Homes in ZIP Code 06266

• 

  

  

  /22

  $315,000 Under Contract

  • 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
• 

  $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 $273,466

  Last Listing Agent Franchesca Pescatello Prue Realty LLC

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

  Est $396,892 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

  • 13% Above List Price
  • $188/SF
  • 6 Days On Market

  Last Sold Price $350,000

  Last Listing Agent Danielle Fortier Coldwell Banker Realty
• 

  

  

  /15

  $269,000

  • 5 Beds
  • 1.5 Baths
  • 2,340 Sq Ft

  1008 Windham Rd, South Windham, CT 06266

  Spacious home offering five bedrooms on the upper level along with a versatile main-level room ideal for a home office or playroom, conveniently located to the side of the home. The property features a full bathroom on the main level and a half bathroom on the second floor. Showcasing a unique layout, the home offers convenient entrances from both the upper and lower levels of the paved driveway.

  Michelle Gutierrez Social & Co Realty

  1008 Windham Rd, South 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 $453,102

  Last Listing Agent Timothy Morse Alliance Realty LLC

  1157 Windham Rd, Windham, CT 06266
• 

  Est $346,607 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

  • 5% Above List Price
  • $197/SF
  • 51 Days On Market

  Last Sold Price $330,000

  Last Listing Agent Timothy Morse Alliance Realty LLC
• 

  

  /38

  $320,000 Pending

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  925 Windham Rd, South Windham, CT 06266

  Three bedroom, 1344 Square Foot home ready to move into. Consider the possibilities. Has a walk out basement which could set up for in-law usage. This are is a commerical use zone, could be a great place to set up a business and have a great place to live in or rent. Freshly painted, new hot water heater, new furnace, new chimney liner, new gas fired space heater, new large rear facing deck large

  Clarence Russ Home Selling Team

  925 Windham Rd, 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 $355,438

  Last Listing Agent Lawrence Ross Weichert,REALTORS-Four Corners

  114 Highland View Dr, South Windham, CT 06266
• 

  Est $266,607 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

  • 80% Above List Price
  • $73/SF
  • 11 Days On Market

  Last Sold Price $148,000

  Last Listing Agent Tammy Boles-Senkewitcz Asset Real Estate
• 

  

  /13

  $468,500 Pending

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

  121 Highland View Dr, Windham, CT 06266

  As of 1/21/2026 Under Construction, close to being finished, end of February, expected completion. Weekend and late afternoon showings available. Split Level home, with an open kitchen/dining/living area. Primary bedroom suite with a full bath and walk in closet on one side of the house, with 2 more bedrooms, and a full bath on the other side. Lower level will come complete with a large flex

  Timothy Morse Alliance Realty LLC

  121 Highland View Dr, 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 $239,205

  Last Listing Agent Scott Bayne Century 21 Bay-Mar Realty

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

  Est $246,182 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
• 

  $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 $491,225

  Last Listing Agent Sherry Borgeson Berkshire Hathaway NE Prop.

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

  Est $287,118 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

  • 17% 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
• 

  $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 $462,154

  Last Listing Agent Timothy Morse Alliance Realty LLC

  1145 Windham Rd, Windham, CT 06266
• 

  Est $481,468 Not Listed For Sale

  20 Babcock Hill Rd, South Windham, CT 06266

  • 8 Beds
  • 4,957 Sq Ft
  • Built 1860

  20 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 20% Above List Price
  • $81/SF
  • 87 Days On Market

  Last Sold Price $402,500

  Last Listing Agent Kristen Merrill Countryside Realty
• 

  $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 $335,731

  Last Listing Agent Catherine Deschenes eXp Realty

  106 Highland View Dr, South Windham, CT 06266
• 

  Est $412,502 Not Listed For Sale

  17 Babcock Hill Rd, South Windham, CT 06266

  • 9 Beds
  • 3 Baths
  • 2,567 Sq Ft
  • Built 1914

  17 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 9% Above List Price
  • $148/SF
  • 49 Days On Market

  Last Sold Price $380,000

  Last Listing Agent Diane Bonney William Raveis Real Estate
• 

  $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 $184,096

  Last Listing Agent Franchesca Pescatello Prue Realty LLC

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

  

  /26

  Est $225,953 Not Listed For Sale

  11 Pigeon Swamp Rd, South Windham, CT 06266

  • 4 Beds
  • 1.5 Baths
  • 1,704 Sq Ft
  • Built 1890

  11 Pigeon Swamp Rd, South Windham, CT 06266

  Last Sold Summary

  • 90% Below List Price
  • $70/SF

  Last Sold Price $119,000

  Last Listing Agent James Bradshaw Berkshire Hathaway Home Services
• 

  $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 $435,487

  Last Listing Agent Timothy Morse Alliance Realty LLC

  1153 Windham Rd, Windham, CT 06266
• 

  Est $331,697 Not Listed For Sale

  1089 Windham Rd, South Windham, CT 06266

  • 3 Beds
  • 1 Bath
  • 1,236 Sq Ft
  • Built 1966

  1089 Windham Rd, South Windham, CT 06266

  Last Sold Summary

  • 12% Above List Price
  • $239/SF
  • 65 Days On Market

  Last Sold Price $295,000

  Last Listing Agent Martha Poole Carl Guild & Associates
• 

  $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
• 

  Est $173,704 Not Listed For Sale

  1152 Windham Rd, South Windham, CT 06266

  • 2 Beds
  • 1 Bath
  • 1,046 Sq Ft
  • Built 1930

  1152 Windham Rd, South Windham, CT 06266

  Last Sold Summary

  • 132% Above List Price
  • $72/SF
  • 97 Days On Market

  Last Sold Price $75,000

  Last Listing Agent Amber Alcazar Coldwell Banker Realty
• 

  Est $289,459 Not Listed For Sale

  17 Old Windham Rd, South Windham, CT 06266

  • 3 Beds
  • 1.5 Baths
  • 1,196 Sq Ft
  • Built 1972

  17 Old Windham Rd, South Windham, CT 06266

  Last Sold Summary

  • 26% Above List Price
  • $192/SF
  • 42 Days On Market

  Last Sold Price $230,000

  Last Listing Agent Craig Heyse Coldwell Banker Realty
• 

  Est $273,561 Not Listed For Sale

  12 Type Rd, South Windham, CT 06266

  • 3 Beds
  • 1 Bath
  • 1,296 Sq Ft
  • Built 1956

  12 Type Rd, South Windham, CT 06266

  Last Sold Summary

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

  Last Sold Price $195,000

  Last Listing Agent Michelle Garabedian Home Selling Team
• 

  Est $214,590 Not Listed For Sale

  45 Babcock Hill Rd, South Windham, CT 06266

  • 2 Beds
  • 1 Bath
  • 794 Sq Ft
  • Built 1890

  45 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 43% Above List Price
  • $189/SF
  • 5 Days On Market

  Last Sold Price $150,000

  Last Listing Agent Amber Jones KW Legacy Partners
• 

  Est $331,942 Not Listed For Sale

  27 Babcock Hill Rd, South Windham, CT 06266

  • 3 Beds
  • 1.5 Baths
  • 1,890 Sq Ft
  • Built 1850

  27 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 30% Above List Price
  • $135/SF
  • 5 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Jeanne Crum Home Selling Team
• 

  Est $285,674 Not Listed For Sale

  69 Babcock Hill Rd, South Windham, CT 06266

  • 4 Beds
  • 2 Baths
  • 1,903 Sq Ft
  • Built 1890

  69 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 30% Above List Price
  • $116/SF
  • 38 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Jennifer Alix Berkshire Hathaway Home Services
• 

  Est $194,103 Not Listed For Sale

  50 Pigeon Swamp Rd, South Windham, CT 06266

  • 3 Beds
  • 1 Bath
  • 1,245 Sq Ft
  • Built 1888

  50 Pigeon Swamp Rd, South Windham, CT 06266

  Last Sold Summary

  • 76% Above List Price
  • $88/SF
  • 38 Days On Market

  Last Sold Price $110,000

  Last Listing Agent Debra Prevost Kazantzis Real Estate, LLC
• 

  Est $280,564 Not Listed For Sale

  27 Type Rd, South Windham, CT 06266

  • 4 Beds
  • 1 Bath
  • 1,218 Sq Ft
  • Built 1865

  27 Type Rd, South Windham, CT 06266

  Last Sold Summary

  • 40% Above List Price
  • $164/SF
  • 4 Days On Market

  Last Sold Price $199,900

  Last Listing Agent Tia Mccloskey William Raveis Real Estate
• 

  Est $320,548 Not Listed For Sale

  32 Sanitarium Rd, South Windham, CT 06266

  • 3 Beds
  • 2 Baths
  • 2,148 Sq Ft
  • Built 1971

  32 Sanitarium Rd, South Windham, CT 06266

  Last Sold Summary

  • 31% Above List Price
  • $114/SF
  • 33 Days On Market

  Last Sold Price $245,000

  Last Listing Agent Lawrence Ross Weichert Corporate
• 

  Est $320,797 Not Listed For Sale

  249 Highland View Dr, South Windham, CT 06266

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft
  • Built 1966

  249 Highland View Dr, South Windham, CT 06266

  Last Sold Summary

  • 26% Above List Price
  • $190/SF
  • 4 Days On Market

  Last Sold Price $255,000

  Last Listing Agent Lynsie M. White KW Legacy Partners
• 

  Est $234,356 Not Listed For Sale

  158 Babcock Hill Rd, South Windham, CT 06266

  • 3 Beds
  • 1 Bath
  • 1,032 Sq Ft
  • Built 1964

  158 Babcock Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 39% Above List Price
  • $163/SF
  • 10 Days On Market

  Last Sold Price $168,000

  Last Listing Agent Patrick M Prue Prue Realty LLC
• 

  Not Listed For Sale

  31 Main St, South Windham, CT 06266

  • 3,734 Sq Ft
  • Built 1877

  31 Main St, South Windham, CT 06266

  Last Sold Summary

  • $87/SF
  • 95 Days On Market

  Last Sold Price $325,000

  Last Listing Agent Samuel Peralta Berkshire Hathaway Home Services
• 

  Est $424,580 Not Listed For Sale

  172 MacHine Shop Hill Rd, South Windham, CT 06266

  • 3 Beds
  • 2.5 Baths
  • 2,412 Sq Ft
  • Built 1985

  172 MacHine Shop Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 93% Above List Price
  • $91/SF
  • 120 Days On Market

  Last Sold Price $220,000

  Last Listing Agent Julie Landon-Stewart Weichert Corporate
• 

  Est $393,487 Not Listed For Sale

  19 Pigeon Swamp Rd, South Windham, CT 06266

  • 3 Beds
  • 2.5 Baths
  • 1,994 Sq Ft
  • Built 1890

  19 Pigeon Swamp Rd, South Windham, CT 06266

  Last Sold Summary

  • 169% Above List Price
  • $73/SF
  • 9 Days On Market

  Last Sold Price $146,500

  Last Listing Agent Lisa Sader-Goede Aspen Realty Group
• 

  Est $369,939 Not Listed For Sale

  16 Highland View Dr, South Windham, CT 06266

  • 4 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1965

  16 Highland View Dr, South Windham, CT 06266

  Last Sold Summary

  • 70% Above List Price
  • $111/SF
  • 45 Days On Market

  Last Sold Price $217,000

  Last Listing Agent Rick Loranger Coldwell Banker Realty
• 

  Est $288,859 Not Listed For Sale

  36 MacHine Shop Hill Rd, South Windham, CT 06266

  • 3 Beds
  • 2 Baths
  • 1,762 Sq Ft
  • Built 1912

  36 MacHine Shop Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • 59% Above List Price
  • $103/SF
  • 34 Days On Market

  Last Sold Price $181,650

  Last Listing Agent Daniel Kildea Sellstate Leading Edge Realty
• 

  Not Listed For Sale

  64 MacHine Shop Hill Rd, South Windham, CT 06266

  • 2 Beds
  • 1 Bath
  • 1,400 Sq Ft
  • Built 1800

  64 MacHine Shop Hill Rd, South Windham, CT 06266

  Last Sold Summary

  • $109/SF
  • 42 Days On Market

  Last Sold Price $152,500

  Last Listing Agent Rick Loranger Coldwell Banker Realty

Showing Results 1 - 40, Page 1 of 6