by French doors opening to the side patio, while oversized windows and a dramatic beamed ceiling enhance the room’s architectural character. The first-floor ensuite primary bedroom is one step down and features two separate doors providing access to the large private rear stone patio, and to the side lawn and pool. Two additional steps down lead to a private office with custom cabinetry. The second floor includes an ensuite bedroom and two additional bedrooms share a full hall bath. The lower level offers multiple storage rooms, a 536 finished SF is currently used as a workout area, and a substantial wine storage room. The heated two-car garage is finished with a custom wall and flooring system. A distinctive property with exceptional outdoor amenities, thoughtful original craftsmanship and tremendous potential. Ideally positioned near the Bedford/Pound Ridge border, the property offers the convenience of Bedford with the relaxed country character of Pound Ridge.

55 Old Logging Road, Bedford

$4,395,000

5 Beds ⋅ 9 Baths ⋅ 1046026 MLS

Beautifully sited high above the Hudson river, this architectural masterpiece offers truly sweeping river views and views of the Manhattan Skyline across 14 private acres. Spanning approximately 11,130 square feet the residence seamlessly bends striking design with natural beauty, creating a one-of-a-kind retreat defined by space, light and unparalleled scenery. Designed by a celebrated Architect. Soaring 12' ceilings, floor to ceiling glass walls which bring the outdoors in. Extensive decking and terraces. Incredible flow from the entry to the living room, dining room, chefs kitchen, family room, library & library. 5 ensuite bedrooms on the second level including the primary suite with 28 foot ceiling height - 2 full baths and oversized walk in closets. The garden level has walk out access to the covered terrace and pool. The space features an oversized gym, media room, recreation room, 2 changing cabanas and an entertainment kitchen. Newly renovated tennis court on premises for Bramblebush residents use only. This home will capture your heart from the moment you entry through the gated entry and drive through the magnificent landscape. Minutes to Metro North and Highways. This is truly a work of art that you must experience.

18 Bramblebush Road, Croton-On-Hudson

$3,995,000

4 Beds ⋅ 3 Baths ⋅ 1036816 MLS

A truly unique and exceptional offering in the Village of Scarsdale, this magnificent hidden 5.86-acre country estate, owned by one family for more than 60 years, presents a rare combination of privacy, natural beauty, architectural character, and remarkable potential. Set atop a gently elevated knoll and directly abutting Saxon Woods Park and its miles of hiking trails, the property offers an extraordinary sense of seclusion while remaining conveniently close to Scarsdale’s renowned schools, transportation, recreation, major highways, village amenities and approximately 40 minutes from midtown Manhattan! At the heart of the property lies a distinctive 1950’s four-bedroom, three-bath open-planned windowed residence, designed by an apprentice of Frank Lloyd Wright and rich in period architectural details. Surrounded by mature trees, a grand front expanse, lush landscaping, and tranquil grounds, the home captures a unique mid-century spirit and provides an inspiring foundation for light renovations or a complete reimagining. An attached greenhouse adds further charm and possibilities for the discerning gardener or horticultural enthusiast. A separate one-bedroom, one-bath garage-attached cottage provides additional accommodations for guests, staff, extended family, or a private office or studio as well as a newly renovated in-law suite on the lower level. The grounds are an exceptional private retreat, featuring a swimming pool, tennis court, spring-fed meditation pond for summer fishing or winter ice skating, and an exclusive wooded area complete with a private hiking trail and opportunities for real woods exploration. Adding to the property's extraordinary appeal is its AA-1 zoning—currently the only remaining on-market large-acre property in the Village of Scarsdale with this designation—offering an unusually broad range of potential uses, subject to applicable approvals. Permitted possibilities include a private equestrian facility with a stable for up to four horses, school, assisted living facility, medical office, religious center, playground, private club or a private compound, with a two-acre minimum for the latter. Whether envisioned as a spectacular private estate, a thoughtful maintenance of its mid-century architectural heritage, or an entirely new creation, this extraordinary property offers an opportunity rarely found in Scarsdale. This is your rare opportunity to own a specialized home or create something truly exceptional on one of the Village's most distinctive and private parcels.

35 Saxon Woods Road, White Plains

$2,395,000

5 Beds ⋅ 7 Baths ⋅ 1041927 MLS

Set within one of New Rochelle’s most coveted waterfront enclaves, this distinguished brick and stone Center Hall Colonial offers an exceptional combination of architectural elegance, refined interiors, and an enviable waterfront lifestyle. Set on .47 acres of beautifully landscaped grounds, the property enjoys sweeping views of Long Island Sound, deeded beach rights, and exclusive access to a private pedestrian path reserved for Davenport Estates residents. Here, life unfolds at the water’s edge—spectacular sunsets, boats sailing past throughout the seasons, and Fourth of July fireworks enjoyed from the private beach. A gracious entry introduces beautifully proportioned rooms and an extraordinary level of craftsmanship. The formal dining room and elegant step-down living room with wood-burning fireplace set the tone for sophisticated entertaining. At the heart of the home, the open chef’s kitchen features high-end appliances including a built-in Miele coffee machine, wine fridge and two beverage fridges, and a separate breakfast area with the family room beyond. A conveniently located laundry room and full bath are just off the kitchen, along with direct access to the pool. The enclosed sunroom is a particular highlight, featuring skylights and expansive accordion glass doors that open completely to the patio and backyard, creating a seamless transition between indoor and outdoor living. The family room, distinguished by a skylight and double-sided gas fireplace shared with the adjacent media room, offers an inviting space for both relaxed gatherings and more formal entertaining. Throughout the home, bespoke details and luxurious materials include Brazilian cherry, teak, oak, and marble floors; mahogany doors; custom mantels and lighting; walk-in cedar closets; and a sophisticated surround-sound system. The serene primary suite is a private retreat, featuring a gas fireplace, two walk-in cedar closets, and a spa-like bath with Jacuzzi tub, steam shower, and double vanities. Four additional bedrooms and five-and-a-half additional baths provide generous accommodations for guests. The grounds are designed for both privacy and grand-scale entertaining. A circular drive introduces the property, while mature landscaping and hand-selected specimen plantings create a lush, secluded setting. The expansive backyard centers around a heated in-ground gunite pool and hot tub, with generous patio space and a beautiful lawn providing the ideal backdrop for summer entertaining or tranquil afternoons at home. Exceptional amenities continue throughout, including radiant-heated floors throughout most of the residence, a wine cellar, slate roof, copper gutters, and a heated two-car garage with epoxy floor conveniently accessed from the kitchen. The approximately 1,200-square-foot lower level includes a finished room, wine cellar, full bath, abundant storage, and direct access to the garage. Perfectly situated for convenience as well as privacy, the property is within walking distance of public elementary and middle schools and minutes from New Rochelle’s acclaimed dining, shopping, and Metro-North station (32 minutes to Grand Central Terminal). With no through traffic and a remarkable connection to Long Island Sound, this is a rare opportunity to experience an elegant waterfront lifestyle in one of New Rochelle’s most desirable communities.

50 Echo Bay Drive, New Rochelle

$7,950,000

6 Beds ⋅ 10 Baths ⋅ 1035246 MLS

MILLSBROOK. Foremost Upper Hook Road estate area. Sophisticated and refined Country House, circa 1938. Beautifully proportioned rooms impeccably appointed by renowned designer. Gleaming hardwood floors, impressive millwork, upholstered walls, French doors and three fireplaces. True Center Hall Entry with French doors to rear terrace. Stunning Living Room with crown dentil molding, bay window and fireplace. Mahogany Library with fireplace and Onyx wet bar. Formal Dining Room. Spectacular Chef’s Kitchen with Breakfast Area. Family Room with coffered ceiling and fireplace. Private First Floor Primary Suite with opulent Bath. Five additional Bedrooms. Lower Level with Professional Home Theater, Wine Cellar and Home Office Suite. Two Bedroom Guest/Caretakers House with Gym. Olympic length Swimming Pool. Fabulous stone and Mahogany Pool House with fireplace. Gated drive to over seven manicured acres. Gently rolling lawns, exquisite gardens, old stone walls and scenic, babbling brook. A truly rare opportunity!

29 Upper Hook Road, Katonah

$4,050,000

4 Beds ⋅ 4 Baths ⋅ 1044129 MLS

Welcome home to this charming Georgian Colonial, where bespoke elegance, timeless architecture, and beautifully landscaped grounds create an exceptional setting, sweetly situated behind a gracious circular driveway. A grand foyer welcomes you inside and leads to an extraordinarily spacious living room anchored by a wood-burning fireplace and thoughtfully designed for the display of fine art. The living room flows seamlessly into a family room of splendid proportions, creating an inviting setting for both everyday living and entertaining. Bathed in natural light, the refined dining room offers an elegant backdrop for gatherings. At the heart of the home is an incredible chef’s kitchen featuring stainless steel appliances and complemented by a private breakfast room. The private quarters unfold with the same sense of grandeur and attention to detail. The showstopping primary suite is a true retreat, complete with a generous dressing room and en suite bath. Three additional elegant bedrooms provide beautifully appointed accommodations, including a second-level bedroom with its own en suite bath. A bonus room on the third level offers flexible space to suit a variety of needs. The lower level provides even more versatility, with laundry, utilities, and bonus space ideal for a recreation room, home office, or additional flexible living space. Outside, the property is nothing short of an oasis. Sweeping panoramic sunset views provide a spectacular backdrop to the distinctive pool and patio, creating an idyllic setting for outdoor entertaining, quiet relaxation, and enjoying the beauty of the surrounding landscape. A two-car attached garage and long driveway provide ample parking and everyday convenience. With 4 bedrooms, 3.1 baths, gracious proportions, elegant details, flexible living spaces, and extraordinary indoor-outdoor living, this exceptional Scarsdale residence offers a rare combination of timeless sophistication and everyday comfort.

31 Griffen Avenue, Scarsdale

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

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