Windham County CT Homes for Sale

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  /40

  $499,900

  • 4 Beds
  • 2 Baths
  • 3,278 Sq Ft

  455 Westminster Rd, Canterbury, CT 06331

  This 2,200 sq. ft. Ranch style home has a gardeners dream oasis hiding in the backyard. Lovingly planned over the years, the backyard is filled with mature plantings, stamped concrete patio with gazebo, along with a waterfall featured Koi fish-pond. Home features refinished cabinets, stainless steel appliances, quartz counters, tile backsplash, vinyl plank flooring along with an eating/dining

  Ryan LaJoie Johnston & Associates Real Estate, LLC

  455 Westminster Rd, Canterbury, CT 06331
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  /40

  $365,000

  Open Sun 11AM - 1PM Coming Soon

  • 3 Beds
  • 2 Baths
  • 2,318 Sq Ft

  207 Summit St, Willimantic, CT 06226

  Step into a truly one-of-a-kind home where history, character, and creativity come together. Originally built circa 1892 as the historic Hilltop Hose Company No. 3 Firehouse, this remarkable property has been thoughtfully transformed into an eclectic single-family residence while honoring its architectural roots. The 1,000-square-foot first floor offers an expansive open layout with soaring

  Sue Esposito Home Selling Team

  207 Summit St, Willimantic, CT 06226
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  /40

  $1,200,000

  • 3 Beds
  • 2 Baths
  • 2,393 Sq Ft

  46 Cemetery Rd, Canterbury, CT 06331

  Exceptional opportunity to own a private country estate featuring a well-maintained Cape-style log home set on 41.83 acres of beautiful land. This charming residence offers 3 bedrooms and 2 full bathrooms, with a comfortable floor plan that includes a spacious family room and a recreation room in the lower level, providing plenty of space for relaxation, entertainment, and hobbies. Enjoy your

  Kevin Brignole Spaulding Realty Group, LLC

  46 Cemetery Rd, Canterbury, CT 06331
• 

  

  /2

  $1,295,000

  • Land
  • 12.8 Acres
  • $101,172 per Acre

  99 Azud Rd, Thompson, CT 06277

  Fully approved and shovel ready for 60 Multi Family Units! Affordable project can be developed in phases. Public sewer available, private well and 3 Phase Power. Close to the airline trail for hiking and cycling. Conveniently located restaurants and shopping. Close proximity to the casinos, Worcester, Providence, Boston and the Rhode Island and Ct Shoreline.

  Cary Marcoux RE/MAX Bell Park Realty

  99 Azud Rd, Thompson, CT 06277
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  /11

  $399,900

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

  115 Groveland Ave Unit 7, Putnam, CT 06260

  Development Opportunity! This is not simply a townhouse offering-it is a fully approved condominium development package on a private lot with views. The sale includes existing Townhouse Unit #7 with an attached garage, together with the associated land and development rights for eight additional units to be built. Fully engineered plans are available by request. Town approvals are in place,

  Jennie Kesselman Berkshire Hathaway NE Prop.

  115 Groveland Ave Unit 7, Putnam, CT 06260
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  /40

  $375,000

  • 4 Beds
  • 1 Bath
  • 3,070 Sq Ft

  1210 Route 169, Woodstock, CT 06281

  Better than ever is what could be said about this pristine 1760 antique colonial home! With Muddy Brook winding through the property and conserved land located next door, what you see is what you get here: peace and serenity on 2.54 acres in desirable Woodstock, CT! With a new cedar roof, a rebuilt and sealed chimney and all new sills put in place years ago this classic will continue sitting

  Stephanie Gosselin Berkshire Hathaway NE Prop.

  1210 Route 169, Woodstock, CT 06281
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  /26

  $439,000

  $4K PRICE INCREASE

  • 4 Beds
  • 2 Baths
  • 1,787 Sq Ft

  7 Devotion Rd, Windham, CT 06280

  Nestled in the peaceful, rural charm of Scotland, CT, this lovingly updated 9-room, 4-bedroom, 2-bathroom home delivers the perfect blend of comfort, character, and modern convenience. From the moment you arrive, you'll feel the embrace of home - and see endless opportunities for family life here. This home is ready for your life to unfold - from quiet weekday mornings to lively gatherings. Step

  Alexia Andrade US Asset Realty

  7 Devotion Rd, Windham, CT 06280
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  /2

  $295,000

  • Land
  • 2.79 Acres
  • $105,735 per Acre

  19 Knollwood Dr, Canterbury, CT 06331

  Level, lightly wooded commercial lot, next to retail plaza and Cumberland Farms. 2.79 acres. 535' road frontage. Zone VC Village Commercial. Both Well and Septic needed. $295,000. PERMITTED USES: Retail, Services, Office, Indoor Recreation, Motel... BY SPECIAL PERMIT: Church, School, Museum, Multi-use (mixed use)...

  Norm Peck Signature Properties of N.E.

  19 Knollwood Dr, Canterbury, CT 06331
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  /18

  $165,500

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft

  28 Circle Dr, Windham, CT 06256

  Completely remodeled 3-bedroom, 2-bath mobile home in North Windham! This move-in-ready home has been thoughtfully updated throughout and features a brand-new roof, new appliances, and modern finishes from top to bottom. The interior offers a bright and functional layout with updated flooring, refreshed kitchen and bathrooms, and comfortable living space. With recent upgrades throughout, this

  Arielle Ruffin Choice Realty

  28 Circle Dr, Windham, CT 06256
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  /38

  $454,900

  New Construction

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

  39 Valley View Dr Unit 14B, Killingly, CT 06241

  To Be Built!! Still time to customize your new home with the builder! Upscale condo's with all End Units. Stainless Steel Appliances included, Granite Counter Tops (upgrades available). Work closely with builder to make this house your new custom home in a beautiful community setting with walking trails around the Preserve. Fully furnished model unit on site to show. Leave the lawn care and

  Colleen Rybacki Brunet and Company Real Estate

  39 Valley View Dr Unit 14B, Killingly, CT 06241
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  /40

  $449,900

  • 3 Beds
  • 2 Baths
  • 1,944 Sq Ft

  29 Bingham Rd, Canterbury, CT 06331

  Move-in ready and beautifully maintained, this charming home offers 3 spacious bedrooms and 2 full bathrooms. The open floor plan creates a bright, welcoming living space that's perfect for everyday living and entertaining. The finished basement is an entertainer's dream, featuring a wet bar and a pool table that's included with the home. With thoughtful updates and plenty of space to relax and

  Laurie Hayes-Hagstrom On The Move Realty, LLC

  29 Bingham Rd, Canterbury, CT 06331
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  /38

  $699,000

  $76K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,855 Sq Ft

  60 Indian Spring Rd, Woodstock, CT 06281

  Perched above the shoreline of private Witches Woods Lake, this fully furnished waterfront retreat offers breathtaking water views, exceptional privacy, and a rare sense of tranquility. Brand-new multi-level TimberTech decks spanning roughly 800 square feet create an expansive outdoor living experience, perfectly positioned for entertaining, relaxing, or simply taking in the beauty of the lake

  Jennie Kesselman Berkshire Hathaway NE Prop.

  60 Indian Spring Rd, Woodstock, CT 06281
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  /40

  $389,000

  $11K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,544 Sq Ft

  217 Westford Hill Rd, Ashford, CT 06278

  Welcome to this oversized raised ranch offering the perfect blend of space, comfort, and functionality! Set on over an acre of land, this 4-bedroom home features a thoughtfully designed layout with room for everyone. The spacious primary suite is a true retreat, complete with a massive walk-in closet and an impressive en suite bathroom featuring a double vanity. Not to mention a 3 season room

  Amy Therrien The Neighborhood Realty Group

  217 Westford Hill Rd, Ashford, CT 06278
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  /2

  $39,900

  $10K PRICE DROP

  • Land
  • 23,522 Sq Ft
  • $73,889 per Acre

  47 Groveland Ave, Putnam, CT 06260

  Prime development opportunity in a convenient Putnam location at in incredible price. 2 lots available! Public water and sewer at the street. The property offers close access to shopping, restaurants, and I-395 for easy commuting to MA, CT and RI. No other engineering has been done.

  Jared Meehan RE/MAX Bell Park Realty

  47 Groveland Ave, Putnam, CT 06260
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  /40

  $429,900

  Open Sat 11AM - 12:30PM

  • 3 Beds
  • 1 Bath
  • 1,478 Sq Ft

  8 Whittemore Rd, North Grosvenordale, CT 06255

  Well-maintained Cape Cod-style home offering the perfect blend of timeless charm and thoughtful updates. This 3-bedroom, 1-bath home is nestled in an established neighborhood and features a brand-new kitchen with granite countertops, stainless steel appliances, updated cabinetry, and energy-efficient lighting. Additional improvements include a new roof, brand-new heating system, updated bathroom

  Jonathan Bolano eXp Realty

  8 Whittemore Rd, North Grosvenordale, CT 06255
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  /38

  $350,000

  Open Sat 10:30AM - 12:30PM Coming Soon

  • 3 Beds
  • 1 Bath
  • 1,764 Sq Ft

  38 Ayers Dr, Canterbury, CT 06331

  Move right into this well-maintained 3-bedroom, 1-bath ranch in the heart of Canterbury! Offering a total of 1,764 sq. ft. per town records (1008 up and 756 in lower level), this home features beautiful flooring on main level, fresh interior paint, and a spacious, well-kept kitchen with abundant cabinet storage. All kitchen appliances were replaced in July 2025. 3 standard size bedrooms and an

  Tina Luft Kazantzis Real Estate, LLC

  38 Ayers Dr, Canterbury, CT 06331
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  /13

  $170,000

  • Land
  • 3.4 Acres
  • $50,000 per Acre

  6 Broad St, Killingly, CT 06239

  This UNIQUE BEAUTIFUL 3.4-acre lot is truly a must see. Walk past the existing old barn, look to the right and then walk all the way down on the left, it is simply beautiful! Zoned - RESIDENTIAL HIGH DENSIITY there are so many possibilities for use. Single-family, two-family, and multi-family dwellings, Professional office or customary home occupation, uses allowed with special permit

  Belinda Culp Berkshire Hathaway NE Prop.

  6 Broad St, Killingly, CT 06239
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  /40

  $650,000

  • 2 Beds
  • 2.5 Baths
  • 2,393 Sq Ft

  511 Perrin Rd, Woodstock, CT 06281

  Perfect Countryside Elegance. Welcome to 511 Perrin Road, an exceptional country estate gracefully set atop a private 3.5-acre hillside in scenic Woodstock. A long paved driveway winds through picturesque grounds to this beautifully crafted home, where timeless architecture meets modern efficiency with 100% owned solar. Designed for effortless one-floor living, the residence features a luxurious

  John Downs Berkshire Hathaway NE Prop.

  511 Perrin Rd, Woodstock, CT 06281
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  /8

  $28,500

  $4K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 800 Sq Ft

  1032 N Main St Unit 3, Killingly, CT 06241

  Situated at 1032 N. Main U:3 in Killingly, CT, United States, this distinctive mobile home represents an established dwelling from 1970, offering an inviting opportunity for comfortable living. The residence features two dedicated bedrooms, providing private spaces conducive to rest and personal comfort. A single full bathroom is also present, equipped to serve daily needs with efficiency and

  Adam Bailey Next Level Realty

  1032 N Main St Unit 3, Killingly, CT 06241
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  /39

  $690,000

  Open Sat 11AM - 1PM

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

  71 Rhode Island Line Rd, Putnam, CT 06260

  Boasting an impressive amount of thoughtfully designed living space, this exceptional residence offers the perfect balance of luxury, and functionality just minutes from the Rhode Island and Massachusetts state lines! 3 bedrooms & 3 full baths. New roof & new expansion tank. This home is truly a private retreat. The main level showcases a beautifully appointed designer kitchen featuring granite

  Skyla Gagnon RE/MAX Bell Park Realty

  71 Rhode Island Line Rd, Putnam, CT 06260
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  /19

  $75,000

  • 2 Beds
  • 1 Bath
  • 450 Sq Ft

  25 Route 197 Unit 70, 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 Unit 70, Woodstock, CT 06281
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  /2

  $100,000

  • Land
  • 3.85 Acres
  • $25,974 per Acre

  70 Cutler Rd, Dayville, CT 06241

  lovely lot 3.5 acres lot great location builders opportunity

  Ned Murtha Coastal Properties Group

  70 Cutler Rd, Dayville, CT 06241
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  /31

  $699,000

  $121K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,344 Sq Ft

  81 Anderson Rd, Pomfret Center, CT 06259

  Welcome to this timeless 4 bedroom Contemporary Colonial estate offering over 3000 square feet of refined living space, nestled in the heart of scenic Pomfret. This stately home blends classic New England charm and privacy in the cul-de-sac neighborhood.Step inside this grand entryway to find rich wood flooring throughout lending warmth and sophistication to every room. The main level boasts a

  Kathy Rickey Signature Properties of N.E.

  81 Anderson Rd, Pomfret Center, CT 06259
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  /2

  $39,900

  $10K PRICE DROP

  • Land
  • 18,295 Sq Ft
  • $95,000 per Acre

  43 Groveland Ave, Putnam, CT 06260

  Prime development opportunity in a convenient Putnam location at in incredible price. Public water and sewer at the street. The property offers close access to shopping, restaurants, and I-395 for easy commuting to MA, CT and RI. A driveway has already been roughed in some years ago and the land was largely cleared 15+ years ago. No other engineering has been done.

  Jared Meehan RE/MAX Bell Park Realty

  43 Groveland Ave, Putnam, CT 06260
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  /2

  $35,000

  • Land
  • 1 Acre
  • $35,000 per Acre

  627-B Bailey Rd, Sterling, CT 06377

  Tucked away for privacy yet conveniently located near the Rhode Island line. Enjoy the peace and charm of a scenic, rural setting while still being within reach of nearby amenities. This lot of record provides a rare opportunity to find property in this price range. Whether you're looking to create a private retreat or a year-round residence, this property is full of potential.

  Cary Marcoux RE/MAX Bell Park Realty

  627-B Bailey Rd, Sterling, CT 06377
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  /2

  $104,000

  $20K PRICE DROP

  • Land
  • 3.35 Acres
  • $31,045 per Acre

  108 Church St, Brooklyn, CT 06234

  Beautiful approved lot on shared driveway, on desirable road.

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  108 Church St, Brooklyn, CT 06234
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  /34

  $239,000

  $20K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 3,243 Sq Ft

  259 Ference Rd, Ashford, CT 06278

  Rare value-add and redevelopment opportunity situated on 3.5 acres with over 3,200 square feet of existing space. Currently configured as a mixed-use commercial property, this expansive parcel offers strong potential for multifamily conversion, redevelopment, expansion, mixed-use investment, income-producing use, or possible additional building opportunities, subject to buyer due diligence and

  Michelle Gutierrez Social & Co Realty

  259 Ference Rd, Ashford, CT 06278
• 

  

  /40

  $775,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 2.5 Baths
  • 3,161 Sq Ft

  377 Pomfret Rd, Brooklyn, CT 06234

  Some homes are built to impress. Others are built to be remembered. Set amid 4.52 beautifully landscaped acres, this home is one of those rare New England properties where timeless architecture, exceptional craftsmanship, and thoughtful modern improvements come together in perfect balance. Inspired by the enduring character of a traditional Cape Cod, this meticulously maintained residence offers

  Darius Baturo Berkshire Hathaway NE Prop.

  377 Pomfret Rd, Brooklyn, CT 06234
• 

  

  /37

  $399,900

  • 2 Beds
  • 1 Bath
  • 1,575 Sq Ft

  290 Ference Rd, Ashford, CT 06278

  Investor? 2nd home? BnB? Lake Life! Welcome to Ashford CT. This home offers spectacular lake access and views. Sunrise to sunset enjoy the amenities of Lake Chaffee Beaches, kayaking, small boats, walks, fishing and much more! The 2009 home shines from head to toe. Enter through the cute front patio door with room to sit and enjoy the flowers and plantings. Hardwood floors, granite kitchen

  Roberta Cardinal RbRE, LLC

  290 Ference Rd, Ashford, CT 06278
• 

  

  /5

  $299,900

  • Land
  • 5.2 Acres
  • $57,673 per Acre

  1450 North Rd, Killingly, CT 06241

  Imagine building your dream home on more than 5 scenic acres and creating your own private residential helicopter estate. This unique property is home to Yankee Airstrip (CT13), an officially licensed Connecticut private airstrip, offering the opportunity for a future owner to pursue conversion to a private heliport, allowing you to build a custom home, construct a hangar, and enjoy the

  Scott Pempek Berkshire Hathaway NE Prop.

  1450 North Rd, Killingly, CT 06241
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  /33

  $400,000

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

  61 Soap St, Dayville, CT 06241

  This property offers exciting potential for both investors and owner-occupants. With additional buildable land and a river lining the rear of the property, there may be an opportunity to expand, build, or further develop the site, subject to zoning and municipal approvals. The existing layout also offers the flexibility to be converted into a spacious six-bedroom, three-bathroom single-family

  Aharon Cowen Roundtree Realty LLC

  61 Soap St, Dayville, CT 06241
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  /6

  $699,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,334 Sq Ft

  20 Hnath Rd, Ashford, CT 06278

  Stunning Custom Modern Farmhouse to Be Built in Ashford Meadow Estates, Ashfords Newest 6 lot subdivision featuring picturesque land in Eastern CT's quiet corner. Bold & Elegant with striking exterior finish options like timber frame porch accents, board & batten siding, metal roof accents & black Andersen windows. An interior designers dream! This open-concept floor plan with 9-foot ceilings

  Mark Massaro Coldwell Banker Realty

  20 Hnath Rd, Ashford, CT 06278
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  /35

  $299,000

  $16K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,818 Sq Ft

  158 Church St, Thompson, CT 06277

  Welcome to your dream home, where comfort meets tranquility! Nestled on a sprawling 1/2 acre, this captivating house offers the perfect blend of modern living and natural beauty. Step inside to discover a bright and airy living room that invites you to relax and unwind. The open floor plan seamlessly connects the living area to the dining space, creating an ideal environment for family gatherings

  Nick Baniukiewicz LAER Realty Partners

  158 Church St, Thompson, CT 06277
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  /34

  $579,900

  $20K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 3,190 Sq Ft

  15 Salmon Dr, Brooklyn, CT 06234

  This stunning 2005-built Colonial offer sophisticated living space, highlighted by gleaming hardwood floors that flow throughout the entire home. The heart of the house is an expansive kitchen featuring premium granite countertops, stainless steel appliances, and a gas stove, opening perfectly to a living area anchored by a cozy gas fireplace. Recent new renovated master bathroom never been use.

  Lucy Zhu Coastline Realty LLC

  15 Salmon Dr, Brooklyn, CT 06234
• 

  /2

  $129,900

  • Land
  • 2.34 Acres
  • $55,513 per Acre

  165 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

  165 Lisbon Rd, Canterbury, CT 06331
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  /29

  $399,900

  Open Sat 10AM - 11:30AM

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  49 Parsonage Rd, Hampton, CT 06247

  Welcome home to this beautiful, move-in ready Cape Cod nestled on a peaceful 1.80-acre lot. This charming home offers 3 bedrooms and 2 full bathrooms with a bright, open floor plan that seamlessly connects the kitchen, dining area, and living room-perfect for everyday living and entertaining. The spacious living room features vaulted ceilings and a cozy wood-burning stove, creating the perfect

  Michele Geragotelis RE/MAX Bell Park Realty

  49 Parsonage Rd, Hampton, CT 06247
• 

  

  /40

  $639,000

  • 4 Beds
  • 2.5 Baths
  • 3,036 Sq Ft

  26 Tatnic Hill Rd, Brooklyn, CT 06234

  This exceptionally cared for home on 2.78 serene acres in the lovely town of Brooklyn blends privacy, charm and rare versatility. This property contains flexible living options, and a layout perfect for creative use of space. With features such as radiant 4 season sunroom, and a flexible space perfect for an entertaining lounge, studio, whole house generator and many recent updates. Step outside

  Jen Pendergast William Raveis Real Estate

  26 Tatnic Hill Rd, Brooklyn, CT 06234
• 

  

  /39

  $625,000

  • 1 Bed
  • 1 Bath
  • 961 Sq Ft

  4 Loyola Rd, Woodstock, CT 06281

  This lakeside escape was completely redone in 2023. This beautifully updated 1-bedroom, 1-bath year-round home is nestled on the shores of private Quasset Lake in Woodstock. This direct waterfront property is an absolute paradise for entertaining, boating, water skiing, and fishing. Step inside to a bright interior that has been freshly painted top to bottom in a neutral color palette. The entire

  Steven Koleno Beycome of Connecticut

  4 Loyola Rd, Woodstock, CT 06281
• 

  /2

  $100,000

  • Land
  • 2.1 Acres
  • $47,619 per Acre

  834 Hampton Rd, Pomfret, CT 06230

  If you're looking for a rural location to build your home, this lot is an excellent choice! Beautiful countryside, surrounding farmland, and a peaceful, wooded environment, makes it ideal for those seeking this type of lifestyle. Close to the Airline trail and We Li Kit, this lot is close to many area amenities. Recent perc test performed. Ready to make your own! Buyer/Buyers agent to verify all

  Amy Brunet Brunet and Company Real Estate

  834 Hampton Rd, Pomfret, CT 06230
• 

  

  /30

  $289,000

  • 2 Beds
  • 2 Baths
  • 942 Sq Ft

  99 S Prospect St, Putnam, CT 06260

  Welcome to 99 S. Prospect Street, where timeless charm, everyday comfort, and room to grow come together in the heart of Putnam. This inviting 1930 ranch offers two bedrooms, two full baths, and a warm, welcoming layout filled with character. The sunlit living room features built in shelving and a cozy pellet stove, creating the perfect place to gather on chilly New England evenings. A spacious

  Erin Krajewski KW Legacy Partners

  99 S Prospect St, Putnam, CT 06260

Showing Results 161 - 200, Page 5 of 8