5,223

Lewisboro, NY Homes

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    • 15 Beaver Pond Rd, South Salem, NY 10590

      Est $1,483,474

      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

      Last Listing Agent Cate Hegarty Compass Greater NY, LLC

  • 157 Jay Ct, Cross River, NY 10518
    157 Jay Ct, Cross River, NY 10518
    157 Jay Ct, Cross River, NY 10518
    /24

    $545,000

    $30K PRICE DROP
    • 1 Bed
    • 1.5 Baths
    • 1,451 Sq Ft

    157 Jay Ct, Cross River, NY 10518

    Welcome to this beautifully maintained townhouse in the highly desirable Meadows community. Ideally located near shopping, restaurants, and schools, this home offers affordable living, excellent amenities, and low taxes within the sought-after Katonah-Lewisboro School District. Situated in one of the most private locations in the development, the home is just a short walk to the community pool

    Judith Collins-Turi William Raveis-New York LLC

    157 Jay Ct, Cross River, NY 10518
  • 242 Smith Ridge Rd, South Salem, NY 10590

    $750,000

    Sold Nov 07, 2025

    242 Smith Ridge Rd, South Salem, NY 10590

    • 3 Beds
    • 2 Baths
    • 1,627 Sq Ft
    • Built 1776

    Last Sold Summary

    • 6% Below List Price
    • $461/SF
    • 124 Days On Market

    Current Estimated Value $764,553

    Last Listing Agent Timi Parsons Houlihan Lawrence Inc.

    242 Smith Ridge Rd, South Salem, NY 10590
    • 11 Beaver Pond Rd, South Salem, NY 10590

      Est $1,481,829

      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

      Last Listing Agent Nancy Lacavalla Ginnel Real Estate

  • 121 Post Office Rd, South Salem, NY 10590
    121 Post Office Rd, South Salem, NY 10590
    121 Post Office Rd, South Salem, NY 10590
    /33

    $1,795,000

    $100K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 3,307 Sq Ft

    121 Post Office Rd, South Salem, NY 10590

    RIVERBEND FARM. Remarkable frontage on the rushing Waccabuc River. The original Adams Dairy Farm--an absolutely breathtaking property with level lawns lined by old stone walls, specimen trees and vibrant flowering perennials. Incredible gardens of Daffodils, Tulips, Iris, wild Roses, Lilac, Wysteria, Allium, and Peonies along with fragrant and flowering Magnolia, Apple, and Viburnum. Raised bed,

    Jennie Doukas Ginnel Real Estate

    121 Post Office Rd, South Salem, NY 10590
  • 58 Winterberry Cir, Cross River, NY 10518

    $525,000

    Sold Jan 07, 2026

    58 Winterberry Cir, Cross River, NY 10518

    • 1 Bed
    • 1.5 Baths
    • 1,941 Sq Ft
    • Built 1987

    Last Sold Summary

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

    Current Estimated Value $551,192

    Last Listing Agent Carine Nowak Compass Greater NY, LLC

    58 Winterberry Cir, Cross River, NY 10518
    • 9 Beaver Pond Rd, South Salem, NY 10590

      Est $1,478,285

      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

      Last Listing Agent Mark Boyland Keller Williams Realty Partner

  • 1 Sabbath Day Hill Rd, South Salem, NY 10590
    1 Sabbath Day Hill Rd, South Salem, NY 10590
    1 Sabbath Day Hill Rd, South Salem, NY 10590
    /24

    $975,000

    • 4 Beds
    • 3 Baths
    • 2,490 Sq Ft

    1 Sabbath Day Hill Rd, South Salem, NY 10590

    Nestled on a picturesque road in the heart of South Salem, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect balance of privacy, comfort, and convenience. Lovingly cared for by only its second owner, this exceptional home has been thoughtfully updated over the years while maintaining its warmth and charm. Set amid mature woodlands, the hilltop retreat offers a peaceful

    Karen Susan Savir Coldwell Banker Realty

    1 Sabbath Day Hill Rd, South Salem, NY 10590
  • 16 Stonewall Ct, South Salem, NY 10590

    $960,000

    Sold Oct 29, 2025

    16 Stonewall Ct, South Salem, NY 10590

    • 4 Beds
    • 2.5 Baths
    • 2,626 Sq Ft
    • Built 1982

    Last Sold Summary

    • 4% Below List Price
    • $366/SF
    • 30 Days On Market

    Current Estimated Value $1,003,652

    Last Listing Agent Cecilia Heller Houlihan Lawrence Inc.

    16 Stonewall Ct, South Salem, NY 10590
    • 219 Kitchawan Rd, South Salem, NY 10590

      Est $865,612

      Not Listed For Sale

      219 Kitchawan Rd, South Salem, NY 10590

      • 2 Beds
      • 1.5 Baths
      • 1,600 Sq Ft
      • Built 1970
      219 Kitchawan Rd, South Salem, NY 10590

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  • 0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590
    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590
    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590
    /7

    $1,500,000

    • Land
    • 4.3 Acres
    • $348,837 per Acre

    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590

    Rare opportunity to build a custom estate on an exceptional property with sweeping, long-range, breathtaking sunset views. This remarkable parcel offers a stunning setting to create a home tailored to your vision. Utility services are already in place, and the Board of Health has approved the 4.3-acre parcel for a five-bedroom residence. A truly special offering with endless possibilities.

    Susan Stillman Houlihan Lawrence Inc.

    0 Church Tavern Rd Unit KEY995093, South Salem, NY 10590
  • 20 Oscaleta Rd, South Salem, NY 10590

    $1,900,000

    Sold Jun 29, 2026

    20 Oscaleta Rd, South Salem, NY 10590

    • 5 Beds
    • 4.5 Baths
    • 4,886 Sq Ft
    • Built 1954

    Last Sold Summary

    • 5% Below List Price
    • $389/SF
    • 13 Days On Market

    Current Estimated Value $1,952,817

    Last Listing Agent Angela Kessel Houlihan Lawrence Inc.

    20 Oscaleta Rd, South Salem, NY 10590
    • 207 Kitchawan Rd, South Salem, NY 10590

      Est $953,682

      Not Listed For Sale

      207 Kitchawan Rd, South Salem, NY 10590

      • 3 Beds
      • 2 Baths
      • 2,103 Sq Ft
      • Built 1800
      207 Kitchawan Rd, South Salem, NY 10590

      Last Sold Summary

      • 27 Days On Market

      Last Listing Agent Urs Klarer Coldwell Banker Realty

  • 50 Elmwood Rd, South Salem, NY 10590
    50 Elmwood Rd, South Salem, NY 10590
    50 Elmwood Rd, South Salem, NY 10590
    /46

    $895,000

    • 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
  • 9 Col Ferris Rd, South Salem, NY 10590

    $1,318,000

    Sold Nov 05, 2025

    9 Col Ferris Rd, South Salem, NY 10590

    • 4 Beds
    • 4 Baths
    • 4,325 Sq Ft
    • Built 1994

    Last Sold Summary

    • 4% Below List Price
    • $305/SF
    • 94 Days On Market

    Current Estimated Value $1,314,388

    Last Listing Agent Lisa Berliner Coldwell Banker Realty

    9 Col Ferris Rd, South Salem, NY 10590
    • 42 Old Church Ln, South Salem, NY 10590

      Est $1,447,148

      Not Listed For Sale

      42 Old Church Ln, South Salem, NY 10590

      • 3 Beds
      • 2.5 Baths
      • 4,275 Sq Ft
      • Built 1978
      42 Old Church Ln, South Salem, NY 10590

      Last Sold Summary

      • 85 Days On Market

      Last Listing Agent Nancy Musich Houlihan Lawrence Inc.

  • 3 Bouton St, South Salem, NY 10590
    3 Bouton St, South Salem, NY 10590
    3 Bouton St, South Salem, NY 10590
    /25

    $775,000

    Open Sun 1PM - 3PM
    • 3 Beds
    • 2 Baths
    • 1,754 Sq Ft

    3 Bouton St, South Salem, NY 10590

    Move right into the lake lifestyle! Completely renovated and thoughtfully designed, this turn-key, contemporary ranch offers the perfect blend of modern comfort and easy one-level living.Nestled in the sought-after Truesdale Lake area of South Salem, this sun-drenched three-bedroom, two-full-bath home is just a short stroll to the lake and beach. An inviting open floor plan creates an

    Mark Boyland Keller Williams Realty Partner

    3 Bouton St, South Salem, NY 10590
  • 4 Fairview Ct, Cross River, NY 10518

    $1,633,200

    Sold Jan 23, 2026

    4 Fairview Ct, Cross River, NY 10518

    • 4 Beds
    • 3 Baths
    • 4,525 Sq Ft
    • Built 1997

    Last Sold Summary

    • 13% Above List Price
    • $361/SF
    • 17 Days On Market

    Current Estimated Value $1,644,020

    Last Listing Agent Rita Carrozza Houlihan Lawrence Inc.

    4 Fairview Ct, Cross River, NY 10518
    • 34 Old Church Ln, South Salem, NY 10590

      Est $1,402,715

      Not Listed For Sale

      34 Old Church Ln, South Salem, NY 10590

      • 4 Beds
      • 2.5 Baths
      • 2,798 Sq Ft
      • Built 1972
      34 Old Church Ln, South Salem, NY 10590

      Last Sold Summary

      • 161 Days On Market

      Last Listing Agent Melissa Frank Lutz Douglas Elliman Real Estate

  • 17 Brundige Dr, Goldens Bridge, NY 10526

    $1,400,000

    Sold Jan 15, 2026

    17 Brundige Dr, Goldens Bridge, NY 10526

    • 4 Beds
    • 4.5 Baths
    • 5,660 Sq Ft
    • Built 1991

    Last Sold Summary

    • 2% Above List Price
    • $247/SF
    • 35 Days On Market

    Current Estimated Value $1,468,327

    Last Listing Agent Christine Schaaf Coldwell Banker Realty

    17 Brundige Dr, Goldens Bridge, NY 10526
    • 102 Ridgeland Rd, South Salem, NY 10590

      Est $598,567

      Not Listed For Sale

      102 Ridgeland Rd, South Salem, NY 10590

      • 3 Beds
      • 2 Baths
      • 1,644 Sq Ft
      • Built 1950
      102 Ridgeland Rd, South Salem, NY 10590

      Last Sold Summary

      • 37 Days On Market

      Last Listing Agent Patricia Hinkley Coldwell Banker Realty

  • 1 Canaan Cir, South Salem, NY 10590

    $1,400,000

    Sold Jul 01, 2026

    1 Canaan Cir, South Salem, NY 10590

    • 4 Beds
    • 4.5 Baths
    • 4,076 Sq Ft
    • Built 1989

    Last Sold Summary

    • 1% Above List Price
    • $343/SF
    • 8 Days On Market

    Current Estimated Value $1,270,771

    Last Listing Agent James LaTempa Compass Greater NY, LLC

    1 Canaan Cir, South Salem, NY 10590
    • 130 Lake Kitchawan Dr, South Salem, NY 10590

      Est $313,811

      Not Listed For Sale

      130 Lake Kitchawan Dr, South Salem, NY 10590

      • 2 Beds
      • 1 Bath
      • 950 Sq Ft
      • Built 1924
      130 Lake Kitchawan Dr, South Salem, NY 10590

      Last Sold Summary

      • 22 Days On Market

      Last Listing Agent Joanne Monteleone Ginnel Real Estate

  • 71 Fox Run, South Salem, NY 10590

    $420,000

    Sold Oct 30, 2025

    71 Fox Run, South Salem, NY 10590

    • 2 Beds
    • 1.5 Baths
    • 1,407 Sq Ft
    • Built 1982

    Last Sold Summary

    • 1% Below List Price
    • $299/SF
    • 25 Days On Market

    Current Estimated Value $443,198

    Last Listing Agent Mark Boyland Keller Williams Realty Partner

    71 Fox Run, South Salem, NY 10590
    • 48 Lake Kitchawan Dr, South Salem, NY 10590

      Est $508,940

      Not Listed For Sale

      48 Lake Kitchawan Dr, South Salem, NY 10590

      • 3 Beds
      • 2 Baths
      • 1,519 Sq Ft
      • Built 1930
      48 Lake Kitchawan Dr, South Salem, NY 10590

      Last Sold Summary

      • 35 Days On Market

      Last Listing Agent Wendy Loring William Raveis-New York LLC

  • 32 Boulder Ln, Goldens Bridge, NY 10526

    $671,000

    Sold Jul 06, 2026

    32 Boulder Ln, Goldens Bridge, NY 10526

    • 3 Beds
    • 2.5 Baths
    • 1,706 Sq Ft
    • Built 1977

    Last Sold Summary

    • $393/SF
    • 25 Days On Market

    Current Estimated Value $668,835

    Last Listing Agent Melissa DeFeo Howard Hanna Rand Realty

    32 Boulder Ln, Goldens Bridge, NY 10526
    • 12 Truesdale Lake Dr, South Salem, NY 10590

      Est $772,490

      Not Listed For Sale

      12 Truesdale Lake Dr, South Salem, NY 10590

      • 4 Beds
      • 2 Baths
      • 1,875 Sq Ft
      • Built 1971
      12 Truesdale Lake Dr, South Salem, NY 10590

      Last Sold Summary

      • 44 Days On Market

      Last Listing Agent Eileen McGrath Douglas Elliman Real Estate

  • 54 Lockwood Rd, South Salem, NY 10590

    $945,000

    Sold Mar 27, 2026

    54 Lockwood Rd, South Salem, NY 10590

    • 4 Beds
    • 2 Baths
    • 1,572 Sq Ft
    • Built 1965

    Last Sold Summary

    • $601/SF
    • 21 Days On Market

    Current Estimated Value $944,071

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

    54 Lockwood Rd, South Salem, NY 10590
    • 4 Salem Ln, South Salem, NY 10590

      Est $844,332

      Not Listed For Sale

      4 Salem Ln, South Salem, NY 10590

      • 3 Beds
      • 2.5 Baths
      • 2,406 Sq Ft
      • Built 1967
      4 Salem Ln, South Salem, NY 10590

      Last Sold Summary

      • 143 Days On Market

      Last Listing Agent Daniel Feldman William Raveis-New York LLC

  • 6 Hunt Farm Rd, Waccabuc, NY 10597

    $1,325,000

    Sold Aug 21, 2025

    6 Hunt Farm Rd, Waccabuc, NY 10597

    • 3 Beds
    • 2.5 Baths
    • 2,456 Sq Ft
    • Built 1985

    Last Sold Summary

    • $539/SF
    • 11 Days On Market

    Current Estimated Value $1,358,991

    Last Listing Agent Christine Foster Corcoran Legends Realty

    6 Hunt Farm Rd, Waccabuc, NY 10597
    • 2 Salem Ln, South Salem, NY 10590

      Est $858,940

      Not Listed For Sale

      2 Salem Ln, South Salem, NY 10590

      • 3 Beds
      • 2 Baths
      • 2,132 Sq Ft
      • Built 1976
      2 Salem Ln, South Salem, NY 10590

      Last Sold Summary

      • 18 Days On Market

      Last Listing Agent Daniel Feldman William Raveis-New York LLC

  • 274 Maplewood Dr Unit 32274, South Salem, NY 10590

    $395,000

    Sold Jun 29, 2026

    274 Maplewood Dr Unit 32274, South Salem, NY 10590

    • 1 Bed
    • 1 Bath
    • 970 Sq Ft
    • Built 1994

    Last Sold Summary

    • 3% Above List Price
    • $407/SF
    • 16 Days On Market

    Current Estimated Value $395,897

    Last Listing Agent Elizabeth Koski Coldwell Banker Realty

    274 Maplewood Dr Unit 32274, South Salem, NY 10590
    • 33 Salem Ln, South Salem, NY 10590

      Est $839,411

      Not Listed For Sale

      33 Salem Ln, South Salem, NY 10590

      • 3 Beds
      • 2 Baths
      • 2,022 Sq Ft
      • Built 1962
      33 Salem Ln, South Salem, NY 10590

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Carine Nowak Compass Greater NY, LLC

  • 153 Lake Kitchawan Dr, South Salem, NY 10590

    $550,000

    Sold Jun 23, 2026

    153 Lake Kitchawan Dr, South Salem, NY 10590

    • 2 Beds
    • 1 Bath
    • 876 Sq Ft
    • Built 1925

    Last Sold Summary

    • 10% Above List Price
    • $628/SF
    • 19 Days On Market

    Current Estimated Value $512,894

    Last Listing Agent Spencer Matthews Houlihan Lawrence Inc.

    153 Lake Kitchawan Dr, South Salem, NY 10590
    • 42 Lake Shore Dr, South Salem, NY 10590

      Est $1,003,289

      Not Listed For Sale

      42 Lake Shore Dr, South Salem, NY 10590

      • 4 Beds
      • 2.5 Baths
      • 2,472 Sq Ft
      • Built 1969
      42 Lake Shore Dr, South Salem, NY 10590

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Donna Ornstein William Raveis-New York LLC

  • 133 Boway Rd, South Salem, NY 10590

    $2,900,000

    Sold Jun 03, 2026

    133 Boway Rd, South Salem, NY 10590

    • 6 Beds
    • 5.5 Baths
    • 6,344 Sq Ft
    • Built 1976

    Last Sold Summary

    • 2% Below List Price
    • $457/SF
    • 166 Days On Market

    Current Estimated Value $2,829,156

    Last Listing Agent Mary Anne Condon Ginnel Real Estate

    133 Boway Rd, South Salem, NY 10590
    • 9 Howe St, South Salem, NY 10590

      Est $850,990

      Not Listed For Sale

      9 Howe St, South Salem, NY 10590

      • 3 Beds
      • 2.5 Baths
      • 2,380 Sq Ft
      • Built 1974
      9 Howe St, South Salem, NY 10590

      Last Sold Summary

      • 58 Days On Market

      Last Listing Agent Mary Anne Condon Ginnel Real Estate

  • 49 Winterberry Cir, Cross River, NY 10518

    $625,000

    Sold May 08, 2026

    49 Winterberry Cir, Cross River, NY 10518

    • 2 Beds
    • 2.5 Baths
    • 1,570 Sq Ft
    • Built 1986

    Last Sold Summary

    • 8% Above List Price
    • $398/SF
    • 12 Days On Market

    Current Estimated Value $618,011

    Last Listing Agent Margo Lancia Houlihan Lawrence Inc.

    49 Winterberry Cir, Cross River, NY 10518
    • 16 Gilbert St, South Salem, NY 10590

      Est $890,318

      Not Listed For Sale

      16 Gilbert St, South Salem, NY 10590

      • 4 Beds
      • 1.5 Baths
      • 1,396 Sq Ft
      • Built 1928
      16 Gilbert St, South Salem, NY 10590

      Last Sold Summary

      • 239 Days On Market

      Last Listing Agent Donna Ornstein William Raveis-New York LLC

  • 17 W Main St, Goldens Bridge, NY 10526

    $260,000

    Sold Dec 23, 2025

    17 W Main St, Goldens Bridge, NY 10526

    • 1 Bed
    • 1 Bath
    • 1,176 Sq Ft
    • Built 1948

    Last Sold Summary

    • 16% Above List Price
    • $221/SF
    • 35 Days On Market

    Current Estimated Value $325,410

    Last Listing Agent Suzanne Welch Coldwell Banker Realty

    17 W Main St, Goldens Bridge, NY 10526

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