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

$4,995,000

5 Beds ⋅ 6 Baths ⋅ 966535 MLS

Luxurious new construction in prestigious Ardsley Park! Located in the charming village of Dobbs Ferry, this prime home offers nearly 8,000 square feet of beautifully designed living space including a finished lower level. This exceptional, custom house features five spacious bedrooms, 5.5 baths, and a three-car garage, with time still available to personalize select finishes. Designed for modern living and effortless entertaining, the home also includes a stunning 20’ x 40’ swimming pool, creating a private backyard oasis. The chef’s kitchen is outfitted with premium appliances including a Sub-Zero refrigerator, Wolf range, and Bosch dishwasher, complemented by elegant quartz countertops and impeccable craftsmanship throughout. The spectacular primary suite offers a serene retreat with two, large walk-in closets and a luxurious spa-inspired bath with soaking tub, shower, double vanity, and quartz counters. Ideally located close to the Metro-North train station with a 36-minute commute to Grand Central Terminal, and within the highly regarded, award-winning Dobbs Ferry School District. A rare opportunity to enjoy sophisticated, new-construction living in one of Westchester’s most desirable Rivertown neighborhoods.

161 Sherman Avenue, Dobbs Ferry

$5,950,000

6 Beds ⋅ 8 Baths ⋅ 960785 MLS

Privately set along a winding drive in the coveted Gifford Lake enclave of Armonk, this extraordinary estate offers the feeling of a year-round retreat. Homes of this caliber are defined by extraordinary millwork, full stone cladding, bespoke interior detailing, and museum-quality finishes, reflecting an uncompromising standard of craftsmanship rarely realized in today’s luxury landscape. While rich in architectural pedigree and old-world craftsmanship, the home’s thoughtfully curated color palette, refined designer lighting, and seamless integration of modern materials and fixtures create a sophisticated and current aesthetic. The result is a timeless yet fresh ambiance that feels elegant, vibrant, and thoughtfully modern in its presentation. The exceptional depth of materials and masterful execution throughout this Gifford Lake estate truly distinguish it from anything else on the market. Hand-finished Venetian plaster, intricate custom paneling and wainscoting, richly detailed coffered ceilings, curated designer lighting, premium marble and granite selections, and an extensive stone package that would be extraordinarily costly to replicate today establish a remarkable level of quality. A stone-pillared entry and antique granite courtyard introduce the home’s architectural pedigree. Inside, a dramatic double-height foyer with chevron hardwood flooring, elaborate millwork, coffered ceilings, and a sweeping staircase immediately showcase the craftsmanship carried throughout the residence. Five fireplaces with custom mantels and marble surrounds, crown molding across all levels, bespoke cabinetry, designer wallcoverings, premium marble and leathered granite surfaces, and integrated Sonos audio elevate every space. The chef’s kitchen features Wolf and Sub-Zero appliances, Arabescato marble, a substantial leathered granite island, custom wood cabinetry with glass display uppers, and a glass-wrapped breakfast area filled with natural light. The owner’s retreat serves as a private sanctuary with architectural ceiling detail, a bespoke dressing room with center island, radiant heated spa bath, and refined marble finishes. The fully finished walk-out garden level continues the home’s elevated design with a custom theater and built-in snack bar, brick fireplace lounge, bespoke bar, fitness studio, and resort-style entertaining spaces. Outdoors, full stone cladding, copper detailing, a heated saltwater pool and spa, custom outdoor kitchen, pergola, and professionally landscaped grounds complete this irreplaceable estate offering. Conveniently located near schools, shops, and acclaimed dining in the nearby towns of Armonk, Bedford, and Greenwich, and served by the award-winning Byram Hills School District. Some Photos enhanced for seasonal representation.

12 Gifford Lake Drive, Armonk

$4,500,000

5 Beds ⋅ 7 Baths ⋅ 950756 MLS

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original interior stone walls and soaring ceilings that strike a perfect balance between grand scale and intimate warmth. Anchored by three distinctive hearths, the home is designed for both elegant living and everyday ease. A sun-drenched chef’s kitchen showcases a central island, dramatic overhead skylight, and professional-grade appliances. Unique architectural moments—including a circular-skylit Stargazer’s Nook—add character and charm, while the versatile five-bedroom layout offers both a magnificent two-story primary wing and a coveted first-floor private suite. Set on more than four exceptionally private acres, the grounds unfold as a true outdoor sanctuary, featuring a beautiful pool and spa (32x20), refined pergola terraces ideal for entertaining, and a private tennis court. From its commanding hilltop position, the estate delivers an unparalleled sense of privacy, security, and timeless elegance. Welcome home!

150 Old Farm Road N, Chappaqua

$2,650,000

5 Beds ⋅ 7 Baths ⋅ 929177 MLS

Welcome to an incredible retreat in beautiful Bedford, NY! This stunning 5-bedroom, 6.5-bath home spans over 10,000 square feet of elegant living space on nearly two acres of private land. From the moment you arrive, you will feel the warmth and sophistication of this well-designed residence. Step inside to find a gracious formal living and dining room that sets the tone for memorable gatherings. The expansive family room flows easily into a chef’s kitchen, complete with high-end appliances, custom cabinetry, and access to a spacious deck overlooking the grounds. The first-floor en-suite guest bedroom provides comfort and privacy, while the dedicated office offers a quiet place to focus or create. Upstairs, the primary suite feels like a personal getaway—featuring a cozy fireplace, two walk-in closets, a private balcony, and a luxurious bathroom designed for total relaxation. Three additional en-suite bedrooms and a wonderful bonus room complete this level, ensuring everyone has their own space. The lower level adds even more to love, with a media room for movie nights, a private gym, a walk-in spa like sauna, and a large family/game room with a full bar and bath that opens directly to the pool area . Outside, you’ll find a resort-like setting with an infinity-edge pool, relaxing spa, outdoor kitchen, and fire pit—perfect for unwinding or hosting. Set just 10 minutes from Scott’s Corners and downtown Bedford, this home blends tranquility with convenience, offering the best of refined living in a private, peaceful location.

496 Long Ridge Road, Bedford

$1,645,000

5 Beds ⋅ 5 Baths ⋅ 959315 MLS

Welcome to Somers Estates, one of Somers newest subdivisions. Custom designed Farm House where value meets Luxury. Situated on over a two acre level lot with space for a pool. 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 four 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.

Lot 11 Florence Drive, Somers

$850,000

3 Beds ⋅ 3 Baths ⋅ 923391 MLS

Nestled on 2 private acres and surrounded by historic 1800s rubble stone walls, this unique property offers a rare opportunity to create your dream retreat in one of the area's most peaceful settings. Rich in history, character, and natural beauty, the property features mature specimen trees, native plantings, vegetable and cut-flower gardens, and even remnants of 19th-century farm equipment that tell the story of the land's past. Outdoor living takes center stage with an in-ground pool, firepit, and two expansive decks designed for entertaining, relaxing, and enjoying the tranquil surroundings. The wooded acreage provides exceptional privacy, while the rear portion of the property offers potential space for a tennis court, sport court, or other recreational amenities. Inside, the home offers generous living spaces highlighted by a large stone fireplace and two wood-burning stoves, creating a warm and inviting atmosphere throughout the seasons. As spring and summer arrive, the property transforms into a private, park-like sanctuary beneath the canopy of a magnificent centuries-old Dutch Maple. Located just minutes from shopping, Town Center amenities, and major conveniences, the property combines the best of both worlds—peaceful seclusion with easy access to everyday needs. A rare offering for buyers with vision, this special property presents an opportunity to update and personalize a home in an extraordinary setting that cannot be replicated.

1780 Strawberry Road, Mohegan Lake

$5,995,000

6 Beds ⋅ 10 Baths ⋅ 950000 MLS

A Westchester masterpiece perfectly combining high end newer construction with A+ location. Set behind stone pillars, with impressive approach, courtyard and incredible curb appeal, this sophisticated, all stone, newer built estate is like no other on the market in this price range, with understated elegance, classic design and enhancement by sleek/modern amenities. Set majestically toward the end of exclusive Lincoln Lane, with over 10,000 sq.ft. of luxuriously appointed space, the finest finishes & incredible amenities, this custom built and professionally designed home is of the highest caliber in every respect. Three room office space connected, yet separate and private, is an unbeatable extra. Full and separate 1 bedroom guest space apartment also an incredible plus. Magnificent lower level of such high caliber that it replicates additional high end entertainment/gallery space and private professional fitness facility. Outdoor oasis is rich with private rolling lawns, beautiful gardens and magnificent pool. A rare offering in the most coveted location with incredible inherent value, unmatched by any new construction offering on the market

21 Lincoln Lane, Purchase

$3,395,000

4 Beds ⋅ 5 Baths ⋅ 920495 MLS

Exciting price improvement! This rare architectural masterpiece presents a once in a lifetime opportunity for a lucky buyer. Introducing Terry Manor, a beautifully and thoughtfully restored and completely renovated architectural treasure that seamlessly blends modern sophistication with timeless architectural detail and craftsmanship. Perfectly nestled in the heart of distinguished Lawrence Park West, this residence is located within a short walk to Bronxville Village and less than 30 minutes from Manhattan, offering the perfect balance of suburban tranquility, city convenience, and low taxes! Originally crafted by celebrated architect Lewis Bowman as the dream estate for Paul Terry, creator of Terrytoons, 21 Hampshire Road features a rich cinematic history and has recently appeared on HBO and NBC productions. Sophisticated finishes, exquisite artisanal tile and stonework, and state-of-the-art technology come together with striking details and bespoke touches to enjoy and impress at every turn. The elegance and warmth makes this residence equally suited for both formal entertaining as well as casual, everyday living. Noteworthy highlights of this spectacular Tudor include a beautiful formal living room with a barrel ceiling, magnificent restored Cuban mahogany wood paneling, and an original wood-burning fireplace with Rare Rosso Levanto marble surround and herring-bone limestone interior, all in pristine condition. The gourmet chef's kitchen features top-of-the-line appliances, Calcutta Oro marble countertops, including an oversized center island, luxurious custom cabinetry, and breakfast area which opens to a lovely family room with custom built-ins. On the second level, the primary bedroom suite impresses with soaring cathedral ceilings, a coffee/drink area, and a breathtaking spa-inspired bathroom featuring radiant-heated floors, a built-in sauna, and a dramatic hand-carved black granite soaking tub. A boutique-style dressing room and second full bath with a steam shower complete the primary bedroom retreat. Three additional bedrooms, including a guest bedroom with ensuite bath, ensure comfort and conveniences for family and visitors alike. The fifth bedroom was converted into a dressing room for the primary bedroom and can easily be converted back into an en-suite 5th bedroom while retaining a walk- in closet for the primary bedroom. Throughout the residence, each and every detail has been elevated: custom leaded-glass windows with double insulation, luxurious Rohl and Kohler fixtures, hand-selected tile and stone, and wide-plank white oak floors that radiate warmth. Smart-home technology takes center stage with voice-activated controls, video security, integrated sound, intelligent climate and lighting systems, and even smart pool and irrigation management—all designed to deliver ease and peace of mind. Outdoors, entertain, unwind, and savor the natural beauty of the private property situated on nearly one acre of beautifully landscaped grounds. The expansive slate terrace, complete with a wraparound design, built-in barbecue, and recently refinished pool with PebbleTec finish, new Pentair systems, and LED lighting, makes al fresco living effortless. Terry Manor is more than a residence—it is truly a legacy property with unmatched provenance, character, and contemporary luxury. Do not miss the opportunity to call this architectural masterpiece your home. Note: Please view the unbranded property video tour, https://bit.ly/21HampshireRoad

21 Hampshire Road, Bronxville

$28,500,000

8 Beds ⋅ 12 Baths ⋅ 915874 MLS

Symbolically built for the founding family of Purchase, this iconic estate presents an exclusive opportunity to acquire one of the most significant and unique New York residential real estate properties available in recent years. The epitome of a true suburban compound, this grand residence is uniquely situated within quick reach of New York City, water and golf amenities, and all means of domestic and international travel, presenting a priceless blend of lifestyle and convenience truly unmatched by any other property in the surrounding areas, including Westchester and Greenwich. Sitting majestically behind the gated approach to 41+ acres of enchanting and masterfully enhanced property, the 14,000+ square foot main house, rich in character and history, has been entirely and meticulously renovated to the highest caliber and with the most timeless, elegant and beautiful finishes. Creating a true compound landscape, the main house is completed by two additional guest residences, a multi purpose “hanger” and a free standing pool house -- all not included in square footage -- effortlessly enhancing every conceivable amenity and entertainment possibility. A thoughtful and artistic blend of design, function, beauty and grandeur, the “Arrow Hill” estate offers an array of both intimate and over sized terraces and reception lawns, perfect for events both large and small. Adorning these outdoor spaces you find the collection of exquisite garden statuary, elegant fountains, serenely crafted babbling brooks, ponds, and waterfalls as well as picturesque floral and english gardens, creating an atmospheric masterpiece of natural beauty. Venture along this breathtaking oasis down the inviting pebbled pathways complimented by ornamental trellis and curved allee of specimen trees and vine canopies. Living art abounds in the masterful placement of incredibly crafted koi ponds, reflecting gardens and an enormous greenhouse. Sporting and adventure seekers will enjoy the resort size pool, outdoor tennis court with spectator/entertaining terrace, indoor sports court, full gym, numerous trails and the incredible “catacombs”. The extensive acreage of additional picturesque level property and trails that lie beyond these magnificent spaces provides the unique opportunity for possible equestrian facilities or any other conceivable enjoyment, collection or opportunity imaginable, masterfully adding to, and without compromising, the integrity, beauty and privacy of this majestic home. A true work of art, and until now, virtually an unattainable blend of grand suburban compound living, right within the midst of the incomparable city life of iconic Manhattan.

2525 Purchase Street, Purchase

$3,495,000

6 Beds ⋅ 11 Baths ⋅ 911637 MLS

Major reduction . Home owner wishes to move on. Nestled on over two acres of secluded, picturesque grounds, this exceptional, one-of-a-kind contemporary estate is a rare opportunity for luxury living. It boasts a stunning pool with hot tub ,waterfall, a pavilion with full bath and changing rooms, and a tennis court. The striking architecture seamlessly blends indoor and outdoor living. Expansive spaces are accentuated by soaring ceilings and glass walls, creating the perfect environment for intimate gatherings and large-scale entertaining. The home offers every imaginable amenity, ensuring a lifestyle of comfort and elegance. This beautifully constructed and maintained residence offers modernized heating and air conditioning systems, ensuring optimal comfort year-round. The pool and tennis court have been meticulously maintained. near downtown Rye, shops and restaurants, and Harrison, White Plains, and Greenwich, easy commute to NYC. Come and visit 40 Poly Park Road. Additional Guest Quarters, Tennis, 3 Car Attached, extra parking

40 Polly Park Road, Rye

$7,450,000

6 Beds ⋅ 10 Baths ⋅ 911214 MLS

Just one hour from Manhattan, this extraordinary Bedford Corners estate offers the ultimate in privacy, scale, and resort-style living. Encompassing 14,000 square feet of custom design on 11.27 gated acres, the residence combines timeless sophistication with every modern amenity. Perfect for either a primary or weekend residence. A Retreat for Living, Working and Entertaining The grand entry opens to sunlit living spaces and a dramatic 20-foot ceiling family room, anchored by a soaring floor-to-ceiling stone wood burning fireplace. Expansive entertaining rooms flow seamlessly to outdoor terraces and landscaped grounds. A grand formal dining room accompanied by a newly renovated chef’s kitchen sets the stage for both intimate dining and large-scale entertaining. For work or study, a distinguished office /library, richly finished in teak wood, with a wood burning fireplace provides a warm and refined setting - ideal for remote work, private meetings or quiet reading. Luxurious Private Quarters The residence features six bedrooms, including a serene primary suite with a wood burning fireplace, private sitting room, enclosed porch, and dual custom dressing rooms. Two bedrooms are located on the main level for flexibility, while the upper level offers four additional bedrooms plus a bonus media/theater room. An elevator services all floors for effortless convenience. Resort-Style Amenities Designed for year-round enjoyment, the estate offers an unmatched collection of amenities: Outdoor pool & spa with expansive stone terraces Air-conditioned pool house with full kitchen and bath Indoor swimming pool & spa for four-season use Australian classic clay tennis court for the avid player Gated entry for privacy and security Custom windows & doors and plenty of closets and storage space. Recent Enhancements The property has been meticulously updated with a new roof, modernized mechanical systems, freshly painted and a renovated kitchen, ensuring turnkey comfort. An Exceptional Offering Perfectly blending country serenity with proximity to New York City, this Bedford Corners estate delivers a rare opportunity: a private compound with resort-level amenities just minutes from both the charming village of Bedford & the city of Mount Kisco with shopping, restaurants and a hospital. Private resort style living less than a one hour commute to Manhattan.

284 W Patent Road, Bedford

$3,250,000

5 Beds ⋅ 6 Baths ⋅ 904836 MLS

Welcome to 20 Stonewall Circle, a stunning residence offering over luxury living in the heart of West Harrison. This home features elegant flooring , a state-of-the-art kitchen with stainless steel appliances and Sub-Zero refrigerator, and expansive living spaces designed for both comfort and entertaining. Enjoy a private home movie theater, fully equipped home gym, and a large master suite for true relaxation. Step outside to your resort-style backyard with a beautiful inground pool and waterfall feature. Perfectly situated for commuters with easy access to NYC, and just minutes from Westchester Airport, this home combines convenience with sophistication.

20 Stonewall Circle, West Harrison

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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.