Windham County CT Houses for Sale

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  /40

  $989,000

  • 3 Beds
  • 4.5 Baths
  • 3,827 Sq Ft

  236 Deerfield Rd, Pomfret Center, CT 06259

  There are properties, and then there are properties that invite you to imagine an entirely different way of living. Set in the heart of picturesque Pomfret, this extraordinary 51-acre estate offers a rare combination of land, history, architectural charter and limitless potential. For those who have envisioned an authentic country estate, the possibilities are extraordinary. Create a refined

  Cynthia Sherman Berkshire Hathaway NE Prop.

  236 Deerfield Rd, Pomfret Center, CT 06259
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  /27

  $400,000

  $25K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,891 Sq Ft

  48 Edmond St, Putnam, CT 06260

  LEGAL IN-LAW! Multi-generational living? Location great for MA, CT, or RI. Need a home office? Guest suite? This one has options! Room count doesn't tell the whole story. Fully remodeled home featuring a legal in-law apartment with both interior access and a private entrance. A connecting bedroom between the main home and in-law. THREE FULL & ONE HALF BATH! New kitchen: Stainless appliances,

  Brian Connolly Real Broker CT, LLC

  48 Edmond St, Putnam, CT 06260
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  /40

  $669,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,400 Sq Ft

  29 Ashford Rd, Eastford, CT 06242

  Welcome to this stunning newly constructed home in Eastford, Connecticut, where modern craftsmanship meets the tranquility of a picturesque wooded setting. Thoughtfully designed with quality finishes and custom upgrades throughout, this home showcases beautiful timber frame accents, board-and-batten siding, a metal roof accent, and striking black Anderson windows that create exceptional curb

  Eric Gregan ERA Blanchard & Rossetto

  29 Ashford Rd, Eastford, CT 06242
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  /40

  $575,000

  $45K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  269 Black Hill Rd, Plainfield, CT 06374

  Experience the comfort of one-level living in this custom-built ranch-style home set on a spacious lot in Plainfield, offering the perfect blend of privacy, functionality, and everyday convenience. With approximately 3,000 square feet of living space, this thoughtfully designed home features 4 bedrooms, 3 full bathrooms, plus a dedicated office that can easily serve as a 5th bedroom. Step inside

  Darius Baturo Berkshire Hathaway NE Prop.

  269 Black Hill Rd, Plainfield, CT 06374
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  /37

  $289,000

  $51K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  23 Winter St, Danielson, CT 06239

  Classic details and practical updates come together in this charming home, where the covered front porch and fenced front yard set a welcoming first impression. The main level offers an easy daily layout with a mudroom, half bath, flexible office or bonus room, a spacious living room with a bow window and built-in bookshelves. The dining room adds character with wainscoting and crown molding,

  Lauren Heidelberger Berkshire Hathaway NE Prop.

  23 Winter St, Danielson, CT 06239
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  /37

  $545,000

  • 4 Beds
  • 3 Baths
  • 2,893 Sq Ft

  128 Holmes Rd, Pomfret Center, CT 06259

  Investors, take notice! This antique Colonial is situated on an impressive 6.6-acre private lot offering a peaceful setting and endless potential. A portion of the acreage is already cleared, while the property also features three beautiful ponds and plenty of outdoor space to enjoy the tranquil surroundings. Inside, the home offers 4 bedrooms, 3 full bathrooms, and a walk-out basement, providing

  Lyle Rotondo Berkshire Hathaway NE Prop.

  128 Holmes Rd, Pomfret Center, CT 06259
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  /40

  $695,000

  $4K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,182 Sq Ft

  250 Killingly Rd, Pomfret, CT 06259

  Welcome to this beautifully renovated home in desirable Pomfret CT! Offering the perfect blend of modern updates, flexible living space, and country charm, this impressive property is ready for its next owners. Inside, you'll find five spacious bedrooms and three full bathrooms, providing plenty of room for family, guests, or multi-generational living. The massive dining and flex space, offers

  Amy Therrien The Neighborhood Realty Group

  250 Killingly Rd, Pomfret, CT 06259
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  /40

  $250,000

  • 2 Beds
  • 1 Bath
  • 1,136 Sq Ft

  16 Breaults Ln, Thompson, CT 06277

  Calling all investors, contractors, and ambitious renovators! Enjoy a rare opportunity just moments from beautiful Quaddick Lake with a seasonal water view, deeded right-of-way access to the lake, and close proximity to Quaddick State Park for boating, fishing, swimming, hiking, and year-round recreation. The property features a 2-bedroom, 1-bath main home and a detached 1-car garage with an

  Kara Mazzola First Choice Realty

  16 Breaults Ln, Thompson, CT 06277
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  /34

  $360,000

  Open Sun 10AM - 12PM $35K PRICE INCREASE

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

  15 Cracow Ave, Windham, CT 06280

  Welcome to 15 Cracow Ave in Windham, a beautifully updated 3-bedroom, 2-full-bath ranch offering the perfect blend of single-level living, modern finishes, and outdoor lifestyle. Step inside to an inviting open floor plan where the completely remodeled kitchen flows seamlessly into the dining area and spacious living room. The kitchen has been tastefully upgraded with quartz countertops,

  AJ Davis Better Homes and Gardens Real Estate Executive Real Estate

  15 Cracow Ave, Windham, CT 06280
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  /40

  $2,950,000

  • 4 Beds
  • 5 Baths
  • 4,442 Sq Ft

  282 & 260 Searles Rd, Pomfret, CT 06259

  A rare and refined country estate offering privacy, luxury, and elegance on over 53 acres in scenic Pomfret. This extraordinary 4,442 sq ft custom, Tennessee fieldstone home includes 4 bedrooms and 5 baths-including a private in-law apartment/second primary suite with its own entrance. An additional 16+ acre building lot provides development potential. Surrounded by forest and adjacent to 175

  John Downs Berkshire Hathaway NE Prop.

  282 & 260 Searles Rd, Pomfret, CT 06259
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  /35

  $325,000

  Open Sun 10:30AM - 12PM

  • 2 Beds
  • 1 Bath
  • 720 Sq Ft

  1092 Plainfield Pike, Sterling, CT 06377

  This fully renovated home combines style, effortless 1 level living, & a rare, brand new 3 car garage that truly steals the show. Everything you need is conveniently located on 1 floor, creating an accessible, easy-to-enjoy layout w/ absolutely NOTHING left to do but move in. The standout new three-car garage is a major plus and offers the kind of versatility that is hard to find. Bring the

  Kim Synott eXp Realty

  1092 Plainfield Pike, Sterling, CT 06377
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  /40

  $599,999

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

  109 Starkweather Rd, Plainfield, CT 06374

  Offered for the first time, this lovingly maintained one-owner Cape is nestled in a peaceful country setting surrounded by mature trees and natural beauty. Built in 2003, this spacious home offers 2700 square feet. The main level features a private primary suite with its own deck, oversized walk-in closet/dressing room, and ensuite bath with soaking tub and separate shower. The inviting layout

  Sheena Ruggirello Real Broker CT, LLC

  109 Starkweather Rd, Plainfield, CT 06374
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  /40

  $399,900

  • 2 Beds
  • 2 Baths
  • 1,448 Sq Ft

  421 Modock Rd, Putnam, CT 06260

  Located on over 4 AC of Agricultural zoned land in West Putnam, this 2 bedroom 2 bathroom Ranch style home is just the property you have been looking for. Home is well maintained and still owned by members of the original family. Home features a 1 car attached garage along with plenty of parking on & off the paved driveway. A large kitchen has ample working space and is open to the dining area. A

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  421 Modock Rd, Putnam, CT 06260
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  /25

  $419,999

  $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 4,492 Sq Ft

  36 S Main St, Putnam, CT 06260

  Exceptional mixed-use opportunity in the heart of Downtown Putnam! This versatile property features a well-maintained 2-bedroom, 2-bath residence paired with an impressive 2800 sq. ft. warehouse complete with its own private entrance, offering endless possibilities for business, storage, workshop space, or investment potential. Ideally situated in Putnam's thriving downtown district, you'll enjoy

  Ashley Walker Kazantzis Real Estate, LLC

  36 S Main St, Putnam, CT 06260
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  /40

  $749,900

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,696 Sq Ft

  84 Dark Lantern Hill Rd, Danielson, CT 06239

  Welcome to your own private country retreat! This exceptional log home offers the perfect blend of rustic charm and modern updates, nestled on a picturesque property designed for those seeking peace, privacy, and room to roam.The heart of the home is the brand-new great room addition, featuring soaring cathedral ceilings, abundant natural light, and direct access to a spacious deck overlooking

  Lisa Harrison J. Christopher Real Estate Group

  84 Dark Lantern Hill Rd, Danielson, CT 06239
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  /22

  $450,000

  • 4 Beds
  • 2 Baths
  • 1,690 Sq Ft

  8 Plainview Dr, Plainfield, CT 06374

  Welcome to 8 Plainview Drive, a beautifully updated 4-bedroom, 2-bath Cape located on a quiet cul-de-sac in Plainfield. Situated on 0.81 acres, this home offers plenty of space while still being close to everything you need. Over the last few years, the home has seen extensive updates, including a new roof, vinyl siding, repaved driveway, farmer's porch, and front bedroom dormers, all completed

  Kelsie Griffin Wolfburg Kazantzis Real Estate, LLC

  8 Plainview Dr, Plainfield, CT 06374
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  /15

  $744,999

  New Construction $20K PRICE DROP

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

  106 Church St, Brooklyn, CT 06234

  Approved building lot on desirable street, property is on a shared driveway. TO BE BUILT: A 2,020 sqft., 3 bedroom, 2.5 bath colonial style home sits on a beautiful 2.6 acre lot. The kitchen features a tile backsplash, oversized island, stainless steel range hood, pantry cabinet, and quartz countertops. The living room flows from the kitchen creating an open feel. Hardwood flooring throughout the

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  106 Church St, Brooklyn, CT 06234
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  /35

  $539,000

  Open Sun 10AM - 11:30AM

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  88 Grand View Terrace, Brooklyn, CT 06234

  Welcome to 88 Grand View Terrace, where mid-century modern character meets a fresh, thoughtful renovation. Set on a half-acre in an established Brooklyn neighborhood, this beautifully updated home offers an open, light-filled layout with gorgeous hardwood floors, custom lighting and a spacious living/dining area featuring a classic brick fireplace. The brand-new kitchen complements the home's

  Jennifer Mahr RE/MAX Bell Park Realty

  88 Grand View Terrace, Brooklyn, CT 06234
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  /23

  $389,000

  • 3 Beds
  • 2 Baths
  • 1,610 Sq Ft

  222 Tower Hill Rd, Chaplin, CT 06235

  Beautifully set on 4.02 scenic acres in Chaplin, Connecticut, this charming 3-bedroom, 2-bath home offers the perfect blend of character, privacy, and versatility. Featuring approximately 1,600 square feet, the home showcases soaring vaulted ceilings, stunning exposed beams, and an inviting open-concept kitchen, dining, and living area filled with natural light. The finished lower level offers a

  Lisa Therecka Therecka & Associates LLC

  222 Tower Hill Rd, Chaplin, CT 06235
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  /40

  $200,000

  Coming Soon

  • 6 Beds
  • 1.5 Baths
  • 1,658 Sq Ft

  660 E Thompson Rd, Thompson, CT 06277

  Coming soon! Total privacy! Home needs work. Loads of potential! More info coming soon!

  Kim Synott eXp Realty

  660 E Thompson Rd, Thompson, CT 06277
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  /3

  $499,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,491 Sq Ft

  53 Litchfield Ave, Killingly, CT 06241

  ANOTHER REFINED LIVING EXCLUSIVE! To be built! A very rare NEW CONSTRUCTION home opportunity that offers 1,604 SF, attached 1 car garage, 3 large bedrooms, primary bedroom with it's own full bath and his & hers closets, 2 & 1/2 baths total, eat-in kitchen, dining room & main level laundry room. Large full basement. Well sought community. All New Homes Come with a Builder's Warranty! A new buyer

  Robert Letskus Platinum Associates

  53 Litchfield Ave, Killingly, CT 06241
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  /12

  $300,000

  $25K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,498 Sq Ft

  50 Pine Hill Rd, Sterling, CT 06377

  Attention investors, contractors, and handy buyers! This 4-bedroom, 2 full bathroom cape presents an outstanding opportunity to build equity and transform a property with incredible potential. While the home is in need of a full renovation, several major features are already in place, including a brand-new roof and solar system to help offset future energy costs. Inside, you'll find a spacious

  Amy Therrien The Neighborhood Realty Group

  50 Pine Hill Rd, Sterling, CT 06377
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  /40

  $369,900

  • 3 Beds
  • 1 Bath
  • 1,080 Sq Ft

  97 Kapitulik Rd, North Grosvenordale, CT 06255

  The inside of this home is adorable. The outside is an oasis of relaxation with absolute privacy. This is a well loved home that is in move-in condition. Cozy living room, updated kitchen, 3 Bedrooms on main floor. The lower level has a comfy family room, laundry and plenty of storage. The one car garage doubles as a workshop. So many great features, you won't be disappointed.

  Mae Lyons Stonehouse Real Estate Co., LLC

  97 Kapitulik Rd, North Grosvenordale, CT 06255
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  /30

  $859,900

  $90K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,437 Sq Ft

  9 Becola Rd, Thompson, CT 06277

  Rare opportunity to own 100 feet of beautiful pond frontage in Thompson, CT! From the moment you arrive, you'll fall in love with the peaceful setting, breathtaking water views, and the care that has gone into maintaining this home. Whether you're enjoying your morning coffee overlooking the lake, relaxing in the hot tub, or unwinding after a long day, this property offers a true sense of

  Chelsea Greene CR Premier Properties

  9 Becola Rd, Thompson, CT 06277
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  /39

  $2,500,000

  • 3 Beds
  • 4 Baths
  • 4,648 Sq Ft

  80 Bungay Hill Rd, Woodstock, CT 06281

  Welcome to this 80 acre Connecticut Estate, tucked into the rolling hills of Woodstock Ct. This exceptional 4,655 sq ft contemporary home offers a unique living experience with its own privately owned public FAA approved commercial grade airport. The property is a pilot's paradise, featuring a spacious hangar that not only accommodates multiple small planes and helicopters but also offers ample

  Cary Marcoux RE/MAX Bell Park Realty

  80 Bungay Hill Rd, Woodstock, CT 06281
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  /28

  $390,000

  $10K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,158 Sq Ft

  187 Tuckie Rd, North Windham, CT 06256

  Welcome to your own retreat! Perfectly positioned on a gorgeous, level 1 acre lot surrounded by mature trees, this beautifully maintained Cape offers the peaceful lifestyle you've been dreaming of. From the moment you arrive, you'll picture slow mornings spent on the charming front porch w/a cup of coffee and your favorite book, soaking in the quiet beauty that surrounds you. Out back, you'll

  Meghan Wininger Real Broker CT, LLC

  187 Tuckie Rd, North Windham, CT 06256
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  /40

  $649,900

  • 4 Beds
  • 2.5 Baths
  • 3,735 Sq Ft

  169 Woodward Rd, Brooklyn, CT 06234

  A rare blend of space, privacy, and character, this 4-bedroom, 2.5-bath Colonial is beautifully set on over 11 acres with mature trees, landscaped grounds, and a peaceful setting. From the moment you enter, the home makes an impression with a dramatic foyer featuring soaring 16 ft ceilings. The main level offers generous living spaces with hardwood floors, French doors, built-ins, fireplaces, and

  Josph Malone Coldwell Banker Realty

  169 Woodward Rd, Brooklyn, CT 06234
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  /37

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,574 Sq Ft

  23 Totem Pole Rd, Thompson, CT 06277

  Do not miss out on the rare opportunity to own this waterfront property on Quaddick Lake. Colonial style ~2600 sq ft house featuring 4 bedrooms with 3 full bathrooms, newly updated eat in kitchen with granite counter tops with breakfast bar, and stainless steel appliances. Laundry on main level. Formal dining room, living room, and large bonus room. Slider door takes you out to your very large

  Joseph Bonneau eXp Realty

  23 Totem Pole Rd, Thompson, CT 06277
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  /11

  $269,000

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

  1008 Windham Rd, South Windham, CT 06266

  Do you need an IN-LAW apartment? A Home business? May even be a possible 2 family. It's Possible with this home. Check the Town Hall for all possibilities. VERY LARGE single-family home with 5 bedrooms and 1 1/2 bathrooms. Nice yard, HUGE Dining room, Large Kitchen, a dramatic entrance to the second level!!! Two separate decks, bay windows with lots of natural light. Property needs some work, but

  Victoria Schroeder Kazantzis Real Estate, LLC

  1008 Windham Rd, South Windham, CT 06266
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  /39

  $574,900

  • 3 Beds
  • 2.5 Baths
  • 2,252 Sq Ft

  457 Kemp Rd, Hampton, CT 06247

  Tucked away on 10 private acres, this stunning log home offers the perfect blend of rustic charm and peaceful seclusion. Expertly crafted by Ward Cedar Log Homes of Maine, this exceptional residence showcases energy-efficient Northern White Cedar, renowned for its beauty and natural insulating properties. The inviting interior features custom hickory cabinetry with a spacious center island and

  Joanne Lukaskiewicz Wheaton Berkshire Hathaway NE Prop.

  457 Kemp Rd, Hampton, CT 06247
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  /19

  $219,000

  $19K PRICE DROP

  • 4 Beds
  • 1 Bath
  • 1,078 Sq Ft

  129 Walnut St, Willimantic, CT 06226

  Charming Antique Colonial - Prime Windham Location Step back in time and experience the warmth and character of this classic 1915 Antique Colonial, beautifully situated on a desirable corner lot in Windham. This inviting home offers four spacious bedrooms and one full bath, along with a generously sized living room perfect for relaxing or entertaining. The bright eat-in kitchen provides a

  Lisa Therecka Therecka & Associates LLC

  129 Walnut St, Willimantic, CT 06226
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  /40

  $6,950,000

  • 12 Beds
  • 9 Baths
  • 10,517 Sq Ft

  433 Wrights Crossing Rd, Pomfret Center, CT 06259

  Welcome to Bark Meadow Farm, a 127-acre legacy estate once cherished by the Gulden mustard family in CT's "Quiet Corner." The journey begins at a majestic entrance, where a striking allee of century-old maples stands alongside magnificent oaks nearing 200 years of age. This multi-generational compound offers 12 bedrooms & 7.2 bathrooms across three year-round residences. At the heart is the 1799

  Lisa Rollins Team Compass Connecticut, LLC

  433 Wrights Crossing Rd, Pomfret Center, CT 06259
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  /33

  $314,900

  • 3 Beds
  • 1 Bath
  • 1,175 Sq Ft

  142 Wilkinson St, Putnam, CT 06260

  Looking for a home with solid bones, a convenient location, and room to make it your own? This 3-bedroom, 1-bath ranch is tucked away in a residential neighborhood while still being just a short walk to the shops, restaurants, and charm of downtown Putnam. Inside, you'll find a welcoming fireplace anchoring the living room, an open kitchen and dining area that's perfect for everyday living and

  Rachael Johnston Johnston & Associates Real Estate, LLC

  142 Wilkinson St, Putnam, CT 06260
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  /34

  $500,000

  • 3 Beds
  • 2 Baths
  • 1,693 Sq Ft

  229 Woodstock Rd, Woodstock, CT 06281

  Proudly owned by the original owner, the Cape sites sweetly in East Woodstock. The original home, built in 1979, has had a nice mudroom and 2 car garage addition, as well as a pretty sunroom addition. The classic layout includes a kitchen with island, dining room with built-ins, and a spacious living room on the main level. There is also a full bath and main level bedroom. The second floor has

  Richard Loomis RE/MAX Bell Park Realty

  229 Woodstock Rd, Woodstock, CT 06281
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  /18

  $75,000

  • 2 Beds
  • 1 Bath
  • 450 Sq Ft

  25 Route 197, Woodstock, CT 06281

  Looking for your "Seasonal Home Away from Home" Look no further this cute as a button, privately situated park model. Fresh new updates and newly applied finishing touches, makes this unit able to just move on in and start enjoying the rest of the season. Just steps from the amenities. pool, pavilion, mini golf, cornhole field, basketball and short walk to the catch and release fishing pond.

  KAREN MILHEM Media Realty Group, Inc.

  25 Route 197, Woodstock, CT 06281
• 

  

  /33

  $585,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,768 Sq Ft

  1 Finn Ln, Plainfield, CT 06374

  Welcome home to this charming colonial nestled on a spacious beautifully maintained lot. Offering timeless curb appeal and plenty of room to spread out. Step outside to enjoy the expansive backyard perfect for entertaining, gardening, outdoor games or simply relaxing. Large unfinished room over garage offers more living space. This home has been lovingly cared for and is just waiting for you.

  Robin Keator Compass Connecticut, LLC

  1 Finn Ln, Plainfield, CT 06374
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  /33

  $280,000

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft

  18 Ballou St Unit 2, Putnam, CT 06260

  Welcome to Unit 2 at 18 Ballou Street in Putnam! This beautifully remodeled home offers a fresh, move-in-ready interior with a functional layout and plenty of additional space.The main level features hardwood floors throughout the living and dining areas, creating a bright and open space for everyday living and entertaining. The updated kitchen flows conveniently into the dining area and provides

  Megan Winslow Winslow Homes LLC

  18 Ballou St Unit 2, Putnam, CT 06260
• 

  

  /39

  $549,000

  • 3 Beds
  • 2 Baths
  • 1,802 Sq Ft

  13 Donovan Dr, Quinebaug, CT 06262

  Looking for New Construction but don't want to wait for it to be built? You have to check out this beautiful split-level built in 2024! Offering seamless contemporary design, energy-efficient comfort, and classic functionality, this truly move-in ready property leaves nothing left to do but unpack! The bright, open-concept main floor features abundant natural light, creating a warm and inviting

  Nicholas Pelletier Keller Williams Realty North Central

  13 Donovan Dr, Quinebaug, CT 06262
• 

  

  /32

  $789,000

  • 3 Beds
  • 2.5 Baths
  • 2,410 Sq Ft

  25 Colbridge Rd, Plainfield, CT 06374

  Welcome to 25 Colbridge Road, Plainfield, CT! Set on 5.6 private acres, this exceptional 3-bedroom, 2.5-bath cape offers 2,410 square feet of thoughtfully designed living space, combining timeless charm with modern amenities and endless potential. Step inside to discover beautiful birch hardwood floors, abundant natural light, and a spacious floor plan perfect for both everyday living and

  Greg Lehto William Pitt Sotheby's Int'l

  25 Colbridge Rd, Plainfield, CT 06374
• 

  

  /40

  $524,900

  Open Sun 11:30AM - 1PM

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

  92 New Rd, Moosup, CT 06354

  Welcome to 92 New Road, a well-cared-for property offering the space, privacy, and comfortable setting that makes it easy to feel at home. Set on a spacious lot in Plainfield, this home provides a peaceful rural atmosphere while remaining conveniently located near everyday amenities, shopping, dining, and major routes. Inside, you'll find a functional and inviting layout with plenty of natural

  Kenneth Townsend Coldwell Banker Realty

  92 New Rd, Moosup, CT 06354

Showing Results 121 - 160, Page 4 of 5