1,892

Windham, CT Homes

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  • 69 N Bedlam Rd, Chaplin, CT 06235
    69 N Bedlam Rd, Chaplin, CT 06235
    69 N Bedlam Rd, Chaplin, CT 06235
    /40

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,979 Sq Ft

    69 N Bedlam Rd, Chaplin, CT 06235

    Welcome to your Quintessential New England Equestrian Trial Riders Dream property! Featuring a lovingly preserved and updated antique Cape Cod home, a 40x50' newer five-stall barn with heated tack room and workshop located on a country road with almost 6 private acres of picturesque fenced pasture land adjacent to over 200 acres of preserved forest land and trails. Mansfield Hollow State Park is

    Agent Photo

    Tammy Lucier

    eXp Realty

    (860) 553-9423

    69 N Bedlam Rd, Chaplin, CT 06235
  • 82 Boston Post Rd, North Windham, CT 06256
    82 Boston Post Rd, North Windham, CT 06256
    82 Boston Post Rd, North Windham, CT 06256
    /9

    $1,600 per month

    • 1 Bed
    • 1 Bath
    • 700 Sq Ft
    • Apartment for Rent

    82 Boston Post Rd, North Windham, CT 06256

    First-floor 1 bedroom, 1 bathroom apartment with all utilities included! This well-kept unit offers easy access, a comfortable layout, and worry-free living - perfect for anyone seeking a clean, convenient place to call home.

    Reese Griffin Kazantzis Real Estate, LLC

    82 Boston Post Rd, North Windham, CT 06256
  • 28 Fairway Dr, North Windham, CT 06256

    $52,000 Sold Jul 30, 2025

    • 1,036 Sq Ft
    • $50/SF
    • 69 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1979

    28 Fairway Dr, North Windham, CT 06256

    Nice Mobile Home In Country Club Estates. Home offers covered porch, Open floor plan with eat in kitchen and large living room with bump out so bigger than most. Two Bedrooms with primary at end of home and large with tons of built in for great storage. Large full bath with shower stall and garden tub. Must have Park approval. Lot Monthly Rent is much cheaper than other parks. Fresh paint inside

    Jeanne Crum Home Selling Team

    28 Fairway Dr, North Windham, CT 06256
  • 52 Singleton Rd, Chaplin, CT 06235
    52 Singleton Rd, Chaplin, CT 06235
    52 Singleton Rd, Chaplin, CT 06235
    /36

    $339,900

    • 3 Beds
    • 2.5 Baths
    • 2,440 Sq Ft

    52 Singleton Rd, Chaplin, CT 06235

    ***Highest and best by 8pm on Monday 08/04/25***Welcome to your private retreat in Chaplin! This spacious 3-bedroom, 2-full bathroom ranch is set on just over 5 acres of peaceful, secluded land-perfect for those seeking privacy and a connection to nature. A small pond borders the property, adding charm and tranquility to the setting. The lower level features a large recreational room, ideal for a

    Agent Photo

    Alexis John

    RE/MAX One

    (860) 846-4680

    52 Singleton Rd, Chaplin, CT 06235
  • 11 Crystal Rd, North Windham, CT 06256
    11 Crystal Rd, North Windham, CT 06256
    11 Crystal Rd, North Windham, CT 06256
    /9

    $1,650 per month

    • 2 Beds
    • 1 Bath
    • 723 Sq Ft
    • House for Rent

    11 Crystal Rd, North Windham, CT 06256

    All newly remodeled and painted Cape Cod bungalow style home with new wood laminate floors, first floor bedroom, lower level basement with walk out,location off Boston Post Road, easy commute to main Routes, highways, etc. Short distance to shopping, parks, and recreation

    Robert Ferrigno Ferrigno-Willimantic REALTORS

    11 Crystal Rd, North Windham, CT 06256
  • 36 Fairway Dr, Windham, CT 06256

    $50,000 Sold Jul 29, 2025

    • 672 Sq Ft
    • $74/SF
    • 81 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1971

    36 Fairway Dr, Windham, CT 06256

    2 Bed, 1 Bath Mobile home located in the Country Club Estates Mobile Home Park. Desirable community close to many recreational, shopping, and dining options. This home is waiting to be loved by its next owner. Home being sold in as is condition. All buyers are subject to park approval.

    Erica Molochnick RbRE, LLC

    36 Fairway Dr, Windham, CT 06256
  • 648 N Windham Rd, Windham, CT 06256
    648 N Windham Rd, Windham, CT 06256
    648 N Windham Rd, Windham, CT 06256
    /39

    $399,900

    • 4 Beds
    • 2.5 Baths
    • 2,530 Sq Ft

    648 N Windham Rd, Windham, CT 06256

    Move right into this meticulously maintained Colonial in the heart of North Windham. This spacious home has a lovely open floorplan, combing charming antique features with many modern conveniences. The eat-in kitchen is centrally located, with both the large family room and formal dining room conveniently abutting, just perfect for entertaining! Wooden beams, delightful built-ins and beautiful

    Gina Wentworth Lebanon Green Real Estate

    648 N Windham Rd, Windham, CT 06256
  • 1 Circle Dr, North Windham, CT 06256

    $154,000 Sold Jul 18, 2025

    • 1,436 Sq Ft
    • $107/SF
    • 252 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1987

    1 Circle Dr, North Windham, CT 06256

    Recently remodeled home in Stonegate Manor. This is a three bedroom, two full bathroom double wide on a large corner lot. Two off street parking spots, covered deck/porch and a Klotter Farm shed with electricity. Inside the home you'll find the two bathrooms have been completely remodeled and in excellent shape. The roof is only 4 years young. The main living area has an open floor plan with both

    Ryan Smithwick eRealty Advisors, Inc.

    1 Circle Dr, North Windham, CT 06256
  • 184 Phoenixville Rd, Chaplin, CT 06235
    184 Phoenixville Rd, Chaplin, CT 06235
    184 Phoenixville Rd, Chaplin, CT 06235
    /28

    $384,900 Open Sat 1PM - 4PM

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

    184 Phoenixville Rd, Chaplin, CT 06235

    A unique blend of old-world charm and modern conveniences. Featuring 3 bedrooms and 2 baths, and 1,848 sqft sitting on 1.3 acres. Perfect for those looking for a piece of history with all the comforts of modern living. New windows, new garage roof, landscaping, a large garage and work shop with an above storage loft and parking for 6+. Also an outdoor shower and some beautiful river views steps

    Derek Greene Derek Greene

    184 Phoenixville Rd, Chaplin, CT 06235
  • 168 Miller Rd, Chaplin, CT 06235

    $442,000 Sold Jul 10, 2025

    • 2,754 Sq Ft
    • $160/SF
    • 6 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1945

    168 Miller Rd, Chaplin, CT 06235

    Stunning 4-Bedroom Colonial with In-Law Apartment on 2.5 Acres - Fully Updated Welcome to this beautifully renovated 4-bedroom, 2-bath colonial offering over 2,700 sq ft of versatile living space, situated on a peaceful and private 2.5-acre lot. Boasting a stunning in-law apartment with its own private entrance and new appliances, this home is ideal for multigenerational living or added rental

    Crystal Gebhardt Coldwell Banker Realty

    168 Miller Rd, Chaplin, CT 06235
  • 192 Palmer Rd, Chaplin, CT 06235
    192 Palmer Rd, Chaplin, CT 06235
    192 Palmer Rd, Chaplin, CT 06235
    /34

    $499,900

    • 2 Beds
    • 1.5 Baths
    • 2,954 Sq Ft

    192 Palmer Rd, Chaplin, CT 06235

    Tucked away at the end of a long, private driveway, this sprawling 2-bedroom ranch offers the ultimate in privacy and tranquility. Set on a picturesque 4-acre lot surrounded by nature, this home is perfect for those seeking a peaceful retreat with room to roam. Inside, you'll find a spacious and flexible floor plan with generous living areas, large windows that bring the outdoors in, and the ease

    Lisa Barstow Simply Sold Real Estate

    192 Palmer Rd, Chaplin, CT 06235
  • 31 Pumpkin Hill Rd, Chaplin, CT 06235

    $400,000 Sold Jul 03, 2025

    • 1,596 Sq Ft
    • $251/SF
    • 8 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 2000

    31 Pumpkin Hill Rd, Chaplin, CT 06235

    Welcome to this beautifully updated 1,596 SF Cape-style home, perfectly situated on 2 peaceful acres along a non-through road. Completely turnkey and move-in ready, this charming 4-bedroom, 2-bath residence blends classic style with modern comfort. The main level offers incredible convenience with two spacious bedrooms, a full bath with laundry, and a stunning brand-new kitchen featuring stylish

    Jared Meehan RE/MAX Bell Park Realty

    31 Pumpkin Hill Rd, Chaplin, CT 06235
  • 80 Tuckie Rd, Windham, CT 06280
    80 Tuckie Rd, Windham, CT 06280
    80 Tuckie Rd, Windham, CT 06280
    /40

    $449,900 Pending

    • 3 Beds
    • 3.5 Baths
    • 2,389 Sq Ft

    80 Tuckie Rd, Windham, CT 06280

    Beautiful Contemporary on 2.06 acres of professionally landscaped grounds. Home is set back off the road allowing for privacy and space. Walk thru the front door and there is a first floor bedroom and full bath for single floor living if that is what you need. As you continue on it opens up to an open floor plan with soaring vaulted ceilings, skylights and large windows which bring in amazing

    Lisa Pekala Century 21 Clemens Group

    80 Tuckie Rd, Windham, CT 06280
  • 4 Jackson Ln, Mansfield, CT 06250

    $700,000 Sold Jun 27, 2025

    • 2,518 Sq Ft
    • $278/SF
    • 54 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2025

    4 Jackson Ln, Mansfield, CT 06250

    95% COMPLETE. MOVE-IN, IN JUNE to this stunning 4-bedroom, 2.5-bath Colonial which offers an impressive open floor plan with a spacious feeling & easy flow. The foyer welcomes you with French doors leading to a formal study, a spacious coat closet, & a convenient guest bath. The open staircase runs parallel to the entry, adding a unique design touch. Enjoy everyday easy living or entertaining in

    Sheri Shvonski List N Show LLC

    4 Jackson Ln, Mansfield, CT 06250
  • 6 S Bear Hill Rd, Chaplin, CT 06235
    6 S Bear Hill Rd, Chaplin, CT 06235
    6 S Bear Hill Rd, Chaplin, CT 06235
    /33

    $510,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,638 Sq Ft

    6 S Bear Hill Rd, Chaplin, CT 06235

    Welcome to Chaplin! Custom Built Ranch on 2.12 acres has 3 Bedrooms, 2 Full Bathrooms, Home Office, and First Floor Laundry. Large Open Floor Plan for the Family Room and Kitchen with Granite Countertops and Hardwood Floors. Primary Bedroom has Private Bath and Walk-in Closet. Central Air, Covered Front Porch, Deck, Large Walk-Out Basement, and 2 Car Attached Garage. Located on a quiet country

    Mary Ann Bohonowicz Berkshire Hathaway NE Prop.

    6 S Bear Hill Rd, Chaplin, CT 06235
  • 56 Lions Way, Windham, CT 06256

    $150,000 Sold Jun 27, 2025

    • 1,674 Sq Ft
    • $90/SF
    • 46 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2009

    56 Lions Way, Windham, CT 06256

    Welcome to 56 Lions Way !! Beautiful home and well maintained. Offered is an open floor concept. Walk into a spacious living room and kitchen eating area. Kitchen offers large island perfect for entertaining and enjoyment. 3 bedrooms with each having a walk in closet. Master bedroom offers private master bath with separate tub and shower. Nice covered porch to relax on during nice weather. This

    Mary Beth Malin Brunet and Company Real Estate

    56 Lions Way, Windham, CT 06256
  • 108 Federal Rd, Chaplin, CT 06235
    108 Federal Rd, Chaplin, CT 06235
    108 Federal Rd, Chaplin, CT 06235
    /35

    $339,500 Pending

    • 3 Beds
    • 2.5 Baths
    • 1,444 Sq Ft

    108 Federal Rd, Chaplin, CT 06235

    Great 3 bedroom home set on a private 3.99 acres! This home has so much to offer. As you enter into the fireplaced living room you'll notice the beautiful Brazilian teak hardwood floors that continue through the recently updated kitchen and into the large sun-filled great room. The kitchen features granite countertops, stainless steel appliances and plenty of of cabinet space. Off the kitchen is

    Kathleen Holland KW Legacy Partners

    108 Federal Rd, Chaplin, CT 06235
  • 46 Boulevard Rd, North Windham, CT 06256

    $370,000 Sold Jun 27, 2025

    • 1,322 Sq Ft
    • $280/SF
    • 79 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1965

    46 Boulevard Rd, North Windham, CT 06256

    Beautifully Redone 3-Bedroom Home - Move-In Ready! This charming 3-bedroom, 1-bathroom home has been fully renovated! Featuring a brand-new septic system, windows, doors and roof to note a few major elements of this home . Enjoy a perfect balance of convenience and privacy-close to all major amenities yet tucked away off the beaten path. Bright, spacious living areas and an updated kitchen make

    Ashley Walker Brunet and Company Real Estate

    46 Boulevard Rd, North Windham, CT 06256
  • 5 Chaplin St, Chaplin, CT 06235
    5 Chaplin St, Chaplin, CT 06235
    5 Chaplin St, Chaplin, CT 06235
    /40

    $420,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,726 Sq Ft

    5 Chaplin St, Chaplin, CT 06235

    Amazing opportunity to own this charming 1800's antique Colonial farmhouse, blending timeless character with modern updates, set on a beautiful, level 6.06-acre lot in a peaceful historic district. Offering 2,726 sq ft of living space, this serene property features two horse stalls, perfect for equestrian lovers or those simply seeking open space and quiet countryside living. Inside, you'll find

    Oz Pariser Premier Re Group LLC

    5 Chaplin St, Chaplin, CT 06235
  • 5 Chappell St, Chaplin, CT 06235

    $335,000 Sold Jun 20, 2025

    • 1,388 Sq Ft
    • $241/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1954

    5 Chappell St, Chaplin, CT 06235

    This is the one - almost completely updated - turn key house ready for you! Almost 1400 sq ft, newly painted, refinished hard wood floors, brand new stainless steel appliances, Large living room with fireplace. Main level has full bath, 3 bedrooms with additional master bath. Bonus - heated finished basement with another half bath! Great for man cave, kids playroom etc. Large corner lot, level

    Glenn Stavens Aspen Realty Group

    5 Chappell St, Chaplin, CT 06235
  • 187 Tuckie Rd, North Windham, CT 06256
    187 Tuckie Rd, North Windham, CT 06256
    187 Tuckie Rd, North Windham, CT 06256
    /40

    $350,000 Under Contract

    • 3 Beds
    • 2 Baths
    • 2,158 Sq Ft

    187 Tuckie Rd, North Windham, CT 06256

    Welcome to 187 Tuckie Rd! A meticulously maintained 3 bedroom 2 bath cape set on a beautifully private 1 acre lot surrounded by mature trees. As you enter you will love the open layout perfect for entertaining and everyday life! The kitchen features stainless appliances and island with seating which opens to the dining area and den with a brick fireplace. The first floor bedroom is spacious,

    Lauren Iraeta KW Legacy Partners

    187 Tuckie Rd, North Windham, CT 06256
  • 23 Parish Hill Rd, North Windham, CT 06256

    $360,000 Sold Jun 20, 2025

    • 2,316 Sq Ft
    • $155/SF
    • 15 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1715

    23 Parish Hill Rd, North Windham, CT 06256

    Historic 1717 Saltbox Colonial in N Windham - The Thomas Welch Homestead. Own a remarkable piece of Connecticut history with one of Windham's oldest and most storied homes. This Saltbox Colonial offers 3 bedrooms, 2 full baths, and 2,316 square feet of timeless charm and period craftsmanship. Step inside to discover original chestnut wide board flooring, exposed beams throughout, and five

    Rich Marouski Weichert,REALTORS-Four Corners

    23 Parish Hill Rd, North Windham, CT 06256
  • 6 Kitty Ln, Windham, CT 06256
    6 Kitty Ln, Windham, CT 06256
    6 Kitty Ln, Windham, CT 06256
    /12

    $57,000

    • 2 Beds
    • 1 Bath
    • 728 Sq Ft

    6 Kitty Ln, Windham, CT 06256

    Welcome home to this cozy and affordable 2 bedroom mobile home on a perfect level lot. Whether you're starting out or downsizing, this home is move-in ready and full of possibilities. Enjoy quiet living while still being close to shopping dining and more! This home won't last. Make an appointment to see for yourself! As Is.

    Karen Wheeler Regency Real Estate, LLC

    6 Kitty Ln, Windham, CT 06256
  • 2 Skyline Dr, North Windham, CT 06256

    $279,000 Sold Jun 12, 2025

    • 1,311 Sq Ft
    • $213/SF
    • 4 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2002

    2 Skyline Dr, North Windham, CT 06256

    Get ready to move into this wonderful 3 Bedroom single family detached condo with 2 full baths and hardwood floors. Updates include remodeled kitchen, new appliances, furnace, a/c and roof to name just a few items. Nothing to do except pack your bags! Conveniently located close to UCONN, ECSU and the airline trail.

    Lea Borgne Coldwell Banker Realty

    2 Skyline Dr, North Windham, CT 06256
  • 52 Park Dr, Chaplin, CT 06235
    52 Park Dr, Chaplin, CT 06235
    52 Park Dr, Chaplin, CT 06235
    /9

    $149,900

    • 2 Beds
    • 1 Bath
    • 733 Sq Ft

    52 Park Dr, Chaplin, CT 06235

    Remodeled Mobile Home at the End of a Private Road on a Gorgeous 1.25 Acres! Private Level Lot with Two Bedrooms Plus Office!

    Antonio Incontro Countryside Realty

    52 Park Dr, Chaplin, CT 06235
  • 64 Parish Hill Rd, North Windham, CT 06256

    $375,000 Sold Jun 12, 2025

    • 1,260 Sq Ft
    • $298/SF
    • 10 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1951

    64 Parish Hill Rd, North Windham, CT 06256

    Welcome to Parish Hill Road in N. Windham - a rare opportunity to own a home that has been lovingly cared for by its original owner! This charming Cape style home features 3 spacious bedrooms, including a desirable first-floor primary bedroom, and a full bathroom conveniently located on the main floor. Offering 1,260 square feet of living space, this 1951-built gem sits on a sprawling 8.39-acre

    Melinda Walencewicz eXp Realty

    64 Parish Hill Rd, North Windham, CT 06256
  • 5 Woods Way Unit WOOD005, Windham, CT 06256
    5 Woods Way Unit WOOD005, Windham, CT 06256
    5 Woods Way Unit WOOD005, Windham, CT 06256
    /4

    $134,900

    • 3 Beds
    • 2 Baths
    • 1,141 Sq Ft

    5 Woods Way Unit WOOD005, Windham, CT 06256

    Welcome to Stonegate Manor, an all-age active and vibrant community, where you can find yourself in your dream home. We have a stunning, brand new, beautiful, 2025 3 bed, 2 bath home for sale featuring 1141.52 sq ft of beautifully designed living space. Located in North Windham. Step inside to find an open-concept floor plan, hardwood floors, high ceilings and natural light. The kitchen boasts

    Jude Gray Stonegate Manor

    5 Woods Way Unit WOOD005, Windham, CT 06256
  • 46 Lions Way, Windham, CT 06256

    $105,500 Sold Jun 12, 2025

    • 1,296 Sq Ft
    • $81/SF
    • 71 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2005

    46 Lions Way, Windham, CT 06256

    Welcome to affordable one-level living, in this three-bedroom, two-bathroom home! The home has a well-maintained 2-car driveway and a ramp leading up into the home. A grand covered front porch is found on the front of the home, a perfect place to enjoy a peaceful morning. The house features an open kitchen, living, and dining room, ideal for entertaining! The house has a laundry room with a great

    Ryan Lamb RE/MAX Coast and Country

    46 Lions Way, Windham, CT 06256

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