Windham, CT Homes

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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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  /40

  $3,000 per month

  • 4 Beds
  • 2 Baths
  • 2,022 Sq Ft
  • House for Rent

  169 Brayman Hollow Rd, Pomfret Center, CT 06259

  Welcome to 169 Brayman Hollow Rd in Pomfret CT! Tired of home searching in this volatile market? Stop searching and consider renting a single-family home. This stunning antique farmhouse has been updated over the years with modern mechanicals and aesthetic features. Four bedrooms, 2 full baths, living room, den, eat-in modern kitchen, dining room, laundry room on main floor, walk up attic for

  Brenda Chubbuck CR Premier Properties

  169 Brayman Hollow Rd, Pomfret Center, CT 06259
• 

  $429,125 Sold Jul 29, 2025

  • 1,557 Sq Ft
  • $276/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1972

  20 Windy Hill Rd, Hampton, CT 06247

  Charming updated Cape nestled on 2.06 acres of lush, park-like grounds. Enjoy peaceful outdoor living with meticulously landscaped gardens, waterfall fish pond, stamped stone patio, Trex deck, and a gazebo with electric. Inside, the home features a granite eat-in kitchen with stainless steel appliances, custom display shelves, and a matching cabinet. Pantry, Sunny double windows offer scenic

  Mary Collins Berkshire Hathaway NE Prop.

  20 Windy Hill Rd, Hampton, CT 06247
• 

  Est $466,188 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,690 Sq Ft

  44 Kennerson Reservoir Rd, Eastford, CT 06242

  44 Kennerson Reservoir Rd, Eastford, CT 06242
• 

  

  

  /35

  $350,000 Under Contract

  • 4 Beds
  • 2 Baths
  • 1,958 Sq Ft

  201 Main St, Hampton, CT 06247

  Best Offers due 7/7, Monday @ 7pm. Welcome to the heart of Hampton! Add together a beautiful country lot with perennial gardens, a charming 1949 Cape Home, a fully equipped in-law unit, plus an old horse run-in on 2.2 acres and you have the perfect blend of generational small-town character and modern convenience. The main home has 3 bedrooms and 1 full bath, and connects directly to the in-law

  

  Stephen Daly

  LPT Realty

  (860) 854-7908

  201 Main St, Hampton, CT 06247
• 

  

  /15

  $2,600 per month

  • 4 Beds
  • 2 Baths
  • 2,340 Sq Ft
  • House for Rent

  21 Page Rd, Pomfret Center, CT 06259

  Renovated historic antique 8 room 3 bedroom 2 bath home with a pond in Pomfret. beautiful site, abuts Airline Trail State Park for hiking and biking. Property shares driveway and 36 acres with one other house next door. Barn for storage, organic gardening and fishing allowed but no hunting. Whirlpool bath, decorative painting and tiling, granite countertops, period reproduction wallpapers,

  Dennis Duga Northeast Realty

  21 Page Rd, Pomfret Center, CT 06259
• 

  $453,655 Sold Jul 24, 2025

  • 1,989 Sq Ft
  • $228/SF
  • 28 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1800

  255 Killingly Rd, Pomfret Center, CT 06259

  Warm and inviting, this charming antique New England farmhouse blends 1800s character with modern conveniences. Set on 2.9 beautifully landscaped acres with scenic lighting and the peaceful sounds of Mashamoquet Brook, it's ideal for entertaining. Enjoy summers by the 16x32 propane-heated above-ground pool, relax under the covered patio with stunning stone fireplace, or gather in the large

  Mary Collins Berkshire Hathaway NE Prop.

  255 Killingly Rd, Pomfret Center, CT 06259
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  /50

  Est $416,798 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,344 Sq Ft

  109 Boston Turnpike, Eastford, CT 06259

  109 Boston Turnpike, Eastford, CT 06259
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  /3

  $239,900

  • 1 Bed
  • 1 Bath
  • 540 Sq Ft

  189 Chaplin Rd, Eastford, CT 06242

  Charming 1-Bedroom Cottage - Low-Maintenance Living This cozy 1-bedroom, 1-bath cottage offers simple and efficient living in a peaceful setting. With 540 square feet of space, it's the perfect option for a minimalist lifestyle, weekend getaway, or investment property. Inside, you'll find a comfortable layout with an open living area, full kitchen, and a nicely sized bedroom. Electric heat

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 916-6048

  189 Chaplin Rd, Eastford, CT 06242
• 

  $650,000 Sold Jul 23, 2025

  • 2,176 Sq Ft
  • $299/SF
  • 66 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1988

  128 Spaulding Rd, Brooklyn, CT 06234

  Down a quiet country road, past stone walls and open fields, you'll find a hidden gem waiting to welcome you home. Set on 5.4 private acres, this post-and-beam Cape blends timeless charm with thoughtful updates. Step through the front door into a soaring two-story foyer, where light pours through floor-to-ceiling windows and stunning ash wood floors guide you into the heart of the home. The

  Kristen Kaskela Berkshire Hathaway NE Prop.

  128 Spaulding Rd, Brooklyn, CT 06234
• 

  Est $500,410 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,388 Sq Ft

  180 Boston Turnpike, Pomfret Center, CT 06259

  180 Boston Turnpike, Pomfret Center, CT 06259
• 

  

  /39

  $485,000 Pending

  • 6 Beds
  • 3 Baths
  • 1,722 Sq Ft

  64 Tatnic Rd, Brooklyn, CT 06234

  Nestled on over 2 acres, this charming 4-bedroom, 2-bath Cape-style home is a perfect blend of comfort, functionality, and rural charm. The heart of the home features a spacious, open-concept kitchen and dining area with wood cabinetry, granite countertops, tile flooring, and skylight allowing the natural light in and creating an inviting atmosphere for everyday living and entertaining. Step

  

  Tina Lajoie

  William Raveis Real Estate

  (860) 784-7743

  64 Tatnic Rd, Brooklyn, CT 06234
• 

  $325,000 Sold Jul 17, 2025

  • 1,120 Sq Ft
  • $290/SF
  • 7 Days On Market

  • 4 Beds
  • 1 Bath
  • Built 1963

  31 Mason Hill Rd, Brooklyn, CT 06234

  Situated on a dead-end street, this home offers the ultimate in peace and hassle free living. The inviting covered porch with extra large windows (6 foot high) is the perfect spot to unwind, enjoy the sounds of birds and stay connected to nature. This property has been lovingly cared for by its owners for more than five decades and is a true testament to enduring quality and personal pride. From

  Joseph Rivers Larrow's Real Estate

  31 Mason Hill Rd, Brooklyn, CT 06234
• 

  Est $621,471 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,996 Sq Ft

  128 Orchard Hill Rd, Pomfret Center, CT 06259

  128 Orchard Hill Rd, Pomfret Center, CT 06259
• 

  

  /40

  $850,000

  • 3 Beds
  • 3.5 Baths
  • 2,502 Sq Ft

  187 Chaplin Rd, Eastford, CT 06242

  Rustic Luxury in Connecticut's Quiet Corner Nestled in the hills , this stunning custom log home blends rustic charm with modern comforts. Impeccably maintained, recent updates include a new roof, fresh exterior stain, and new garage doors (2023). Inside, the grand great room features soaring ceilings, exposed beams, and a floor-to-ceiling stone fireplace. The open-concept kitchen boasts custom

  

  Amy Rio

  Executive Real Estate Inc.

  (860) 530-5708

  187 Chaplin Rd, Eastford, CT 06242
• 

  $650,000 Sold Jul 14, 2025

  • 2,317 Sq Ft
  • $281/SF
  • 6 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1972

  170 Pomfret Rd, Brooklyn, CT 06234

  Charming Antique Cape on Scenic Route 169 Discover timeless New England charm in this beautifully maintained 3-bedroom, 2.5-bath antique Cape, ideally located off scenic Route 169 in picturesque Brooklyn. Set on a breathtaking parcel surrounded by classic stone walls, mature plantings, and sweeping open land, this property offers a rare blend of historic character and modern comfort. Step inside

  Cary Marcoux RE/MAX Bell Park Realty

  170 Pomfret Rd, Brooklyn, CT 06234
• 

  Est $396,113 Not Listed For Sale

  • 4 Beds
  • 1 Bath
  • 2,126 Sq Ft

  159 Hartford Rd, Brooklyn, CT 06234

  159 Hartford Rd, Brooklyn, CT 06234
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  /32

  $439,000

  • 3 Beds
  • 2.5 Baths
  • 1,189 Sq Ft

  35 Tripp Hollow Rd, Brooklyn, CT 06234

  Do not miss out on the opportunity to own this beautifully constructed raised ranch just built in 2021. This house features 3 bedrooms, 2.5 bathrooms and a 2 car garage. The lot is over 2 acres and offers plenty of privacy in a cozy rural setting. Very convenient location, just minutes away from restaurants, shopping plaza, and Route 6 for commuting. A few other tasteful features include granite

  Joseph Bonneau eXp Realty

  35 Tripp Hollow Rd, Brooklyn, CT 06234
• 

  $110,000 Sold Jul 14, 2025

  • Land
  • 17 Acres
  • $6,358 per Acre

  • 42 Days On Market

  0 Appell Rd, Brooklyn, CT 06234

  Possibilities on this lot with long views from the elevated site. ROW possibilities for access to the lot, which is easily walked and has possible 2 homesites. Buyer to do due diligence to determine access and possibility of subdivision.

  Cathy Duprey Duprey Real Estate, LLC

  0 Appell Rd, Brooklyn, CT 06234
• 

  Est $545,666 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,943 Sq Ft

  33 Estabrooks Rd, Hampton, CT 06247

  33 Estabrooks Rd, Hampton, CT 06247
• 

  

  /37

  $538,000

  • 3 Beds
  • 2.5 Baths
  • 1,624 Sq Ft

  125 E Old Route 6, Hampton, CT 06247

  A one of a kind, unique opportunity of 21 acres with both frontage on a quiet country road and on Providence Turnpike/Route 6. Currently used as a private residence with the enjoyment of using the land for hunting and other outdoor recreation activities. The approx. 1,000 of feet of frontage on Route 6, offers the potential to subdivide for residential lots or host one of the allowable businesses

  Lindsey L. Niarhakos RE/MAX One

  125 E Old Route 6, Hampton, CT 06247
• 

  $262,000 Sold Jul 07, 2025

  • 1,452 Sq Ft
  • $180/SF
  • 9 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1722

  21 Clinic Rd, Pomfret, CT 06259

  Welcome to 21 Clinic Road, a rare and charming find in the heart of Pomfret. Set on a picturesque 1.3 acre lot, this property offers not just one, bur two separate homes each with its own story and character. The main house dating back to 1722 is brimming with history and original details. Tucked away on the same lot is a cute one bedroom cottage built in 1985. It's perfect for guests, or multi

  Nicole Garbutt RE/MAX Bell Park Realty

  21 Clinic Rd, Pomfret, CT 06259
• 

  Est $418,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,848 Sq Ft

  196 Preston Rd, Brooklyn, CT 06234

  196 Preston Rd, Brooklyn, CT 06234
• 

  

  /22

  $599,000

  • 4 Beds
  • 2.5 Baths
  • 1,776 Sq Ft

  815 Mashamoquet Rd, Pomfret Center, CT 06259

  Beautifully renovated Ranch in Pomfret on 3 acres. From top, to bottom, this home has been updated and remodeled to a 4 bedroom, 2 and a half bath, bright home. From the 2 car attached garage, is the mudroom, which has access to the new deck. Into the kitchen, with new cabinets, granite counters, and bar seating. The primary bedroom is privately located in the rear of the house, with a new full

  Richard Loomis RE/MAX Bell Park Realty

  815 Mashamoquet Rd, Pomfret Center, CT 06259
• 

  $325,000 Sold Jul 02, 2025

  • 1,073 Sq Ft
  • $303/SF
  • 18 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1955

  79 Pomfret Rd, Brooklyn, CT 06234

  Beautiful Ranch home located on scenic route 169. Lovely 2 bedroom 1 bathroom home. Large living/dining room combo....Fireplace in the living room. Hardwood floors. Attached garage.

  Mark Benard Brunet and Company Real Estate

  79 Pomfret Rd, Brooklyn, CT 06234
• 

  Est $401,000 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,480 Sq Ft

  184 Tripp Hollow Rd, Brooklyn, CT 06234

  184 Tripp Hollow Rd, Brooklyn, CT 06234
• 

  

  /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
• 

  $655,000 Sold Jun 30, 2025

  • 2,932 Sq Ft
  • $223/SF
  • 6 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2005

  231 Paine Rd, Pomfret Center, CT 06259

  Nestled on a private 2.93-acre rear lot, this stunning home offers nearly 3,000 sq ft of well-designed living space with a bright and open floor plan, 9-foot ceilings throughout, and elegant crown molding. The spacious first-floor primary suite features a tray ceiling, walk-in closet, and a luxurious en-suite bath with both a soaking tub and separate shower. Enjoy relaxing on the charming

  Andrea Kazantzis, CCIM Kazantzis Real Estate, LLC

  231 Paine Rd, Pomfret Center, CT 06259
• 

  Est $330,500 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,632 Sq Ft

  196 Main St, Hampton, CT 06247

  196 Main St, Hampton, CT 06247
• 

  

  /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
• 

  $660,000 Sold Jun 30, 2025

  • 3,301 Sq Ft
  • $200/SF
  • 11 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1946

  98 Barrett Hill Rd, Brooklyn, CT 06234

  HIGHEST AND BEST IN BY TUESDAY 5/6 BY 3 PM Windsong Estate exemplifies luxury and splendor on Barrett Hill Road, one of the most prestigious addresses in Brooklyn CT. Discover the glorious blend of Brooklyn history and modern sumptuousness in this 5-acre retreat on one of the highest hills in the area. Secluded behind a chained driveway that is flanked by 100-year spring-blooming magnolia trees,

  Jennifer Jackson Berkshire Hathaway NE Prop.

  98 Barrett Hill Rd, Brooklyn, CT 06234
• 

  Est $369,422 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,344 Sq Ft

  220 Windham Rd, Brooklyn, CT 06234

  220 Windham Rd, Brooklyn, CT 06234
• 

  

  /16

  $696,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,609 Sq Ft

  7 Hyde Rd, Brooklyn, CT 06234

  Welcome to 7 Hyde Rd. Luxury Living awaits in this stunning new construction home in the Brooklyn Village District. Custom 4 bedroom, 2-1/2 bath home with a 2-car garage. Smart Home Technologies, stylish Cafe appliance package, central air conditioning, tankless water heater, propane heating system, impressive hardwood floors and custom staircase. This home features an inviting open-concept

  Randy Duquette The Neighborhood Realty Group

  7 Hyde Rd, Brooklyn, CT 06234
• 

  $1,215,000 Sold Jun 20, 2025

  • 7,136 Sq Ft
  • $170/SF
  • 59 Days On Market

  • 4 Beds
  • 6 Baths
  • Built 1988

  562 Taft Pond Rd, Pomfret Center, CT 06259

  Welcome to this magnificent 7,136 SF estate nestled on over 23 private acres in picturesque Pomfret, CT. Centrally located approximately an hour from Boston, Hartford, Providence, Springfield, and just 40 minutes to Worcester, this home offers a private escape with incredible conveniences. Upon entry, you're immediately captivated by the dramatic foyer featuring soaring 25'+ ceilings, elegant

  Jared Meehan RE/MAX Bell Park Realty

  562 Taft Pond Rd, Pomfret Center, CT 06259
• 

  Est $505,357 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,912 Sq Ft

  60 Pomfret Rd, Eastford, CT 06242

  60 Pomfret Rd, Eastford, CT 06242
• 

  

  /28

  $549,900 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,119 Sq Ft

  91 Pomfret Landing Rd, Brooklyn, CT 06234

  Located on a meandering back road of Brooklyn, CT, this 2119 SF 3 bedroom, 2.5 bath Raised Ranch is a gorgeous find! As you step inside, you'll be greeted by an open-plan living room, dining room, and kitchen area, featuring vaulted ceilings that add an airy, grand feel. The heart of this home is its kitchen, boasting stunning granite countertops you can pick from builders selections, with a

  Jared Meehan RE/MAX Bell Park Realty

  91 Pomfret Landing Rd, Brooklyn, CT 06234
• 

  $505,000 Sold Jun 20, 2025

  • 2,644 Sq Ft
  • $191/SF
  • 180 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1959

  13 Brooklyn Rd, Pomfret Center, CT 06259

  This beautiful updated 2700 sf. home on 1.87 acres is in a quiet country area of Pomfret. There is a master bedroom on the first floor and two additional bedrooms and a bath on the second floor. Outside enjoy the screened porch and large deck after a dip in the above ground pool or a relaxing soak on the hot tub. There is an attached in-law apartment with its own private entry. It has a full

  Margaret Young CR Premier Properties

  13 Brooklyn Rd, Pomfret Center, CT 06259
• 

  Est $655,000 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,501 Sq Ft

  289 Main St, Hampton, CT 06247

  289 Main St, Hampton, CT 06247
• 

  

  /38

  $449,900 Pending

  • 3 Beds
  • 2 Baths
  • 1,754 Sq Ft

  132 Wade Rd, Pomfret Center, CT 06259

  So much Privacy with this adorable Cape! Over 16 acres of seclusion! Glassed in Sunroom with Center Hot Tub for relaxation. Open living between Kitchen, Dining Room and Living Room, Wide Hardwood Floors, Breezeway, 3 Bedrooms, 2 full baths. Wood, coal and oil furnace! Two Bay Attached Garage. Minutes from Rt 44 for Easy Commute. Privacy! Privacy! Privacy!

  Rachel Sposato Berkshire Hathaway NE Prop.

  132 Wade Rd, Pomfret Center, CT 06259
• 

  $475,000 Sold Jun 16, 2025

  • 2,454 Sq Ft
  • $194/SF
  • 4 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2005

  15 Wolf Den Dr, Pomfret Center, CT 06259

  Welcome to 15 Wolf Den Road, a charming colonial set amidst the scenic beauty of Pomfret, CT. Offering 2,454 square feet of thoughtfully designed living space, this spacious home features three generously sized bedrooms, two full bathrooms, and expansive rooms perfect for family gatherings and entertaining. Set on a serene 1-acre lot, the property invites you to relax outdoors with a beautiful

  Robbie Greene Santos RE/MAX One

  15 Wolf Den Dr, Pomfret Center, CT 06259

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