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

$899,000

3 Beds ⋅ 2 Baths ⋅ 1056752 MLS

Welcome to 79 Cliffside Drive! This home is way more than meets the eye. Tucked away on a quiet street in a desirable Yonkers neighborhood, this spacious 3-bedroom, 2-bath ranch offers the perfect blend of comfortable everyday living and exceptional entertaining space—including a unique indoor pool! The thoughtfully designed main level features a beautifully updated kitchen that flows seamlessly into the dining and living areas. Hardwood floors, a cozy fireplace, and custom built-ins add warmth and character to the inviting living room. All three bedrooms are conveniently located on the main level, including a primary suite with a beautifully renovated private bath, and an adjacent walk-inn closet and main floor laundry. A heated enclosed porch offers additional space to relax and leads to the home's most distinctive feature: an enclosed indoor pool with skylights, offering the opportunity for swimming and entertaining you can't usually find in Westchester. The finished lower level provides even more flexibility, with two versatile rooms ideal for a home office, playroom, recreation room, or whatever suits your needs, plus direct access to the oversized two-car garage. Outside, enjoy a beautifully landscaped property featuring mature plantings, stone retaining walls, a paved patio, and an organic garden bed. Recent improvements to the front steps and stonework add to the home's curb appeal. Conveniently located near the Crestwood Metro-North station, the shops and restaurants of Tuckahoe Village, and Central Avenue, this one-of-a-kind home offers space, character, and a lifestyle that's anything but ordinary!

79 Cliffside Drive, Yonkers

$1,399,000

5 Beds ⋅ 4 Baths ⋅ 1061797 MLS

Welcome to 31 Brendon Hill Road! Nestled on a desirable corner lot in the highly sought-after Beech Hill community of Scarsdale, this beautifully renovated, move-in-ready home offers the perfect blend of modern luxury, elegance, and convenience. Featuring a stunning brand-new kitchen with granite countertops and stainless steel appliances, beautifully updated bathrooms, gleaming hardwood floors, elegant crown molding, and exquisite marble arches that add a touch of timeless sophistication and architectural charm throughout. The exterior is equally impressive, boasting a circular driveway, charming flagstone patio, and an unfinished in-ground pool with a waterfall feature, offering incredible potential to create your own backyard oasis. Conveniently located near the Crestwood Metro-North train station, major highways, public transportation, shopping, and dining, with New York City just a short drive away. Situated in one of the area’s most desirable communities, this exceptional property offers comfort, style, and an unbeatable location. A truly move-in-ready gem you won’t want to miss. Schedule your private showing today!

31 Brendon Hill Road, Scarsdale

$824,222

3 Beds ⋅ 2 Baths ⋅ 1063448 MLS

Charming split-level home located in the heart of Briarcliff, just a short walk to the elementary school. Nestled on a peaceful dead-end street, this inviting residence awaits your personal touch to make it truly shine. The spacious living room features hardwood floors and a cozy fireplace, seamlessly opening to the dining area—perfect for gatherings. The modern kitchen boasts granite countertops, stainless steel appliances, a double wall oven, and an induction cooktop, with a door leading to a rear deck that awaits renovation. Inside, you'll find three bedrooms, two full bathrooms, and a versatile lower level with ample unfinished space, a laundry room, and a den that opens to the backyard. The fenced-in saltwater pool, last opened in 2018, offers fabulous outdoor enjoyment in a scenic setting. Take advantage of the vibrant Briarcliff recreation department, offering a variety of programs and activities for all ages. This lovely home combines convenience, comfort, and community charm—a perfect place to call your own. Pool sold in as-is condition. There are no audio recording devices inside this property.

133 Washburn Road, Briarcliff Manor

$949,000

3 Beds ⋅ 3 Baths ⋅ 1061975 MLS

Welcome to 125 Betsy Brown Road, a charming and inviting home filled with soaring ceilings, abundant natural light, and beautiful perennial plantings that provide color throughout the seasons. Offering a desirable first-floor primary suite, generous living spaces, and a spectacular resort-like backyard, this home is truly something special! The first floor features a welcoming den/family room, a sunken living room with custom built-ins and a wood-burning fireplace, and an open formal dining room with picture windows overlooking the stunning backyard. A sunroom with walls of windows brings the outdoors in, while the spacious kitchen and fabulous retro powder room add to the home's unique character. Upstairs, a charming reading nook offers the perfect spot for a home office, complemented by two generously sized bedrooms with abundant storage and a hall bathroom. The expansive lower level offers endless possibilities, with laundry, storage, and plenty of space to create a gym, playroom, or additional recreation area. The pièce de résistance is the spectacular backyard, featuring a saltwater pool and spa, beautiful bluestone patio, lush landscaping, exceptional privacy, and a fully fenced yard. It truly feels like being on vacation all year round! Filled with warmth, character, and space galore, this special home offers easy living inside and out. A must-see!

125 Betsy Brown Road, Port Chester

$3,595,000

5 Beds ⋅ 6 Baths ⋅ 1063259 MLS

Set on nearly three acres in Bedford, this circa 1800 Federal-period home was taken down to its original frame and rebuilt entirely new: every system, every surface, every detail. What remains is the architecture: the symmetry, the proportion, the restraint that made Federal design endure. Everything else is new. Inside, the details were chosen to belong. Millwork from Brent Hull's historically drawn Colonial collection holds the period proportions. Narrow-plank oak floors are laid as they would have been two centuries ago. Then the house gives you what no house of 1800 could: five bedrooms, each with its own en-suite bath and walk-in closet, a primary suite with a private sitting room, a second-floor laundry, and tall ceilings that carry light deep into the home. The kitchen is the center of the house, with custom cabinetry in a quiet period palette, an Italian range with brass burners set against a full-height marble backsplash, and a butler's pantry alongside for entertaining. Beyond the doors, a saltwater pool and bluestone terrace sit quietly behind old stone walls. Everything one would rather not think about is new: central heat pump systems, plumbing and electrical, the septic system, and the well pump. The past where you see it, the present where you live it. A few minutes from Bedford Village and an easy drive to the Mount Kisco train. A new home wearing two centuries of character.

126 McLain Street, Bedford Corners

$605,000

2 Beds ⋅ 2 Baths ⋅ 1063349 MLS

Welcome to this beautiful home in Mount Vernon, NY! This is a great starter home offering comfort, space, and convenience. The home features 2 generously sized bedrooms, 2 bathrooms, additional attic space for storage, and a spacious basement that can be used for a home office, recreation area, or additional living space. Included with the sale of the home are also a washer and dryer that are only 3 months old, an almost-new 4-piece sofa set with a matching ottoman, an extra refrigerator in the backyard, and a stand-up deep freezer. Conveniently located close to shopping, schools, doctors’ offices, hospitals, and other everyday essentials. Don’t miss this wonderful opportunity to own this beautiful home! Seller's information is deemed reliable but is not guaranteed. Buyers are encouraged to conduct their own due diligence and independently verify all information before making a purchase decision

115 S 9th Avenue, Mount Vernon

320 Saw Mill River Road, Yorktown Heights

$2,275,000

4 Beds ⋅ 4 Baths ⋅ 1054929 MLS

Welcome to 320 Saw Mill River Road; an exceptional private estate set across more than 10 acres, where bespoke craftsmanship, expansive grounds, and an extraordinary outdoor lifestyle come together. Across from the Croton Reservoir, tucked away down a driveway surrounded by mature trees and beautifully landscaped grounds, the cedar-shingled residence comes into focus. The home offers nearly 5,000 square feet of living space with 4 bedrooms, 4 baths and tons of flex space. The thoughtfully designed floor plan creates an effortless connection between the interiors and the landscape, with generous windows, beautifully proportioned living spaces, and an easy flow that brings the outdoors in. Bespoke details throughout lend the home a sense of warmth, character, and individuality. Outside, the property becomes its own private sanctuary. A heated in-ground Gunite pool with matching pool-house is beautifully set within the grounds, creating a resort-like setting for summer days and entertaining. A wrap-around porch and charming pergola anchors the backyard, offering an inviting space for al fresco dining, cocktails, and gatherings, while the fully fenced grounds provide exceptional privacy and room to enjoy the property to its fullest. The acreage is a defining feature. Included with the sale is an additional 3.72-acre lot, bringing the total property to more than 10 acres and creating a rare opportunity for multi-generational living, investment potential or simply the luxury of preserving additional open space. Located in the Yorktown School District, 320 Saw Mill River Road is a property of uncommon scale and privacy; where refined living, thoughtful design, and expansive land create a space that you will never want to leave.

320 Saw Mill River Road, Yorktown Heights

$839,000

3 Beds ⋅ 2 Baths ⋅ 1062826 MLS

PHOTOS TO BE ADDED 10/17 Welcome to 219 Remsen Road....a charming three-bedroom, two bath split level. This home needs some TLC but is perfect for the first time buyer or someone who wants to put in the work and make a great investment. Located in the Westchester Hills section of Yonkers, this home features spacious rooms, hardwood floors, attached garage, lawn irrigation, central AC, and so much more. The buyers of this home will be pleased with the large private yard, and enormous deck overlooking the Sprain River valley. This location of this home is ideal for commuters because it is within walking distance to the express bus or an eight-minute ride to Metro North.

219 Remsen Road, Yonkers

$1,100,000

4 Beds ⋅ 3 Baths ⋅ 1062680 MLS

*Interior Photos Coming Soon* Enter through white gates and discover a peaceful, private setting on over 2.5 lush, wooded acres. Set back from the road, this classic Colonial welcomes you with a dramatic two-story foyer and beautiful wood floors throughout. French doors open to the living room, where a fireplace creates a natural gathering space and sliders lead to the new synthetic deck. The living room flows into a charming breakfast area and an updated kitchen featuring quartz countertops, an oversized island, stainless steel appliances, and a generous pantry. To the other side of the foyer, French doors open to an expansive formal dining room, conveniently connected to the kitchen. Natural light fills the home, and a powder room completes the main level. Upstairs, the spacious primary suite offers a walk-in closet and a spa-like bath. Three additional well-proportioned bedrooms provide room for family, guests, or a home office. The lower level offers laundry, utilities, storage, and an area currently used for a gym and recreation space, with direct access to the spacious two-car garage. Outside, enjoy the beauty of the natural woodland surrounding the property, creating a wonderfully private setting for the house, lawn, and pool. The outdoor area also features an upgraded in ground pool and a pool shed. Recent improvements include a new roof, water heater, front walkway, and steps, along with the new synthetic deck. A classic home, generous space, and a beautiful natural setting come together to offer a wonderful place to call home.

2261 Hunterbrook Road, Yorktown Heights

$3,495,000

5 Beds ⋅ 5 Baths ⋅ 1060423 MLS

An unexpected blend of privacy, character and modern living, 79 Winfield offers a rare opportunity to enjoy a country-like setting with the convenience of the established & coveted Harrison neighborhood, Winfield Glen. Set on 3.21 beautifully landscaped acres, this 5-Bedroom, 4.5-Bathroom residence encompasses thoughtfully designed living space, where timeless architectural character meets contemporary sophistication. Meticulously restored and renovated with full completion in 2024, the home seamlessly balances its original charm with modern finishes and an effortless flow for today's lifestyle. Rich architectural details, inviting indoor & outdoor gathering spaces and a refined yet comfortable aesthetic create a home that feels both distinctive and welcoming. A private living wing off the main foyer provides an additional layer of versatility, featuring a separate gathering space with an bedroom/office tucked above—ideal for working from home, entertaining or creating a quiet retreat. Beyond the interiors, the grounds are equally compelling. Expansive lawns, wildflower meadows and a fabulous, heated & renovated inground pool create a picturesque backdrop for outdoor living, entertaining and enjoying the changing seasons. The property's natural beauty and exceptional privacy evoke the feeling of a country estate, while its location within a neighborhood and moments to town & train offers the best of both worlds. Whether envisioned as a full-time residence or a weekend escape, 79 Winfield presents a remarkable combination of space, setting and style—offering a sense of retreat without sacrificing proximity to everyday conveniences.

79 Winfield Avenue, Harrison

$5,499,000

7 Beds ⋅ 8 Baths ⋅ 1051060 MLS

A remarkable combination of timeless architecture, exceptional craftsmanship and modern luxury awaits at 270 Trenor Drive in New Rochelle. Custom built in 2008 and designed by an award-winning architect, this magnificent brick-and-stone Tudor offers approximately 10,393 sq ft, 7 bedrooms and 7.5 baths on a beautifully landscaped property. Thoughtfully designed for both grand-scale entertaining and everyday living, the residence showcases rich hardwood flooring, extensive custom millwork and cabinetry, gracious proportions and sophisticated architectural detailing throughout. The impressive kitchen is equipped for serious entertaining with two Sub-Zero refrigerators, three dishwashers, two sinks, Wolff double ovens and cooktop. The primary suite is a private retreat featuring a spa-inspired bath, generous walk-in closet and private balcony. Six additional bedrooms provide exceptional flexibility throughout the residence. Beyond the principal living spaces, this home delivers an extraordinary collection of amenities. Enjoy movie nights in the dedicated 10-seat home theater, maintain your routine in the fully equipped mirrored fitness room, or work from an impressive wood-paneled home office/library with custom built-ins and window seating. The residence also features a backup generator and has been framed for a future three-story elevator. Outdoors, the property becomes a private retreat. Mature trees and lush landscaping frame an expansive level lawn, while multiple stone patio and seating areas create inviting spaces for dining, entertaining and relaxation. At the center of the setting is a beautiful gunite swimming pool, surrounded by greenery and complemented by the home's striking Tudor architecture. Additional highlights include a heated three-car attached garage, marble bath, steam shower and dressing area. An exceptional opportunity to own a distinctive custom residence offering scale, craftsmanship and resort-style amenities within convenient reach of New York City.

270 Trenor Drive, New Rochelle

$4,700,000

7 Beds ⋅ 8 Baths ⋅ 1060497 MLS

Set on approximately 1.5 acres in Irvington's distinguished Ardsley Park neighborhood, this Georgian-inspired brick estate brings together enduring architectural character, thoughtfully updated interiors, and exceptional outdoor living. A gracious circular driveway introduces the home's symmetrical red brick facade, classic detailing, and beautifully established grounds. Inside, an elegant sequence of formal and informal spaces offers both architectural distinction and everyday comfort. The dining room is particularly memorable, with its intricately detailed ornamental ceiling, paneled walls, and fireplace. The living room and family room provide inviting gathering spaces, the latter distinguished by a coffered ceiling and French doors opening toward the gardens. The kitchen features a Wolf range, Miele fridge and freezer, 2 Bosch dishwashers and Calacatta Gold marble countertops, complemented by a light-filled breakfast room overlooking the grounds. Seven bedrooms and an array of flexible living spaces provide remarkable versatility, with accommodations for guests and spaces suited to home offices, fitness, and recreation. The primary suite features a dressing room and a marble-appointed bathroom with radiant heated floors and a steam shower. A separate guest suite with its own kitchen offers additional flexibility, while the west-wing recreation areas provide generous space for leisure and entertaining. Beyond the interiors, mature specimen trees, established flowering gardens, and a pollinator meadow create a landscape that evolves beautifully through the seasons. An oversized, recently resurfaced swimming pool that anchors the outdoor setting, complemented by a rebuilt stone patio and substantial pergola with a retractable roof. French doors establish a seamless connection between the home's principal entertaining spaces and the gardens beyond. Conveniently located near the Hudson River, Metro-North service, and the villages of Irvington and Dobbs Ferry, this distinguished estate offers a rare combination of architectural character, established gardens, and the flexibility to accommodate modern living.

1 Ardsley Avenue E, Irvington

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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.