17

Lewisboro, NY Homes for Sale

Section Image
  • /36

    $2,950,000

    • 6 Beds
    • 5.5 Baths
    • 6,344 Sq Ft

    133 Boway Rd, South Salem, NY 10590

    The Quintessential Getaway. Long, gated drive through spectacular grounds to ultimate privacy and seclusion. Twenty glorious acres with level lawns, ancient trees, ornamental shrubs and flowering perennials. Fenced grounds with woodland walking trails throughout. Absolutely breathtaking backdrop for the perfect country lifestyle. Fabulous raised terrace overlooking the stunning swimming pool.

    Mary Anne Condon Ginnel Real Estate

    133 Boway Rd, South Salem, NY 10590
  • /36

    $1,999,999

    • 5 Beds
    • 4.5 Baths
    • 5,031 Sq Ft

    20 Waccabuc River Ln, South Salem, NY 10590

    This five bedroom modern farmhouse blends timeless charm with a sleek contemporary interior, sitting privately on nearly 6 acres with expansive distant views. The property provides a serene outdoor retreat with a sparkling gunite pool, a covered deck for effortless entertaining, open green space and lush, landscaped gardens. Perfectly positioned within the Katonah Lewisboro School District, it

    Patti Howard Compass Greater NY, LLC

    20 Waccabuc River Ln, South Salem, NY 10590
  • /13

    $1,650,000

    • 4 Beds
    • 2 Baths
    • 1,800 Sq Ft

    114 Spring St, South Salem, NY 10590

    Parcel of 4 Properties: Deli plus 2 Family House, 4 bedroom house w/detached garage. Located in the Hamlet Of South Salem, Surrounded By Green Space. The property is 100% leased. One Car Garage, Lots Of Parking. Super Location. Acreage and Taxes reflect both 112 & 114 Spring Street addresses. Additional Information: HeatingFuel:Oil Above Ground,ParkingFeatures:1 Car Detached

    Matt Rose Keller Williams Prestige Prop

    114 Spring St, South Salem, NY 10590
  • /39

    $2,295,000

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

    50 Cove Rd, South Salem, NY 10590

    Set on the coveted waters of Lake Waccabuc, one of Northern Westchester’s most private and prestigious lakes, is a rare offering that blends architectural history with refined modern comfort. Originally crafted in 1939, the home was constructed of hand-cut Millstone granite and warm knotty pine paneling, a testament to old-world artistry and enduring character. The vaulted great room, with its

    Cate Hegarty Compass Greater NY, LLC

    50 Cove Rd, South Salem, NY 10590
  • /42

    $2,700,000

    • 6 Beds
    • 7.5 Baths
    • 8,900 Sq Ft

    11 Lost Nations Rd, Pound Ridge, NY 10576

    Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of

    Nikki McMann William Raveis-New York LLC

    11 Lost Nations Rd, Pound Ridge, NY 10576
  • /50

    $1,750,000

    • 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
  • /49

    $3,150,000

    • 4 Beds
    • 3.5 Baths
    • 5,000 Sq Ft

    12 Bishop Park Rd, Pound Ridge, NY 10576

    Generational Compound with all the luxuries & amenities one desires. Cascading pool with waterfall spa, guest house, pond, gardens and private property. Set down a quiet lane this resort-style estate is prime living-just one hour from NYC. A tranquil place to call home for the discerning buyer who can spot special custom home. A thoughtful and tasteful full renovation was completed in 2013. The

    Michael Kaplan Michael J. Kaplan

    12 Bishop Park Rd, Pound Ridge, NY 10576
  • /38

    $650,000

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

    10 Guilford Cir, Goldens Bridge, NY 10526

    Rare opportunity in desirable Katonah Close in Goldens Bridge—units here seldom come to market, so don’t miss this one. This bright, tri-level contemporary end-unit townhome offers space, privacy, and convenient living.The main level welcomes you with a two-story entry, hardwood floors and recessed lighting. Very spacious rooms throughout. Enjoy a large eat-in kitchen with a peninsula, formal

    Debra DeMelis Coldwell Banker Realty

    10 Guilford Cir, Goldens Bridge, NY 10526
  • /32

    $1,275,000

    • 4 Beds
    • 2.5 Baths
    • 2,895 Sq Ft

    288 Todd Rd, Katonah, NY 10536

    Set on 4.12 picturesque acres, this beautifully maintained 4-bedroom Colonial is a rare find. The home offers an open floor plan with sun-filled living and dining rooms, a welcoming family room with a white-washed brick fireplace, and a gorgeous newly renovated eat-in kitchen that opens to an expansive deck—ideal for fun gatherings and unforgettable sunsets. A private bonus room over the garage

    Suzanne Bowers Corcoran Legends Realty

    288 Todd Rd, Katonah, NY 10536
  • /50

    $5,450,000

    • 4 Beds
    • 3.5 Baths
    • 6,161 Sq Ft

    45 Pine Hill Dr, South Salem, NY 10590

    Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 3.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for

    Joseph Lukic Compass Greater NY, LLC

    45 Pine Hill Dr, South Salem, NY 10590
  • /16

    $385,000

    • 1 Bed
    • 1 Bath
    • 971 Sq Ft

    239 Deer Hill, South Salem, NY 10590

    Welcome to 239 Deer Hill Road in Oakridge Condominiums. This top-floor 1-bedroom, 1-bath unit offers 1,000 square feet of updated, turn-key living with low taxes and access to the sought-after Katonah-Lewisboro School District (Meadow Pond Elementary). Recent upgrades include newer appliances, refreshed flooring, and a sleek modern bathroom. The main level features a bright living room with a

    Cate Hegarty Compass Greater NY, LLC

    239 Deer Hill, South Salem, NY 10590
  • /14

    $595,000

    • 1 Bed
    • 1 Bath
    • 776 Sq Ft

    10 Skytop Dr, Katonah, NY 10536

    Live the Katonah lake life in this absolutely charming, fully renovated cottage. A huge stone fireplace and cathedral ceiling are the focal points of this gem which has beautiful hardwood floors and a great kitchen and bath as well. Relax and watch the world go by from the expansive, picturesque rocking chair front porch and enjoy the lovely backyard for great outdoor living. Walk to the lake to

    Angela Kessel Houlihan Lawrence Inc.

    10 Skytop Dr, Katonah, NY 10536
  • /36

    $1,063,125

    • 6 Beds
    • 2 Baths
    • 6,038 Sq Ft

    175 Waccabuc Rd, Goldens Bridge, NY 10526

    1827 Greek Revival Colonial with many of the period features. 3 levels with an additional finished attic and full basement with wine cellar. 5.42 acres with the remnants of the original mill pond and saw mill, lots of granite stone work, wrought iron fencing and root cellar. Over 6000 square feet of living space, 15 rooms, 6 bedrooms and multiple fireplaces. This pre-Civil War property known as

    James Bergstraser RE/MAX Classic Realty

    175 Waccabuc Rd, Goldens Bridge, NY 10526
  • /31

    $425,000

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

    156 Stone Meadow Unit 16156, South Salem, NY 10590

    Discover effortless luxury in this beautifully updated South Salem condominium—a perfect fusion of modern convenience and residential warmth.Step into the welcoming living room where a charming fireplace sets the stage for intimate evenings or gracious entertaining. The thoughtfully designed layout features a generously proportioned bedroom and a versatile loft space that adapts to your

    AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

    156 Stone Meadow Unit 16156, South Salem, NY 10590
  • /2

    $619,000

    • 3 Beds
    • 3 Baths
    • 2,100 Sq Ft

    1203 Old Post Rd, South Salem, NY 10590

    Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our Appraisal describe the property as a SFR (colonial) built in 1980. It has a GLA of approx. 2100 and has 3 bedrooms and

    Christopher Rose REALHome Services & Solutions

    1203 Old Post Rd, South Salem, NY 10590
  • /23

    $1,295,000 Open Sun 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,476 Sq Ft

    12 Skytop Dr, Katonah, NY 10536

    Live the Lake Katonah life in this spacious, fully renovated mid-century modern with incredible views. This house embraces open concept living at its best. The great room has direct access out to the spectacular screened porch from both the living and dining rooms and a brand new deck is directly off of the huge eat-in-kitchen. Enjoy the lovely level backyard for great outdoor activities. Walk to

    Angela Kessel Houlihan Lawrence Inc.

    12 Skytop Dr, Katonah, NY 10536
  • /15

    $765,000

    • Land
    • 1.04 Acres
    • $735,577 per Acre

    Lot 4 Lockwood Rd, Lewisboro, NY 10590

    Lot 4 at Silvermine Preserve offers a rare opportunity to build a sophisticated home in a thoughtfully designed subdivision in South Salem. Enter the community via a picturesque country lane with Belgium block detailing, leading to a private cul-de-sac. Underground utilities. This beautiful homesite is framed by old stone walls, a split rail fence, and mature trees. Part of an approved 13-lot

    Michael Neeley William Raveis-New York LLC

    Lot 4 Lockwood Rd, Lewisboro, 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 ...

Frequently Asked Questions

What are the most popular zip codes in Lewisboro, NY?
The most popular zip codes in Lewisboro, NY include 10590, 10576, 10536, 10506 and 06877.
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.
How to Buy a Home How to Finance a Home How to Sell a Home