Windham County CT Homes for Sale

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  /6

  $899,000

  • Land
  • 130.75 Acres
  • $6,876 per Acre

  0 Brooklyn Rd Unit 24124218, Canterbury, CT 06331

  GREAT OPPORTUNITY FOR RESIDENTIAL, FARM, or AGRICULTURE DEVELOPMENT ! 133 ACRES!! SOLD AS A PACKAGE ONLY WITH LISTING #24111912 TOTAL LAND BEING SOLD IS 133 ACRES(APPROX) and TOTAL ROAD FRONTAGE IS 350 FT(APPROX) WITH BOTH PARCELS COMBINED. BUYER TO PERFORM DUE DILIGENCE TO DETERMINE AVAILABLE LAND USE, ZONING REGULATIONS, UTILITIES AVAIL. CURRENT TAXES ARE FOR FORESTRY CLASSIFICATION

  Margaret Memoli Memoli&Memoli Real Estate,LLC

  0 Brooklyn Rd Unit 24124218, Canterbury, CT 06331
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  /2

  $65,000

  • Land
  • 12,196 Sq Ft
  • $232,143 per Acre

  64 Westcott Rd, Killingly, CT 06239

  Vacant land, undeveloped. Buyers to do due diligence.

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  64 Westcott Rd, Killingly, CT 06239
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  /8

  $99,900

  • Land
  • 2.17 Acres
  • $46,037 per Acre

  26 Bass Ln, Brooklyn, CT 06234

  Welcome to 26 Bass Lane. Total package consist of 8 lots consisting of 1.83 acres combined. Roughly 250 feet road frontage on Happy Lane while 26 Bass lane is the interior property sharing the road with just one other house. Property has been used for gardening and raising sheep. Mostly cleared dry, high and level land. Two sheds will remain. If you're looking for a quiet, spacious lot with lots

  Catherine Howard Berkshire Hathaway NE Prop.

  26 Bass Ln, Brooklyn, CT 06234
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  /28

  $679,900

  • 4 Beds
  • 2.5 Baths
  • 3,038 Sq Ft

  12 Red Oak Dr, Danielson, CT 06239

  Set back from the road, this spacious 4 bedroom, 2.5 bath Colonial offers the perfect blend of privacy, comfort, and summer fun with a beautiful 2.5 year old heated inground pool. A welcoming covered wraparound porch, paved drive, oversized 2 car garage, and dramatic two story foyer create a stunning first impression the moment you walk inside. The main level features an inviting eat in kitchen

  Kara Mazzola First Choice Realty

  12 Red Oak Dr, Danielson, CT 06239
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  /2

  $335,000

  • Land
  • 62.27 Acres
  • $5,380 per Acre

  0 Scotland Rd Unit 24160798, Chaplin, CT 06235

  **Builders Take Notice** This is a beautiful 62.273 acres with subdivision opportunities. A-2 Survey is available. Owner financing is available.

  Sherry Borgeson Berkshire Hathaway NE Prop.

  0 Scotland Rd Unit 24160798, Chaplin, CT 06235
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  /38

  $630,000

  • 5 Beds
  • 2.5 Baths
  • 3,215 Sq Ft

  1645 Route 169, Woodstock, CT 06281

  Perched on a hilltop in Woodstock, admired for decades for those who drove past on scenic Route 169, this single owner home is being offered for the first time. Thoughtfully built, and cared for, inside and out. The house looks modest from the road, however there is a surprising 3215sqft of living space. The original home has a few additions, including a generous sized family room with a

  Lynn Converse RE/MAX Bell Park Realty

  1645 Route 169, Woodstock, CT 06281
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  /40

  $1,695,000

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

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

  GRAND LEGACY ESTATE ON 291.6 ACRES w/REMODELED HISTORIC PRIMARY RESIDENCE & 2 ACCESSORY DWELLINGS! Gracefully spanning 2 contiguous parcels, this exceptional Eastern CT sanctuary embodies a rare convergence of early American heritage, refined country living, & remarkable land stewardship. Discreetly set along a quiet, town-maintained road, 93 & 90-94 Upton Road unfolds as a singular offering of

  Kiara Rusconi William Raveis Real Estate

  93 & 90-94 Upton Rd, Ashford, CT 06278
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  /2

  $90,000

  • Land
  • 4.25 Acres
  • $21,176 per Acre

  45 Brooklyn Rd, Canterbury, CT 06331

  Located on country Rd. Lightly treed lot. Perc tested and septic plans available.

  Maura Von Deck Von Deck Realty, LLC

  45 Brooklyn Rd, Canterbury, CT 06331
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  /39

  $599,900

  • 3 Beds
  • 2.5 Baths
  • 2,016 Sq Ft

  34 Courtney Ln, Sterling, CT 06377

  Set at the end of a quiet cul-de-sac in Sterling, this 3-bedroom, 2.5-bath colonial offers over 2,000 square feet of comfortable living space with the added bonus of a finished walkout basement. The main level features an expansive living room with a cozy propane fireplace, flowing seamlessly into the dining area and kitchen-creating an open, connected layout that's perfect for everyday living

  Sheena Ruggirello Real Broker CT, LLC

  34 Courtney Ln, Sterling, CT 06377
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  /2

  $335,000

  • Land
  • 34.6 Acres
  • $9,682 per Acre

  0 Route 171, Woodstock, CT 06281

  Spanning just over 37 acres this raw land parcel offers a picturesque pond and a wooded landscape, creating a versatile setting with a variety of potential uses. A rare opportunity to own a large tract of land in a lovely location.

  Nicole Gleason CR Premier Properties

  0 Route 171, Woodstock, CT 06281
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  /2

  $399,900

  Coming Soon

  • 4 Beds
  • 2 Baths
  • 1,947 Sq Ft

  61 Philip Ln, Dayville, CT 06241

  Available for the first time, this charming 4-bedroom, 2-bath Cape offers the perfect blend of warmth, character, and functionality. From the moment you arrive, you'll fall in love with the inviting feel and beautifully maintained lot, offering plenty of room to relax, entertain, or simply enjoy the outdoors. Inside, the home features an ideal layout with spacious living areas and flexible space

  Lexie Brunet Brunet and Company Real Estate

  61 Philip Ln, Dayville, CT 06241
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  /29

  $500,000

  New Construction Open Sat 11AM - 2PM

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

  99 Reilly Rd, Hampton, CT 06247

  Set back on 1.40 ACRES this 2026 Raised ranch is COMPLETED and can CLOSE ANYTIME! Last one available in a 3 lot subdivision. Brand new Stainless appliances in kitchen w/ white shaker cabinets, GRANITE and island. Vaulted ceiling open floor plan great for entertaining. BRIGHT Living room and dining area has slider to deck to enjoy your Fall evenings. Primary bedroom with its own bathroom, walkin

  Christine Johnson RE/MAX One

  99 Reilly Rd, Hampton, CT 06247
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  /40

  $310,000

  $15K PRICE DROP

  • 5 Beds
  • 2.5 Baths
  • 2,781 Sq Ft

  125 Mountain St, Willimantic, CT 06226

  Investors take notice! This home is a money maker. Whether you decide to owner-occupy this spacious home while rental income helps with the mortgage, or rent out both units, you can't go wrong. The living areas provide warm spaces perfect for relaxing or gathering with friends and family. The kitchens offer ample cabinet and counter space, making everyday cooking convenient and enjoyable. The

  Lisa Antrum KW Legacy Partners

  125 Mountain St, Willimantic, CT 06226
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  /20

  $289,000

  • 3 Beds
  • 1 Bath
  • 960 Sq Ft

  47 Texas Heights Rd, Plainfield, CT 06374

  RANCH HOME! Bring your vision and make this 3-bedroom, 1-bath ranch your own! Situated on a corner lot, this 960 sq ft home offers great potential with a full basement for added space or storage. Enclosed porch. With some repairs and updates, this property could shine again-ideal for investors, DIY enthusiasts, or first-time buyers looking for a project. Features a dirt driveway and solid bones

  Doug Taber Taber Realty, LLC

  47 Texas Heights Rd, Plainfield, CT 06374
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  /38

  $269,000

  • 2 Beds
  • 2 Baths
  • 1,053 Sq Ft

  104 Fairview St, Willimantic, CT 06226

  Welcome to 104 Fairview Street, Windham, CT! This beautifully maintained Cape is ready for its next owner. Filled with natural light and featuring updated windows, this inviting home offers 2 bedrooms, 2 full bathrooms, a spacious living room, dining area, and a functional kitchen designed for comfortable everyday living. Step outside and enjoy the spacious backyard, perfect for entertaining,

  Angela Espinoza CT Homes Real Estate

  104 Fairview St, Willimantic, CT 06226
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  /2

  $300,000

  • Land
  • 8.8 Acres
  • $34,091 per Acre

  100 Hubbard Hill Rd, Killingly, CT 06239

  Experience the quintessential beauty of this New England countryside on this breathtaking 8.8 acres. This property offers a rare sense of pastoral peace without sacrificing convenience. Located less than a quarter-mile from I-395, you can enjoy a quiet, rural lifestyle with seamless transit to Boston, Providence, and NYC right at your doorstep. This is also listed as part of 4 properties which

  Jill Pilgrim William Pitt Sotheby's Int'l

  100 Hubbard Hill Rd, Killingly, CT 06239
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  /39

  $594,900

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

  369 Thompson Rd, Thompson, CT 06277

  In the heart of Thompson Hill, step into history with the Jeremiah Olney House owned by the famous banker Jeremiah Olney in 1860, with its significant Greek Revival and Italianate features. This stunning 4-bed, 3.5-bath colonial farmhouse sits on nearly an acre of picturesque land and has been completely renovated. Overflowing with character, this home blends classic charm with modern

  Sheena Ruggirello Real Broker CT, LLC

  369 Thompson Rd, Thompson, CT 06277
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  /2

  $124,900

  • Land
  • 2.06 Acres
  • $60,631 per Acre

  161 Lisbon Rd, Canterbury, CT 06331

  EMILY'S VALLEY IN CANTERBURY, CT. SUPERIOR PARCELS IN A REPRODUCTION STYLE NEIGHBORHOOD OF HIGH VALUE HOMES. IT'S WORTH THE EFFORT TO BUILD A NEW QUALITY HOUSE TO YOUR OWN SPECIFICATIONS. QUALITY COUNTRY LIFESTYLE, PLENTY OF NEARBY GOODS AND SERVICES, REASONABLE TAXES AND IN TOWN SCHOOLS WITH A CHOICE OF GREAT AREA HIGH SCHOOLS (FULLY PAID BY THE TOWN).

  Derek Greene Derek Greene

  161 Lisbon Rd, Canterbury, CT 06331
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  /8

  $949,900

  Coming Soon

  • 5 Beds
  • 3 Baths
  • 2,246 Sq Ft

  651 Cook Hill Rd, Danielson, CT 06239

  Rare opportunity to own 78 breathtaking acres ideal for multi-generational living, farming, horses, recreation, a private compound/family homestead or even potential income-producing ventures. The beautifully updated circa-1920 farmhouse offers 5 bedrooms, 3 full baths, and a flexible office/bonus room with closet. Recent renovations blend modern convenience with timeless farmhouse charm and

  Joseph Bonneau eXp Realty

  651 Cook Hill Rd, Danielson, CT 06239
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  /14

  $399,000

  • 11 Beds
  • 2.5 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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  /33

  $274,900

  Coming Soon

  • 3 Beds
  • 1 Bath
  • 984 Sq Ft

  519 Brooklyn Rd, Canterbury, CT 06331

  Charming antique cottage nestled along a bucolic country road in Canterbury, Connecticut. Set on a generous 2.14-acre partially wooded lot, this inviting 3-bedroom, 1 full bath home offers 984 square feet of comfortable living space filled with character and warmth. A sweet front porch welcomes you home and provides the perfect spot to relax and take in the peaceful country surroundings. Freshly

  Cyrille Bosio Berkshire Hathaway NE Prop.

  519 Brooklyn Rd, Canterbury, CT 06331
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  /21

  $699,000

  • Land
  • 84.5 Acres
  • $8,272 per Acre

  61 Deerwood Dr, Killingly, CT 06239

  51 fully approved 55+ housing units to be built in Phases III & IV of the Briarwood Falls development property. within minutes of Killingly Center & Killingly Commons, and a half-hour to the casinos. All utilities and full site plans including architectural drawings for 1,250, 1,450, and 1,600 square foot designs of the first two phases are available. A 2025 revised estimate for the road &

  Maxwell Lyman Lyman Real Estate

  61 Deerwood Dr, Killingly, CT 06239
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  /3

  $150,000

  • Land
  • 22.8 Acres
  • $6,579 per Acre

  0 W Thompson Rd Unit 24146108, Thompson, CT 06255

  0 Thompson Road offers a picturesque 22.8 acre mixed-use commercial land opportunity located in the BDD (Business Development District) zone, allowing for energy storage, agricultural operations, multi-family housing (special permit), and light manufacturing, subject to Town Planning & Zoning approval. Gentle Slopping Bordered by the French River and North Grosvenordale Pond, the site includes

  Michael Collins Berkshire Hathaway NE Prop.

  0 W Thompson Rd Unit 24146108, Thompson, CT 06255
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  /2

  $399,900

  • Land
  • 8.29 Acres
  • $48,239 per Acre

  0 West Pkwy, Plainfield, CT 06374

  Positioned within a well-established industrial park, this 8+ acre parcel offers a prime opportunity for industrial development just 1/2 mile from Interstate 395, providing excellent regional access for transportation, logistics, and distribution operations. The property's location allows for efficient connectivity to major Northeast markets, making it ideal for manufacturing, warehousing,

  Androula Kazantzis KAZANTZIS ANDROULA

  0 West Pkwy, Plainfield, CT 06374
• 

  /2

  $400,000

  New Construction

  • 1 Bed
  • 1 Bath
  • 644 Sq Ft

  6 Indian Run Dr, Thompson, CT 06277

  Similar to be built. Charming Craftsman-style home offering efficient, low-maintenance living! This thoughtfully designed 644 sq. ft. home features 1 bedroom and 1 full bathroom with a bright, open floor plan. Large windows fill the space with natural sunlight, creating a warm and inviting atmosphere. The kitchen and living areas flow seamlessly, perfect for comfortable everyday living. Enjoy

  Cary Marcoux RE/MAX Bell Park Realty

  6 Indian Run Dr, Thompson, CT 06277
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  /32

  $599,000

  • 4 Beds
  • 2 Baths
  • 2,420 Sq Ft

  26 Quaddick Town Farm Rd, Thompson, CT 06277

  Welcome to 26 Quaddick Town Farm Road, a stunningly revitalized residence where modern luxury meets tranquil country living. Spanning 2,420 SF on a lush 1.14-acre lot, this home has been remodeled from top to bottom, offering the pristine feel of new construction with the character of an established estate. Step across a bright open floor plan designed for effortless living with stained hardwood

  Michael Disla eXp Realty

  26 Quaddick Town Farm Rd, Thompson, CT 06277
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  /4

  $60,000

  • Land
  • 26,571 Sq Ft
  • $98,361 per Acre

  81 Deerfield Dr, Sterling, CT 06377

  Discover this beautiful 0.61-acre lot-ready and waiting for your dream build. Tucked away on a private road in Sterling, CT, this property offers the perfect opportunity to create your own peaceful retreat. Whether you're envisioning a custom home or a quiet getaway, this slice of heaven provides the privacy and space you've been looking for.

  Kristopher Tramont Real Broker CT, LLC

  81 Deerfield Dr, Sterling, CT 06377
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  /20

  $164,900

  • Land
  • 2.3 Acres
  • $71,696 per Acre

  49 Stone Rd, Killingly, CT 06241

  LOCATION LOCATION LOCATION!! 2.3 acre building lot with over 295' of water frontage on the Five Mile River! Build your dream home on this tranquil park like setting. The pictures don't do it justice! This location is surrounded by high end custom homes, sitting on a quiet country road, yet still close to all major amenities and routes such as I-395, Rte 44, and Rte 101.

  Dale Bunn Riverview Realty, LLC

  49 Stone Rd, Killingly, CT 06241
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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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  /3

  $39,000

  • Land
  • 13,068 Sq Ft
  • $130,000 per Acre

  0 Oak Dr, Woodstock, CT 06281

  The closest you can be to the waterfront, without the waterfront price! HERE'S YOUR CHANCE AT AN AFFORDABLE BUILDING SITE WITH WATER RIGHTS TO BUNGAY LAKE. SWIM, FISH, AND BOAT OR COME SIT BY THE WATER AND RELAX. 20 min to Day Kimball Hospital, close to 84 & I90, easy access to Worcester and Boston. 4 Oak Dr was sold for 490k in 2024 (new construction on 0.3 Acres).

  Elizabeth Vernes Find Real Estate LLC

  0 Oak Dr, Woodstock, CT 06281
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  /39

  $999,000

  • 3 Beds
  • 2 Baths
  • 1,808 Sq Ft

  254 Beaver Hill Rd, North Windham, CT 06256

  Hidden Acres is a rare opportunity to own 70+ secluded acres where rustic charm, craftsmanship, and modern functionality come together. Tucked away in a private setting, this extraordinary farm features a 14,400-square-foot equestrian facility with a 12-stall barn and indoor riding arena, ideal for horse enthusiasts, trainers, or those seeking a premier recreational property. A heated

  Lori Vogel William Raveis Real Estate

  254 Beaver Hill Rd, North Windham, CT 06256
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  /25

  $450,000

  • 3 Beds
  • 2.5 Baths
  • 2,240 Sq Ft

  83 Dodge Rd, Woodstock, CT 06281

  Set in the charming town of Woodstock and minutes from the Massachusetts line, this 3-bedroom, 2.5-bath home offers space, flexibility, and a layout ideal for both everyday living .The home includes two primary suites- rare find! Inside, you'll find a spacious living room with vaulted ceilings and a propane fireplace, creating a warm and inviting focal point. The large kitchen features abundant

  Skyla Gagnon RE/MAX Bell Park Realty

  83 Dodge Rd, Woodstock, CT 06281
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  /3

  $199,000

  • Land
  • 16.08 Acres
  • $12,376 per Acre

  110 Church St, Brooklyn, CT 06234

  Approved building lot on shared driveway. Desirable location.

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  110 Church St, Brooklyn, CT 06234
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  /3

  $349,500

  • Land
  • 1.14 Acres
  • $306,579 per Acre

  423 Providence Rd, Brooklyn, CT 06234

  * City Water, Septic, and Gas * Located across the street from Walmart Supercenter * Traffic Count: 14,900 * Conceptual Plans for Various Uses * Zoning Uses: Retail, Self Storage/Contractor Bays, Apartments/Condos * Zone: PC * Nearby Tenants: McDonald's, CVS, NAPA, Advance Auto Parts, Dollar Tree, Ocean State Job Lot, Dunkin', KFC, AutoZone, & (coming soon) Tractor Supply

  Sam Lyman Samuel Lyman, Broker

  423 Providence Rd, Brooklyn, CT 06234
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  /40

  $1,450,000

  • 3 Beds
  • 5.5 Baths
  • 6,394 Sq Ft

  1374 Route 171, Woodstock Valley, CT 06282

  Set on 10.3 private acres in desirable Woodstock Valley, "Blue Heron Glade" offers a rare blend of privacy, natural beauty, and thoughtfully designed living spaces in Connecticut's Quiet Corner. A long private driveway with a charming cobblestone bridge leads to this exceptional property surrounded by stone walls, abundant wildlife, and a large pond frequented by blue herons. The main residence

  Kristen Kaskela Berkshire Hathaway NE Prop.

  1374 Route 171, Woodstock Valley, CT 06282
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  /39

  $520,000

  Open Sun 1PM - 2:30PM $29K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,150 Sq Ft

  101 Child Hill Rd, Woodstock, CT 06281

  Step back in time with this one-of-a-kind 1830 Greek Revival farmhouse, offering 2,150 sq ft of character and charm on a picturesque 0.90-acre lot surrounded by farm land. Just down the hill from historic Woodstock Hill and the Academy, this setting is as scenic as it is convenient. Inside, wide plank floors and distinctive windows frame beautiful country views, while the front entry showcases

  Kristen Kaskela Berkshire Hathaway NE Prop.

  101 Child Hill Rd, Woodstock, CT 06281
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  /26

  $510,000

  • 4 Beds
  • 2 Baths
  • 2,090 Sq Ft

  74 Lake Woods Ln, Ashford, CT 06278

  Nestled on a private cul-de-sac in a peaceful country setting, this beautifully maintained 4-bedroom, 2-bath home offers the perfect blend of privacy, comfort, and convenience with easy access to both Hartford and Boston. Built in 2018 and set on 3 picturesque acres surrounded by conservation land, stone walls, and wooded walking paths with a short distance to Ashford Lake, this 2,090 square foot

  Michael Deyorio CR Premier Properties

  74 Lake Woods Ln, Ashford, CT 06278
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  /30

  $325,000

  Open Sun 12AM - 2PM

  • 2 Beds
  • 2.5 Baths
  • 1,588 Sq Ft

  65 Perry St Unit 111, Putnam, CT 06260

  Desirable location, smart updates, and peaceful backyard-This 2 bedroom, 2.5 bath end-unit condo checks all the boxes. Enjoy new energy efficient windows, fresh carpeting, updated flooring and refreshed bathrooms. This home has more privacy than most condos, plus the convenience of an attached garage. Located close to major routes, great restaurants, shopping, and medical facilities. It's easy

  Jen Pendergast William Raveis Real Estate

  65 Perry St Unit 111, Putnam, CT 06260
• 

  

  /39

  $454,900

  New Construction

  • 3 Beds
  • 2.5 Baths
  • 1,710 Sq Ft

  37 Valley View Dr Unit 14A, Killingly, CT 06241

  Upscale new-construction end-unit condo featuring 3 bedrooms, 2.5 baths, and a 1-car garage. This beautifully designed home offers an open-concept layout, modern finishes, and abundant natural light throughout. The spacious walk-out basement provides additional living or storage potential. Located on a quiet cul-de-sac, this desirable end unit combines privacy, comfort, and convenience in a

  Colleen Rybacki Brunet and Company Real Estate

  37 Valley View Dr Unit 14A, Killingly, CT 06241
• 

  

  /34

  $874,900

  • 4 Beds
  • 3.5 Baths
  • 2,114 Sq Ft

  1555 Riverside Dr, North Grosvenordale, CT 06255

  Tucked away on 26.6 peaceful acres right on the Massachusetts border, this one-of-a-kind property offers privacy, space, and endless possibilities. This 4-bedroom, 3.5-bath home features a spacious layout with extra space above the garage, a finished basement perfect for entertaining or additional living quarters, and so much more. Outside, you'll find a separate 3-bay metal garage ideal for

  Courtney Ravenelle RE/MAX Bell Park Realty

  1555 Riverside Dr, North Grosvenordale, CT 06255

Showing Results 81 - 120, Page 3 of 7