Lewisboro, NY Homes

• 

  Est $254,329 Not Listed For Sale

  22 Fox Run, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 660 Sq Ft
  • Built 1981

  22 Fox Run, South Salem, NY 10590

  Last Sold Summary

  • 21% Above List Price
  • $317/SF
  • 54 Days On Market

  • Last Sold Price $209,532
  • Jul 24, 2024

  Last Listing Agent Christine MacDonald Houlihan Lawrence Inc.
• 

  

  

  /28

  $1,729,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 4,259 Sq Ft

  158 Mead St, Waccabuc, NY 10597

  Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc. Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The

  Amy Smith Sroka Julia B Fee Sothebys Int. Rlty

  158 Mead St, Waccabuc, NY 10597
• 

  $960,000 Sold Mar 02, 2026

  14 Mark Mead Rd, Cross River, NY 10518

  • 3 Beds
  • 2.5 Baths
  • 2,650 Sq Ft
  • Built 1930

  Last Sold Summary

  • 1% Above List Price
  • $362/SF
  • 22 Days On Market

  Current Estimated Value $944,073

  Last Listing Agent Christopher Motta Real Broker NY LLC

  14 Mark Mead Rd, Cross River, NY 10518
• 

  Est $626,069 Not Listed For Sale

  39 Bittersweet Ln, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft
  • Built 1981

  39 Bittersweet Ln, South Salem, NY 10590

  Last Sold Summary

  • 14% Above List Price
  • $292/SF
  • 32 Days On Market

  • Last Sold Price $550,000
  • Feb 29, 2024

  Last Listing Agent Brenda Timm Coldwell Banker Realty
• 

  

  

  /34

  $2,495,000 Pending

  • 5 Beds
  • 4.5 Baths
  • 3,712 Sq Ft

  20 Mead St, Waccabuc, NY 10597

  Set along storied Mead Street in the historic hamlet of Waccabuc, this 19th-century 4BR home, offered for the first time in nearly half a century, is the heart of a 2-acre, park-like property that also includes a 1BR guest cottage, expansive barn/3-car garage, ice house, smokehouse, and woodshed. Built for the Hunt Family in 1809 (with subsequent additions over time), the Federal-style Colonial

  Susan Stillman Houlihan Lawrence Inc.

  20 Mead St, Waccabuc, NY 10597
• 

  $1,137,000 Sold Sep 15, 2025

  30 Benedict Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 2,400 Sq Ft
  • Built 1960

  Last Sold Summary

  • 14% Above List Price
  • $474/SF
  • 35 Days On Market

  Current Estimated Value $1,148,660

  Last Listing Agent Margaret Harrington Douglas Elliman Real Estate

  30 Benedict Rd, South Salem, NY 10590
• 

  Est $983,217 Not Listed For Sale

  38 Lockwood Rd, South Salem, NY 10590

  • 3 Beds
  • 3.5 Baths
  • 2,478 Sq Ft
  • Built 1977

  38 Lockwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 19% Above List Price
  • $333/SF
  • 30 Days On Market

  • Last Sold Price $825,000
  • Aug 22, 2023

  Last Listing Agent Geraldine Brucale BHHS Hudson Valley Properties
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  /34

  $599,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,308 Sq Ft

  39 Park Rd, Goldens Bridge, NY 10526

  Sophisticated, beautifully renovated 2-bedroom, 2-bath semi-attached residence in the highly desirable Wild Oaks community, offering breathtaking sunset and serene wooded views with an expansive private backyard. This light-filled, move-in ready home combines timeless elegance with modern upgrades in a peaceful, natural setting.The interior showcases rich hardwood floors, crown moldings, and

  Teresa Chang Houlihan Lawrence Inc.

  39 Park Rd, Goldens Bridge, NY 10526
• 

  $872,000 Sold Oct 23, 2025

  187 Todd Rd, Katonah, NY 10536

  • 3 Beds
  • 2 Baths
  • 1,851 Sq Ft
  • Built 1939

  Last Sold Summary

  • 21% Above List Price
  • $471/SF
  • 14 Days On Market

  Current Estimated Value $887,820

  Last Listing Agent Ellen Schwartz Julia B Fee Sothebys Int. Rlty

  187 Todd Rd, Katonah, NY 10536
• 

  Est $983,493 Not Listed For Sale

  235 Elmwood Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,592 Sq Ft
  • Built 1975

  235 Elmwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 19% Above List Price
  • $318/SF
  • 7 Days On Market

  • Last Sold Price $825,000
  • Sep 19, 2023

  Last Listing Agent Joann Galluccio William Raveis-New York LLC
• 

  

  /47

  $759,000

  • 3 Beds
  • 2.5 Baths
  • 2,200 Sq Ft

  34 Glen Dr, South Salem, NY 10590

  A Sprawling 2.68 Acre Haven with Majestic Rock Gardens! Discover this beautiful, private Ranch-style home nestled on 2.68 tranquil acres. This property offers a perfect blend of peaceful seclusion and versatile living spaces, all surrounded by stunning, mature landscaping. Exquisite Outdoor Sanctuary. The expansive, professionally landscaped grounds feature mature plantings, majestic rock

  AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

  34 Glen Dr, South Salem, NY 10590
• 

  $710,000 Sold Oct 07, 2025

  15 Glen Dr, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 1,924 Sq Ft
  • Built 1964

  Last Sold Summary

  • 2% Above List Price
  • $369/SF
  • 31 Days On Market

  Current Estimated Value $726,521

  Last Listing Agent AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

  15 Glen Dr, South Salem, NY 10590
• 

  Est $836,236 Not Listed For Sale

  11 Lorraine Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,332 Sq Ft
  • Built 1970

  11 Lorraine Rd, South Salem, NY 10590

  Last Sold Summary

  • 4% Above List Price
  • $606/SF
  • 15 Days On Market

  • Last Sold Price $807,000
  • Jan 05, 2024

  Last Listing Agent Mark Boyland Keller Williams Realty Partner
• 

  

  /25

  $139,000 Pending

  • 1 Bed
  • 1 Bath
  • 700 Sq Ft

  10 Wild Oaks Rd Unit 103, Goldens Bridge, NY 10526

  Welcome to Cedar Woods in Goldens Bridge, nestled within the highly sought-after Katonah-Lewisboro School District. This prime location offers exceptional accessibility to Metro-North stations, I-684, and the Goldens Bridge shopping center. This no-step, first-floor 1-bedroom unit provides the convenience of one-floor living, featuring a private terrace off the bedroom and easy access to common

  Carine Nowak Compass Greater NY, LLC

  10 Wild Oaks Rd Unit 103, Goldens Bridge, NY 10526
• 

  $1,200,000 Sold Jun 20, 2025

  94 Bouton Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,623 Sq Ft
  • Built 1790

  Last Sold Summary

  • 9% Above List Price
  • $457/SF
  • 8 Days On Market

  Current Estimated Value $1,231,453

  Last Listing Agent Cecilia Heller Houlihan Lawrence Inc.

  94 Bouton Rd, South Salem, NY 10590
• 

  Est $801,363 Not Listed For Sale

  464 Smith Ridge Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 3,371 Sq Ft
  • Built 1900

  464 Smith Ridge Rd, South Salem, NY 10590

  Last Sold Summary

  • 32% Above List Price
  • $179/SF
  • 68 Days On Market

  • Last Sold Price $605,000
  • Jun 27, 2024

  Last Listing Agent Hua Bin Chen Liberty Chateau Realty Inc
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  /45

  $949,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,120 Sq Ft

  11 Billingsley Trail, Goldens Bridge, NY 10526

  A beautifully maintained and updated home offering 3 bedrooms and 3 bathrooms plus an office situated on lower level near full bathroom making it ideal for a guest/4th bedroom. This brick & cedar shake exterior home is set beautifully on one acre of property, located on a quiet cul-de-sac, offering amazing privacy with level back yard. A unique split-level home features a stunning sunroom

  Bill Reilly Billingsley Realty

  11 Billingsley Trail, Goldens Bridge, NY 10526
• 

  $1,900,000 Sold Oct 01, 2025

  121 Post Office Rd, South Salem, NY 10590

  • 3 Beds
  • 1.5 Baths
  • 3,307 Sq Ft
  • Built 1792

  Last Sold Summary

  • 6% Above List Price
  • $575/SF
  • 33 Days On Market

  Current Estimated Value $1,885,523

  Last Listing Agent Jennie Doukas Ginnel Real Estate

  121 Post Office Rd, South Salem, NY 10590
• 

  Est $1,090,508 Not Listed For Sale

  42 West Rd, South Salem, NY 10590

  • 3 Beds
  • 3 Baths
  • 2,656 Sq Ft
  • Built 1948

  42 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 1% Above List Price
  • $405/SF
  • 21 Days On Market

  • Last Sold Price $1,075,000
  • Dec 17, 2024

  Last Listing Agent Lawler Parker Douglas Elliman Real Estate
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  /39

  $4,200,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 5,644 Sq Ft

  11 Carriage House Rd, Waccabuc, NY 10597

  Set at the tip of the Waccabuc Country Club and bordering the wildflower fields of a protected nature preserve, this enchanting Shingled Hampton-style home (built in 1940) is at once hidden, private, and extraordinary. Offering 5,644 sq. ft., the home currently lives as a 3-bedroom but can easily transform into a 4-bedroom layout. A curved formal entry with wood paneling, high ceilings, and brick

  Melissa Marcogliese Compass Greater NY, LLC

  11 Carriage House Rd, Waccabuc, NY 10597
• 

  $675,000 Sold Oct 15, 2025

  25 Twin Lakes Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 1,944 Sq Ft
  • Built 1964

  Last Sold Summary

  • 3% Below List Price
  • $347/SF
  • 49 Days On Market

  Current Estimated Value $855,839

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  25 Twin Lakes Rd, South Salem, NY 10590
• 

  Est $746,657 Not Listed For Sale

  35 West Rd, South Salem, NY 10590

  • 3 Beds
  • 2.5 Baths
  • 2,052 Sq Ft
  • Built 1979

  35 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 18% Above List Price
  • $308/SF
  • 16 Days On Market

  • Last Sold Price $631,000
  • Aug 19, 2024

  Last Listing Agent Carol Court Howard Hanna Rand Realty
• 

  

  /39

  $1,250,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 3,522 Sq Ft

  6 Orchard Dr, South Salem, NY 10590

  LAKE COMMUNITY SOPHISTICATION. An exceptional opportunity within the deeded Twin Lakes Village. Perfectly positioned on a private, level half-acre, this home offers a premier lifestyle with exclusive lake privileges and access to a private community beachfront, boat launch, and docks. A masterfully maintained Country Colonial featuring airy, sun-filled spaces and an open floor plan designed for

  Colleen Hickey Giner Real Estate Inc.

  6 Orchard Dr, South Salem, NY 10590
• 

  $1,254,000 Sold Dec 08, 2025

  9 Ashwood Rd, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 3,688 Sq Ft
  • Built 1997

  Last Sold Summary

  • 3% Below List Price
  • $340/SF
  • 27 Days On Market

  Current Estimated Value $1,275,597

  Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

  9 Ashwood Rd, South Salem, NY 10590
• 

  Est $1,235,509 Not Listed For Sale

  25 West Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 3,231 Sq Ft
  • Built 1983

  25 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 3% Above List Price
  • $371/SF
  • 11 Days On Market

  • Last Sold Price $1,200,000
  • Aug 09, 2024

  Last Listing Agent Luke Joachim Redfin Real Estate
• 

  

  /29

  $749,000 Pending

  • 4 Beds
  • 2.5 Baths
  • 2,227 Sq Ft

  50 West Rd, South Salem, NY 10590

  Set on a picturesque 2-acre level lot in South Salem, this charming ranch offers the perfect opportunity to create your dream home. Designed for easy one-level living, this house features 4 Bedrooms including a primary bedroom with en-suite bathroom. While this home is in South Salem, it borders New Canaan, Ridgefield and Pound Ridge and is within the highly regarded Katonah-Lewisboro School

  Gina Cooney Giner Real Estate Inc.

  50 West Rd, South Salem, NY 10590
• 

  $711,000 Sold Jul 21, 2025

  24 Benedict Rd, South Salem, NY 10590

  • 4 Beds
  • 2 Baths
  • 1,846 Sq Ft
  • Built 1955

  Last Sold Summary

  • 5% Below List Price
  • $385/SF
  • 89 Days On Market

  Current Estimated Value $762,628

  Last Listing Agent Cecilia Heller Houlihan Lawrence Inc.

  24 Benedict Rd, South Salem, NY 10590
• 

  Est $1,354,855 Not Listed For Sale

  23 West Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 3,227 Sq Ft
  • Built 1998

  23 West Rd, South Salem, NY 10590

  Last Sold Summary

  • 2% Above List Price
  • $411/SF
  • 17 Days On Market

  • Last Sold Price $1,325,000
  • Apr 10, 2025

  Last Listing Agent Luke Joachim Redfin Real Estate
• 

  

  /14

  $685,000

  • 3 Beds
  • 2.5 Baths
  • 1,862 Sq Ft

  23 Bouton St, South Salem, NY 10590

  Highest and best offers due 4/8/26 Accepted Offer 4/8multiple backupsNew professional photos!! — this property is no longer limited to cash buyers. Qualified purchasers may obtain financing with proper documentation, making this an even more accessible and attractive opportunity. The main level features an open-concept layout highlighted by a large bay window that fills the space with

  Blaise Nastasio Manhattan Network Inc

  23 Bouton St, South Salem, NY 10590
• 

  $560,000 Sold May 15, 2025

  86 Locust Ridge, Cross River, NY 10518

  • 1 Bed
  • 1.5 Baths
  • 1,451 Sq Ft
  • Built 1986

  Last Sold Summary

  • 7% Above List Price
  • $386/SF
  • 10 Days On Market

  Current Estimated Value $561,106

  Last Listing Agent Shaiju Kalathil SK Landmarks LLC

  86 Locust Ridge, Cross River, NY 10518
• 

  Est $1,053,311 Not Listed For Sale

  12 Douglas Dr, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,755 Sq Ft
  • Built 1982

  12 Douglas Dr, South Salem, NY 10590

  Last Sold Summary

  • 11% Above List Price
  • $345/SF
  • 46 Days On Market

  • Last Sold Price $950,000
  • Oct 18, 2024

  Last Listing Agent John Nigro Keller Williams Prestige Prop
• 

  

  /29

  $1,695,000

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

  58 Twin Lakes Rd, South Salem, NY 10590

  Set along the shoreline of Lake Oscaleta, this direct waterfront home offers a rare combination of privacy, natural beauty, and truly usable lakefront property in the heart of South Salem. Occupying .564 acres with sweeping frontage on one of the area’s most peaceful glacial lakes, the setting is defined by something increasingly hard to find - an expansive, level lawn that extends all the way to

  Adam Hade Compass Greater NY, LLC

  58 Twin Lakes Rd, South Salem, NY 10590
• 

  $890,000 Sold Jun 24, 2025

  16 Gilbert St, South Salem, NY 10590

  • 4 Beds
  • 1.5 Baths
  • 1,396 Sq Ft
  • Built 1928

  Last Sold Summary

  • 6% Below List Price
  • $638/SF
  • 239 Days On Market

  Current Estimated Value $908,205

  Last Listing Agent Donna Ornstein William Raveis-New York LLC

  16 Gilbert St, South Salem, NY 10590
• 

  Est $891,008 Not Listed For Sale

  20 Glen Dr, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 1,823 Sq Ft
  • Built 1964

  20 Glen Dr, South Salem, NY 10590

  Last Sold Summary

  • 1% Below List Price
  • $494/SF
  • 12 Days On Market

  • Last Sold Price $900,000
  • May 29, 2024

  Last Listing Agent AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty
• 

  

  /43

  $725,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  453 Smith Ridge Rd, South Salem, NY 10590

  Welcome to your own private sanctuary—a meticulously maintained and thoughtfully updated home. Featuring a 1,620-square-foot retreat where nature meets elegance at every turn. Built in 1946 and lovingly cared for, this exceptional South Salem property offers the rare combination of tranquil seclusion and premier location in the sought-after Katonah-Lewisboro school district. A fabulous setting

  AnnMarie Sementilli Julia B Fee Sothebys Int. Rlty

  453 Smith Ridge Rd, South Salem, NY 10590
• 

  $725,000 Sold Apr 20, 2026

  256 Smith Ridge Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 2,682 Sq Ft
  • Built 1983

  Last Sold Summary

  • 9% Below List Price
  • $270/SF
  • 10 Days On Market

  Current Estimated Value $803,620

  Last Listing Agent Erin Lee Keller Williams Realty Group

  256 Smith Ridge Rd, South Salem, NY 10590
• 

  Est $927,410 Not Listed For Sale

  7 Laurel Rd, South Salem, NY 10590

  • 3 Beds
  • 3.5 Baths
  • 2,675 Sq Ft
  • Built 1978

  7 Laurel Rd, South Salem, NY 10590

  Last Sold Summary

  • 11% Above List Price
  • $313/SF
  • 59 Days On Market

  • Last Sold Price $837,500
  • Mar 06, 2025

  Last Listing Agent Brenda Timm Coldwell Banker Realty
• 

  

  /50

  $4,850,000

  • 4 Beds
  • 4.5 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, 4.5-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
• 

  $419,500 Sold Nov 04, 2025

  144 Stone Meadow, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 1,112 Sq Ft
  • Built 1982

  Last Sold Summary

  • 7% Below List Price
  • $377/SF
  • 22 Days On Market

  Current Estimated Value $419,425

  Last Listing Agent Lindsay Lafreniere William Raveis-New York LLC

  144 Stone Meadow, South Salem, NY 10590
• 

  Est $938,650 Not Listed For Sale

  14 Laurel Rd, South Salem, NY 10590

  • 4 Beds
  • 3 Baths
  • 2,435 Sq Ft
  • Built 1977

  14 Laurel Rd, South Salem, NY 10590

  Last Sold Summary

  • 7% Above List Price
  • $359/SF
  • 70 Days On Market

  • Last Sold Price $875,000
  • Jan 06, 2025

  Last Listing Agent Melissa Frank Lutz Douglas Elliman Real Estate

Showing Results 121 - 160, Page 4 of 18