Windham, CT Homes

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  /32

  $275,000

  $100K PRICE DROP Pending

  • 7 Beds
  • 4 Baths
  • 3,963 Sq Ft

  129 Valley St, Windham, CT 06226

  Mixed-use investment property with multiple income streams and strong value-add potential. The property is zoned B-1A and currently configured with two occupied residential units generating income, plus two additional gutted residential units with plumbing in place, ready for build-out. The property also includes a commercial storefront with a separate entrance, offering flexibility for a variety

  Kyle West eXp Realty

  129 Valley St, Windham, 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
• 

  Est $258,514

  Not Listed For Sale

  123 Union St, Willimantic, CT 06226

  • 4 Beds
  • 1 Bath
  • 1,420 Sq Ft
  • Built 1900

  123 Union St, Willimantic, CT 06226

  Last Sold Summary

  • 11 Days On Market

  Last Listing Agent Stephen Daly KW Legacy Partners
• 

  

  

  /31

  $289,000

  Pending

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft

  1 Gem Dr, Willimantic, CT 06226

  Welcome to 1 Gem Drive. This well cared for 3-bedroom, 2-bath raised ranch offers comfort, charm, and space to enjoy both inside and out. The home features additional finished space in the lower level, perfect for a family room, home office, or guest area, complete with a full bath. Step into a bright and inviting layout designed for easy living, with plenty of room for both relaxing and

  Stephen Galinat Home Selling Team

  1 Gem Dr, Willimantic, CT 06226
• 

  $395,000

  Sold Feb 06, 2026

  127 Plains Rd, Windham, CT 06280

  • 4 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 1985

  Last Sold Summary

  • $232/SF
  • 70 Days On Market

  Current Estimated Value $392,530

  Last Listing Agent Pat Malek First Choice Realty

  127 Plains Rd, Windham, CT 06280
• 

  Est $325,035

  Not Listed For Sale

  225 Lewiston Ave, Willimantic, CT 06226

  • 3 Beds
  • 1.5 Baths
  • 2,085 Sq Ft
  • Built 1890

  225 Lewiston Ave, Willimantic, CT 06226

  Last Sold Summary

  • 27 Days On Market

  Last Listing Agent Stephen Daly KW Legacy Partners
• 

  

  /18

  $289,500

  $10K PRICE DROP

  • 3 Beds
  • 1.5 Baths
  • 1,530 Sq Ft

  10 Potter St, Willimantic, CT 06226

  Check out this 1920s Dutch Colonial with many new upgrades! This property is on a small private lot that is easy to maintain. The front and rear porches allow plenty of opportunity to enjoy the yard and the neighborhood. The property overlooks Rotary Field and is within walking distance of Jillson Square. Property recently had a new oil tank and copper supply lines installed. Come take a look!

  Ryan King Aspen Realty Group

  10 Potter St, 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 $297,363

  Last Listing Agent Christy Lofstrom Driscoll ERA Blanchard & Rossetto

  21 Russ Rd, Willimantic, CT 06226
• 

  Est $280,840

  Not Listed For Sale

  41 Gifford Ave, Willimantic, CT 06226

  • 4 Beds
  • 2 Baths
  • 1,565 Sq Ft
  • Built 1930

  41 Gifford Ave, Willimantic, CT 06226

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Amber Alcazar Coldwell Banker Realty
• 

  

  /40

  $399,000

  $50K PRICE DROP Pending

  • 5 Beds
  • 2.5 Baths
  • 2,816 Sq Ft

  7 Sycamore Terrace, Windham, CT 06280

  Welcome Home to this beautifully updated 5-bedroom Colonial tucked away on a dead end road on a private, wooded .78-acre lot. Step inside to a sunlit living room where the fireplace sets the tone for cozy New England evenings, flowing seamlessly into the formal dining room and updated kitchen - ideal for hosting holidays or casual weeknight meals. Just off the main level, you will find a

  John M Varrone, Terry Varrone eXp Realty

  7 Sycamore Terrace, Windham, CT 06280
• 

  $205,000

  Sold Dec 05, 2025

  29 Kathleen Dr Unit 5E, Willimantic, CT 06226

  • 2 Beds
  • 1.5 Baths
  • 998 Sq Ft
  • Built 1987

  Last Sold Summary

  • 3% Above List Price
  • $205/SF
  • 3 Days On Market

  Current Estimated Value $206,738

  Last Listing Agent Barbara Sullivan Sullivan Real Estate Group

  29 Kathleen Dr Unit 5E, Willimantic, CT 06226
• 

  Est $189,338

  Not Listed For Sale

  310 Scotland Rd, Windham, CT 06280

  • 1 Bed
  • 1 Bath
  • 555 Sq Ft
  • Built 1958

  310 Scotland Rd, Windham, CT 06280

  Last Sold Summary

  • 21 Days On Market

  Last Listing Agent Tony Martin Home Pro Real Estate
• 

  

  /3

  $40,000

  Pending

  • Land
  • 1.08 Acres
  • $37,037 per Acre

  248 Tuckie Rd, Windham, CT 06256

  Buildable 1.08 acre lot in a nice location in North Windham. Close to conveniences, yet off the beaten path. Just minutes to shopping and dining, the Mansfield Hollow Dam Walk, Joshuas Trust land, and Windham Golf Course, just to name a few nearby amenities. A wonderful spot to build your new home!

  Sue Esposito Home Selling Team

  248 Tuckie Rd, Windham, CT 06256
• 

  $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 $376,314

  Last Listing Agent Nikki Defrancesco Coldwell Banker Realty

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

  Est $480,252

  Not Listed For Sale

  67 Anna Maria Ln, Windham, CT 06280

  • 3 Beds
  • 2.5 Baths
  • 2,826 Sq Ft
  • Built 2005

  67 Anna Maria Ln, Windham, CT 06280

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Dara Dominique Ferrigno-Storrs, REALTORS LLC
• 

  

  /32

  $220,000

  Under Contract

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  37 Spring View Ln, Willimantic, CT 06226

  Opportunity awaits at this ranch-style home tucked away on a cul-de-sac in a convenient Willimantic location. Ready for renovation and personal updates, this property offers excellent potential for investors, contractors, or buyers looking to build sweat equity. The functional floor plan features a comfortable living area, three bedrooms, one full bath, and a layout that provides flexibility for

  Sue Esposito Home Selling Team

  37 Spring View Ln, Willimantic, CT 06226
• 

  $160,000

  Sold Sep 05, 2025

  29 Kathleen Dr Unit 9D, Willimantic, CT 06226

  • 2 Beds
  • 1 Bath
  • 1,035 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Above List Price
  • $155/SF
  • 102 Days On Market

  Current Estimated Value $176,123

  Last Listing Agent The Bowes Team RE/MAX on the Bay

  29 Kathleen Dr Unit 9D, Willimantic, CT 06226
• 

  Est $364,220

  Not Listed For Sale

  251 Walnut St, Willimantic, CT 06226

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft
  • Built 1930

  251 Walnut St, Willimantic, CT 06226

  Last Sold Summary

  • 5 Days On Market

  Last Listing Agent Sue Esposito Home Selling Team
• 

  

  /25

  $90,000

  Pending

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft

  5 Jessie Ln, North Windham, CT 06256

  This clean and bright unit has a nice open floor plan The kitchen comes fully applianced and has lots of cabinets and counter space. Plenty of room for your table. Open concept to living room, all with nice flooring. The primary bedroom and full bath with soaking tub and shower are on one side, with the second bedroom and full bath on the other side. Laundry is conveniently placed. There is a

  Cathy Duprey Duprey Real Estate, LLC

  5 Jessie Ln, North Windham, CT 06256
• 

  $197,000

  Sold Jun 16, 2026

  19 Boston Post Rd, North Windham, CT 06256

  • 5 Beds
  • 2.5 Baths
  • 1,480 Sq Ft
  • Built 1885

  Last Sold Summary

  • 1% Below List Price
  • $133/SF
  • 8 Days On Market

  Current Estimated Value $209,533

  Last Listing Agent Jolanta Rojek eXp Realty

  19 Boston Post Rd, North Windham, CT 06256
• 

  Est $386,846

  Not Listed For Sale

  29 Pearl St, Willimantic, CT 06226

  • 10 Beds
  • 3 Baths
  • 3,237 Sq Ft
  • Built 1880

  29 Pearl St, Willimantic, CT 06226

  Last Sold Summary

  • 15 Days On Market

  Last Listing Agent Marta Lisowska KW Legacy Partners
• 

  

  /38

  $229,000

  • 2 Beds
  • 1.5 Baths
  • 1,210 Sq Ft

  366 Ash St Unit 1, Willimantic, CT 06226

  End unit condo in one of the most sought-after complexes in Nice. Features include a modern kitchen with granite countertops, tile backsplash, and ample cabinet storage. The open-concept living and dining area boasts vaulted ceilings and an abundance of natural light from large windows. Main-level half bath for convenience. Upstairs, the spacious primary bedroom offers vaulted ceilings, a

  Jeanne Crum Home Selling Team

  366 Ash St Unit 1, Willimantic, CT 06226
• 

  $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 $255,757

  Last Listing Agent Scott Bayne Century 21 Bay-Mar Realty

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

  Est $309,271

  Not Listed For Sale

  4 Jordan Ln, North Windham, CT 06256

  • 4 Beds
  • 1 Bath
  • 1,412 Sq Ft
  • Built 1936

  4 Jordan Ln, North Windham, CT 06256

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Stephen Daly KW Legacy Partners
• 

  

  /26

  $269,900

  Pending

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  41 Hilltop Dr Unit 48, North Windham, CT 06256

  Welcome to Oak Forest Village! This well-maintained 2-bedroom, 2-bath detached condo offers comfortable one-level living in a quiet, well-kept community and is ready for a new owner. The main floor features a bright living room, dining area, and a kitchen with center island seating, all filled with natural light. Enjoy the private deck overlooking a peaceful wooded setting, perfect for relaxing

  Katherine Hernandez Lantigua KW Legacy Partners

  41 Hilltop Dr Unit 48, North Windham, CT 06256
• 

  $74,000

  Sold Aug 22, 2025

  11 Elizabeth Ln, North Windham, CT 06256

  • 3 Beds
  • 1.5 Baths
  • 924 Sq Ft
  • Built 1997

  Last Sold Summary

  • 14% Below List Price
  • $80/SF
  • 56 Days On Market

  Last Listing Agent Rebecca Zager The Agency

  11 Elizabeth Ln, North Windham, CT 06256
• 

  Est $111,517

  Not Listed For Sale

  270 S Windham Rd Unit 52, Willimantic, CT 06226

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

  270 S Windham Rd Unit 52, Willimantic, CT 06226

  Last Sold Summary

  • 82 Days On Market

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

  

  /6

  $215,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,423 Sq Ft

  118 Windham Center Rd, Windham, CT 06280

  This home was built in 1740. Still has many original features yet it needs work. Should you be looking for spacious rooms, fireplace in LR and on each bedroom upstairs that work, then take a look at it. The kitchen is in the back ell. It is a huge kitchen with your open design in place. It has many crannies, closets, special nooks and really will charm you for its age. There are fireplaces in the

  Art Kostapapas Weichert,REALTORS-Four Corners

  118 Windham Center Rd, Windham, CT 06280
• 

  $265,000

  Sold Jun 26, 2026

  12 Ardman Dr, Willimantic, CT 06226

  • 3 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1950

  Last Sold Summary

  • 8% Above List Price
  • $234/SF
  • 5 Days On Market

  Current Estimated Value $242,663

  Last Listing Agent Lisa Sader-Goede Aspen Realty Group

  12 Ardman Dr, Willimantic, CT 06226
• 

  Est $323,720

  Not Listed For Sale

  74 Holbrook Ave, Willimantic, CT 06226

  • 4 Beds
  • 2 Baths
  • 1,860 Sq Ft
  • Built 1937

  74 Holbrook Ave, Willimantic, CT 06226

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Marta Lisowska KW Legacy Partners
• 

  

  /28

  $399,999

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft

  187 Tuckie Rd, North Windham, CT 06256

  Welcome to your own retreat! Perfectly positioned on a gorgeous, level 1 acre lot surrounded by mature trees, this beautifully maintained Cape offers the peaceful lifestyle you've been dreaming of. From the moment you arrive, you'll picture slow mornings spent on the charming front porch w/a cup of coffee and your favorite book, soaking in the quiet beauty that surrounds you. Out back, you'll

  Meghan Wininger Real Broker CT, LLC

  187 Tuckie Rd, North Windham, CT 06256
• 

  $436,000

  Sold Feb 13, 2026

  61 Oak St, Willimantic, CT 06226

  • 7 Beds
  • 4 Baths
  • 2,769 Sq Ft
  • Built 1890

  Last Sold Summary

  • 3% Above List Price
  • $157/SF
  • 3 Days On Market

  Current Estimated Value $434,276

  Last Listing Agent Julienne Jaber KW Legacy Partners

  61 Oak St, Willimantic, CT 06226
• 

  Est $274,264

  Not Listed For Sale

  12 Connor St, Willimantic, CT 06226

  • 3 Beds
  • 1 Bath
  • 1,248 Sq Ft
  • Built 1927

  12 Connor St, Willimantic, CT 06226

  Last Sold Summary

  • 18 Days On Market

  Last Listing Agent Irene Adams Signature Properties of N.E.
• 

  

  /11

  $269,000

  Open Sat 1PM - 2:30PM

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

  1008 Windham Rd, South Windham, CT 06266

  Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but

  Victoria Schroeder Kazantzis Real Estate, LLC

  1008 Windham Rd, South Windham, CT 06266
• 

  $249,000

  Sold Dec 30, 2025

  10 North Rd, Windham, CT 06280

  • 2 Beds
  • 1.5 Baths
  • 1,380 Sq Ft
  • Built 1780

  Last Sold Summary

  • $180/SF
  • 95 Days On Market

  Current Estimated Value $255,170

  Last Listing Agent Taylor Gildein Re/Max Results

  10 North Rd, Windham, CT 06280
• 

  Est $349,203

  Not Listed For Sale

  469 Pleasant St, Willimantic, CT 06226

  • 6 Beds
  • 3 Baths
  • 2,947 Sq Ft
  • Built 1890

  469 Pleasant St, Willimantic, CT 06226

  Last Sold Summary

  • 3 Days On Market

  Last Listing Agent Matthew Noren RE/MAX Bell Park Realty
• 

  

  /39

  $235,000

  Pending

  • 4 Beds
  • 1.5 Baths
  • 1,922 Sq Ft

  257 Walnut St, Willimantic, CT 06226

  Historic Hill Colonial with Timeless Charm & Endless Potential Nestled on a desirable corner lot in the Historic Hill section of town, this stately Colonial is filled with classic character and ready for its next chapter. A detached two-car garage and beautiful architectural details make this home a rare opportunity. The welcoming kitchen features a charming built-in breakfast nook and convenient

  Jeanne Crum Home Selling Team

  257 Walnut St, Willimantic, CT 06226
• 

  $350,000

  Sold Dec 09, 2025

  176 Windham Rd, Willimantic, CT 06226

  • 8 Beds
  • 3 Baths
  • 3,073 Sq Ft
  • Built 1910

  Last Sold Summary

  • 8% Below List Price
  • $114/SF
  • 71 Days On Market

  Current Estimated Value $359,286

  Last Listing Agent Gregory Leone Coldwell Banker Realty

  176 Windham Rd, Willimantic, CT 06226
• 

  Est $342,113

  Not Listed For Sale

  95 Mullen Hill Rd, Windham, CT 06280

  • 3 Beds
  • 1.5 Baths
  • 1,704 Sq Ft
  • Built 1936

  95 Mullen Hill Rd, Windham, CT 06280

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Adam Mallory Senna Realty Group, LLC
• 

  

  /19

  $219,000

  $19K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,078 Sq Ft

  129 Walnut St, Willimantic, CT 06226

  Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a

  Lisa Therecka Therecka & Associates LLC

  129 Walnut St, Willimantic, CT 06226

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