Homes for Sale with a Pool in Westchester, NY

Advanced Search Market Reports Home Value Connect

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.

< Back to all Homes for Sale in Westchester, NY

Search Westchester, NY by Lifestyle

All Homes for Sale with a Pool in Westchester, NY

$5,495,000

5 Beds ⋅ 7 Baths ⋅ 1010043 MLS

Rockridge is an extraordinary hilltop estate situated on one of the highest elevations in all of Bedford. Offering 25-mile panoramic vistas across The Hudson Valley to The Palisades of New York, the property is quite simply stunning. Gated, fenced, and accessed by a quarter-mile long driveway, the residence is perfectly sited on over 11 acres of spectacular rolling land. The house centers on a brand-new award winning Leicht kitchen. The great room with a massive stone fireplace is under an exposed beam and cathedral ceiling. The first floor primary suite is a private wing and includes separate walk-in dressing rooms and partner bathrooms. A wonderful outdoor salt-water pool shimmers amid pristine stone terraces ideally scaled for coffee, cocktails, dining and large scale entertaining. Separate from the main estate are a two-bedroom guest house, an apple and pear orchard and a raised bed vegetable garden. This is a rare and incredible opportunity to live the dream at your own private oasis just 30 miles from Midtown Manhattan.

20 Meeting House Road, Bedford Corners

$4,400,000

5 Beds ⋅ 7 Baths ⋅ 1016358 MLS

Tucked away at the end of a long private drive and completely hidden from the road, this extraordinary contemporary estate offers one of the most private and captivating settings in Scarsdale. Set on two breathtaking acres bordering Fenway Golf Club, the property is surrounded by mature specimen trees, lush landscaping, a resort-style pool, and a spectacular koi pond home to hundreds of koi, creating a setting that feels worlds away from everyday life. Designed with exceptional craftsmanship and remarkable architectural vision, the residence is defined by soaring ceilings, dramatic walls of glass, abundant natural light, and a seamless connection to the outdoors. A striking copper roof and oversized copper entry door introduce a home that is both architecturally significant and effortlessly livable. The thoughtfully designed floor plan balances grand entertaining with comfortable daily living. A private primary suite serves as a true retreat, complete with dual walk-in closets, a dressing area, and a spa-inspired bath. A separate bedroom wing provides three additional bedrooms and generous accommodations for guests. Formal living and dining rooms frame picturesque views of the pond and grounds through floor-to-ceiling glass, while the expansive eat-in kitchen features custom cabinetry, granite countertops, premium appliances, and a butler’s pantry. At the heart of the home, a spectacular double-height family room invites gathering and relaxation. Vaulted ceilings, tiers of skylights, custom built-ins, walls of glass, and a dramatic stone fireplace create a space that is both impressive in scale and warm in character. The walk-out lower level offers exceptional flexibility, with recreation space, guest accommodations, gym or studio options, abundant storage, and direct access to the outdoors. Outside, the estate unfolds as a private sanctuary. Japanese-inspired gardens, stone terraces, multiple entertaining areas, level lawns, and tranquil water features create an atmosphere rarely found in Westchester. Attached and detached garages provide space for four vehicles, complemented by extensive guest parking and a private driveway that enhances the estate’s exclusivity. Just 32 minutes from Manhattan and located within the highly acclaimed Scarsdale School District, this is a rare opportunity to own one of Scarsdale’s most distinctive residences, an architectural retreat offering exceptional privacy, natural beauty, and a lifestyle unlike any other.

41 Murray Hill Road, Scarsdale

$787,000

3 Beds ⋅ 3 Baths ⋅ 1016600 MLS

Welcome to this beautifully maintained 3-bedroom, 2-bath home, perfectly situated on a quiet, sidewalk-lined street in Yonkers. Offering a wonderful blend of comfort, space, and convenience, this home is ready for its next owner to move right in and enjoy. Inside, you'll find a bright and inviting living area filled with natural light, complemented by hardwood floors throughout. The updated kitchen offers ample cabinet space and room for dining, making it ideal for both everyday living and entertaining. Three generously sized bedrooms and two full and a half baths provide a practical and comfortable layout. Additional features include an indoor garage and a partially finished basement, offering flexible space for a recreation room, home office, gym, storage, or future customization. Step outside to your own private backyard retreat featuring a fully fenced yard, perfect for gatherings, outdoor activities, gardening, or simply relaxing. The private pool and jacuzzi create the perfect setting to enjoy warm summer days and evenings at home. Conveniently located near shopping, dining, parks, schools, and major transportation routes, this well-maintained property offers a fantastic opportunity to enjoy all that Yonkers has to offer.

18 Arden Place, Yonkers

$5,880,000

8 Beds ⋅ 10 Baths ⋅ 1012962 MLS

Welcome to “Apple Blossom Farm”, an extraordinary opportunity to own a remarkable private estate designed for grand-scale living, entertaining, and multi-generational enjoyment. Set on beautifully landscaped grounds in desirable Bedford Corners, this impressive 12,000-square-foot residence offers 8 bedrooms and an exceptional collection of indoor and outdoor amenities. Designed as the ultimate compound, the property comfortably accommodates both intimate gatherings and large groups, making it ideal as a private retreat, wellness destination, luxury vacation residence, or year-round estate. Expansive living and entertaining spaces create the perfect balance of grandeur, comfort, and privacy. A stunning glass-enclosed sunroom adjacent to the music room fills the home with natural light and showcases beautiful views of the surrounding property, creating a serene space for relaxation and entertaining. The lower-level fitness center offers ample space for a professional-caliber gym, easily accommodating strength-training equipment, cardio machines, and dedicated yoga or Pilates areas. Resort-style amenities abound, including a tennis court, sparkling swimming pool, and extensive outdoor spaces designed for recreation, relaxation, and unforgettable gatherings. Whether enjoying summer weekends by the pool, holiday celebrations with friends, or extended stays in a peaceful country setting, the estate delivers an unparalleled lifestyle experience. Beyond its exceptional residential appeal, Apple Blossom Farm has a proven history as a successful investment property, generating impressive returns while offering substantial income-producing potential for investors and owners alike. A truly rare offering that seamlessly combines luxury, versatility, and investment opportunity in one exceptional Bedford Corners estate. “Apple Blossom Farm” presents a unique chance to own a destination property where recreation, wellness, and hospitality come together in spectacular fashion.

196 McLain Street, Bedford Corners

$749,000

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

$15,000,000

5 Beds ⋅ 6 Baths ⋅ 1007263 MLS

EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

164 Eastwoods Road, Pound Ridge

$1,532,000

5 Beds ⋅ 5 Baths ⋅ 1007480 MLS

Spacious contemporary single-family residence situated on approximately 1.5 acres in Dobbs Ferry. This property offers approximately 4,120 sq ft of living space with 10 total rooms, including 5 bedrooms and 5 bathrooms. Features include an attached 1-car garage and expansive grounds providing potential for outdoor enhancements. The home is currently vacant and presents an opportunity for renovation and customization. Convenient location with access to local amenities, transportation, and major roadways. Property is being sold as-is. Buyer to perform all due diligence

200 Judson Avenue, Dobbs Ferry

$4,595,000

7 Beds ⋅ 9 Baths ⋅ 956753 MLS

A charming bucolic retreat just moments from the city, 15 Sarosca Farm Lane is privately set at the end of a tree-lined lane on 5.89 spectacular acres. Rich in character and historic architectural detail, this 7-bedroom, 9-bath home offers a rare combination of privacy, scale, and resort-like amenities, including a sweeping driveway, tree house, tennis court, in-ground pool, half basketball court, vegetable garden, apple orchard, and a stone tower once used to supply water to the home. Inside, the 9,549-square-foot residence is designed for both gracious entertaining and everyday living, with an expansive eat-in chef’s kitchen, formal dining room, seven fireplaces, and a four-season room opening to an adjacent patio. The home also features a built-in barbecue, generous mudroom with laundry, upstairs recreation room, six en-suite bedrooms, gardener’s potting room, artist’s nook, and lower-level sporting storage. A detached heated 3-car garage and 1,040-square-foot gym further elevate the offering. A private oasis unto itself, the upstairs primary suite includes two walk-in closets, two bathrooms, and a large office. A rare and remarkable offering in Purchase, not to be missed.

15 Sarosca Farm Lane, Purchase

$999,000

6 Beds ⋅ 5 Baths ⋅ 1006585 MLS

Lovingly owned by the same family for more than 30 years, 26 Glen Avenue is a rare Port Chester offering that blends original warmth with exceptional space, versatility, and outdoor living. This expansive 6-bedroom home features 3 full bathrooms and 2 half bathrooms, along with over 3,000 square feet of living space that includes multiple bonus rooms ideal for today’s needs—home offices, workout areas, creative studios, or flexible recreation spaces. The bright, flowing layout provides practical everyday living with room to grow, refresh, or personalize over time. Natural light highlights the home’s timeless character, while the generous floor plan easily accommodates multi-generational living or anyone seeking abundant space in a central location. The outdoor setting is a true private oasis. A patio and deck highlight the in-ground swimming pool, creating a resort-like environment perfect for summer gatherings, entertaining, or quiet relaxation. The property also includes a detached 2-car garage and a driveway that accommodates up to 5 additional vehicles, offering exceptional parking and storage—an uncommon convenience in this area. Ideally situated just half a mile from the Port Chester Metro-North Station, the home provides quick access to NYC and the region. You’re moments from the village’s vibrant dining scene, shopping, entertainment, and all the amenities that make Port Chester such a dynamic and convenient place to live. With its combination of size, location, and decades of thoughtful ownership, 26 Glen Avenue is a well-loved residence and a wonderful opportunity for buyers seeking a spacious home to enjoy now and update over time. This is one you’ll want to experience in person.

26 Glen Avenue, Port Chester

$3,975,000

7 Beds ⋅ 13 Baths ⋅ 1004695 MLS

Magnificent multi-generational 7 plus bedroom, 13-bathroom home on 4.5 acres with a heated indoor swimming pool and spa. This expansive home has two distinct wings (original home built in 1936 and a new wing built in 1991) and lives like two independent houses, each with their own utilities, kitchens and laundry room and are joined by a common front foyer. The original house has an oversized living room with French doors leading to terrace, a formal dining room, an updated kitchen with separate breakfast area, and mud room. On the second level is the primary suite with dressing room and two renovated bathrooms, two additional ensuite bedrooms and laundry room. And the third floor has two sunny offices with balconies and a full bathroom, The new addition has an open updated kitchen/great room with balcony overlooking yard, a large living room/dining room and a primary suite with walk in closet and full bathroom. On the second level are two additional bedrooms, a bonus room and a full bathroom. Amazing 60’ Shoreline pool and spa in a expansive room with wall of window, a changing room and full bath, and is adjacent to a great recreation room/gym. Special features include abundant windows, high ceilings, extensive woodwork and moldings, wood floors, 3 fireplaces, multiple balconies, generator, 4 car garage and a private guest wing with separate entrance. The outdoor space is exceptional with meadows, sprawling lawns, specimen trees, cutting gardens, and stone terraces. Meticulous condition- roof (2020), AC condensers (2020), Boilers (2021/2023), new driveway (2026), new 7-person septic (2026). Full basement with high ceilings offers excellent storage. Full house generator. This ultra-private home is in a prime location and located very near to Armonk town center. Israel Townsend HIll is a new street, located off of Orchard Drive. Byram Hills Schools

3 Israel Townsend Hill, Armonk

$1,750,000

9 Beds ⋅ 8 Baths ⋅ 1005133 MLS

Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities. The beautifully renovated 5,337-square-foot Main House features 5 spacious bedrooms and 3.5 bathrooms, showcasing refined craftsmanship and sophisticated updates throughout. At the center of the home is a stunning chef’s kitchen equipped with premium Sub-Zero appliances, designed for both everyday living and elegant entertaining. Recent upgrades include new windows, a new roof, and solar panels on the Main House, offering enhanced efficiency and sustainability. Beyond the main residence, the estate includes a charming 1,020-square-foot Guest House with 3 bedrooms and 2 bathrooms, ideal for long term guests, or private office space. A separate Gate House with 2 bedrooms and 2 bathrooms adds even more versatility and privacy. Surrounded by lush grounds and mature landscaping, the property offers resort-style amenities including an in-ground swimming pool and private tennis courts, creating a true retreat just outside the city. A rare opportunity to own a distinguished estate that delivers privacy, luxury, and convenience in one of Westchester County’s most coveted locations.

51 Pinesbridge Road, Ossining

Start Your Search

Prev
1
...
10
11
12
...
14
of 14
Next

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.

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

How much is your home worth?

How much is your home worth?

Tierra Stanback