Windham, CT Homes

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  /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
• 

  Explore Eastford

• 

  $450,000 Sold Jun 30, 2025

  • 2,328 Sq Ft
  • $193/SF
  • 51 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  75 County Rd, Eastford, CT 06242

  Welcome home to this beautifully maintained 3-bedroom, 2.5-bath Farm House, Colonial, built in 2004, offering 1,664 square feet of living space with a bonus 664 square feet of finished basement. Nestled on a large, level lot, this home features a fenced-in backyard, a spacious deck, and a classic covered farmers porch. Inside, you'll love the open-concept layout featuring hardwood floors, a

  Lauren Heidelberger Berkshire Hathaway NE Prop.

  75 County Rd, Eastford, CT 06242
• 

  Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,002 Sq Ft

  72 Ashford Rd, Eastford, CT 06242

  72 Ashford Rd, Eastford, CT 06242
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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
• 

  $325,000 Sold Jun 03, 2025

  • 1,574 Sq Ft
  • $206/SF
  • 50 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1946

  17 Eastford Rd, Eastford, CT 06242

  Charming Eastford Property with Barn, Garage & small Pond. Don't miss out on this fantastic property in a convenient yet peaceful location! Just 10 minutes from Vanilla Bean Cafe in Pomfret and 20 minutes from downtown Killingly. This home offers the perfect blend of accessibility and seclusion with minimal traffic. Solar package contract will be uploaded, seller has not paid an electric bill

  Missy Greene eXp Realty

  17 Eastford Rd, Eastford, CT 06242
• 

  Est $41,115 Not Listed For Sale

  37 Weeks Rd, Eastford, CT 06242

  37 Weeks Rd, Eastford, CT 06242
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  /12

  $800,000

  • Land
  • 153 Acres
  • $5,229 per Acre

  Lot 0 Kozey Rd, Eastford, CT 06242

  Tranquil 153-Acre Parcel Abutting Natchaug & Yale Forests - A Rare Opportunity in Nature's Embrace Discover a breathtaking 153-acre parcel of unspoiled land offering unmatched peace, privacy, and natural beauty. Nestled in the quiet corner of the Last Green Valley in Connecticut's countryside, this extraordinary property directly borders both Natchaug State Forest, Yale Forest and the Old

  

  Elizabeth Scranton

  Kazantzis Real Estate, LLC

  (860) 846-3950

  Lot 0 Kozey Rd, Eastford, CT 06242
• 

  $470,000 Sold May 30, 2025

  • 1,558 Sq Ft
  • $302/SF
  • 4 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1986

  106 Kennerson Reservoir Rd, Eastford, CT 06242

  Charming Post & Beam with water views. Nestled on a quiet cul-de-sac, with its distinctive craftsmanship, blending character with modern comfort. Enjoy sitting in screened porch or deck on a lovely summer evening, just a short walk to public boat launch, perfect for nature lovers and outdoor enthusiasts. Inside, you'll find two bedrooms, each with their own full bath, along with a convenient half

  Amy Archambault CR Premier Properties

  106 Kennerson Reservoir Rd, Eastford, CT 06242
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  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
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  /14

  $199,999

  • 2 Beds
  • 2 Baths
  • 2,713 Sq Ft

  211 Old Colony Rd, Eastford, CT 06242

  This unique property in Eastford, CT, built in 1821, offers over 2700 square feet of living space and is brimming with historical charm and potential. While it requires extensive renovation to restore its former glory, the home boasts original features such as wide-plank hardwood floors and built ins. The spacious layout includes multiple rooms that can be reimagined for modern living. This

  Brittany Russell Tier 1 Real Estate

  211 Old Colony Rd, Eastford, CT 06242
• 

  $328,900 Sold May 22, 2025

  • 1,167 Sq Ft
  • $282/SF
  • 48 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2025

  3 Nahaco Hill Ln, Eastford, CT 06242

  WELCOME to Eastford where there are BEAUTIFUL 2025 STAND-ALONE Condos on a dead end cul de sac. ONE YEAR WARRANTY and ONE LEVEL LIVING w/NO Maintenance! STAINLESS appliances, WHITE shaker cabinets, ISLAND w/ GRANITE counters and VAULTED ceiling with OPEN FLOOR PLAN to BRIGHT living room w/ SLIDER to patio. LARGE Primary bedroom w/HUGE closet and Primary bathroom with shower and GRANITE VANITY.

  Christine Johnson RE/MAX One

  3 Nahaco Hill Ln, Eastford, CT 06242
• 

  Est $339,905 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,513 Sq Ft

  123 Ashford Rd Unit 6, Eastford, CT 06242

  123 Ashford Rd Unit 6, Eastford, CT 06242
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  /40

  $575,000

  • 4 Beds
  • 2.5 Baths
  • 4,538 Sq Ft

  89 John Perry Rd, Eastford, CT 06242

  Welcome to the Benjamin Bosworth House, affectionately known locally as "The Castle." This extraordinary Federal-style home, Circa 1796, blends timeless craftsmanship with historic character. Set on 3 private acres, this 4,538 sq ft estate features 4 bedrooms, 2.5 baths, and 11 fireplaces across a thoughtfully designed layout. Notable architectural details include hand-carved mantels, doors, and

  Mary Collins Berkshire Hathaway NE Prop.

  89 John Perry Rd, Eastford, CT 06242
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  $520,000 Sold May 21, 2025

  • 1,619 Sq Ft
  • $321/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  38 Hall Rd, Eastford, CT 06242

  Discover your own private mountain sanctuary nestled high in the Woodstock Valley, overlooking the picturesque Bigelow Park. Imagine waking to breathtaking panoramic views each morning from your 7.55-acre hillside estate, perched at an elevation of 850 feet. This idyllic retreat boasts Lost Pond Brook with brook trout, meandering along its lower boundary. More than just a house, this is a haven

  Rachael Gifford The Neighborhood Realty Group

  38 Hall Rd, Eastford, CT 06242
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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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  /24

  $425,000

  • 5 Beds
  • 3.5 Baths
  • 5,400 Sq Ft

  41 Millbridge Rd, Eastford, CT 06242

  Nestled in the tranquil corner of Eastford, CT, this expansive 5-bedroom, 3.5-bathroom ranch offers a serene escape on a generous 8.7-acre lot. With a two-car attached garage and a sprawling wrap-around porch, this home invites you to enjoy the peaceful outdoors and picturesque surroundings. As you step inside, you're greeted by soaring cathedral ceilings and an open floor plan that seamlessly

  Melissa Guerrero William Pitt Sotheby's Int'l

  41 Millbridge Rd, Eastford, CT 06242
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  $395,000 Sold Apr 30, 2025

  • 1,065 Sq Ft
  • $371/SF
  • 60 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1974

  300 Kennerson Reservoir Rd, Ashford, CT 06278

  BEAUTIFUL BRAND NEW ROOF!!! Come and tour this charming 3 bedroom, 2 full bath Cape in Ashford. Surrounded by open farmland on a quiet country road. Enter through a sweet mudroom into your kitchen with new cabinets, an island, newer appliances and granite countertops. A lovely dining area with slider out to the backyard awaits your personal touch! There is a main level bedroom and full bath.

  Amy Archambault CR Premier Properties

  300 Kennerson Reservoir Rd, Ashford, CT 06278
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  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
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  /21

  $328,900 New Construction

  • 1 Bed
  • 2 Baths
  • 1,167 Sq Ft

  6 Nahaco Hill Ln, Eastford, CT 06242

  WELCOME to Eastford where there are BEAUTIFUL 2025 STAND-ALONE Condos on a dead end cul de sac where you Can VIEW 2 MODELS. ONE YEAR WARRANTY and ONE LEVEL LIVING w/NO Maintenance! STAINLESS appliances, WHITE shaker cabinets, ISLAND w/ GRANITE counters and VAULTED ceiling with OPEN FLOOR PLAN to BRIGHT living room w/ SLIDER to patio. LARGE Primary bedroom w/HUGE closet and Primary bathroom with

  Christine Johnson RE/MAX One

  6 Nahaco Hill Ln, Eastford, CT 06242
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  $55,000 Sold Apr 25, 2025

  • Land
  • 2.06 Acres
  • $26,699 per Acre

  • 100 Days On Market

  41 Weeks Rd W, Eastford, CT 06242

  Escape to the serenity of this peaceful, sloping lot, nestled in the beautiful countryside of Eastford, CT. Surrounded by nature, this lightly wooded parcel offers the perfect spot for your dream home, retreat, or outdoor getaway. The lot is situated in a quiet, rural area, providing privacy and tranquility while still being close to local amenities and attractions. Whether you seek a quiet place

  Vivian Kozey CR Premier Properties

  41 Weeks Rd W, Eastford, CT 06242
• 

  Not Listed For Sale

  66 Weeks Rd W, Eastford, CT 06242

  66 Weeks Rd W, Eastford, CT 06242
• 

  

  /21

  $328,900 New Construction

  • 1 Bed
  • 2 Baths
  • 1,167 Sq Ft

  5 Nahaco Hill Ln, Eastford, CT 06242

  WELCOME to Eastford where there are BEAUTIFUL 2025 STAND-ALONE Condos on a dead end cul de sac this one is ***TO BE BUILT- Can VIEW MODEL***. ONE YEAR WARRANTY and ONE LEVEL LIVING w/NO Maintenance! STAINLESS appliances, WHITE shaker cabinets, ISLAND w/ GRANITE counters and VAULTED ceiling with OPEN FLOOR PLAN to BRIGHT living room w/ SLIDER to patio. LARGE Primary bedroom w/HUGE closet and

  Christine Johnson RE/MAX One

  5 Nahaco Hill Ln, Eastford, CT 06242
• 

  $960,000 Sold Apr 18, 2025

  • 3,859 Sq Ft
  • $249/SF
  • 124 Days On Market

  • 3 Beds
  • 4 Baths
  • Built 2017

  32 Pilfershire Rd, Eastford, CT 06242

  Where Luxury Just Got Bigger and Better: Now offering 3 bedrooms, 4 full baths, and even more heated living space, this remarkable estate takes rustic-meets-modern living to the next level! Set on over 5 manicured acres bordering thousands of acres of Connecticut state forest, it welcomes you with a grand, tree-lined driveway, exquisite landscaping, stonework, and irrigation. Inside, an

  Jennie Kesselman Berkshire Hathaway NE Prop.

  32 Pilfershire Rd, Eastford, CT 06242
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  Est $97,959 Not Listed For Sale

  127 Lakeside Dr, Ashford, CT 06278

  127 Lakeside Dr, Ashford, CT 06278
• 

  /2

  $87,500 Pending

  • Land
  • 5 Acres
  • $16,386 per Acre

  Lot 4A Weeks Rd, Eastford, CT 06242

  5.34 acres located on a quiet country road, offering a mix of open space and wooded areas. This private setting is ready for your dream home. Perc tested in 2002. A great opportunity to enjoy peaceful, rural living.

  Tammy Arute Arute Realty Group LLC

  Lot 4A Weeks Rd, Eastford, CT 06242
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  $310,000 Sold Apr 17, 2025

  • 1,932 Sq Ft
  • $160/SF
  • 48 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1900

  54 Westford Rd, Eastford, CT 06242

  Step back in time and envision the possibilities with this classic home brimming with character and awaiting your personal touch. Nestled in a picturesque setting in Eastford, this timeless 1900's property sits on a beautiful corner lot, enhanced by charming stonework that adds to its character and appeal. With 3.75 acres of serene countryside, this home is perfect for entertaining family and

  Vivian Kozey CR Premier Properties

  54 Westford Rd, Eastford, CT 06242
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  Est $303,588 Not Listed For Sale

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

  118 Ashford Rd Unit 4, Eastford, CT 06242

  118 Ashford Rd Unit 4, Eastford, CT 06242
• 

  

  /21

  $295,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,220 Sq Ft

  118 Ashford Rd Unit 6, Eastford, CT 06242

  Welcome to easy, one-level living in this beautifully maintained and freshly painted home! Nestled in a serene community surrounded by nature. Step into a bright, open layout with cathedral ceilings, a spacious living room, and a granite kitchen featuring stainless steel appliances, ample cabinetry, and a breakfast bar. The primary suite includes a full bath with granite vanity and tub, while an

  Brittany Kimlingen First Choice Realty

  118 Ashford Rd Unit 6, Eastford, CT 06242
• 

  $360,000 Sold Apr 14, 2025

  • 1,236 Sq Ft
  • $291/SF
  • 80 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1988

  155 Boston Turnpike, Eastford, CT 06259

  This well-loved, well-cared for Raised Ranch features a spacious living room with large windows for plenty of natural light on the elevated main level, accessible by a short flight of stairs from the entrance. A working fireplace adds a glow of ambiance and charm! The kitchen, open to the dining/living room, is compact and easy to care for with ample pantry and cabinet storage space. From the

  Debra Burns Berkshire Hathaway NE Prop.

  155 Boston Turnpike, Eastford, CT 06259
• 

  Est $381,923 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,707 Sq Ft

  252 Ashford Rd, Eastford, CT 06242

  252 Ashford Rd, Eastford, CT 06242
• 

  

  /6

  $189,900 Pending

  • Land
  • 18 Acres
  • $10,550 per Acre

  00 Ashford Rd, Eastford, CT 06242

  Build your dream house overlooking the picturesque Ashford Lake. Or Subdivide! Privacy abounds here and the location is prime for commuters and remote workers alike - 20 minutes to UCONN, 30 minutes to Manchester, 1.5 hours to Boston, and 2.5 hours to New York City.

  Rachael Zagurski RE/MAX One

  00 Ashford Rd, Eastford, CT 06242
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  $340,000 Sold Mar 18, 2025

  • 1,792 Sq Ft
  • $190/SF
  • 70 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1940

  187 Old Colony Rd, Eastford, CT 06242

  Welcome to CT's Quiet Corner - 187 Old Colony Road is set on a sweet, private lot backing up to stonewalls and farmland. The home is spacious and well laid out, with 1792 Sqft of living space, 4 bedrooms including a 1st floor primary bedroom with an ensuite bathroom. The eat-in kitchen has been remodeled with stainless steel appliances, granite counters and vinyl plank flooring. Since 2018 all

  Christy Lofstrom Driscoll ERA Blanchard & Rossetto

  187 Old Colony Rd, Eastford, CT 06242
• 

  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
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  /9

  $324,900 Pending

  • 1 Bed
  • 2 Baths
  • 1,167 Sq Ft

  4 Nahaco Hill Ln, Eastford, CT 06242

  WELCOME to Eastford where there are BEAUTIFUL 2025 STAND-ALONE Condos on a dead end cul de sac. ONE YEAR WARRANTY and ONE LEVEL LIVING w/NO Maintenance! STAINLESS appliances, WHITE shaker cabinets, ISLAND w/ GRANITE counters and VAULTED ceiling with OPEN FLOOR PLAN to BRIGHT living room w/ SLIDER to patio. LARGE Primary bedroom w/HUGE closet and Primary bathroom with shower and GRANITE VANITY.

  Christine Johnson RE/MAX One

  4 Nahaco Hill Ln, Eastford, CT 06242
• 

  $317,900 Sold Feb 14, 2025

  • 1,167 Sq Ft
  • $272/SF
  • 44 Days On Market

  • 1 Bed
  • 2 Baths
  • Built 2024

  2 Nahaco Hill Ln Unit 2, Eastford, CT 06242

  READY in 35 DAYS!!! WELCOME to Eastford where there are BEAUTIFUL STAND ALONE Condos BUILT on a dead end cul de sac. **FIREPLACE and ISLAND are EXTRA UPGRADES** ONE YEAR WARRANTY and ONE LEVEL LIVING w/NO Maintenance! STAINLESS appliances, WHITE shaker cabinets and VAULTED ceiling with OPEN FLOOR PLAN. LARGE Primary bedroom w/HUGE closet and Primary bathroom with shower and GRANITE VANITY.

  Christine Johnson RE/MAX One

  2 Nahaco Hill Ln Unit 2, Eastford, CT 06242
• 

  Est $385,849 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  7 Kingsbury Rd, Eastford, CT 06242

  7 Kingsbury Rd, Eastford, CT 06242
• 

  $355,000 Sold Feb 13, 2025

  • 1,560 Sq Ft
  • $228/SF
  • 6 Days On Market

  • 4 Beds
  • 1.5 Baths
  • Built 1927

  99 John Perry Rd, Eastford, CT 06242

  Welcome to your dream home nestled in the heart of the charming small town of Eastford! The interior has been nicely updated, showcasing a harmonious blend of classic features and today's finishes. With 1,560 square feet of well designed living space, this home boasts a large living area, screened porch, four spacious bedrooms and a walk up attic that could be finished for a playroom or office.

  Brooke Gelhaus Compass Connecticut, LLC

  99 John Perry Rd, Eastford, CT 06242
• 

  Est $419,392 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,814 Sq Ft

  10 Providence Pike, Eastford, CT 06242

  10 Providence Pike, Eastford, CT 06242
• 

  $365,000 Sold Dec 30, 2024

  • 1,498 Sq Ft
  • $244/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  14 Ashford Rd, Ashford, CT 06278

  Discover your very own private retreat in this beautifully renovated 3-bedroom, 2-bathroom home, tucked away in a peaceful setting. Newly updated throughout, this home features spacious decks perfect for relaxing or entertaining, and a versatile extra room on the main floor that can serve as an office, playroom, or creative space. There is a finished room in the basement that is complete with

  Ashley Walker Brunet and Company Real Estate

  14 Ashford Rd, Ashford, CT 06278
• 

  Est $272,296 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,336 Sq Ft

  281 Old Colony Rd, Eastford, CT 06242

  281 Old Colony Rd, Eastford, CT 06242

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