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Lewisboro, NY Homes for Sale

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  • /38

    $669,900

    • 3 Beds
    • 2 Baths
    • 2,112 Sq Ft

    48 Lockwood Rd, South Salem, NY 10590

    SELLER WANTS THIS HOME SOLD ASAP, PRICED LOWERED TO $669,000, WELL BELOW MARKET VALUE..Elegance & Tranquility in the Heart of South Salem, welcome to 48 Lockwood!Discover the perfect harmony of refined living and peaceful seclusion in this beautifully renovated residence, gracefully sited on 3.48 acres of lush, private land. Tucked away in one of South Salem’s most desirable

    Agent Photo

    Pino Masucci

    River Realty Services, Inc.

    (914) 785-6711

    48 Lockwood Rd, South Salem, NY 10590
  • /34

    $1,950,000

    • 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
  • /45

    $899,000 Open Sun 12PM - 2PM

    • 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
  • /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
  • /22

    $1,195,000

    • 4 Beds
    • 2.5 Baths
    • 3,100 Sq Ft

    4 Scenic Dr, South Salem, NY 10590

    Set on a beautifully maintained private one acre, this classic Colonial offers 4 bedrooms and 2.5 bath. Step into a spacious and inviting layout where the entry opens to a bright living room filled with natural light. A wood-burning fireplace serves as a cozy focal point, perfect for relaxing evenings or gathering with loved ones. The formal dining room provides a refined setting for hosting

    Mark Boyland Keller Williams Realty Partner

    4 Scenic Dr, South Salem, NY 10590
  • /30

    $1,200,000

    • 3 Beds
    • 3.5 Baths
    • 3,548 Sq Ft

    7 Hunt Farm Rd, Waccabuc, NY 10597

    Hunt Farm, an idyllic community of traditional homes built around beautiful open green space and preserved woodlands. Lush landscaping, old stone walls, walkable private roads all maintained by The Hunt Farm Home Owners Association to preserve the warm character of this community. This 3 bedroom 3 1/2 bath colonial has 3,500 square feet of sun filled living spaces including family room open to

    Susan Berman

    7 Hunt Farm Rd, Waccabuc, NY 10597
  • /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
  • /31

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 2,909 Sq Ft

    30 Hilltop Rd, Waccabuc, NY 10597

    Welcome to your fully reimagined Dream Home—renovated from top to bottom in 2024 with the help of a seasoned designer and a fresh eye for style. Set on a quiet street in the heart of Northern Westchester, this 4-bedroom, 2.5-bath center hall colonial checks all the boxes for beauty, convenience, and lifestyle.From the moment you enter, you’ll be greeted by a sunlit foyer and a bright, airy

    Melissa Marcogliese Compass Greater NY, LLC

    30 Hilltop Rd, Waccabuc, NY 10597
  • /46

    $1,199,000

    • 3 Beds
    • 3 Baths
    • 3,781 Sq Ft

    8 Roads End Rd, South Salem, NY 10590

    Experience architectural drama and tranquil luxury in this breathtaking contemporary residence, where walls of glass blur the boundary between indoors and out. Perched above the shimmering reservoir at the end of a cul-de-sac, this three-bedroom, three-bathroom home is a bold statement in design, defined by abundant natural light and a seamless connection to nature. The open-concept main living

    Daniel Feldman Julia B Fee Sothebys Int. Rlty

    8 Roads End Rd, South Salem, NY 10590
  • /35

    $1,095,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 3,200 Sq Ft

    13 Laurie Ln, South Salem, NY 10590

    Estate-Style Living on 5 Serene Acres! Discover timeless elegance in this meticulously maintained 3-bedroom, 2.5-bath Center Hall Colonial, privately nestled on a picturesque 5-acre oasis with mature landscaping and custom stonework. This stunning residence offers the perfect blend of classic charm and modern upgrades for true turnkey luxury.Step inside to find sun-drenched living spaces

    Jacqueline Holland-Ruby Berkshire Hathaway HS NY Prop

    13 Laurie Ln, South Salem, NY 10590
  • /44

    $1,049,000

    • 3 Beds
    • 3.5 Baths
    • 3,640 Sq Ft

    161 Goldens Bridge Rd, Katonah, NY 10536

    New York City Tribeca loft meets serene suburban living in this uniquely designed contemporary home, set in the desirable Katonah Ridge community sitting on over 2.4 acres! Perfectly situated just minutes from downtown Katonah, with easy access to the Metro North with a short hour commute to NYC. Privately set back from the road with a long driveway and plenty of space for multiple vehicles, this

    Michael Clemente DeSimone Real Estate

    161 Goldens Bridge Rd, Katonah, NY 10536
  • /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
  • /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
  • /29

    $429,000

    • 2 Beds
    • 1 Bath
    • 1,070 Sq Ft

    52 Bittersweet Ln, South Salem, NY 10590

    Welcome to 52 Bittersweet Lane—a bright and tidy one-level unit in the sought-after Oakridge community, ready for your personal touch. This clean and functional 2-bedroom, 1-bath home offers a fantastic opportunity to update and modernize to your taste, whether you're looking for a fresh start or a smart investment property that you can rent out right away! The layout is simple and convenient,

    Eric Staub Keller Williams NY Realty

    52 Bittersweet Ln, South Salem, NY 10590
  • /22

    $619,000

    • 2 Beds
    • 1 Bath
    • 1,250 Sq Ft

    100 East St, South Salem, NY 10590

    Make Believe Farm. Absolutely adorable Country Farmhouse dating to 1850. Fabulous antique details including wide board wood floors and period millwork. Warm and inviting Living Room with fireplace and built-ins. Country Kitchen and Dining Area with doors to rear terrace for a great indoor-outdoor lifestyle. Second Floor Primary Bedroom with Dressing Room. Charming Second Bedroom with window

    Mary Anne Condon Ginnel Real Estate

    100 East St, 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 custom millwork, steel casement windows, Galbraith & Paul wall coverings and bespoke fixtures and fittings. Beautifully finished Living Room with painted paneling, skylit

    Mindy Weil Ginnel Real Estate

    38 Gilbert St, South Salem, NY 10590
  • /30

    $699,000

    • 3 Beds
    • 1.5 Baths
    • 1,924 Sq Ft

    15 Glen Dr, South Salem, NY 10590

    Step into the serene embrace of this charming Ranch-style home, where comfort meets tranquility on a private one-acre haven. Nicely maintained, this residence boasts central air, hardwood floors, a newer roof, and windows that invite natural light into every corner. The convenience of an attached two-car garage and a walk-out lower level enhances the home’s appeal.As you enter, the warm

    AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

    15 Glen Dr, South Salem, NY 10590
  • /31

    $799,000

    • 4 Beds
    • 2.5 Baths
    • 2,921 Sq Ft

    212 Elmwood Rd, South Salem, NY 10590

    Tucked away on a quiet, wooded lane, this contemporary retreat is all about the setting - private, peaceful, and naturally dramatic. Set against a backdrop of exposed rock formations and mature trees, the backyard is a true sanctuary. Whether you're entertaining on the expansive deck, relaxing in the in-ground pool and jacuzzi, or enjoying a quiet morning coffee surrounded by nature, this outdoor

    Igor Krasnoperov Rising Star Realty

    212 Elmwood Rd, South Salem, NY 10590
  • /33

    $775,000

    • 4 Beds
    • 2.5 Baths
    • 2,650 Sq Ft

    10 Silvermine Dr, South Salem, NY 10590

    Set on a peaceful, dead-end street, this classic Colonial offers a rare blend of privacy, livable space, and natural beauty. Nestled on almost 2 acres with a gently sloping lawn and a seasonal pond view, the setting is quiet and inspiring — ideal for those who value connection to nature without sacrificing convenience. Inside, the home welcomes with hardwood floors throughout, a generous family

    Igor Krasnoperov Rising Star Realty

    10 Silvermine Dr, South Salem, NY 10590
  • /24

    $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
  • /25

    $674,000

    • 4 Beds
    • 3 Baths
    • 1,944 Sq Ft

    25 Twin Lakes Rd, South Salem, NY 10590

    This charming, well-maintained 4 bedroom 3 bath raised ranch is a hidden gem in a highly coveted location with its unique blend of serene lake living and the conveniences to NYC, Ridgefield, Danbury & Stamford, CT. The main level features the kitchen, formal dining room & cozy living room with a fireplace and large picture window that frames the picturesque seasonal views of the lake, front yard

    Mark Boyland Keller Williams Realty Partner

    25 Twin Lakes Rd, South Salem, NY 10590
  • /5

    $750,000

    • Land
    • 9 Acres
    • $82,508 per Acre

    6 Duffys Bridge Rd, Lewisboro, NY 10536

    A rare find at a great price. Spectacular nine acres in desirable Katonah location with approved building plans. Drilled 330' well with 50 gpm and septic installed for four bedroom home. Land cleared for building site. Comes with building plans for 4 bedroom, 3 1/2 5000+sf home.

    Nancy Tuccillo Coldwell Banker Realty

    6 Duffys Bridge Rd, Lewisboro, NY 10536
  • /34

    $590,000

    • 3 Beds
    • 1.5 Baths
    • 2,274 Sq Ft

    29 Quincy Ct, Goldens Bridge, NY 10526

    This well appointed 3 level townhome is FULLY AVAILABLE!. Offering the Wild Oaks community and NO HOA fee's! This is an attached home with a private setting with double decks amid mature trees surrounding it. Inside you will find an abundance of bright natural light shining through this open floor plan with the sun beaming off the gleaming oakwood floors. Just move right in and call it home.

    Randy Calano Keller Williams Realty Partner

    29 Quincy Ct, Goldens Bridge, NY 10526
  • /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
  • /31

    $640,000 Open Sun 12PM - 2PM

    • 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
  • /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
  • /25

    $425,000 Coming Soon

    • 2 Beds
    • 1.5 Baths
    • 1,407 Sq Ft

    71 Fox Run, South Salem, NY 10590

    This lovely 2-bedroom, 2-bath home in the Oakridge Development offers both comfort and versatility. The entryway leads up to a bright and inviting living room with a fireplace that flows seamlessly into the dining area and kitchen, creating a warm and open concept living space. The kitchen features a sliding glass door that opens to a deck perfect for relaxing or entertaining, where you can enjoy

    Mark Boyland Keller Williams Realty Partner

    71 Fox Run, South Salem, NY 10590
  • /27

    $799,000 Coming Soon

    • 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
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