Homes for Sale with a Pool in Westchester, NY

Opportunities like this don’t come along often! If you’ve been looking to make Yorktown Heights home and want the highly sought-after Yorktown Heights School District, look no further. Set on a private dead-end street and situated on over 1.2 beautifully landscaped acres, this lovingly maintained Colonial offers the perfect combination of space, privacy, functionality, and location. With over 2,500 square feet of above-grade living space, the home features 4 bedrooms, 3 bathrooms, a 2-car attached garage, and an additional 575+ square feet of finished walk-out lower-level space, bringing the total finished area to over 3,000 square feet. The impressive grounds are truly a standout. Level, expansive, and meticulously manicured, the property is surrounded by mature trees, established plantings, colorful flowers, and lush landscaping. At the center of it all is an impressive 24' x 52' above-ground pool, creating a private backyard retreat that feels more like a resort than home. Step inside and you’re immediately welcomed by an open, inviting layout with excellent flow and hardwood flooring throughout the main level. The spacious living areas are designed for both everyday living and entertaining. A formal dining area features a charming bay window and chandelier, while the expansive living room showcases a wall of windows and the family room features a dual-sided wood-burning fireplace with a striking brick accent wall and built-in wood storage. The eat-in kitchen offers excellent functionality and boasts sliders leading directly to the expansive patio and backyard—perfect for summer entertaining, pool days, and outdoor dining. The updated kitchen offers functionality and a great flow for prepping, cooking and entertaining. A convenient powder room completes the main level. Upstairs, the spacious primary suite features an en-suite bath with shower, accompanied by three additional bedrooms and a full hallway bathroom with tub. The walk-out lower level adds an entirely new dimension to the home. Designed for entertaining and recreation, this finished space features an incredible bar/pub with custom built-ins, shelving, and benches, along with a dedicated TV area, game area, and an accent fireplace with custom mantle and feature wall. The lower level also includes a laundry area, summer kitchen, mechanical room, and abundant storage. And then there’s the location! Enjoy easy access to major shopping, restaurants, bars, coffee shops, parks, hiking trails, golf courses, major roadways, and highways. The home is also conveniently located close to schools and daycare centers, making everyday living exceptionally convenient. With its private setting, expansive property, resort-style backyard, versatile living spaces, and prime Yorktown Heights location, this is a home you won’t want to miss. Come see for yourself—opportunities like this don’t last!

476 Hilltop Road, Yorktown Heights

$2,200,000

6 Beds ⋅ 5 Baths ⋅ 1004898 MLS

Set within the beautiful grounds of Knollwood Country Club, 34 Hevelyn Road is a captivating 1928 Tudor that beautifully blends timeless character and charm with thoughtfully updated interiors and an impressive array of modern amenities. From the street, the home makes a memorable first impression with exceptional curb appeal, an expansive front lawn, and a picturesque setting that provides a wonderful sense of privacy and presence. The location is equally appealing, with easy access to New York City, Metro-North trains, major highways, restaurants, shopping, and everyday conveniences. Inside, original architectural details are complemented by sophisticated, inviting spaces designed for comfortable living and entertaining. The main level features a welcoming foyer, spacious family room with wide-plank hardwood floors, recessed lighting, elegant sconces, and a wood-burning fireplace with distinctive wood mantle. French doors open to the outdoor spaces, while a charming sunroom with flagstone flooring provides a peaceful retreat. The sophisticated library/office offers hardwood floors, custom built-ins and bookshelves, recessed lighting, and a gas fireplace with marble surround. At the heart of the home is a stunning chef’s kitchen featuring two skylights, exposed wood beams, white quartz countertops, subway tile, glass-front cabinetry, extensive custom storage, and a large center island with breakfast bar. A walk-in pantry and second pantry with pull-out shelving provide exceptional storage. Premium appliances include an extra-wide Thermador refrigerator and Wolf six-burner gas range with double ovens. The adjoining dining room features hardwood floors, elegant sconces, and French doors opening directly to the covered patio for seamless indoor-outdoor entertaining. Upstairs, the spacious primary suite offers hardwood floors, custom shades, a custom walk-in closet, and a luxurious bath with spacious walk-in shower, freestanding soaking tub, and radiant heated floors. Three additional bedrooms provide generous accommodations, including an ensuite bedroom with updated private bath and another bedroom with access to a beautifully renovated adjoining bath. Two versatile bonus rooms offer flexibility for offices, a gym, sitting rooms, playrooms, or guest spaces. A separate hall bath and generous linen storage complete the level. The fully floored walk-up attic includes a cedar closet and additional storage. The home also offers an expansive lower level providing approximately 1,400 square feet of additional space currently designated for storage. The expansive, level backyard is one of the home’s most compelling features, offering exceptional space for entertaining, recreation, gardening, or simply enjoying the privacy of the setting. A heated Gunite pool, creates a resort-like destination just outside the home. The covered patio is ideal for outdoor dining and lounging, while the generous lawn provides plenty of room for gatherings and play. A separate shed offers convenient storage. Additional highlights include a heated two-car attached garage with custom cubbies, shoe rack, built-in shelving and drain; plaster walls; ten-zone heating; invisible dog fence, and an advanced AI-based security system with 24/7 surveillance, cameras, and motion sensors. Additional inclusions include an EV charger, whole house generator, second refrigerator, window treatments and draperies, TVs and brackets, light fixtures, and movie/projector equipment, all offered as-is. With its distinctive Tudor architecture, exceptional curb appeal, expansive grounds, Knollwood Country Club setting, and remarkable indoor and outdoor amenities, 34 Hevelyn Road offers a rare combination of character, lifestyle, convenience, and privacy.

34 Hevelyne Road, Elmsford

$2,395,000

6 Beds ⋅ 4 Baths ⋅ 1057736 MLS

A rare offering in the coveted Edgemont School District, this 5,500-square-foot home offers a private resort-style oasis on a meticulously landscaped, park-like acre. Expanded in 1995 with inspiration from Frank Lloyd Wright, the home combines distinctive architectural charm with a versatile layout for everyday living and entertaining. A sweeping circular driveway leads to the grand entrance, framed by tranquil koi ponds that create a striking welcome! Inviting interiors connect seamlessly to a fully fenced backyard designed for relaxation, play, and entertaining. An elegant living room with a fireplace, a family room with soaring ceilings, and a formal dining room offer generous gathering spaces, while the chef’s kitchen features premium JennAir appliances and French doors to the patio. Enjoy an in-ground pool, multiple patios, a man-made beach, an expansive lawn, and a custom treehouse with an elevated viewing deck. French doors from the kitchen, family room, and primary suite make indoor-outdoor living effortless. The primary suite with an ensuite bath features dramatic ceiling heights, creating a serene, luxurious retreat with direct access to the patio and pool. A flexible floor plan accommodates multigenerational living, an au pair or in-law arrangement, guests, or private work-from-home spaces. Additional highlights include a playroom, an oversized garage and additional garage/storage space designed to accommodate up to four vehicles, a private gated courtyard, and abundant guest parking. Fully owned solar panels are included with the home at no additional cost, providing ongoing electricity savings. The convenient location is a commuter’s delight, with easy access to Manhattan by train (30 mins), car, or bus, as well as shopping, restaurants, and the charm of nearby Scarsdale Village.

46 Sprain Valley Road, Scarsdale

$4,900,000

5 Beds ⋅ 8 Baths ⋅ 1054426 MLS

Haines House is a rare modern retreat where architecture, landscape and natural light are composed as one. Set on nearly six private acres in Bedford Corners, just 38 miles from Manhattan’s Upper West Side, the property comprises a main residence and Cottage Pavilions, with separate drives for formal and courtyard parking. Bedford Hills Metro-North station, with direct service to Grand Central, is five minutes away. Frank Dushin’s midcentury integration of architecture and landscape evokes the harmony of postmodern Japanese design. Completely adapted and rebuilt for the 21st century, it offers space for entertainment, creative work and quiet escape. The two residences total over 7,000 square feet. Stone, cedar and glass follow the contours of the land, while wood, bluestone, custom lighting and sculptural details meet an all-white palette in a timeless, organic aesthetic. The main residence opens into an expansive reception hall with soaring 14-foot ceilings and a fireplace. Wide bluestone staircases and a glass-enclosed elevator with exterior views connect all three floors. On the second floor, the living level unites the kitchen, dining area and fireside living room for living and entertaining. Extensive windows draw the landscape indoors, while cathedral ceilings add scale. Double doors open to a covered balcony for dining and lounging above the pool and gardens. A private guest wing offers two-bedroom suites, each with an en-suite bath featuring a tub and walk-in shower, plus direct access to the patio and an inground saltwater swimming pool. The uppermost level is a 1,700-square-foot primary bedroom retreat, reached by elevator or bluestone stairs. A closet-lined walkway leads to a spacious bedroom. A separate sitting room with fireplace, two bathrooms, a dressing room or office, and private terraces complete this secluded level. The Cottage Pavilions offer space for guests, creative pursuits or home offices. They include two bedrooms, two bathrooms, an additional room, a fully equipped kitchen and dining area, and a sunken den with fireplace and a ceiling over 20 feet. A luminous glass gallery connects the 2 separate wings, framing garden views and serving as a contemporary orangery or greenhouse. Japanese-inspired gardens, terraced lawns and walkways integrate with natural boulder and rock formations, while stone sculptures add a sense of place and history. A wood pergola encloses an inner garden around the residences, bordering an outer garden maintained as wildlife habitat. A heart-shaped natural pond collects surface water through landscaped canals and underground drainage, managing roof and surface rainwater without conventional gutters. Open lawns create distinct destinations, while broad, level terraces accommodate outdoor dining, entertaining and recreation. A 60-foot heated and cooled saltwater lap pool is integrated into the terrain and surrounded by expansive decks. A sports court for tennis and basketball occupies a secluded, shaded valley garden. Durable materials considered landscaping and integrated infrastructure support a low-maintenance design. Systems include hydronic radiant heating beneath bluestone and wood floors, three autonomous climate-control systems, high-velocity heat-pump heating and cooling, and 400-amp electrical service. Underfloor electric heating adds comfort in bathrooms and other areas. Automated gates and integrated fire, security and camera systems enhance privacy and security. Two interior garage bays have underfloor heating, including a drive-through bay, with additional parking at the main residence, Cottage Pavilions and guest entrance. Private, versatile and exceptionally rare, Haines House offers a destination retreat near Bedford Village and Manhattan, with the comfort of a private compound and flexibility of a creative workspace.

496 Haines Road, Bedford Corners

$859,900

3 Beds ⋅ 3 Baths ⋅ 1057660 MLS

Welcome to exceptional indoor and outdoor living. Set on a private 1.5 acres and surrounded by mature trees, this home features incredible outdoor spaces ideal for entertaining or relaxing in total privacy. This custom home offers an impressive stone facade set in granite and stone column entry is set privately and situated on 1.5 acres in an ideal Southern Yorktown location with Yorktown schools. Step inside this home and feel how open and light-filled the entire main living level with sun drenched rooms, windows galore and distant views. Let the sunshine in on the recently refinished hardwood floors, the open floor plan is flexible and smartly designed with spaces for dining, open living room and a stunning kitchen designed for the serious cook with side and rear decks to enjoy the outdoors those distant views. The kitchen has storage galore with a pantry closet and custom cabinetry, professional-grade oven/range and finished with granite tops with large center island. Whether for daily needs or special occasions, this kitchen will perform quite capably, and the cook will appreciate the beautiful views. This home offers a remarkable amount of indoor-outdoor flow, including access to a rear deck and a side deck off the kitchen, just a perfect spot to enjoy your morning coffee. The owner's suite has ample space and includes an on-suite bath. The finished lower level provides a family room, home office or guest room with a summer kitchen and full bath. It’s the perfect setup for guests or the extended family. 986 Cliff Avenue is an ideal residence for the buyer seeking a thoughtfully designed house offering privacy, home office and recreation spaces, including an impressive stone saltwater pool with waterfall. Set in an ideal location and just a few minutes to town shopping, restaurants, access to the county bike trail and close proximity to schools, hiking trails, town parks and parkway.

986 Cliff Avenue, Yorktown Heights

$2,495,000

5 Beds ⋅ 5 Baths ⋅ 1052711 MLS

A distinguished 1922 Center Hall Stone Colonial set on .77 acres of beautifully landscaped private grounds, offering 5 bedrooms, 4 full baths, 1 powder room, and an extraordinary collection of indoor and outdoor amenities. An expansive circular driveway accented with Belgian block creates an impressive approach to this gracious home, where timeless architecture is complemented by thoughtful updates for modern living. A custom granite entry foyer welcomes you into generously proportioned interiors rich with architectural character, including five working fireplaces. The eat-in kitchen is designed for serious cooking and entertaining, featuring Sub-Zero refrigeration, a new 2026 Dacor stovetop, Wolf double ovens, and granite countertops. The expansive primary suite is a private retreat featuring a luxurious bath, generous walk-in closet with washer and dryer hookups, and adjoining study. Both the primary bath and study provide direct access to a private terrace, creating a wonderful indoor-outdoor sanctuary. Beyond the stated living square footage, the home offers approximately 1,300 additional sq. ft. of above-ground lower-level space with a walkout directly to the backyard. Designed for recreation, wellness, and entertaining, this exceptional level features a new dry sauna, wet bar, fireplace, bathroom, laundry room, wine cooler, refrigerator, and dehumidifier. The professionally landscaped grounds are among the property's defining features, thoughtfully designed with an impressive collection of specimen trees, mature plantings, and ornamental shrubs that create a lush and private setting. At the heart of the outdoor space is a heated Gunite and Diamond Brite pool with spillover spa, complemented by a 272 sq. ft. pool house. A remarkable 432 sq. ft. renovated antique greenhouse with its own gas fireplace provides an enchanting additional space for entertaining, gardening, relaxing, or creative pursuits. The grounds offer even more opportunities for recreation with a professionally installed basketball hoop and swing set, while the expansive circular driveway provides generous additional parking. Significant improvements enhance the home's comfort and functionality. All windows were replaced in 2021. Additional upgrades include five zones of central air installed approximately six years ago, a new Burnham furnace and water heater (2025), upgraded 200-amp electrical service, replacement of the water main to the street, an electric-vehicle charging station, and a 2-car attached garage. With its classic stone architecture, gracious proportions, beautifully designed grounds, exceptional entertaining spaces, and extensive updates, this is a rare opportunity to enjoy the character of a 1922 Center Hall Colonial with amenities thoughtfully suited to today's lifestyle.

209 Beechmont Drive, New Rochelle

$2,995,000

5 Beds ⋅ 7 Baths ⋅ 1055687 MLS

Set on one of Armonk's most esteemed streets, 37 Sarles Street offers a rare opportunity to own an exclusive 2.98-acre estate. Unmatched privacy and a serene natural backdrop, protected for generations to come, make this an ideal place to raise. From the moment you arrive, the home makes an impression. A sweeping driveway leads to a four-car garage, pairing convenience with grandeur. Inside, soaring cathedral ceilings crown the family room, where designer stonework creates a dramatic focal point letting your imagination run wild with your decor. Natural light fills the space, blending elegance with warmth for both quiet evenings and lively gatherings. This home was designed for entertaining. The resort-style backyard features a sparkling saltwater pool, lush professional landscaping, a covered patio that lives like a full outdoor living room, and a sunset-facing hot tub. Whether you're hosting a summer soir or stargazing with the kids, the space is a true extension of the home's luxury lifestyle. Your guests won't want to leave.

37 Sarles Street, Armonk

$799,995

3 Beds ⋅ 3 Baths ⋅ 1052161 MLS

Welcome HOME to 518 Manchester! Lovingly maintained by the same owners for nearly 40 years, this expanded raised ranch offers an impressive amount of living space and has been thoughtfully cared for and updated throughout. The main level features beautiful hardwood floors, a spacious sun-filled living room, dining area, three bedrooms and two full baths. The oversized primary bedroom features its own private bath and large walk-in closet. The updated kitchen offers Wellborn cabinetry, granite countertops, stainless steel appliances and a gas range with convection oven. The fully finished lower level adds tremendous versatility with a large family room featuring a brick fireplace, additional recreation or living space, a full bath, kitchenette area and laundry. With a separate rear entrance and two staircases connecting the levels, the layout offers plenty of possibilities for guests, a home office or extended family. Additional features include Andersen windows, three heating zones, central air on the main level, an annually serviced boiler, newer roof, Wi-Fi enabled garage door openers and an oversized two-car garage. Outside is just as impressive, with beautifully maintained grounds, a spacious backyard, above-ground pool, deck and lower patio area perfect for relaxing or entertaining. Set back from the road and surrounded by mature landscaping, this spacious home offers plenty of privacy, a fenced-in yard, and a wonderful opportunity to own a property that has been lovingly cared for by the same owners for decades. Conveniently located near shopping, golf, dining, and popular local nightlife.

518 Manchester Road, Yorktown Heights

$1,975,000

5 Beds ⋅ 6 Baths ⋅ 1055829 MLS

Welcome to 68 Stonewall Circle, a sunny custom-built Colonial with a southern back yard exposure in Park Lane. A stone wall lends character to the front and back yard while mature landscaping creates privacy around the spacious rear patio and backyard. the back yard is fully fenced. Five flowering pear trees and two flowering cherry trees flank the driveway. Two flowering crab apples tress show off their glory both front an back. The first floor offers a great room with a fireplace, and marble surround ,a large custom kitchen with quartzite counters and backsplash and breakfast area opening to an Indiana limestone patio overlooking the grounds,. There is generous formal dining room., library/ office, first floor bedroom /playroom and walk in closet, and bath. powder room, laundry room, and two-car heated garage completes the level. Full finished basement, store room , cedar closet, wine closet, office, bath sliding door to the outside. C of O has been applied for . Upstairs, the spacious primary suite with tray ceilings features a double bathroom with a Jacuzzi tub an three large walk in closets. Another bedroom has an en-suite bath, and two additional bedrooms share a Jack-and-Jill bath. Ample closets provide storage throughout the home. The finished lower level opens to the sunny outdoors and offers room for play, ping-pong, and gatherings, along with built-in closets, workout room and bath, and a separate large storage room. cedar closet, and wine closet. House has a full house water filtration system,.ad well as a filtration system in the kitchen island. 3 Zone ac and heat. Primary bedroom is on one zone, rest of upstairs is on second zone, 3rd zone services the first floor. Basement has its own zone. Outdoor sprinklers, whole house is equipped with interior fire sprinklers. Garage is heated and driveway is fully paved wth stone pavers. The home is equipped with lighting rods and a Radon Mitigation System. There is a central vacuum System.

68 Stonewall Circle, West Harrison

$1,595,000

4 Beds ⋅ 3 Baths ⋅ 1046921 MLS

Offered for the first time by its original owners, this immaculate 4-bedroom Bedford Village contemporary sits on 4 picturesque acres along a sought-after country road, just minutes from town. Lovingly maintained throughout, the house has all hardwood floors, a new AC system, new windows, a rebuilt double tiered deck, a new steam washer/dryer, an epoxy finished garage floor and is freshly painted inside and out. The property is totally private and is centered around a free-form heated saltwater pool that blends seamlessly into the landscape. This home is streaming with natural light and the sunroom is simply magical. The kitchen includes a Subzero refrigerator and a high-end Advantium oven. The basement adds extra space (not included in the square footage) for theater, playroom or gym and also has a 1000 bottle, temperature controlled wine cellar.

76 Pine Brook Road, Bedford

$2,300,000

3 Beds ⋅ 4 Baths ⋅ 1055936 MLS

To-be-built custom home offering modern design, thoughtful layout, and exceptional living space. This spacious residence features an open-concept floor plan with a dramatic two-story living room, gourmet kitchen with pantry, and seamless flow to the rear porch perfect for indoor/outdoor entertaining. The main level includes a desirable first-floor primary bedroom suite with walk-in closet and private bath, plus formal dining room and welcoming foyer. The second level offers additional generously sized bedrooms, multiple baths, and open views to the living area below, creating a bright and airy feel throughout. Designed with today's lifestyle in mind, this home combines comfort, functionally, and timeless curb appeal. Conveniently located near shopping, dining, major highways and local amenities. Buyer may have opportunity to customize finishes. Photos have been virtually generated.

2 Hageman Court, Katonah

$3,088,000

7 Beds ⋅ 7 Baths ⋅ 1055737 MLS

Welcome to The Roaring Brook Estate, a rare Chappaqua retreat set on more than seven private acres of natural beauty, architectural significance, and quiet history. Just about one hour north of Manhattan, this distinctive property offers a remarkable combination of privacy, land, design, and lifestyle. Originally built in 1958, the residence is known in architectural records as the Donald Miller Jr. House, Now the Roaring Brook Estate, and was designed by celebrated American modernist architect Edward Larrabee Barnes. The home was featured in Architectural Record Houses of 1959, with USModernist identifying the original project team as including structural engineer William Atlas, builder O’Brien and Kinkle, landscape designers Bye and Herrmann, and interiors by Mary Barnes and Emily Malino. The architecture reflects Barnes’s modernist philosophy: clean lines, openness, natural light, and a close relationship between the residence and the surrounding landscape. Glass, structure, and proportion work together to frame the outdoors rather than compete with it, creating a home that feels deeply connected to its setting. Surrounded by mature trees, open lawns, a peaceful brook, and beautiful natural scenery, the estate creates an immediate sense of calm and escape. The property unfolds through light, landscape, and privacy — morning sun through the trees, quiet afternoons across the grounds, and peaceful evenings surrounded by nature. Here, the land is not simply a backdrop; it is part of the living experience. In addition to the main residence, the property also includes a separate guest house featuring a beautiful studio space, currently occupied by a tenant. This added structure enhances the estate’s flexibility and creates potential for guest accommodations, creative use, private work space, or income-producing use, subject to applicable lease terms and local requirements. This is a unique opportunity for the next owner to enjoy, restore, or reimagine a significant modernist estate with character, history, and long-term lifestyle potential. Whether used as a full-time residence, weekend retreat, creative sanctuary, or private gathering place, 301 Roaring Brook Road offers the space, privacy, and atmosphere that are increasingly difficult to find in Westchester. Located in desirable Chappaqua, the property is close to village conveniences, Metro-North, parks, trails, and the highly regarded Chappaqua school district. More than a home, The Roaring Brook Estate is a setting, a story, and a rare opportunity to become the next steward of one of Chappaqua’s most memorable properties.

301 Roaring Brook Road, Chappaqua

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

Tierra Stanback