Windham County CT Homes under $500,000

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  /37

  $425,000

  • 4 Beds
  • 3 Baths
  • 2,352 Sq Ft

  53 Windham Rd, Hampton, CT 06247

  Welcome to your private oasis! Set on nearly 5 acres, with half of the pond to yourself, this beautifully updated 4-bedroom, 3-bath home offers 2,352 square feet of comfortable living space with pond views. The open floor plan on the main level is perfect for entertaining, and recent upgrades include new flooring, a brand new deck and new master patio, and upgraded septic tanks just to name a few

  

  Stephanie Rush

  RE/MAX Legends

  (860) 891-6092

  53 Windham Rd, Hampton, CT 06247
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  /31

  $494,900

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

  31 Cherry Hill Rd, Brooklyn, CT 06234

  This is the one to see! 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

  

  Nathan Cholewa

  Kazantzis Real Estate, LLC

  (860) 431-3428

  31 Cherry Hill Rd, Brooklyn, CT 06234
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  /39

  $499,900

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

  39 Huntington Dr, Plainfield, CT 06374

  PRICE ADJUSTMENT!!! This beautiful Colonel is a true treasure, If you value privacy, this home sits off the road on 3 and a half acres. It offers the perfect blend of modern luxury and comfort. The First floor features hardwood floors, front to back living room which is open to the rear deck, Easy access from the 2-3 car garage to the kitchen, a formal dining room and a half bath. The Kitchen

  

  Deb Schusterman

  Brizo Real Estate Services

  (860) 467-1719

  39 Huntington Dr, Plainfield, CT 06374
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  /32

  $420,000

  • 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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  /31

  $469,900 New Construction

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

  12 South St, Brooklyn, CT 06234

  Brand New Contemporary Raised Ranch on a Beautiful 1 Acre Wooded Lot in Brooklyn. Just getting started! There is still time to make some choices!! Estimated Completion Date is August 31, 2025. Four Bedrooms & 3 Full Bathrooms. Central AC. Two Car Garage. Vaulted Ceilings. Beautiful Kitchen w/ Granite Counters & Center Island. Gleaming Hardwood Floors. Spacious Vaulted Ceilings. High Efficiency

  Bill Heenan William Raveis Real Estate

  12 South St, Brooklyn, CT 06234
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  /40

  $441,750 New Construction

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

  1157 Windham Rd, Windham, CT 06266

  New Raised Ranch Close to completion and available to view. 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

  Timothy Morse Home Selling Team

  1157 Windham Rd, Windham, CT 06266
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  /24

  $459,000 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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  /33

  $499,000

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

  111 Sterling Hill Rd, Moosup, CT 06354

  GREAT LOCATION...This raised ranch located in the outskirts of Plainfield, just minutes from the Rhode Island line, is a hidden gem with 4 bedrooms and 3 full baths spread across approximately 1,800 square feet. The main level features an open floor plan with vaulted ceilings, oak hardwood floors, a kitchen with white shaker style cabinets and granite countertops, and 3 bedrooms including the

  Jennifer Jackson Berkshire Hathaway NE Prop.

  111 Sterling Hill Rd, Moosup, CT 06354
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  /40

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 2,320 Sq Ft

  93 Cook Hill Rd, Danielson, CT 06239

  Spacious colonial in immaculate, move-in condition. First floor features a bright, open floor plan with a large living room, dining area, eat-in kitchen with pantry closet and stainless appliances, a home office, and a half bath. There is also a lovely vaulted sunroom with newly installed electric heat, and a spacious deck with a canopy. The second floor has a large primary suite with a full bath

  Barbara Diaz RE/MAX Bell Park Realty

  93 Cook Hill Rd, Danielson, CT 06239
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  /27

  $469,000

  • 4 Beds
  • 3.5 Baths
  • 2,075 Sq Ft

  31 Bob White Way, Moosup, CT 06354

  Welcome to this beautifully maintained raised ranch offering 4 generous sized bedrooms, ample Primary Bedroom. 3 full bathrooms perfectly designed for comfort, flexibility and extended living options. The main level features a bright, airy remodeled kitchen, perfect for entertaining. Open concept living/dining area with plenty of natural light. The lower level offers potential for an in law area.

  Maria Marcotte RE/MAX One

  31 Bob White Way, Moosup, CT 06354
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  /40

  $479,900

  • 3 Beds
  • 3.5 Baths
  • 2,389 Sq Ft

  80 Tuckie Rd, Windham, CT 06280

  Beautiful Contemporary on 2.06 acres of professionally landscaped grounds. Home is set back off the road allowing for privacy and space. Walk thru the front door and there is a first floor bedroom and full bath for single floor living if that is what you need. As you continue on it opens up to an open floor plan with soaring vaulted ceilings, skylights and large windows which bring in amazing

  Lisa Pekala Century 21 Clemens Group

  80 Tuckie Rd, Windham, CT 06280
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  /29

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,682 Sq Ft

  70 Laurel Hill Dr, Woodstock Valley, CT 06282

  Get ready to fall in love with this fully renovated colonial, just one minute from the beach and offering stunning water views! What was once a charming 1,200 sq ft Cape has been recently completely reimagined into a spacious 1,600 sq ft Colonial. This like-new home now boasts 3 bedrooms, 2.5 bathrooms, and a fresh, modern layout perfect for everyday living and entertaining. The heart of the home

  Katelyn Battista Real Broker CT, LLC

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

  $469,000

  • 3 Beds
  • 2 Baths
  • 2,467 Sq Ft

  226 Harris Rd, Sterling, CT 06377

  Spacious Raised Ranch with Modern Comforts and Country Charm in Sterling! Welcome to this beautifully expanded 3-bedroom, 2.5-bath raised ranch nestled on over an acre of serene countryside in Sterling. This home offers a perfect blend of comfort, space, and versatility, ideal for those seeking privacy and room to grow. Step inside to find a modern tile kitchen equipped with everything you need

  Coleen Brakenwagen Jason Mitchell Real Estate Connecticut LLC

  226 Harris Rd, Sterling, CT 06377
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  /39

  $475,000

  • 4 Beds
  • 3.5 Baths
  • 2,630 Sq Ft

  126 Grand View Terrace, Brooklyn, CT 06234

  Welcome to 126 Grandview Terrace - a stately Colonial with classic brick exterior, nestled on nearly an acre in beautiful, rural Brooklyn! This spacious 4 bedroom, 3 1/2 bath home has been lovingly maintained by the same owners for almost 30 years. The home offers over 2600 sq ft of living space, blending timeless charm with modern comfort. Step inside to find a warm and inviting layout featuring

  Sue Esposito Home Selling Team

  126 Grand View Terrace, Brooklyn, CT 06234
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  /40

  $469,000

  • 3 Beds
  • 2 Baths
  • 2,527 Sq Ft

  118 Putnam Rd, Pomfret Center, CT 06259

  Welcome to this spacious and versatile home in the heart of desirable Pomfret, CT. Offering over 2,500 square feet of quality living space, this thoughtfully designed property is ideal for a variety of lifestyles and living arrangements. The flexible layout features three bedrooms and two full baths, along with a full kitchen on each level, providing the perfect setup for a seamless single-family

  John Downs Berkshire Hathaway NE Prop.

  118 Putnam Rd, Pomfret Center, CT 06259
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  /39

  $464,999

  • 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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  /35

  $459,900

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

  180 Tripp Hollow Rd, Brooklyn, CT 06234

  Brand new raised ranch is complete and ready for occupancy! 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.

  Barbara Diaz RE/MAX Bell Park Realty

  180 Tripp Hollow Rd, Brooklyn, CT 06234
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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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  /4

  $465,000

  • 4 Beds
  • 4 Baths
  • 5,176 Sq Ft

  50 High St, Moosup, CT 06354

  This expansive Cape Cod-style home is a hidden gem, situated on 2.72 acres with a wraparound driveway complemented by an additional parking area. The two-car garage is located beneath the house, and the home features spacious rooms with ample storage throughout. The dining room boasts a beautiful fieldstone fireplace, while the bar area is carpeted wall-to-wall. The kitchen offers abundant

  Liz Lavallee Dawn Taylor Real Estate

  50 High St, Moosup, CT 06354
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  /2

  $475,000

  • 2 Beds
  • 2 Baths
  • 1,780 Sq Ft

  6 Grace Ln, Moosup, CT 06354

  Own Your Dream Home with Zero Money Down! Unlock the door to your future with an exclusive offer: Purchase this home and receive $4,750 back in closing costs credits OR $2,811 per month at an exceptional financing rate of 5.88% APR with ZERO down payment available for those who qualify. Your Private Oasis Awaits! Welcome to this stunning end-unit luxury condo, built in 2021 and located in

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

  6 Grace Ln, Moosup, CT 06354
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  /38

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,359 Sq Ft

  422 Zaicek Rd, Ashford, CT 06278

  Come see this one-of-a-kind, cozy contemporary ranch offering exceptional privacy and peaceful country living. Situated on over 12 acres and comprised of two separate parcels, this custom-built home is tucked away a few hundred yards off Zaicek Road, yet is only a 15-minute drive to the UConn campus. As you step inside, you're welcomed by an open-concept space that combines the living room,

  Thomas Walsh Century 21 AllPoints Realty

  422 Zaicek Rd, Ashford, CT 06278
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  /39

  $495,000

  • 2 Beds
  • 2 Baths
  • 1,613 Sq Ft

  4 Skylark Ln Unit 4, Killingly, CT 06239

  Welcome to Briarwood Falls, a desirable 55+ community offering the ease of single-family living with all the benefits of a condo lifestyle. This well-maintained 2-bedroom, 2-bath ranch features an open floor plan with vaulted ceilings, a spacious applianced kitchen with breakfast bar, and a walk-in pantry. The generously sized primary suite offers comfort and convenience with a private bathroom,

  Cary Marcoux RE/MAX Bell Park Realty

  4 Skylark Ln Unit 4, Killingly, CT 06239
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  /36

  $429,000

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

  117 Woodside St, Putnam, CT 06260

  Beautiful 4-bedroom, 2-bath Colonial offering 2,270 square feet of comfortable living space. The open-concept main level features exposed beam ceilings and an updated kitchen with brand new granite countertops and a convenient breakfast bar. Both bathrooms have been tastefully updated, and the home includes newer windows throughout. Enjoy a large fenced-in backyard, perfect for relaxing or

  Jaclyn Smith Coldwell Banker Realty

  117 Woodside St, Putnam, CT 06260
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  /36

  $425,000

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  367 Pine Hill Rd, Sterling, CT 06377

  Charming Ranch House in Tranquil Sterling, CT, welcome to your dream home in a small-town atmosphere! Nestled on a stunning 1.46-acre lot in the picturesque town of Sterling, Connecticut, this beautifully updated ranch house presents an exceptional blend of comfort and modern elegance. Two-bedroom, one-bathroom, updated flooring, newer appliances, perfectly designed for relaxation and nature

  Allen Gammons BHHS Commonwealth/Robert Paul

  367 Pine Hill Rd, Sterling, CT 06377
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  /38

  $439,000

  • 2 Beds
  • 1.5 Baths
  • 1,048 Sq Ft

  361 Westminster Rd, Canterbury, CT 06331

  Step into history with modern comfort at 361 Westminster Road in Canterbury, CT. Originally built in 1800, this beautifully restored 2-bedroom, 1.5-bath home blends classic New England character with thoughtful updates throughout. Featuring brand-new flooring, fresh paint, a new roof, and ductless air conditioning units, this home is completely move-in ready. The updated kitchen showcases butcher

  Adam Gumula Kazantzis Real Estate, LLC

  361 Westminster Rd, Canterbury, CT 06331
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  /24

  $424,999

  • 3 Beds
  • 2 Baths
  • 1,320 Sq Ft

  101 Prospect St, Putnam, CT 06260

  Welcome to this adorable 3-bedroom, 2-bathroom home with a one-car garage, perfectly located in the vibrant and historic town of Putnam. Step inside to a cozy main level featuring a warm fireplace, ideal for relaxing evenings. The kitchen offers plenty of space and charm for everyday living. This home is nestled in such a great neighborhood! Looking to start a family but haven't been able to find

  Ashley Walker Brunet and Company Real Estate

  101 Prospect St, Putnam, CT 06260
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  /36

  $484,999

  • 8 Beds
  • 4 Baths
  • 4,808 Sq Ft

  40 Elm St, Willimantic, CT 06226

  ATTENTION INVESTORS!!! This incredible 10 CAP investment Opportunity for 4 units across 2 2-family properties may be exactly what you're looking for!!! Discover the potential in this centrally located low overhead property. With strong rental demand from nearby ECSU, Uconn and in the general market, vacancy will not be a problem. Tenant amenities include large backyards, with privacy and gardens.

  Robyn Letourneau Berkshire Hathaway NE Prop.

  40 Elm St, Willimantic, CT 06226
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  /35

  $489,999

  • 8 Beds
  • 4 Baths
  • 3,828 Sq Ft

  389 Pleasant St, Windham, CT 06226

  Prime Investment Opportunity in Willimantic! Excellent potential in a high-demand, low vacancy location. With strong bones, proximity to ECSU, public transit and downtown this property is perfect for investors or house hackers looking to build equity fast. NEW ELECTRIC PANELS, NEW HEAT AND HOT WATER FURNACES. Combine with other listed Willimantic properties: Elm st., Jackson St., and Chapman St.

  Robyn Letourneau Berkshire Hathaway NE Prop.

  389 Pleasant St, Windham, CT 06226
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  /34

  $499,900

  • 2 Beds
  • 1.5 Baths
  • 2,954 Sq Ft

  192 Palmer Rd, Chaplin, CT 06235

  Tucked away at the end of a long, private driveway, this sprawling 2-bedroom ranch offers the ultimate in privacy and tranquility. Set on a picturesque 4-acre lot surrounded by nature, this home is perfect for those seeking a peaceful retreat with room to roam. Inside, you'll find a spacious and flexible floor plan with generous living areas, large windows that bring the outdoors in, and the ease

  Lisa Barstow Simply Sold Real Estate

  192 Palmer Rd, Chaplin, CT 06235
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  /40

  $485,000

  • 8 Beds
  • 3.5 Baths
  • 5,134 Sq Ft

  4 Main St, Willimantic, CT 06226

  Terrific Investment Opportunity! Don't miss this rare chance to own a well-maintained multi-unit property with strong income potential. The main house features a spacious layout with 5 bedrooms, ideal for large households or rental flexibility. Behind the main home, you'll find a separate 2-bedroom unit, perfect for extended family or additional rental income. Additionally, there's a third unit-a

  Tammy Arute Arute Realty Group LLC

  4 Main St, Willimantic, CT 06226
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  /33

  $469,900

  • 6 Beds
  • 3.5 Baths
  • 2,684 Sq Ft

  34 2nd St Unit 36, Plainfield, CT 06374

  Amazing opportunity to own a 2-unit home offering 3 bedrooms, and 2 baths each side with its own laundry. The right side was completely gutted in 2024 and renovated from the ground up, with NEW insulation, sheetrock, vinyl plank flooring, Windows, splitters for heat & AC, Kitchen with 5 appliances and 2 full baths. Outside the home has a new roof, siding, asphalt driveways, porch and deck, and

  Pat Malek First Choice Realty

  34 2nd St Unit 36, Plainfield, CT 06374
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  /12

  $419,900

  • 3 Beds
  • 2 Baths
  • 1,236 Sq Ft

  363 South St, Brooklyn, CT 06234

  Stunning new construction in Brooklyn, CT! This beautifully built raised ranch offers 3 bedrooms and 2 full baths, with a bright open-concept layout that's perfect for everyday comfort. The kitchen is equipped with granite countertops and designer-selected light fixtures. Enjoy a tub and a walk-in shower, a walk out deck, and one-car garage. This stylish, move-in ready home is minutes from route

  Andrew Kausch Kazantzis Real Estate, LLC

  363 South St, Brooklyn, CT 06234
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  /36

  $430,000

  • 3 Beds
  • 2 Baths
  • 1,489 Sq Ft

  29 Birchwood Dr, Dayville, CT 06241

  Welcome to 29 Birchwood Drive in Killingly - a welcoming ranch-style home nestled in a charming neighborhood! This 3 bedroom, 2 bath gem features a spacious 2-car garage and a large unfinished basement offering endless potential. Step outside to a beautifully landscaped, fully fenced-in back yard that is perfect for relaxing, letting pets roam free, or ideal for summer entertaining. With its

  Tina Keith Coldwell Banker Realty

  29 Birchwood Dr, Dayville, CT 06241
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  /34

  $475,000

  • 4 Beds
  • 3 Baths
  • 2,860 Sq Ft

  144 Underwood Rd, Putnam, CT 06260

  Welcome home to this expansive 4-bedroom, 3-bathroom split-level style home which offers plenty of space and comfort! The upper level features a bright and airy living room that flows seamlessly into the kitchen and dining area. The kitchen is complete with granite countertops, stainless steel appliances, and a convenient breakfast bar. Down the hall, the expansive primary suite impresses with

  Andrew Bruce Lamacchia Realty

  144 Underwood Rd, Putnam, CT 06260
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  /28

  $400,000

  • 4 Beds
  • 1.5 Baths
  • 1,582 Sq Ft

  171 David Cir, Putnam, CT 06260

  Welcome to this warm and inviting four bedroom one and a half bath, raised ranch, proudly cared for by its original owners for more than half a century. Set on a beautifully landscaped lot, this home radiates pride of ownership. Step inside to discover updated flooring throughout the main living areas (2024). Replacement windows with a lifetime warranty fill the space with natural light and offer

  Valerie MacNeil Kazantzis Real Estate, LLC

  171 David Cir, Putnam, CT 06260
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  /39

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,664 Sq Ft

  58 Snake Meadow Rd, Danielson, CT 06239

  Set back nearly 200 feet from the road on a picturesque 4+ acre lot, this beautifully maintained newer Colonial offers a perfect blend of privacy, charm, and modern comfort. A curved driveway leads to the inviting home featuring an open layout, hardwood floors, and a center-island kitchen with sliders to a spacious outdoor area-ideal for entertaining or relaxing. The main level includes a cozy

  Jacob Rochefort Mott & Chace Sotheby's Intl Rt

  58 Snake Meadow Rd, Danielson, CT 06239
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  /40

  $434,000

  • 2 Beds
  • 2.5 Baths
  • 1,430 Sq Ft

  4 Bluebird Ln Unit 4, Dayville, CT 06241

  Welcome to Eagle Ridge Estates, a quiet, well-maintained community. This beautifully designed 2 bedroom, 2.5 bath ranch style condo offers refined comfort, flexible space, and open concept living. The living room features vaulted ceilings, a custom gas fireplace that serves as a warm focal point and hardwood floors. The kitchen includes updated appliances, abundant cabinets, granite countertops,

  Valerie MacNeil Kazantzis Real Estate, LLC

  4 Bluebird Ln Unit 4, Dayville, CT 06241
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  /40

  $449,900

  • 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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  /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
• 

  

  /31

  $454,900

  • 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 complete, and ready for occupancy! 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

  Barbara Diaz RE/MAX Bell Park Realty

  178 Tripp Hollow Rd, Brooklyn, CT 06234

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