21

Windham County CT Homes for Sale with Pool

Section Image Section Image
  • /40

    $415,000 Open Sun 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 1,839 Sq Ft

    18 Highland Street Extension, Moosup, CT 06354

    This inviting 3-bedroom, 2-bath raised ranch offers comfort and space for everyone. Over 1800sqft with the finished lower level. The main level features a spacious living room, dining area, and kitchen, perfect for everyday living and family gatherings. The finished basement adds even more value to this home with a cozy movie theatre, a fun playroom, and a quiet office space-ideal for work or

    Agent Photo

    Jennifer Lehto

    Kazantzis Real Estate, LLC

    (860) 385-6241

    18 Highland Street Extension, Moosup, CT 06354
  • /40

    $500,000 Open Sun 12PM - 2PM

    • 4 Beds
    • 3 Baths
    • 2,503 Sq Ft

    63 Parent Hill Rd, Moosup, CT 06354

    A stunning kitchen, massive spa-style primary bath, and a barn with serious potential make this massive-yet-inviting property a standout. The kitchen, primary suite, and bedroom were all updated within the last two years. The Primary Suite is a true show stopper, featuring an enormous bedroom, huge walk in closet, and one of the most beautiful bathrooms you've ever seen; complete with clawfoot

    Dave Nielson Keller Williams Realty Leading Edge

    63 Parent Hill Rd, Moosup, CT 06354
  • /27

    $450,000

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

    17 Old Hampton Rd, Canterbury, CT 06331

    Room to grow and space to breathe on 1.7 acres! Quietly situated on a dead-end street, this charming three-bedroom, 2-bath home offers you a lifestyle of privacy and easy living with owned ground-mount solar panels. Step inside this home to discover a thoughtfully maintained residence with endless potential. The spacious kitchen and dining areas flow effortlessly into a welcoming living space,

    Kendra Bonette Coldwell Banker Realty

    17 Old Hampton Rd, Canterbury, CT 06331
  • /37

    $415,000

    • 3 Beds
    • 1.5 Baths
    • 1,922 Sq Ft

    3 Woodstock Ave W, Putnam, CT 06260

    This character-filled home sits on a private and generous 1.39-acre lot-offering room to breathe, space to grow, and plenty of possibilities. With 1,922 square feet, this 3-bedroom, 1.5 bath residence is move-in ready and full of potential for the right buyer with vision and energy. Durable HardiePlank fiber cement siding wraps the home in timeless style and long-term protection-resisting

    Beth Fournier Compass Connecticut, LLC

    3 Woodstock Ave W, Putnam, CT 06260
  • /18

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 2,326 Sq Ft

    24 Plaza St, Brooklyn, CT 06234

    Charming Brooklyn Oasis on a Dead-End Road! Welcome to this stunning home tucked away on a peaceful dead-end street in Brooklyn. This unique property offers the perfect blend of comfort, character, and outdoor enjoyment. Featuring 3 bedrooms and 2.5 baths, including a bedroom suite, this home is designed for both relaxation and entertaining. Enjoy an open-concept floor plan that seamlessly

    Missy Greene eXp Realty

    24 Plaza St, Brooklyn, CT 06234
  • /27

    $518,000

    • 4 Beds
    • 2.5 Baths
    • 2,698 Sq Ft

    213 Church St, Brooklyn, CT 06234

    Welcome to this stunning Colonial home, a true gem that blends comfort with elegance. This spacious property features four inviting bedrooms and two and a half baths, offering plenty of room for family and guests. The home boasts multiple closet spaces, ensuring ample storage for all your needs.Brand new floors all through out the house. Step outside to enjoy the above-ground pool, perfect for

    Claudia Bergstrom RE/MAX Diverse

    213 Church St, Brooklyn, CT 06234
  • /37

    $670,000

    • 4 Beds
    • 2.5 Baths
    • 2,514 Sq Ft

    433 E Thompson Rd, Thompson, CT 06277

    Relax on the pretty farmers porch while you plan summer fun! The newer, composite deck is accessible from the kitchen. A covered patio has enough seating for most large parties. Splash around in the single depth pool. Enjoy multiple hobbies in the 5 year old, detached garage. The level yard supports outdoor activities, too. If it's too warm outside, come in where there is central a/c. Newly

    Lynn Converse RE/MAX Bell Park Realty

    433 E Thompson Rd, Thompson, CT 06277
  • /4

    $565,000

    • 4 Beds
    • 4 Baths
    • 5,176 Sq Ft

    50 High St, Moosup, CT 06354

    This expansive Cape Cod-style home is a hidden gem, situated on 2.72 acres with a wraparound driveway complemented by an additional parking area. The two-car garage is located beneath the house, and the home features spacious rooms with ample storage throughout. The dining room boasts a beautiful fieldstone fireplace, while the bar area is carpeted wall-to-wall. The kitchen offers abundant

    Liz Lavallee Dawn Taylor Real Estate

    50 High St, Moosup, CT 06354
  • /28

    $550,000

    • 4 Beds
    • 3 Baths
    • 2,644 Sq Ft

    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
  • /37

    $699,000

    • 4 Beds
    • 2.5 Baths
    • 2,682 Sq Ft

    37 Pulpit Rock Rd, Woodstock, CT 06281

    Welcome to this classic New England Colonial set on a serene 1.6-acre lot on a designated scenic road, steps from historic Woodstock Hill and the Woodstock Academy. Spanning 2,682 sq. ft., this charming property boasts four bedrooms and timeless elegance with thoughtful details throughout. The kitchen features wide-plank oak floors, a cozy dining area, and an open-concept layout, making it ideal

    Kristen Kaskela Berkshire Hathaway NE Prop.

    37 Pulpit Rock Rd, Woodstock, CT 06281
  • /39

    $429,900

    • 3 Beds
    • 2 Baths
    • 1,892 Sq Ft

    13 Foster St, Danielson, CT 06239

    Charming 3-Bedroom Raised Ranch - Fully Renovated! Move right into this beautifully updated 3-bedroom, 2-bathroom raised ranch, offering modern finishes and a spacious layout. The interior has been recently renovated and features fresh paint and all-new vinyl plank flooring throughout. The brand-new kitchen is a showstopper with new cabinets, sleek quartz countertops, and new stainless steel

    Tanya McDermott Berkshire Hathaway NE Prop.

    13 Foster St, Danielson, CT 06239
  • /32

    $399,000

    • 4 Beds
    • 3 Baths
    • 1,452 Sq Ft

    53 Andrews Rd, Woodstock, CT 06281

    Set on nearly 3 peaceful acres in Woodstock, this 4-bedroom Cape offers a flexible layout with three bedrooms on the main level, including the primary, plus a spacious loft-style 4th bedroom upstairs. The home features many recent updates: Pergo flooring in the kitchen and full bath (2022), new dishwasher (2025), water heater (2022), furnace (2019), and a repointed chimney (2021) with liner

    Kristen Kaskela Berkshire Hathaway NE Prop.

    53 Andrews Rd, Woodstock, CT 06281
  • /32

    $69,900

    • 2 Beds
    • 1 Bath
    • 920 Sq Ft

    25 Connecticut 197, Woodstock, CT 06281

    First time on the market in years! Located in the sought-after Meadowside community, this spacious lot offers the perfect seasonal escape. The property features a newer 12x27 loft-style structure with ample room to accommodate multiple beds, same sized spacious living room area, plus a covered 12x28 area ideal for relaxing or entertaining. Also included is a well-maintained 10x26 1981 camper

    Melanie Taylor Berkshire Hathaway NE Prop.

    25 Connecticut 197, Woodstock, CT 06281
  • /26

    $80,000

    • 1 Bed
    • 1 Bath
    • 420 Sq Ft

    174 Laurel Ln Unit 40, Ashford, CT 06278

    Move-In Ready Seasonal Retreat - Immaculate & Fully Furnished. Escape to this beautifully maintained 1-bedroom, 1-bath getaway that comfortably sleeps four. Featuring an eat-in kitchen and cozy living area with a fireplace, this fully furnished home-inside and out-offers everything you need for a perfect seasonal escape. Enjoy the comfort with two AC/heat split systems and ceiling fans

    Patricia Williams William Raveis Real Estate

    174 Laurel Ln Unit 40, Ashford, CT 06278
  • /28

    $399,900 Open Mon 5PM - 6:30PM

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft

    12 Cove St, Danielson, CT 06239

    Welcome to this well-maintained home in a quiet neighborhood at the end of a cul-de-sac (Just min. From Rhode Island line) . The first floor features a large modern kitchen, dining room, family room, one bedroom, and one full bathroom. The second floor features updated flooring throughout and 3 bedrooms including a large primary bedroom with skylights and a large attached bathroom with a brand

    David Viveiros Century 21 Limitless

    12 Cove St, Danielson, CT 06239
  • /31

    $369,999

    • 4 Beds
    • 2 Baths
    • 1,868 Sq Ft

    251 Slater Hill Rd, Dayville, CT 06241

    Welcome to this spacious family home sitting on a beautiful 1.7 acres of land! 4 bedrooms & 2 full bathrooms. BRAND NEW ROOF! This home has it all. Great entertaining space on the first floor with a super spacious kitchen, dining space, living room, 1 full bathroom, bedroom , and first floor laundry. Upstairs you will find 3 additional bedrooms, 1 full bathroom and secondary living/lounging

    Skyla Gagnon RE/MAX Bell Park Realty

    251 Slater Hill Rd, Dayville, CT 06241
  • /16

    $45,000

    • 1 Bed
    • 1 Bath
    • 300 Sq Ft

    25 Route 197 Unit Lot 40, Woodstock, CT 06281

    Welcome to your home away from home! This is your opportunity to own your very own campsite located in in the beautiful Meadowside of Woodstock community! Included is a 1995 33' Corsica Cobra 30BH trailer that has been well cared for. The trailer has a queen bed and a bunk room with two additional sleeping bunks, a full bath with a standup shower and an eat-in kitchen. There is an addition which

    Keri Roy Kazantzis Real Estate, LLC

    25 Route 197 Unit Lot 40, Woodstock, CT 06281
  • /31

    $329,000

    • 5 Beds
    • 2 Baths
    • 2,600 Sq Ft

    670 Wauregan Rd, Brooklyn, CT 06234

    Charming 1889 Colonial in a Beautiful Country Setting! Step into the timeless charm of this well-maintained 1889 Colonial, offering plenty of space for a big family and endless possibilities to make it your own! With a newer septic system, newer windows and a peaceful country setting, this home is ready for you to move in and personalize with minor updates as you live here. Conveniently

    Ann Rochester RE/MAX One

    670 Wauregan Rd, Brooklyn, CT 06234
  • /40

    $1,600,000

    • 6 Beds
    • 6 Baths
    • 4,517 Sq Ft

    6 & 8 Stone Bridge Rd, Woodstock, CT 06281

    The Historic General Samuel McClellan Estate - A Timeless Luxury Retreat. Experience the perfect blend of historic grandeur and modern luxury at this extraordinary estate, meticulously restored with $1.3 million in improvements. This multi-residence compound offers exceptional living and investment potential. Three Distinctive Homes: The Main House - A former bed and breakfast featuring six

    John Downs Berkshire Hathaway NE Prop.

    6 & 8 Stone Bridge Rd, Woodstock, CT 06281
  • /39

    $299,700

    • 3 Beds
    • 2 Baths
    • 2,423 Sq Ft

    118 Windham Center Rd, Windham, CT 06280

    Welcome to this charming Single Family Colonial Farmhouse located in the picturesque town of Windham, Connecticut. Situated on 4.52 sprawling acres, this property has endless possibilities for expansion and enjoyment. The Colonial-style farmhouse exudes timeless appeal, featuring a front porch and side porch, perfect for relaxing and soaking in the peaceful surroundings. Boasting 3 bedrooms and

    Todd Rolland LAER Realty Partners

    118 Windham Center Rd, Windham, CT 06280
  • /2

    $325,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,878 Sq Ft

    241 Ballamahack Rd, Windham, CT 06280

    Welcome to this charming Cape Cod-style home set on 1.39 peaceful acres in. This beautifully maintained property boasts a brand-new kitchen with modern finishes, along with a bright bay window that floods the space with natural light. Step outside to enjoy the enclosed seasonal in-ground pool-perfect for relaxing and entertaining during the warmer months, all while offering added privacy and

    Sonja Perpignan ERA Key Realty Services

    241 Ballamahack Rd, Windham, CT 06280
How to Buy a Home How to Finance a Home How to Sell a Home