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

$760,000

3 Beds ⋅ 2 Baths ⋅ 1020721 MLS

Set in the heart of Yorktown Heights, this exceptional home offers a sophisticated blend of classic charm and resort style living. This meticulously maintained residence sits on .55 lush acres, boasting timeless curb appeal with its Belgium block-lined driveway featuring a custom center medallion, stone entrance walls and flowering garden borders. The interior features a thoughtfully designed layout where natural light dances across gleaming hardwood floors. The open-concept kitchen and dining area showcase granite finishes and stainless-steel appliances, flowing seamlessly into the elegant living room. Sliding doors from the dining area lead to a side patio with a built-in grilling area, perfect for effortless indoor-outdoor entertaining. The upper level includes three well-proportioned bedrooms and a beautifully appointed hall bath with tumbled marble accents. The lower level extends the living space with a versatile recreation room, bar area, dedicated desk space, powder room, and laundry/utility room. This level also offers direct backyard access, while abundant storage throughout the home, along with a large attic space, provides exceptional organization and flexibility. The property truly transforms into a private oasis in the fully fenced backyard. Designed for relaxation and entertaining, this outdoor retreat features a patio with a fire pit and an above-ground pool with a dedicated deck. A winding garden path leads to a secluded seating area, all set against a lush, park-like backdrop. Conveniently located near the North County Trailway, FDR State Park, golf courses, parks, Trader Joe's, Uncle Giuseppe's Marketplace, dining, and major commuting routes, this home offers a rare opportunity to enjoy a vacation-like lifestyle in Yorktown Heights.

688 Pleasantview Court, Yorktown Heights

$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

$1,525,000

4 Beds ⋅ 4 Baths ⋅ 1022482 MLS

A Historic Farmhouse Estate on 8+ Acres in North Salem, NY - backing up to the Audubon property! Easy access to the Purdy's & Croton Falls train stations to NYC. Resort-like estate offering a 50-foot in-ground pool & pool house surrounded by nature to enjoy summer days! This antique farmhouse dates back to the late 1700s featuring two original fieldstone wood-burning fireplaces offering a rare balance of historic soul and modern comfort. Thoughtfully expanded in the mid-2000s, the home weaves original craftsmanship offering high ceilings throughout, spacious rooms, reclaimed chestnut hardwood floors & exposed beams together with high-end upgrades including marble bathrooms, commercial-grade appliances, cedar shingle siding, and copper gutters. Formal rooms offering a setting for entertaining and gathering. The gourmet kitchen is a showstopper: pine shiplap ceilings, custom pine cabinetry, Carrara marble countertops, a butcher block island, and a farmhouse sink, all outfitted with Wolf and Sub-Zero appliances. Cooks will appreciate the three ovens (two gas, one electric), a 4-burner gas cooktop with center griddle, and a pot filler above the range. The main-floor layout includes first-floor dedicated office/den and a second-floor loft ideal for both work & downtime. Guest room with large closet space perfect for hosting. The primary suite offers en-suite bath with Carrara marble finishes, a whirlpool soaking tub, a steam shower, and a rain shower. Upper level: two overly spacious bedrooms with vaulted pine shiplap ceilings share a generous common flex and recreation room and a full bath featuring double sinks and a classic clawfoot tub - vintage character with everyday comfort. Equestrian buyers will love the proximity to Stony Creek Horse Farm (full-time boarding, lessons, and full facilities) and Old Salem Farm, a 120-acre training and boarding facility with 66 permanent stalls. Local favorites Harvest Moon Farm & Orchard and Outhouse Orchards are just a short drive away. Zoned for the highly regarded North Salem School District. Separate barn featuring 3 car garage a loft area and sweeping views which can be finished as usable space. A rare opportunity to own a piece of history — beautifully preserved, thoughtfully expanded, and ready for its next chapter.

209 Hardscrabble Road, North Salem

$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

$2,647,600

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

$899,000

4 Beds ⋅ 2 Baths ⋅ 1021929 MLS

Discover incredible space and rare features in this unique property. This home offers 4 bedrooms and 2 bathrooms (3 bdrms/1 bathrm upstairs and 1 bedroom/1 bathrm downstairs in the in-law suite), making it perfect for multi-generational living, guests, or a private home office. Situated on an oversized lot that stands out for the neighborhood, the outdoor space is built for entertainment. Enjoy hot summer days by your private, inground pool, or relax under the large covered eating area right next to the water. The property also features a attached 2-car garage and an expansive driveway with parking for multiple vehicles or recreational equipment.Bring your toolbox and your design ideas to maximize this property's true value. With its unmatched footprint, functional layout, and premier outdoor amenities, this home is a diamond in the rough waiting for the right buyer to unlock its full potential. Sold as-is.

30 Dalewood Drive, Hartsdale

$1,450,000

6 Beds ⋅ 5 Baths ⋅ 1020887 MLS

Welcome to 12 Mount Airy Road East, an exceptionally well maintained 6-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

$1,750,000

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

$3,150,000

4 Beds ⋅ 3 Baths ⋅ 1019643 MLS

A rare offering in the heart of Bedford horse country, this exceptional country estate is set on five idyllic, level acres with direct access to the coveted BRLA riding trails. Quiet, private, and surrounded by nature, the property offers an extraordinary sense of peace where sweeping lawns, mature specimen trees, handcrafted stone walls, and timeless landscaping create a setting of remarkable beauty. Beautifully renovated and rich in character, the residence blends historic charm with modern luxury. Reclaimed wood beams, custom millwork, and an antique fireplace anchor the dramatic great room, while four fireplaces throughout the home add warmth and timeless elegance. Thoughtfully renovated in 2008, with a stunning kitchen, mudroom, and butler's pantry completed in 2021, every space has been designed with exceptional craftsmanship and comfort in mind. Radiant heated floors in the mudroom and the spa-inspired primary bath provide an added touch of everyday luxury. The main residence offers four bedrooms and three full baths, including a serene primary suite overlooking the rolling grounds. The home is served by a five-bedroom septic system, offering flexibility for future needs and stand by generator. Designed for effortless indoor-outdoor living, the estate features a heated saltwater gunite pool and spa (2021), expansive stone terraces, a fire pit for gathering beneath the stars, and a charming fenced garden perfect for flowers, herbs, or seasonal vegetables—capturing the essence of refined country living. A separate carriage house offers exceptional versatility with a private one-bedroom guest residence complete with a full kitchen, full bath, laundry, private deck, and its own dedicated septic system—ideal for guests, extended family, an au pair, or a home office. It's 880 square feet and included in total square footage. The approach is as memorable as the home itself. A circular gravel driveway, highlighted by a picturesque wishing well, welcomes guests to the estate. A detached two-car garage with custom mahogany doors is complemented by covered parking for two additional vehicles, providing ample space while enhancing the property's timeless country appeal. More than a home, 28 Bayberry Lane is a private retreat where timeless craftsmanship, luxurious amenities, equestrian access, and the quiet beauty of Bedford come together in one truly distinctive offering. Rarely does a property so effortlessly combine character, privacy, and modern comfort in one of Westchester's most coveted locations.

28 Bayberry Lane, Bedford Corners

$4,500,000

6 Beds ⋅ 7 Baths ⋅ 1020629 MLS

Breathtaking views of the Hudson River and the Tappan Zee Bridge define this hilltop home set on a private cul-de-sac. Expansive windows frame the landscape from nearly every room, filling the home with natural light, while covered decks extend the living space outdoors for year-round enjoyment. Completely rebuilt in 2015 by a local award winning architect, the home was designed with both function and style in mind. The sleek, contemporary architecture is complemented by an open, loft-like floor plan with radiant heat and Italian oak flooring throughout. A spacious home office, a well-appointed primary suite and a professional gym add to the luxury and livability of this sprawling residence. The first floor centers around a chef's kitchen with stainless steel appliances, custom Leicht cabinetry, walk-in pantry and a large quartzite center island that naturally serves as the gathering place for everyday living and entertaining. The second floor offers four large bedrooms all with en-suite bathrooms and a convenient laundry room. A private first-floor bedroom or office, tucked off the informal entrance, provides flexibility for guests or working from home. The lower level includes an additional guest bedroom with a full bath and laundry center. A professional gym with doors opening to the yard was added in 2026. An elevator provides easy access to all three levels. The outdoor spaces are equally impressive, featuring a heated saltwater pool surrounded by professionally landscaped grounds that offer both privacy and a beautiful natural setting. Throughout the home, high-quality and energy efficient features include radiant heated floors, an aluminum standing-seam roof, spray foam insulation, a Lutron smart home system, integrated indoor and outdoor ceiling speakers, elevator and a three-car garage. Just 30 miles from Midtown Manhattan, this exceptional property combines contemporary design, modern (smart) amenities, and sweeping river views in one of the Rivertowns' most desirable locations. Irvington is an historic and picturesque village with acres of greenspace and miles of trails. The Main street is dotted with destination restaurants and shops that lead down to the train station and waterfront, with ever present views of the Hudson.

4 Riverview Court, Irvington

Start Your Search

Prev
1
...
5
6
7
...
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.