Windham County CT Houses for Sale

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  /39

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 2,123 Sq Ft

  1 Library Rd, Canterbury, CT 06331

  Welcome to 1 Library Road, a beautifully updated antique Colonial nestled in the heart of Canterbury's Historic District. Built circa 1807, this classic home combines historic charm with modern improvements on a generous 1.15-acre corner lot just steps from the Canterbury Center Historic District and village green, which features fine 18th- and early 19th-century architecture and cultural

  Kristopher Tramont Real Broker CT, LLC

  1 Library Rd, Canterbury, CT 06331
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• 

  

  

  /37

  $325,000

  • 3 Beds
  • 2.5 Baths
  • 1,228 Sq Ft

  15 Cracow Ave, Windham, CT 06280

  Welcome to this inviting 3-bedroom, 2-bath ranch featuring a 1-car garage and a fantastic layout perfect for comfortable everyday living. Placed right along side the Natchaug River used for fishing and kayaking! Step inside to find a bright, open floor plan with warm natural light and easy flow throughout. Outside, the property truly shines. Enjoy summer days in your beautiful inground pool (with

  Julienne Jaber KW Legacy Partners

  15 Cracow Ave, Windham, CT 06280
• 

  

  

  /19

  $244,900

  • 6 Beds
  • 1.5 Baths
  • 1,701 Sq Ft

  22 Grove St, Sterling, CT 06377

  Spacious 6-Bedroom Home in Sterling, CT Welcome to this generously sized 6-bedroom, 1.5-bath home ideally located in the quiet town of Sterling, CT. Set directly next to a neighborhood park, this property offers a rare combination of space, privacy, and outdoor enjoyment-perfect for those seeking room to grow or invest. Inside, you'll find a flexible layout with ample living space, large

  Tyler Amann Social & Co Realty

  22 Grove St, Sterling, CT 06377
• 

  

  

  /17

  $269,900

  • 3 Beds
  • 2 Baths
  • 1,836 Sq Ft

  9 Hammond St, Putnam, CT 06260

  Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $2,699 back in closing costs credits OR $1,457 per month at an exceptional financing rate of 5.05% APR with ZERO down payment available for those who qualify. our Private Oasis Awaits Spacious Home in a Highly Sought-After Location! This well-maintained property offers

  Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

  9 Hammond St, Putnam, CT 06260
• 

  

  

  /31

  $589,900 New Construction

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

  890 Brook Rd, Hampton, CT 06247

  STEP over the CT. Line and come view this 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

  Christine Johnson RE/MAX One

  890 Brook Rd, Hampton, CT 06247
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  /37

  $589,000 Coming Soon

  • 3 Beds
  • 3.5 Baths
  • 2,646 Sq Ft

  436 Providence Pike, Putnam, CT 06260

  Set back from the road on 2 private acres, this 2,646 sq ft Colonial offers space, flexibility, and potential for an accessory dwelling unit (ADU) or in-law setup in the lower level. The main level features a spacious living room with hardwood floors and fireplace with wood stove insert, Den with tile flooring (ideal for gym, rec room, or future sunroom), a dedicated office, and a half bath. The

  Shiloh Therrien The Neighborhood Realty Group

  436 Providence Pike, Putnam, CT 06260
• 

  

  /30

  $975,000

  • 2 Beds
  • 2 Baths
  • 2,895 Sq Ft

  564 Hubbard Rd, Danielson, CT 06239

  Back on the market with fresh updates! Tucked at the end of a winding country drive through open meadow, this distinctive contemporary retreat sits on over 12 private acres. The property features a beautifully remodeled 3 bedroom, 2 bath home offering approximately 2,800 sq ft of living space, along with an impressive heated and air-conditioned four-bay garage with office loft-ideal for

  C. Tina Pappalardo Coldwell Banker Realty

  564 Hubbard Rd, Danielson, CT 06239
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  /39

  $549,000

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  101 Child Hill Rd, Woodstock, CT 06281

  Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases

  Kristen Kaskela Berkshire Hathaway NE Prop.

  101 Child Hill Rd, Woodstock, CT 06281
• 

  

  /36

  $485,000

  • 3 Beds
  • 2 Baths
  • 2,170 Sq Ft

  395 Bailey Hill Rd, Danielson, CT 06239

  RENOVATED RANCH Style home situated on .92 acres. Finishing touches being completed on this 3BR, 2BA home boasting approx. 2,820 sq. ft. of total living area. Open flow on the main level starting with a fully renovated kitchen w/Granite counter tops, New cabinets, all New appliances and tiled floor. Original Hardwood flooring throughout the remainder of the main level living room, hallway and

  Chris Campolito Campolito Realty Group

  395 Bailey Hill Rd, Danielson, CT 06239
• 

  /2

  $549,999 Open House 4/11

  • 6 Beds
  • 3 Baths
  • 3,496 Sq Ft

  28 Walas Rd, Moosup, CT 06354

  Completely remodeled and move-in ready, this beautifully updated home in Plainfield offers modern comfort with versatile living space and all the bells & whistles! Featuring 6 bedrooms and 3 bathrooms, the main residence includes a brand-new kitchen with updated cabinetry, and countertops along with refreshed bathrooms, new flooring, and fresh paint throughout. Den with fireplace and entry to

  Amy Brunet Brunet and Company Real Estate

  28 Walas Rd, Moosup, CT 06354
• 

  

  /26

  $439,000

  • 4 Beds
  • 2 Baths
  • 1,787 Sq Ft

  7 Devotion Rd, Windham, CT 06280

  Nestled in the peaceful, rural charm of Scotland, CT, this lovingly updated 9-room, 4-bedroom, 2-bathroom home delivers the perfect blend of comfort, character, and modern convenience. From the moment you arrive, you'll feel the embrace of home - and see endless opportunities for family life here. This home is ready for your life to unfold - from quiet weekday mornings to lively gatherings. Step

  Alexia Andrade US Asset Realty

  7 Devotion Rd, Windham, CT 06280
• 

  

  /12

  $214,900

  • 4 Beds
  • 1 Bath
  • 1,865 Sq Ft

  29 Union St, Moosup, CT 06354

  Check out this spacious Cape Cod located in Moosup! Featuring 4-bedrooms and a living area upstairs, as well as a lovely and open main floor, this home has a lot to offer. Property features a partially fenced yard located in a neighborhood with many young families. This home received many renovations in 2023 including a roof. This property may qualify for Seller Financing (Vendee). If property

  Ryan King Aspen Realty Group

  29 Union St, Moosup, CT 06354
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  /36

  $319,900

  • 3 Beds
  • 1 Bath
  • 1,423 Sq Ft

  151 Brandy Hill Rd, Thompson, CT 06277

  Antique-style farmhouse with over one acre of open land for gardening or your new inground pool! Home has 3 bedrooms and one bath. Large front-to-back living room with sliders out to a wrap-around deck. Kitchen with stove, refrigerator, dishwasher and washer/dryer hookups. Two large bedrooms on the second floor with ample hallway space to serve as a small den. Third bedroom on the first floor.

  Joann Hall RE/MAX Bell Park Realty

  151 Brandy Hill Rd, Thompson, CT 06277
• 

  

  /22

  $305,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  361 Pasay Rd, North Grosvenordale, CT 06255

  (More Pictures this week) Welcome to 361 Pasay Road in North Grosvenordale, CT, where peaceful country living meets everyday convenience. Situated on 0.94 acres, this inviting 2-bedroom, 1-bath home offers comfort and thoughtful updates throughout, including a beautiful bathroom and an efficient pellet stove to keep you warm during New England winters. Just minutes from Route 395, the property

  Andrew Whitehead The Neighborhood Realty Group

  361 Pasay Rd, North Grosvenordale, CT 06255
• 

  

  /10

  $579,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,650 Sq Ft

  4 Bluebird Ln, Dayville, CT 06241

  SIMILAR TO BE BUILT - *173 RT-205 Brooklyn CT* will get you close to subdivision. Brooklyn's FINEST subdivision now offers this one of a kind RANCH style home. The luxurious build is like no other, high end products are used throughout. Attention to detail through each step, put together by local luxury builder. Approximately 1650 square foot ranch is now here. 3 bed, 2 baths, MAIN floor laundry!

  Mark Tetreault, II RE/MAX Bell Park Realty

  4 Bluebird Ln, Dayville, CT 06241
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  /40

  $794,900

  • 3 Beds
  • 2 Baths
  • 2,282 Sq Ft

  17 Blackwells Landing, Brooklyn, CT 06234

  Welcome to 17 Blackwells Landing in the charming town of Brooklyn, Connecticut-where privacy, space, and classic New England living come together. Set on just over 12.5 picturesque acres, this beautifully maintained home offers nearly 2,300 square feet of living space with tasteful updates throughout, creating a perfect balance of comfort and modern appeal. Inside, you'll find spacious living

  Andrew Hogan Brian Buonaiuto

  17 Blackwells Landing, Brooklyn, CT 06234
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  /40

  $519,000

  • 3 Beds
  • 2 Baths
  • 1,862 Sq Ft

  70 Crandall Ln, Canterbury, CT 06331

  Find your perfect country retreat in this beautiful updated colonial home, situated on a 2.16 acres on serene cul-de-sac, is move in ready. This property showcases 3 bedrooms, 2 full baths, an office, a formal dinning area and a mud room perfect for shedding shoes. The home features a new pellet stove, new split unit in mud room and the roof updated was updated in 2023. The front porch invites

  Lisa Weagle Kazantzis Real Estate, LLC

  70 Crandall Ln, Canterbury, CT 06331
• 

  

  /40

  $599,900

  • 4 Beds
  • 3.5 Baths
  • 2,944 Sq Ft

  369 Thompson Rd, Thompson, CT 06277

  In the heart of Thompson Hill, step into history with the Jeremiah Olney House owned by the famous banker Jeremiah Olney in 1860, with its significant Greek Revival and Italianate features. This stunning 4-bed, 3.5-bath colonial farmhouse sits on nearly an acre of picturesque land and has been completely renovated. Overflowing with character, this home blends classic charm with modern

  Sheena Ruggirello Real Broker CT, LLC

  369 Thompson Rd, Thompson, CT 06277
• 

  

  /24

  $619,000 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,204 Sq Ft

  277 Moosup Pond Rd, Plainfield, CT 06354

  Exciting NEW listing in a charming NEW subdivision! LAST ONE! make it YOURS today!! This stunning colonial home features 4 bedrooms and 2.5 baths, perfect for family living. The open layout creates a welcoming atmosphere, highlighted by a beautiful kitchen with quartz countertops and a large island ideal for entertaining. The master suite is conveniently located on the main floor, offering

  Paige Collelo Taber Realty, LLC

  277 Moosup Pond Rd, Plainfield, CT 06354
• 

  

  /40

  $474,900

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

  125 Hagstrom Rd, Thompson, CT 06277

  *Actual SQ Ft 1764* Town card is being updated. Welcome to your dream farmhouse retreat-completely renovated and privately set on nearly 2 acres of serene natural beauty. The inviting front porch sets the tone for peaceful mornings and quiet evenings. Inside, timeless charm meets modern updates. The stunning kitchen features marble countertops, a large basin sink, stainless steel appliances,

  Sheena Ruggirello Real Broker CT, LLC

  125 Hagstrom Rd, Thompson, CT 06277
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  /36

  $349,900

  • 3 Beds
  • 2 Baths
  • 1,538 Sq Ft

  17 Vine St, Putnam, CT 06260

  Welcome home to this beautifully maintained raised ranch in Putnam! The main level offers a warm and inviting layout featuring a dining room with hardwood floors and a spacious kitchen complete with stainless steel appliances, ample white cabinetry, and a large center island perfect for gathering. Head right out to the deck for easy indoor-outdoor living. Three good-sized bedrooms and a full bath

  Heather Armbruster Lamacchia Realty

  17 Vine St, Putnam, CT 06260
• 

  

  /37

  $399,000

  • 5 Beds
  • 2.5 Baths
  • 3,069 Sq Ft

  38 Canterbury Rd, Brooklyn, CT 06234

  Built in 1829 by Edwin C. Newbury and recognized by the Brooklyn Historic Society, this classic center hall Colonial offers a rare opportunity for true old home enthusiasts to own a meaningful piece of Brooklyn's architectural history. Prominently set in Brooklyn Center along scenic Route 169, the property blends early New England heritage with modern convenience, just a short drive to local

  Adam Gumula Kazantzis Real Estate, LLC

  38 Canterbury Rd, Brooklyn, CT 06234
• 

  

  /24

  $599,900

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

  192 Stawicki Rd, North Grosvenordale, CT 06255

  Set on 1.9 private acres, this beautifully maintained 3-bedroom, 1.5-bath home offers 2,020 square feet of comfortable living space with exceptional charm and versatility. A wraparound farmer's porch creates a warm welcome, while the thoughtfully designed kitchen features granite countertops, newer stainless steel appliances (2020, 2023), and custom cherry cabinetry. New waterproof Lifeproof

  Keri Roy Kazantzis Real Estate, LLC

  192 Stawicki Rd, North Grosvenordale, CT 06255
• 

  

  /28

  $599,900

  • 5 Beds
  • 3 Baths
  • 3,378 Sq Ft

  29 Old Canterbury Rd, Plainfield, CT 06374

  Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $5,999 back in closing cost credits OR $2,591 per month at an exceptional financing rate of 5.05% APR with ZERO down payment available for those who qualify. Your Private Oasis Awaits An Entertainers Dream! Step into a gorgeous open Kitchen with high end cabinets and

  Nathan Clark Your Home Sold Guaranteed Realty, The Nathan Clark Team

  29 Old Canterbury Rd, Plainfield, CT 06374
• 

  

  /22

  $415,000

  • 2 Beds
  • 2 Baths
  • 1,260 Sq Ft

  10 Grace Ln, Moosup, CT 06354

  Welcome to 10 Grace Lane in Moosup River Estates, a desirable 55+ community offering low-maintenance living in a peaceful riverside setting. This nearly new, one-level ranch-style detached condo sits on a quiet cul-de-sac in a friendly neighborhood, the perfect combination of comfort and convenience. Ideally located just 10 minutes from the Rhode Island line and close to shopping and restaurants,

  Kelsey Adams Kelley eXp Realty

  10 Grace Ln, Moosup, CT 06354
• 

  

  /20

  $375,000

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  181 Snake Meadow Rd, Moosup, CT 06354

  This house has been TOTALLY brought back to life! New Roof, Windows, Siding, Doors, Flooring, Paint, Heating System, Oil Tank, Well Tank, Stainless Steel Appliances, Lighting, Two New Bathrooms, Kitchen and More! It also has a BRAND NEW SEPTIC on the way to be installed before closing. Come take a peek before it's gone.

  Derek Greene Derek Greene

  181 Snake Meadow Rd, Moosup, CT 06354
• 

  

  /40

  $399,900

  • 3 Beds
  • 2.5 Baths
  • 1,512 Sq Ft

  167 Armitage Rd, Ashford, CT 06278

  Welcome to this charming Colonial-style home set on a private and picturesque 2.75-acre lot, offering the perfect blend of space, comfort, and seclusion. With over 1,500 square feet of well-designed living space, this 3-bedroom, 2.5-bath residence is ideal for both everyday living and entertaining. The main level features a traditional yet functional layout, including a spacious living room, a

  Chris Torrez RE/MAX One

  167 Armitage Rd, Ashford, CT 06278
• 

  

  /29

  $350,000

  • 3 Beds
  • 1 Bath
  • 1,257 Sq Ft

  37 Cady St, Danielson, CT 06239

  Charming and well-maintained Cape nestled in a quiet Northeast Connecticut location, offering the perfect balance of peaceful living and convenient access to nearby amenities. This inviting home features a spacious living room filled with natural light-ideal for relaxing or entertaining-along with a generously sized dining room perfect for gatherings and holiday dinners. Thoughtful updates

  Vivian Kozey CR Premier Properties

  37 Cady St, Danielson, CT 06239
• 

  

  /36

  $469,000

  • 3 Beds
  • 1.5 Baths
  • 2,003 Sq Ft

  1436 North Rd, Dayville, CT 06241

  Welcome to this charming 3-bedroom, 2-bath ranch located in a desired area on North Road. This classic 1966 brick home offers timeless character with a cozy fireplace and inviting layout. Enjoy newer flooring throughout the main living area and fresh carpeting in the bedrooms for a move-in ready feel. The main bathroom renovation has been started, offering a blank canvas for you to customize to

  Scott Pempek Berkshire Hathaway NE Prop.

  1436 North Rd, Dayville, CT 06241
• 

  

  /39

  $650,000

  • 3 Beds
  • 3 Baths
  • 3,150 Sq Ft

  679 Bailey Hill Rd, Dayville, CT 06241

  This one-of-a-kind custom-built ranch offers over 3,000 sqft on the main level and showcases stunning quality throughout. The living room features vaulted ceilings and a remarkable fieldstone fireplace in the center of the home. Ornate hardwoods flow through the main floor which lead to an updated beautiful kitchen with granite countertops, center island, and gas range. Step out to the refinished

  Robert Sousa Redfin Corporation

  679 Bailey Hill Rd, Dayville, CT 06241
• 

  

  /7

  $524,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,675 Sq Ft

  21 Westview Dr, Ashford, CT 06278

  To be built similar. Quality built and energy efficient, this 3 bedroom, 2.5 bath Custom Raised Ranch style home with 2 car garage will be built on private 1.47 acre lot. Part of the Ashford Lake Association community, you'll have lake views and access right down the street. This custom built home features high quality amenities and energy efficient construction. The main level has cathedral

  Kathleen Holland KW Legacy Partners

  21 Westview Dr, Ashford, CT 06278
• 

  

  /40

  $649,900

  • 3 Beds
  • 2.5 Baths
  • 2,604 Sq Ft

  63 May Brook, Woodstock, CT 06281

  First time offered, original owner & WBA built 2,600 sq. ft. Ranch located in a desired area of Woodstock. This home features 3 bedrooms, 2.5 bathrooms, first floor laundry, designated office space, 2 car oversized garage, along with a finished walk-up second floor bonus room over the garage. The kitchen has plenty of working space, granite counters, along with an eating space overlooking the

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  63 May Brook, Woodstock, CT 06281
• 

  

  /19

  $380,000

  • 3 Beds
  • 3 Baths
  • 1,922 Sq Ft

  3 Woodstock Ave W, Putnam, CT 06260

  Set in a peaceful setting, this charming property offers a comfortable and flexible layout designed for modern living. The updated kitchen features warm wood cabinetry, butcher block countertops, stainless steel appliances, and generous workspace, making it well suited for both everyday living and entertaining. Natural light flows throughout the home, creating a bright and welcoming atmosphere.

  Devin LeRoy The Hive Real Estate LLC

  3 Woodstock Ave W, Putnam, CT 06260
• 

  

  /19

  $265,000

  • 3 Beds
  • 1 Bath
  • 994 Sq Ft

  80 Old Plains Rd, Willimantic, CT 06226

  Three Bedroom single level ranch for sale in desirable part of Windham. Home being sold as-is, where-is. See the upside potential, see the resale value and/or rental value, and make your offer. Come see the tranquil neighborhood and nearby area, and fully enjoy. Investors, and those seeking a home that is not over-priced; come make this yours.

  Justin Marino Marino Realty LLC

  80 Old Plains Rd, Willimantic, CT 06226
• 

  

  /40

  $1,000,000 Open House 4/11

  • 3 Beds
  • 3.5 Baths
  • 4,165 Sq Ft

  187 Chaplin Rd, Eastford, CT 06242

  Welcome to this custom log home set on 3.5 secluded acres, offering lodge-style elegance, a private pond, and a separate cottage with rental income or in-law potential, all surrounded by a peaceful wooded backdrop. Spanning, 4,170 sq ft across three finished levels showcasing natural wood floors and an open main living area highlighted by a massive stone fireplace, creating a warm and inviting

  Lauren Heidelberger Berkshire Hathaway NE Prop.

  187 Chaplin Rd, Eastford, CT 06242
• 

  

  /23

  $330,000

  • 3 Beds
  • 2 Baths
  • 1,008 Sq Ft

  75 Academy Hill Rd, Plainfield, CT 06374

  This well maintained ranch offers 3 bedrooms and 1 bathroom. Features include freshly painted interior, brand new hot water tank and all new kitchen appliances. Situated on just over half an acre of mostly level land, surrounded by trees for added privacy. There's a door off the kitchen that leads to a spacious deck overlooking the yard. Storage shed included. Conveniently located near local

  Brianna Bienkiewicz Century 21 Guardian Realty

  75 Academy Hill Rd, Plainfield, CT 06374
• 

  

  /40

  $2,500,000

  • 5 Beds
  • 5.5 Baths
  • 7,772 Sq Ft

  357 Wrights Crossing Rd, Pomfret Center, CT 06259

  Reimagined in the early 1900s and surrounded by natural beauty, this extraordinary 41-acre estate offers unmatched privacy, timeless architecture, and refined craftsmanship. The 7,772 sq ft stone residence, crowned with a slate roof, is framed by rolling fields, mature trees, and manicured gardens. Inside, hand-carved moldings, elegant fireplaces, and artisan details reflect a level of quality

  Kristen Kaskela Berkshire Hathaway NE Prop.

  357 Wrights Crossing Rd, Pomfret Center, CT 06259
• 

  

  /16

  $425,000

  • 11 Beds
  • 1.5 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
• 

  

  /29

  $279,000

  • 1 Bed
  • 1 Bath
  • 704 Sq Ft

  455 Brayman Hollow Rd, Pomfret Center, CT 06259

  Introducing 455 Brayman Hollow Road, an idyllic remodeled country cottage quietly set along a country road in beautiful Pomfret, Connecticut. Nicely sited with views of nature and a backdrop of woods, this property offers a true sense of retreat while remaining accessible to local amenities and nearby highways. The home has been completely updated, including roof, windows, and siding, creating a

  Joy Riley Westcott Properties

  455 Brayman Hollow Rd, Pomfret Center, CT 06259
• 

  

  /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

  11 Woodland Dr, Windham, CT 06280

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