Windham County CT Homes for Sale

• 

  

  

  /22

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,690 Sq Ft

  8 Plainview Dr, Plainfield, CT 06374

  Welcome to 8 Plainview Drive, a beautifully updated 4-bedroom, 2-bath Cape located on a quiet cul-de-sac in Plainfield. Situated on 0.81 acres, this home offers plenty of space while still being close to everything you need. Over the last few years, the home has seen extensive updates, including a new roof, vinyl siding, repaved driveway, farmer's porch, and front bedroom dormers, all completed

  Kelsie Griffin Wolfburg Kazantzis Real Estate, LLC

  8 Plainview Dr, Plainfield, CT 06374
• 

  

  

  /17

  $289,500

  $10K PRICE DROP

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

  10 Potter St, Willimantic, CT 06226

  Unique property! 1920s Dutch Colonial with many new upgrades. Small private lot that is easy to maintain. Front and rear porches. Adjacent to Amer ican Legion Field and close to Jillson Square. Come take a look! Kitchen cabinet doors are currently off, and are being given a fresh coat of white paint. They will be installed prior to closing.

  Ryan King Aspen Realty Group

  10 Potter St, Willimantic, CT 06226
• 

  

  /2

  $745,000

  New Construction $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,020 Sq Ft

  106 Church St, Brooklyn, CT 06234

  Approved building lot on desirable street, property is on a shared driveway. TO BE BUILT: A 2,020 sqft., 3 bedroom, 2.5 bath colonial style home sits on a beautiful 2.6 acre lot. The kitchen features a tile backsplash, oversized island, stainless steel range hood, pantry cabinet, and quartz countertops. The living room flows from the kitchen creating an open feel. Hardwood flooring throughout the

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  106 Church St, Brooklyn, CT 06234
• 

  

  

  /23

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  222 Tower Hill Rd, Chaplin, CT 06235

  Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featuring approximately 1,600 square feet, the home showcases soaring vaulted ceilings, stunning exposed beams, and an inviting open-concept kitchen, dining, and living area filled with natural light. The finished lower level offers a

  Lisa Therecka Therecka & Associates LLC

  222 Tower Hill Rd, Chaplin, CT 06235
• 

  

  

  /39

  $475,000

  • 2 Beds
  • 1 Bath
  • 1,176 Sq Ft

  420 Brandy Hill Rd, Thompson, CT 06277

  Wake up to beautiful lake views and enjoy year-round waterfront living in this charming single-family home on scenic Quaddick Lake.Whether you love fishing, swimming, or boating, Quaddick Lake offers it all, with access for all types of recreational boats.This inviting home features nearly 1,200 sqft of comfortable living space,including 2 bedrooms and 1 full bath.The spacious fireplaced living

  Rachael Johnston Johnston & Associates Real Estate, LLC

  420 Brandy Hill Rd, Thompson, CT 06277
• 

  

  /35

  $229,900

  • Land
  • 34.8 Acres
  • $6,606 per Acre

  305 Tripp Hollow Rd, Brooklyn, CT 06234

  Amazing land opportunity offers nature's bounty on 35 subdividable acres consisting of multiple parcels. The premises includes a picturesque pond, has approximately 900 feet of road frontage and can be divided into multiple lots immediately without subdivision approval/process. Plenty of nature to enjoy, steel girders mounted on concrete abutments are the remains of the bridge that crosses the

  Dennis Duga Northeast Realty

  305 Tripp Hollow Rd, Brooklyn, CT 06234
• 

  

  /12

  $325,000

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  50 Pine Hill Rd, Sterling, CT 06377

  Attention investors, contractors, and handy buyers! This 4-bedroom, 2 full bathroom cape presents an outstanding opportunity to build equity and transform a property with incredible potential. While the home is in need of a full renovation, several major features are already in place, including a brand-new roof and solar system to help offset future energy costs. Inside, you'll find a spacious

  Amy Therrien The Neighborhood Realty Group

  50 Pine Hill Rd, Sterling, CT 06377
• 

  

  /40

  $369,900

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  97 Kapitulik Rd, North Grosvenordale, CT 06255

  The inside of this home is adorable. The outside is an oasis of relaxation with absolute privacy. This is a well loved home that is in move-in condition. Cozy living room, updated kitchen, 3 Bedrooms on main floor. The lower level has a comfy family room, laundry and plenty of storage. The one car garage doubles as a workshop. So many great features, you won't be disappointed.

  Mae Lyons Stonehouse Real Estate Co., LLC

  97 Kapitulik Rd, North Grosvenordale, CT 06255
• 

  

  /11

  $699,900

  $30K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,696 Sq Ft

  115 Groveland Ave Unit 7 & 8, Putnam, CT 06260

  Development Opportunity! Fully approved condominium project on a private lot with views, offering a turnkey development package including land, two existing townhouses with garages, and approvals for eight additional units to be built, with fully engineered plans available by request. Town approvals are in place, underground utilities are on site, and initial infrastructure has been completed.

  Jennie Kesselman Berkshire Hathaway NE Prop.

  115 Groveland Ave Unit 7 & 8, Putnam, CT 06260
• 

  

  /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
• 

  

  /16

  $474,900

  • 8 Beds
  • 2 Baths
  • 2,450 Sq Ft

  232 Ballouville Rd, Dayville, CT 06241

  Side by side two family home, perfect for owner-occupants or investors. Each unit offers a functional layout. One unit features all 4 bedrooms on the second floor with the convenience of a first floor laundry room, while the second unit offers a desirable first-floor bedroom and a similar layout. Recent improvements include new flooring on the second floor bedrooms in unit on the left. Situated

  Joanne Lukaskiewicz Wheaton Berkshire Hathaway NE Prop.

  232 Ballouville Rd, Dayville, CT 06241
• 

  

  /39

  $350,000

  $40K PRICE DROP

  • 6 Beds
  • 2 Baths
  • 2,678 Sq Ft

  36 Church St, Dayville, CT 06241

  Well-maintained two-family home located in a convenient area of Killingly, Connecticut. Each unit offers three spacious bedrooms and one full bathroom, with plenty of windows throughout allowing for abundant natural light. Both units include in-unit washer and dryer for added convenience. Unit 36A is equipped with a Navien propane system and mini-split heating and cooling, while Unit 36B features

  Kyle Seyboth Century 21 Limitless

  36 Church St, Dayville, CT 06241
• 

  

  /25

  $299,900

  • Land
  • 1.07 Acres
  • $280,280 per Acre

  71 Deerfield Dr, Sterling, CT 06377

  Discover the potential of this 1.07 acre lot. The property currently features a barn structure, but the true value lies in the land itself, being located on a private - no outlet road! With ample space to develop to dream property. Explore the possibilities this well-situated property has to offer. Trailer on property does not convey.

  Kristopher Tramont Real Broker CT, LLC

  71 Deerfield Dr, Sterling, CT 06377
• 

  

  /30

  $859,900

  $90K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,437 Sq Ft

  9 Becola Rd, Thompson, CT 06277

  Rare opportunity to own 100 feet of beautiful pond frontage in Thompson, CT! From the moment you arrive, you'll fall in love with the peaceful setting, breathtaking water views, and the care that has gone into maintaining this home. Whether you're enjoying your morning coffee overlooking the lake, relaxing in the hot tub, or unwinding after a long day, this property offers a true sense of

  Chelsea Greene CR Premier Properties

  9 Becola Rd, Thompson, CT 06277
• 

  

  /6

  $319,000

  • Land
  • 2.07 Acres
  • $154,106 per Acre

  366 Hartford Turnpike, Hampton, CT 06247

  Strategic Commercial Development Site | 2.07 Acres on Route 6 High-Visibility Location in Hampton, CT The Opportunity: Maximize your business's footprint on one of Eastern Connecticut's most vital transit corridors. This 2.07-acre commercial parcel is situated directly on Route 6, the primary link between Hartford and Providence. With a powerhouse traffic count of approximately 18,000 Vehicles

  Scott Pempek Berkshire Hathaway NE Prop.

  366 Hartford Turnpike, Hampton, CT 06247
• 

  /2

  $125,000

  • Land
  • 1.06 Acres
  • $117,925 per Acre

  86 Ference Rd, Ashford, CT 06278

  Here is a rare opportunity to buy a FULLY Approved 1.06 Acre Building lot in the beautiful new Subdivision of Ashford Meadow Estates, Known as Lot #4 in Ashford's Newest 6 lot subdivision featuring picturesque land in Eastern CT's quiet corner. Build your own or have Titan Construction build a custom home for you. Custom homes currently offered include ranch and colonial farmhouse style and start

  Mark Massaro Coldwell Banker Realty

  86 Ference Rd, Ashford, CT 06278
• 

  

  /30

  $500,000

  • 3 Beds
  • 2.5 Baths
  • 2,080 Sq Ft

  17 Tripp Hollow Rd, Brooklyn, CT 06234

  Welcome to 17 Tripp Hollow Road in Brooklyn, Connecticut, where the charm of country living meets the comfort of a thoughtfully maintained home. Tucked away on a quiet scenic road, this Colonial, built in 2005, offers 2,100 square feet of living space with three bedrooms, two full bathrooms, one half bath, and an attached two-car garage. Step inside to discover a spacious, functional layout

  Adam Gumula Kazantzis Real Estate, LLC

  17 Tripp Hollow Rd, Brooklyn, CT 06234
• 

  

  /5

  $175,000

  • Land
  • 7.33 Acres
  • $23,874 per Acre

  308 Orchard Hill Rd, Pomfret Center, CT 06259

  7.33 acres zoned commerce, located on orchard hill road. [route 169] 338 feet of frontage, abutting other commercial businesses, level to the road. property is located across from big boy toys in pomfret. No improvements have been done - all inspections / zoning concerns will be responsibility of purchaser

  Jim Nispel Coldwell Banker Realty

  308 Orchard Hill Rd, Pomfret Center, CT 06259
• 

  

  /25

  $449,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,450 Sq Ft

  25 Woodward Rd, Brooklyn, CT 06234

  Offered for the very first time, this home has been cherished by its original owners since it was built. The completely renovated main level features an open-concept floor plan. The stunning kitchen with a dining area is tastefully designed. With plenty of cabinet space, granite countertops, tiled back splash and an oversized granite center island, it's the perfect gathering spot. The chef in

  Lyn Lacharite Brunet and Company Real Estate

  25 Woodward Rd, Brooklyn, CT 06234
• 

  

  /40

  $624,000

  $56K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,780 Sq Ft

  1 Maple Ln, Thompson, CT 06277

  Beautifully maintained and built to last, this spacious 4 bedroom, 3.5 bath home offers comfort, quality, and exceptional living space in a prime location near prestigious Thompson Hill. Situated on a manicured corner lot, the home features newer vinyl siding with a lifetime warranty, and 50-year shingles for peace of mind. Designed for easy living and entertaining, enjoy the oversized composite

  Tracie Gagnon Berkshire Hathaway NE Prop.

  1 Maple Ln, Thompson, CT 06277
• 

  

  /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
• 

  

  /28

  $439,000

  • 2 Beds
  • 2 Baths
  • 1,582 Sq Ft

  313 Lisbon Rd, Canterbury, CT 06331

  Welcome to country living at its finest! Nestled on 5.16 private acres, this impeccably maintained custom ranch offers the perfect blend of comfort, quality, and timeless appeal. Built in 2001, this move-in ready home features 1,582 square feet of thoughtfully designed one-level living with gleaming hardwood floors, central air, first-floor laundry, and an attached two-car garage. The spacious

  Brendan Meehan RE/MAX Bell Park Realty

  313 Lisbon Rd, Canterbury, CT 06331
• 

  

  /11

  $269,000

  • 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
• 

  

  /40

  $850,000

  $145K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 5,176 Sq Ft

  82 Kennerson Reservoir Rd, Ashford, CT 06278

  Experience exceptional waterfront living overlooking the beautiful 88-acre Kennerson Reservoir in scenic Eastford. This impressive 4-bedroom, 3-bath home offers breathtaking panoramic water views and the perfect blend of comfort, recreation, and tranquility. Enjoy kayaking, fishing, boating, swimming, and access to a shared beach, making every day feel like a getaway. The main level features

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  82 Kennerson Reservoir Rd, Ashford, CT 06278
• 

  

  /40

  $220,000

  • 6 Beds
  • 2.5 Baths
  • 2,700 Sq Ft

  383 Putnam Pike, Dayville, CT 06241

  This listing is for 383 Putnam Pike Only - However, a single family (same owner) is available next door at 385 Putnam Pike, Dayville, CT New roof 2025! 1st Floor: 3BR/1.5BA (potential 4BR reconfiguration), forced hot air heat 2nd Floor: 3BR/1BA, hot water baseboard heat Large walkout basement with expansion potential Newer roof and some replacement windows Needs: flooring, plumbing, kitchen/bath

  Anthony Chabot Chabot & Associates Real Estate

  383 Putnam Pike, Dayville, CT 06241
• 

  

  /39

  $420,000

  • 2 Beds
  • 2 Baths
  • 1,446 Sq Ft

  4 Henry Dr Unit 4, Moosup, CT 06354

  Enjoy carefree, single-level living in the desirable 55+ community of Moosup River Estates! This well-maintained 2-bedroom, 2-bath ranch features an open floor plan with a spacious living and dining area, breakfast bar, granite countertops, walk-in pantry, separate laundry room, air conditioning, and an attached two-car garage. The primary suite offers a walk-in shower and plenty of comfort.

  Cary Marcoux RE/MAX Bell Park Realty

  4 Henry Dr Unit 4, Moosup, CT 06354
• 

  

  /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
• 

  

  /40

  $6,950,000

  • 12 Beds
  • 9 Baths
  • 10,517 Sq Ft

  433 Wrights Crossing Rd, Pomfret Center, CT 06259

  Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799

  Lisa Rollins Team Compass Connecticut, LLC

  433 Wrights Crossing Rd, Pomfret Center, CT 06259
• 

  

  /33

  $314,900

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft

  142 Wilkinson St, Putnam, CT 06260

  Looking for a home with solid bones, a convenient location, and room to make it your own? This 3-bedroom, 1-bath ranch is tucked away in a residential neighborhood while still being just a short walk to the shops, restaurants, and charm of downtown Putnam. Inside, you'll find a welcoming fireplace anchoring the living room, an open kitchen and dining area that's perfect for everyday living and

  Rachael Johnston Johnston & Associates Real Estate, LLC

  142 Wilkinson St, Putnam, CT 06260
• 

  

  /18

  $75,000

  • 2 Beds
  • 1 Bath
  • 450 Sq Ft

  25 Route 197, Woodstock, CT 06281

  Looking for your "Seasonal Home Away from Home" Look no further this cute as a button, privately situated park model. Fresh new updates and newly applied finishing touches, makes this unit able to just move on in and start enjoying the rest of the season. Just steps from the amenities. pool, pavilion, mini golf, cornhole field, basketball and short walk to the catch and release fishing pond.

  KAREN MILHEM Media Realty Group, Inc.

  25 Route 197, Woodstock, CT 06281
• 

  /2

  $100,000

  • Land
  • 8.5 Acres
  • $11,765 per Acre

  43 Fall Brook Rd, Danielson, CT 06239

  lovely 8.5 acre lot , raw land

  Ned Murtha Coastal Properties Group

  43 Fall Brook Rd, Danielson, CT 06239
• 

  

  /33

  $585,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  1 Finn Ln, Plainfield, CT 06374

  Welcome home to this charming colonial nestled on a spacious beautifully maintained lot. Offering timeless curb appeal and plenty of room to spread out. Step outside to enjoy the expansive backyard perfect for entertaining, gardening, outdoor games or simply relaxing. Large unfinished room over garage offers more living space. This home has been lovingly cared for and is just waiting for you.

  Robin Keator Compass Connecticut, LLC

  1 Finn Ln, Plainfield, CT 06374
• 

  

  /13

  $315,000

  • 4 Beds
  • 2 Baths
  • 1,890 Sq Ft

  11 Type Rd, South Windham, CT 06266

  Investors and owner-occupants take notice! Well-maintained fully rented, with tenants in place, two-family home situated on a quiet dead-end street. Each unit offers 2 bedrooms, 1 full bath, and approximately 1,000 square feet of living space, providing spacious layouts and strong rental appeal. Separate utilities make management simple, while laundry hookups in the basement add convenience for

  Stephen Galinat Home Selling Team

  11 Type Rd, South Windham, CT 06266
• 

  /2

  $90,000

  • Land
  • 5.09 Acres
  • $17,682 per Acre

  35 Brooklyn Rd, Canterbury, CT 06331

  Located in area of new homes. Slightly wooded. Great location to build your new home.

  Maura Von Deck Von Deck Realty, LLC

  35 Brooklyn Rd, Canterbury, CT 06331
• 

  

  /12

  $100,000

  • 1 Bed
  • 1 Bath
  • 744 Sq Ft

  32 Breezy Ln, Quinebaug, CT 06262

  Affordable homeownership opportunity! This single-wide mobile home is situated on a desirable back lot within a friendly community, offering a peaceful and quiet setting. The home features an eat-in kitchen, comfortable living room, two bedrooms, one full bathroom, a screened-in porch, and a handicap-accessible ramp for added convenience. Outside, you'll find two separate storage sheds providing

  Bonnie MacDonald Berkshire Hathaway NE Prop.

  32 Breezy Ln, Quinebaug, CT 06262
• 

  

  /32

  $789,000

  Open Sat 10AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  25 Colbridge Rd, Plainfield, CT 06374

  Welcome to 25 Colbridge Road, Plainfield, CT! Set on 5.6 private acres, this exceptional 3-bedroom, 2.5-bath cape offers 2,410 square feet of thoughtfully designed living space, combining timeless charm with modern amenities and endless potential. Step inside to discover beautiful birch hardwood floors, abundant natural light, and a spacious floor plan perfect for both everyday living and

  Greg Lehto William Pitt Sotheby's Int'l

  25 Colbridge Rd, Plainfield, CT 06374
• 

  

  /30

  $470,000

  • 5 Beds
  • 3 Baths
  • 3,050 Sq Ft

  0 Plainfield Pike, Sterling, CT 06377

  Built in 1825 in the Quaint town of Oneco this Adorable 3 Family on Oneco Pond is a great Waterfront Property!!! In the Summertime enjoy Kayaking, Canoeing, Swimming, Fishing or just sit and enjoy the Beautiful Views of the Pond from the deck or back yard. In the Winter enjoy Ice Skating or Ice Fishing. Home has 3 units. Two units have 2 Bedrooms and 1 Full Bath and 1 unit has 1 Bedroom and 1

  Ginny Dunbar RE/MAX One

  0 Plainfield Pike, Sterling, CT 06377
• 

  

  /39

  $880,000

  • 4 Beds
  • 5 Baths
  • 5,087 Sq Ft

  48 Grey Fox Landing, Woodstock, CT 06281

  Welcome to this exceptional custom-built ranch, perfectly situated at the end of a peaceful cul-de-sac in South Woodstock. Offering a great blend of luxury, comfort, and versatility, this impressive home boasts 2,822 square feet of beautifully designed main-level living space, with over 5000 square feet of total finished living area including the private in-law apartment above the garage and the

  Lynn Converse RE/MAX Bell Park Realty

  48 Grey Fox Landing, Woodstock, CT 06281
• 

  

  /10

  $850,000

  • 9 Beds
  • 7 Baths
  • 5,402 Sq Ft

  34 Marshall St, Putnam, CT 06260

  Turnkey multifamily investment opportunity in the heart of Putnam, CT. This 7-unit building offers immediate cash flow with a strong unit mix and meaningful recent capital improvements. The property comprises five (5) one-bedroom/one-bath units and two (2) two-bedroom/one-bath units across 5,402 square feet on a 6,500 SF lot. All units have been updated and the building has seen significant

  Jonathan Minerick Homecoin.com

  34 Marshall St, Putnam, CT 06260

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