23

Lewisboro, NY Homes for Sale

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  • /26

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

    • 4 Beds
    • 2 Baths
    • 2,040 Sq Ft

    34 Old Bedford Rd, Goldens Bridge, NY 10526

    Check out the 360 tour for this truly rare opportunity in the heart of Goldens Bridge—a fully vacant, two-family home ideal for multigenerational living or generating rental income. Nestled on nearly an acre of level land, this charming brick duplex offers flexibility, privacy, and unbeatable convenience. Whether you're looking to keep loved ones close or build your investment portfolio, this

    John Lajara eXp Realty

    34 Old Bedford Rd, Goldens Bridge, NY 10526
  • /20

    $1,749,000 Open Sat 1PM - 3PM

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

    69 Mead St, Waccabuc, NY 10597

    Wonderful custom built contemporary home in the heart of historic Waccabuc! Sited on over 4 acres of meticulously landscaped grounds along desirable Mead Street, this exceptional home offers the perfect blend of privacy and convenience. Thoughtfully designed and beautifully maintained, it’s a true retreat just minutes from every convenience. Features 4 bedrooms including a spacious

    Cheryl Neuburger Ginnel Real Estate

    69 Mead St, Waccabuc, NY 10597
  • /31

    $1,389,000 Open Sat 12:30PM - 2:30PM

    • 4 Beds
    • 4.5 Baths
    • 3,192 Sq Ft

    7 Hilltop Rd, Waccabuc, NY 10597

    Waccabuc: Nestled on two picturesque acres, this elegant 4-bedroom Colonial offers timeless charm and modern comfort in a serene, private setting minutes from local amenities. Step inside to a welcoming foyer opening to a warm and inviting living room with fireplace, ideal for relaxing evenings or entertaining guests. Across the hall, the spacious family room also boasts a fireplace, creating a

    Rita Carrozza

    7 Hilltop Rd, Waccabuc, NY 10597
  • /39

    $1,225,000

    • 2 Beds
    • 3 Baths
    • 1,940 Sq Ft

    21 Lake Shore Dr, South Salem, NY 10590

    On the serene shores of Lake Truesdale in South Salem sits Blackbird Cottage, an utterly charming two-bedroom that truly lives like a three. Built in 2020, the home still feels brand new inside. Step into a light-filled entry and continue into a spacious open living area. The stylish kitchen features a center island and chef’s appliances, while the adjacent dining area is a magical retreat

    Melissa Marcogliese Compass Greater NY, LLC

    21 Lake Shore Dr, South Salem, NY 10590
  • /40

    $1,595,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 3.5 Baths
    • 3,532 Sq Ft

    230 Spring St, South Salem, NY 10590

    Welcome home to this exquisitely crafted and meticulously maintained colonial, perfectly set on 9 acres of serene natural beauty—offering the comfort, elegance, and charm you’ve been searching for!Step through the grand mahogany doors and discover a spacious living room with a cozy fireplace, an elegant dining room ideal for holiday gatherings, and a stunning French Country kitchen with a

    Kristina Pepdjonovic Julia B Fee Sothebys Int. Rlty

    230 Spring St, South Salem, NY 10590
  • /38

    $1,299,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 3.5 Baths
    • 3,688 Sq Ft

    9 Ashwood Rd, South Salem, NY 10590

    Tucked away on a peaceful cul-de-sac, a long, tree-lined driveway sets the tone as you approach this 4-bedroom, 3.5-bath colonial set on 4 private acres in the award-winning Katonah-Lewisboro School District. This home offers a welcoming front porch, a 3-car garage, and an ideal blend of space, comfort, and privacy. The main level features a large kitchen opening to an expansive family room with

    Lindsay Lafreniere William Raveis-New York LLC

    9 Ashwood Rd, South Salem, NY 10590
  • /23

    $2,295,000 Open Sun 2AM - 4PM

    • 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
  • /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
  • /50

    $1,875,000

    • 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
  • /39

    $1,995,000 Coming Soon

    • 4 Beds
    • 3.5 Baths
    • 2,688 Sq Ft

    15 Reyburn Rd, Katonah, NY 10536

    An extraordinary compound just minutes from downtown Katonah this 4.1-acre estate is comprised of a fully renovated 4 bedroom stone farmhouse, a guest cottage, 2 car garage plus 3rd bay, a storage barn, pool and beautiful expansive property with winter reservoir views. The main residence offers light-filled interiors, custom millwork, a gourmet chef’s kitchen, renovated spa-inspired bathrooms,

    Melissa Frank Lutz Douglas Elliman Real Estate

    15 Reyburn Rd, Katonah, NY 10536
  • /36

    $610,000 Open Sat 12PM - 2PM

    • 2 Beds
    • 2.5 Baths
    • 1,810 Sq Ft

    124 Woodcock Knolls, Cross River, NY 10518

    A Gem!! A rare opportunity awaits in this highly coveted end-unit home, offering exceptional privacy, great living spaces, and thoughtful upgrades throughout. Step outside to an expansive private deck with steps down to lawn, perfect for morning coffee or alfresco dining. This townhome is designed for modern living, featuring an attached garage along with a parking spot (3 spaces to park

    Eileen McGrath Douglas Elliman Real Estate

    124 Woodcock Knolls, Cross River, NY 10518
  • /19

    $769,000 Open Sat 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,596 Sq Ft

    40 Lakeview Pass, Katonah, NY 10536

    Lake Katonah living! Move right in to this vibrant lake community. First floor primary bedroom w/bath and 2 additional bedrooms w/ hall bath on the main floor. Living room features a cozy fireplace. Beautifully updated kitchen with quartz counters and stainless appliances. Fabulous great room with tons of natural light, hardwood floors and vaulted ceilings on main floor. Lower level

    Cheryl Neuburger Ginnel Real Estate

    40 Lakeview Pass, Katonah, NY 10536
  • /37

    $950,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 3,031 Sq Ft

    134 Spring St, South Salem, NY 10590

    "The Rockwell House: circa 1794. Meticulously maintained Center-Hall Colonial w/large rooms and family floor plan + two outbuildings. Revolutionary-era architecture w/distinctive design features. Wide plank wood floors, period woodwork, detailed moldings, and 3 working fireplaces. Den/Office has a separate entry ideal for home office for those who need privacy while working from home. Stainless

    Donna Ornstein William Raveis-New York LLC

    134 Spring St, South Salem, NY 10590
  • /30

    $1,475,000

    • 4 Beds
    • 3.5 Baths
    • 3,463 Sq Ft

    7 Douglas Dr, South Salem, NY 10590

    New to the market! This four bedroom, Colonial Farmhouse with a rocking chair porch features a classic layout of rooms. There is a private and quiet, newly built in-ground pool with a large built-in shelf for sunbathing/ kids/ pets and an electric cover. The pool is dramatically sited among large natural rocks. Vintage wide board flooring reclaimed from an antique Virginia barn is

    Sally Slater Douglas Elliman Real Estate

    7 Douglas Dr, South Salem, NY 10590
  • /39

    $1,195,000

    • 5 Beds
    • 2.5 Baths
    • 3,217 Sq Ft

    10 Mark Mead Rd, Cross River, NY 10518

    Lovely 5 bedroom, 2.1 bath Cape Cod style home. Very spacious rooms! Large updated eat in kitchen, large living room with fireplace and door out to deck. Spacious dining room for entertaining! The home is 3,217 sq ft with an additional 540 sq ft of finished space in the basement that is not included in the living space. Pretty, level land with separate 2 car garage. Very private yet convenient

    Karen Burchetta Houlihan Lawrence Inc.

    10 Mark Mead Rd, Cross River, NY 10518
  • /24

    $439,000

    • 1 Bed
    • 1 Bath
    • 1,112 Sq Ft

    144 Stone Meadow, South Salem, NY 10590

    Tucked away in the peaceful and well-loved Oakridge community, this beautifully renovated 1-bedroom condo with a versatile loft/bonus room offers more than just a place to live — it offers a lifestyle. From the moment you step inside, you'll notice the attention to detail and thoughtful upgrades that set this home apart. The newly renovated kitchen with custom cabinetry is a true centerpiece,

    Lindsay Lafreniere William Raveis-New York LLC

    144 Stone Meadow, South Salem, NY 10590
  • /21

    $479,000

    • 3 Beds
    • 2 Baths
    • 1,296 Sq Ft

    30 Fairmount Rd, Goldens Bridge, NY 10526

    Welcome to Wild Oaks neighborhood in Goldens Bridge with Katonah-Lewisboro schools. This lovely end-unit attached single-family home offers 3 bedrooms, 2 full baths, open dining room and living room with fireplace plus a spacious backyard for entertaining family and friends. The inviting rooms are filled with natural light, recessed lighting and hardwood floors on the main level. The flexible

    Maria LaGattuta Douglas Elliman Real Estate

    30 Fairmount Rd, Goldens Bridge, NY 10526
  • /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
  • /36

    $549,000 Open Sun 12PM - 2PM

    • 1 Bed
    • 1.5 Baths
    • 1,941 Sq Ft

    58 Winterberry Cir, Cross River, NY 10518

    **Price Reduction at The MEADOWS!**Don’t miss the chance to own 58 Winterberry Circle, a stunning townhouse boasting 1,941 sq ft of desirable living space, strategically located near the activity center. As you enter the townhouse, you’re greeted by a welcoming foyer that seamlessly transitions into a flexible area perfect for a family/guest room, home office or gym.The main level

    Carine Nowak Compass Greater NY, LLC

    58 Winterberry Cir, Cross River, NY 10518
  • /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
  • /5

    $750,000

    • Land
    • 9.09 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
  • /47

    $689,000 Coming Soon

    • 2 Beds
    • 2 Baths
    • 1,299 Sq Ft

    64 Ridgeland Rd, South Salem, NY 10590

    Welcome to Lake Kitchawan! This charming cottage offers surprising privacy and winter lake views. The first floor offers a Garden Room entry with 3 sets of French doors leading to the Living Room with a fireplace. There is a first-floor bedroom (currently used as a den and guest room) with sliders to the deck, a full bath, and another full bath with a French door to the expansive

    James Avery Coldwell Banker Realty

    64 Ridgeland Rd, South Salem, NY 10590
  • /39

    $3,250,000 Coming Soon

    • 4 Beds
    • 4.5 Baths
    • 5,575 Sq Ft

    127 Boutonville Rd, Pound Ridge, NY 10576

    Sophisticated & Serene. The perfect country retreat. Over eight, peaceful acres along a desirable country road. Gated drive to private oasis with gorgeous plantings, three ponds, rolling lawns and woodland walking paths. Infinity edge salt-water swimming pool with spa and your own tennis court. Meticulous stone and shingle Country House with 5500 square feet of sun-filled living space. Fabulous

    Mary Anne Condon Ginnel Real Estate

    127 Boutonville Rd, Pound Ridge, NY 10576

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 ...

Frequently Asked Questions

What are the most popular zip codes in Lewisboro, NY?
The most popular zip codes in Lewisboro, NY include 10576, 10518, 10597, 10590 and 10536.
How are the schools in Lewisboro, NY?
Lewisboro, NY has highly rated public and private schools. Some of the best schools in Lewisboro based on Niche Grades are East Elementary School, New Canaan High School and Ridgefield High School. Browse all the schools in Lewisboro, NY to learn more.
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