Windham County, CT Homes

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  /38

  $789,000

  • 4 Beds
  • 2.5 Baths
  • 2,900 Sq Ft

  287 S Bear Hill Rd, Chaplin, CT 06235

  Set on 3.39 picturesque acres, this beautifully renovated property offers the perfect blend of luxury, function, and country charm-ideal for a mini farm, homestead, or private retreat. The heated and insulated 36x48 Morton barn features front and rear sliding barn doors, 2 horse stalls with potential for 6, 5 doggy doors, water, electric, skylights, and year-round water access-perfect for horses,

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 374-6602

  287 S Bear Hill Rd, Chaplin, CT 06235
• 

  

  

  /31

  $3,100 Per Month

  • 4 Beds
  • 2 Baths
  • 1,701 Sq Ft
  • House for Rent

  223 High St, Willimantic, CT 06226

  Cozy, well maintained 4 bedroom 2 bath home situated in hill section of Willimantic. This house offers central air, ample storage as well as a washer and dryer, central air, oil heat and has room for 5 tenants. This property sits across the street from ECSU, is on the bus route to UConn and is just 8 miles from campus with convenient access to grocery stores, gyms and night life. Close to

  

  Rick Nassiff

  KW Legacy Partners

  (860) 370-2871

  223 High St, Willimantic, CT 06226
• 

  $660,000

  Sold Apr 24, 2026

  140 N Frontage Rd, Danielson, CT 06239

  • 4 Beds
  • 3.5 Baths
  • 2,699 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Above List Price
  • $245/SF
  • 22 Days On Market

  Current Estimated Value $648,092

  Last Listing Agent Valerie MacNeil Kazantzis Real Estate, LLC

  140 N Frontage Rd, Danielson, CT 06239
• 

  Est $336,583

  Not Listed For Sale

  174 N Sterling Rd, Moosup, CT 06354

  • 2 Beds
  • 1 Bath
  • 1,440 Sq Ft
  • Built 1958

  174 N Sterling Rd, Moosup, CT 06354

  Last Sold Summary

  • 0 Days On Market
• 

  

  

  /40

  $475,000

  Under Contract

  • 4 Beds
  • 3.5 Baths
  • 3,639 Sq Ft

  3 North Rd, Windham, CT 06280

  It's BACK!! This is your moment. There's something about the Windham Center green that just feels like home. Whether it's the people, the library, or the history, the moment you arrive, you know that it's special. And the standout on the Green? 3 North Road. Built in 1885 and loved every year since, it is the kind of place that has passerbys slowing down to take it all in. Step inside and you

  

  Stephen Daly

  KW Legacy Partners

  (860) 943-5201

  3 North Rd, Windham, CT 06280
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  /14

  Starting at $1,825 Plus Fees

  • 3 Beds

  80 Bicknell Rd, Ashford, CT 06278

  Can you hear the "birds chirping and woodpeckers pecking" in your current home? Woodlawn Apartments consists of 12 charming buildings on 11 beautiful acres. Our residents enjoy the peace and quiet of nature in a convenient location, along with a caring management and maintenance staff. Only five miles from UConn. Also, call us about our nearby Wood Edge Apartments in Mansfield Center 4 miles from

  Woodlawn Apartments

  (959) 210-1600

  80 Bicknell Rd, Ashford, CT 06278
• 

  $22,000

  Sold Aug 07, 2025

  40 S Prospect St, Putnam, CT 06260

  • Land
  • 1.05 Acres
  • $20,952 per Acre

  Last Sold Summary

  • 72 Days On Market

  Current Estimated Value $187,403

  Last Listing Agent Derek Greene Derek Greene

  40 S Prospect St, Putnam, CT 06260
• 

  Est $400,171

  Not Listed For Sale

  15 Marion Ln, Canterbury, CT 06331

  • 3 Beds
  • 1.5 Baths
  • 1,622 Sq Ft
  • Built 1977

  15 Marion Ln, Canterbury, CT 06331

  Last Sold Summary

  • 18 Days On Market
• 

  

  /39

  $589,900

  • 3 Beds
  • 2.5 Baths
  • 3,096 Sq Ft

  2 Legacy Dr, Sterling, CT 06354

  Beautifully maintained one-owner Colonial built in 2020 and set on a spacious 1.36-acre lot in Sterling's desirable Legacy subdivision. Offering over 2,000 sq ft above grade plus a fully finished lower level, this home combines comfort, functionality, and energy efficiency with fully owned solar panels and underground utilities. The main level features hardwood flooring, an open-concept layout,

  

  Gia Parmentier

  J. Christopher Real Estate Group

  (860) 419-0696

  2 Legacy Dr, Sterling, CT 06354
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  /41

  Starting at $1,085

  Total Monthly Price

  • 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

  Colonial Townhouse Apartments

  (860) 809-5254

  

  29 Foster Dr, Willimantic, CT 06226
• 

  $525,000

  Sold Jul 08, 2025

  124 Elmdale Rd, Canterbury, CT 06331

  • 4 Beds
  • 4 Baths
  • 2,712 Sq Ft
  • Built 1976

  Last Sold Summary

  • 12% Below List Price
  • $194/SF
  • 94 Days On Market

  Current Estimated Value $536,053

  Last Listing Agent Christine Johnson RE/MAX One

  124 Elmdale Rd, Canterbury, CT 06331
• 

  Est $683,462

  Not Listed For Sale

  234 Route 197, Woodstock, CT 06281

  • 2 Beds
  • 2.5 Baths
  • 2,970 Sq Ft
  • Built 1990

  234 Route 197, Woodstock, CT 06281

  Last Sold Summary

  • 33 Days On Market
• 

  

  /39

  $475,000

  Open Sat 11AM - 1:30PM Coming Soon

  • 9 Beds
  • 6 Baths
  • 4,824 Sq Ft

  37 Manners Ave, Willimantic, CT 06226

  What if your next investment came with an indoor pool that you could make a splash in all year round? 37 Manners Ave is not your average multifamily. This custom-built 3-family sits on a spacious lot in Willimantic with two units that each include attached in-law suites; a full studio unit and a finished basement suite with an extra bedroom, giving owners over 4,800 square feet to work with. Two

  

  Stephen Daly

  KW Legacy Partners

  (860) 846-3628

  37 Manners Ave, Willimantic, CT 06226
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  /9

  Starting at $1,695

  Total Monthly Price

  • 2 Beds

  95 Varga Rd, Ashford, CT 06278

  Conveniently located, but full of quiet country charm, Ashford Hills offers one, two, and three-bedroom apartments, perfect to match any lifestyle! Located just six miles from the University of Connecticut right off route 44.Ashford Hills is an apartment community located in Windham County and the 06278 ZIP Code. This area is served by the Mansfield attendance zone.

  Ashford Hills

  (860) 541-5910

  95 Varga Rd, Ashford, CT 06278
• 

  $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 $286,135

  Not Listed For Sale

  32 Crystal Rd, North Windham, CT 06256

  • 2 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1991

  32 Crystal Rd, North Windham, CT 06256

  Last Sold Summary

  • 24 Days On Market
• 

  

  /40

  $739,900

  Under Contract

  • 2 Beds
  • 2.5 Baths
  • 2,447 Sq Ft

  349 S Bigelow Rd, Hampton, CT 06247

  Beautiful Post and Beam design home, Tranquil setting nestled on 25+ acres with pond,babbling brook, and hiking trails nature at it best. This home has a unique design spoiling you with Private Hot tub, sauna, and solarium leading to outdoor patio with fireplace overlooking the pond side. Dramatic open layout with Swedish style stucco fireplace. This design offers the ability to have 2 or 3

  

  Amy Rio

  Better Homes and Gardens Real Estate Executive Real Estate

  (860) 831-4269

  349 S Bigelow Rd, Hampton, CT 06247
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  /40

  Starting at $1,550 Plus Fees

  • 2 Beds

  52 Perry Hill Rd, Ashford, CT 06278

  Perry Hill Apartments offers two bedroom townhouse apartment homes for rent in Ashford, CT. Our pet friendly community features amenities such as on-site laundry, dishwashers and private patios. We are located close to University of Connecticut and major highways.

  Perry Hill Apartments

  (860) 406-5079

  52 Perry Hill Rd, Ashford, CT 06278
• 

  $380,000

  Sold May 15, 2026

  3 Oriole Dr, Danielson, CT 06239

  • 2 Beds
  • 2 Baths
  • 1,436 Sq Ft
  • Built 2006

  Last Sold Summary

  • 9% Above List Price
  • $265/SF
  • 2 Days On Market

  Current Estimated Value $351,581

  Last Listing Agent Jennifer Mahr RE/MAX Bell Park Realty

  3 Oriole Dr, Danielson, CT 06239
• 

  Est $333,408

  Not Listed For Sale

  63 Robbins Rd, Thompson, CT 06277

  • 2 Beds
  • 1.5 Baths
  • 1,543 Sq Ft
  • Built 1950

  63 Robbins Rd, Thompson, CT 06277

  Last Sold Summary

  • 1 Day On Market
• 

  

  /35

  $299,000

  Under Contract

  • 3 Beds
  • 2 Baths
  • 1,056 Sq Ft

  63 Whittemore St, Willimantic, CT 06226

  OFFER DEADLINE: The seller is asking for all offers to be in by Tuesday, 04/14, at 6 pm. THANK YOU! Welcome to this well-maintained 3-bedroom, 2-bath ranch offering comfort, convenience, and modern updates throughout. Ideally located near Route 6, this home provides easy access to shopping, dining, and is just a short drive to Eastern Connecticut State University and UCONN. Inside, you'll find

  

  Barbara Royea

  Carl Guild & Associates

  (860) 845-1170

  63 Whittemore St, Willimantic, CT 06226
• 

  

  /40

  Starting at $1,500 Plus Fees

  • 2 Beds

  149 Ashford Center Rd, Ashford, CT 06278

  Stunning remodeled units available now! Call/text manager for details! Don't miss out on this opportunity!

  Birch Hill Apartments

  (860) 854-3752

  149 Ashford Center Rd, Ashford, CT 06278
• 

  $225,000

  Sold Oct 30, 2025

  214 Park Rd, Putnam, CT 06260

  • Land
  • 5.41 Acres
  • $41,590 per Acre

  Last Sold Summary

  • 36% Below List Price
  • 790 Days On Market

  Current Estimated Value $290,043

  Last Listing Agent Michael Collins Berkshire Hathaway NE Prop.

  214 Park Rd, Putnam, CT 06260
• 

  Est $521,333

  Not Listed For Sale

  213 Church St, Brooklyn, CT 06234

  • 4 Beds
  • 2.5 Baths
  • 2,698 Sq Ft
  • Built 1999

  213 Church St, Brooklyn, CT 06234

  Last Sold Summary

  • 25 Days On Market
• 

  

  /40

  $639,900

  Under Contract

  • 3 Beds
  • 2 Baths
  • 2,237 Sq Ft

  210 Hill Rd, Thompson, CT 06277

  Welcome to this beautifully maintained 3-bedroom, 2-bath Cape set on 6.69 private acres, with professionally landscaped grounds surrounding the home. Built in 2013, this 2,237 sq ft home offers an open-concept layout, featuring a spacious kitchen with granite countertops, center island, and dining area, perfect for everyday living and entertaining. Hardwood flooring adds warmth and character

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 492-6967

  210 Hill Rd, Thompson, CT 06277
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  /7

  Starting at $1,295 Plus Fees

  • Studio - 2 Beds

  804 Main St, Willimantic, CT 06226

  New Construction Move in Ready this August. Minutes from college and shops! Fitness center/Laundry and Golf simulator on site. Lots of room for storage and many more amenities. Great for college student/working professional and families. Contact us for a tour!

  Residences on Main

  (959) 210-5321

  804 Main St, Willimantic, CT 06226
• 

  $295,000

  Sold Sep 02, 2025

  118 Ashford Rd Unit 6, Eastford, CT 06242

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft
  • Built 2015

  Last Sold Summary

  • 4% Below List Price
  • $242/SF
  • 9 Days On Market

  Current Estimated Value $299,021

  Last Listing Agent Brittany Kimlingen First Choice Realty

  118 Ashford Rd Unit 6, Eastford, CT 06242
• 

  Est $368,940

  Not Listed For Sale

  18A Proulx St, Brooklyn, CT 06234

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft
  • Built 2007

  18A Proulx St, Brooklyn, CT 06234

  Last Sold Summary

  • 2 Days On Market
• 

  

  /23

  $330,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,302 Sq Ft

  654 N Main St, Danielson, CT 06239

  Welcome to this beautifully refreshed New England home. Offering a blend of classic charm and modern updates, this property provides a warm and inviting setting both inside and out. Step inside to a bright, open interior featuring updated flooring, fresh finishes, and abundant natural light. The main living spaces flow seamlessly, including a comfortable living room and a dedicated dining area

  

  Ben Emerick

  Flagship Real Estate Advisors

  (860) 362-2982

  654 N Main St, Danielson, CT 06239
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  /13

  Starting at $1,050 Plus Fees

  • 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 On Main

  (959) 210-6726

  560 Main 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 $293,812

  Last Listing Agent Valerie Yankus Property Shoppe, LLC

  Unlisted Address
• 

  Est $274,210

  Not Listed For Sale

  69 Westford Dr, Ashford, CT 06278

  • 2 Beds
  • 1 Bath
  • 830 Sq Ft
  • Built 1950

  69 Westford Dr, Ashford, CT 06278

  Last Sold Summary

  • 85 Days On Market
• 

  

  /40

  $779,900

  $70K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,316 Sq Ft

  483 North Rd, Ashford, CT 06278

  Exceptional Currier and Ives type setting in peaceful Ashford CT. Set on 25 acres that preliminary work was done showing 4 lots and leaving the house with over 5 acres. This property has a Barn with three oversized stalls and pastures; property absolutely designed for horses. This home has been tenderly updated to maintain all that historic feeling of this 225-year-old home while having all of

  

  Dan Keune

  Campbell-Keune Realty Inc

  (860) 813-3662

  483 North Rd, Ashford, CT 06278
• 

  

  /5

  Starting at $1,290 Plus Fees

  • 1 - 3 Beds

  480 Main St, Willimantic, CT 06226

  Artspace Windham

  (959) 210-1927

  480 Main St, Willimantic, CT 06226
• 

  $359,000

  Sold Sep 23, 2025

  12 John St, Danielson, CT 06239

  • 3 Beds
  • 1.5 Baths
  • 1,248 Sq Ft
  • Built 1951

  Last Sold Summary

  • $288/SF
  • 107 Days On Market

  Current Estimated Value $355,074

  Last Listing Agent Nicholas Tomanelli Coldwell Banker Realty

  12 John St, Danielson, CT 06239
• 

  Est $329,086

  Not Listed For Sale

  573 Putnam Rd, Plainfield, CT 06374

  • 2 Beds
  • 1.5 Baths
  • 1,469 Sq Ft
  • Built 1952

  573 Putnam Rd, Plainfield, CT 06374

  Last Sold Summary

  • 2 Days On Market
• 

  

  /40

  $512,500

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,480 Sq Ft

  121 Kozey Rd, Eastford, CT 06242

  Tucked away on a private 3.9 acre wooded setting, this beautiful Cape-style home offers the perfect combination of comfort, character, and future expansion potential. The open-concept main living area is filled with natural light and showcases soaring cathedral ceilings, dramatic triangular windows, hardwood floors, and a stunning stone fireplace with wood stove insert. The spacious kitchen

  

  Carol Ryniewicz

  CR Premier Properties

  (860) 979-6411

  121 Kozey Rd, Eastford, CT 06242
• 

  

  /35

  Starting at $1,855

  Total Monthly Price

  • 2 Beds

  140 Plains Rd, Windham, CT 06280

  Nestled in a wooded corner of Windham, CT, the two-bedroom townhome apartments at Wyndham Park offer an elevated living experience in a scenic neighborhood. Our community’s mature trees and lush landscapes provide the backdrop for a life you’ll truly love. From the moment you open your front door, an expansive layout, complete with modern conveniences, make you feel right at home. Contemporary

  Wyndham Park

  (860) 809-4918

  140 Plains Rd, Windham, CT 06280
• 

  $285,000

  Sold Aug 01, 2025

  601 Whetstone Mills Unit 601, Dayville, CT 06241

  • 2 Beds
  • 1.5 Baths
  • 1,240 Sq Ft
  • Built 1989

  Last Sold Summary

  • 5% Below List Price
  • $230/SF
  • 36 Days On Market

  Current Estimated Value $283,272

  Last Listing Agent Jarrod Lewis J. Christopher Real Estate Group

  601 Whetstone Mills Unit 601, Dayville, CT 06241
• 

  Not Listed For Sale

  24 Sterling Ridge Ln Unit Lot 23, Sterling, CT 06377

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft
  • Built 2024

  24 Sterling Ridge Ln Unit Lot 23, Sterling, CT 06377

  Last Sold Summary

  • 63 Days On Market

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