20

Lewisboro, NY Homes for Sale with Acreage

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  • /38

    $669,900

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

    48 Lockwood Rd, South Salem, NY 10590

    A/O AS PER JULY 28/2025Elegance & 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 locations—just minutes from top-rated schools, charming shops, dining, and

    Agent Photo

    Pino Masucci

    River Realty Services, Inc.

    (914) 785-6711

    48 Lockwood Rd, 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
  • /50

    $1,100,000

    • 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
  • /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
  • /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
  • /35

    $1,095,000

    • 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
  • /32

    $899,000 Open Sun 1PM - 3PM

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

    9 Upland Ct, South Salem, NY 10590

    Classic Country Colonial. At the end of a desirable cul-de-sac. Beautifully maintained 3200 square feet of sun-filled living space. Perfectly proportioned rooms with oversized windows to capture natural light. Center Entrance Hall. Spacious Living and Dining Rooms for formal entertaining. Well-designed Country Kitchen with Breakfast Area. Heart-of-the-home Family Room with fireplace for casual

    Mary Anne Condon Ginnel Real Estate

    9 Upland Ct, 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
  • /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
  • /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
  • /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

    $725,000

    • 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
  • /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
  • /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
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