Homes for Sale with a Pool in Westchester, NY

Advanced Search Market Reports Home Value Connect

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.

< Back to all Homes for Sale in Westchester, NY

Search Westchester, NY by Lifestyle

All Homes for Sale with a Pool in Westchester, NY

$589,000

4 Beds ⋅ 2 Baths ⋅ 1031166 MLS

This 1800's Colonial offers a hidden backyard with in-ground pool/Formal and versatile living space is found throughout the home/A wide covered front porch, large living room and formal dining room, Eat-in-Kitchen along with full hall Bathroom compliment the main living level. There are two backyard access points from the Kitchen & Hallway too . . The Primary bedroom w/sitting room, is on the Upper level - along with three other Bedrooms & Hall Bathroom. . The finished Lower-level offers a Recreation Room w/built-in storage, Office Rm, Mud Rm and access into the unfinished Laundry Area. Gas hot/water heating system, Replacement windows, wide-plank floors, Stucco & Brick exterior siding, EV Charging station are amenities worth noting. The home had been utilized as a two-family years past. And while the zoning allows for it's current use, the floor-plan is flexible to suite your needs. Neighborhood shops, bus stop & Veterans Park are all close by and accessible via sidewalks. If commuting into NYC is needed, the Metro-North R. R. offers Express (45 mins) trips into GCS. Potential STAR savings of $1659/yr is not reflected in noted taxes.

41 Campwoods Road, Ossining

$5,650,000

6 Beds ⋅ 7 Baths ⋅ 935005 MLS

Work is underway! An exceptional opportunity to own a newly built, ultra-luxury estate perfectly sited on over five pristine, private acres—just three minutes from Bedford Village. This chic, sun-drenched Modern Traditional features six ensuite bedrooms, a covered terrace, and a sparkling heated Shoreline pool and spa. The home is part of Hemlock Hills, an exclusive enclave of seven custom residences, showcasing masterful construction by award-winning luxury builders Simone Development. Privacy is assured in perpetuity, as Hemlock Hills adjoins the protected open land of the Rockefeller Preserve. This spectacular new build blends the best of comfort, convenience, and cutting-edge amenities—while giving buyers the opportunity to custom-design the finishes in their dream living space. Every inch reflects exceptional craftsmanship, from immaculate white oak floors and oversized, high-end Marvin windows to dramatic double sets of French doors and exquisite stonework. Impeccable infrastructure and precision engineering are a Simone signature—even the mechanical room is a marvel. Designed for effortless living and entertaining, the open floor plan enhances flow and blurs the line between indoors and out. The kitchen, with ten-foot ceilings, is a showstopper—anchored by a Wolf range, Sub-Zero refrigerator, custom cabinetry, and a dedicated coffee bar. From here, the layout sweeps through the dining room and great room to a covered veranda —heaven for year-round gatherings. The foyer offers a panoramic front-to-back introduction to the home, including views. Upstairs, the primary suite is a retreat with a spa-worthy bath featuring custom cabinetry, an oversized shower, soaking tub and massive dual walk in closets. A three-car garage, with separate heating and AC, boasts a durable epoxy floor and an EV charging outlet. Buyers can opt for personalized upgrades such as a custom cabana, outdoor kitchen and bar, and lower-level golf simulator. All this is just minutes from Bedford Village.

2 Hemlock Hill Lane, Bedford

210 Sandpiper Court Unit #210, Yorktown Heights

$590,000

2 Beds ⋅ 3 Baths ⋅ 1030986 MLS

A Rare Three-Level, Two-Bedroom Opportunity in Maple Brook! Spacious, bright and beautifully designed, this Maple Brook townhome offers three levels of versatile living space—and is currently one of only two three-level, two-bedroom units available in Yorktown. The main level features an eat-in kitchen with Corian countertops and pantry, dining area, den/home office and an inviting living room with fireplace, soaring vaulted/cathedral ceilings and sliding glass doors to the deck. A convenient half bath completes this level. Upstairs, you’ll find two generously sized bedrooms, each with a walk-in closet, along with two full baths. The finished lower level adds approximately 600 square feet of flexible space with a recreation/play area, TV space, storage room and sliders to the patio—ideal for relaxing, entertaining, hobbies or working from home. Additional highlights include abundant storage, four-car tandem parking and a desirable cul-de-sac location. Enjoy Maple Brook’s community pool and tennis, plus convenient access to Jefferson Valley Mall, shopping, dining and the Taconic State Parkway. The Peekskill train station is approximately 10 miles away. With three finished levels and flexible spaces that can adapt to today’s lifestyle, this Maple Brook townhome is an opportunity you won’t want to miss!

210 Sandpiper Court Unit #210, Yorktown Heights

$595,000

2 Beds ⋅ 2 Baths ⋅ 1027781 MLS

Recently price adjusted and offering exceptional value! Welcome to this turnkey two-bedroom, two-bath attached home in the sought-after Chapel Hill community. Thoughtfully updated with a new roof, new siding, new hardwood floors, new recessed lighting, a completely renovated first-floor bathroom, fresh interior paint, and Andersen sliding and storm doors. The open loft is perfect for a family room, while the finished lower level provides ideal space for a home office. An oversized one-car garage offers additional convenience and storage. Chapel Hill’s impressive amenities include a clubhouse, swimming pool, fitness center, tennis and pickleball courts, and a bocce court. Move right in and enjoy everything this exceptional home and community have to offer. Enjoy nearby Riverfront Green, Depew Park, the Paramount Hudson Valley Theater, and convenient Metro-North service to New York City.

3302 Homestead Court, Peekskill

Lot 1 118 Kincart Court, Yorktown Heights

$1,750,000

4 Beds ⋅ 3 Baths ⋅ 1029729 MLS

New Construction - The Fairmont Model Welcome to Dorchester Glen Estates a Premier Luxury Development. Choose One of our plans or bring your own. Builder will build to suit. Nestled in the heart of southern Yorktown Heights, this exclusive community combines sophistication, serenity, and convenience. Each residence is thoughtfully situated on expansive acreage, offering unparalleled privacy amid lush greenery and mature landscapes. Designed for those who value both space and style, the development provides a rare balance of luxury living and natural beauty. Just minutes away, you’ll find fine dining, charming local restaurants, and vibrant shopping destinations. Easy access to major highways and nearby train stations ensures seamless travel to New York City and beyond, while the surrounding parks and nature trails invite you to enjoy the outdoors right at your doorstep. This is more than a home—it’s a lifestyle defined by elegance, comfort, and connection to nature.

Lot 1 118 Kincart Court, Yorktown Heights

$1,279,000

5 Beds ⋅ 5 Baths ⋅ 1030029 MLS

Welcome to 8 Fairgreen Court in the highly sought-after town of Cortlandt Manor! This incredibly bright and expansive Colonial-style home, situated on just shy of a full acre, is an entertainer’s dream come true! Step through the hand-carved doors into a massive two-story foyer featuring gleaming hardwood floors throughout. The enormous center island chef’s kitchen boasts granite countertops, stainless steel appliances, a matching farm sink, and a wine cooler—perfect for hosting gatherings. Sliding glass doors lead from the kitchen onto a gigantic deck overlooking a expansive in-ground pool and a beautiful rock garden. The family room impresses with cathedral ceilings and a cozy pellet stove, flowing seamlessly into an additional four-season room. The generous primary suite offers two walk-in closets, a vanity, and a full bath. Three additional bedrooms—including one en-suite—and two full baths complete the second floor. The legal in-law or au pair suite on the lower level includes a renovated kitchenette, a full bathroom, a large bedroom, and an enormous playroom with sliders to the backyard, providing privacy and comfort. Additional Features: Stall shower Extra storage Oil above-ground heating In-ground pool Beautiful Mountain views Attached 2-car garage parking This home perfectly balances luxury, comfort, and functionality in a prime location!

8 Fairgreen Court, Cortlandt Manor

$2,785,000

4 Beds ⋅ 6 Baths ⋅ 1026033 MLS

BEDFORD SOPHISTICATE. Impressive and elegant Colonial with perfectly scaled rooms, high ceilings and incredible millwork. Comfortable, yet refined, living space with fine detailing and craftsmanship throughout. Beautifully appointed interior with open layout perfect for today’s lifestyle. Stylish main rooms for formal entertaining. Heart-of-the-home Family Room open to gorgeous Chef’s Kitchen. Elegant Primary Suite with spa Bath. Three additional Bedrooms. Spacious Bonus Room with Guest Room. Lower Level with Recreation Room and Home Theater. Whole house generator. Over five acres, fenced for deer, in one of the area’s finest estate areas. Fabulous screened porch and swimming pool for outdoor entertaining. A great outdoor lifestyle with walking trails down to a pond and stream. Convenient location just minutes from the shops of Katonah, Bedford Village and Bedford Hills. Easy access to Metro-North trains, the Sawmill Parkway and I-684. The perfect offering!

487 Bedford Center Road, Bedford

$1,499,418

5 Beds ⋅ 3 Baths ⋅ 1027495 MLS

78 Tuckahoe Avenue is a five-bedroom, three-bath home in the Eastchester School District close to Twin Lakes Nature Preserve, Lake Isle, and the shops on White Plains Road. At 2,234 square feet, freshly painted and meticulously maintained, it has the details that set a house apart: beamed ceiling, a tray ceiling in the primary bedroom, wood feature walls throughout and a flexible floor plan. The renovated kitchen, with custom cabinetry and Corian countertops, opens into a family room. Both have exceptional access to the outdoors: double French glass doors lead to an expansive deck and in-ground gunite pool, that was redone in 2024 with additional yard space set aside for play or relaxing. The main level also features the living room, dining room, powder room, and back staircase. Upstairs, the primary bedroom's tray ceiling stands out, alongside two more bedrooms (one with a custom accent wall, one with built-in bunk beds) and a renovated hall bath. The back staircase leads to one bedroom with a handicap-accessible bath and a bedroom with balcony. The lower level adds a recreation room, (the size of the family room and kitchen area) laundry room with a laundry chute, utilities, and direct garage access. Outside: a fenced yard, 4-car driveway, central air, retractable awning, and a fire pit by the pool. This is Eastchester living at it's best.

78 Tuckahoe Avenue, Eastchester

$950,000

4 Beds ⋅ 2 Baths ⋅ 1027547 MLS

Welcome to your Dream home on a Huge .49 Acre of Level land. Resort Style Backyard with your own Private Swimming Pool- A BEAUTIFUL 4-bedrooms, DEN- (POSSIBLE 5th BEDROOM) 2 Full Bathrooms - This home offers perfectly blend timeless elegance, everyday comfort, and is a one of a kind - Well-maintained ranch-style residence, perfectly situated in a peaceful and highly desirable neighborhood . Offering the ease of one-level living with no interior steps, this exceptional home combines comfort, elegance, and functionality throughout. Designed with an open and inviting flow, the home features a spacious living room highlighted by a charming fireplace, a Huge formal dining room ideal for entertaining, and a beautifully updated eat-in kitchen appointed with granite countertops, stainless steel appliances, and ample cabinetry. The private primary suite offers a spacious retreat with 2 Spacious Walk-IN Closets complete with its own full bath, while three additional generously sized bedrooms and a Nicely, Updated Full Hall Jacuzzi bath. This Home offers plenty of room for family and Guests! Enjoy gathering in the warm and inviting Den or step outside to your own private backyard oasis—perfect for relaxing, outdoor dining, and entertaining. Well- maintained and move-in ready, this home offers the perfect blend of style, comfort, and convenience. Ideally located close to shopping, dining, parks, transportation, and all that the area has to offer, this is a rare opportunity to own a truly special home in a prime location. A must-see property that showcases pride of ownership throughout.

208 Woodhampton Drive, White Plains

$1,250,000

5 Beds ⋅ 4 Baths ⋅ 1023996 MLS

Perfectly perched in one of Mount Pleasant's most desirable neighborhoods, this extraordinary 5-bedroom, 4-bath Colonial commands breathtaking western horizon views and offers a rare double-lot setting that delivers the privacy, space, and resort-style lifestyle few homes can match. Every inch has been thoughtfully reimagined with exceptional craftsmanship, designer finishes, and uncompromising attention to detail, creating a residence where luxury and functionality exist in perfect harmony. A charming breezeway/mudroom provides seamless access to both the attached garage and the main home before unveiling an interior that is nothing short of spectacular. The sun-filled living room welcomes you with a classic brick wood-burning fireplace, oversized picture window, and warm, inviting atmosphere. A first-floor bedroom creates the perfect guest suite, au pair quarters, or home office. At the heart of the home is a showstopping chef's kitchen designed to impress. Outfitted with premium stainless steel appliances, sleek glass-front cabinetry, striking glass tile backsplash, endless quartz countertops, a generous extended island, farmhouse sink, and a garden window perfectly framing the stunning western views, this space is both sophisticated and functional. Designed with effortless flow, the open-concept layout seamlessly connects to the inviting living room and gracefully transitions to the elevated dining room, creating an exceptional backdrop for everyday living and unforgettable entertaining. Upstairs, the luxurious primary suite is a private retreat featuring an expansive walk-in closet, spa-inspired ensuite bath, and direct access to a private balcony where morning coffee and spectacular sunsets become part of your daily routine. Three additional spacious bedrooms and a beautifully updated hall bath complete the second level. The walk-out lower level elevates this home even further, offering incredible versatility with an expansive family/media room, an impressive summer kitchen, a designer full bath with an oversized walk-in shower, and direct access to the backyard. Whether hosting, entertaining guests, or creating the ultimate recreation space, the possibilities are endless. Occupying its own separate deeded lot, this private outdoor sanctuary is truly one of a kind. The heated saltwater in-ground pool is surrounded by premium paver patios, lush landscaping, and complete privacy behind secure fencing. A built-in barbecue, authentic pizza oven, and multiple entertaining spaces transform every gathering into a vacation-worthy experience, while unforgettable sunset views create a backdrop that feels worlds away from it all. Adding to its appeal, this exceptional home is designed for modern efficiency with leased, transferable solar panels and a state-of-the-art Mitsubishi high-efficiency mini-split heat pump system, delivering year-round comfort and impressive energy savings. Located within the award-winning Mount Pleasant School District, residents enjoy access to the town pools, library, parks, recreation, shopping, dining, major parkways, and Metro-North for an easy commute. This is more than a home, it's a lifestyle, a private retreat, and a rare opportunity to own one of Mount Pleasant's most exceptional properties.

121 Marietta Avenue, Hawthorne

$490,000

2 Beds ⋅ 1 Baths ⋅ 1015097 MLS

Set back from the road on a picturesque, tree-lined property, this inviting home welcomes you with classic charm, lush landscaping, and exceptional curb appeal. Step inside to a welcoming foyer that opens into a cozy living room featuring a wood-burning fireplace and a decorative wall niche, perfect for displaying treasured photos, artwork, or decor. Down the hall, you'll find two comfortable bedrooms, each offering generous closet space and endless possibilities to make them your own. The kitchen is equipped with stainless steel appliances and ample space to prepare your favorite meals. Just beyond, the formal dining room provides a warm setting for everyday meals and special gatherings while offering convenient access to the unfinished basement, complete with a laundry area and abundant room for storage, a home gym, workshop, or future expansion. Indirect hot water heater with lifetime tank warranty. Additionally, the attic offers approximately 700 square feet of storage space, providing plenty of room for seasonal items, holiday decorations, and other belongings. Off the dining room, a versatile den creates the perfect space for a home office, playroom, or cozy retreat. From the den, step outside onto the spacious back deck, ideal for outdoor dining, entertaining, or simply relaxing while overlooking the backyard. Follow the deck stairs down to your own private oasis, where a large above-ground pool provides the perfect place to cool off, host family and friends, or enjoy sunny afternoons all season long. This home includes a one-car garage attached to the neighbor's garage with a new roof and a spacious driveway offering ample off-street parking for multiple vehicles. Ideally located for commuters, the home is just 10 minutes from the Taconic State Parkway, only 5 minutes from the Bear Mountain State Parkway, and approximately 15 minutes from the Peekskill Metro-North train station, providing convenient access to surrounding towns and an easy commute to New York City.

77 Baron De Hirsch Road, Crompond

$2,137,500

4 Beds ⋅ 6 Baths ⋅ 1025674 MLS

A rare opportunity to create a forever home on nearly 7 private acres in the Chappaqua School District. Rich in history, character and natural beauty, 82 Shingle House Road is a distinctive Millwood estate for the buyer who values land, privacy and potential over cookie-cutter perfection. Originally dating to 1762, the property has evolved over time and offers a unique combination of old-world charm, generous space and exceptional flexibility. The main residence features spacious living areas, a large chef’s kitchen, fireplaces, beautiful natural light and peaceful views of the grounds. While the home offers great bones and many modern day appealing features, it is ready for the next owner to bring vision, updates and restoration to make it truly their own. Set on approximately 6.97 acres, the grounds are what make this offering so special: a private pond, mature trees, landscaped stonework, concrete pool, hot tub, cabana, open lawns, wooded surroundings and an extraordinary sense of seclusion. Additional improvements include a detached guest cottage situated above a three-car garage, plus a second three-car garage with a private pine-paneled retreat and a private meditation space with a stone fireplace, offering endless possibilities for guests, extended family, office, creative or recreational use. This is a property for someone who wants more than a house. It is for the buyer who wants a setting, a lifestyle and the chance to restore and personalize a truly special estate in one of Westchester’s most sought-after school districts. Rare, private and impossible to duplicate, 82 Shingle House Road is ready for its next chapter.

82 Shingle House Road, Millwood

Start Your Search

Prev
1
...
8
9
10
...
14
of 14
Next

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

How much is your home worth?

How much is your home worth?

Tierra Stanback