Windham County CT Homes for Sale

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  /2

  $250,000

  • Land
  • 61 Acres
  • $4,098 per Acre

  0 Parish Hill Rd, Chaplin, CT 06230

  Approx 61 acres with 1600 feet frontage. Undeveloped land. Property is an abandoned orchard, Christmas tree farm.

  Donald Fish D.W. Fish Real Estate

  0 Parish Hill Rd, Chaplin, CT 06230
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  /2

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,136 Sq Ft

  55 Tuckie Rd, Windham, CT 06280

  Colonial style home ready for a new owner. Many recent updates have been completed. New kitchen with stainless steel appliances, new flooring, bathrooms have been updated, freshly painted. This home wonderful for entertaining and enjoyment. Kitchen w/eat in area, living room, dining room. Master bedroom with full bathroom and additional bedrooms and bathroom on second level. This is a MUST see !!

  Mary Beth Malin Brunet and Company Real Estate

  55 Tuckie Rd, Windham, CT 06280
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  /40

  $598,900 Open House 1/18

  • 4 Beds
  • 2.5 Baths
  • 4,706 Sq Ft

  76 John Brook Rd, Canterbury, CT 06331

  Set on a scenic 4.58-acre private lot, this beautifully maintained Cape offers space, comfort, and recent upgrades in a peaceful Canterbury setting. With approximately 2,920 sq ft of living space, the home features 4 bedrooms, 2 full baths, 1 half bath, and a versatile floor plan well suited for both everyday living and entertaining. Recent improvements add tremendous value, including a new

  Veronica (Ronnie Tosoni eXp Realty

  76 John Brook Rd, Canterbury, CT 06331
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  /32

  $725,000

  • 3 Beds
  • 1.5 Baths
  • 2,232 Sq Ft

  204 Paine Rd, Pomfret, CT 06259

  First time offered in over 50 years, this c.1820 home has been updated and very well maintained with craftsmanship and charm. Rich and warm with wood and natural light, comfortable kitchen, large dining room, and a wood burning fireplace in the living room. The original Cape portion of the house has 3 rooms and a half bath on the 2nd level. The primary bedroom is on the main floor. With over

  Lynn Converse RE/MAX Bell Park Realty

  204 Paine Rd, Pomfret, CT 06259
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  /21

  $349,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 2,326 Sq Ft

  250 Child Rd, Woodstock, CT 06281

  Unlock the potential of this 3-bedroom, 2-bathroom home, being SOLD AS-IS and ready for your creative vision! This property is perfect for those looking to make a house their dream home with a full remodel. In addition to the home, you'll find a spacious barn in excellent condition, ideal for a workshop, business venture, or barn-to-home conversion. The barn features a large workshop, car bay,

  Joseph Murphy CR Premier Properties

  250 Child Rd, Woodstock, CT 06281
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  /37

  $359,900 Open Sat 10AM - 12PM

  • 3 Beds
  • 1 Bath
  • 1,386 Sq Ft

  130 Church St, Moosup, CT 06354

  Welcome home to a thoughtfully designed Cape that blends modern efficiency, outdoor space, and everyday comfort. Built in 2015, this move-in-ready 3 bedroom, 1 bath home offers 1,386 square feet of open-concept living in Plainfield, CT. The kitchen, dining, and living room feature scratch-resistant flooring, a butcher block kitchen island, black stainless steel appliances, and dining room

  Shiloh Therrien The Neighborhood Realty Group

  130 Church St, Moosup, CT 06354
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  /16

  $289,000

  • 4 Beds
  • 1 Bath
  • 1,180 Sq Ft

  933 Hampton Rd, Pomfret, CT 06259

  Located in the quiet, rural town of Pomfret, Connecticut, this 1,180 square foot single-family home offers four bedrooms and one full bathroom in a peaceful New England setting. The flexible layout provides options for bedrooms, home offices, or guest space to suit a variety of needs. The home features maintenance-free vinyl siding, a durable metal roof, and replacement windows, offering

  Paul Stone Kazantzis Real Estate, LLC

  933 Hampton Rd, Pomfret, CT 06259
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  /40

  $360,000 Open Sat 11AM - 12:30PM

  • 2 Beds
  • 2 Baths
  • 1,259 Sq Ft

  50 Richmond Rd Unit 10, Putnam, CT 06260

  Well-maintained 2-bedroom, 2-full-bath condo offering an open and inviting floor plan filled with natural light. The main level features spacious living and dining areas that flow seamlessly to a private deck-perfect for relaxing or entertaining. The finished walk-out lower level adds exceptional versatility with a comfortable family room, den, and dedicated office space. Additional highlights

  Cary Marcoux RE/MAX Bell Park Realty

  50 Richmond Rd Unit 10, Putnam, CT 06260
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  /23

  $399,999 Open Sun 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 2,077 Sq Ft

  77 Charlotte Dr, Plainfield, CT 06374

  Spacious 3 bedroom, 2 bath built in 1988, Cape set on level .70 acre corner lot. There is Vinyl siding, newer roof, newer hot water heater, 200 Amp electrical panel. First floor primary suite, open kitchen to dining area, hardwood floors, 2 car garage, city water & sewer plus central air! Above ground pool, solar panels in place, contract to be assumed by buyer. Room above garage is heated with

  Brittany Summers Real Broker CT, LLC

  77 Charlotte Dr, Plainfield, CT 06374
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  /19

  $190,000

  • 2 Beds
  • 1 Bath
  • 780 Sq Ft

  115 North Rd, Ashford, CT 06278

  Better than renting! YOU BET! NO HOA costs here. Mobile Home on its own lot. Occupy your own personal private space in this 2-bedroom Mobile Home. Nicely remodeled for move-in ready convenience. 2-bedrooms, full bath with double sinks. Large livingroom open to fully applianced kitchen with lots of storage. Just off the kitchen is the rear mudroom and laundry area with washer - dryer hookups.

  Roberta Cardinal RbRE, LLC

  115 North Rd, Ashford, CT 06278
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  /39

  $279,999 Open Sat 11AM - 1PM

  • 3 Beds
  • 1 Bath
  • 1,344 Sq Ft

  259 Church St, Putnam, CT 06260

  Open House Saturday, 1/10 11am-1pm & Sunday, 1/11 11am-1pm. Step inside this beautifully renovated Colonial in the heart of Downtown Putnam-a perfect blend of timeless character and modern updates. This 3-bedroom, 1-bath home offers 1,344 square feet of thoughtfully refreshed living space. The main level welcomes you with refinished hardwood floors leading into a brand-new kitchen featuring

  Caleb Nadeau Chabot & Associates Real Estate

  259 Church St, Putnam, CT 06260
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  /2

  $400,000

  • Land
  • 3.2 Acres
  • $125,000 per Acre

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332

  3.2 corner lot located at the Wauregan four corners. Currently zoned residential but has commercial potential. Buyer's and buyers agent to do all of your own due diligence with the town.

  Cary Marcoux RE/MAX Bell Park Realty

  0 Putnam Rd Unit 24147722, Plainfield, CT 06332
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  /29

  $439,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft

  8 John's Cir Unit Lot 33, Sterling, CT 06377

  * NEW CONSTRUCTION * 30 days from completion and still time to choose some selections. Welcome to Sterling Hills Estates, where luxury meets convenience! This Brand New 2024 to be built 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

  Patrick Farrell Compass Connecticut, LLC

  8 John's Cir Unit Lot 33, Sterling, CT 06377
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  /40

  $899,900 New Construction

  • 3 Beds
  • 3 Baths
  • 2,200 Sq Ft

  121 New Rd, Thompson, CT 06277

  Welcome to your dream retreat-a stunning 2026 new construction custom raised ranch offering unparalleled luxury, craftsmanship, and privacy on nearly 19 acres of pristine land. This meticulously designed 2,200 square foot home combines modern elegance with timeless appeal, perfect for those seeking a serene escape with endless potential, whether as a private estate, horse property, or development

  Daniel Deojay RE/MAX Bell Park Realty

  121 New Rd, Thompson, CT 06277
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  /12

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,896 Sq Ft

  408 Huntington Rd, Scotland, CT 06264

  Enjoy the tranquility of Scotland living. Quiet surroundings with minimal through traffic and plenty of privacy. This colonial features 3 bedrooms and 2 full bath. The second floor was made into an apartment perfect for multigenerational living. The property also features a detached barn as well as a detached 2 car garage.

  Nicole Garbutt RE/MAX Bell Park Realty

  408 Huntington Rd, Scotland, CT 06264
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  /40

  $350,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 1.5 Baths
  • 1,640 Sq Ft

  1250 Route 171, Woodstock, CT 06281

  Welcome to this charming colonial with stenciled details that add character & style! This delightful antique property is the perfect fixer upper and features 3 bedrooms, 1 and a 1/2 bathrooms, and a clapboard exterior. Situated on a 0.9 acre lot, this home boasts a garden in the side yard and a large backyard, perfect for outdoor enjoyment. Additionally, a shed provides convenient storage for

  Kara Mazzola First Choice Realty

  1250 Route 171, Woodstock, CT 06281
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  /18

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 1,200 Sq Ft

  29 Prospect St Unit A, Putnam, CT 06260

  Welcome to 29 Prospect St Unit A....a turnkey half-duplex that delivers easy living and everyday comfort in the heart of Putnam. This updated 3-bedroom, 1.5-bath home checks all the boxes with a bright, open layout and low-maintenance features throughout. Step inside to find refinished hardwood floors, freshly carpeted bedrooms, and central air to keep things cool and comfortable all summer long.

  Kendra Bonette Coldwell Banker Realty

  29 Prospect St Unit A, Putnam, CT 06260
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  /32

  $439,999

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  370 Tripp Hollow Rd, Brooklyn, CT 06234

  This beautiful 3-bedroom, 2-bath home sits on a quiet dirt road, offering peaceful living with modern peace of mind. The seller is relocating, and the sale is in no way any fault of the home. Inside, you'll find a full walkout basement with incredible potential for future living space, storage, or customization. Recent updates include a new water bladder and new refrigerator. The fenced-in front

  Ashley Walker Brunet and Company Real Estate

  370 Tripp Hollow Rd, Brooklyn, CT 06234
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  /17

  $389,900

  • 4 Beds
  • 2 Baths
  • 1,611 Sq Ft

  75 Lovers Ln, Plainfield, CT 06374

  Charming Country Farmhouse on 3.5 acres. This inviting home blends classic character with rural tranquility offering the perfect retreat from the bustle of everyday life. 4 comfortable bedrooms with 2 full baths within effortlessly flowing living space. The large, heated sunroom is the perfect place to spend time with family or guests. This property not only offers an oversized 2 plus car

  Monique Rouillard Signature Properties of NewEng

  75 Lovers Ln, Plainfield, CT 06374
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  /16

  $480,000

  • 11 Beds
  • 3 Baths
  • 3,748 Sq Ft

  30 Main St, Plainfield, CT 06374

  Nestled in the heart of history, this extraordinary three-level estate exudes timeless elegance and vintage charm. With soaring ceilings, sprawling rooms, and intricate architectural details, this home captures the essence of a bygone era while offering the space and amenities for today's lifestyle. Every corner of this impressive residence tells a story-from the grand entryway with original

  Adam Gonzalez Century 21 Limitless

  30 Main St, Plainfield, CT 06374
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  /34

  $375,000

  • 4 Beds
  • 2 Baths
  • 2,014 Sq Ft

  117 Woodside St, Putnam, CT 06260

  This home gets the fundamentals right: space, light, flow, and condition. From the outside, the classic Garrison Colonial profile sets the right expectations with its private fenced-in, level rear yard. Still, the real value is inside. The main level offers an intuitive layout anchored by a front-to-back living room. Exposed beams add warmth and architectural interest, while the scale easily

  Beth Fournier Compass Connecticut, LLC

  117 Woodside St, Putnam, CT 06260
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  /39

  $329,900 Open Sun 12PM - 2PM

  • 5 Beds
  • 3 Baths
  • 2,560 Sq Ft

  18 Broad St, Danielson, CT 06239

  Beautifully Maintained Two-Family Home in the Heart of Danielson, CT Discover the perfect opportunity for owner-occupants or investors with this spacious and well-kept two-family home located in a convenient Danielson neighborhood. This property features two generously sized units offering comfort, functionality, and excellent rental potential. Unit 1: 3 Bedrooms * 2 Bathrooms The first unit

  Ryan Newport Social & Co Realty

  18 Broad St, Danielson, CT 06239
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  /39

  $875,000

  • 3 Beds
  • 3 Baths
  • 2,668 Sq Ft

  95 Old Breakneck Hill Rd, Dayville, CT 06241

  Horse property. Private setting. Custom built Colonial home. 3 bedrooms, 3 full bathrooms, open floor plan, formal dining room, Large kitchen with a center island, granite counters, SS appliances. Living room with a gas fireplace, cathedral ceiling and sliders to your private deck. Home office on the first floor. Full bathroom with laundry on the first floor. Hardwoods throughout the house.

  Mark Benard Brunet and Company Real Estate

  95 Old Breakneck Hill Rd, Dayville, CT 06241
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  /27

  $369,900

  • 3 Beds
  • 2 Baths
  • 1,488 Sq Ft

  150 Searles Rd, Pomfret Center, CT 06259

  Right on the Mass and RI line sits this SPACIOUS Ranch with NEW 10 x25 CONCRETE PATIO, freshly painted 26 x 10 DECK to enjoy your SPRING evenings and a 12 x 10 DECK in the back of home. Sits on 3.18 PRIVATE acres (land is hilly but NO neighbors in back or to the side!) TILED entryway leads to BEAUTIFUL HARDWOOD floor in Living room with pellet stove (CONVEYING) OPEN to LARGE TILED, APPLIANCE

  Christine Johnson RE/MAX One

  150 Searles Rd, Pomfret Center, CT 06259
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  /40

  $525,000

  • 3 Beds
  • 2 Baths
  • 1,930 Sq Ft

  414 Canterbury Rd, Brooklyn, CT 06234

  Start the new year off right in this 3 bedroom, 2 bath sprawling ranch. There are two very large living rooms both with fireplaces. Close the pocket doors to add privacy. Step out onto the back deck and enjoy the sights & sounds of Blackwell Brook & the adjoining Creek. The brook is stocked with trout. The hill is great for sledding! Sit on the front porch and watch the pool parties next summer

  Jennifer Metivier Diversified Real Estate, LLC

  414 Canterbury Rd, Brooklyn, CT 06234
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  /40

  $514,900 Open Sun 12PM - 2PM

  • 3 Beds
  • 2 Baths
  • 3,124 Sq Ft

  125 Hanover Rd, Baltic, CT 06330

  Set back from the road on a private, level 3.26-acre lot, this stunning 3,124 sq ft home offers space, comfort, and a perfect blend of indoor and outdoor living. Lightly wooded and peaceful, the property provides the privacy you crave while still being conveniently located. Inside, you'll find 3 spacious bedrooms and 2 full bathrooms, with an inviting open family room that truly steals the

  Caitlyn Chilly Countryside Realty

  125 Hanover Rd, Baltic, CT 06330
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  /23

  $589,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,800 Sq Ft

  890 Brook Rd, Hampton, CT 06247

  GORGEOUS 2026 Raised Ranch on almost 2 ACRES in Hampton is ready! 16 x 16 DECK to enjoy your SPRING evenings. SHINY HARDWOOD floors throughout main level w/ VAULTED open floor plan for entertaining. QUARTZ counters, STAINLESS appliances and LARGE island next to dining room and living room w/ bright windows for natural light. Primary bedroom has VAULTED ceiling and a BEAUTIFUL bathroom w/ GLASS

  Christine Johnson RE/MAX One

  890 Brook Rd, Hampton, CT 06247
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  /7

  $345,000

  • 3 Beds
  • 2 Baths
  • 1,176 Sq Ft

  25 Korpita Rd, Danielson, CT 06239

  Ranch style home with many recent updates. Offered here is kitchen, living room, 3 bedrooms and 2 full bathrooms. The Seller has completed the updates so all you have to do is move in. New kitchen with stainless steel appliances, updated bathrooms, new flooring, freshly painted. Do not miss out on this adorable home !!

  Mary Beth Malin Brunet and Company Real Estate

  25 Korpita Rd, Danielson, CT 06239
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  /35

  $450,000

  • 3 Beds
  • 2 Baths
  • 1,806 Sq Ft

  100 Squaw Rock Rd, Plainfield, CT 06353

  Welcome to this stunning newer-built Cape Cod home, completed in 2022, perfectly blending timeless charm with modern comfort. Nestled on 3 acres in a secluded part of town. Step inside to find an inviting floor plan with oak hardwood flooring, primary bedroom on the main floor and thoughtful details throughout. The spacious living area flows seamlessly into a modern kitchen with stainless steel

  Robert Wallace Real Broker CT, LLC

  100 Squaw Rock Rd, Plainfield, CT 06353
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  /25

  $449,900 Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 1,547 Sq Ft

  43 Tatnic Hill Rd, Brooklyn, CT 06234

  Located on a quiet dead-end road, 43 Tatnic Hill Road is a move-in ready, well-cared-for Cape built in 2016. The main level features hardwood floors throughout and a comfortable, open layout with a bright kitchen and dining area, first-floor laundry, and access to the back deck. All three bedrooms are located upstairs, including a primary bedroom with an en suite full bath, along with an

  Kelsie Griffin Wolfburg Signature Properties of NewEng

  43 Tatnic Hill Rd, Brooklyn, CT 06234
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  /8

  $284,900

  • 4 Beds
  • 1 Bath
  • 1,288 Sq Ft

  12 Mechanic St, Moosup, CT 06354

  new kitchen with quartz countertops, bathrooms, windows, appliances, water heater, boiler, waterproof flooring, paint

  Samuel Peralta Berkshire Hathaway NE Prop.

  12 Mechanic St, Moosup, CT 06354
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  /4

  $89,000

  • Land
  • 1.3 Acres
  • $68,462 per Acre

  0 Thompson Rd Unit 3H, Thompson, CT 06277

  Build your dream home in the peaceful town of Thompson, where privacy, space, and New England charm come together. This residential lot offers the perfect setting for a custom home surrounded by nature, while still providing convenient access to major routes, nearby towns, and everyday amenities. Thompson is known for its scenic landscapes, rural character, and strong sense of community-ideal for

  The Schlesman Realty Group ERA Key Realty Services

  0 Thompson Rd Unit 3H, Thompson, CT 06277
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  /40

  $335,000 Open Sat 11AM - 1PM

  • 6 Beds
  • 2 Baths
  • 2,414 Sq Ft

  78 S Walnut St, Wauregan, CT 06387

  This 2-family home has new appliances, 3 bedrooms and first floor laundry in each unit with separate utilities. Plenty of parking with driveways on each side, a nice level lot that's perfect for outdoor entertaining with a gazebo and a new pergola as well as a re-built garage/workshop with a newly poured concrete floor. Great opportunity for investors seeking a consistent income stream or an

  Loni Wright RE/MAX Bell Park Realty

  78 S Walnut St, Wauregan, CT 06387
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  /38

  $399,900 Open Sat 11:30AM - 1PM

  • 6 Beds
  • 2 Baths
  • 2,426 Sq Ft

  129 Mechanics St, Putnam, CT 06260

  Well maintained two family home in Putnam with a huge double lot. 3 bedroom, 1 bath unit on each floor. The upper unit is accessed directly from the driveway and features all gleaming hardwood floors throughout. The lower unit offers a mix of hardwood floors and carpeted rooms. Both units include fresh paint, in unit laundry rooms with hookups, and separate utilities. One unit is heated by

  Jeremy Bailey SkyView Realty

  129 Mechanics St, Putnam, CT 06260
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  /40

  $599,000

  • 2 Beds
  • 2 Baths
  • 3,208 Sq Ft

  55 Island Rd, Dayville, CT 06241

  Escape the every day at 55 Island Road - your private lakeside retreat on Alexander's Lake. Estate property, professionally cleaned out - ready to move right in. Built in 1985 with a brand-new oil tank, this Classic Cape needs cosmetic update - new floors, paint, maybe a kitchen refresh - gives 2,120 square feet of cozy without compromise. Two generous bedrooms, with the possibility of a third

  Michelle Richardson Kazantzis Real Estate, LLC

  55 Island Rd, Dayville, CT 06241
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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
• 

  

  /3

  $150,000

  • Land
  • 22.8 Acres
  • $6,579 per Acre

  0 W Thompson Rd Unit 24146108, Thompson, CT 06255

  0 Thompson Road offers a picturesque 22.8 acre mixed-use commercial land opportunity located in the BDD (Business Development District) zone, allowing for energy storage, agricultural operations, multi-family housing (special permit), and light manufacturing, subject to Town Planning & Zoning approval. Gentle Slopping Bordered by the French River and North Grosvenordale Pond, the site includes

  Michael Collins Berkshire Hathaway NE Prop.

  0 W Thompson Rd Unit 24146108, Thompson, CT 06255
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  /4

  $89,000

  • Land
  • 0.93 Acre
  • $95,699 per Acre

  0 Thompson Rd Unit Lot 3G, Thompson, CT 06277

  Build your dream home in the peaceful town of Thompson, where privacy, space, and New England charm come together. This residential lot offers the perfect setting for a custom home surrounded by nature, while still providing convenient access to major routes, nearby towns, and everyday amenities. Thompson is known for its scenic landscapes, rural character, and strong sense of community-ideal for

  The Schlesman Realty Group ERA Key Realty Services

  0 Thompson Rd Unit Lot 3G, Thompson, CT 06277
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  /17

  $95,000

  • Land
  • 3.86 Acres
  • $24,611 per Acre

  Lot 13A Somers Turnpike, Woodstock, CT 06281

  Located in the heart of Woodstock on the scenic Somers Turnpike, this nearly 4-acre elevated lot offers you the perfect setting for your dream home. A long driveway will lead you to a secluded potential home site with stone walls, lush landscape and beautiful sunsets. There is a recent plot survey and a perc test (11/2025), which will be available upon request. The property has 113 feet of road

  Brenda Chubbuck CR Premier Properties

  Lot 13A Somers Turnpike, Woodstock, CT 06281
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  /20

  $359,900 Open Sun 11AM - 1PM

  • 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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