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

  

  Anthony D'Amore

  eXp Realty

  (860) 530-6511

  235 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
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  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
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  /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
• 

  $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
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  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
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  /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
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  $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
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  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
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  /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
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  $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
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  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
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  /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
• 

  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
• 

  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
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  $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
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  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
• 

  $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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