Canterbury Real Estate

Welcome to Canterbury, Connecticut—a charming town nestled in the heart of Windham County. Known for its picturesque landscapes and rich historical heritage, Canterbury offers a unique blend of rural tranquility and community spirit, making it an ideal place to call home.

With a population of just over 5,000 residents, Canterbury maintains a close-knit atmosphere where neighbors become friends. The town is steeped in history, with its roots tracing back to the 17th century. You can explore the remnants of its past through beautifully preserved colonial architecture, including the iconic Canterbury Historical Society and the charming town center, where quaint shops and local eateries invite you to linger.

Nature enthusiasts will find plenty to love in Canterbury. The town is surrounded by lush forests and serene landscapes, providing ample opportunities for hiking, biking, and outdoor adventures. The nearby Quinebaug River offers scenic spots for fishing and kayaking, while the stunning views from local parks, such as the Canterbury Town Park, are perfect for picnics and family gatherings.

Canterbury is also known for its excellent school system, making it a great choice for families looking to settle down in a nurturing environment. With a strong sense of community, residents enjoy seasonal events, farmers' markets, and local festivals that celebrate the town’s vibrant culture.

Whether you’re drawn by the historical charm, the scenic beauty, or the welcoming community, Canterbury, CT, is a hidden gem waiting to be discovered. Embrace the tranquil lifestyle and make this enchanting town your new home!

Newest Listings in Canterbury

$449,900

3 Beds ⋅ 2 Baths ⋅ 24202314 MLS

PRIVATE setting sits this BEAUTIFUL PRISTINE Contemporary POST & BEAM with OVERSIZED 2 1/2 car garage 28 x 36 w/ huge storage area above built in 2000, work bench conveys. David Hecht HICKORY cabinets, GRANITE counters/ breakfast bar, appliances convey next to dining area. VAULTED living room w/ FIREPLACE and EXPOSED BEAMS w/ slider out to HUGE 12 x 36 DECK. 1/2 bath w/ washer/dryer ( conveying). HARDWOOD stairs lead to LARGE primary bedroom w/ plenty of closet space and have your morning coffee on the 12 x 12 deck overlooking PRIVATE back yard 2.32 ACRES w/ pool and 12 x 12 deck. Full bathroom and 2 more bedrooms on upper level. FRONT entrance has a COVERED 12 x 12 porch.*** Both levels have PINE Floors underneath flooring.*** 2 mini splits 1 up and 1 down, Generator hook up (generator conveys), 2024 ROOF, lower level has wood burning stove and work benches convey. PAVED driveway.*** 3 sources of HEAT- wood burning stove, boiler and mini splits***Property has CAMERA/AUDIO.

86 Goodwin Rd, Canterbury

$550,000

24194772 MLS

56.38 Acres * 2,900 Feet of Combined Road Frontage * Outstanding Subdivision Potential .... Exceptional opportunity to own 56.38 acres in the scenic countryside of Canterbury. Offering approximately 1,900 feet of frontage on Walker Road and an additional 1,000 feet of frontage on John Brook Road, this beautiful parcel features gently rolling to mostly level terrain, mature hardwoods, picturesque stone walls, a meandering stream and abundant wildlife including deer and pheasants. The expansive road frontage and size present outstanding potential for future subdivision, subject to local approvals. Perc testing was most recently completed in 2009. Whether you're a developer, builder, investor, or someone seeking a remarkable estate setting, this property offers the rare combination of privacy, natural beauty, and development potential. Conveniently located while maintaining the peaceful character of rural Connecticut, this is a unique opportunity to create something special. Buyer to perform their own due diligence regarding subdivision and development possibilities.

121 Walker Rd, Canterbury

$534,000

3 Beds ⋅ 2 Baths ⋅ 24195989 MLS

Turnkey on 3+ Acres - NEW roof, NEW siding, NEW gutters, NEW windows, NEW bathrooms, NEW flooring, composite deck... you have to see it for yourself! Experience contemporary charm in this fully transformed 3 bedroom, 2 bathroom ranch situated on over 3 acres of private land! Every inch of living space in this property has been completely reimagined with top-tier materials and clean design. An open-concept interior features an updated kitchen with modern fixtures, stainless steel appliances & quartz countertops. The living room boasts a charming fireplace, through to the tiled sunroom and beautifully appointed bathrooms. The expansive barn - complete with stables - is a gem! Don't wait on this one!

17 Wauregan Rd, Canterbury

$399,600

3 Beds ⋅ 2 Baths ⋅ 24195021 MLS

CHARMING 1752 QUINTESSENTIAL CENTER CHIMNEY COLONIAL ON NEARLY 2 ACRES OF PRETTY LANDSCAPE. LOVINGLY MAINTAINED FOR OVER 40 YEARS THIS CAPTIVATING CLASSIC FEATURES ORIGINAL PERIOD DETAILS HIGHLIGHTING 5 WORKING FIREPLACES WOW, FUNCTIONAL BEEHIVE OVEN, ORIGINAL BUTTERY, WONDERFUL CHESTNUT AND PINE WIDE BOARD FLOORS AND 2 STAIRCASES. SPACIOUS EAT-IN-KITCHEN WITH UPDATED STAINLESS APPLIANCES, CORIAN COUNTEROPS AND FARMHOUSE SINK SIT BY THE FIRPLACE AND ENJOY! THE KITCHEN OPENS TO A KEEPING ROOM WHERE YOU CAN GATHER AROUND THE BEEHIVE OVEN AND HEARTH. THE MAIN LEVEL CONTINUES WITH THE FORMAL DINING ROOM, PINK PARLOR AND DEN WHICH LEADS TO RELAXING TIME IN THE SCREENED IN PORCH. THE SECOND FLOOR BOASTS AN ELEGANT PRIMARY BEDROOM WITH FIREPLACE AND 2-3 ADDITIONAL VERSATILE BEDOOMS COULD ALSO BE USED FOR AN OFFICE, EXTRA CLOSET OR PLAYROOM. FABULOUS 2ND FLOOR LAUNDRY ROOM. ATTIC SPACE SURPRISES. 3 CAR GARAGE. SHED/MANCAVE. NUMEROUS UPGRADED MECHANICALS INCLUDING NEWER DRILLED WELL, OIL TANK AND MORE. CANTERBURY IS RICH IN LOCAL HISTORY AND THIS HOME IS A TRUE GEM!

11 N Canterbury Rd, Canterbury

$310,000

2 Beds ⋅ 1 Baths ⋅ 24193935 MLS

Welcome to this well-maintained 2-bedroom, 1-bath home situated on 0.89 acres in Canterbury, CT. Filled with natural light, the bright and inviting interior features beautiful hardwood floors, fresh paint throughout, and comfortable living spaces that are ready for you to make your own. The oversized detached two-car garage with its own electrical service is perfect for a workshop, hobbies, or extra storage. Outside, the spacious yard offers plenty of room for gardening, entertaining, or simply enjoying the peaceful setting with views of the neighboring pond. Whether you're a first-time homebuyer, looking to downsize, or searching for a property with exceptional garage space, this home offers a great combination of comfort, functionality, and country charm.

543 Lisbon Rd, Canterbury

$699,900

3 Beds ⋅ 3 Baths ⋅ 24193001 MLS

Experience the perfect blend of timeless charm and upscale finishes in this nearly brand new* custom home. Best of all, there's still time to select some of the finishing touches and make this home uniquely yours. Designed with everyday living and entertaining in mind, this exceptional home offers 3 bedrooms, 2.5 baths, plus a versatile flex room ideal for a home office, fitness room, playroom, craft room, or guest space. At the heart of the home is a stunning chef's kitchen featuring quartz countertops, a pot filler, and a beautifully appointed beverage station complete with a beverage fridge. Open, inviting living spaces create the perfect atmosphere for gathering with family and friends. The luxurious primary suite is your private retreat, showcasing a spa-inspired custom bathroom and an oversized walk-in closet designed to impress. Outside, enjoy the peace and privacy of 2.27 picturesque acres surrounded by a tranquil country setting. The property also features a detached 3 car garage and an oversized detached 2 stall shed with an additional finished room and electricity; ideal for a workshop, studio, hobby space, home office, or other possibilities. Offering the beauty and efficiency of new construction without the wait, this exceptional home combines quality craftsmanship, modern luxury, and the serenity of country living! *With the exception of a small portion of the basement, garage, outbuilding, the well & the leach fields, everything has been newly co

104 Hanover Rd, Canterbury

$580,000

3 Beds ⋅ 3 Baths ⋅ 24188698 MLS

Spacious 3-bedroom, 2.5-bath home situated on 16.4 picturesque acres on a quiet country road in Canterbury. This property offers a wonderful mix of open fields and wooded land, making it ideal for horses, hobby farming, recreation, or simply enjoying privacy. The home features a dedicated office, cedar closet, attached 2-car garage, and numerous updates including newer windows, siding, doors, and roof. Enjoy outdoor living and entertaining on the large rear deck overlooking the peaceful surroundings. The 26' x 26' barn provides storage for approximately 800 bales of hay and offers excellent space for livestock, equipment, or workshop use. The acreage provides endless opportunities for gardening, trails, and outdoor activities. Potential exists to subdivide an additional building lot (subject to town approvals). Convenient country location with the perfect balance of rural charm and everyday functionality. A rare opportunity to own a versatile property with acreage in desirable Canterbury.

107 N Society Rd, Canterbury

$550,000

24177998 MLS

Discover the beauty and character of this stunning 43.3-acre parcel featuring a perfect blend of wooded areas and open fields, offering endless possibilities for your dream home, private retreat, recreational getaway, or future investment. A shared drive provides access beginning at a truly unique feature - an old covered bridge located on the property that is proudly listed on the National Covered Bridge Registry, adding timeless charm and historic significance rarely found today. Enjoy peaceful surroundings, natural beauty, and the opportunity to own an extraordinary piece of land with both privacy and character. A rare property with history, scenery, and potential all in one.

North Canterbury Road, Canterbury

$90,000

24174278 MLS

Located in area of new homes. Slightly wooded. Great location to build your new home.

35 Brooklyn Rd, Canterbury

$90,000

24174312 MLS

Located on country Rd. Lightly treed lot. Perc tested and septic plans available.

45 Brooklyn Rd, Canterbury

$159,500

24170004 MLS

GREAT OPPORTUNITY FOR RESIDENTIAL DEVELOPMENT! 133 ACRES!! SOLD AS A PACKAGE ONLY WITH LISTING #24124218 TOTAL LAND BEING SOLD IS 133 ACRES(APPROX) and TOTAL ROAD FRONTAGE IS 350 FT(APPROX) WITH BOTH PARCELS COMBINED. BUYER TO PERFORM DUE DILIGENCE TO DETERMINE AVAILABLE LAND USE, ZONING REGULATIONS, UTILITES.

Brooklyn Road, Canterbury

$124,900

24164995 MLS

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).

161 Lisbon Rd, Canterbury

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