Homes for Sale with a Pool in Westchester, NY

Step inside Tommy’s Lane, where understated architecture gives way to unforgettable design. From the curb, this timeless transitional Colonial sits quietly on just shy of two flat, sun-drenched private acres with a pool. Open the dramatic custom black glass front doors, however, and the entire experience changes. A dramatic two-story foyer introduces interiors that feel as though Restoration Hardware met a world-class luxury hotel. Sophisticated, glamorous, impeccably tailored, and unlike anything else on the market in South Salem. Every inch of this home has been thoughtfully reimagined with an uncompromising eye for design, craftsmanship, and quality. Everything in the home has been redone, with the owner completing an extensive top-to-bottom renovation in 2025. Rich hardwood floors flow throughout an airy, open floor plan created for both everyday living and effortless entertaining. Custom millwork, designer lighting, and bespoke finishes elevate every space, while the stunning family room is anchored by a beautiful wood-burning fireplace and a custom rich wood bar accented with elegant brass mesh detailing, functioning as both a striking focal point and a true piece of furniture. The chef’s kitchen rivals those found in substantially larger custom estates, featuring premium Sub-Zero refrigeration, a professional gas range, custom cabinetry, and dramatic two-inch-thick quartz countertops. Every selection was made with intention, resulting in a space that is as functional as it is beautiful. The principal suite is a true retreat, evoking the feeling of a boutique luxury hotel. The newly completed marble bath is extraordinary, showcasing brass fixtures, intricate mosaic marble flooring with brass inlay, a seamless glass shower, soaking tub, and refined spa-inspired finishes. A beautifully designed walk-in closet completes the suite. Three additional bedrooms complete the second floor and share a beautifully renovated hall bath finished with the same elevated, hotel-quality aesthetic found throughout the home. The lower level is designed entirely around entertaining. A spacious game room with pool table flows into a dedicated media lounge with theater seating, creating the perfect setting for movie nights or game days. A full wet bar, full bathroom, abundant natural light from windows, and direct access to the garage make this level every bit as practical as it is impressive. Outside, complete privacy surrounds the expansive backyard and large swimming pool, creating the perfect setting for summer gatherings, quiet afternoons, or evenings spent with family and friends. The property feels like a private resort while remaining exceptionally convenient. Perfectly positioned, Tommy’s Lane offers easy access to the Merritt Parkway, is approximately 10 minutes to New Canaan, 15 minutes to Ridgefield, and about 15 minutes to downtown Katonah, placing shopping, dining, and commuting all within easy reach. This is far more than a beautifully renovated home. It delivers the level of design, finish, and amenities typically reserved for much larger custom-built estates, while offering the warmth, comfort, and livability of a true family home. Every space has been elevated, every detail considered, and every finish curated. Move-in ready doesn’t begin to describe it. This home is simply walk-in stylish.

2 Tommys Lane, South Salem

$899,000

4 Beds ⋅ 4 Baths ⋅ 1029839 MLS

Welcome to 1 Stonefield Court, an impressive four-bedroom Classic Colonial offering approximately 3,216 square feet of beautifully proportioned living space on nearly an acre of private property. Ideally positioned on a quiet cul-de-sac in Cortlandt Manor, this gracious home welcomes you with a charming front porch—the perfect place to enjoy your morning coffee or simply take in the peaceful surroundings. Inside, abundant natural light creates a warm and inviting atmosphere throughout. The expansive, flexible floor plan features generously sized rooms designed for comfortable everyday living and effortless entertaining. The main level includes a formal living room, an elegant dining room, and a beautiful center-island kitchen that opens to an expansive great room with a gas fireplace. Upstairs, the spacious primary bedroom features an en-suite bath and walk-in closet. Three additional bedrooms and a full hall bath complete the second level. The finished lower level provides fabulous recreational space with a powder room, currently arranged as a family room and game room, with endless possibilities for a home office, fitness area, media room, or guest accommodations. Outside, the approximately .91-acre property offers abundant space for outdoor dining, recreation, gardening, and relaxation. Whether hosting a summer gathering or enjoying a quiet afternoon at home, the private setting serves as a wonderful extension of the living space. Built in 1999 and beautifully situated within the desirable Cortlandt Manor community, 1 Stonefield Court offers an exceptional combination of space, privacy, comfort, and versatility—a special home ready to welcome its next owner.

1 Stonefield Court, Cortlandt Manor

$1,350,000

5 Beds ⋅ 4 Baths ⋅ 1034206 MLS

A once-in-a-lifetime opportunity to own Maplehurst Farm, originally known as the Conklin-Chadeayne Farmhouse, an irreplaceable Antique Farmhouse Colonial estate dating back to the 1730s, nestled on five irreplaceable acres in the highly sought-after community of New Castle. Rich in history and timeless character, this extraordinary property preserves many of its original architectural details, including wide-plank pine floors, original farm doors, hand-crafted millwork, and three fireplaces. Offering exceptional versatility, the estate is ideally suited as a private country retreat, equestrian property, or multi-generational residence. Set on over five picturesque acres, the grounds are a true sanctuary. Enjoy peaceful mornings on the multi-level stone patios surrounded by mature landscaping and native plantings, or gather with family and friends on the expansive covered front porch. Equestrian enthusiasts will appreciate the six-stall horse barn, multiple paddocks, and riding arena, while the heated 20' x 50' in-ground pool, complete with its own stone patio and custom-built pergola, provides the perfect setting for summer relaxation. Historic stone walls, crafted from stones found on the property, and impressive steps built from reclaimed West Point stone further showcase the estate's remarkable heritage. A gracious front porch welcomes you into the center hall. The main level features a living room with a wood-burning fireplace, an intimate reading room, formal dining room, eat-in kitchen with its own fireplace, powder room, family room, laundry room, and walk-in pantry. The second level features a spacious primary suite, three additional bedrooms, and a full bath highlighted by a timeless clawfoot tub. The approximately 1,200-square-foot finished walk-out lower level offers exceptional flexibility, featuring a spacious living and dining area with wide-plank flooring, a former tiled summer kitchen, two bedrooms with hardwood flooring—one with a fireplace—a storage/mechanical room, and multiple exterior entrances, creating an ideal space for extended family, guests, or a potential mother/daughter arrangement with the appropriate approvals. While this private estate feels like a world away, it is just minutes from the Village of Ossining, the scenic Hudson River waterfront, and an array of restaurants, shops, parks, hiking trails, and recreational activities that make the Hudson Valley such a sought-after destination. Located approximately 45 minutes from New York City, this extraordinary estate presents a rare opportunity to own an authentic piece of American history while enjoying the privacy, beauty, and lifestyle of a truly exceptional country property. Estates of this significance, craftsmanship, and versatility are exceedingly rare and simply cannot be replicated.

15 Inningwood Road, Ossining

$1,275,000

4 Beds ⋅ 3 Baths ⋅ 1020739 MLS

Nestled on a beautifully landscaped corner lot just under an acre in the highly sought-after Town of Mount Pleasant and within the Mount Pleasant School District, this exceptional 3,000+ square foot ranch offers the perfect blend of comfort, style, and functionality. Step inside to discover a welcoming living room adorned with gleaming hardwood floors, elegant wainscoting, and a stunning fireplace that seamlessly connects to a second expansive living room adorned with decorative ceilings and abundant with windows for a serene setting. The adjacent dining area flows effortlessly into the spacious eat-in kitchen, featuring granite countertops, stainless steel appliances, and endless cabinetry. A versatile mudroom just off the main living area provides the perfect space for a home office, pantry, or additional storage. The main level offers three generously sized bedrooms, including a luxurious primary suite complete with a walk-in closet, beautifully appointed granite bathroom, and very own private deck from your bedroom—offering your own peaceful retreat overlooking the property. A full hall bathroom serves the additional bedrooms. The finished walk-out lower level expands your living space with endless possibilities, featuring a bonus flex room ideal as a fourth bedroom, guest suite, gym, or office, a full bathroom, and a convenient summer kitchen—perfect for entertaining or extended family. Step outside to your own backyard wonderland, where an inviting in-ground pool is surrounded by ample outdoor space for relaxing and hosting summer gatherings. The newly blacktopped U-shaped driveway enhances both curb appeal and convenience, offering plenty of parking in addition to your 2-car garage. Combining spacious one-level living, flexible lower-level accommodations, exceptional outdoor amenities, and a premier Mount Pleasant location, this remarkable home truly offers everything today's buyers have been searching for. Don't miss this rare opportunity to own a home that perfectly balances elegance, comfort, and lifestyle.

236 Westlake Drive, Valhalla

$649,000

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

$1,229,000

4 Beds ⋅ 4 Baths ⋅ 1032845 MLS

STYLISHLY RENOVATED GEM in the highly desirable West Somers Park, where timeless elegance meets modern luxury. Nestled on a picturesque park-like property, this exceptional home is designed to impress with impeccable craftsmanship, sophisticated finishes, and thoughtful updates throughout. Step inside to a sun-drenched interior featuring oversized windows, soaring vaulted ceilings, custom moldings, coffered ceilings, and beautifully maintained hardwood floors. At the heart of the home is the spectacular 2024 designer kitchen, showcasing exquisite quartz and limestone countertops, premium top-of-the-line appliances, and exceptional attention to detail. The kitchen flows seamlessly into the oversized family room with a cozy gas fireplace, creating the perfect gathering space for everyday living and entertaining. The main level also features a sun-filled eat-in kitchen area, ideal for casual dining, as well as a formal dining room perfect for hosting elegant gatherings. The luxurious primary suite offers a peaceful retreat with an expansive walk-in closet featuring custom California Closets and a beautifully appointed spa-inspired ensuite bath. Two additional generously sized bedrooms and an updated hall bath complete the main level. The versatile lower level provides outstanding additional living space, including a fourth bedroom currently used as a workshop/home office, a spacious recreation room, full bath, summer kitchen, and an additional family room with a charming wood-burning fireplace—ideal for guests, extended family, hobbies, or entertaining. Outdoor living is equally impressive. Relax on the expansive upper deck overlooking your private backyard oasis, or unwind on the lower patio surrounded by lush landscaping. The stunning blue Gunite swimming pool and spa, custom-built poolside bar, architectural landscape lighting, and sprinkler system create endless opportunities for entertaining and enjoying resort-style living at home. This meticulously maintained residence has been extensively upgraded, including a Peerless four-section oil-fired burner (2022), Culligan water softening system (2023), Raypak PR406 pool heater (2023), pool heat pump (2024), 2.5-ton Daikin central air system (2024), 22KW whole-house Generac generator (2024), and Royal Haven insulated siding and gutters (2025) with a transferable warranty. Additional features include abundant storage, oil above-ground, attached two-car garage. Perfectly located just minutes from shopping, restaurants, top-rated schools, the North County Trailway, major highways, and Metro-North Railroad, this extraordinary home offers the ideal combination of luxury, comfort, and convenience. A home for those accustomed to fine living, don't miss this exceptional West Somers Park gem! Photos to come on 8/6

63 Raemont Road, Granite Springs

$685,000

3 Beds ⋅ 2 Baths ⋅ 1033712 MLS

Welcome to 617 Cardinal Road, a beautifully maintained and thoughtfully updated split-level home situated on a quiet cul-de-sac in Cortlandt Manor. Offering a perfect blend of comfort, functionality, and quality updates, this move-in-ready residence features an inviting layout with exceptional indoor and outdoor living spaces. The renovated kitchen is designed for both everyday living and entertaining, featuring granite countertops, a glass tile backsplash, GE gas cooktop with double electric ovens, GE Profile refrigerator, Bosch dishwasher, Brizo stainless steel faucet, under-sink water filtration, smart Lutron lighting, and updated windows and doors. Hardwood floors extend throughout the main and second levels, complemented by crown molding, updated base molding, and abundant natural light. The spacious living room is centered around a wood-burning fireplace and a large bay window, while the dining room offers custom window treatments and easy access to the outdoor living space. A mini-split system provides additional comfort, and the main living areas have been freshly painted. The upper level includes a beautifully renovated full bathroom and a spacious primary bedroom featuring refinished hardwood floors, custom window treatments, and an updated ceiling fan. The backyard is a true highlight of the property, offering an exceptional outdoor setting for relaxing and entertaining. Enjoy a spacious covered deck with built-in seating, custom table and chairs, and ceiling fans overlooking the beautifully landscaped yard. A charming paver patio, and a 15' x 30' above-ground pool create a private outdoor retreat perfect for hosting gatherings or enjoying quiet evenings at home. Additional highlights include updated siding, gutters, roof, replacement windows, updated heating and electrical systems, three-zone heating, an attached one-car garage, and a well-maintained septic system. Conveniently located near parks, shopping, restaurants, Metro-North, and major highways, this meticulously maintained home offers a wonderful combination of quality updates, comfortable living spaces, and exceptional outdoor amenities.

617 Cardinal Road, Cortlandt Manor

$4,995,000

5 Beds ⋅ 7 Baths ⋅ 1027507 MLS

Tucked away on a tranquil cul-de-sac in the prestigious Town of Bedford, this masterfully reimagined gated home defines the next generation of Bedford luxury real estate. Just a short, convenient jaunt from the energy of Manhattan, 2 Barry Court provides a seamless transition from city living to serene countryside retreat, making it an ideal residence for those seeking fresh air, privacy, and refined relaxation. More than just a home, this is a lifestyle property located near the historic Bedford Village Green, the scenic Bedford Riding Lanes, and the vibrant Katonah boutique district. Set on four manicured acres with mature trees and open sky, the estate invites you to unwind in total tranquility—whether for weekends or for full time living. Designed by revered architect Teo Siguenza and developed by the esteemed Grasso Development Corporation, the residence blends timeless character with modern luxury. Inside, a two-story foyer opens to light-filled, 10’ high living spaces, while a custom chef’s kitchen (with Subzero and Wolf appliances) flow effortlessly into a vaulted family room with a statement stone fireplace. The primary suite offers a private oasis with dual dressing rooms, spa-like baths, and its own sitting room with a fireplace. The home's exterior truly shines: a brand new heated gunite pool with automatic cover, pool cabana with full bath and an expansive bluestone terrace transform the property into a resort-style getaway. With its unique combination of proximity to New York City and complete privacy, this move-in-ready estate is perfectly suited for buyers seeking a luxurious home without sacrificing access to the city.

2 Barry Court, Katonah

$789,000

4 Beds ⋅ 3 Baths ⋅ 1031827 MLS

Welcome to this beautifully updated, spacious home nestled in one of the area's most sought-after neighborhoods! From the moment you arrive, you'll appreciate the exceptional curb appeal, featuring a stunning new front door with dual sidelights, new siding, a new roof, and replacement windows throughout the entire first floor. Step into your own private backyard retreat, where a fully fenced yard surrounds a spectacular in-ground pool ranging from 2 to 5½ feet deep. A solar-powered filtration system helps keep the water crystal clear and swim-ready, while the expansive paver patio provides the perfect setting for entertaining family and friends all summer long. The convenient pool house offers ample storage for pool equipment, toys, and accessories, and the pool can be maintained as either a saltwater or chlorine system to suit your preference. Inside, the versatile lower level is designed for both comfort and convenience, featuring a media room ideal for movie nights and gaming, an additional bedroom, a full bathroom, laundry area, and direct access to the garage. Pool guests will especially appreciate the easy outdoor access to the lower-level bathroom without needing to walk through the main living areas. The spacious primary suite offers a private ensuite bathroom, creating a comfortable retreat at the end of the day. Beyond the home itself, you'll love the beautifully maintained neighborhood, known for its manicured properties, low traffic, and welcoming atmosphere—perfect for walks, bike rides, and outdoor activities. This move-in-ready home offers the ideal blend of thoughtful updates, exceptional outdoor living, and a prime location. Schedule your private showing today and experience everything this wonderful property has to offer!

3320 Chelsey Street, Mohegan Lake

$3,495,000

4 Beds ⋅ 7 Baths ⋅ 1032753 MLS

Set on 11 idyllic acres, this unparalleled estate is a rare find in the Byram Hills School District in Armonk, NY, right on the Greenwich, CT border. A private gated entrance opens up to this peaceful retreat, with breathtaking grounds including European-style gardens, fieldstone rock walls, stone patios and an outdoor pizza oven, walking path that wind past a pond toward a spectacular in-ground Gunite pool and spa and through the gardens. Serene water views carry through much of the home and property, and the exquisite, extensive landscaping alone represents years of thoughtful design. The 6,639 square-foot brick home offers quality construction and unique architectural character throughout, including four spacious bedrooms and original mural artwork found in select rooms. Home includes many amenities such as a sauna, gym, greenhouse, workshop, balconies and third floor loft with built-ins. Two home offices and an additional 1200 sq ft in lower level. Located in the Byram Hills School District with a Greenwich, CT mailing address, the property is conveniently located 10 minutes to downtown Armonk and 15 minutes to downtown Greenwich, CT, with the privacy and scale of a country estate.

25 Edgar Road, Armonk

$599,000

4 Beds ⋅ 2 Baths ⋅ 1022241 MLS

Set on a beautiful 1.01-acre property in one of Yorktown Heights' most desirable neighborhoods, this classic Cape Cod offers a rare opportunity to create the home you've always envisioned. Featuring 4 bedrooms, 2 bathrooms, and 1,564 square feet per town records, this home is ready for its next owner to bring fresh ideas and make it their own. The main level offers a functional layout, while the partially finished basement provides additional flexible living space for a recreation room, home office, gym, or storage. Step outside to a spacious deck overlooking the private backyard and in-ground swimming pool, creating the perfect setting for future outdoor entertaining. Several major improvements have already been completed, including a roof (2016), water heater (2023), newer furnace, vinyl siding (2021), and replacement windows (2021), allowing the next owner to focus on updating the interior to match their style and vision. Conveniently located near parks, shopping, restaurants, schools, major highways, and the Jefferson Valley Mall. This property combines a sought-after location, generous lot size, and outstanding potential. A wonderful opportunity to add value and make this Yorktown Heights home your own.

2838 Mead Street, Yorktown Heights

$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

Homes for Sale with a Pool in Westchester, NY

All Homes for Sale with a Pool in Westchester, NY

Tierra Stanback