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

$2,425,000

5 Beds ⋅ 6 Baths ⋅ 969675 MLS

Some properties simply cannot be recreated. They are collected over centuries. Layer by layer. Story by story. Stone by stone. Set behind towering trees and abutting hundreds of protected acres of the Mianus River Gorge Preserve, this exceptional Bedford estate offers a rare opportunity to own a thoughtfully restored historic property surrounded by natural beauty and privacy. Dating back to 1825, the historic main residence was once part of a larger Long Ridge Road estate and formerly operated as the Wilkenloh Hotel in the early 19th century. Today, the home has been tastefully renovated and refreshed, blending timeless architectural character with modern comfort and functionality. As you enter through two dramatic stone entry boulders, a winding gravel driveway leads to the main residence, separate cottage and expansive grounds featuring rolling lawns, mature trees and historic stone walls. Set on over 5.5 acres, the property offers a peaceful setting with scenic landscape views in every season. Inside the main residence, original wide plank floors, a natural stone fireplace and gracious living spaces showcase craftsmanship rarely found today. Walls of windows and glass doors fill the home with natural light while framing picturesque views of the surrounding property. The open-concept kitchen, dining and family room create an ideal layout for everyday living and entertaining. A covered rocking-chair porch supported by stately pillars overlooks the property and provides a tranquil setting to enjoy the changing seasons of Bedford. Outdoor amenities include a restored 22x44 heated gunite pool with updated mechanicals and an expansive 1,400+ square foot pool house featuring wraparound decking, outdoor fireplace, screened-in entertaining area with fireplace, wet bar, ice machine, full bath, kitchenette and flexible guest or recreation space. The separate cottage offers its own private driveway entrance and features cathedral ceilings, a palladium window, kitchen, full bath, garage, additional flexible-use rooms and extensive storage space, ideal for guests, home office use, or extended living arrangements. Additional highlights include bluestone patios, restored landscape features and a private three-acre trail system suitable for walking, jogging, mountain biking and outdoor recreation. Conveniently located near Bedford, major roadways, shopping, dining and Metro North train access, this unique Westchester County property offers a rare combination of historic character, updated amenities, flexible living space and exceptional natural surroundings. square footage consitst of: 4017sqft of total living space includes 5 bedrooms, 3.5 baths, cottage (independent assessor 834sqft attached documents) includes kitchen, bath, 2 rooms with garage below and separate driveway entrance. Pool house, 2 car garage below, heat pump air, playroom, bath, kitchenette, 3/4 wrap-around deck overlooking pool, screened in stone patio with fireplace (1469 sqft

233 Long Ridge Road, Bedford

$1,800,000

5 Beds ⋅ 6 Baths ⋅ 994571 MLS

"VILLA KEEN" - THE GLAMOUR OF A CASTLE MEETS BROADWAY & THE ARTS - Irvington, NY, Circa 1929. Just imagine... Joseph Keen & his wife break ground to build a "Cinderella" castle on a breathtaking 2.43 acre parcel of land, a stone's throw to Halsey Pond, minutes to the Hudson River and a short 30 minute trip from Manhattan. Coming home, meandering through the stately stone pillar entry, the Beech Tree with historic Indian carvings in front of the sweeping stairs tells a story from the 1700's, but that we will save for a rainy day... Fast forward, Lloyd Stratton, president of the Associated Press takes residency, tirelessly typing from the oak library. In the 1960's enters resident Robert Wright, producer of the Carol Burnett Show & other Broadway staples. If you are seeking inspiration beyond your wildest dreams, everything is still in tact today, including the Chesney fireplace mantle, Mackenzie-Childs fixtures and the Schonbek Austrian crystal chandelier... If you are looking to entertain, be our guest, whether you enter through the 15' stained glass gates to your private courtyard, spend your time in the grand dining room suitable for Beauty & the Beast, the Green Room, relaxing poolside, or in the pool house, the choice is yours. Of course your guests or residents will cherish their stay in the turret bedrooms with ornate stained glass windows, or in the private guest quarters with separate entry... Speaking of entertainment, the list of distinguished guests and residents goes on, like Academy award-winning actress Shirley Jones, Tony Award-winning actor Jack Cassidy and their son, multi-platinum recording artist Shaun Cassidy. If only these walls could talk... Well, you may still hear the grand piano resonating in the formal living room by one of the many roaring fires... A perfectly sound structure on a dead end private street, with newer systems & mechanics, a train line to NYC just 5 minutes away and award-winning Irvington Schools, here is your chance to enhance a property that can never be duplicated today. In fact, "Villa Keen" is so special, a replica only exists in California by one of its former owners. Are you ready to live this fairytale fantasy?

16 Lewis Road, Irvington

$1,330,000

5 Beds ⋅ 4 Baths ⋅ 995205 MLS

This stately Mediterranean villa near Bronxville is set high on a private, lushly landscaped large corner property. The flagstone walkway leads to a refined entry door with brass lion-head knocker and into the grand foyer featuring a sweeping curved staircase with distinctive balustrades. Classic center hall layout with all oversized rooms is perfect for entertaining and relaxing. Two sets of leaded-glass double French doors open to the ballroom-sized living room and elegant dining room, both with intricate moldings, gleaming hardwood maple floors and custom fireplace. All walls and ceilings are hand-crafted Venetian plaster. Sun-drenched wood paneled home office or first floor bedroom has new bay window and built-ins. A bath with gold fixtures is also on the first floor. The updated kitchen and butler’s pantry have stunning granite counters, designer backsplash, a custom 40" gas range with six burners, double oven and oversized range hood, breakfast nook and mud room with many closets. Amenities include a lower level in-law apartment with full bath, separate access and expansion possibilities. Upstairs, the huge ensuite primary bedroom has its own private 220 SF terrace, cedar closets, and enormous remodeled bath with marble floor and separate shower room. The walk-out lower level, with rec room, laundry, full bath with shower, and bedroom, accommodates au pair or in-law. The heated, two-plus car garage is below the house, with direct indoor access. Third floor has additional 1,500 SF with cathedral ceiling (not included in house square footage) with space for 6th and 7th bedroom and full bath. New 200-amp service and new electric throughout. Freshly painted, inside and out. Very private yard has fully operable in-ground gunite mini pool that provides a special outdoor oasis. Massive stone walls, terraces, patios, and full property underground sprinkler system. Ludovici red Spanish tile roof is spectacular. Some furnishings included. Short walk to Metro North. NYC commute is 25-minutes from Fleetwood or Bronxville. Shopping in Fleetwood and Bronxville. Taxes on previous listing are corrected and are before STAR deduction. MOVE-IN READY. Low cost per square foot.

130 E Cedar Street, Mount Vernon

$6,400,000

6 Beds ⋅ 5 Baths ⋅ 992131 MLS

WOLSEY FARM. One of Bedford’s most iconic estate properties—first time offered in nearly 100 years. Remarkable Colonial Estate dating to 1810. Grand main rooms with incredibly preserved period detailing. Stunning interior with graciously proportioned rooms, high ceilings, period millwork, intricate moldings and spectacular quarter-sawn oak floors with black walnut inlays. Impressive Portico supported by massive Corinthian columns. Center Entrance Hall. Living Room with fireplace and doors to covered porch for alfresco entertaining. Formal Dining Room for entertaining. Country Kitchen with breakfast area. Family Room with doors to terrace. Library and Office for working remotely. Six Bedrooms including Primary Suites. Spectacular terrace and covered porch for alfresco entertaining. Heated Pool with Spa. Over eighteen spectacular acres with incredible trees and flowering plantings in the heart of Bedford. Gate House with fireplace-the ideal artists’s or writer’s studio. Two Bedroom Guest Cottage. Second “Superintendent’s” Cottage with two Bedrooms. Numerous barns and farm buildings including large Chicken Coop. Six fenced paddocks, an orchard, a spring-fed pond and open meadows. A once in a lifetime opportunity!

345 McLain Street, Bedford Hills

$650,000

4 Beds ⋅ 2 Baths ⋅ 993852 MLS

Welcome to 1790 Parmly Road, Mohegan Lake, NY—an excellent opportunity for first-time homebuyers to step into homeownership in desirable Westchester County. This inviting home offers a functional layout with abundant natural light, creating a warm and comfortable living environment. The property features a spacious yard, perfect for outdoor enjoyment, entertaining, or future enhancements. Inside, the home provides a solid foundation with the opportunity to personalize and add value over time—ideal for buyers looking to make a space their own. Conveniently located near shopping, dining, parks, and major roadways, this home combines suburban tranquility with everyday accessibility. Whether you're commuting or staying local, you'll appreciate the ease of living in this well-situated neighborhood. A great alternative to renting, this property offers the chance to build equity while enjoying the benefits of homeownership. Don’t miss this opportunity to enter the Westchester market with a home full of potential.

1790 Parmly Road, Mohegan Lake

$5,495,000

5 Beds ⋅ 7 Baths ⋅ H6291697 MLS

Luxury living at its finest. This 5-bed, 6.1-bath sanctuary nestled on a quiet, tree-lined road boasts 9,540 sq ft of living space with soaring ceilings, masterful millwork, and extensive built-ins throughout. The main floor hosts a striking two-story foyer made for entertaining, billiards/bar room, 2 offices, great room with fireplace, and an impressive chef's kitchen with adjoining butler’s pantries and sunlit breakfast room. Upstairs, the sprawling primary wing dazzles with a gas fireplace, private deck, dressing room with designated shoe closets and wall-to-wall built-ins, sitting room, and lavish en-suite. 3 additional en-suite bedrooms, plus spacious storage and laundry complete the second level. Bask in the resort-like amenities of your 2.6-acre property with its expansive bluestone patio, outdoor kitchen, in-ground pool, heated 5-car garage, and a large storage shed sized to fit 2 cars. An unfinished lower level and walk-up attic offer room to expand. An incredible opportunity!

9 Meadow Lane, Purchase

$1,545,000

4 Beds ⋅ 4 Baths ⋅ 986984 MLS

Welcome to Somers Estates, one of Somers newest subdivisions. Custom designed Farm House where value meets Luxury. Situated on 1.13 acre level lot . 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 three 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.

24 Florence Drive, Somers

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 991143 MLS

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

217 Trinity Pass, Pound Ridge

$2,350,000

4 Beds ⋅ 4 Baths ⋅ 984642 MLS

Steeped in history and timeless elegance, this exceptional circa-1800 Hiram Halle Colonial is set on four beautifully landscaped acres. Rich in period character, the home showcases signature Hiram Halle windows, hand-hewn wide-plank antique floors, distinctive pillow ceilings, and multiple wood-burning fireplaces throughout its gracious living spaces. A sun-filled living room, elegant dining room, expansive sunroom, and cherry-paneled library create an atmosphere of warmth and sophistication. The heart of the home is a chef’s kitchen featuring a large center island, custom coffee bar, gas fireplace, and inviting breakfast area with doors opening to the patios and gardens. The second level offers four spacious bedrooms, three full baths, and a dedicated laundry room, blending historic charm with modern convenience. Outside, the estate unfolds into a private retreat with a Gunite pool, mature trees, lush gardens, and exquisite plantings. A classic barn with a fireplace-enhanced upper level offers exceptional flex space with endless possibilities, such as a yoga studio, artist's studio, home office, wellness sanctuary, or gathering space! A rare offering, this remarkable property seamlessly combines historic significance, exceptional craftsmanship, and an extraordinary lifestyle setting.

516 Pound Ridge Road, Bedford

$4,125,000

5 Beds ⋅ 5 Baths ⋅ 987844 MLS

Refined and timeless, this gracious residence has been meticulously preserved and maintained for over a century. Approached by a gated, tree-lined gravel drive, the house is a distinguished example of early 20th-century Georgian architecture, offering exceptional privacy and a profound sense of tranquility. Set on over five acres in the heart of Bedford Hills, surrounded by majestic specimen trees and beautifully curated perennial gardens, the property embodies the essence of a classic country estate. Amenities include a heated pool, an enchanting guest cottage, a greenhouse, a caretaker’s residence, a detached two-car garage, and dedicated maintenance buildings. Inside, the house reflects the signature elegance and proportion associated with Delano & Aldrich; high ceilings, expansive openings between principal rooms, and refined architectural detailing create a seamless flow for both formal entertaining and relaxed living. Fireplaces anchor the generously scaled living and dining rooms, while framed-glass French doors open to a grand sunroom. This light-filled space extends to a stone terrace overlooking the gardens—ideal for summer gatherings or sunlit winter afternoons. The kitchen, complemented by an adjoining sitting room, offers an inviting setting for intimate meals and everyday living. Upstairs, the primary suite provides a serene retreat, complete with its own fireplace and a luxurious ensuite bath designed for quiet indulgence. A former sleeping porch has been thoughtfully reimagined as a charming playroom with adjoining guest quarters, accompanied by an additional spacious bedroom and hall bath. Each bedroom features its own distinctive fireplace and enjoys picturesque garden views through large casement windows. The third floor offers two substantial bedrooms, a classic bath, and a skylit artist’s studio filled with natural light, along with an adjoining atelier and generous storage. More land available.

328 McLain Street, Bedford Hills

$999,999

4 Beds ⋅ 3 Baths ⋅ 986322 MLS

Tucked away on a quiet lane in North Salem, this one-of-a-kind contemporary home offers a rare blend of privacy, design, and natural beauty. Set amidst a breathtaking perennial garden with meandering paths, the property invites you into a serene, zen-like retreat complete with a tranquil pool and hot tub. Inside the approximately 2,900 square foot residence showcases an open, airy floor plan highlighted by abundant natural light, numerous skylights, and two fireplaces that anchor the living and dining spaces. The kitchen flows seamlessly onto an inviting deck-perfect for morning coffee or effortless outdoor entertaining. The home features four bedrooms and two-and-a-half baths, including thoughtfully designed details such as Japanese toilets. An upper-level space provides flexibility for a home office or yoga room, adding to the home's versatility. The grounds are equally captivating, with cleared areas ideal for vegetable gardening-where abundant harvests have thrived. The architecture evokes a timeless, Frank Lloyd Wright inspired aesthetic, harmonizing beautifully with the surrounding landscape. Located just 55 miles north of New York City, this property offers convenient access to trains and major highways, making it ideal for both full-time living and weekend escapes. North Salem's renowned equestrian culture and expansive open spaces further enhance the appeal of this exceptional offering. A truly special and well maintained hidden gem - this home is where nature, design, and lifestyle come together in perfect balance.

213 Vail Lane, North Salem

$5,500,000

5 Beds ⋅ 8 Baths ⋅ 922795 MLS

A new build echoing the great modern masters, Haines House spans across nearly six pristine Bedford acres. While its spirit evokes the harmony often associated with Frank Lloyd Wright, its identity is rooted in the modernist vision of his contemporary, Frank Dushin. This turnkey estate includes walls of glass wrapped in warm cedar, sculptural rooflines tracing the hillside, and natural bluestone. Within the main residence, the great room opens as a sweeping expanse of glass anchored by a central fireplace. A glass enclosed elevator glides from the garage to the primary suite, reaching every level and framing the estate at each stop. The suite crowns the top floor with dual baths, a sitting room, an office, and private terraces set among the treetops. The additional bedroom suites unfold as retreats of their own. The separate guest pavilion, a light-filled structure of two suites joined by a luminous glass corridor, forms a second residence. Together the two living spaces are generous and flexible for both residents and guests, including studio spaces for creative work. Internal garages include a rare drive through bay, and there is expansive guest parking. Beyond the residences, newly relandscaped grounds unfold in broad, level gardens and lawns rolling to a tranquil pond, a shimmering saltwater pool, and a sports court. Wide open and gently sculpted, the grounds invite play, gathering, and quiet exploration alike, a private world to roam from morning to evening. Enveloped in its own green canopy, the estate offers rare privacy and security. A newly installed three zone high velocity cooling/heating system, with additional underfloor heating ensures comfort year-round. Turnkey and unique, Haines House sits minutes from Bedford Village and within easy reach of Manhattan.

496 Haines Road, Bedford Corners

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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.