Windham, CT Homes

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  /22

  $67,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft

  16 Pond Way, North Windham, CT 06256

  3% Interest, $0 Down Financing Available! Welcome home to your spacious 2 bedroom, 2 full bathroom open floor plan at 16 Pond Way, North Windham (Stonegate Manor). First floor laundry, mudroom with backyard access, and 1,218 sqft (rarely found at this affordable price point). This home is perfect for first-time buyers, downsizers, and value-seekers looking for affordable homeownership in a

  

  Stephen Daly

  KW Legacy Partners

  (860) 864-5536

  16 Pond Way, North Windham, CT 06256
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  /16

  $2,350 total monthly price

  • 3 Beds
  • 2 Baths
  • 1,000 Sq Ft
  • House for Rent

  736 Main St, Willimantic, CT 06226

  Downtown Willimantic apartment located on Main Street within walking distance to restaurants, shops, and local amenities. Features new energy-efficient mini split heating and cooling for year-round comfort and lower utility costs. Convenient location just minutes from Eastern Connecticut State University and a short drive to UConn Storrs. Easy access to Route 66 and Route 32 for commuting. Enjoy

  

  Adam Duffy

  O'Rourke Grp RE Professionals

  (860) 321-6587

  736 Main St, Willimantic, CT 06226
• 

  $70,000 Sold Aug 18, 2025

  26 Jacqueline Ln, North Windham, CT 06256

  • 2 Beds
  • 2 Baths
  • 924 Sq Ft
  • Built 1987

  Last Sold Summary

  • $76/SF
  • 34 Days On Market

  Last Listing Agent Derek Greene Derek Greene

  26 Jacqueline Ln, North Windham, CT 06256
• 

  Est $377,640 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

  • 19% 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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  /10

  $324,900

  • 3 Beds
  • 1.5 Baths
  • 1,277 Sq Ft

  11 Woodland Dr, Windham, CT 06280

  New Photos Coming Soon! Welcome to 11 Woodland Drive in Windham, Connecticut. This home has all the charm and character one would find in rural Windham County. The exterior of this property boasts a lovely manicured yard with landscaped bushes, perennial flowers and vegetables, fruit trees, and native plants. The interior of this home has three bedrooms and a large laundry room that can be

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 579-1208

  11 Woodland Dr, Windham, CT 06280
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  /16

  $1,750 total monthly price

  • 2 Beds
  • 1 Bath
  • 2,652 Sq Ft
  • House for Rent

  80 North St, Willimantic, CT 06226

  Available for rent! This renovated 2-Bedroom Apartment in the heart of Willimantic. This updated 2-bedroom, 1-bathroom apartment is located on the first floor of 80 North Street and is approximately 1,020 sq. ft. It features 2 generous bedrooms, 1 full modern bathroom, and a separate dining and living room. On-street parking is available. There is quick access to local shops, dining, ECSU, and a

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 364-6311

  80 North St, Willimantic, CT 06226
• 

  $255,000 Sold Jan 22, 2026

  Unlisted Address

  • 3 Beds
  • 2.5 Baths
  • 2,248 Sq Ft
  • Built 1969

  Last Sold Summary

  • 18% Below List Price
  • $113/SF
  • 205 Days On Market

  Current Estimated Value $290,106

  Last Listing Agent Valerie Yankus Property Shoppe, LLC

  Unlisted Address
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  Est $346,604 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

  • $165/SF
  • 27 Days On Market

  Last Sold Price $345,000

  Last Listing Agent Stephen Daly KW Legacy Partners
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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
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  /35

  $1,085 - $1,830 total monthly price

  Colonial Townhouse Apartments

  Studio - 2 Beds

  29 Foster Dr, Willimantic, CT 06226

  Come experience life at Colonial Townhouse Apartments! Lots of improvements have been made to the property to make us energy efficient with a modern appearance. This includes new windows, new siding, new EV chargers, fresh signage, and upgraded apartments. You'll get the most value for your money around! Located on the WRTD bus line for easy access to all the area has to offer. **Screening Fee is

  29 Foster Dr, Willimantic, CT 06226
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  $331,000 Sold Mar 16, 2026

  165 Ballamahack Rd, Windham, CT 06280

  • 3 Beds
  • 1.5 Baths
  • 1,382 Sq Ft
  • Built 1953

  Last Sold Summary

  • 10% Above List Price
  • $240/SF
  • 7 Days On Market

  Current Estimated Value $196,952

  Last Listing Agent Anthony La Penna Exceptional Real Estate LLC

  165 Ballamahack Rd, Windham, CT 06280
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  Est $317,117 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

  • 2% Above List Price
  • $220/SF
  • 7 Days On Market

  Last Sold Price $310,000

  Last Listing Agent Stephen Daly KW Legacy Partners
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  /35

  $299,900

  • 4 Beds
  • 2 Baths
  • 2,540 Sq Ft

  50 Selden St, Willimantic, CT 06226

  Discover the opportunity to make this classic Colonial-style single-family home your own. Featuring 4 generously sized bedrooms and 2 full bathrooms, this property offers spacious rooms filled with natural light and a layout ready for your personal touch. Situated just minutes from Eastern Connecticut State University and the local hospital, this home is conveniently located near schools,

  Patrizia Puccia KW Legacy Partners

  50 Selden St, Willimantic, CT 06226
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  /4

  $1,050 total monthly price

  • 1 Bath
  • 3,311 Sq Ft
  • Apartment for Rent

  219 Pleasant St Unit 1B, Windham, CT 06226

  First-floor studio apartment available for immediate occupancy. This unit features a functional layout with easy access and convenient off-street parking. Pets may be considered on a case-by-case basis. No smoking permitted. Ideal for those seeking a straightforward, low-maintenance living space with close proximity to local shops, dining, and major routes.

  Michelle Mandel Carl Guild & Associates

  219 Pleasant St Unit 1B, Windham, CT 06226
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  $50,000 Sold Jul 29, 2025

  36 Fairway Dr, Windham, CT 06256

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft
  • Built 1971

  Last Sold Summary

  • 9% Below List Price
  • $74/SF
  • 81 Days On Market

  Last Listing Agent Erica Molochnick RbRE, LLC

  36 Fairway Dr, Windham, CT 06256
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  Est $359,920 Not Listed For Sale

  46 Quercus Ave, Willimantic, CT 06226

  • 4 Beds
  • 3 Baths
  • 2,930 Sq Ft
  • Built 1900

  46 Quercus Ave, Willimantic, CT 06226

  Last Sold Summary

  • 7% Above List Price
  • $115/SF
  • 63 Days On Market

  Last Sold Price $337,000

  Last Listing Agent Brian McCarthy Home Selling Team
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  /37

  $299,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,708 Sq Ft

  96 Mcdermott Ave, Willimantic, CT 06226

  *Highest & Best Offer Deadline on Tuesday, 3/10/26, 10:00 am.* This beautifully updated and wellmaintained home offers a flexible layout in a convenient neighborhood setting. The main level features comfortable living spaces and three bedrooms with a full bath, while the finished lower level includes a spacious additional room that works perfectly as a fourth bedroom, family room, or multipurpose

  Sue Esposito Home Selling Team

  96 Mcdermott Ave, Willimantic, CT 06226
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  /5

  $1,290 - $2,386 per month plus fees

  Artspace Windham

  1 - 3 Beds

  480 Main St, Willimantic, CT 06226

  480 Main St, Willimantic, CT 06226
• 

  $45,000 Sold Jun 23, 2025

  206 Boston Post Rd, Windham, CT 06256

  • Land
  • 0.41 Acre
  • $109,756 per Acre

  Last Sold Summary

  • 32% Below List Price
  • 12 Days On Market

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

  206 Boston Post Rd, Windham, CT 06256
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  Est $363,447 Not Listed For Sale

  371 Prospect St, Willimantic, CT 06226

  • 4 Beds
  • 2 Baths
  • 3,180 Sq Ft
  • Built 1908

  371 Prospect St, Willimantic, CT 06226

  Last Sold Summary

  • 4% Above List Price
  • $109/SF
  • 4 Days On Market

  Last Sold Price $348,000

  Last Listing Agent Sadierose Lemire Drawbridge Realty
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  /20

  $359,900 Under Contract

  • 3 Beds
  • 3 Baths
  • 2,128 Sq Ft

  91 Insalaco Dr, Windham, CT 06280

  This beautiful colonial is situated on a private lot in a wonderful cup-de-sac neighborhood setting. A unique aspect of this home is that it has 2 primary bedroom suites with one being on the first floor allowing for handicap accessibility if needed. Both bedroom suites feature full bathrooms, walk-in closets, hardwood floors and tile in the baths. You will love the spacious first floor open

  Mike Thompson Countryside Realty

  91 Insalaco Dr, Windham, CT 06280
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  /10

  $1,700 total monthly price

  • 2 Beds
  • 1 Bath
  • 3,311 Sq Ft
  • Apartment for Rent

  219 Pleasant St Unit 3, Windham, CT 06226

  Second-floor 2-bedroom apartment available for immediate occupancy. This unit features a functional, spacious layout with two separate bedrooms. Off-street parking is included for convenience. Pets may be considered on a case-by-case basis. No smoking permitted. Conveniently located near local shops, dining, and major routes for easy access to everyday essentials and commuting.

  Michelle Mandel Carl Guild & Associates

  219 Pleasant St Unit 3, Windham, CT 06226
• 

  $154,000 Sold Jul 18, 2025

  1 Circle Dr, North Windham, CT 06256

  • 3 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $107/SF
  • 252 Days On Market

  Last Listing Agent Ryan Smithwick eRealty Advisors, Inc.

  1 Circle Dr, North Windham, CT 06256
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  Est $320,225 Not Listed For Sale

  623 Boston Post Rd, North Windham, CT 06256

  • 5 Beds
  • 1.5 Baths
  • 1,440 Sq Ft
  • Built 1915

  623 Boston Post Rd, North Windham, CT 06256

  Last Sold Summary

  • 4% Above List Price
  • $213/SF
  • 41 Days On Market

  Last Sold Price $307,000

  Last Listing Agent Kimberly Gates Gateway Real Estate
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  /29

  $285,000

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  119 Quercus Ave, Willimantic, CT 06226

  Tucked into The Oaks, one of Willimantic's most beloved neighborhoods, this 1890s Cape Cod is a home that feels instantly welcoming. Built by the Willimantic Linen Company, it reflects a simpler time, beginning with a covered front porch and a thoughtfully scaled interior that feels comfortable and inviting. The 1,160 square foot home offers three bedrooms and a cozy living room featuring the

  Kristen Kaskela Berkshire Hathaway NE Prop.

  119 Quercus Ave, Willimantic, CT 06226
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  /24

  $1,600 - $1,750 total monthly price

  Ivy Garden Apartments

  2 Beds

  84 Ash St, Willimantic, CT 06226

  Ivy Gardens is a gorgeous Townhouse-style community located in the heart of Willimantic, close to ECSU and UConn. Our rent pricing includes heat, hot water, assigned parking and visitors parking which is through out the community. We also have laundry on-site and feature some units with private laundry centers. Ivy Gardens features on-site management and maintenance, as well as emergency

  84 Ash St, Willimantic, CT 06226
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  $225,000 Sold Nov 11, 2025

  366 Ash St Unit 2, Willimantic, CT 06226

  • 2 Beds
  • 1.5 Baths
  • 1,210 Sq Ft
  • Built 1988

  Last Sold Summary

  • $186/SF
  • 57 Days On Market

  Current Estimated Value $223,265

  Last Listing Agent Deb Chabot RE/MAX One

  366 Ash St Unit 2, Willimantic, CT 06226
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  Est $355,134 Not Listed For Sale

  256 Tuckie Rd, North Windham, CT 06256

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 1968

  256 Tuckie Rd, North Windham, CT 06256

  Last Sold Summary

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

  Last Sold Price $343,000

  Last Listing Agent Sue Esposito Home Selling Team
• 

  

  /37

  $299,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 1 Bath
  • 1,423 Sq Ft

  170 Windham Center Rd, Windham, CT 06280

  Tucked into the peaceful countryside of South Windham, CT, this move-in-ready 1,423-square-foot home offers a wonderful blend of private country living and modern practical updates. Completely refreshed from top to bottom-including the peace of mind of all new plumbing-the house sits on a beautiful, level lot featuring quiet water views, giving you a sense of rural escape while staying just a

  Brenda Chubbuck Berkshire Hathaway NE Prop.

  170 Windham Center Rd, Windham, CT 06280
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  /10

  $2,300 total monthly price

  • 4 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • House for Rent

  53 Lynwood Dr, Willimantic, CT 06226

  Heat, Hot Water, Washer and Dryer included with this 4 bedroom cape cod style home which borders ECSU's campus and is also minutes away from UConn. The first floor features 2 of the bedrooms, the full bathroom, and a bonus 3 season room. The other 2 spacious bedrooms are located on the second floor. The landlord takes care of the lawn, while all other utilities and snow removal are the

  Adam Zak Century 21 Classic Homes

  53 Lynwood Dr, Willimantic, CT 06226
• 

  $470,000 Sold Mar 23, 2026

  97 Bass Rd, Windham, CT 06280

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft
  • Built 1991

  Last Sold Summary

  • 5% Above List Price
  • $191/SF
  • 39 Days On Market

  Current Estimated Value $446,916

  Last Listing Agent Lindsey Niarhakos RE/MAX One

  97 Bass Rd, Windham, CT 06280
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  Est $538,696 Not Listed For Sale

  134 Church St, Windham, CT 06226

  • 20 Beds
  • 5 Baths
  • 6,000 Sq Ft
  • Built 1900

  134 Church St, Windham, CT 06226

  Last Sold Summary

  • 4% Above List Price
  • $86/SF
  • 52 Days On Market

  Last Sold Price $517,300

  Last Listing Agent Brian McCarthy Home Selling Team
• 

  

  /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
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  /13

  $1,050 - $1,700 per month plus fees

  560 on Main

  Studio - 2 Beds

  560 Main St, Willimantic, CT 06226

  Overlooking scenic Willimantic Falls and adjacent to the famous Frog Bridge, 560 On Main features spacious apartments complete with an artistic, warehouse, loft feel and unique floor plans thoughtfully designed within the walls of the historic Willimantic thread mill. 560 on Main provides each resident with the ultimate in comfort and enjoyment by offering state of the art amenities, outstanding

  560 Main St, Willimantic, CT 06226
• 

  $280,000 Sold Jun 11, 2025

  211 Roanoak Ave, Willimantic, CT 06226

  • 4 Beds
  • 1 Bath
  • 1,312 Sq Ft
  • Built 1979

  Last Sold Summary

  • 4% Above List Price
  • $213/SF
  • 2 Days On Market

  Current Estimated Value $284,287

  Last Listing Agent Sharon Watson Stokland List N Show LLC

  211 Roanoak Ave, Willimantic, CT 06226
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  Est $470,540 Not Listed For Sale

  226 Jackson St, Windham, CT 06226

  • 10 Beds
  • 5.5 Baths
  • 3,540 Sq Ft
  • Built 1900

  226 Jackson St, Windham, CT 06226

  Last Sold Summary

  • 3% Above List Price
  • $129/SF
  • 84 Days On Market

  Last Sold Price $457,700

  Last Listing Agent Brian McCarthy Home Selling Team
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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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  /6

  $1,650 total monthly price

  • 3 Beds
  • 1 Bath
  • 2,939 Sq Ft
  • Apartment for Rent

  260 Summit St Unit 2B, Windham, CT 06226

  3-bedroom, 1-bath second-floor apartment available for immediate occupancy featuring an eat-in kitchen. Conveniently located near local shops, restaurants, parks, and commuter routes. No smoking permitted. Pets considered on a case-by-case basis.

  Michelle Mandel Carl Guild & Associates

  260 Summit St Unit 2B, Windham, CT 06226
• 

  $281,000 Sold Mar 20, 2026

  5 Kathleen Dr, Willimantic, CT 06226

  • 2 Beds
  • 2 Baths
  • 1,080 Sq Ft
  • Built 1987

  Last Sold Summary

  • 2% Above List Price
  • $260/SF
  • 40 Days On Market

  Current Estimated Value $273,467

  Last Listing Agent Sue Esposito Home Selling Team

  5 Kathleen Dr, Willimantic, CT 06226
• 

  Est $112,999 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

  • 24% 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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