Katonah-Lewisboro Homes for Sale

Welcome to the picturesque Katonah-Lewisboro School District, nestled in the heart of Westchester County, New York. Known for its commitment to academic excellence, this district serves families in the charming communities of Katonah, Lewisboro, and surrounding areas. With a strong emphasis on fostering a love for learning, the district boasts a variety of innovative programs and extracurricular activities that nurture students' talents and interests. Parents can rest assured knowing their children are receiving a top-tier education from dedicated educators in well-equipped facilities.

The Katonah-Lewisboro School District is renowned for its small class sizes, ensuring personalized attention for each student. The district offers a comprehensive curriculum that includes Advanced Placement courses, arts, and athletics, preparing students for success in their future endeavors. With a strong sense of community, families often find themselves engaged in school events, fostering relationships that last a lifetime.

For those considering a move to this idyllic region, there are a variety of homes for sale that cater to diverse lifestyles and preferences. From charming colonial homes to modern new builds, the real estate options in Katonah and Lewisboro are as varied as the families who call it home. Enjoy the serene surroundings, picturesque landscapes, and a welcoming community atmosphere, all while being a part of a school district that prioritizes educational excellence.

Discover your dream home in the Katonah-Lewisboro area today and become a part of a vibrant community that values education, family, and a bright future!

Newest Katonah-Lewisboro Homes for Sale

$700,000

3 Beds ⋅ 3 Baths ⋅ 1051757 MLS

Offered for sale for the first time, this three-bedroom, two-and-a-half-bath home is set back from the road on two private acres. Beautifully cared for throughout, the kitchen and baths have a fresh, updated feel, complementing the home's comfortable proportions and easy floor plan. Outside, mature trees and open lawn create a peaceful setting with plenty of room to garden, gather or simply enjoy the outdoors. An exceptionally well-kept home in South Salem, with easy access to the nearby hamlet of Vista and just over the border from Ridgefield, Connecticut.

257 Smith Ridge Road, South Salem

$1,795,000

4 Beds ⋅ 6 Baths ⋅ 1045136 MLS

Offered for the first time since it was built by the original owners, 30 Pine Hill Drive is a private and beautifully maintained residence on 3.95 acres along one of Lewisboro’s sought-after streets. Beyond the home, the property itself is a treasure—wooded on three sides, offering exceptional privacy, a beautiful usable yard, stone walls and even a peaceful brook along the rear of the property. Tons of oversized windows bring the outdoors in, capturing beautiful views across the grounds and filling the home with natural light. The thoughtful layout offers generous living spaces and a versatile floor plan designed for the way people live today, with options for dedicated home offices, a guest suite, gym or wellness space, playroom, game room, media room, library or hobby space. Four full baths, including three en-suite, and two half baths provide exceptional flexibility for family and guests. Warm cherry cabinetry adds a timeless touch, while the three-car garage provides ample parking and storage. Recent improvements include a brand-new roof and gutters, new oil tanks, boiler and hot water heater. A full walk-out lower level offers the opportunity to create additional living space, while a five-bedroom septic provides added flexibility. With the exceptional trails and preserved beauty of Ward Pound Ridge Reservation, Westchester County's largest park nearby, this is a setting that invites you to slow down, explore and truly enjoy the outdoors. Yet despite its tranquil country feel, the location is remarkably convenient. Katonah, Ridgefield, Pound Ridge and Bedford are all close at hand, offering restaurants, shopping, markets, services and cultural amenities, with town parks and recreation nearby. A coveted Lewisboro location, award-winning Katonah-Lewisboro schools, exceptional privacy and a wonderful connection to the outdoors come together at 30 Pine Hill Drive—a rare opportunity to make this home yours.

30 Pine Hill Drive, South Salem

$995,000

4 Beds ⋅ 4 Baths ⋅ 1050837 MLS

Move-in ready and beautifully maintained, 9 Cross Pond Road offers refined country living in a private South Salem setting. Beautiful landscaping, stonework, hardwood flooring throughout, and a newly resealed driveway create a welcoming first impression. A privacy fence and direct proximity to the Leon Levy Preserve provide a serene, natural backdrop. The updated kitchen and beautifully renovated baths complement the home’s warm, sophisticated interiors. The finished walk-out lower level, adds an additional 700SF, opens to a private patio and features a sauna and summer kitchen—ideal for relaxed entertaining and everyday enjoyment. The home offers 4 generously scaled bedrooms and a whole-house generator for added convenience and peace of mind. Approximately 7 miles to the Goldens Bridge Metro-North station and I-684, this exceptional property combines privacy and tranquility with easy access to commuting, shopping, and the best of the Westchester lifestyle.

9 Cross Pond Road, South Salem

$999,000

3 Beds ⋅ 2 Baths ⋅ 1033118 MLS

Set in the heart of Katonah, 22 Hillside Avenue offers a wonderful combination of comfort, character and convenience within the award winning Katonah Lewisboro School District. The inviting main level features a bright living room and updated kitchen with stainless steel appliances, with easy access to both the dining room and patio for al fresco dining and gathering. The home has an easy flow for everyday living and entertaining, with beautiful hardwood floors throughout. Three bedrooms include one currently transformed into a beautifully designed dressing room with custom cabinetry, offering flexibility to suit your needs. Two full baths complete the living space. Additional highlights include a bright sunroom/office and a dedicated workshop/workspace, providing valuable additional space for projects or hobbies. Leave the car at home and head into town for the train, shops and restaurants, all just moments away. This is a rare opportunity to enjoy Katonah’s distinctive combination of small town charm and everyday convenience, and one not to be missed! Updates/upgrades include: 200 amp service (2020), all windows (minus sun room) replaced w/solid vinyl tilt in-window units and new storm doors at entrance & sun room (2020); house painted (2021); driveway paved (2026)

22 Hillside Avenue, Katonah

$1,399,000

4 Beds ⋅ 4 Baths ⋅ 1035228 MLS

Stunning 4000+ sq. ft. contemporary colonial on over six sprawling acres in one of Waccabuc’s most sought after cul-de-sac neighborhoods. Set back amidst classic stone walls, rolling lawns, soaring uplit trees in front and back, and blooming perennials, this immaculate home offers an exceptional indoor/outdoor lifestyle in a profoundly peaceful setting. Inside, a sunlit entry foyer with high ceilings introduces an open and versatile floor plan. The inviting front-to-back living room offers custom built-ins, a fireplace, and a window seat. A beautifully appointed cook’s kitchen features a large center island, induction cooktop, wine fridge, and views of the backyard. An open eat-in area seamlessly flows into the bright and airy family room with two story cathedral ceilings, sky lights, wood-burning fireplace, wet bar, and sliders out to the expansive deck where you can take in the panoramic views. A gracious formal dining room, powder room, laundry room, and access to the attached two-car garage complete the main level. Upstairs, the large primary bedroom suite is a retreat in itself, featuring a large walk-in closet and a spa-like bathroom, also with beautiful private views of the property. Down the hall, there are three additional spacious bedrooms and a beautifully renovated hall bath. The light-filled fully finished lower level features incredible additional flex space with a full bathroom, office, large living/play/gym area and sliders out to the sweeping lawns. Take in the meadows, dine and grill on the deck, or enjoy the scenic views from inside - an unbeatable lifestyle awaits you here. All of this conveniently located near Metro-North, schools, award-winning local restaurants, shopping, hiking and premier golf & tennis clubs.

12 Hilltop Road, Waccabuc

$3,195,000

4 Beds ⋅ 5 Baths ⋅ 1050330 MLS

STUNNNING & SOPHISTICATED. Striking re-imagination of a classic Deck House completely transformed and expanded in 2024. Stunning use of natural materials and sophisticated style. Desirable open floorplan highlighting the elements of the original design. Vaulted ceilings finished in wood, exposed beams and walls of windows create a sun-filled living space. Two-story Entrance Hall. Impressive Living Room with soaring ceiling, pendant lighting and fireplace finished in Moroccan tile. Open Dining Room amply proportioned for entertaining. Sleek Chef’s Kitchen with custom Bilotta cabinetry, Quartz counters, a marble backsplash and high-end appliances. Comfortable Family Room seating area. Choice of Offices for working remotely. Four Bedrooms include private Primary and Guest Suites. Lower level flex space with Media and Recreation areas. Finished Garage currently housing Home Gym. Ipe decking around private Swimming Pool. Gated drive to over five peaceful acres with babbling brook, verdant lawns, towering trees and specimen plantings. A magical setting near the protected lands of the Ward Pound Ridge Reservation. The perfect peaceful refuge!

21 Black Spring Road, Pound Ridge

$685,000

2 Beds ⋅ 3 Baths ⋅ 1049328 MLS

Easy, stylish, and exceptionally well connected. This beautifully renovated Wild Oaks townhome makes Northern Westchester living feel effortless. Step inside to a thoughtfully designed, one-of-a-kind contemporary interior with soaring ceilings, custom metal railings, stacked-stone fireplace surround, fluted wood panel feature wall, and ultramodern sconces. United throughout by a cohesive color scheme, a nicely designed kitchen & 3 renovated bathrooms mean that you can move right in without having to worry about the never-ending "to-do" list. When the weather is nice, an expansive deck becomes the place to be. Sip your morning coffee under the trees, enjoy dinner al fresco, tend to your herb garden, or host a full house of friends on a summer evening. Each bedroom is situated on its own level with its own ensuite bathroom, and storage closets are abundant throughout. A legal finished lower level adds an additional 425 square feet of bonus space - perfect for a home office, gym, playroom, media room, or whatever life calls for next. Then there are the practical perks that make a great home even better: a generator, central air & forced-air heating, high-end Andersen windows, attached garage, bonus driveway parking, and easy access to I-684. Best of all, Metro-North is just minutes away, making the commute to NYC refreshingly simple. Stylish, spacious, low-maintenance, and close to everything. This is the kind of home that just makes life better. By Appointment Only.

9 Boulder Lane, Goldens Bridge

$2,900,000

5 Beds ⋅ 5 Baths ⋅ 1037090 MLS

Set behind stone pillars at the end of a meandering private drive, this custom-built stone manor draws its inspiration from a 19th-century English manor house. This home features a rare blend of Old World craftsmanship and modern-day comfort on more than four private, lushly landscaped acres, just about an hour from New York City. Built in 1988 and thoughtfully updated since, the residence features Five fireplaces anchor the home's principal rooms. The living room, a soaring 39' x 24' space with 12' coffered pine ceilings and a massive floor-to-ceiling stone fireplace, sets a formal yet inviting tone, while the library's built-in cabinetry and Art Deco lighting bring a warmer, more contemporary counterpoint. The gourmet kitchen is a true tour de force, outfitted with Neff cabinetry, Viking appliances, and its own floor-to-ceiling stone fireplace. A library with French doors opens directly onto a stone terrace, ideal for quiet mornings or evening entertaining. Upstairs, the primary suite is accessed through a generous sitting room/office with its own fireplace and continues into a bedroom with a tray ceiling and another fireplace, as well as a dressing area with a lovely walk-in closet and a spacious primary bath. Three additional bedrooms and a bath complete the sleeping quarters. Outdoors, the grounds are just as considered as the interiors: an oversized heated gunite pool and spa, surrounded by extensive stone terracing, formal and English gardens, and manicured lawns. The detached three-car garage includes a heated guest, staff, or au pair suite with a full bath, offering flexible space for visitors, live-in help, or a private studio/office. Notable amenities include marble and granite finishes throughout, gleaming hardwood floors, and 9' and 12' ceilings. Every detail reflects a home that was built without compromise and maintained the same way. Zoned for the highly regarded Katonah-Lewisboro School District, including Meadow Pond Elementary School, John Jay Middle School, and John Jay High School, this is a rare offering for buyers seeking a full-time residence or a refined weekend retreat within easy reach of Manhattan.

295 Salem Road, Pound Ridge

$879,000

4 Beds ⋅ 3 Baths ⋅ 1043046 MLS

Welcome to 7 Nash Road — a move-in ready, four-bedroom, two-and-a-half-bath home in the sought-after town of North Salem. Set on a quiet road surrounded by natural, scenic beauty, this property offers the tranquility of a country retreat with exceptional commuter convenience. The updated kitchen provides a fresh, timeless space for everyday living and entertaining, while the adjacent living room, anchored by a wood-burning fireplace, creates a natural focal point for gatherings. Upstairs, four well-proportioned bedrooms and two updated baths offer plenty of room for everyday life and guests alike. Step outside onto the large front deck and take in the peaceful setting — perfect for morning coffee, outdoor dining, or simply enjoying the surroundings. A one-car heated garage and dedicated storage room complete the home. Beyond the property, enjoy everything Lewisboro has to offer: day camps, ball fields, a town pool, and more. Just minutes from the train, this is an ideal opportunity for those seeking a lifestyle that combines nature, community, and an easy commute. Part of the Katonah Lewisboro School District.

7 Nash Road, North Salem

$1,750,000

4 Beds ⋅ 4 Baths ⋅ 1033318 MLS

Stunning, one-of-kind, octagonal lakefront residence on Truesdale Lake, with 4 bedrooms, 3.5 bathrooms, 2-car garage, breathtaking lake views, custom rustic décor, open floorplan, vaulted ceilings, custom woodwork, wide plank flooring, built-in bar, interior stone fireplace, wrap-around decking, on .57 acres. Don’t miss out on this opportunity!

33 Truesdale Lake Drive, South Salem

$1,550,000

4 Beds ⋅ 3 Baths ⋅ 1043728 MLS

BY APPOINTMENT ONLY - Set behind an elegant iron gate and long private driveway, this beautifully landscaped 3.46-acre property offers a rare combination of privacy, space, and potential. With 0.5-acre zoning, for possible subdivision. Tucked away from the road, this contemporary four-bedroom, 2.5-bath home offers spacious and versatile living, including eat-in kitchen, dining room, inviting family room with fireplace, and an extra-large formal living room. The second floor features four generously sized bedrooms, two full bathrooms, and an expansive bonus room ideal for a home office, recreation space, or additional living area. An unfinished basement provides ample storage and potential for future use. Ideally located close to shopping, restaurants, and everyday conveniences, with the added benefit of being within a short walk to Goldens Bridge Metro-North train station. A wonderful opportunity to enjoy privacy and expansive grounds while remaining conveniently connected to the surrounding area.

361 Rte 22, Goldens Bridge

$1,995,000

3 Beds ⋅ 3 Baths ⋅ 1046466 MLS

9 Lewis Road is the most charming country compound in Pound Ridge. Tucked behind a white gate this completely fenced stone -and-shingle home is privately set on nearly three beautifully landscaped acres and offers a rare combination of character, privacy, and move-in-ready appeal. This jewel-box property welcomes you through a lovely foyer into a spacious living room with oversized windows and views of the gardens and pool—an inviting setting for entertaining. At the heart of the home, the country kitchen, breakfast area, and family room flow seamlessly together, creating a warm and comfortable gathering space. The family room features a wood burning fireplace and high ceilings with beams. The homes kitchen is thoughtfully appointed with a classic blue AGA stove, adding both character and functionality. Rich wood floors, sun-filled rooms, and lots of windows off the family room offer lovely views of the green, private property and create an effortless connection between the interior and surrounding grounds. The main level also features a spacious primary bedroom with high ceilings, new custom California closets and french doors opening to a private terrace. Attached is a beautiful primary bath with a soaking tub, spa like shower and heated floors. An additional room is ideally suited for a home office or nursery. The finished lower level includes a cozy sitting room, two comfortable guest suites and a newly renovated shared bath, offering family and guests a private retreat. The outdoor spaces are equally impressive, with stone terraces, bluestone patios, a beautiful pool, mature landscaping, and ample room for gardens, all set against a backdrop of peaceful wooded privacy. A recently renovated, separate two-bedroom cottage provides exceptional accommodations for guests, extended family or rental income. With a tenant in place till August 2027 providing immediate rental income. When the the current tenancy ends, continue it as an income producing rental or imagine what you might want this special little bungalow to become for your own life. Private, picturesque, and full of character, this special property captures everything buyers love about life in Northern Westchester. Perfect for full-time living, or as a quiet escape from NYC, it offers a wonderful sense of privacy and ease. From the moment you arrive through the front gate, it feels like home. *Listing imagery (interior & exterior) includes digitally curated design enhancements.

9 Lewis Road, Pound Ridge

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