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

$2,195,000

4 Beds ⋅ 4 Baths ⋅ 1023671 MLS

Perfectly situated on one of Bedford's quintessential country roads, this exceptional renovated 4-bedroom three-and-a-half bath home offers the ideal combination of privacy, timeless charm, and modern updates. Set on a beautifully landscaped property surrounded by mature trees, you'll enjoy complete tranquility while relaxing by the in-ground pool or entertaining on the expansive wraparound deck. Recently reconstructed retaining walls, seasonal gardens, and a brand-new perimeter fence further enrich the picturesque setting. A dramatic two-story entry welcomes you with a floating staircase and striking fieldstone chimney, creating an unforgettable first impression. Inside, soaring ceilings, abundant natural light and hardwood floors, create a bright and inviting atmosphere further enhanced by the addition of remote-controlled window shades throughout the home . The thoughtfully designed open floor plan is ideal for both everyday living and entertaining. At the heart of the home is the tastefully updated kitchen with door to fabulous wrap around deck. The Kitchen is open to the formal dining room on one side and family room, warmed by a pellet stove, adding comfort and character during the cooler months, on the other side. The flexible floor plan includes a desirable main-level primary suite complete with a fireplace, spa-inspired bath and huge walk-in closet—an ideal retreat for guests or multigenerational living. Upstairs, the luxurious primary suite features a spacious bedroom, spa bath, gym or office, and door to finished attic space for additional storage. Two additional bedrooms, a full bath, and an open balcony overlooking the foyer complete the upper level. Additional highlights include a detached three-car garage with potential for future expansion above, a whole-house propane generator, and a security system for added peace of mind. Offering exceptional privacy in a spectacular Bedford setting, this is country living at its finest. Please note that pictures have been digitally staged.

230 E Middle Patent Road, Bedford

$2,595,000

4 Beds ⋅ 4 Baths ⋅ 1020428 MLS

INDOOR POOL! Primary on the main level. Set behind gates on more than 13 acres, with an indoor pool, this subdividable, thoughtfully renovated country property offers a rare combination of privacy, space, and convenience just minutes from the heart of Katonah. With over 4,000 square feet of updated living space, the home features a welcoming layout designed for comfortable everyday living and entertaining. Seasonal glimpses of the reservoir complement the property's natural setting. The home includes four bedrooms - primary on the main level; four renovated baths; an updated kitchen; expansive gathering spaces; and a heated indoor pool that provides year-round enjoyment -- an amenity rarely found in the area. Large windows bring in abundant natural light and frame views of the surrounding landscape. Recent improvements, including a new roof, energy-efficient windows, all-new plumbing, durable Hardie(R)Plank siding, and extensive interior renovations, provide the benefits of modern updates along with peace of mind. Whether as a full-time residence or a weekend retreat, this distinctive property offers generous acreage with easy access to Katonah Village, Metro-North, schools, and major commuting routes. A unique opportunity to enjoy updated country living in one of northern Westchester's most desirable locations.

380 Cross River Road, Katonah

$995,000

3 Beds ⋅ 4 Baths ⋅ 1022785 MLS

Escape to this charming country retreat where privacy, comfort and timeless style come together. Nestled on a peaceful setting, this inviting home features a beautiful landscaped yard with a sparklinig inground pool - perfect for relaxing or entertaining. Inside the heart of the home is a gorgeous kitchen with quality finishes and abundant workspace flowing seamlessly into a bright and welcoming sunroom that overlooks the property. Custom built-ins add warmth, character and functional storage throughout the home. With a flexible floor plan that lives like a 4-bedroom home, this property offers versatile spaces ideal for guests, a home office or growing needs. Part of the original College Hill land purchase of over 100 acres purchased and built for Columbia University professors this neighborhood is characterized by winding, tree-lined roads, large wooded lots and natural settings. All conveniently located minutes from Cortlandt Metro North Station, shops, markets, schools, highways and more.

69 Montrose Station Road, Montrose

$2,547,600

4 Beds ⋅ 7 Baths ⋅ 1014155 MLS

Set on over two acres of beautifully curated private grounds, Architect Jack Travis reinvented this 1925 home into an eclectic contemporary retreat. Designed for both elegant entertaining and serene everyday living, this property blends modern architecture with natures beauty. Framed by oversized windows on three sides, this light-filled space offers uninterrupted views of lush manicured lawns, mature trees and views of the Hudson Palisades from the primary-suite balcony. The Layout is both Functional and refined, with generous living spaces. This home is an architectural masterpiece with its geometrical textures, this striking home stands out from the crowd. The home Includes 1st floor primary- suite and a 2nd floor primary- suite and balcony, two additional ensuite bedrooms, the lower level has an additional room perfect for yoga studio or home office, a dog grooming station was added in the basement for doggie owners convenience. a professional grade kitchen, heated four car garage, gym and home theatre. This magnificent home offers outside entertaining, complete outdoor kitchen with BBQ station. Serene pool patio and garden, free-form heated in-ground pool & hot tub . Half hour train ride to Grand Central Station. Close to downtown Hastings retail and restaurants. Recent renovations and upgrades, new mechanicals, heating and cooling systems and total home solar power for green efficiency.

150 Pinecrest Drive, Hastings-On-Hudson

$2,995,000

4 Beds ⋅ 6 Baths ⋅ 1022183 MLS

Ultra Private Country Estate - Only 40 Minutes From NYC - The Perfect Setting - Peaceful 2.3 Acre Horticultural Oasis - Irvington, NY - Luxurious Mid-Century Modern Home With Pristine Gardens & Grounds - Majestic Shade Trees, Flowering Shrubs, Specimen Plantings & Athletic Field Sized Lawns - Generously Proportioned Rooms, King-Size Outdoor Decks & Abundant Parking Make This Home Ideal For Formal Entertaining or Accommodating Out-Of-Town Guests || GENERAL INFO || ** 5,500 sq ft, 4 bedroom, 5.5 bath home on a lush 2.3 acre oasis ** Sunny & bright 4,700 sq ft main living area ** Plus an additional 800 sq ft two-room office suite w/full bath, wet bar & separate parking area || MAIN LIVING AREA || ** Entry hall with coat closet & powder room ** Grand LR w/floor-ceiling windows, 16’ cathedral ceiling, wood burning fplc hdwd flrs & French doors to king size (650 sq ft) ipe wood deck ** Formal dining room ** Huge skylit gourmet kitchen w/designer cabinets, granite countertops & top-of-the-line appliances ** Adjoining breakfast dining area with SGD to x-large (600 sq ft) ipe wood deck ** Skylit library with granite fireplace & built-in bookcases ** Home office with built-in workstation, bookcases & large windows overlooking backyard || BEDROOM WING || ** Hall bath w/tub ** BR #1, BR #2, BR #3 (former MBR) with WIC & luxury bath w/marble counters, twin vanities & spa shower || 2nd FLOOR MASTER BEDROOM SUITE (844 sq ft) || ** Spacious master bedroom with cathedral ceiling & extra large windows overlooking lush backyard ** Two extra-large WICs ** Luxury bath w/marble counters, twin vanities, non-slip floor, jacuzzi & walk-in spa-style shower || LARGE EXERCISE ROOM || ** Hallway w/two cedar closets & full bath ** Extra large (450 sq ft) solarium-fitness room w/vaulted ceiling & 12’ wide SGD doors to large bluestone patio ** Heated Endless Pool (7’ x 14’) ** Independent climate controlled HVAC system || TWO-ROOM PROFESSIONAL OFFICE SUITE (800 sq ft - potential guest, in-law, nanny suite) || ** Private professional office with closet ** Waiting room with private entrance ** Full bath ** Wet bar ** Independent HVAC system ** Separate 6-car parking area || ADDITIONAL FEATURES || ** Meticulously maintained inside & outside ** No-step entry ** Main floor bedrooms ** Attached two car garage with additional 2-car parking apron ** 2 fireplaces ** 2 king-size decks ** Extra-large bluestone patio ** Automated irrigation system ** Three independent HVAC systems ** Propane-fueled generator ** Fire sprinkler systerm ** Additional 6-car gravel parking area ** Spacious walkout storage basement ** Centrally monitored security system ** Town of Greenburgh ** Town park privileges ** Irvington School District ** Short walk to 400 acre Irvington Woods & Irvington Nature Center ** 40 minutes to NYC by train or car ** 10 minutes to Mario Cuomo Bridge ** 20 minutes to downtown White Plains

353 Mountain Road, Irvington

$1,350,000

4 Beds ⋅ 5 Baths ⋅ 1020887 MLS

Welcome to 12 Mount Airy Road East, an exceptionally well maintained 4-bedroom, 4.5-bath residence set on just over 2 private acres in the highly regarded Croton-Harmon School District. Thoughtfully designed with timeless elegance and modern luxury in mind, this impressive home offers expansive living spaces, soaring ceilings, oversized windows that fill the home with natural light, and refined finishes throughout. The open-concept main level seamlessly connects the living room with wood-burning fireplace, dining area, chef-inspired kitchen featuring a dramatic waterfall island and stainless steel appliances, and a spacious family room warmed by a double-sided wood-burning fireplace. Just beyond, a tranquil sunroom opens to the backyard, creating an effortless indoor-outdoor lifestyle ideal for both everyday living and entertaining. The spacious primary suite offers a private retreat complete with a balcony, two walk-in closets, and a spa-inspired en suite bath featuring a deep soaking/jacuzzi tub, oversized shower, and double vanities. Each level of the home includes a full bathroom, while generous closet space, recessed lighting, designer chandeliers, and an upstairs laundry area provide exceptional comfort and convenience throughout. The fully finished lower level expands the living space with a recreation room, kitchenette/wet bar, three versatile bonus rooms suitable for a variety of uses, abundant storage, and direct access to the attached two-car garage. Outside, enjoy resort-inspired amenities including a fenced tennis and basketball court, in-ground pool, pergola-covered patio, additional patio space, inviting front porch, and an expansive driveway leading to the home, offering privacy and an impressive arrival experience. Conveniently located near Croton Point Park, Senasqua Park, Silver Lake Park, Teatown Lake Reservation, Hudson River waterfront parks, hiking and biking trails, and the vibrant restaurants, cafes, and boutiques of downtown Croton-on-Hudson. Enjoy easy access to Route 9, the Taconic State Parkway, the Croton Expressway (Route 202), and the Croton-Harmon Metro-North Station, offering express service to Grand Central Terminal in approximately 50 minutes. This remarkable property combines sophisticated design, exceptional amenities, and a premier location, offering an extraordinary opportunity to enjoy refined Hudson Valley living.

12 E Mount Airy Road, Croton-On-Hudson

$1,650,000

4 Beds ⋅ 7 Baths ⋅ 1014445 MLS

Katonah, swim at your private oasis, this multi-functional home with in-law capacity, entertainment amenities, and office workspace is nestled on almost 3 acres of lush parklike property. Enjoy the ease of being close to town, elementary school, and Metro-North; this exceptional 3,738 sqft residence offers the perfect blend of tranquility and commuter convenience. Designed with flexible home features including an open floor plan with soaring vaulted ceilings, skylights, full office suite, and beautifully refinished hardwood floors. Offering 4 bedrooms that live like five, along with 4 full and 3 half baths, the layout includes the option of a first-floor primary suite or an equally inviting second-floor suite. The finished lower level with walkout access to patio and gated pool, adds 2,186 sqft, and includes an entertainment area with fireplace, an abundance of storage, and changing rooms. Previously used as a doctor's office with a separate entrance and a renovated waiting area. The newly created chef's kitchen features a Sub-Zero refrigerator, all-new Bosch appliances, including an induction cooktop, quartz counters, and premium finishes. Many upgrades include new HVAC system, all new pool equipment, and freshly painted interior and exterior. Surrounded by mature landscaping, this gated and fully fenced property feels like a private retreat. A rare offering that is move-in ready yet brimming with potential. Some images have been virtually enhanced and/or virtually staged to help showcase the property's possibilities and potential use of space.

60 Cherry Street, Katonah

$900,000

4 Beds ⋅ 3 Baths ⋅ 1021042 MLS

This spacious and well-maintained single-family home offers the perfect blend of comfort, functionality, and convenience. Featuring 4 bedrooms and 2.5 bathrooms, this home provides ample space for today’s lifestyle. The main living areas are complemented by a full finished basement with a separate entrance, offering endless possibilities for recreation, a home office. An extension at the rear of the home adds valuable square footage, creating even more room for entertaining and everyday living. Outside, you’ll find a private backyard complete with an above-ground pool, perfect for enjoying warm summer days. The property also features a garage and a large driveway with parking for approximately four vehicles, providing plenty of off-street parking. Conveniently located in a desirable Yonkers neighborhood, this home offers easy access to major highways, public transportation, shopping, restaurants, schools, parks, and is an excellent location for commuters traveling to and from New York City. Don’t miss this opportunity to own a spacious home with exceptional indoor and outdoor living space in one of Yonkers’ most convenient locations! Schedule your private showing today.

104 Hayward Street, Yonkers

$2,750,000

3 Beds ⋅ 5 Baths ⋅ 1019351 MLS

No words or photos will justify the Magical beauty of this luxurious home. The woodwork in this custom built home was done by craftsman Mark Pedley, a very talented carpenter/joiner from Vermont who previously worked in Palaces in Jordan. The home is flawless and impeccable with spa like bathrooms, a gourmet kitchen, outdoor grilling area, sauna, steam bath and jacuzzi, with marble, granite and superior hardware throughout. The woods in the house are too numerous to list, but some of them are Mahogany, Red Maple, Pecky Cypress, White Oak, Utile (Mahogany type), Amboyna, Birch, Curly Birch, Bubinga, Red Birch, Maple, Maple Burl, and Walnut. All of the baseboards are double or triple layered with different wood species. All of the light fixtures, window dressings, and appliances stay with the home. The gourmet kitchen contains a steam oven, double drawer freezer full-size refrigerator, built in microwave, warming drawer, six burner stove, double oven, ice maker, separate built-in vacuum cleaning system. Additional square footage is on the basement level. This is a wonderful home surrounded by greenery to entertain guests or enjoy your privacy. Please see video link for a virtual tour.

23 Inningwood Road, Ossining

$7,695,000

6 Beds ⋅ 6 Baths ⋅ 1015115 MLS

Tucked away at the end of a long private drive, hidden from view and unknown to many who pass nearby, this extraordinary waterfront estate offers a rare combination of privacy, history, and lifestyle in one of Rye’s most coveted neighborhoods. Originally built in 1856 as part of the area’s original homestead and thoughtfully expanded and enhanced over the years, the property spans 1.59 spectacular acres along Milton Harbor with direct access to Long Island Sound. A world apart from the ordinary, the 5,233-square-foot residence is surrounded by breathtaking gardens, mature specimen plantings, and a series of enchanting outdoor spaces that unfold from one destination to the next. Multiple terraces invite al fresco dining and entertaining—from morning coffee overlooking the water, to sunset cocktails by the pool, to gatherings at the dock as boats return from a day on the Sound. With six bedrooms, five full and one half baths, four garage bays, a waterside pool, and a private dock accommodating a vessel up to approximately 32 feet, the property delivers an unrivaled waterfront lifestyle. The setting evokes a distinctive “Bedford meets the water” feel—an uncommon blend of estate-like grounds, privacy, and natural beauty rarely found on the shoreline. While the home enjoys all the benefits of the vibrant Hix Park neighborhood community, it lives as its own private sanctuary. This is not a cookie-cutter property. It is for the buyer seeking something truly unique: a place with history, character, extraordinary land, stunning gardens, a dock, pool, water access, and a sense of discovery that cannot be replicated.

87 Hix Avenue, Rye

$1,850,000

3 Beds ⋅ 4 Baths ⋅ 1017897 MLS

CIRCA 1880'S FARMHOUSE. Surrounded by breathtaking property! Old stone walls, specimen trees and flowering gardens. Carefully restored antique with wide board floors, period millwork and three fireplaces. Entry Hall with limestone floor. Beautiful Living Room with stone fireplace and French doors to the rear terrace and Sunroom. Formal Dining Room with raised paneling and stone-faced fireplace. Kitchen with Esmerelda granite counters and commercial grade appliances. Spacious Primary Suite with Sitting Room, fireplace and Bath. Guest Suite with Bath. Two additional rooms sharing Hall Bath. Detached Garage with fabulous Second Floor Game Room. Pool and spa. An incredible offering!

72 Old Mill River Road, Pound Ridge

$6,790,000

7 Beds ⋅ 9 Baths ⋅ 1005728 MLS

Cosseted within the gates of the exclusive Conyers Farm association with 24hr security, this baronial French Normandy chateau is poised on more than thirteen park-like acres. Hospitality sets the tone from the entrance through the grand foyer to the dual living rooms, an impressive formal dining room for large-scale entertaining and a warmly paneled library. The heart of the home is the luxurious kitchen with butler's pantry, breakfast room and adjoining family room with fireplace. French doors open to the immense terrace, perfect for outdoor dining. A true sanctuary, the primary suite features two bathrooms, two sizable walk-in closets, a dressing room and a romantic sitting room with balcony overlooking the naturally secluded, private backyard. Six additional bedrooms offer abundant space for guests or family. Creating captivating vignettes of multifunctional living, the lower level features a home theater, sitting room with fireplace, full bar with kitchenette, gym, indoor resistance pool and a hot tub. Outside the terrace overlooks beautiful, level lawns and a pool with spa. Peace of mind is the directive for this characterful estate, with its reassuring security in a guard-gated enclave and its luxury leisure amenities.

4 Cowdray Park Drive, Armonk

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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.

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

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Tierra Stanback