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South Windham, CT Homes

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  • /30

    $199,900 Pending

    • 2 Beds
    • 1 Bath
    • 952 Sq Ft

    235 S Windham Rd, Willimantic, CT 06226

    Bring your vision for this charming 2-bedroom, 1 bath Ranch in South Windham, set on an expansive 6.2-acre lot with plenty of room to enjoy privacy and outdoor space. Built in 1948 and offering 950+ sq ft of comfortable one-level living, this home features vinyl siding, a classic gable roof with asphalt shingles, and a simple, functional layout that is easy to maintain. A full unfinished basement

    Agent Photo

    Anthony D'Amore

    eXp Realty

    (860) 530-6511

    235 S Windham Rd, Willimantic, CT 06226
  • 76 S Windham Rd, Willimantic, CT 06226

    $260,000 Sold Dec 23, 2025

    76 S Windham Rd, Willimantic, CT 06226

    • 3 Beds
    • 2 Baths
    • 1,002 Sq Ft
    • Built 1975

    Last Sold Summary

    • 4% Above List Price
    • $259/SF
    • 35 Days On Market

    Current Estimated Value $266,603

    Last Listing Agent Jayson Kemp Five Stars Realty

    76 S Windham Rd, Willimantic, CT 06226
    • 270 S Windham Rd Unit 67, Willimantic, CT 06226

      Est $113,784 Not Listed For Sale

      270 S Windham Rd Unit 67, Willimantic, CT 06226

      • 2 Beds
      • 1 Bath
      • 765 Sq Ft
      • Built 1968
      270 S Windham Rd Unit 67, Willimantic, CT 06226

      Last Sold Summary

      • 25% Above List Price
      • $119/SF
      • 13 Days On Market

      Last Sold Price $91,000

      Last Listing Agent Erica Molochnick RbRE, LLC

  • /22

    $315,000 Pending

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    9 Highland View Dr, South Windham, CT 06266

    Perfect first home, or downsize, with the big updates already done. This move-in ready property offers peace of mind for first-time buyers looking to avoid costly repairs and enjoy homeownership from day one. Three Bedrooms, open layout, pellet stove, garage with attic storage, an open breezeway, and Hard Wood Floors! Off street parking, Paved driveway. Recent improvements include a brand-new

    Brian Connolly Real Broker CT, LLC

    9 Highland View Dr, South Windham, CT 06266
  • 121 Highland View Dr, Windham, CT 06266

    $50,000 Sold Sep 26, 2025

    121 Highland View Dr, Windham, CT 06266

    • Land
    • 0.92 Acre
    • $54,348 per Acre

    Last Sold Summary

    • 11% Below List Price
    • 8 Days On Market

    Last Listing Agent Jeanne Crum Home Selling Team

    121 Highland View Dr, Windham, CT 06266
    • 200 Old Bush Hill Rd, Windham, CT 06226

      Est $381,162 Not Listed For Sale

      200 Old Bush Hill Rd, Windham, CT 06226

      • 3 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2025
      200 Old Bush Hill Rd, Windham, CT 06226

      Last Sold Summary

      • 18% Below List Price
      • $245/SF
      • 125 Days On Market

      Last Sold Price $465,000

      Last Listing Agent Timothy Morse Alliance Realty LLC

  • /33

    $279,900 Pending

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft

    39 S Windham Rd, Willimantic, CT 06226

    We have had a lot of interest on this property therefor we are asking for HIGHEST/BEST BY TUES. 3/10 AT NOON. Charming and well-maintained Cape set on a private 1.1-acre lot, offering peaceful surroundings while remaining close to local amenities and major commuter routes. This home features 1,120 sq ft of living space with 9ft ceilings. Town records reflect a 3-bedroom home; however, one bedroom

    Susan Walsh RE/MAX One

    39 S Windham Rd, Willimantic, CT 06226
  • 33 MacHine Shop Hill Rd, South Windham, CT 06266

    $160,000 Sold Dec 24, 2025

    33 MacHine Shop Hill Rd, South Windham, CT 06266

    • 5 Beds
    • 1 Bath
    • 2,548 Sq Ft
    • Built 1850

    Last Sold Summary

    • 33% Below List Price
    • $63/SF
    • 145 Days On Market

    Current Estimated Value $184,033

    Last Listing Agent Franchesca Pescatello Prue Realty LLC

    33 MacHine Shop Hill Rd, South Windham, CT 06266
    • 50 S Windham Rd, Willimantic, CT 06226

      Est $347,568 Not Listed For Sale

      50 S Windham Rd, Willimantic, CT 06226

      • 4 Beds
      • 2 Baths
      • 1,966 Sq Ft
      • Built 1975
      50 S Windham Rd, Willimantic, CT 06226

      Last Sold Summary

      • 5% Above List Price
      • $168/SF
      • 33 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Tonya Hughes Coldwell Banker Realty

  • /2

    $374,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft

    128 MacHine Shop Hill Rd, South Windham, CT 06266

    Charming New England Cape offering the perfect blend of timeless character and modern updates. Set on a nice-sized lot with a private yard, this beautifully maintained home features thoughtful renovations while preserving its original charm. The bright updated kitchen showcases white cabinetry, granite countertops, new stainless steel appliances, and fresh paint, creating a clean and inviting

    Nikki Defrancesco Coldwell Banker Realty

    128 MacHine Shop Hill Rd, South Windham, CT 06266
  • 1157 Windham Rd, Windham, CT 06266

    $441,750 Sold Sep 02, 2025

    1157 Windham Rd, Windham, CT 06266

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $316/SF
    • 229 Days On Market

    Current Estimated Value $445,070

    Last Listing Agent Timothy Morse Alliance Realty LLC

    1157 Windham Rd, Windham, CT 06266
    • 190 S Windham Rd, Willimantic, CT 06226

      Est $318,224 Not Listed For Sale

      190 S Windham Rd, Willimantic, CT 06226

      • 3 Beds
      • 2 Baths
      • 1,224 Sq Ft
      • Built 1987
      190 S Windham Rd, Willimantic, CT 06226

      Last Sold Summary

      • 22% Above List Price
      • $212/SF
      • 2 Days On Market

      Last Sold Price $260,000

      Last Listing Agent Kathleen Holland KW Legacy Partners

  • /33

    $292,900 Pending

    • 2 Beds
    • 3 Baths
    • 2,214 Sq Ft

    40 Sanitarium Rd, South Windham, CT 06266

    A rare find indeed. This Cape Cod style home is deceiving from the outside. Plenty of room in this beauty. Street card says 2 bedrooms, but you can utilize many finished heated rooms for additional bedrooms in this home. Finished basement above ground with kitchen, living space and bedroom. Nice floorplan on the main level offering living room/dining room combination with fireplace, full kitchen

    Martha Poole Carl Guild & Associates

    40 Sanitarium Rd, South Windham, CT 06266
  • 4 Main St, Willimantic, CT 06226

    $485,000 Sold Dec 29, 2025

    4 Main St, Willimantic, CT 06226

    • 9 Beds
    • 5 Baths
    • 5,134 Sq Ft
    • Built 1830

    Last Sold Summary

    • 6% Below List Price
    • $94/SF
    • 186 Days On Market

    Last Listing Agent Tammy Arute Arute Realty Group LLC

    4 Main St, Willimantic, CT 06226
    • 14 S Windham Rd, Willimantic, CT 06226

      Est $287,328 Not Listed For Sale

      14 S Windham Rd, Willimantic, CT 06226

      • 5 Beds
      • 2 Baths
      • 1,636 Sq Ft
      • Built 1951
      14 S Windham Rd, Willimantic, CT 06226

      Last Sold Summary

      • 15% Above List Price
      • $153/SF
      • 5 Days On Market

      Last Sold Price $250,000

      Last Listing Agent Maurita Leon Maurita's Home & Heart Realty LLC

  • 21 Russ Rd, Willimantic, CT 06226

    $175,000 Sold Mar 16, 2026

    21 Russ Rd, Willimantic, CT 06226

    • 4 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1949

    Last Sold Summary

    • 12% Below List Price
    • $152/SF
    • 96 Days On Market

    Current Estimated Value $209,638

    Last Listing Agent Christy Lofstrom Driscoll ERA Blanchard & Rossetto

    21 Russ Rd, Willimantic, CT 06226
    • 160 Highland View Dr, South Windham, CT 06266

      Est $363,352 Not Listed For Sale

      160 Highland View Dr, South Windham, CT 06266

      • 3 Beds
      • 1.5 Baths
      • 1,862 Sq Ft
      • Built 2006
      160 Highland View Dr, South Windham, CT 06266

      Last Sold Summary

      • 4% Above List Price
      • $188/SF
      • 6 Days On Market

      Last Sold Price $350,000

      Last Listing Agent Danielle Fortier Coldwell Banker Realty

  • 114 Highland View Dr, South Windham, CT 06266

    $335,000 Sold May 02, 2025

    114 Highland View Dr, South Windham, CT 06266

    • 5 Beds
    • 2.5 Baths
    • 2,660 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $126/SF
    • 54 Days On Market

    Current Estimated Value $362,644

    Last Listing Agent Lawrence Ross Weichert,REALTORS-Four Corners

    114 Highland View Dr, South Windham, CT 06266
    • 52 Old Plains Rd, Willimantic, CT 06226

      Est $241,348 Not Listed For Sale

      52 Old Plains Rd, Willimantic, CT 06226

      • 2 Beds
      • 1 Bath
      • 846 Sq Ft
      • Built 1950
      52 Old Plains Rd, Willimantic, CT 06226

      Last Sold Summary

      • 8% Above List Price
      • $264/SF
      • 9 Days On Market

      Last Sold Price $223,500

      Last Listing Agent Lisa Neundorf Castles Condos & Cottages, LLC

  • 84 MacHine Shop Hill Rd, South Windham, CT 06266

    $240,000 Sold Dec 03, 2025

    84 MacHine Shop Hill Rd, South Windham, CT 06266

    • 2 Beds
    • 1.5 Baths
    • 2,396 Sq Ft
    • Built 1967

    Last Sold Summary

    • 4% Above List Price
    • $100/SF
    • 17 Days On Market

    Current Estimated Value $241,952

    Last Listing Agent Scott Bayne Century 21 Bay-Mar Realty

    84 MacHine Shop Hill Rd, South Windham, CT 06266
    • 41 Antrim Rd, Willimantic, CT 06226

      Est $276,533 Not Listed For Sale

      41 Antrim Rd, Willimantic, CT 06226

      • 4 Beds
      • 2 Baths
      • 1,092 Sq Ft
      • Built 2004
      41 Antrim Rd, Willimantic, CT 06226

      Last Sold Summary

      • 63% Above List Price
      • $156/SF
      • 13 Days On Market

      Last Sold Price $170,000

      Last Listing Agent Stephen Daly KW Legacy Partners

  • 6 Old Plains Rd, Willimantic, CT 06226

    $300,000 Sold Sep 29, 2025

    6 Old Plains Rd, Willimantic, CT 06226

    • 3 Beds
    • 2.5 Baths
    • 2,018 Sq Ft
    • Built 1830

    Last Sold Summary

    • 7% Above List Price
    • $149/SF
    • 9 Days On Market

    Current Estimated Value $305,897

    Last Listing Agent Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

    6 Old Plains Rd, Willimantic, CT 06226
    • 44 Pigeon Swamp Rd, South Windham, CT 06266

      Est $308,221 Not Listed For Sale

      44 Pigeon Swamp Rd, South Windham, CT 06266

      • 3 Beds
      • 2 Baths
      • 1,674 Sq Ft
      • Built 1987
      44 Pigeon Swamp Rd, South Windham, CT 06266

      Last Sold Summary

      • 7% Below List Price
      • $197/SF
      • 51 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Timothy Morse Alliance Realty LLC

  • 8 Howard Dr, Willimantic, CT 06226

    $235,000 Sold Feb 06, 2026

    8 Howard Dr, Willimantic, CT 06226

    • 2 Beds
    • 1 Bath
    • 742 Sq Ft
    • Built 1956

    Last Sold Summary

    • 6% Below List Price
    • $317/SF
    • 22 Days On Market

    Current Estimated Value $233,565

    Last Listing Agent Julienne Jaber KW Legacy Partners

    8 Howard Dr, Willimantic, CT 06226
    • 12 Old Plains Rd, Willimantic, CT 06226

      Est $286,672 Not Listed For Sale

      12 Old Plains Rd, Willimantic, CT 06226

      • 3 Beds
      • 1 Bath
      • 1,440 Sq Ft
      • Built 1890
      12 Old Plains Rd, Willimantic, CT 06226

      Last Sold Summary

      • 6% Below List Price
      • $212/SF
      • 36 Days On Market

      Last Sold Price $305,000

      Last Listing Agent Sue Esposito Home Selling Team

  • 44 Old Plains Rd, Willimantic, CT 06226

    $215,000 Sold Jul 25, 2025

    44 Old Plains Rd, Willimantic, CT 06226

    • 2 Beds
    • 1 Bath
    • 1,148 Sq Ft
    • Built 1939

    Last Sold Summary

    • 4% Below List Price
    • $187/SF
    • 41 Days On Market

    Current Estimated Value $230,754

    Last Listing Agent Melinda Walencewicz eXp Realty

    44 Old Plains Rd, Willimantic, CT 06226
    • 59 MacHine Shop Hill Rd, South Windham, CT 06266

      Est $239,143 Not Listed For Sale

      59 MacHine Shop Hill Rd, South Windham, CT 06266

      • 3 Beds
      • 1.5 Baths
      • 2,022 Sq Ft
      • Built 1872
      59 MacHine Shop Hill Rd, South Windham, CT 06266

      Last Sold Summary

      • 62% Above List Price
      • $73/SF
      • 11 Days On Market

      Last Sold Price $148,000

      Last Listing Agent Tammy Boles-Senkewitcz Asset Real Estate

  • 102 MacHine Shop Hill Rd, South Windham, CT 06266

    $495,000 Sold Jun 18, 2025

    102 MacHine Shop Hill Rd, South Windham, CT 06266

    • 4 Beds
    • 2.5 Baths
    • 2,966 Sq Ft
    • Built 1865

    Last Sold Summary

    • 1% Below List Price
    • $167/SF
    • 5 Days On Market

    Current Estimated Value $494,391

    Last Listing Agent Sherry Borgeson Berkshire Hathaway NE Prop.

    102 MacHine Shop Hill Rd, South Windham, CT 06266
    • 101 Wadsworth Ln, Willimantic, CT 06226

      Est $387,336 Not Listed For Sale

      101 Wadsworth Ln, Willimantic, CT 06226

      • 4 Beds
      • 2.5 Baths
      • 2,527 Sq Ft
      • Built 1765
      101 Wadsworth Ln, Willimantic, CT 06226

      Last Sold Summary

      • 1% Above List Price
      • $152/SF
      • 123 Days On Market

      Last Sold Price $385,000

      Last Listing Agent Dale Bunn Riverview Realty, LLC

  • 925 Windham Rd, South Windham, CT 06266

    $316,500 Sold Mar 04, 2026

    925 Windham Rd, South Windham, CT 06266

    • 3 Beds
    • 1 Bath
    • 1,344 Sq Ft
    • Built 1960

    Last Sold Summary

    • 1% Below List Price
    • $235/SF
    • 39 Days On Market

    Current Estimated Value $312,059

    Last Listing Agent Clarence Russ Home Selling Team

    925 Windham Rd, South Windham, CT 06266
    • 988 Windham Rd, South Windham, CT 06266

      Est $245,803 Not Listed For Sale

      988 Windham Rd, South Windham, CT 06266

      • 3 Beds
      • 1 Bath
      • 1,220 Sq Ft
      • Built 1920
      988 Windham Rd, South Windham, CT 06266

      Last Sold Summary

      • 17% Above List Price
      • $172/SF
      • 64 Days On Market

      Last Sold Price $210,000

      Last Listing Agent Jack Fulton Home Selling Team

  • 176 Bush Hill Rd, Willimantic, CT 06226

    $362,000 Sold Oct 31, 2025

    176 Bush Hill Rd, Willimantic, CT 06226

    • 3 Beds
    • 2 Baths
    • 1,137 Sq Ft
    • Built 1998

    Last Sold Summary

    • 3% Above List Price
    • $318/SF
    • 47 Days On Market

    Current Estimated Value $360,605

    Last Listing Agent Kara Mazzola First Choice Realty

    176 Bush Hill Rd, Willimantic, CT 06226
    • 31 Abbe St, Willimantic, CT 06226

      Est $232,614 Not Listed For Sale

      31 Abbe St, Willimantic, CT 06226

      • 2 Beds
      • 1.5 Baths
      • 1,357 Sq Ft
      • Built 1934
      31 Abbe St, Willimantic, CT 06226

      Last Sold Summary

      • 55% Above List Price
      • $111/SF
      • 6 Days On Market

      Last Sold Price $150,000

      Last Listing Agent Ryan Lamb RE/MAX

  • 270 S Windham Rd Unit 52, Willimantic, CT 06226

    $115,000 Sold Apr 30, 2025

    270 S Windham Rd Unit 52, Willimantic, CT 06226

    • 2 Beds
    • 1 Bath
    • 790 Sq Ft
    • Built 1968

    Last Sold Summary

    • 8% Below List Price
    • $146/SF
    • 82 Days On Market

    Current Estimated Value $118,885

    Last Listing Agent Jacob Essig William Pitt Sotheby's Int'l

    270 S Windham Rd Unit 52, Willimantic, CT 06226
    • 354 S Windham Rd, Willimantic, CT 06226

      Est $259,385 Not Listed For Sale

      354 S Windham Rd, Willimantic, CT 06226

      • 3 Beds
      • 2 Baths
      • 1,488 Sq Ft
      • Built 1920
      354 S Windham Rd, Willimantic, CT 06226

      Last Sold Summary

      • 16% Above List Price
      • $150/SF
      • 40 Days On Market

      Last Sold Price $223,000

      Last Listing Agent Brittany Kimlingen First Choice Realty

  • 1145 Windham Rd, Windham, CT 06266

    $450,000 Sold Sep 04, 2025

    1145 Windham Rd, Windham, CT 06266

    • 3 Beds
    • 2.5 Baths
    • 3,698 Sq Ft
    • Built 2025

    Last Sold Summary

    • 2% Below List Price
    • $122/SF
    • 2 Days On Market

    Current Estimated Value $451,612

    Last Listing Agent Timothy Morse Alliance Realty LLC

    1145 Windham Rd, Windham, CT 06266
    • 29 Pemberton Rd, Willimantic, CT 06226

      Est $289,029 Not Listed For Sale

      29 Pemberton Rd, Willimantic, CT 06226

      • 3 Beds
      • 1.5 Baths
      • 1,510 Sq Ft
      • Built 1968
      29 Pemberton Rd, Willimantic, CT 06226

      Last Sold Summary

      • 6% Above List Price
      • $180/SF
      • 35 Days On Market

      Last Sold Price $272,000

      Last Listing Agent Sara Hassler List N Show LLC

  • 106 Highland View Dr, South Windham, CT 06266

    $340,000 Sold Jul 08, 2025

    106 Highland View Dr, South Windham, CT 06266

    • 3 Beds
    • 1.5 Baths
    • 2,276 Sq Ft
    • Built 1978

    Last Sold Summary

    • 1% Above List Price
    • $149/SF
    • 16 Days On Market

    Current Estimated Value $342,011

    Last Listing Agent Catherine Deschenes eXp Realty

    106 Highland View Dr, South Windham, CT 06266
    • 67 Old Windham Rd, South Windham, CT 06266

      Est $289,980 Not Listed For Sale

      67 Old Windham Rd, South Windham, CT 06266

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft
      • Built 1977
      67 Old Windham Rd, South Windham, CT 06266

      Last Sold Summary

      • 18% Above List Price
      • $163/SF
      • 38 Days On Market

      Last Sold Price $245,000

      Last Listing Agent Laurie Hayes-Hagstrom On The Move Realty, LLC

  • 270 S Windham Rd Unit 53, Willimantic, CT 06226

    $115,000 Sold Dec 17, 2025

    270 S Windham Rd Unit 53, Willimantic, CT 06226

    • 2 Beds
    • 1 Bath
    • 765 Sq Ft
    • Built 1968

    Last Sold Summary

    • $150/SF
    • 56 Days On Market

    Current Estimated Value $114,558

    Last Listing Agent Michael Price KW Legacy Partners

    270 S Windham Rd Unit 53, Willimantic, CT 06226

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