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Recently Sold South Windham, CT Homes

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  • 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 $258,513

    Last Listing Agent Jayson Kemp Five Stars Realty

    76 S Windham Rd, Willimantic, CT 06226
  • 121 Highland View Dr, Windham, CT 06266

    $50,000

    Sold Sep 26, 2025

    121 Highland View Dr, Windham, CT 06266

    • Land
    • 40,075 Sq Ft
    • $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
  • 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 $205,231

    Last Listing Agent Franchesca Pescatello Prue Realty LLC

    33 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 $447,260

    Last Listing Agent Timothy Morse Alliance Realty LLC

    1157 Windham Rd, Windham, CT 06266
  • 9 Highland View Dr, South Windham, CT 06266

    $326,000

    Sold Apr 10, 2026

    9 Highland View Dr, South Windham, CT 06266

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1962

    Last Sold Summary

    • 3% Above List Price
    • $340/SF
    • 32 Days On Market

    Current Estimated Value $319,289

    Last Listing Agent Brian Connolly Real Broker CT, LLC

    9 Highland View Dr, South Windham, CT 06266
  • 39 S Windham Rd, Willimantic, CT 06226

    $310,000

    Sold Apr 24, 2026

    39 S Windham Rd, Willimantic, CT 06226

    • 3 Beds
    • 1 Bath
    • 1,120 Sq Ft
    • Built 1949

    Last Sold Summary

    • 11% Above List Price
    • $277/SF
    • 4 Days On Market

    Current Estimated Value $295,911

    Last Listing Agent Susan Walsh RE/MAX One

    39 S Windham Rd, Willimantic, CT 06226
  • 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
  • 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 $277,415

    Last Listing Agent Christy Lofstrom Driscoll ERA Blanchard & Rossetto

    21 Russ Rd, Willimantic, CT 06226
  • 128 MacHine Shop Hill Rd, South Windham, CT 06266

    $395,000

    Sold Jun 01, 2026

    128 MacHine Shop Hill Rd, South Windham, CT 06266

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1935

    Last Sold Summary

    • 5% Above List Price
    • $218/SF
    • 47 Days On Market

    Current Estimated Value $344,580

    Last Listing Agent Nikki Defrancesco Coldwell Banker Realty

    128 MacHine Shop Hill Rd, South Windham, CT 06266
  • 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 $248,937

    Last Listing Agent Scott Bayne Century 21 Bay-Mar Realty

    84 MacHine Shop Hill Rd, South Windham, CT 06266
  • 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 $296,976

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

    6 Old Plains Rd, Willimantic, CT 06226
  • 21 Russ Rd, Willimantic, CT 06226

    $340,000

    Sold Jun 05, 2026

    21 Russ Rd, Willimantic, CT 06226

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

    Last Sold Summary

    • 5% Above List Price
    • $295/SF
    • 25 Days On Market

    Current Estimated Value $277,415

    Last Listing Agent Ryan Newport Social & Co Realty

    21 Russ Rd, Willimantic, CT 06226
  • 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 $229,771

    Last Listing Agent Julienne Jaber KW Legacy Partners

    8 Howard Dr, Willimantic, CT 06226
  • 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 $223,209

    Last Listing Agent Melinda Walencewicz eXp Realty

    44 Old Plains Rd, Willimantic, CT 06226
  • 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 $500,832

    Last Listing Agent Sherry Borgeson Berkshire Hathaway NE Prop.

    102 MacHine Shop Hill Rd, South Windham, CT 06266
  • 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 $313,341

    Last Listing Agent Clarence Russ Home Selling Team

    925 Windham Rd, South Windham, CT 06266
  • 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 $348,136

    Last Listing Agent Kara Mazzola First Choice Realty

    176 Bush Hill Rd, Willimantic, CT 06226
  • 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 $447,092

    Last Listing Agent Timothy Morse Alliance Realty LLC

    1145 Windham Rd, Windham, CT 06266
  • 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 $339,982

    Last Listing Agent Catherine Deschenes eXp Realty

    106 Highland View Dr, South Windham, CT 06266
  • 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 $112,397

    Last Listing Agent Michael Price KW Legacy Partners

    270 S Windham Rd Unit 53, Willimantic, CT 06226
  • 128 MacHine Shop Hill Rd, South Windham, CT 06266

    $175,000

    Sold Oct 29, 2025

    128 MacHine Shop Hill Rd, South Windham, CT 06266

    • 3 Beds
    • 2 Baths
    • 1,814 Sq Ft
    • Built 1935

    Last Sold Summary

    • $96/SF
    • 5 Days On Market

    Current Estimated Value $344,580

    Last Listing Agent Franchesca Pescatello Prue Realty LLC

    128 MacHine Shop Hill Rd, South Windham, CT 06266
  • 1153 Windham Rd, Windham, CT 06266

    $439,000

    Sold Jun 27, 2025

    1153 Windham Rd, Windham, CT 06266

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

    Last Sold Summary

    • 3% Above List Price
    • $314/SF
    • 162 Days On Market

    Current Estimated Value $455,293

    Last Listing Agent Timothy Morse Alliance Realty LLC

    1153 Windham Rd, Windham, CT 06266
  • 270 S Windham Rd Unit 61, Willimantic, CT 06226

    $112,000

    Sold Aug 29, 2025

    270 S Windham Rd Unit 61, Willimantic, CT 06226

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

    Last Sold Summary

    • $142/SF
    • 34 Days On Market

    Current Estimated Value $107,664

    Last Listing Agent Jenny Adamo KW Legacy Partners

    270 S Windham Rd Unit 61, Willimantic, CT 06226
  • 359 Plains Rd, Willimantic, CT 06226

    $275,000

    Sold Jan 07, 2026

    359 Plains Rd, Willimantic, CT 06226

    • 3 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • Built 1910

    Last Sold Summary

    • 5% Below List Price
    • $145/SF
    • 124 Days On Market

    Current Estimated Value $285,555

    Last Listing Agent Avi Ron SSG Real Estate LLC

    359 Plains Rd, Willimantic, CT 06226
  • 34 S Windham Rd, Willimantic, CT 06226

    $250,000

    Sold Sep 16, 2025

    34 S Windham Rd, Willimantic, CT 06226

    • 3 Beds
    • 1 Bath
    • 1,156 Sq Ft
    • Built 1915

    Last Sold Summary

    • 2% Above List Price
    • $216/SF
    • 5 Days On Market

    Current Estimated Value $246,294

    Last Listing Agent Stephen Girouard CENTURY 21 Shutters & Sails

    34 S Windham Rd, Willimantic, CT 06226
  • 897 Windham Rd, Windham, CT 06266

    $156,000

    Sold Jul 01, 2025

    897 Windham Rd, Windham, CT 06266

    • 2 Beds
    • 1 Bath
    • 1,320 Sq Ft
    • Built 1965

    Last Sold Summary

    • 1% Above List Price
    • $118/SF
    • 52 Days On Market

    Last Listing Agent Michelle Garabedian Home Selling Team

    897 Windham Rd, Windham, CT 06266
  • 121 Highland View Dr, Windham, CT 06266

    $454,000

    Sold Mar 31, 2026

    121 Highland View Dr, Windham, CT 06266

    • 3 Beds
    • 2 Baths
    • 1,200 Sq Ft
    • Built 2025

    Last Sold Summary

    • $378/SF
    • 120 Days On Market

    Last Listing Agent Timothy Morse Alliance Realty LLC

    121 Highland View Dr, Windham, CT 06266
  • 337 S Windham Rd, Willimantic, CT 06226

    $440,000

    Sold Dec 03, 2025

    337 S Windham Rd, Willimantic, CT 06226

    • 4 Beds
    • 2.5 Baths
    • 2,905 Sq Ft
    • Built 1850

    Last Sold Summary

    • 1% Above List Price
    • $151/SF
    • 118 Days On Market

    Current Estimated Value $428,097

    Last Listing Agent Alexia Andrade US Asset Realty

    337 S Windham Rd, Willimantic, CT 06226
  • 40 Sanitarium Rd, South Windham, CT 06266

    $315,000

    Sold Apr 30, 2026

    40 Sanitarium Rd, South Windham, CT 06266

    • 2 Beds
    • 3 Baths
    • 2,214 Sq Ft
    • Built 1955

    Last Sold Summary

    • 8% Above List Price
    • $142/SF
    • 4 Days On Market

    Current Estimated Value $298,980

    Last Listing Agent Martha Poole Carl Guild & Associates

    40 Sanitarium Rd, South Windham, CT 06266
  • 106 Oxbow Dr, Willimantic, CT 06226

    $290,000

    Sold Aug 29, 2025

    106 Oxbow Dr, Willimantic, CT 06226

    • 3 Beds
    • 1.5 Baths
    • 1,784 Sq Ft
    • Built 1978

    Last Sold Summary

    • 8% Below List Price
    • $163/SF
    • 61 Days On Market

    Current Estimated Value $292,132

    Last Listing Agent Sondra Reid Home Selling Team

    106 Oxbow Dr, Willimantic, CT 06226
  • 93 Williams Crossing Rd, Lebanon, CT 06249

    $285,000

    Sold Jun 23, 2025

    93 Williams Crossing Rd, Lebanon, CT 06249

    • 3 Beds
    • 1 Bath
    • 1,152 Sq Ft
    • Built 1971

    Last Sold Summary

    • 4% Above List Price
    • $247/SF
    • 14 Days On Market

    Current Estimated Value $314,209

    Last Listing Agent Amber Jones KW Legacy Partners

    93 Williams Crossing Rd, Lebanon, CT 06249
  • 188 Oxbow Dr, Willimantic, CT 06226

    $275,000

    Sold Oct 24, 2025

    188 Oxbow Dr, Willimantic, CT 06226

    • 2 Beds
    • 2 Baths
    • 804 Sq Ft
    • Built 1977

    Last Sold Summary

    • 3% Below List Price
    • $342/SF
    • 48 Days On Market

    Current Estimated Value $271,417

    Last Listing Agent Peter Baker RE/MAX Bell Park Realty

    188 Oxbow Dr, Willimantic, CT 06226
  • 363 Windham Rd, Willimantic, CT 06226

    $160,000

    Sold Jun 09, 2026

    363 Windham Rd, Willimantic, CT 06226

    • 3 Beds
    • 1 Bath
    • 2,219 Sq Ft
    • Built 1910

    Last Sold Summary

    • 26% Below List Price
    • $72/SF
    • 60 Days On Market

    Current Estimated Value $206,467

    Last Listing Agent Christine Homa Christine Homa

    363 Windham Rd, Willimantic, CT 06226
  • 21 Pigeon Swamp Rd, Lebanon, CT 06249

    $266,500

    Sold Sep 29, 2025

    21 Pigeon Swamp Rd, Lebanon, CT 06249

    • 2 Beds
    • 1 Bath
    • 864 Sq Ft
    • Built 1990

    Last Sold Summary

    • 5% Below List Price
    • $308/SF
    • 80 Days On Market

    Current Estimated Value $278,087

    Last Listing Agent Cathyann Schulte Countryside Realty

    21 Pigeon Swamp Rd, Lebanon, CT 06249
  • Unlisted Address

    $210,000

    Sold Nov 05, 2025

    Unlisted Address

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft
    • Built 1974

    Last Sold Summary

    • 11% Above List Price
    • $219/SF
    • 18 Days On Market

    Current Estimated Value $218,258

    Last Listing Agent Luis Rodriguez Coldwell Banker Realty

    Unlisted Address
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