Windham County, CT Homes

• 

  Est $288,726

  Not Listed For Sale

  125 Main St, Sterling, CT 06377

  • 3 Beds
  • 1 Bath
  • 2,016 Sq Ft
  • Built 1900

  125 Main St, Sterling, CT 06377

  Last Sold Summary

  • 8 Days On Market
• 

  

  

  /35

  $369,000

  New Construction Pending

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

  4 Johns Cir Unit Lot 31, Sterling, CT 06377

  *To Be Built* Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built Raised Ranch offers the epitome of modern living. With Central Air and Hardwood flooring throughout, this home boasts City water and Sewer for added comfort. Picture yourself in the Gorgeous Granite Kitchen, complete with a view of the valley while you do dishes! Enjoy the ease of a

  Patrick Farrell Compass Connecticut, LLC

  4 Johns Cir Unit Lot 31, Sterling, CT 06377
• 

  $50,000

  Sold Sep 26, 2025

  121 Highland View Dr, Windham, CT 06266

  • Land
  • 40,075 Sq Ft
  • $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
• 

  Est $480,361

  Not Listed For Sale

  33 Railroad Ave, Sterling, CT 06377

  • 3 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 2004

  33 Railroad Ave, Sterling, CT 06377

  Last Sold Summary

  • 1 Day On Market
• 

  

  

  /13

  $299,900

  Pending

  • 1 Bed
  • 1 Bath
  • 832 Sq Ft

  34 Prince St, Danielson, CT 06239

  Welcome to this charming bungalow-style home located in the heart of Danielson! This well-maintained 3-bedroom, 1-bath single-family residence offers approximately 1,165 square feet of comfortable living space, perfect for first-time buyers or those looking to downsize. Situated on a generous 0.42-acre level lot, the property provides ample outdoor space for entertaining and gardening. Solar

  Claritza Fong Torres Coldwell Banker Realty

  34 Prince St, Danielson, CT 06239
• 

  $135,000

  Sold Aug 18, 2025

  256 Pine Hill Rd, Sterling, CT 06377

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft
  • Built 1955

  Last Sold Summary

  • 4% Above List Price
  • $188/SF
  • 5 Days On Market

  Current Estimated Value $144,424

  Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

  256 Pine Hill Rd, Sterling, CT 06377
• 

  Est $499,679

  Not Listed For Sale

  629 Margaret Henry Rd, Sterling, CT 06377

  • 3 Beds
  • 3 Baths
  • 2,156 Sq Ft
  • Built 2003

  629 Margaret Henry Rd, Sterling, CT 06377

  Last Sold Summary

  • 0 Days On Market
• 

  /2

  $200,000

  $50K PRICE DROP

  • Land
  • 34,848 Sq Ft
  • $250,000 per Acre

  35 S Main St, Brooklyn, CT 06234

  Bring your ideas for this commercial lot, centrally located in a high traffic area located right off route 6. Was previously approved for a 4800 sq.ft. retail/office building with two cutouts as an entrance/exit. Several options for commercial use such as retail shopping, office space, farmers market, restaurant, and more in the zoning regulations.

  Andrew Kausch Kazantzis Real Estate, LLC

  35 S Main St, Brooklyn, CT 06234
• 

  $725,000

  Sold Jan 23, 2026

  245 Brooklyn Rd, Canterbury, CT 06331

  • 4 Beds
  • 2.5 Baths
  • 3,285 Sq Ft
  • Built 1787

  Last Sold Summary

  • 8% Below List Price
  • $221/SF
  • 64 Days On Market

  Current Estimated Value $718,899

  Last Listing Agent Cary Marcoux RE/MAX Bell Park Realty

  245 Brooklyn Rd, Canterbury, CT 06331
• 

  Est $369,835

  Not Listed For Sale

  13 Sterling Ridge Ln, Sterling, CT 06377

  • 3 Beds
  • 2.5 Baths
  • 1,669 Sq Ft
  • Built 2007

  13 Sterling Ridge Ln, Sterling, CT 06377

  Last Sold Summary

  • 33 Days On Market
• 

  

  /8

  $28,900

  $2K PRICE INCREASE Pending

  • Land
  • 5,227 Sq Ft
  • $240,833 per Acre

  0 Pond St Unit 24037041, Plainfield, CT 06374

  APPROVED BUILDING LOT! Perfect lot to place a modular home or a conventional build. Level lot with public sewer in street. Minutes from I-395, and Rhode Island. Close to all amenities. Priced to SELL!!!

  Dale Bunn Riverview Realty, LLC

  0 Pond St Unit 24037041, Plainfield, CT 06374
• 

  $789,000

  Sold Aug 15, 2025

  43 Hiawatha Heights, Woodstock Valley, CT 06282

  • 2 Beds
  • 2 Baths
  • 1,918 Sq Ft
  • Built 1988

  Last Sold Summary

  • $411/SF
  • 42 Days On Market

  Current Estimated Value $795,011

  Last Listing Agent Jennie Kesselman Berkshire Hathaway NE Prop.

  43 Hiawatha Heights, Woodstock Valley, CT 06282
• 

  Est $522,104

  Not Listed For Sale

  562 Sterling Rd, Sterling, CT 06377

  • 3 Beds
  • 2 Baths
  • 2,096 Sq Ft
  • Built 2002

  562 Sterling Rd, Sterling, CT 06377

  Last Sold Summary

  • 6 Days On Market
• 

  

  /39

  $415,000

  $10K PRICE DROP Under Contract

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  13 Henry Dr, Moosup, CT 06354

  Welcome to 13 Henry Drive, a beautifully maintained ranch-style home designed for comfort, convenience, and easy living. Step inside to an inviting open floor plan highlighted by an upgraded kitchen featuring granite countertops and stainless-steel appliances. Perfect for both everyday living and entertaining. The spacious primary bedroom offers a private ensuite bath with a walk-in shower,

  Michael Houser, Jr. Capital Property Group, LLC

  13 Henry Dr, Moosup, CT 06354
• 

  $72,000

  Sold Apr 30, 2026

  16 Pond Way, North Windham, CT 06256

  • 2 Beds
  • 2 Baths
  • 1,218 Sq Ft
  • Built 1988

  Last Sold Summary

  • 6% Above List Price
  • $59/SF
  • 5 Days On Market

  Last Listing Agent Stephen Daly KW Legacy Partners

  16 Pond Way, North Windham, CT 06256
• 

  Est $476,022

  Not Listed For Sale

  637 Margaret Henry Rd, Sterling, CT 06377

  • 4 Beds
  • 2.5 Baths
  • 2,254 Sq Ft
  • Built 2005

  637 Margaret Henry Rd, Sterling, CT 06377

  Last Sold Summary

  • 1 Day On Market
• 

  

  /8

  $849,900

  Open Sat 12PM - 2PM Coming Soon

  • 5 Beds
  • 3 Baths
  • 2,246 Sq Ft

  651 Cook Hill Rd, Danielson, CT 06239

  Rare opportunity to own 32 breathtaking acres ideal for multi-generational living, farming, horses, recreation, a private compound/family homestead or even potential income-producing ventures. The beautifully updated circa-1920 farmhouse offers 5 bedrooms, 3 full baths, and a flexible office/bonus room with closet. Recent renovations blend modern convenience with timeless farmhouse charm and

  Joseph Bonneau eXp Realty

  651 Cook Hill Rd, Danielson, CT 06239
• 

  $620,000

  Sold May 11, 2026

  1350 Thompson Rd, Thompson, CT 06277

  • 3 Beds
  • 2.5 Baths
  • 2,610 Sq Ft
  • Built 2004

  Last Sold Summary

  • 3% Above List Price
  • $238/SF
  • 3 Days On Market

  Current Estimated Value $605,354

  Last Listing Agent Christine Johnson RE/MAX One

  1350 Thompson Rd, Thompson, CT 06277
• 

  Est $1,073,859

  Not Listed For Sale

  53 Brookstone Dr, Sterling, CT 06377

  • 5 Beds
  • 3.5 Baths
  • 5,462 Sq Ft
  • Built 2006

  53 Brookstone Dr, Sterling, CT 06377

  Last Sold Summary

  • 36 Days On Market
• 

  

  /40

  $339,000

  Pending

  • 4 Beds
  • 3.5 Baths
  • 3,085 Sq Ft

  278 N Bigelow Rd, Hampton, CT 06247

  Set on 13.75 acres of beautiful wooded land in Hampton, CT, this unique colonial single family with in-law property offers space, character, and endless potential. Featuring 4 bedrooms and 3.5 bathrooms, the home showcases warm wooden floors, a cozy wood stoves, multiple closets for abundant storage, and an unfinished basement for additional storage. Enjoy peaceful outdoor living with a charming

  Thomas Mele Social & Co Realty

  278 N Bigelow Rd, Hampton, CT 06247
• 

  $400,000

  Sold Oct 03, 2025

  16 Porter Plain Rd, Thompson, CT 06277

  • 3 Beds
  • 2 Baths
  • 1,960 Sq Ft
  • Built 1974

  Last Sold Summary

  • 5% Above List Price
  • $204/SF
  • 3 Days On Market

  Current Estimated Value $405,371

  Last Listing Agent Jared Meehan RE/MAX Bell Park Realty

  16 Porter Plain Rd, Thompson, CT 06277
• 

  Est $315,927

  Not Listed For Sale

  61 Laiho Rd, Sterling, CT 06377

  • 4 Beds
  • 1.5 Baths
  • 1,566 Sq Ft
  • Built 1933

  61 Laiho Rd, Sterling, CT 06377

  Last Sold Summary

  • 41 Days On Market
• 

  

  /30

  $329,900

  $5K PRICE DROP

  • 2 Beds
  • 1.5 Baths
  • 1,800 Sq Ft

  74 Perry St Unit 183, Putnam, CT 06260

  Welcome to easy, low-maintenance condo living in the heart of Putnam! This well-appointed 2-bedroom, 1.5-bath home offers a bright and inviting main level featuring a sun-filled living room with beautiful hardwood floors and direct access to a private wood deck-perfect for seamless indoor/outdoor living. The kitchen is designed for both function and comfort, complete with a dining area, pantry

  Genevieve Botelho Lamacchia Realty

  74 Perry St Unit 183, Putnam, CT 06260
• 

  $355,000

  Sold Jan 14, 2026

  5 Chappell St, Chaplin, CT 06235

  • 3 Beds
  • 2.5 Baths
  • 1,748 Sq Ft
  • Built 1954

  Last Sold Summary

  • 3% Above List Price
  • $203/SF
  • 53 Days On Market

  Current Estimated Value $343,710

  Last Listing Agent Gregory Hanner Garden Realty

  5 Chappell St, Chaplin, CT 06235
• 

  Est $641,943

  Not Listed For Sale

  242 Harris Rd, Sterling, CT 06377

  • 4 Beds
  • 3.5 Baths
  • 4,184 Sq Ft
  • Built 1977

  242 Harris Rd, Sterling, CT 06377

  Last Sold Summary

  • 322 Days On Market
• 

  

  /37

  $350,000

  Pending

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  221 Eastford Rd, Eastford, CT 06242

  ** Highest & Best Deadline for Monday 5/11 at 10 AM** .Step into this thoughtfully crafted post-and-beam home set on over 3 peaceful acres, with the Still River gently running through the property. Built in 1985, it offers warmth, character, and a serene setting with frequent wildlife sightings. The spacious eat-in kitchen features a walk-in pantry, custom island, and sliding barn door, along

  Skyla Gagnon RE/MAX Bell Park Realty

  221 Eastford Rd, Eastford, CT 06242
• 

  $395,000

  Sold Nov 03, 2025

  50 Crooked Trail, Woodstock, CT 06281

  • 3 Beds
  • 3 Baths
  • 2,339 Sq Ft
  • Built 1993

  Last Sold Summary

  • 6% Below List Price
  • $169/SF
  • 16 Days On Market

  Current Estimated Value $427,257

  Last Listing Agent Lynn Converse RE/MAX Bell Park Realty

  50 Crooked Trail, Woodstock, CT 06281
• 

  Est $474,032

  Not Listed For Sale

  297 Sabin St Unit 34, Putnam, CT 06260

  • 4 Beds
  • 3 Baths
  • 3,171 Sq Ft
  • Built 2018

  297 Sabin St Unit 34, Putnam, CT 06260

  Last Sold Summary

  • 4 Days On Market
• 

  

  /36

  $415,000

  • 4 Beds
  • 2 Baths
  • 2,062 Sq Ft

  177 Slater Hill Rd, Dayville, CT 06241

  Circa 1870 Colonial farmhouse blending vintage character with thoughtful updates, offering 2,062 sqft, 4 bedrooms & 2 full baths on 3.53 picturesque acres of rolling farmland. Inside, rustic charm meets everyday comfort with vinyl & wood plank flooring, an eat-in kitchen & formal dining room. An humongous 3-season room w/electric fireplace creates the perfect gathering space, while replacement

  Sharon Pelletier Hope Real Estate Group, Inc.

  177 Slater Hill Rd, Dayville, CT 06241
• 

  $399,000

  Sold Feb 20, 2026

  10 School Street Extension, Plainfield, CT 06374

  • 3 Beds
  • 2.5 Baths
  • 1,824 Sq Ft
  • Built 2025

  Last Sold Summary

  • 13% Below List Price
  • $219/SF
  • 63 Days On Market

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

  10 School Street Extension, Plainfield, CT 06374
• 

  Est $415,484

  Not Listed For Sale

  297 Sabin St Unit 32, Putnam, CT 06260

  • 2 Beds
  • 2 Baths
  • 1,527 Sq Ft
  • Built 2017

  297 Sabin St Unit 32, Putnam, CT 06260

  Last Sold Summary

  • 2 Days On Market
• 

  

  /36

  $449,900

  • 5 Beds
  • 2.5 Baths
  • 2,887 Sq Ft

  13 Bates Rd, Chaplin, CT 06235

  Spacious farmhouse living at its best! This charming 5-bedroom, 2 full bath, and 1 half bath home sits on an expansive 11 acres, offering endless possibilities for privacy, recreation, or hobby farming. Inside, you'll find hardwood flooring throughout and two cozy fireplaces that add warmth and character. The versatile layout includes two additional family rooms that could easily serve as extra

  Kristen Merrill Countryside Realty

  13 Bates Rd, Chaplin, CT 06235
• 

  $80,000

  Sold Aug 29, 2025

  0 Lustig Rd, Ashford, CT 06278

  • Land
  • 13.18 Acres
  • $6,070 per Acre

  Last Sold Summary

  • 6% Below List Price
  • 10 Days On Market

  Last Listing Agent Amy Rio Better Homes and Gardens Real Estate Executive Real Estate

  0 Lustig Rd, Ashford, CT 06278
• 

  Est $429,395

  Not Listed For Sale

  297 Sabin St Unit 30, Putnam, CT 06260

  • 2 Beds
  • 2 Baths
  • 1,811 Sq Ft
  • Built 2018

  297 Sabin St Unit 30, Putnam, CT 06260

  Last Sold Summary

  • 4 Days On Market
• 

  

  /36

  $349,900

  $10K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 1,643 Sq Ft

  45 Breaults Landing Rd, Thompson, CT 06277

  Enjoy the serenity of lake living with water views and sunset skies. Elevated home has 1,643 sqft, 2-bed, 2-bath home overlooking Quaddick Lake with panoramic water views and deeded water privileges. The primary suite features vaulted ceilings, a skylight, and beautiful lake views, creating a bright, airy space. A flexible loft area adds versatility for a variety of uses. The open concept main

  Christine Johnson RE/MAX One

  45 Breaults Landing Rd, Thompson, CT 06277
• 

  $402,000

  Sold Apr 24, 2026

  1370 Plainfield Pike, Sterling, CT 06377

  • 5 Beds
  • 2 Baths
  • 1,498 Sq Ft
  • Built 1986

  Last Sold Summary

  • 1% Above List Price
  • $268/SF
  • 14 Days On Market

  Current Estimated Value $396,724

  Last Listing Agent Derek Greene Derek Greene

  1370 Plainfield Pike, Sterling, CT 06377
• 

  Est $483,516

  Not Listed For Sale

  78 Smith Rd, Moosup, CT 06354

  • 3 Beds
  • 1 Bath
  • 2,493 Sq Ft
  • Built 1962

  78 Smith Rd, Moosup, CT 06354

  Last Sold Summary

  • 8 Days On Market
• 

  

  /12

  $215,000

  Pending

  • 3 Beds
  • 1.5 Baths
  • 1,446 Sq Ft

  85 Wauregan Rd, Danielson, CT 06239

  Check out this antique Cape just minutes from downtown Danielson! This home has 3 bedrooms located on the upper floor, with plenty of flexible space. The primary floor has many wonderful features including a large kitchen that opens up to the back deck, a full bath, and a dining space. Enjoy overlooking the yard from the enclosed deck! Plumbing did not hold positive air pressure at the time of

  Ryan King Aspen Realty Group

  85 Wauregan Rd, Danielson, CT 06239
• 

  $349,900

  Sold Apr 03, 2026

  25 Snake Meadow Rd, Moosup, CT 06354

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Built 1982

  Last Sold Summary

  • $350/SF
  • 34 Days On Market

  Current Estimated Value $346,141

  Last Listing Agent Rachael Gifford The Neighborhood Realty Group

  25 Snake Meadow Rd, Moosup, CT 06354
• 

  Est $369,521

  Not Listed For Sale

  78 Cranska Rd, Moosup, CT 06354

  • 3 Beds
  • 2 Baths
  • 2,582 Sq Ft
  • Built 1963

  78 Cranska Rd, Moosup, CT 06354

  Last Sold Summary

  • 42 Days On Market

Showing Results 281 - 320, Page 8 of 18