Homes for Sale with a Pool in Westchester, NY

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Welcome to your dedicated resource for homes for sale with a pool in Westchester, NY. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Westchester, NY agent, Tierra Stanback specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Pool in Westchester, NY

$10,999,000

7 Beds ⋅ 7 Baths ⋅ 1004759 MLS

An extraordinary expression of modern architecture and timeless craftsmanship, this 9,601-square-foot estate sits on nearly an acre in one of Scarsdale's most prestigious neighborhoods. With an emphasis on scale, light, and clean contemporary design, the home delivers an elevated lifestyle of privacy, comfort, and sophistication. A dramatic double-height foyer welcomes you into expansive interiors designed for seamless living and entertaining. The formal living room is anchored by a sleek fireplace and oversized windows that frame the landscaped grounds. The open-concept layout continues through the dining area and into a stunning chef's kitchen featuring top-tier appliances, custom cabinetry, and an oversized island, crafted for both daily living and grand-scale hosting. Upstairs, the primary suite offers a private retreat with dual walk-in closets and a spa-inspired bath finished in refined stone and designer fixtures. All secondary bedrooms include en-suite bathrooms and generous proportions, offering privacy and comfort for family and guests. The finished lower level extends the living space with a full gym, a custom cigar lounge with ventilation, and an expansive lounge area Remarks: Hydronic Heating . Outside, the grounds are equally impressive, with a heated pool, multiple dining and lounge areas, and a flat lawn, all surrounded by mature landscaping for privacy and tranquility. Located minutes from the village, and top-ranked schools, this is one of Scarsdale's finest modern homes custom built for those who value design, scale, and discretion.

64 Cushman Road, Scarsdale

$3,075,000

4 Beds ⋅ 5 Baths ⋅ 1002022 MLS

Welcome to Orchard Estates, a wonderful new development of single-family homes in Armonk. This home “to be built” is 5641 SF (not including unfinished 2170 SF lower level) and offers 4 bedrooms plus two offices, 5 bathrooms, 3 car garage, high-end finishes, and is on a 2.52 acre lot that offers privacy and an expansive level yard. This home is located on beautiful estate property that has been subdivided into 5 lots, ranging in size from 5 acres to 1.6 acres, offering privacy, specimen plantings, mature trees, level yards, pool sites, and more. The development is private, yet just minutes to Armonk town center, shopping, and restaurants. Located 45 min to NYC, 15 min to Westchester airport, 20 min to Greenwich CT, and 10 min to Metro North train station. Great opportunity, to make build your dream house. Byram Hills Schools.

2 Israel Townsend Hill, Armonk

$1,579,000

4 Beds ⋅ 3 Baths ⋅ 1002709 MLS

Welcome to 55 Hawley Avenue — a rare opportunity that appeals equally to Homeowners seeking a turnkey luxury residence and Investors looking to acquire a proven, cash-flowing asset that generated nearly $200,000 in verified rental revenue in 2025 alone! Built in 2018, this 4-bedroom, 2.5-bath luxury home offers over 3,100 square feet on a private, tree-lined lot with a spacious backyard centered around a resort-style heated saltwater pool and a large hot tub that fits 6 comfortably. Inside, real hardwood floors run throughout the main and upper levels. An open-plan chef's kitchen with LG appliances, gas range, and wine fridge flows seamlessly into the dining room and entertainment-friendly living room, plus a dedicated billiards room and additional office or reading room. Upstairs, 4 spacious bedrooms with 5 beds can easily sleep 10 and include a king primary suite with ensuite bath and walk-in closet. A 600 sq ft semi-finished basement offers tremendous potential — gym, recreation room, additional living space, or more. A covered front porch, dedicated laundry, one-car garage, and private driveway complete the home — which comes fully furnished and turnkey. The location is exceptional: a walkable, friendly Port Chester neighborhood with great dining, two parks within walking distance, easy access to I-95 and I-287, Metro-North to Grand Central in under 45 minutes, and Rye Beach, Greenwich, and Rye just minutes away. This is the only home in Westchester County built within the last 10 years with a private pool currently on the market! For the homeowner, it is move-in ready with resort-style amenities in a phenomenal friendly neighborhood appreciating year over year. For the investor, it is a fully operational short-term rental generating nearly $200,000 in verified 2025 gross revenue — listed as "The All Seasons Oasis!" on Airbnb and VRBO with a perfect 5.0 rating across over 70 reviews and Airbnb's Guest Favorite designation, placing it in the top 5% of all regional listings, & likely the top producing Airbnb in Westchester County! Properties like this simply do not come available often -- schedule your showing today!

55 Hawley Avenue, Port Chester

$7,950,000

8 Beds ⋅ 10 Baths ⋅ 997025 MLS

INLAND VALE. Steeped in history. One of Northern Westchester’s most significant Country Estates. Magnificent and majestic stone and shingle residence originally built in the 1850’s. Renovated by Stanford White for Ulysses S. Grant, Jr. Remarkable preserved details including spectacular aged paneling, ten fireplaces with vintage mantles and tile, and extensive millwork. Long tree-lined drive to dramatic stone entrance. Magnificent oak paneled Great Hall with grand staircase and ceiling of Tiffany stained glass. Beautifully proportioned main rooms designed for entertaining on the grand scale. Impressive Living Room with mirroring fireplaces and French doors to columned porch. Formal Dining Room. Chef’s Kitchen with high-end appliances. Sun-filled Family Room with Breakfast Area and doors to outdoor terrace in walled garden. Remarkable Primary Suite with spacious Dressing Room and two Baths. Six additional Bedrooms. Playroom with built-in desks, game closet and doors to rooftop porch. Full Third Floor with glass-ceilinged Sitting Room, second Kitchen, Art Room/Studio and Exercise Room. Lower Level with Game Room, Wine Cellar and Pool Cabana. All mechanicals are updated including center air conditioning and a generator. Baths are Waterworks with luxurious radiant heat. Over eleven park-like acres with specimen trees, flowering shrubs and verdant lawns. Incredible old world stonewalls and terraces. The perfect retreat complete with swimming pool, tennis and half-basketball court. A once in a lifetime opportunity!

640 Grant Road, North Salem

$3,150,000

5 Beds ⋅ 6 Baths ⋅ 934693 MLS

Beyond private gates in coveted Back Country Bedford, this exceptional estate offers the perfect balance of privacy and convenience—just minutes to Bedford Village, Greenwich, the Merritt Parkway, and I-684. Bordering the protected Mianus River Gorge Preserve, the property enjoys an unparalleled natural setting with beautifully landscaped grounds, cascading waterfall and resort-style Shoreline pool and spa. Elegant yet welcoming interiors feature a stunning finished mahogany dining room, richly appointed cherry-paneled family room, bespoke millwork, and a thoughtfully designed layout for everyday living and entertaining. The chef’s kitchen opens to expansive outdoor terraces, while the luxurious primary suite, first-floor guest suite, wine cellar, media room, heated three-car garage, and whole-house generator complete this extraordinary offering. A rare opportunity for peaceful country living with effortless access to both Bedford and Greenwich. Available for sale or lease.

10 Hopes Farm Lane, Bedford

$859,900

3 Beds ⋅ 3 Baths ⋅ 1003275 MLS

Welcome to exceptional indoor and outdoor living. Set on a private 1.5 acres and surrounded by mature trees, this home features incredible outdoor spaces ideal for entertaining or relaxing in total privacy. This custom home offers an impressive stone facade set in granite and stone column entry is set privately and situated on 1.5 acres in an ideal Southern Yorktown location with Yorktown schools. Step inside this home and feel how open and light-filled the entire main living level with sun drenched rooms, windows galore and distant views. Let the sunshine in on the recently refinished hardwood floors, the open floor plan is flexible and smartly designed with spaces for dining, open living room and a stunning kitchen designed for the serious cook with side and rear decks to enjoy the outdoors those distant views. The kitchen has storage galore with a pantry closet and custom cabinetry, professional-grade oven/range and finished with granite tops with large center island. Whether for daily needs or special occasions, this kitchen will perform quite capably, and the cook will appreciate the beautiful views. This home offers a remarkable amount of indoor-outdoor flow, including access to a rear deck and a side deck off the kitchen, just a perfect spot to enjoy your morning coffee. The owner's suite has ample space and includes an on-suite bath. The finished lower level provides a family room, home office or guest room with a summer kitchen and full bath. It’s the perfect setup for guests or the extended family. 986 Cliff Avenue is an ideal residence for the buyer seeking a thoughtfully designed house offering privacy, home office and recreation spaces, including an impressive stone saltwater pool with waterfall. Set in an ideal location and just a few minutes to town shopping, restaurants, access to the county bike trail and close proximity to schools, hiking trails, town parks and parkway.

986 Cliff Avenue, Yorktown Heights

$2,995,000

4 Beds ⋅ 5 Baths ⋅ 995187 MLS

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature. Outdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation. The residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in. At the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chef’s kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living. The home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for today’s lifestyle. A screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property. Complete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease. Just minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

127 Boutonville Road, Pound Ridge

$2,549,000

5 Beds ⋅ 4 Baths ⋅ 999117 MLS

True resort-style living with the ultimate in privacy, this exceptional residence is set on nearly one acre of tranquil grounds surrounded by lush landscaping and spectacular stonework throughout. A grand double-height entry foyer welcomes you to this spacious, sun-filled five bedroom, four full bath home, featuring generously sized rooms, including two en-suite bedrooms, and two family rooms. The luxurious primary suite features a large en-suite, walk-in closet, gas fireplace, and a balcony overlooking the property. Meticulously maintained high-end details highlight an effortless flow designed for both everyday living and entertaining. The open kitchen flows seamlessly into the family room with fireplace and stunning atrium, which opens directly to the picturesque grounds, outdoor kitchen, and serene koi pond. The living room with fireplace opens to the dining room, a beautiful four-season sunroom leads to an additional patio and garden setting, creating indoor-outdoor living throughout the home. The expansive heated pool and spa are enveloped by exquisite mature plantings and a charming rock garden path, offering a truly private retreat-like setting. Additional special features include radiant heated floors in the entry foyer, atrium, sunroom, and primary bath, a full-house generator, three fireplaces, three car garage, a very spacious driveway. Fully fenced grounds complete this extraordinary home. All in a very convenient location. A wonderful place to call home!

1 Rock Hill Lane, Scarsdale

$2,275,000

4 Beds ⋅ 5 Baths ⋅ 998251 MLS

*MASSIVE PRICE DROP, DONT MISS OUT!!!! PRICED TO SELL!!! A rare opportunity to customize your dream home at 122 Old Mt. Kisco Road in the heart of Armonk. This newly constructed residence already has its frame in place, offering the next owner a unique chance to bring their vision to life by selecting finishes, materials, and design details tailored to their personal style. Set on a beautiful property, the home features a stunning two-car garage and an expansive layout designed for modern living. Generous proportions, soaring ceilings, and thoughtfully designed living spaces create the perfect foundation for a truly exceptional residence filled with natural light and timeless appeal. Whether you envision a sleek contemporary retreat or a warm traditional estate, this home serves as the ultimate blank canvas. Enjoy all the advantages of new construction without the lengthy building timeline, while still creating a home that feels entirely your own. The developer also has the ability to add a custom pool to the property at an additional cost, creating the opportunity for a true private backyard oasis. Perfectly situated in sought-after Armonk, the property offers close proximity to top-rated schools, charming downtown shops, fine dining, parks, and convenient commuting options. This is a truly one-of-a-kind opportunity to design and personalize a luxury home from the inside out in one of Westchester’s most desirable communities.

122 Old Mount Kisco Road, Armonk

$5,950,000

5 Beds ⋅ 5 Baths ⋅ 997057 MLS

Blue Heron at Peach Lake is a rare lakefront retreat tucked away on 3.46 private acres at the end of a quiet cul-de-sac in North Salem. This exceptional 5-bedroom, 4.5-bath estate offers direct waterfront living with a private dock, sandy beach, and sweeping views of Peach Lake. Designed for both entertaining and everyday luxury, the outdoor setting features an in-ground pool with integrated spa, poolside cabana with bathroom, expansive stone patios, perennial gardens, and mature specimen trees. Gas-plumbed real-flame lanterns and a built-in firepit create a resort-like atmosphere across multiple outdoor gathering spaces. Inside, timeless craftsmanship is showcased through extensive custom millwork, generous living spaces, and a stunning oversized eat-in kitchen that anchors the home’s main level. Radiant heated floors run throughout the home and garage, adding year-round comfort and luxury. The expansive lower level offers a large gym, bonus/recreation room, and abundant storage, providing exceptional flexibility for lifestyle and entertaining needs. Set in the heart of Westchester’s celebrated horse country, the property combines privacy and convenience — approximately one hour from NYC, one hour to the Catskills, and just minutes to Metro-North. A truly rare offering combining acreage, privacy, refined craftsmanship, and authentic lakefront living.

6 Brookside Lane, North Salem

$2,249,000

3 Beds ⋅ 4 Baths ⋅ 973551 MLS

Set on beautifully landscaped grounds in one of Chappaqua’s most coveted neighborhoods, this exceptional luxury Colonial blends timeless architecture, designer finishes, and an unmatched indoor-outdoor lifestyle within the award-winning Chappaqua school district. Privately positioned against acres of preserved land, this premier Westchester County property offers both tranquility and convenience, just minutes to Metro North, downtown Chappaqua, and Chappaqua Crossing featuring Whole Foods Market and Life Time. Living like a 5-bedroom home, this luxury home for sale in Chappaqua showcases exceptional craftsmanship throughout with Juliet balconies, copper-topped cupolas, Belgian block-lined driveways, soaring ceilings, custom millwork, and walls of glass that flood the interiors with natural light. A dramatic curved staircase welcomes you into elegant yet comfortable living spaces designed for both everyday living and sophisticated entertaining. The chef’s kitchen is beautifully appointed with premium Wolf and Sub-Zero appliances, custom cabinetry, and European mosaic tilework, seamlessly connecting to the formal and casual gathering spaces. Highlights include a sophisticated library with gas fireplace, a stunning vaulted family room, and an impressive entertainment lounge with a wood-burning fireplace, wet bar, Viking wine refrigerator, and custom built-ins. The luxurious primary suite offers a gas fireplace, oversized dressing room, and spa-inspired bath, delivering the ultimate private retreat. Outside, the property lives like a private resort with a heated saltwater pool, outdoor fireplace, expansive patios, built-in grill, fire pit, poolside grotto with shower and changing area, gazebos, and a half basketball court with spotlighting. This exceptional Chappaqua estate offers luxury living, privacy, and resort-style amenities in one of Westchester’s most sought-after communities, known for top-rated schools, vibrant downtown, and easy NYC commute. A rare opportunity to experience estate-style living and the quintessential Chappaqua lifestyle at its finest.

33 Greenbriar Drive, Chappaqua

$3,095,000

4 Beds ⋅ 7 Baths ⋅ 996255 MLS

A rare offering where extraordinary craftsmanship, uncompromising luxury, and complete privacy converge to create a residence without equal. Hidden behind a gated entrance and framed by magnificent stone walls in prestigious Bedford, this exceptional estate makes an unforgettable first impression long before you arrive at the front door. Step inside and discover a world designed to elevate everyday living—where soaring ceilings, dramatic open spaces, and walls of glass create a breathtaking interplay of natural light and architectural beauty. Every inch of this remarkable home has been masterfully crafted with an unwavering commitment to quality, seamlessly blending timeless sophistication with modern comfort. The main level is designed for both grand-scale entertaining and effortless daily living, featuring expansive gathering spaces, a beautifully renovated chef’s kitchen, and a private guest or in-law suite offering comfort and flexibility for extended stays. Outside, a resort-caliber setting awaits. A spectacular covered terrace is anchored by a grand outdoor fireplace on one end and a built-in grilling station on the other, with generous spaces in between for elegant entertaining or quiet evenings under the stars. Beyond, an extraordinary custom stone infinity-edge pool, separate stone spa, and sweeping terraces create a private sanctuary that feels more like a five-star resort than a private residence. Return indoors to enjoy the private steam sauna and Finnish spa on the main level—bringing a true wellness experience into your daily life. The second floor is dedicated to luxurious private living, highlighted by an exquisite primary suite designed as a personal sanctuary, along with three additional en-suite bedrooms that offer exceptional comfort and privacy for guests. The lower level redefines home entertainment with an experience rivaling premier private clubs—featuring a custom-designed full bar, a state-of-the-art home theater, fitness studio, and expansive recreation spaces ideal for billiards, celebrations, or unforgettable gatherings. For the automobile enthusiast, the heated garage comfortably accommodates six vehicles. Perfectly positioned in Bedford, New York—renowned for its historic charm, estate properties, and timeless appeal—this extraordinary residence offers the ultimate escape from the demands of everyday life while remaining close to exceptional dining, boutique shopping, and equestrian pursuits. This is more than a home—it is a destination, a retreat, and a once-in-a-lifetime opportunity for buyers seeking nothing less than perfection.

68 Quarry Lane, Bedford

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Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.