Homes for Sale with a Pool in Westchester, NY

There are homes… and then there are places that feel quietly set apart from the world around them. Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally… like a secret meant only for those who understand what true luxury feels like. This is not just a home. This is a legacy estate. Set perfectly between the Hudson River and Sleepy Hollow Country Club, the location offers the rare balance today’s buyers search for privacy, proximity, and prestige. Minutes to Metro North, fine dining, boutique shopping, and everything that defines Westchester luxury living… yet once you arrive, the outside world seems to soften. There is a stillness here. You feel it walking the grounds, where mature trees frame rolling lawns and sunlight filters through in that unmistakable golden way. There is a rhythm to the property… the kind that invites long mornings on the porch, quiet afternoons by the pool, and evenings that stretch just a little longer than planned. And somewhere within it all… life quietly thrives. Bees drift from bloom to bloom, tending to the landscape in a way that feels both timeless and grounding… a subtle reminder that this estate is not just maintained, it is alive. Inside, the home unfolds with a level of craftsmanship and scale rarely seen today. Five ensuite bedrooms offer both privacy and comfort, anchored by a truly exceptional primary suite with its own fireplace, spa like bath, expansive dressing room, and a private sleeping porch… a nod to a more romantic era of living, where fresh air and slow mornings were part of everyday life. The kitchen is designed not just for cooking, but for gathering… a chef’s workspace complemented by a generous butler’s pantry, ideal for seamless entertaining. It flows effortlessly into a formal dining room that feels pulled from the pages of a design magazine, where hand printed Zuber wallpaper and a fireplace create a setting that is both refined and deeply inviting. Every room tells a story. A wood paneled office with its own fireplace opens to the front porch, offering a work from home experience that feels anything but ordinary. The living room, wrapped in double walls of French doors, blurs the line between indoors and out, filling the space with natural light throughout the day. Nearby, the sunroom becomes its own retreat… a place to pause, unwind, and simply take in the beauty of the property. Step outside, and the estate continues to reveal itself. A gunite pool set within manicured grounds. Multiple porches designed for every mood and moment. A historic Lord and Burnham greenhouse… a rare and remarkable feature that speaks to the property’s heritage. And a four plus car garage with a private apartment above, offering flexibility for guests, extended stays, or staff. This is Westchester luxury real estate at its finest, where historic architecture meets modern lifestyle, where privacy meets convenience, and where every detail has been thoughtfully considered. Because the truth is… You can always renovate a home. But you cannot recreate land like this. You cannot replicate this setting. And you cannot manufacture the feeling this property gives you the moment you arrive. 36 Revolutionary Road is not just being listed. It is being offered.

36 Revolutionary Road, Briarcliff Manor

$2,375,000

5 Beds ⋅ 3 Baths ⋅ 980144 MLS

WILLOW FARM. Pristine Pre-Revolutionary Farmhouse. A Barrett Family homestead dating to 1750. Expanded in the 1930’s, with the addition of a handsome stone wing. Interior spaces replete with original details -- spectacular wide-plank floors, vintage millwork, built-in cupboards, windows salvaged from the old Katonah Library and three fireplaces. Beautifully proportioned Living Room with fireplace, ceiling beams, plaster walls and antique bow window. Formal Dining Room with American Chestnut floor. Beautifully renovated Kitchen with custom cabinetry, marble counters and high-end appliances. Breakfast Area with spectacular antique window. Family Room with fireplace and pond view. Choice of Offices for working remotely. Private Primary Suite with exposed beams, fireplace, Dressing Room and Bath. Two additional Bedrooms. Renovated Hall Bath. Located on a quiet country road, six bucolic acres with gorgeous open property, spectacular plantings and gardens and two scenic ponds. Private Swimming Pool. Separate Guest Cottage. Detached Garage with Guest/Office Suite. Two Antique Storage Barns. Conveniently close to the village of Katonah, the Metro North train and commuting arteries. A fabulous country retreat and truly special offering!

95 Croton Lake Road, Katonah

$3,500,000

5 Beds ⋅ 6 Baths ⋅ 984817 MLS

Two homes, one gorgeous estate. This exceptional property features two distinct residences—a stunning modern new-construction main home and a charming, fully renovated 2 bedroom cottage—situated together on a picturesque, private estate. Modern and European-inspired, this residence balances scale with sophistication. Thoughtfully crafted to blend clean architectural lines with warm, natural materials, the home features 10-foot ceilings on the main level, a dramatic 12-foot great room, and vaulted ceilings on the second floor that create an airy, light-filled atmosphere throughout. The interior is finished with wide-plank walnut floors, custom millwork, and a curated mix of shiplap and reclaimed beams, lending richness and character at every turn. The kitchen serves as the heart of the home, featuring refined white cabinetry, quartz countertops, an expansive center island. The primary suite is a private retreat with a spa-like ensuite and walk-in closet, while each additional bath is appointed with heated floors and custom finishes. An unfinished, above-grade lower level with nine-foot ceilings provides 1,500 square feet of potential for future expansion, accompanied by a separate 800-square-foot bonus space perfect for an office, studio, or recreation room. Completing the estate is a delightful, fully renovated 861 square foot, two-bedroom cottage with its own 2 car garage. Offering total independence, it serves as the ideal setup for guests, extended family, or a dedicated home office, adding incredible versatility to the property. Exterior details are equally compelling, featuring Hardie siding, a striking engineered slate roof, and oversized European windows. The grounds are designed for leisure, with bluestone patios, professional landscaping, a full irrigation system, and a heated gunite pool framed by stonework. A semi-circular pergola with open beams serves as a unique architectural focal point, perfectly positioned to enjoy the exterior side of the home’s double-sided fireplace—the ideal setting for intimate evenings and effortless entertaining. Located just minutes from top-rated schools, local shopping, and outdoor gems like Bedford Village Memorial Park and the Ward Pound Ridge Reservation, this estate offers the perfect balance of privacy, luxury, and convenience. Total (taxable living area) square footage includes the cottage square footage.

515 Long Ridge Road, Bedford

$3,995,000

5 Beds ⋅ 6 Baths ⋅ 823299 MLS

Behind private gates, nearly six acres of bucolic countryside unfold around a spring-fed lake — a setting that feels worlds away, yet sits just one hour from Manhattan. Gut-renovated to the studs and reimagined from the ground up, this Pound Ridge estate blends Mid-Century Modern design with original stone construction and hand-hewn beams — a rare marriage of architectural integrity and contemporary refinement. The result is a home that feels both timeless and entirely of the moment. The main residence offers four bedrooms and has sweeping water views that define the property. A detached guest studio with two-car garage provides flexible accommodation for visitors or staff, while the heated gunite pool and pool house — complete with full bath, wet bar, and huge fireplace — create an effortless setting for both quiet evenings and elevated entertaining. An additional detached two car garage rounds out the offering. Outside, the grounds have been as thoughtfully curated as the interiors: new landscaping, artisan stonework, full irrigation system, patios, and mature tree work frame the lake and connect seamlessly to the Pound Ridge Land Conservancy — a permanent buffer that ensures the privacy and natural beauty of this property endure. Canoe and Kayak directly from the property! Truly turnkey. Completely one-of-a-kind.

39 Old Snake Hill Road, Pound Ridge

$1,150,000

4 Beds ⋅ 4 Baths ⋅ 979838 MLS

ATTENTION BUILDERS, CONTRACTORS & PROJECT SEEKERS: This is a major renovation project being sold strictly AS-IS, presenting an incredible opportunity to rebuild massive sweat equity in a prime Katonah location. Set high on nearly 5 private, wooded acres offering sunset views and total serenity, this multi-level compound-style property needs a significant amount of work, updates, and TLC throughout, but possesses the bones to be an absolute showstopper. The main residence features 4 bedrooms and 3.5 baths spread across a highly versatile layout. Maximizing the ultimate value of this property are two detached bonus structures: a pool house and a separate guest cottage, both requiring substantial rehabilitation but offering unmatched versatility for a home business or studio. Complete with a Wellis swim spa pool (needs service/inspection) and just moments from Katonah Village, Yorktown Heights, shopping, highways, and the Metro-North train, this is a heavy-lift property meant for those with the vision, crew, and resources to execute a major transformation. Bring your contractor and your imagination!

37 Mekeel Street, Katonah

$4,995,000

8 Beds ⋅ 8 Baths ⋅ 982066 MLS

Set at the end of a private cul de sac within the highly coveted Edgemont School District, this exceptional estate offers a rare opportunity to reimagine one of the largest and most architecturally significant homes in the area. Spanning approximately 14,700 square feet and set on nearly three private acres, the residence is defined by soaring cathedral ceilings, dramatic double height spaces, and an extraordinary use of glass that fills the home with natural light. A grand entrance introduces a series of expansive living and entertaining rooms that seamlessly connect to a stunning courtyard centered around an in ground pool, creating a striking indoor outdoor setting that is both private and serene . The layout offers remarkable flexibility with multiple living wings, a first floor primary suite, generous guest accommodations, and an upper level with spacious bedrooms and additional areas for recreation, work, or wellness. A substantial unfinished lower level offers significant additional square footage and a compelling opportunity for customization. Recent enhancements include a renovated pool, integrated smart home features, and a newly constructed wine cellar. The grounds are equally impressive, offering expansive lawns, mature landscaping, and a sense of scale and privacy rarely found in Edgemont . This is a true estate offering with extraordinary potential, providing the rare chance to create a bespoke residence of exceptional size, presence, and distinction just thirty minutes from Manhattan.

2 High Point Terrace, Scarsdale

$4,395,000

4 Beds ⋅ 5 Baths ⋅ 986698 MLS

Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for both everyday living and entertaining. High ceilings, unique designer chandeliers, and a marble fireplace framed by expansive windows create a dramatic yet inviting ambiance. The primary suite is a private retreat, complete with a serene seating area, walk-in closet, and spa-inspired bath with soaking tub and his-and-hers sinks. The top-floor laundry room ensures effortless convenience, while the fully finished basement boasts a gym, media/recreation room, full bath, and direct walk-out to a covered patio with speakers and ceiling fans. Outdoors, an entertainer’s dream awaits: a stunning in-ground pool and hot tub with a glass railing, outdoor kitchen, fire pit lounge, and professionally landscaped grounds with Kentucky bluegrass sod and Thuja trees, creating your own private oasis. This home has been extensively updated with new roofing, siding, windows, flooring, systems, and high-end finishes, combining elegance with modern functionality. Every element has been thoughtfully curated to offer a posh lifestyle, flawless entertaining, and refined daily living. Nestled within the prestigious Pine Hill Estates, this home offers access to the highly rated Katonah-Lewisboro School District. Commuting is effortless, with close proximity to major highways and multiple Metro-North stations, providing convenient access to New York City and surrounding areas. Beyond the home's luxurious features, the location offers a wealth of recreational opportunities. Just a short drive away, Ward Pound Ridge Reservation, Westchester County's largest park, provides over 4,300 acres of natural beauty. Enjoy hiking, fishing, and camping amidst scenic landscapes and diverse wildlife. For shopping and dining, Ridge Hill is nearby, offering a variety of retail stores, restaurants, and entertainment options. Additionally, Untermyer Gardens Conservancy and Lenoir Preserve offer tranquil settings for nature walks and exploration. This residence is not just a home; it is an elevated lifestyle of comfort, convenience, as well as curated leisure and recreation. Seize the opportunity to make it yours today!

45 Pine Hill Drive, South Salem

$998,000

5 Beds ⋅ 6 Baths ⋅ 984886 MLS

Auction Pricing. All qualified bids over asking will be considered, Tucked away in the picturesque village of Dobbs Ferry, this expansive residence effortlessly combines comfort, flexibility, and timeless appeal. Encompassing more than 3,700 sq ft on nearly one private acre, this property is a rare opportunity to create your forever home in one of Westchester’s most sought-after Rivertowns. Inside, you’ll find five spacious bedrooms, five full baths, and a convenient main-level powder room, offering an ideal layout for large households and those who love to entertain. The generous floor plan provides a seamless flow between living, dining, and lounging spaces, perfect for both everyday living and memorable gatherings. A versatile lower level invites endless possibilities: imagine a recreation room, home gym, studio, or private guest suite, the choice is yours. The oversized driveway easily accommodates multiple vehicles, making hosting effortless. With its generous proportions, solid bones, and limitless potential for customization, this home invites you to bring your vision to life. Set just minutes from downtown Dobbs Ferry, residents enjoy access to award-winning schools, Metro-North service to Manhattan, charming shops, vibrant dining, and the scenic Hudson River parks that define Rivertown living. Discover the space to grow and the freedom to dream, schedule your private showing today.

5 Forkland Lane, Dobbs Ferry

$4,500,000

6 Beds ⋅ 6 Baths ⋅ 978126 MLS

Buxton Pond Farm, tucked quietly along a country Lane just minutes from the train, shops and schools of Bedford Hills, is a rare offering. Set on 11 pastoral acres surrounded by historic stone walls with sweeping lawns, mature trees, established gardens that grow food and flowers, and open pastures for animals, this beautiful farm offers a lifestyle rooted in nature, security, and sustainable living. At the heart of the property stands a graciously preserved Colonial residence, rich in character and warmth with 6 bedrooms, 5 full bathrooms, 1 powder room, wide-board pine floors and original fireplaces. The grounds are a sanctuary of their own. The main home is complemented by a remarkable collection of historic outbuildings including a barn with a two bedroom residence for staff, guests or extended family, a greenhouse, an antique chicken house, a pond, and a stunning pool, creating a true compound designed for gathering, growing, and generational living. This enchanting estate captures the essence of Bedford's timeless beauty, where sweeping open lawns and distinguished Colonial architecture come together to create an unparalleled sanctuary of elegance and tranquility, all just minutes from the 87-acre Buxton Gorge Preserve. A legacy property of enduring grace, just 40 miles from Manhattan.

161 Buxton Road, Bedford Hills

$9,750,000

8 Beds ⋅ 12 Baths ⋅ 973726 MLS

Longmeadow, nestled in the heart of Irvington’s prestigious Matthiessen Park, is a true showstopper — a timeless example of Hudson River grandeur. Majestically set on 12 sweeping acres of lush, open grounds, this extraordinary estate captures the full splendor of its idyllic surroundings. With commanding views of both the rolling landscape and the tranquil waters of the Hudson, Longmeadow offers a setting that is nothing short of breathtaking. Painstakingly restored and thoughtfully reimagined, the home masterfully blends classic architectural elegance with a sophisticated modern aesthetic. Inside, the interiors exude an effortless sense of luxury — cool, comfortable, and undeniably striking. Every detail has been curated to elevate the experience of everyday living, from the soaring ceilings to the perfectly scaled rooms that seamlessly transition from formal to relaxed. Spanning over 11,000 square feet across four expansive levels, the residence is both grand in scale and intimate in feel. At its heart are eight beautifully appointed en-suite bedrooms, each designed as a private sanctuary, along with twelve bathrooms finished to the highest standard. A dramatic 30-foot interior gallery anchors the home, connecting a series of stunning public rooms that are equally suited for grand entertaining or quiet reflection. A defining highlight of the first floor is the breathtaking loggia, opening to a 100-foot west-facing terrace that frames unobstructed river views. From here, an elegant staircase cascades down to the manicured gardens — an exquisite extension of the home’s architectural beauty. The lower level offers a fully immersive lifestyle experience, with dedicated areas for recreation, fitness, and entertaining. Enjoy expansive playrooms, a state-of-the-art gym, a summer kitchen, and a full bath — all leading to the crown jewel: a 21-foot heated indoor pool, offering a resort-quality escape year-round. Just 25 miles from Midtown Manhattan, Longmeadow offers the rare combination of total privacy and immediate access to city life. The charming village of Irvington — with its boutique shops, vibrant dining scene, and riverfront parks — is just a short stroll away. A once-in-a-lifetime offering, Longmeadow is an estate where timeless beauty meets modern luxury, and every amenity is crafted to deliver an unparalleled lifestyle. With guest quarters, a private dressing area, and garage parking for four or more cars, this is truly a legacy property unlike any other.

2 Fargo Lane, Irvington

$11,500,000

5 Beds ⋅ 7 Baths ⋅ 823682 MLS

Originally designed in 1925 by renowned architect Lewis Bowman, this extraordinary residence has been meticulously reimagined by Lucio DiLeo of Studio RAI Architects and its current owners through a comprehensive, four-year, world-class renovation. Seamlessly blending timeless architectural beauty with modern luxury, this nearly 9,200 SF masterpiece is defined by exquisite design, fine craftsmanship, and resort-style amenities. Set back along a private drive, the home’s stately facade gives way to a world of refined elegance. Stone steps wind toward an enchanting terrace and a glass-enclosed loggia, opening into interiors that are nothing short of breathtaking. A dramatic, balconied foyer overlooks a grand living room featuring a 14-foot soaring beamed ceiling, striking Palladian windows, and an imported 7x6-foot limestone fireplace, setting the tone for the extraordinary quality found throughout the home. The formal dining room, wrapped in silk-lined walls and centered around a second fireplace, is both luxurious and welcoming—ideal for elegant entertaining or intimate gatherings. Every inch of this residence reflects a deep commitment to artisanal detail and exceptional materials. At the heart of the home is a chef’s dream kitchen—bright and expansive, with a stunning barrel-arched ceiling and views of the rear gardens. A 12-foot island with a champagne sink, natural quartz countertops, and top-of-the-line appliances—including a La Cornue Grand Palais 180 range, La Cornue Flamberge rotisserie, Blue Star electric oven with pizza stone, Miele fridge and freezer, steam and speed oven, and separate coffee station—creates the ultimate culinary experience. A custom Vaclav brass and pewter hood, custom cabinetry by Nils Kasperson, a large pantry with an ice maker, a kitchen office, and a fully outfitted mudroom add both beauty and function. Flowing seamlessly from the kitchen, the spectacular Great Room is the home’s showpiece—anchored by a dramatic stone fireplace and enhanced by custom wood beams, a full built-in entertainment wet bar, bespoke built-in shelving, an 82-inch hidden drop-down TV, and state-of-the-art AV. Adjacent is a light-filled breakfast/dining room surrounded by Palladian windows that open to a private terrace with its own fireplace—perfect for al fresco dining and quiet evenings. Upstairs, five luxurious bedroom suites (easily convertible to six) each offer en-suite baths with steam showers, walk-in closets, AV systems, and custom built-ins. The primary suite is a serene retreat featuring a cathedral ceiling, private balcony, soundproof linen walls, a hidden 65-inch TV, and a lavish spa bath with radiant-heated floors, gas fireplace, soaking tub, and steam shower. Included in the 9,200 SF is 3,000 SF of upper- and lower-level, fully permitted space with infrastructure in place to build out a myriad of amenities such as a home gym, golf simulator, game room, home office, wine room, and more. The estate’s outdoor spaces are equally impressive, replete with endless stone walls and bluestone patios throughout. Designed for entertaining on a grand scale, the grounds feature a 42-foot heated pool and spa, a 70x60 sports court, multiple Lynx grill stations, expansive dining and lounge terraces, koi ponds, a secret garden with a swing, two cozy fireplace terraces, and ample space for a massive party tent. A fully automated Savant/Lutron lighting, AV control, and surveillance system ensures comfort and security in this private paradise. Completing the estate is a temperature-controlled, customized two-car garage with 11-foot ceilings outfitted for two auto lifts to accommodate two SUVs and two sports vehicles, plus additional driveway parking for eight vehicles—providing a total of 12 parking spaces. Set in a quiet, exclusive enclave just minutes from Bronxville village and a quick commute to Manhattan—all in a community celebrated for its top-rated schools and exceptional quality of life.

47 Masterton Road, Bronxville

$7,995,000

6 Beds ⋅ 7 Baths ⋅ H6317077 MLS

A rare opportunity to own one of Westchester Country Club’s most elegant estates- a completely renovated, move-in ready 1926 Tudor that effortlessly marries storybook charm with modern luxury. Boasting over 8,500 square feet of masterfully renovated living space, this residence seamlessly blends historic architectural character with modern sophistication, offering a rare opportunity for refined suburban living. Enter through a grand foyer into formal living spaces defined by intricate millwork, elegant arches, leaded glass windows, and Rumford fireplaces. The spacious dining room flows effortlessly into a designer chef’s kitchen, featuring custom cabinetry, marble countertops, a Wolf six-burner range with pot filler, a Sub-Zero refrigerator/freezer, and a built-in pantry. The massive teak center island is ideal for entertaining, complete with a Sub-Zero wine refrigerator and cooling drawers. Adjacent, the expansive family room is bathed in natural light, with custom woodwork and a grand fireplace, overlooking serene estate grounds. The private primary suite is a sanctuary of luxury, with high ceilings, a fireplace, custom closets, and a spa-inspired bath with radiant heated floors, tumbled marble, soaking tub, steam shower, and dual vanity. Additional bedrooms are generously sized with high ceilings and elegant finishes, complemented by beautifully appointed baths. The lower level offers a world-class retreat, including a well-equipped gym, custom wine room, an additional bedroom, two full baths with direct pool access, and abundant storage. Outdoor living is equally spectacular, with an expansive patio, in-ground pool, and meticulously maintained grounds framed by the estate’s timeless slate roof and copper gutters. A three-car garage with a bonus/media room completes this extraordinary property. Located in one of Westchester’s most desirable enclaves, 19 Park Drive South provides unparalleled privacy, proximity to world-class amenities, and effortless access to New York City via Metro-North and major parkways. Whether enjoying the serene estate, hosting elegant gatherings, or taking advantage of the Westchester Country Club’s prestigious grounds, this home embodies the ultimate luxury lifestyle.

19 Park Drive S, Rye

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

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