Windham County CT Homes for Sale

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  /20

  $619,900

  • 4 Beds
  • 3 Baths
  • 2,371 Sq Ft

  380 Mashentuck Rd, Killingly, CT 06239

  Beautiful and bright raised ranch in Killingly built in 2019, offering 4 bedrooms and 3 full baths on 6.5 private acres with potential to subdivide. The open concept layout is great for entertaining, featuring a stunning kitchen with Corian countertops, waterfall island, stainless steel appliances, cathedral ceilings, recessed lighting, and a large picture window overlooking the deck and

  Steven Koleno BEYCOME OF FLORIDA LLC

  380 Mashentuck Rd, Killingly, CT 06239
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  /38

  $450,000 Open Sat 1PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 2,847 Sq Ft

  83 Kate Downing Rd, Plainfield, CT 06374

  Welcome to this spacious and inviting contemporary offering 3 bedrooms, 2.5 baths, and a 2-car attached garage with extra storage. Filled with natural light, the main level features a dramatic living room with cathedral ceilings and skylights, a warm hardwood family room, and a formal dining room ready for everyday meals or special gatherings. The eat-in kitchen offers generous cabinet space,

  Kara Mazzola First Choice Realty

  83 Kate Downing Rd, Plainfield, CT 06374
• 

  

  

  /23

  $299,900 Open Sat 11AM - 1PM

  • 2 Beds
  • 1 Bath
  • 888 Sq Ft

  56 Myers St, Putnam, CT 06260

  This move-in ready Ranch awaits new owners to fall in love with all it has to offer! Upon entering you will be greeted by the inviting and spacious living room which is filled w/ tons of natural light, gleaming hardwood floors & flows into the dining area which is adjacent to the cabinet packed kitchen featuring plenty countertop space! Off the kitchen is a breezeway with direct access to the

  Andrew Bruce Lamacchia Realty

  56 Myers St, Putnam, CT 06260
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  /15

  $269,000

  • 5 Beds
  • 1.5 Baths
  • 2,340 Sq Ft

  1008 Windham Rd, South Windham, CT 06266

  Spacious home offering five bedrooms on the upper level along with a versatile main-level room ideal for a home office or playroom, conveniently located to the side of the home. The property features a full bathroom on the main level and a half bathroom on the second floor. Showcasing a unique layout, the home offers convenient entrances from both the upper and lower levels of the paved driveway.

  Michelle Gutierrez Social & Co Realty

  1008 Windham Rd, South Windham, CT 06266
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  /4

  $500,000 New Construction

  • 4 Beds
  • 3 Baths
  • 1,795 Sq Ft

  101 Reilly Rd, Hampton, CT 06247

  2026 BEAUTIFUL Raised ranch NEARING COMPLETION! *** (3 HOMES to CHOOSE FROM!)*** Brand new Stainless appliances in kitchen w/ white shaker cabinets, granite and island. Vaulted ceiling open floor plan great for entertaining. Living room and dining area has slider to deck to enjoy your Fall evenings. Primary bedroom with its own bathroom, walkin closet next to 2 additional bedrooms and full

  Christine Johnson RE/MAX One

  101 Reilly Rd, Hampton, CT 06247
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  /16

  $450,000

  • 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
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  /19

  $264,900

  • 3 Beds
  • 1.5 Baths
  • 1,429 Sq Ft

  34 Pleasant St Unit 8, Plainfield, CT 06374

  You can own this 3 bed home with NO money down and gain a pool for a little more than your monthly rent at $2181 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 8, Plainfield, CT 06374
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  /24

  $229,900

  • 2 Beds
  • 1 Bath
  • 1,343 Sq Ft

  34 Pleasant St Unit 5, Plainfield, CT 06374

  You can own this home with NO money down for only $2,032 a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 5, Plainfield, CT 06374
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  /25

  $369,900 Open Sat 11AM - 12:30PM

  • 2 Beds
  • 2 Baths
  • 1,500 Sq Ft

  123 Ashford Rd Unit 1, Eastford, CT 06242

  Step into effortless modern living with this beautifully appointed 2-bedroom, 2-bath condo offering 1,500sqft of bright, open space. Built in 2019, this home blends contemporary style with everyday comfort, featuring rich hardwood floors, crisp finishes, and an inviting layout. The spacious kitchen is the heart of the home, complete with sleek cabinetry, stainless steel appliances, generous

  Benjamin Carbone Lamacchia Realty

  123 Ashford Rd Unit 1, Eastford, CT 06242
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  /22

  $67,900 Coming Soon

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

  16 Pond Way, North Windham, CT 06256

  Welcome home to your spacious 2 bedroom, 2 full bathroom open floor plan at 16 Pond Way, North Windham (Stonegate Manor). First floor laundry, mudroom with backyard access, and 1,218 sqft (rarely found at this affordable price point). This home is perfect for first-time buyers, downsizers, and value-seekers looking for affordable homeownership in a convenient commuter location. Live in a quiet

  

  Stephen Daly

  KW Legacy Partners

  (860) 864-5536

  16 Pond Way, North Windham, CT 06256
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  /27

  $285,900 Open Sat 12PM - 2PM

  • 5 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  139 South St, Willimantic, CT 06226

  Enjoy the best of both worlds - homeownership with built-in rental income potential. The main residence offers 4 bedrooms, 1 full bath, and 1 half bath, providing generous space and flexibility. The first floor features a spacious eat-in kitchen, a formal dining room with a cozy pellet stove, and a large living room - both with hardwood floors. A convenient half bath completes the main level.

  Heather Miller RE/MAX One

  139 South St, Willimantic, CT 06226
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  /20

  $265,000

  • 3 Beds
  • 2 Baths
  • 1,340 Sq Ft

  263 Christian Hill Rd, Brooklyn, CT 06234

  Contractors take notice!! 1300 square foot Ranch style home solid bones and endless potential. Perfect for renovators or buyers looking to build sweat equity. Functional floor plan with great natural light. Master bedroom suite with 3/4 private bath with skylight. Large backyard with room to create your dream outdoor space.

  Kathy Rickey Signature Properties of NewEng

  263 Christian Hill Rd, Brooklyn, CT 06234
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  /2

  $379,900 Coming Soon

  • 5 Beds
  • 3 Baths
  • 1,887 Sq Ft

  203 School St, Putnam, CT 06260

  Well-maintained 3-family property in the heart of Putnam, conveniently located close to shopping, dining, schools, and major amenities. The interior has been recently renovated, offering updated finishes and move-in-ready condition. Two units are currently rented, providing immediate income, -an ideal setup for an owner-occupant or value-add investor. With strong rental potential, the existing

  Mike Zompa RE/MAX Preferred

  203 School St, Putnam, CT 06260
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  /19

  $315,000

  • 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
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  /40

  $549,900 Open Sat 2PM - 3PM

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

  13 Bates Rd, Chaplin, CT 06235

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

  Kristen Merrill Countryside Realty

  13 Bates Rd, Chaplin, CT 06235
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  /9

  $659,900 Coming Soon

  • 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
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  /36

  $517,900

  • 3 Beds
  • 2 Baths
  • 1,792 Sq Ft

  724 Cook Hill Rd, Danielson, CT 06239

  Well maintained 3 bedroom, 2 bath Contemporary ranch offering abundant natural light, an open layout, and thoughtful updates throughout. A paved driveway and stamped concrete walkway lead to the welcoming farmer's porch, perfect for relaxing outdoors. Inside, the open floor plan is ideal for entertaining, featuring a spacious carpeted living room with electric fireplace, ceiling fans, and sun

  Kara Mazzola First Choice Realty

  724 Cook Hill Rd, Danielson, CT 06239
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  /17

  $299,000

  • 2 Beds
  • 1 Bath
  • 1,144 Sq Ft

  94 Hartford Rd, Brooklyn, CT 06234

  Charming Ranch on Spacious Lot - Peaceful Setting with Big Potential! Welcome to 94 Hartford Rd, a delightful ranch-style home nestled on 0.84 acres in desirable Brooklyn, CT. This charming residence features a classic layout with 2 bedrooms and 1 full bath, offering comfortable single-level living with tons of character. Hardwood floors add warmth and character throughout the main level. A

  Mickey Morabito RE/MAX Bell Park Realty

  94 Hartford Rd, Brooklyn, CT 06234
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  /22

  $315,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  9 Highland View Dr, South Windham, CT 06266

  Perfect first home, or downsize, with the big updates already done. This move-in ready property offers peace of mind for first-time buyers looking to avoid costly repairs and enjoy homeownership from day one. Three Bedrooms, open layout, pellet stove, garage with attic storage, an open breezeway, and Hard Wood Floors! Off street parking, Paved driveway. Recent improvements include a brand-new

  Brian Connolly Real Broker CT, LLC

  9 Highland View Dr, South Windham, CT 06266
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  /18

  $424,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,666 Sq Ft

  69 Sunset Hill Rd, Thompson, CT 06277

  Set atop a gentle rolling hill and surrounded by 3 acres of peaceful, private land, this genuine Cape Cod-style home blends timeless New England charm with thoughtful updates and lots of natural light. Cedar shingles, recently professionally washed, give the exterior a classic look, while the attached one car garage adds everyday convenience. Step inside to a spacious front-to-back living room,

  Elizabeth Forand Berkshire Hathaway NE Prop.

  69 Sunset Hill Rd, Thompson, CT 06277
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  /29

  $369,000

  • 4 Beds
  • 2 Baths
  • 2,154 Sq Ft

  25 Seward St, Putnam, CT 06260

  Historic craftsmanship meets modern comfort. Imagine yourself on the classic front porch, a place made for slow-drifting summer afternoons and rocking chairs before you step into a world of timeless elegance inside this stunning Victorian home. As you enter, you are immediately greeted by soaring high ceilings and the warm glow of original hardwood floors that flow throughout the residence. The

  Renee McCammon Berkshire Hathaway NE Prop.

  25 Seward St, Putnam, CT 06260
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  /34

  $159,000

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  16 Circle Dr, North Windham, CT 06256

  Welcome to this beautifully updated and impeccably maintained double-wide home offering 1,620 square feet of modern, comfortable living. With about $35,000 in thoughtful upgrades since purchase, this home is truly move-in ready and designed for both style and convenience. Step inside to a spacious, open layout that feels airy, welcoming, and immaculate throughout. The updated kitchen features

  Danielle Fortier Coldwell Banker Realty

  16 Circle Dr, North Windham, CT 06256
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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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  /39

  $349,000

  • 2 Beds
  • 1.5 Baths
  • 1,584 Sq Ft

  204 Brookes Landing Unit 204, Killingly, CT 06239

  Beautifully maintained and move-in ready condo offering the perfect blend of comfort and style! Gleaming hardwood floors create a warm and inviting atmosphere, while the spacious bedrooms provide comfort and flexibility. The partially finished lower-level rec room adds valuable additional space and is ideal for entertaining! The seller is including the pool table, shuffleboard table, and dart

  Scott Pempek Berkshire Hathaway NE Prop.

  204 Brookes Landing Unit 204, Killingly, CT 06239
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  /28

  $329,900 Open Sat 10AM - 12PM

  • 2 Beds
  • 2.5 Baths
  • 1,530 Sq Ft

  3 Fairways Cir, Woodstock, CT 06281

  Welcome to your perfect blend of comfort, convenience, and resort-style living! This beautifully maintained 2 bedtoom, 2 bath condo is nestled directly on the fairway, offering peaceful golf-course views and a lifestyle that feels like a getaway every day. The primary suite offers a generous bedroom with ample closet space. The second bedroom is ideal for guest as is includes its own bathroom.

  Nicole Cournoyer RE/MAX Bell Park Realty

  3 Fairways Cir, Woodstock, CT 06281
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  /18

  $209,900

  • 2 Beds
  • 1 Bath
  • 1,215 Sq Ft

  34 Pleasant St Unit 6, Plainfield, CT 06374

  You can own this home with NO money down for less than what you pay in rent a month....all taxes, insurance and HOA fees included. Take advantage of a program that has limited funding left! Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 6, Plainfield, CT 06374
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  /25

  $264,900

  • 3 Beds
  • 1 Bath
  • 1,314 Sq Ft

  34 Pleasant St Unit 4, Plainfield, CT 06374

  You can own this 3 bed home with NO money down and gain a pool for a little more than your monthly rent at nearly $2234 a month....all taxes, insurance and HOA fees included. Rather than paying someone else's mortgage pay yourself!

  Benjamin Carbone Lamacchia Realty

  34 Pleasant St Unit 4, Plainfield, CT 06374
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  /40

  $439,900 Open Sat 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  5 Insalaco Dr, Windham, CT 06280

  Welcome to 5 Insalaco Drive in Windham - a stunning, meticulously maintained 4-bedroom, 2-bath ranch style home located in a desirable countryside neighborhood, just minutes from Windham Center, Windham Shetucket Pickleball Park, Windham Fish & Game Club, and Mansfield Hollow State Park. This move-in ready home features hardwood floors throughout, large bedrooms with ample closet space, and an

  Joseph Snell Luxe Realty LLC

  5 Insalaco Dr, Windham, CT 06280
• 

  

  /40

  $399,999 Open Sat 1PM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,912 Sq Ft

  184 Black Hill Rd, Plainfield, CT 06374

  Welcome to 184 Black Hill Road in Plainfield - a spacious 4-bedroom, 2.5-bath home offering 2,912 square feet of comfortable living space set on 1.58 private acres. Step inside to discover a beautifully updated living room, creating a fresh and inviting space perfect for relaxing or entertaining. The generous layout offers room to spread out, with well-sized bedrooms and multiple living areas

  Dennisse Rivera Kempf-Vanderburgh Realty

  184 Black Hill Rd, Plainfield, CT 06374
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  /20

  $385,000

  • 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
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  /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
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  /24

  $319,900

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

  29 Bellevue St, Putnam, CT 06260

  Great opportunity for a perfect owner occupied 2 family located on a dead-end street in Putnam. This multi-family home features a newer roof (2023), two new heating systems (2023), rebuilt decks/porches, updated oil tanks along with modern electrical. The rented first floor is nicely updated featuring 2 bedrooms, 1 large modern full bathroom, hardwood floors throughout the living & bedroom areas,

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  29 Bellevue St, Putnam, CT 06260
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  /26

  $589,000 New Construction

  • 3 Beds
  • 2 Baths
  • 1,620 Sq Ft

  76 Wauregan Rd, Canterbury, CT 06331

  Welcome to this beautifully crafted new construction ranch offering 1,620 square feet of thoughtfully designed living space. This 3-bedroom, 2-bath home features a bright open-concept layout perfect for modern living and entertaining. Rich red oak flooring flows throughout the main living areas, complemented by high-end granite countertops that add elegance and durability to the kitchen. Set on a

  Alicia Cournoyer Kazantzis Real Estate, LLC

  76 Wauregan Rd, Canterbury, CT 06331
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  /40

  $429,900

  • 3 Beds
  • 2 Baths
  • 1,910 Sq Ft

  470 Fabyan Rd, North Grosvenordale, CT 06255

  Set in the woods, this young Cape style home features 1,900+ sq. ft., 3 bedrooms, 2 bathrooms, a 2-car garage plus shed & detached workshop garage all on over 4 AC. Entering the home you will find a convenient first floor full bathroom before entering the spacious & open living/dining room. A good-sized living room off the dining space features a wood burning fireplace. The sunroom is heated &

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  470 Fabyan Rd, North Grosvenordale, CT 06255
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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 with a roof updated in 2023. The front porch invites tranquil mornings surrounded by nature,

  Lisa Weagle Kazantzis Real Estate, LLC

  70 Crandall Ln, Canterbury, CT 06331
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  /2

  $98,000

  • Land
  • 2.8 Acres
  • $35,000 per Acre

  70 Brayman Hollow Rd, Pomfret, CT 06259

  This 2.8 ac parcel is a beautifully wooded residential lot bordered by historic field stone walls in the front. Located on a beautiful rural road in Pomfret, CT. It has a gentle slope, fully treed. It borders the first hole at Vinyard Valley Golf Course in the rear of lot. This stunning lot, with meandering drive back to home location creates privacy, intrigue, surrounded by nature. This lot has

  Cynthia Sherman Berkshire Hathaway NE Prop.

  70 Brayman Hollow Rd, Pomfret, CT 06259
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  /31

  $325,000

  • 3 Beds
  • 1.5 Baths
  • 1,068 Sq Ft

  117 State Ave, Dayville, CT 06241

  Move-in ready and fully remodeled home-perfect for first-time buyers! This updated property features an open-concept main level with a brand-new kitchen, breakfast bar, ample storage, and a convenient half bath. Recent upgrades include new appliances, new windows, new flooring, LED lighting, and energy-efficient mini-split heating and cooling throughout, offering comfort and low utility costs.

  Brian Connolly Real Broker CT, LLC

  117 State Ave, Dayville, CT 06241
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  /29

  $299,000

  • 3 Beds
  • 1.5 Baths
  • 1,160 Sq Ft

  119 Quercus Ave, Willimantic, CT 06226

  Tucked into The Oaks, one of Willimantic's most beloved neighborhoods, this 1890s Cape Cod is a home that feels instantly welcoming. Built by the Willimantic Linen Company, it reflects a simpler time, beginning with a covered front porch and a thoughtfully scaled interior that feels comfortable and inviting. The 1,160 square foot home offers three bedrooms and a cozy living room featuring the

  Kristen Kaskela Berkshire Hathaway NE Prop.

  119 Quercus Ave, Willimantic, CT 06226
• 

  

  /30

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,134 Sq Ft

  941 Upper Maple St, Dayville, CT 06241

  Move right into this spacious one-level ranch set on nearly an acre of land. Enjoy the convenience of nearby highways and shopping while still savoring a bit of a peaceful, rural feel. The home features high-end durable plank vinyl flooring and custom window treatments throughout, with all living spaces, including the laundry, conveniently located on the main level! Closet and storage space

  Kristen Moore RE/MAX Properties

  941 Upper Maple St, Dayville, CT 06241
• 

  

  /16

  $369,900

  • 3 Beds
  • 1.5 Baths
  • 1,056 Sq Ft

  33 Junior Ave, Danielson, CT 06239

  Welcome to 33 Junior Ave - a perfectly scaled ranch offering one-level comfort and classic charm. This well-maintained home features three bedrooms and two bathrooms. Hardwood floors flow throughout an open living room and refreshed, eat in kitchen, with sliding glass doors leading to the patio and backyard. The attached garage and level lot add convenience and outdoor space for entertaining or

  Amy Brunet Brunet and Company Real Estate

  33 Junior Ave, Danielson, CT 06239

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