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

$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

$6,400,000

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

$2,500,000

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

$4,995,000

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 David Graham-designed 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

$1,695,000

5 Beds ⋅ 6 Baths ⋅ 994571 MLS

"VILLA KEEN" - THE GLAMOUR OF A CASTLE MEETS BROADWAY & THE ARTS - Irvington, NY, Circa 1929. Just imagine... Joseph Keen & his wife break ground to build a "Cinderella" castle on a breathtaking 2.43 acre parcel of land, a stone's throw to Halsey Pond, minutes to the Hudson River and a short 30 minute trip from Manhattan. Coming home, meandering through the stately stone pillar entry, the Beech Tree with historic Indian carvings in front of the sweeping stairs tells a story from the 1700's, but that we will save for a rainy day... Fast forward, Lloyd Stratton, president of the Associated Press takes residency, tirelessly typing from the oak library. In the 1960's enters resident Robert Wright, producer of the Carol Burnett Show & other Broadway staples. If you are seeking inspiration beyond your wildest dreams, everything is still in tact today, including the Chesney fireplace mantle, Mackenzie-Childs fixtures and the Schonbek Austrian crystal chandelier... If you are looking to entertain, be our guest, whether you enter through the 15' stained glass gates to your private courtyard, spend your time in the grand dining room suitable for Beauty & the Beast, the Green Room, relaxing poolside, or in the pool house, the choice is yours. Of course your guests or residents will cherish their stay in the turret bedrooms with ornate stained glass windows, or in the private guest quarters with separate entry... Speaking of entertainment, the list of distinguished guests and residents goes on, like Academy award-winning actress Shirley Jones, Tony Award-winning actor Jack Cassidy and their son, multi-platinum recording artist Shaun Cassidy. If only these walls could talk... Well, you may still hear the grand piano resonating in the formal living room by one of the many roaring fires... A perfectly sound structure on a dead end private street, with newer systems & mechanics, a train line to NYC just 5 minutes away and award-winning Irvington Schools, here is your chance to enhance a property that can never be duplicated today. In fact, "Villa Keen" is so special, a replica only exists in California by one of its former owners. Are you ready to live this fairytale fantasy?

16 Lewis Road, Irvington

$1,325,000

5 Beds ⋅ 4 Baths ⋅ 995205 MLS

This stately luxury Mediterranean villa near Bronxville is set high on a private, lushly landscaped large corner property. The flagstone walkway leads to a refined entry door with brass lion-head knocker and into the grand foyer featuring a sweeping curved staircase with distinctive balustrades. Classic center hall layout with all oversized rooms is perfect for entertaining and relaxing. Two sets of leaded-glass double French doors open to the ballroom-sized living room and elegant dining room, both with intricate moldings, gleaming hardwood maple floors and custom fireplace. All walls and ceilings are hand-crafted Venetian plaster. Sun-drenched wood paneled home office or first floor bedroom has new bay window and built-ins. A bath with gold fixtures is also on the first floor. The updated kitchen and butler’s pantry have stunning granite counters, designer backsplash, a custom 40" gas range with six burners, double oven and oversized range hood, breakfast nook and mud room with many closets. Amenities include a lower level in-law apartment with full bath, separate access and expansion possibilities. Upstairs, the huge ensuite primary bedroom has its own private 220 SF terrace, cedar closets, and enormous remodeled bath with marble floor and separate shower room. The walk-out lower level, with rec room, laundry, full bath with shower, and bedroom, accommodates au pair or in-law. The heated, two-plus car garage is below the house, with direct indoor access. Third floor has additional 1,500 SF with cathedral ceiling (not included in house square footage) with space for 6th and 7th bedroom and full bath. New 200-amp service and new electric throughout. Freshly painted, inside and out. Very private yard has fully operable in-ground gunite mini pool that provides a special outdoor oasis. Massive stone walls, terraces, patios, and full property underground sprinkler system. Ludovici red Spanish tile roof is spectacular. Some furnishings included. Short walk to Metro North. NYC commute is 25-minutes from Fleetwood or Bronxville. Shopping in Fleetwood and Bronxville. MOVE-IN READY. Low taxes are before STAR exemption. Great value per square foot.

130 E Cedar Street, Mount Vernon

$6,400,000

6 Beds ⋅ 5 Baths ⋅ 992131 MLS

WOLSEY FARM. One of Bedford’s most iconic estate properties—first time offered in nearly 100 years. Remarkable Colonial Estate dating to 1810. Grand main rooms with incredibly preserved period detailing. Stunning interior with graciously proportioned rooms, high ceilings, period millwork, intricate moldings and spectacular quarter-sawn oak floors with black walnut inlays. Impressive Portico supported by massive Corinthian columns. Center Entrance Hall. Living Room with fireplace and doors to covered porch for alfresco entertaining. Formal Dining Room for entertaining. Country Kitchen with breakfast area. Family Room with doors to terrace. Library and Office for working remotely. Six Bedrooms including Primary Suites. Spectacular terrace and covered porch for alfresco entertaining. Heated Pool with Spa. Over eighteen spectacular acres with incredible trees and flowering plantings in the heart of Bedford. Gate House with fireplace-the ideal artists’s or writer’s studio. Two Bedroom Guest Cottage. Second “Superintendent’s” Cottage with two Bedrooms. Numerous barns and farm buildings including large Chicken Coop. Six fenced paddocks, an orchard, a spring-fed pond and open meadows. A once in a lifetime opportunity!

345 McLain Street, Bedford Hills

$1,545,000

4 Beds ⋅ 4 Baths ⋅ 986984 MLS

Welcome to Somers Estates, one of Somers newest subdivisions. Custom designed Farm House where value meets Luxury. Situated on 1.13 acre level lot . Front covered porch with standing seam roof. Dramatic Front Foyer, entry, and Family room with fireplace. Formal dining room, Chefs Kitchen, living room, office, bath, and mudroom on first floor that leads to the three car garage. Second floor features, primary bedroom, with full bath and separate shower. There are three additional bedrooms, baths, and laundry. Both levels feature 4" select red oak flooring and tile in all baths. Full basement can be finished. For more specific details, ask for our Standard Specifications.

24 Florence Drive, Somers

$2,595,000

5 Beds ⋅ 5 Baths ⋅ 991143 MLS

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

217 Trinity Pass, Pound Ridge

$3,825,000

5 Beds ⋅ 5 Baths ⋅ 987844 MLS

Priced to SELL! Five-plus private acres. A century-old Georgian. Towering trees, beautiful gardens, charming guest cottage and a pool within an hour of NYC! Historic without feeling precious. Private without feeling remote. Grand enough for a proper dinner party, relaxed enough for barefoot afternoons by the pool. • Exceptional early-20th-century Georgian architecture by Delano & Aldrich • High ceilings, great flow, French doors, fireplaces, and beautiful original details • Generous living and dining rooms for entertaining • Light-filled sunroom opening to a stone terrace and gardens • Inviting kitchen (6 burner Viking stove, Sub Zero fridge) + adjoining sitting room for everyday living • Primary suite with fireplace and sun-filled ensuite bath • Multiple bedrooms with fireplaces and garden views • Skylit third-floor artist’s studio + adjoining atelier • 5+ acres of privacy and peaceful natural surroundings, extra land available • Gated, tree-lined gravel drive • Specimen trees + curated perennial gardens • Lovely pool • Enchanting guest cottage • Greenhouse • Detached two-car garage. Chic Classic architecture. Modern country life. Room to make it yours.

328 McLain Street, Bedford Hills

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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.