Lewisboro, NY Homes for Sale

Magnificent home set on 4.6 acres of land offering privacy with panoramic views and a pristine modern interior. The first floor of this home features a custom Poggenpohl kitchen with center island and high end appliances that flows to a casual dining and sitting area with a fireplace. The family room boasts a tray ceiling with sliding glass doors to an expansive deck overlooking the beautiful

Joseph Stilo Julia B Fee Sothebys Int. Rlty

Discover a rare opportunity on beautiful serene Lake Truesdale - A private waterfront retreat with 200 feet of shoreline. Set on a double lot with approximately 1/2 an acre of professionally landscaped property. The exceptional grounds feature a private dock, pristine sandy swimming area, park like yard with stunning western facing views across the lake. Inside, the home offers a modern open -

Sandra Katter KATTER PROPERTY COMPANY INC

Welcome to this exceptional offering in one of Northern Westchester’s most private and sought-after communities. Set on two+ beautifully landscaped acres, this extensively upgraded home blends timeless elegance with modern comfort, featuring sun-filled interiors, refined details, 3 bedrooms plus a versatile bonus room—perfect for a home office, guest room, or au pair—that lives like a 4-bedroom,

Eva Casoria eXp Realty

Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc. Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The

Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

COUNTRY PERFECTIONThoughtfully sited upon over two beautifully landscaped acres against a scenic wooded backdrop, this meticulously maintained, updated five-bedroom classic colonial offers the perfect combination of peace, privacy, convenience, nature, and award-winning Katonah-Lewisboro schools in a quiet country setting. Move right in with nothing to do but plan your summer garden of

Anne-Marie Nordgren Coldwell Banker Realty

A truly exceptional property situated high above Milne Lake. This residence offers breathtaking 180-degree water views, soaring ceilings, and abundant natural light throughout. Set on 4.13 acres, the estate is surrounded by nature and features a variety of premium amenities, including private walking paths, Zen gardens, bridges over streams, a dedicated pond and waterfall, and a tennis court. For

Hannelore Kaplan William Raveis Real Estate

From the moment you turn down the long, secluded driveway toward 1 Sabbath Day Hill Rd, the feeling is unmistakable: this is a retreat built for those who prize privacy, elevation, and quiet grandeur. Perched atop its own hill and surrounded by mature trees, the home sits back from the road with views visible from the wide front porch—a space that feels like your own private veranda overlooking

Alex Mashkin Keller Williams Realty Partner

Sold as is, house needs total renovation. Cash buyers only. Backs up to the Leon Levy Preserve, access to Lake Kitchawan Lake. Tucked away along the quiet shoreline of Lake Kitchawan, this modest cape presents a rare chance to reimagine a home in one of Northern Westchester most natural settings. Set on a small parcel that backs directly onto the protected woodlands of the Leon Levy Preserve.

Cecilia Heller Houlihan Lawrence Inc.

Western View. Over one park-like acre with rolling lawns, flowering plantings and towering trees. First time listed in years, distinctive Country House with elements of a classic deck house. Warm interior spaces with hardwood floors and vaulted ceilings finished in wood. Sun-filled Living Room with fireplace and doors to front deck, ideal for relaxation. Dining Room with vaulted ceiling. Country

Peter Michaelis Ginnel Real Estate

This wonderful, open-concept Contemporary/Split home enjoys a cozy, private setting, and includes vaulted ceilings, hardwood floors, and an abundance of natural light creating a bright and airy atmosphere. Enter into the light filled foyer with a soaring ceiling and views into the main and lower levels. The main level includes the living room, dining room, and kitchen, all flowing together under

Gerry Weil Keller Williams Realty Partner

Calling all investors, builders, and contractors. 10 Beech Road presents a prime value-add opportunity on a quiet dead-end road in the desirable Lake Kitchawan community. This 3-bedroom home situated on approximately 0.43 acres is ready for renovation and ideal for cash buyers or purchasers using a rehab loan looking to create value. As a member of the Lake Kitchawan Association, owners enjoy

Anna Proctor Compass Greater NY, LLC

Discover the perfect blend of privacy, versatility, modern updates, and original charm. Set on five breathtaking acres featuring a private pond and lush wooded surroundings, this retreat is located just minutes from Katonah Village, Metro-North, and major commuter highways. The flexible layout is officially a 3-bedroom plus a home office, with the office functioning as a true flex space that can

Christine Trudeau Keller Williams Prestige Prop

This value-packed, move-in-ready upper-level condominium is located at the end of a cul-de-sac in Oakridge Condominiums, Vista, NY. Offering approximately 1,312 sq ft, this residence includes a vaulted loft and a bonus room. This home provides a flexible living space ideal for a home office, den, exercise room, hobby area, or additional storage. This south-facing home features a landscaped garden

Teresa Rivers Coldwell Banker Realty

If you’ve been dreaming of a chic, nature-filled retreat with modern upgrades and the rare convenience of WALKING to the train, this is the one that captures it all. Tucked into a breathtaking .78 acre setting with sweeping mountain views, this picture-perfect Colonial—FULLY renovated in 2023—offers a rare blend of refined style and serene. Nature-filled living in the highly coveted Goldens

Lisa DaRos Houlihan Lawrence Inc.

Nestled on a serene, tree-lined cul-de-sac in a wonderful neighborhood setting, this light-filled 4-bedroom, 2.1-bath Contemporary home is privately set on 2 beautiful acres within the award-winning Katonah-Lewisboro School District. Offering the perfect balance of tranquility and convenience, this move-in ready home features an open-concept layout designed for comfortable everyday living.

Cindy Glynn Compass Greater NY, LLC

Welcome to 31 Spring Street South in beautiful South Salem, NY — a lovingly maintained expanded ranch being offered for the first time in decades. Nestled on a private, sun-drenched property with mature landscaping and estate-like grounds, this special residence offers the perfect blend of tranquility, space, and opportunity. Featuring 4 bedrooms/2 full bathrooms, this picturesque property also

Kathryn Norman Market Match Real Estate Corp

Beautifully updated and move-in ready, this 4-bedroom home is set on 2 private acres in the highly desirable Katonah-Lewisboro School District. Thoughtfully renovated throughout, the home features refinished hardwood floors, fresh neutral interiors, brand-new stainless steel appliances, 2 full bathrooms, and an updated powder room.The light-filled open layout offers comfortable everyday

Sari Shaw Compass Greater NY, LLC

Set along the shoreline of Lake Oscaleta, this direct waterfront home offers a rare combination of privacy, natural beauty, and truly usable lakefront property in the heart of South Salem. Occupying .564 acres with sweeping frontage on one of the area’s most peaceful glacial lakes, the setting is defined by something increasingly hard to find - an expansive, level lawn that extends all the way to

Adam Hade Compass Greater NY, LLC

Welcome to your own private sanctuary—a meticulously maintained and thoughtfully updated home. Featuring a 1,620-square-foot retreat where nature meets elegance at every turn. Built in 1946 and lovingly cared for, this exceptional South Salem property offers the rare combination of tranquil seclusion and premier location in the sought-after Katonah-Lewisboro school district. A fabulous setting

AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

This move-in ready colonial offers a functional layout for everyday living and entertaining, in a serene setting. The home’s orientation provides leafy views of the woodsy property, pond, and old stone walls. On the main floor, there is a newly updated eat-in kitchen, a large family room with a cozy fireplace, large living and dining rooms, outdoor space on the deck, and access to a two-car

Larry Mango Giner Real Estate Inc.

Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for

Joseph Lukic Compass Greater NY, LLC

Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our Appraisal describe the property as a SFR (colonial) built in 1980. It has a GLA of approx. 2100 and has 3 bedrooms and

Christopher Rose REALHome Services & Solutions

Set on a manicured 1.78-acre lot, this beautifully updated 4-bedroom, 2.5-bath Colonial located in the sought after community of Michelle Estates, is a must see. Step inside to a grand, two-story foyer, featuring high ceilings and an elegant open staircase. To the right, is a private home office with French doors and to the left a formal living room which flows seamlessly into the dining room.

Patricia Hinkley Coldwell Banker Realty

Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of

Nikki McMann William Raveis-New York LLC

Welcome to your whimsical lakefront paradise on magnificent Lake Oscaleta! This charming, thoughtfully updated 1930s cottage offers a rare and magical opportunity to experience true waterfront living. Perfectly positioned right at the water’s edge, this two-bedroom, two-bathroom retreat beautifully replicates the enchanting feeling of living on a houseboat, surrounded by panoramic nature and

Paul Tollefson William Raveis-New York LLC

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully

Samuel Berek Serhant LLC

First time on the market from the original owner, this rare and uniquely captivating estate, 80 Hack Green Road, perfectly reflects its prestigious address. Privately set on almost three impeccably landscaped, completely flat acres between Scotts Corner and New Canaan, this distinguished brick and stucco colonial Tudor offers approximately 4,000 square feet of exceptional craftsmanship and

Natalia Wixom Compass Greater NY, LLC

Location is everything-and this one delivers. Nestled on a quiet cul-de-sac in the sought-after West Lane section of Ridgefield, this property offers the ultimate combination of privacy, neighborhood charm, and unmatched convenience. Just 15 minutes to the Katonah Metro-North line, one hour to NYC by car, minutes to downtown New Canaan, Ridgefield & nearby NY/CT state parks, this is one of the

Kyle Neumann Houlihan Lawrence