Lewisboro, NY Homes

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  /27

  $1,595,000

  • 3 Beds
  • 3.5 Baths
  • 3,665 Sq Ft

  78 Old Church Ln, Pound Ridge, NY 10576

  Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled

  Jody Rosen Julia B Fee Sothebys Int. Rlty

  78 Old Church Ln, Pound Ridge, NY 10576
• 

  $1,325,000

  Sold Oct 16, 2025

  21 Lake Shore Dr, South Salem, NY 10590

  • 2 Beds
  • 3 Baths
  • 1,940 Sq Ft
  • Built 2020

  Last Sold Summary

  • 8% Above List Price
  • $683/SF
  • 8 Days On Market

  Current Estimated Value $1,340,707

  Last Listing Agent Melissa Marcogliese Compass Greater NY, LLC

  21 Lake Shore Dr, South Salem, NY 10590
• 

  Est $911,585

  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

  • 70 Days On Market
• 

  

  

  /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
• 

  $1,685,000

  Sold May 28, 2026

  9 Comanche Ct, Katonah, NY 10536

  • 4 Beds
  • 3.5 Baths
  • 4,256 Sq Ft
  • Built 1982

  Last Sold Summary

  • 21% Above List Price
  • $396/SF
  • 10 Days On Market

  Current Estimated Value $1,466,125

  Last Listing Agent Wendy Loring William Raveis-New York LLC

  9 Comanche Ct, Katonah, NY 10536
• 

  Est $868,718

  Not Listed For Sale

  11 Lockwood Rd, South Salem, NY 10590

  • 4 Beds
  • 2 Baths
  • 2,114 Sq Ft
  • Built 1958

  11 Lockwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 11 Days On Market
• 

  

  /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
• 

  $985,000

  Sold Dec 08, 2025

  10 Mark Mead Rd, Cross River, NY 10518

  • 5 Beds
  • 2.5 Baths
  • 3,217 Sq Ft
  • Built 1965

  Last Sold Summary

  • 18% Below List Price
  • $306/SF
  • 49 Days On Market

  Current Estimated Value $999,058

  Last Listing Agent Karen Burchetta Houlihan Lawrence Inc.

  10 Mark Mead Rd, Cross River, NY 10518
• 

  Est $1,074,698

  Not Listed For Sale

  17 Wakeman Rd, South Salem, NY 10590

  • 3 Beds
  • 3.5 Baths
  • 3,600 Sq Ft
  • Built 1964

  17 Wakeman Rd, South Salem, NY 10590

  Last Sold Summary

  • 49 Days On Market
• 

  

  /45

  $995,000

  Open Sat 1PM - 4PM

  • 4 Beds
  • 2.5 Baths
  • 2,936 Sq Ft

  50 Elmwood Rd, South Salem, NY 10590

  Elegant Retreat tucked in the heart of South Salem nestled on nearly 3 acres of scenic countryside. This beautifully maintained center hall Colonial offers the perfect blend of space, comfort, and modern convenience. Classic style with all 4 generous bedrooms on the second level, this home boasts a recently updated country kitchen & all new hardwood floors throughout. Dual fireplace with vaulted

  Giancarlo Pecora eXp Realty

  50 Elmwood Rd, South Salem, NY 10590
• 

  $2,799,000

  Sold Sep 29, 2025

  41 Rock Shelter Rd, Waccabuc, NY 10597

  • 5 Beds
  • 8 Baths
  • 7,313 Sq Ft
  • Built 2002

  Last Sold Summary

  • $383/SF
  • 132 Days On Market

  Current Estimated Value $2,895,284

  Last Listing Agent Jessica Cunningham

  41 Rock Shelter Rd, Waccabuc, NY 10597
• 

  Est $776,364

  Not Listed For Sale

  11 Roads End Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,684 Sq Ft
  • Built 1976

  11 Roads End Rd, South Salem, NY 10590

  Last Sold Summary

  • 121 Days On Market
• 

  

  /23

  $425,000

  Open Sat 12PM - 1:30PM

  • 3 Beds
  • 2 Baths
  • 1,200 Sq Ft

  14 W Main St, Goldens Bridge, NY 10526

  Unique opportunity to own a 3-bedroom, 2-bath home offering flexibility and future possibilities in the Goldens Bridge Lake Community, also known as The Colony. Property presents an opportunity for significant improvement or possibly new construction. One of the home's most exciting features is the approximately 480 sq. ft. walk-up attic, a truly unique space with endless potential. Whether

  Mark Boyland Keller Williams Realty Partner

  14 W Main St, Goldens Bridge, NY 10526
• 

  $360,000

  Sold Mar 23, 2026

  132 Stone Meadow, South Salem, NY 10590

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

  Last Sold Summary

  • 10% Below List Price
  • $324/SF
  • 64 Days On Market

  Current Estimated Value $360,061

  Last Listing Agent Lisa Sgobbo Century 21 Alliance Rlty Group

  132 Stone Meadow, South Salem, NY 10590
• 

  Est $880,309

  Not Listed For Sale

  3 Roads End Rd, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 2,856 Sq Ft
  • Built 1972

  3 Roads End Rd, South Salem, NY 10590

  Last Sold Summary

  • 11 Days On Market
• 

  

  /22

  $859,900

  $40K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,189 Sq Ft

  98 Smith Ridge Rd, South Salem, NY 10590

  Beautifully updated and move-in ready, this 4-bedroom home is set on 2 private acres in the highly desirable Katonah-Lewisboro School District. Thoughtfully renovated throughout, the home features refinished hardwood floors, fresh neutral interiors, brand-new stainless steel appliances, 2 full bathrooms, and an updated powder room.The light-filled open layout offers comfortable everyday

  Sari Shaw Compass Greater NY, LLC

  98 Smith Ridge Rd, South Salem, NY 10590
• 

  $550,000

  Sold May 14, 2026

  10 Skytop Dr, Katonah, NY 10536

  • 1 Bed
  • 1 Bath
  • 776 Sq Ft
  • Built 1930

  Last Sold Summary

  • 8% Below List Price
  • $709/SF
  • 16 Days On Market

  Current Estimated Value $585,175

  Last Listing Agent Angela Kessel Houlihan Lawrence Inc.

  10 Skytop Dr, Katonah, NY 10536
• 

  Est $1,340,422

  Not Listed For Sale

  12 Tri Brook Dr, South Salem, NY 10590

  • 4 Beds
  • 3.5 Baths
  • 4,701 Sq Ft
  • Built 1986

  12 Tri Brook Dr, South Salem, NY 10590

  Last Sold Summary

  • 35 Days On Market
• 

  

  /35

  $420,000

  • 1 Bed
  • 1 Bath
  • 1,112 Sq Ft

  156 Stone Meadow Unit 16156, South Salem, NY 10590

  Welcome to 156 Stone Meadow, an updated, contemporary condo offering sleek design, flexible living space, and modern comfort in the heart of South Salem. This beautifully maintained 1-bedroom, 1-bath residence lives like a 2-bedroom, featuring a spacious upstairs loft currently utilized as a second bedroom. Ideal for guest living, a home office, media room, or creative flex space, the

  Christopher Ferraro RE/MAX Town & Country

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

  $975,000

  Sold Jul 15, 2025

  26 Tri Brook Dr, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 3,016 Sq Ft
  • Built 1978

  Last Sold Summary

  • $323/SF
  • 17 Days On Market

  Current Estimated Value $1,044,773

  Last Listing Agent Carine Nowak Compass Greater NY, LLC

  26 Tri Brook Dr, South Salem, NY 10590
• 

  Est $987,976

  Not Listed For Sale

  4 Hillcrest Ct, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 2,456 Sq Ft
  • Built 1962

  4 Hillcrest Ct, South Salem, NY 10590

  Last Sold Summary

  • 7 Days On Market
• 

  

  /14

  $685,000

  $34K PRICE DROP Pending

  • 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
• 

  $387,500

  Sold Feb 26, 2026

  50 S Shore Dr, South Salem, NY 10590

  • 1 Bed
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1930

  Last Sold Summary

  • 2% Below List Price
  • $388/SF
  • 42 Days On Market

  Current Estimated Value $392,023

  Last Listing Agent Mark Boyland Keller Williams Realty Partner

  50 S Shore Dr, South Salem, NY 10590
• 

  Est $744,443

  Not Listed For Sale

  10 Deer Run Rd, South Salem, NY 10590

  • 4 Beds
  • 2 Baths
  • 1,894 Sq Ft
  • Built 1963

  10 Deer Run Rd, South Salem, NY 10590

  Last Sold Summary

  • 13 Days On Market
• 

  

  /9

  $679,000

  Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  9 Stewart Rd, South Salem, NY 10590

  This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, a fireplace warms the front parlor and living room. Beyond, the kitchen opens to a dining room and an expanded family room with a stone fireplace, home

  Larry Mango Giner Real Estate Inc.

  9 Stewart Rd, South Salem, NY 10590
• 

  $550,000

  Sold Aug 29, 2025

  26 Dr Tonys Rd, Somers, NY 10536

  • Land
  • 2.7 Acres
  • $203,704 per Acre

  Last Sold Summary

  • 8% Below List Price
  • 156 Days On Market

  Current Estimated Value $545,238

  Last Listing Agent Bill Reilly Billingsley Realty

  26 Dr Tonys Rd, Somers, NY 10536
• 

  Est $742,796

  Not Listed For Sale

  145 Elmwood Rd, South Salem, NY 10590

  • 3 Beds
  • 2 Baths
  • 2,218 Sq Ft
  • Built 1979

  145 Elmwood Rd, South Salem, NY 10590

  Last Sold Summary

  • 15 Days On Market
• 

  

  /29

  $1,695,000

  Pending

  • 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
• 

  $350,000

  Sold Jan 21, 2026

  26 Elmwood Rd, Lewisboro, NY 10590

  • Land
  • 3.47 Acres
  • $100,865 per Acre

  Last Sold Summary

  • 6% Above List Price
  • 37 Days On Market

  Current Estimated Value $350,845

  Last Listing Agent Julie Setterlund Julia B Fee Sothebys Int. Rlty

  26 Elmwood Rd, Lewisboro, NY 10590
• 

  Est $1,738,543

  Not Listed For Sale

  25 Beaver Pond Rd, South Salem, NY 10590

  • 5 Beds
  • 3.5 Baths
  • 6,000 Sq Ft
  • Built 2005

  25 Beaver Pond Rd, South Salem, NY 10590

  Last Sold Summary

  • 219 Days On Market
• 

  

  /43

  $725,000

  Pending

  • 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
• 

  $950,000

  Sold Nov 24, 2025

  134 Spring St, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 3,031 Sq Ft
  • Built 1794

  Last Sold Summary

  • $313/SF
  • 27 Days On Market

  Current Estimated Value $989,226

  Last Listing Agent Donna Ornstein William Raveis-New York LLC

  134 Spring St, South Salem, NY 10590
• 

  Est $1,507,181

  Not Listed For Sale

  15 Beaver Pond Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 3,498 Sq Ft
  • Built 1998

  15 Beaver Pond Rd, South Salem, NY 10590

  Last Sold Summary

  • 14 Days On Market
• 

  

  /24

  $650,000

  • 3 Beds
  • 2 Baths
  • 2,206 Sq Ft

  33 Sabbath Day Hill Rd, South Salem, NY 10590

  Perfect as a year-round residence or a private weekend retreat, this charming home offers comfortable living in a super convenient location. It sits on a quiet country road surrounded by nature, yet it is close to the highway (7 miles to I-684); train (8 miles to Katonah MTA Metro North station with direct trains to Grand Central), schools, and other everyday conveniences. This well-loved home

  Natasha Pazdzerskaia Coldwell Banker Realty

  33 Sabbath Day Hill Rd, South Salem, NY 10590
• 

  $1,050,000

  Sold Apr 17, 2026

  175 Waccabuc Rd, Goldens Bridge, NY 10526

  • 6 Beds
  • 2 Baths
  • 6,038 Sq Ft
  • Built 1827

  Last Sold Summary

  • 7% Below List Price
  • $174/SF
  • 147 Days On Market

  Current Estimated Value $1,230,387

  Last Listing Agent James Bergstraser RE/MAX Classic Realty

  175 Waccabuc Rd, Goldens Bridge, NY 10526
• 

  Est $1,465,797

  Not Listed For Sale

  11 Beaver Pond Rd, South Salem, NY 10590

  • 4 Beds
  • 2.5 Baths
  • 3,520 Sq Ft
  • Built 1998

  11 Beaver Pond Rd, South Salem, NY 10590

  Last Sold Summary

  • 13 Days On Market
• 

  

  /32

  $950,000

  $49K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  10 Silvermine Dr, South Salem, NY 10590

  This move-in-ready colonial offers a functional layout for everyday living and entertaining in a serene setting. Hardwood floors throughout, brand-new HVAC, updated kitchen, and bath. Bay windows provide leafy views of the woodsy property, pond, and old stone walls. A large family room with a cozy fireplace has sliders to enjoy outdoor living on a large deck. Upstairs are four quiet bedrooms. The

  Larry Mango Giner Real Estate Inc.

  10 Silvermine Dr, South Salem, NY 10590
• 

  $800,000

  Sold Sep 03, 2025

  4 Debbie Ln, Cross River, NY 10518

  • 3 Beds
  • 3 Baths
  • 2,064 Sq Ft
  • Built 1968

  Last Sold Summary

  • 18% Above List Price
  • $388/SF
  • 9 Days On Market

  Current Estimated Value $820,114

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

  4 Debbie Ln, Cross River, NY 10518
• 

  Est $1,469,154

  Not Listed For Sale

  9 Beaver Pond Rd, South Salem, NY 10590

  • 4 Beds
  • 4.5 Baths
  • 5,165 Sq Ft
  • Built 2000

  9 Beaver Pond Rd, South Salem, NY 10590

  Last Sold Summary

  • 80 Days On Market
• 

  

  /50

  $4,500,000

  $350K PRICE DROP

  • 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

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