Windham County CT Homes under $500,000

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  /32

  $499,900

  • 3 Beds
  • 3 Baths
  • 2,464 Sq Ft

  31 Cherry Hill Rd, Brooklyn, CT 06234

  Welcome to this expansive and meticulously maintained raised ranch in the heart of Brooklyn, CT. This stunning home boasts an open floor plan flooded with natural light from large windows and enhanced by soaring vaulted ceilings. Gleaming hardwood floors flow throughout the main living spaces, showcasing beautiful finishes that elevate every room. Central air throughout the home brings comfort on

  

  Nathan Cholewa

  Kazantzis Real Estate, LLC

  (860) 431-3428

  31 Cherry Hill Rd, Brooklyn, CT 06234
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• 

  

  

  /32

  $449,900 Open Sun 1PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,508 Sq Ft

  72 Old Canterbury Rd, Hampton, CT 06247

  Welcome to this stunning, fully remodeled 3-bedroom, 2-bath ranch on 4 acres. Every inch of this oversized home has been updated with precision and care, showcasing the stylish and modern finishes throughout. The true highlight of the home is the expansive great room, designed for unforgettable entertaining. With abundant natural light, and an open-concept layout that flows seamlessly into the

  

  Jennifer Lehto

  Kazantzis Real Estate, LLC

  (860) 854-3966

  72 Old Canterbury Rd, Hampton, CT 06247
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  /38

  $475,000

  • 3 Beds
  • 2.5 Baths
  • 2,554 Sq Ft

  9 Pheasant Ln, Brooklyn, CT 06234

  For nearly 50 years, the same family has enjoyed this classic, elegant Dutch Colonial. Warm wood features run throughout the home, in the flooring, walls, ceilings and doors. Custom built-ins accent many of the spaces in the home. Enter the mudroom with a large closet, powder room and convenient laundry location. The family room stays bright with a skylight, and direct access to the screened in

  Lynn Converse RE/MAX Bell Park Realty

  9 Pheasant Ln, Brooklyn, CT 06234
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  /30

  $469,900 Open House 6/08

  • 3 Beds
  • 1.5 Baths
  • 2,440 Sq Ft

  23 Hell Hollow Rd, Sterling, CT 06354

  Vacation at home. Fantastic home with amazing backyard. Open dining/living room combination with breakfast bar that leads out to a Trex deck that overlooks the pool, large patio area with fire pit, and horseshoe pit. First floor laundry in updated bathroom. Walkout finished lower level has massive family room, guest room, and 1/2 bath. Solar installed 3 years ago so many years of great savings

  Alexis Devlin Coldwell Banker Realty

  23 Hell Hollow Rd, Sterling, CT 06354
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  /40

  $465,000

  • 4 Beds
  • 2.5 Baths
  • 2,146 Sq Ft

  49 Bennett Pond Rd, Canterbury, CT 06331

  The "IT" house of the season! Featured in Country Living Magazine and Country Sampler Farmhouse Style Magazine! This gorgeous well appointed Federal Architectural home, is oozing in charm, history and sophistication. Once owned by Hezekia Crandall! ( more history available). Much larger and spacious than it appears from the outside. 4 bedrooms with fireplaces. 2.5 bathroom. Formal living room,

  Skyla Gagnon RE/MAX Bell Park Realty

  49 Bennett Pond Rd, Canterbury, CT 06331
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  /39

  $475,000

  • 3 Beds
  • 2 Baths
  • 1,728 Sq Ft

  1026 Route 171, Woodstock, CT 06281

  Stunning 3-bedroom, 2-bath Colonial in picturesque Woodstock, CT, situated on 2 serene acres. This home has undergone a complete renovation with approximately $150,000 in high-end upgrades, blending modern luxury with classic New England charm. Step inside to discover a brand-new kitchen featuring top-of-the-line appliances, sleek cabinetry, and elegant countertops. Gleaming new floors flow

  Daniel Deojay RE/MAX Bell Park Realty

  1026 Route 171, Woodstock, CT 06281
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  /38

  $465,000 Open Fri 4:30PM - 6:30PM

  • 2 Beds
  • 3 Baths
  • 1,232 Sq Ft

  233 N Society Rd, Canterbury, CT 06331

  Custom A-Frame Retreat with Expansive Westerly Views Nestled in a tranquil setting, located in Canterbury, CT, this stunning 2003 custom-built A-frame home offers a perfect blend of architectural charm and modern comfort. Designed to maximize natural light and scenic beauty, the home features striking 3M UV-tinted Andersen windows that frame sweeping westerly views and open onto a spacious front

  Heather Miller RE/MAX One

  233 N Society Rd, Canterbury, CT 06331
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  /31

  $456,500

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  243 Kemp Rd, Hampton, CT 06247

  Welcome to your dream home! This stunning property offers 2300 square feet of bright, open living space, completely renovated just 8 years ago. Situated on a sprawling 4.5-acre lot, you'll enjoy the tranquility of nature with numerous fruit trees, a fenced-in area perfect for pets, and a serene pond.The main floor boasts an inviting eat-in kitchen featuring two stainless steel island tops,

  Marie Michaud-Strout Simply Sold Real Estate

  243 Kemp Rd, Hampton, CT 06247
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  /38

  $459,000

  • 4 Beds
  • 2.5 Baths
  • 2,905 Sq Ft

  337 S Windham Rd, Willimantic, CT 06226

  Step into timeless elegance with this beautifully renovated 1850 Colonial, now featuring a brand new septic tank and central A/C system installed in April 2025-a perfect blend of historic charm and modern comfort. Nestled in the heart of Windham, this stunning 9-room home has 4 spacious bedrooms and 2.1 bathrooms, providing ample space for today's lifestyle. Inside, you'll find brand-new kitchens

  Alexia Andrade US Asset Realty

  337 S Windham Rd, Willimantic, CT 06226
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  /7

  $459,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  180 Tripp Hollow Rd, Brooklyn, CT 06234

  Brand new raised ranch is nearing completion! Excellent Brooklyn location. Great 5.75 acre rear lot, with lots of privacy and room to enjoy the outdoors. Main level features a bright open kitchen, dining and great room area with vaulted ceiling. Custom kitchen with island and farmer's sink, dining area with large window looking out to private wooded yard, sliders to back deck. Primary bedroom has

  Barbara Diaz RE/MAX Bell Park Realty

  180 Tripp Hollow Rd, Brooklyn, CT 06234
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  /6

  $454,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,428 Sq Ft

  178 Tripp Hollow Rd, Brooklyn, CT 06234

  Be in your new home this summer! Brand new raised ranch in Brooklyn is nearing completion. Lovely 2.53 acre rear lot, with lots of privacy and room to enjoy the outdoors. Main level features a bright open kitchen, dining and great room area with vaulted ceiling. Custom kitchen with island and farmer's sink, dining area with large window looking out to private wooded yard, sliders to back deck.

  Barbara Diaz RE/MAX Bell Park Realty

  178 Tripp Hollow Rd, Brooklyn, CT 06234
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  /36

  $420,000 Open Sun 11AM - 1PM

  • 3 Beds
  • 1.5 Baths
  • 2,408 Sq Ft

  16 North Rd, Ashford, CT 06278

  Charming Antique Home with Timeless Beauty and Modern Comforts Step into the elegance of yesteryear with this beautifully maintained 3-bedroom, 2-bathroom antique home, where classic charm meets thoughtful updates and professionally landscaped surroundings. Nestled in a picturesque setting, this home welcomes you with warmth, character, and enduring appeal. Inside, you'll find sun-filled rooms,

  Kerri Mullen CR Premier Properties

  16 North Rd, Ashford, CT 06278
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  /34

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,642 Sq Ft

  34 Bonnette Ave, Thompson, CT 06277

  Welcome to this beautifully maintained 3-bedroom, 2-bath home nestled in one of Thompson's most desirable neighborhoods. This charming residence offers the perfect blend of comfort, style, and functionality - ideal for families, professionals, or anyone looking for peaceful suburban living with convenient access to local amenities. Step inside to discover a spacious and sun-filled layout,

  Jason Flibbert O'Rourke Grp RE Professionals

  34 Bonnette Ave, Thompson, CT 06277
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  /37

  $435,000

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  24 Mockingbird Dr, Danielson, CT 06239

  Welcome to Easy Living At BRIARWOOD FALLS! This 55+ Single-Family HomeIs a Stunner! Located in a beautifully maintained condo community, this charming 2-bedroom, 2-bathroom home offers the perfect blend of comfort, style, and low-maintenance living. Step inside to an inviting open floor plan featuring vaulted ceilings, a gourmet kitchen which is designed with white cabinetry, quartz

  Cary Marcoux RE/MAX Bell Park Realty

  24 Mockingbird Dr, Danielson, CT 06239
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  /9

  $499,995

  • 8 Beds
  • 8 Baths
  • 4,160 Sq Ft

  8 High St, Putnam, CT 06260

  "Exceptional Investment Opportunity in Putnum CT, 8-unit property featuring two separate buildings on a generously sized lot, offering both immediate income potential and exciting development prospects. Building 1 stands ready for immediate occupancy, featuring 4 vacant 1 bed units meticulously maintained and prepared for new tenants. while you explore options for the second building. Building 2,

  Karim Douich William Raveis Real Estate

  8 High St, Putnam, CT 06260
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  /29

  $495,000 Open Sat 11AM - 1PM

  • 3 Beds
  • 2 Baths
  • 1,832 Sq Ft

  11 Stone House Dr, Moosup, CT 06354

  Built in 2017, this beautifully maintained home offers comfort and timeless style in an extremely desirable neighborhoods. Three spacious bedrooms, including the primary suite on the main level with huge walk in closet. Two additional bedrooms are located on the upper level great for family and guests. This home has a tremendous amount of quality finishes with a gormet kitchen that opens up to

  Nicole Garbutt RE/MAX Bell Park Realty

  11 Stone House Dr, Moosup, CT 06354
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  /30

  $479,900

  • 4 Beds
  • 2.5 Baths
  • 3,163 Sq Ft

  25 Charlton Ave, Dayville, CT 06241

  Looking for a home with lots of space, charm, serious curb appeal , in a desirable neighborhood? Welcome to 25 Charlton Ave Killingly a Beautiful 4 bedroom , 2.5 bath Colonial that checks all the boxes. Large updated eat in kitchen with granite countertops and center island and slider that leads to outdoor patio. The property features first floor laundry ,formal dining room with hardwoods, large

  Nicole Garbutt RE/MAX Bell Park Realty

  25 Charlton Ave, Dayville, CT 06241
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  /38

  $449,990

  • 1 Bed
  • 3 Baths
  • 752 Sq Ft

  377 Brandy Hill Rd, Thompson, CT 06277

  Just in time for summer-don't miss this adorable, turnkey cottage on Quaddick Lake! Fully furnished and move-in ready, this cozy retreat offers an updated interior with stylish cabinetry, easy-care vinyl tile flooring, and stunning lake views throughout. Mini splits provide efficient cooling, with a propane stove and electric baseboards for supplemental heat and energy control. Step out from the

  Jared Meehan RE/MAX Bell Park Realty

  377 Brandy Hill Rd, Thompson, CT 06277
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  /9

  $400,000

  • Land
  • 65 Acres
  • $6,128 per Acre

  244,278,286R Indian Hollow Rd, Windham, CT 06280

  65 Acres of Prime Land - A Rare Opportunity! Three expansive land lots totaling 65 acres are now available as one combined offering. Nestled in a peaceful and private setting, this remarkable parcels of land offers endless potential.Currently used for hunting, the property features a mix of wooded terrain and open space-ideal for outdoor recreation, wildlife enthusiasts, or those seeking a

  Amber Alcazar Coldwell Banker Realty

  244,278,286R Indian Hollow Rd, Windham, CT 06280
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  /39

  $435,000

  • 3 Beds
  • 3 Baths
  • 1,728 Sq Ft

  23-25 Waterfall Rd, Ashford, CT 06278

  Welcome to 23-25 Waterfall Road! This oversized ranch, nestled on a 3.7 acre lot, boasts three bedrooms, three full baths, two wood burning fireplaces, a sun room, in-law suite, and a spacious attached garage. Additionally, this home comes equipped with a second two bay shop that includes ample storage and a vehicle lift. Other features of this home include a skylight overlooking the large eat-in

  Franchesca Pescatello Prue Realty LLC

  23-25 Waterfall Rd, Ashford, CT 06278
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  /34

  $434,900

  • 3 Beds
  • 2.5 Baths
  • 2,024 Sq Ft

  142 Sunset Dr, Danielson, CT 06239

  Welcome to 142 Sunset Drive, a beautifully maintained 3-bedroom, 2.5-bath Colonial set on a peaceful and private lot in the heart of Killingly. This home offers a warm and functional layout that's perfect for both everyday living and entertaining. Step inside to find a generous living room, formal dining room, and a cozy family room with fireplace that opens directly to the backyard - perfect for

  Rachel Mcnally Real Broker CT, LLC

  142 Sunset Dr, Danielson, CT 06239
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  /27

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,492 Sq Ft

  17 Old Hampton Rd, Canterbury, CT 06331

  Room to grow and space to breathe on 1.7 acres! Quietly situated on a dead-end street, this charming three-bedroom, 2-bath home offers you a lifestyle of privacy and easy living with owned ground-mount solar panels. Step inside this home to discover a thoughtfully maintained residence with endless potential. The spacious kitchen and dining areas flow effortlessly into a welcoming living space,

  Kendra Bonette Coldwell Banker Realty

  17 Old Hampton Rd, Canterbury, CT 06331
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  /24

  $450,000

  • 1 Bed
  • 7,056 Sq Ft

  13 Water St, Killingly, CT 06239

  WATERFRONT COMMERCIAL / RESIDENTIAL INVESTMENT OPPORTUNITY Rare opportunity to own a 7,056 SF riverfront building at 13 Water Street in Danielson (Killingly), CT. Located just off Route 6 and I-395, minutes from RI and MA, this versatile property offers strong visibility, easy access, and excellent potential for income or owner-occupancy. Beautiful waterfront views from offices on 2nd floor, plus

  Anthony Chabot Chabot & Associates Real Estate

  13 Water St, Killingly, CT 06239
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  /13

  $499,900

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

  206 Stawicki Rd, Thompson, CT 06255

  Welcome to your future dream home—where modern living meets country charm! This to-be-built 3 bedroom, 2.5 bathroom home offers 1,900 sq. ft. of thoughtfully designed space, all set on a beautiful 1-acre lot. Enjoy the peace of mind that comes with brand-new construction—energy-efficient systems, worry-free maintenance, and today’s most desired features. Picture yourself sipping coffee on your

  James Black Real Broker MA, LLC

  206 Stawicki Rd, Thompson, CT 06255
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  /37

  $415,000

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

  3 Woodstock Ave W, Putnam, CT 06260

  This character-filled home sits on a private and generous 1.39-acre lot-offering room to breathe, space to grow, and plenty of possibilities. With 1,922 square feet, this 3-bedroom, 1.5 bath residence is move-in ready and full of potential for the right buyer with vision and energy. Durable HardiePlank fiber cement siding wraps the home in timeless style and long-term protection-resisting

  Beth Fournier Compass Connecticut, LLC

  3 Woodstock Ave W, Putnam, CT 06260
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  /40

  $419,500

  • 4 Beds
  • 2 Baths
  • 2,136 Sq Ft

  351 Brandy Hill Rd, Thompson, CT 06277

  Beautiful, completely renovated, immaculate ranch in a great location!! Just a minute away from Quaddick Lake. This home offers 4 generous sized bedrooms (2 upstairs and 2 downstairs) and 2 full baths. As soon as you walk in, you get the feeling this is not just a regular house, it's a HOME. Outside offers a HUGE detached 2 and a half car garage and a back deck, perfect for sitting outside on a

  Matthew Huberdault Real Broker CT, LLC

  351 Brandy Hill Rd, Thompson, CT 06277
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  /14

  $499,900

  • 3 Beds
  • 2 Baths
  • 2,362 Sq Ft

  94 Stone Rd, Dayville, CT 06241

  Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $4,999 back in closing costs credits OR $2,364 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 2003 Log Home with open floor plan, cathedral ceilings, and

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

  94 Stone Rd, Dayville, CT 06241
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  /39

  $489,999

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  24 River Rd, Sterling, CT 06377

  This country home has undergone a studs out renovation and expansion where charm, space, and modern comfort come together on over 5+ acres of land and you are just 5 miles from I-395. The home blends a timeless style with smart, up-to-date living. One of the home's standout features is the massive primary bedroom with cathedral ceilings, which makes the space feel even more grand and offers a

  Beth Fournier Compass Connecticut, LLC

  24 River Rd, Sterling, CT 06377
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  /23

  $419,900

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  283 Woodstock Ave, Putnam, CT 06260

  BUYER GOT COLD FEET! THEIR LOSS IS YOUR GAIN! Ready for your new energy efficient, solar powered home built in 2020 within walking distance of downtown?! This beauty sits on just under 1/2 acres and has a seasonal water course that runs right through the backyard. If high energy costs got you down and you're ready to start saving some money, look no further. This family of 3 adults and several

  Sean Nelson Property Investors & Advisors

  283 Woodstock Ave, Putnam, CT 06260
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  /36

  $469,000

  • 4 Beds
  • 1.5 Baths
  • 2,403 Sq Ft

  40 Hartford Pike, Dayville, CT 06241

  Gorgeous Colonial with All the CHARM you will want with 2403sqft(doesnt include finished attic), 11 rooms, 4 Bedrms, 1.1 Baths, 3 CAR GARAGE, !.8 AC, Large Chicken Coup/Playhouse/Shed (You decide), Fruit/Veg/flower stand with power & refrigeration (Grow your own Veggies or make your own pies to sell) So many possibilies. Sits PRIVATELY OFF THE ROAD with the most SCENIC VIEW. Come see this

  Irene Adams Signature Properties of NewEng

  40 Hartford Pike, Dayville, CT 06241
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  /16

  $449,999

  • 4 Beds
  • 2 Baths
  • 2,054 Sq Ft

  94 Mansfield Rd, Ashford, CT 06278

  Welcome to 94 Mansfield Road in Ashford, CT! This charming property boasts a rare blend of natural beauty and ample space, making it the perfect retreat! Nestled on 8 picturesque acres with river access and a scenic walkway, this home invites you to enjoy peaceful country living. The property includes a large barn, shed, and spacious garage, which provides plenty of storage and room for hobbies.

  Lexie Brunet Brunet and Company Real Estate

  94 Mansfield Rd, Ashford, CT 06278
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  /4

  $499,900

  • Land
  • 11 Acres
  • $44,834 per Acre

  117 Riverside Dr, North Grosvenordl, CT 06255

  Great opportunity awaits on this 11 acre multi use property that runs along the airline trail. Some of the many potential uses would be townhouses, duplex's, multi families and single family homes. Gravel is on site. City sewer and 3 phase power. This property is located near 395 which is great for easy commuting into Massachusetts. .

  Cary Marcoux RE/MAX Bell Park Realty

  117 Riverside Dr, North Grosvenordl, CT 06255
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  /24

  $479,900

  • 3 Beds
  • 1.5 Baths
  • 1,708 Sq Ft

  1015 Route 198, Woodstock, CT 06281

  Spring is coming and this charming cape is ready to be your new home. Meticulously done with so many new features. Large living room with fireplace, or woodstove and gleaming hardwood floors through out! Screened in porch just waiting for you to enjoy your morning coffee. Updated bathrooms, kitchen, newer appliances...every inch has been painted and made ready for its new owner. New Septic,

  Amy Vinal Pine Knoll Real Estate

  1015 Route 198, Woodstock, CT 06281
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  /39

  $410,000

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  13 Henry Dr, Moosup, CT 06354

  Welcome to low maintenance easy living in the great community of Moosup River Estates. When you step inside this charming 2 bedroom, 2 bathroom standalone condo you will be overly impressed with the immaculate condition of this home. This designer Robin Model Condo has upgraded fixtures and finishes with an open floor concept all on a single level. With your Kitchen, Dining and living space

  Alexcia Merritt RE/MAX Bell Park Realty

  13 Henry Dr, Moosup, CT 06354
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  /7

  $450,000

  • Land
  • 4.50 Acres
  • $100,000 per Acre

  0 Putnam Rd Unit 24065166, Plainfield, CT 06332

  Discover the potential of this prime piece of land at 0 Putnam Rd, Plainfield! This spacious residential lot offers endless possibilities, whether you're envisioning your dream home or exploring its potential as a commercial property. With a strategic location near major roadways and local amenities, this lot provides the perfect balance of convenience and opportunity. Positioned in a growing

  Phil Davis eXp Realty

  0 Putnam Rd Unit 24065166, Plainfield, CT 06332
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  /13

  $497,500

  • Land
  • 2.32 Acres
  • $214,440 per Acre

  454 Providence Rd, Brooklyn, CT 06234

  2.32 Acres vacant land zoned (PC) Planned Commercial located directly at the 4-way traffic light to the entrance of the Brooklyn Walmart Supercenter. Easement agreement in the public record would allow for access to the parcel from the Walmart driveway entrance. Less than 2.5 miles from I-395 (NB Exit 37/SB Exit 37B). Situated in the heart of the Route 6 retail corridor. National tenants in the

  Ron Lyman Lyman Real Estate

  454 Providence Rd, Brooklyn, CT 06234
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  /34

  $499,900 New Construction

  • 4 Beds
  • 3 Baths
  • 2,000 Sq Ft

  18 Valley View Dr, Killingly, CT 06241

  Welcome to your custom built new home located close to the Rhode Island Line, Mass line and 395! This beautiful home boasts 2000 sf of comfortable living in a new community of new builds. Pick out your flooring, cabinetry, countertops and more! Work closely with the builder to make your new home the home of your dreams!

  Colleen Rybacki Brunet and Company Real Estate

  18 Valley View Dr, Killingly, CT 06241
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  /8

  $430,000 New Construction

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

  7 Autumn Ridge, Windham, CT 06280

  Beautiful Custom Colonial To Be Built on 1.81 Acre Level Lot!

  Cathyann Schulte Countryside Realty

  7 Autumn Ridge, Windham, CT 06280
• 

  

  /12

  $439,000 New Construction

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

  1157 Windham Rd, Windham, CT 06266

  New Raised Ranch Close to completion. Nice Lay out with 3 bedrooms, including a primary suite with walk in closet, and its own full bath. Main level kitchen, dining, and living room, all flow together as one large open space. This open living area area also separates the the bedrooms, with the primary suite on one side, and the two other bedrooms, and a full bath on the other. Lower level has a

  Timothy Morse Home Selling Team

  1157 Windham Rd, Windham, CT 06266
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  /24

  $465,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,900 Sq Ft

  1145 Windham Rd, Windham, CT 06266

  COMPLETED AND READY TO MOVE IN. Brand new construction!! Wonderful floor plan, with a large and open area encompassing the kitchen, dining and living room areas. Tons of natural light coming from windows, and sliders in dining area. Main level includes a flex room, and a half bath. Upstairs you will find the three bedrooms, including a primary with its own full bath and walk in closet, as well as

  Timothy Morse Home Selling Team

  1145 Windham Rd, Windham, CT 06266

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