Windham County CT Houses for Sale

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  /12

  $299,900

  • 3 Beds
  • 1.5 Baths
  • 1,575 Sq Ft

  485 Hampton Rd, Pomfret Center, CT 06259

  New England Charmer in Historic Pomfret Center Step into this colonial-style antique, featuring timeless ship lap siding and an oversized barn. This 3-bedroom, 1.5-bath home offers wonderful curb appeal with its original white picket fence and rocking-chair-ready farmer's porch. Inside, you'll find an inviting eat-in kitchen with custom cubby storage, reminiscent of Pottery Barn style.

  Madison Litalien Berkshire Hathaway NE Prop.

  485 Hampton Rd, Pomfret Center, CT 06259
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  /11

  $324,900

  • 4 Beds
  • 2 Baths
  • 2,128 Sq Ft

  140 Federal Rd, Chaplin, CT 06235

  Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $3,249 back in closing costs credits OR $1,921 per month at an exceptional financing rate of 5.87% APR with ZERO down payment available for those who qualify. Your Private Oasis Awaits Beautiful home in a highly sought-after location! Featuring a stunning granite

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

  140 Federal Rd, Chaplin, CT 06235
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  /36

  $799,000

  • 4 Beds
  • 2.5 Baths
  • 3,222 Sq Ft

  115 Babbitt Hill Rd, Pomfret Center, CT 06259

  This beautiful 3222 sq. ft. Colonial offers everything you could want and more, set on a beautifully manicured lot in a quiet and desirable location. Inside you'll find a spacious layout with 4 bedrooms, 2.5 baths, hardwood floors o the main level, and central air throughout. The inviting living room features a cozy fireplace, while the large kitchen is a true chef's dream with abundant

  Pat Malek First Choice Realty

  115 Babbitt Hill Rd, Pomfret Center, CT 06259
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  /36

  $369,900

  • 2 Beds
  • 1 Bath
  • 440 Sq Ft

  17 Green Island, Thompson, CT 06277

  Discover the charm of island living at Quaddick Lake! Seize this RARE opportunity to own a lakeside retreat on a private island dotted with just 12 seasonal cottages. Set just off the lake shore, this enchanting getaway offers the best of both worlds--unforgettable sunrise and sunset views, plus TWO waterfront areas providing 200 ft. of direct lake access on both sides of the island. The fully

  Lynne Ferrigno Coldwell Banker Realty

  17 Green Island, Thompson, CT 06277
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  /27

  $875,000

  • 3 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  28 Lake View Dr, Woodstock, CT 06281

  The Lake Home That Truly Has It All. This is more than just a charming waterfront- it's the home that checks every box! Set on beautiful Lake Bunggee, this year-round 3-bedroom retreat pairs panoramic water views with irresistible curb appeal and a storybook sense of charm in one of the lake's most desirable locations. Cathedral ceilings flood the home with natural light, while the gourmet

  Jennie Kesselman Berkshire Hathaway NE Prop.

  28 Lake View Dr, Woodstock, CT 06281
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  /22

  $214,000

  • 3 Beds
  • 1 Bath
  • 1,367 Sq Ft

  24 Tatem St, Putnam, CT 06260

  Welcome to this inviting 3-bedroom home with the potential for a 4th bedroom, offering flexibility for a growing household, guest room, or home office. With 1.5 bathrooms and set on a 0.18-acre lot, this property combines comfort, functionality, and convenience. Located in the heart of Putnam, CT, you'll enjoy the charm of a small-town community while being close to schools, shopping, dining, and

  Patrick Precourt Dorrance Realty

  24 Tatem St, Putnam, CT 06260
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  /40

  $1,100,000

  • 5 Beds
  • 3 Baths
  • 2,771 Sq Ft

  498 Bailey Hill Rd, Dayville, CT 06241

  WELCOME TO THE YELLOWSTONE RANCH...IMPRESSIVE 25+ACRES OF CAPTIVATING COUNTRYSIDE RETREAT NESTLED IN THE QUIET CORNER OF KILLINGLY. WONDERFUL EQUINE PROPERTY OR UNIQUE OPPORTUNITY FOR COMPLETE PRIVACY WITH THIS RECENTLY BUILT CUSTOM 5 BEDROOM RANCH PRESENTING A MINIMALISTIC INTERIOR DESIGN APPROACH FEATURING CLEAN LINES WITH BRIGHT OPEN FLOWING FLOOR PLAN STAINLESS KITCHEN, FARMHOUSE SINK AND 3

  BJ Lee William Raveis Real Estate

  498 Bailey Hill Rd, Dayville, CT 06241
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  /40

  $614,900

  • 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
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  /22

  $354,900 Open Sun 2:30PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,112 Sq Ft

  415 Maple St, Danielson, CT 06239

  Welcome to this beautifully updated 4-5 bedroom Colonial set on a desirable corner lot in the heart of Killingly, CT. This property is a combination of modern updates and spacious layouts. Step inside to find newly finished hardwood floors throughout, an open and inviting layout, and plenty of natural light. Both the kitchen and bathrooms have been tastefully designed. Enjoy year-round comfort

  Benjamin Carbone Lamacchia Realty

  415 Maple St, Danielson, CT 06239
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  /40

  $339,900

  • 4 Beds
  • 2 Baths
  • 1,594 Sq Ft

  331 Pond Hill Rd, Moosup, CT 06354

  Welcome home to this sunny ranch with year-round water views of Moosup Pond! The main level features an eat-in kitchen opening to a bright and generously sized living room. Built-ins flank the fireplace and a bay window frames the view. Down the hall are three comfortable bedrooms and a full bath. Need space for extended family or guests? The walkout lower level offers a true in-law/auxiliary

  Rob Perillo Robert A. Perillo Jr

  331 Pond Hill Rd, Moosup, CT 06354
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  /20

  $159,200

  • 3 Beds
  • 2 Baths
  • 1,456 Sq Ft

  416 Hanover Rd, Baltic, CT 06330

  Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our APPRAISAL describe the property as a SFR (RANCH) built in 1957. It has a GLA of approx. 1456 and has 3 bedrooms and

  Christopher Rose Realhome Services & Solutions

  416 Hanover Rd, Baltic, CT 06330
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  /13

  $338,000

  • 3 Beds
  • 1 Bath
  • 953 Sq Ft

  10 Charlotte St, Danielson, CT 06239

  Welcome to this beautifully maintained 3-bedroom, 2-bathroom raised ranch that blends comfort, style, and functionality. Located in a desirable neighborhood, this home offers a bright and inviting layout perfect for everyday living and entertaining. Inside, you'll find new flooring throughout and an updated kitchen complete with modern appliances, sleek cabinetry, and plenty of counter space for

  Ashley Walker Brunet and Company Real Estate

  10 Charlotte St, Danielson, CT 06239
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  /37

  $1,700,000

  • 7 Beds
  • 5 Baths
  • 4,283 Sq Ft

  90-94 & 93 Upton Rd, Ashford, CT 06278

  Welcome to one of the most extraordinary and locally adored estates in Eastern Connecticut-nearly 300 acres of rolling fields, woodlands, and historic charm offered as a single, unmatched property. Privately set along a quiet, town-maintained dirt road, this expansive estate combines 93 and 90-94 Upton Road into a rare opportunity for legacy ownership. The centerpiece is a breathtaking

  Nicole Gleason CR Premier Properties

  90-94 & 93 Upton Rd, Ashford, CT 06278
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  /38

  $574,900

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

  58 New Rd, Moosup, CT 06354

  Set on scenic acreage, this inviting single-level ranch offers a seamless blend of comfort and natural beauty. Relax on the wide front porch or entertain on the expansive back deck while enjoying visits from local wildlife. Inside, the thoughtfully designed open floor plan is warmed by a wood-burning fireplace and brightened by large windows overlooking the yard. The kitchen pairs charm with

  Heather Morrone Coldwell Banker Coastal Homes

  58 New Rd, Moosup, CT 06354
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  /40

  $2,500,000

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

  357 Wrights Crossing Rd, Pomfret Center, CT 06259

  Steeped in history and surrounded by natural beauty, this extraordinary 41-acre estate offers unmatched privacy, timeless architecture, and refined craftsmanship. Originally built in the mid-1800s and reimagined in 1906, the 7,000+ sq ft stone residence is crowned with a slate roof and framed by lush fields and gardens. Inside, hand-carved moldings, elegant fireplaces, and artisan details speak

  Kristen Kaskela Berkshire Hathaway NE Prop.

  357 Wrights Crossing Rd, Pomfret Center, CT 06259
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  /24

  $335,000

  • 3 Beds
  • 1.5 Baths
  • 1,760 Sq Ft

  26 Perkins St, Plainfield, CT 06374

  Rare Sprawling colonial set on a corner lot with 5 Bedrooms 3 Baths with plenty of nooks and crannies for entertainment and comfort for the entire family. The first floor features large entry foyer with sitting room, sizeable primary bedroom with full bath, eat in kitchen, dining room, and an additional bedroom and full bath. The upper floor has 3 additional roomy bedrooms. Lots of storage space

  Victoria Lindsey Coldwell Banker Realty

  26 Perkins St, Plainfield, CT 06374
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  /22

  $289,900

  • 3 Beds
  • 1.5 Baths
  • 2,236 Sq Ft

  360 N Society Rd, Canterbury, CT 06331

  EXCEPTIONAL NEW PRICE!!! on this opportunity to renovate your own dream home to YOUR liking! A great opportunity to build GREAT EQUITY and be located in beautiful Canterbury, with choices of school, options for animals and gardens! This large house is currently mostly gutted and waiting for you to complete. 2 car garage attached to the house, and oversized 2 car garage workshop great for home

  Michelle Pivin Kazantzis Real Estate, LLC

  360 N Society Rd, Canterbury, CT 06331
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  /34

  $549,900

  • 3 Beds
  • 1.5 Baths
  • 2,997 Sq Ft

  160 Halls Hill Rd, Killingly, CT 06239

  History lovers take notice! Previously the South Killingly Congregational Church, this authentic 1837 Greek Revival has been completely restored and converted into a home with endless possibilities for the main space. Let your imagination soar in deciding how you will use the great room! Currently setup as a living/dining/entertainment space, complete with an 85" TV, this space (approx 30X40 with

  Sandra Sokoloff RE/MAX One

  160 Halls Hill Rd, Killingly, CT 06239
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  /12

  $54,000

  • 2 Beds
  • 1 Bath
  • 728 Sq Ft

  6 Kitty Ln, Windham, CT 06256

  Price Improved Welcome home to this cozy and affordable 2 bedroom mobile home on a perfect level lot. Whether you're starting out or downsizing, this home is move-in ready and full of possibilities. Enjoy quiet living while still being close to shopping dining and more! This home won't last. Make an appointment to see for yourself! As Is.

  Karen Wheeler Regency Real Estate, LLC

  6 Kitty Ln, Windham, CT 06256
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  /39

  $269,900

  • 4 Beds
  • 2 Baths
  • 2,275 Sq Ft

  209 Church St, Willimantic, CT 06226

  Now at an improved price! Come tour this wonderful and iconic Victorian home, nearly all interior woodwork has been preserved in its original, natural wood state. About the build date, the town records show 1879, but per the Willimantic Victorian Neighborhood Association, this home was built in 1888. This home is spacious, has replacement windows and a newer boiler and hot water heater, On the

  Rick Nassiff KW Legacy Partners

  209 Church St, Willimantic, CT 06226
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  /33

  $249,000

  • 3 Beds
  • 1 Bath
  • 1,076 Sq Ft

  222 Southridge Dr, Willimantic, CT 06226

  Welcome to 222 Southridge Drive, a spacious and inviting 3-bedroom, 1-bath ranch-style home offering comfortable, easy living with thoughtful cosmetic updates throughout. Step inside to find a bright and inviting living space featuring freshly painted walls, updated flooring, and plenty of natural light. The kitchen offers ample cabinet space and a functional layout perfect for everyday living

  Taylor Gildein Re/Max Results

  222 Southridge Dr, Willimantic, CT 06226
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  /26

  $374,900

  • 3 Beds
  • 1.5 Baths
  • 1,528 Sq Ft

  68 Allen Hill Rd, Brooklyn, CT 06234

  This beautifully renovated home offers the perfect blend of modern upgrades and timeless charm. Step inside to find a brand-new kitchen featuring sleek granite countertops, stainless steel appliances, and custom cabinetry that provides both style and functionality. The warm glow of refinished hardwood floors flows throughout the main living areas, anchored by a stunning stone fireplace that adds

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  68 Allen Hill Rd, Brooklyn, CT 06234
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  /40

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,537 Sq Ft

  246 Heritage Rd, Putnam, CT 06260

  Welcome to 246 Heritage Road in Putnam, CT. This beautifully maintained 2,537 square foot antique colonial home seamlessly blends historic charm with modern updates. Featuring 3 bedrooms and 2 full baths, this home invites you to take a step back in time while enjoying today's comforts. Inside, you will find warm, inviting spaces ideal for both relaxing and entertaining. Step outside to your

  Charolotte Cook CR Premier Properties

  246 Heritage Rd, Putnam, CT 06260
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  /40

  $275,900

  • 2 Beds
  • 2 Baths
  • 804 Sq Ft

  188 Oxbow Dr, Willimantic, CT 06226

  This spacious Raised Ranch features a large kitchen with a center island and ample cabinetry, seamlessly connected to an open-concept living area-perfect for entertaining. The main level offers two comfortable bedrooms and a full bathroom. Downstairs, the finished lower level includes a second full bath and flexible space ideal for a home office, playroom, game room, or potential third bedroom.

  Peter Baker RE/MAX Bell Park Realty

  188 Oxbow Dr, Willimantic, CT 06226
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  /14

  $199,999

  • 2 Beds
  • 2 Baths
  • 2,713 Sq Ft

  211 Old Colony Rd, Eastford, CT 06242

  This unique property in Eastford, CT, built in 1821, offers over 2700 square feet of living space and is brimming with historical charm and potential. While it requires extensive renovation to restore its former glory, the home boasts original features such as wide-plank hardwood floors and built ins. The spacious layout includes multiple rooms that can be reimagined for modern living. This

  Brittany Russell Tier 1 Real Estate

  211 Old Colony Rd, Eastford, CT 06242
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  /40

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,392 Sq Ft

  316 Westminster Rd, Canterbury, CT 06331

  Brand new septic system just installed! Welcome to your own private paradise! Discover this beautifully renovated 3-bedroom ranch home in the peaceful town of Canterbury CT. Situated on a private, secluded lot, surrounded by lush perennial landscaping, this property offers both comfort and privacy. The spacious living room features a stunning fireplace perfect for cozy nights. The remodeled

  Brenda Chubbuck CR Premier Properties

  316 Westminster Rd, Canterbury, CT 06331
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  /32

  $290,000

  • 2 Beds
  • 1 Bath
  • 1,040 Sq Ft

  242 Herrick Rd, Brooklyn, CT 06234

  1.93 acres of pure retreat await you! Follow the country roads to this charming 2-bedroom split-style home on an incredible lot. Private, yet accessible to all of the downtown conveniences you need. Lush fruit trees & bushes surround this outdoor oasis, with endless options for gardening! Double fire pits, gazebos of greenery - a must see. Many recent updates - priced to sell & ready for your

  Jackie Tacy RE/MAX One

  242 Herrick Rd, Brooklyn, CT 06234
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  /39

  $524,900

  • 3 Beds
  • 2 Baths
  • 2,036 Sq Ft

  36 Dunleavy Dr, Woodstock, CT 06281

  Discover this charming colonial Lakefront home on Roseland Lake, offering 2,036 sq ft of lovely updated living space. Boasting 3 to 4 bedrooms and 2 full baths, this residence combines classic elegance with modern comforts. The home features a spacious 2 1/2 car garage, an oversized shed for ample storage, and was renovated and expanded in 2017, ensuring contemporary finishes and functional

  Diane White CR Premier Properties

  36 Dunleavy Dr, Woodstock, CT 06281
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  /39

  $699,000 Open Sat 11AM - 1PM

  • 5 Beds
  • 4.5 Baths
  • 3,886 Sq Ft

  68 Roode Rd, Plainfield, CT 06374

  Discover this UNIQUE 5 Bedroom, 4-1/2 Bath Gambrel Colonial nestled on 1.49 acres. NEW SEPTIC TANK Installed 2025! This 3,886 Sq Ft home offers a spacious layout including 2 Primary Bedrooms sharing an Ensuite Bath with SAUNA and Whirlpool Tub. WHEELCHAIR ACCESSIBLE design featuring an ELEVATOR/LIFT (Dumbwaiter) to reach all floors and also a LIFT from driveway to deck for easy access into the

  Mary Ann Bohonowicz Berkshire Hathaway NE Prop.

  68 Roode Rd, Plainfield, CT 06374
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  /40

  $860,000 Open Sun 10AM - 11:30AM

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

  133 Munyan Rd, Putnam, CT 06260

  Welcome to 133 Munyan Road in Putnam, Connecticut-a beautifully maintained and private retreat nestled on over 4 acres of picturesque land. This elegant 3-bedroom, 2.5-bathroom home, built in 1988, offers approximately 3,282 square feet of refined living space. Recent upgrades include a brand-new roof and an updated kitchen, blending modern comfort with timeless charm. Inside, you'll find a warm,

  Joel Grispino Drawbridge Realty

  133 Munyan Rd, Putnam, CT 06260
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  /37

  $549,900

  • 3 Beds
  • 1 Bath
  • 1,323 Sq Ft

  1 Laurel Hill Dr, Woodstock Valley, CT 06282

  Pride of ownership shines in this wonderful year-round ranch nestled in a peaceful cove on fully recreational Lake Bungee!Whether you're looking to fish,swim,kayak,ski,or ice fish this home offers four seasons of fun right from your backyard-complete with your own private dock and stunning view of the nearby waterfall! Thoughtfully updated in 2025 the entire house was given a fresh new look!

  Pat Malek First Choice Realty

  1 Laurel Hill Dr, Woodstock Valley, CT 06282
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  /40

  $715,000

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

  34 Pine Tree Terrace, Brooklyn, CT 06234

  This elegant colonial seamlessly blends classic architectural charm with thoughtful craftsmanship and character. With over 2900 sq ft, this spacious home is perfect for gatherings and entertaining guests in style. The front-to-back family room, featuring a woodburning fireplace, is warm and welcoming. The open floorplan is enhanced with pegged wide-board flooring and woodwork crafted from trees

  Bob Seele Coldwell Banker Realty

  34 Pine Tree Terrace, Brooklyn, CT 06234
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  /36

  $749,900

  • 3 Beds
  • 2.5 Baths
  • 3,364 Sq Ft

  36 Breakneck Hill Rd, Dayville, CT 06241

  Gracefully set on 7.7 private acres, this exceptional estate was designed for those who live to entertain-and love to retreat. From its elegant architecture to its resort-inspired amenities, every detail reflects luxury without compromise. Inside, soaring ceilings and refined millwork frame a layout built for both grand gatherings and quiet indulgence. The formal dining room makes a statement

  Patrick Farrell Compass Connecticut, LLC

  36 Breakneck Hill Rd, Dayville, CT 06241
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  /28

  $400,000

  • 1 Bed
  • 1 Bath
  • 517 Sq Ft

  31 Green Island, Thompson, CT 06277

  Quaddick Lake. Unique opportunity on Green Island. Only 12 homes in this private seasonal community. Home has been carefully renovated. Located on the southern peninsula of the island with 3 sides of waterfront.. over 90 feet. Spectacular views, easy access to the water, 3 docks. Large common area, one bedroom and loft. Screen porch to large deck. Home has electric, heat, ac, dry-well for shower

  Richard Loomis RE/MAX Bell Park Realty

  31 Green Island, Thompson, CT 06277
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  /34

  $599,000

  • 4 Beds
  • 3.5 Baths
  • 4,476 Sq Ft

  104 Windham Center Rd, Windham, CT 06280

  Elegant, Greek Revival Colonial home in historic Windham Center completely remodeled in 2005 by New England Design. This four bedroom, 3 full and one half bath features the charm and craftsmanship of bygone days with all of the convenience of modern day living. Three fireplaces, granite and marble flooring, graceful touches such as mahogany paneling in the study, bookcases, built ins, moldings,

  Lawrence Ross Weichert,REALTORS-Four Corners

  104 Windham Center Rd, Windham, CT 06280
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  /19

  $228,500

  • 4 Beds
  • 1 Bath
  • 1,078 Sq Ft

  129 Walnut St, Willimantic, CT 06226

  Charming antique 1915 home in down town Willimantic on a beautiful corner lot showcasing its 20th century craftsmanship. The authentic wooden white picket fence is a beautiful addition to all of the craftsmanship . A two story carriage house style garage detached from the home offering an abundance of space and access onto two roads. Conveniently just walking distance from Eastern CT State

  Lisa Therecka Therecka & Associates LLC

  129 Walnut St, Willimantic, CT 06226
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  /39

  $399,999

  • 5 Beds
  • 3 Baths
  • 2,100 Sq Ft

  22 Philmar Dr, Plainfield, CT 06374

  Need space for a growing family or in-home business? This remodeled 5-bedroom, 3-bath ranch-style home offers it all! Situated on a large, level .73-acre lot in a peaceful cul-de-sac, this property features a accessible ramp and along with one of three bathrooms. The rear facing open family room has cathedral ceiling,huge windows and skylights with access to a large deck .Combined with the

  Vito Uva Scalzo Real Estate

  22 Philmar Dr, Plainfield, CT 06374
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  /40

  $1,100,000

  • 5 Beds
  • 4 Baths
  • 5,079 Sq Ft

  76 Mill Brook Ln, Woodstock, CT 06281

  Tucked away on 6.5 private acres in the prestigious MillBrook Estates, this 5,000+ sq ft custom home offers an exceptional blend of elegance, functionality, and luxury. A long paved drive leads to this stately residence, featuring 5 bedrooms, multiple living areas, and rich architectural details throughout. The grand foyer with a hydraulic chandelier sets the tone for the craftsmanship found

  Katie Totten William Raveis Real Estate

  76 Mill Brook Ln, Woodstock, CT 06281
• 

  

  /22

  $340,000

  • 5 Beds
  • 2 Baths
  • 1,591 Sq Ft

  546 N Main St, Moosup, CT 06354

  Welcome to this beautifully updated 5-bedroom, 2-bathroom home offering a perfect blend of comfort and modern style. With 8 spacious rooms, this property features a thoughtfully renovated kitchen and bathrooms, making it move-in ready for its next owner. Situated on a private and secluded 0.14-acre lot, the home provides rare peace and privacy while still being conveniently located. Enjoy the

  Kevin Brignole Spaulding Realty Group, LLC

  546 N Main St, Moosup, CT 06354
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  /40

  $715,000

  • 5 Beds
  • 2 Baths
  • 2,443 Sq Ft

  393 N Canterbury Rd, Canterbury, CT 06331

  Price Drop and brush cleared right up to the pond! Built in 1750 and celebrating its 275th anniversary, this distinguished antique Colonial farmhouse remains a pristine exemplar of early New England architecture. Set on 8.5 acres and nestled on scenic route 169, the estate features a secluded pond, a gently winding brook, and two traditional barns-all original to its historic rural setting. This

  Adam Gumula Kazantzis Real Estate, LLC

  393 N Canterbury Rd, Canterbury, CT 06331

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