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Lewisboro, NY Houses for Sale

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  • /50

    $1,100,000 Open Sun 1PM - 3PM

    • 5 Beds
    • 4.5 Baths
    • 3,648 Sq Ft

    1196 Route 35, South Salem, NY 10590

    A Timeless Retreat with Modern Luxury in LewisboroTucked away on 5.33 private acres, this extraordinary Cape Cod-Split Ranch is a seamless fusion of classic elegance and modern sophistication. Thoughtfully redesigned and fully upgraded in the past five years, this 5-bedroom, 4.5-bathroom estate spans 3,648 sq. ft., offering an unparalleled living experience. With five-zone heating and

    Zulleyma Alvarez Compass Greater NY, LLC

    1196 Route 35, South Salem, NY 10590
  • /23

    $2,295,000

    • 4 Beds
    • 3 Baths
    • 3,476 Sq Ft

    50 Cove Rd, South Salem, NY 10590

    On the Shores of Lake Waccabuc. Absolutely amazing setting overlooking the water! Incredible Lakehouse offering true waterfront living with panoramic views. Originally built in 1939 and beautifully updated in 2015. Fabulous Living Room with vaulted ceiling, floor-to-ceiling stone fireplace and knotty pine paneling. Stunning open-layout Kitchen with dining and seating areas, window walls and

    Christine Byrne Ginnel Real Estate

    50 Cove Rd, South Salem, NY 10590
  • /35

    $2,399,000

    • 3 Beds
    • 2.5 Baths
    • 2,262 Sq Ft

    38 Gilbert St, South Salem, NY 10590

    Spectacular Lakefront Jewel. Stunning Lakehouse in a breathtaking waterfront setting. One of the original lakehouses, circa 1926, painstakingly renovated and updated. Meticulously detailed and timeless interior spaces with Plain English designed Kitchen, custom millwork, steel casement windows, Galbraith & Paul wall coverings and bespoke fixtures and fittings. Beautifully finished Living Room

    Mindy Weil Ginnel Real Estate

    38 Gilbert St, South Salem, NY 10590
  • /34

    $1,149,000

    • 4 Beds
    • 3.5 Baths
    • 3,924 Sq Ft

    295 N Salem Rd, Waccabuc, NY 10597

    Welcome to one of Northern Westchester’s most architecturally unique and energy-efficient homes plus a newly added accessory apt suite—tucked away on a peaceful two-acre setting in Waccabuc. This thoughtfully expanded 4-bedroom, 3-bathroom geodesic dome combines striking design with everyday comfort and function. Soaring ceilings and distinctive triangular windows flood the home with natural

    Aurora Banaszek Compass Greater NY, LLC

    295 N Salem Rd, Waccabuc, NY 10597
  • /47

    $1,461,000

    • 4 Beds
    • 4.5 Baths
    • 4,078 Sq Ft

    1 Canaan Cir, South Salem, NY 10590

    Elegantly updated Modern Colonial with majestic curb appeal on a quiet country cul-de-sac. Ten minutes to Wilton/New Canaan (Connecticut) train stations. Picture perfect corner lot in gorgeous Northern Westchester, A grand foyer with double height ceilings ushers you into generously sized rooms with three cozy wood burning fireplaces. Eight French doors from three welcoming rooms open out onto a

    Juergen Hess Five Corners Properties Inc

    1 Canaan Cir, South Salem, NY 10590
  • /32

    $2,799,000

    • 5 Beds
    • 8 Baths
    • 7,313 Sq Ft

    41 Rock Shelter Rd, Waccabuc, NY 10597

    Experience sophisticated Waccabuc living in this stunning 7,313 SF shingle-style masterpiece, nestled on a quiet cul-de-sac, in the coveted Rock Shelter neighborhood, within the award-winning Katonah-Lewisboro School District. Elegant millwork, soaring ceilings, and five fireplaces create a warm, inviting ambiance throughout. Designed for both lavish entertaining and intimate gatherings, this

    Jessica Cunningham

    41 Rock Shelter Rd, Waccabuc, NY 10597
  • /50

    $1,900,000

    • 2 Beds
    • 3.5 Baths
    • 3,778 Sq Ft

    33 Truesdale Lake Dr, South Salem, NY 10590

    Welcome to a unique sanctuary that marries expert design with masterful craftsmanship in every detail. This lakefront home greets you with a welcoming lodge-style entry, leading to an open and flexible floor plan that epitomizes resort-style living. Architectural highlights include exposed structural wood beams, vaulted ceilings, walls of windows, French doors, reclaimed dark wood flooring, and

    Jonathan Gineo Jonathan D. Gineo

    33 Truesdale Lake Dr, South Salem, NY 10590
  • /23

    $999,000

    • 4 Beds
    • 2.5 Baths
    • 2,626 Sq Ft

    16 Stonewall Ct, South Salem, NY 10590

    Classic Colonial on 2 Perfectly Level and Gorgeous Acres, Boarded by Old Stone Walls At The End Of The Cul-De-Sac.Beautiful Kitchen with Stainless Steel Appliances and Custom Quaker Made Cherry Cabinets.Lustrous Hardwood Floors.Beautiful New Baths with Radiant Heat.2- Zone Heating and Central Air.Solid Wood Interior Doors.Very Spacious 4 Bedroom

    Cecilia Heller Houlihan Lawrence Inc.

    16 Stonewall Ct, South Salem, NY 10590
  • /45

    $899,000

    • 3 Beds
    • 2 Baths
    • 1,760 Sq Ft

    28 Glen Dr, South Salem, NY 10590

    Modern Rustic Retreat with Wraparound Views & Water FeaturesWelcome to this exceptional modern-rustic home that seamlessly blends mountain-lodge charm with updated comfort and style. Set back from the road, a long private driveway lined by an extensive, hand-built rock wall leads you to this striking residence — offering both curb appeal and a sense of arrival.Step onto the dramatic

    Frederick Cindrich Giner Real Estate Inc.

    28 Glen Dr, South Salem, NY 10590
  • /27

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,548 Sq Ft

    20 Boutonville Rd, South Salem, NY 10590

    Discover the charm of this beautifully maintained home offering spacious, sunlit interiors and a peaceful setting. The newly renovated kitchen flows seamlessly into a bright formal dining room and an elegant living room featuring a classic brick fireplace and access to a screened-in deck—perfect for indoor-outdoor living. Entertain with ease in the expansive family room, complete with sliding

    Alexander Marks William Raveis-New York LLC

    20 Boutonville Rd, South Salem, NY 10590
  • /27

    $225,000

    • 1 Bed
    • 1 Bath
    • 1,176 Sq Ft

    17 W Main St, Goldens Bridge, NY 10526

    Multiple offers, best- final offers due Monday 7-28 at 3:00. Back on market. Rare opportunity to live in a northern Westchester lake community, Goldens Bridge Lake Community, also known as The Colony, boasts cooperative spirit and consists of approximately 150 acres, with 17 acres will remain in a "forever wild " state for the enjoyment of residents to explore. Timber Lake has a beachfront area

    Suzanne Welch Coldwell Banker Realty

    17 W Main St, Goldens Bridge, NY 10526
  • /27

    $799,000

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft

    242 Smith Ridge Rd, South Salem, NY 10590

    For the purest...an enchanting historic treasure offered for the first time in over 50 years. Circa 1776 center chimney Farmhouse. Impeccably maintained array of unspoiled, remarkable period detail. Extraordinary wide board flooring throughout. Exposed beams and woodwork. Three fireplaces off the huge center chimney. High ceilings for the period.Cobblestone lined gravel drive leads to this

    Timi Parsons Houlihan Lawrence Inc.

    242 Smith Ridge Rd, South Salem, NY 10590
  • /31

    $640,000

    • 3 Beds
    • 1.5 Baths
    • 1,360 Sq Ft

    59 Grandview Rd, South Salem, NY 10590

    Welcome to South Salem! This beautiful split level home sits nicely on a hill and has a huge private lot. The main floor features an open modern eat-in kitchen, dining room, foyer and living room with a fireplace. The top floor has a beautiful master bedroom with a half bath that connects to a full bath which leads into the hallway, and two more bedrooms. The basement is split in half, one half

    Andres Sarmiento RE/MAX Distinguished Hms.&Prop

    59 Grandview Rd, South Salem, NY 10590
  • /2

    $625,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 1.5 Baths
    • 1,324 Sq Ft

    16 Indian Ln, South Salem, NY 10590

    This charming cottage offers classic period architecture and serene views of Lake Truesdale. The expansive living room has vaulted ceilings, exposed wood beams, and a stone fireplace. Large sliding doors allow for plenty of natural light. New energy-efficient windows were installed throughout the house less than a year ago enhancing the views from the kitchen and dining room. Inside, you'll find

    Mark Boyland Keller Williams Realty Partner

    16 Indian Ln, South Salem, NY 10590

Why Live in Lewisboro

On the border between New York and Connecticut is Lewisboro, a town swathed in nature and greenery 57 miles from New York City. The community is known for its preserved land and highly rated school system. “Lewisboro attracts people looking for the ...

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