Canterbury Real Estate

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

71 Gayhead Rd Rd, Canterbury
$219,000
1 Beds ⋅ 1 Baths ⋅ 24217389 MLS
Cape Code home with a detached two car garage on a very private 14 acre parcel. Come take a look and bring your updating ideas to make this property your own.

71 Gayhead Rd Rd, Canterbury
92 Brooklyn Rd, Canterbury
$439,000
4 Beds ⋅ 2 Baths ⋅ 24216685 MLS
Tucked away on 2.27 picturesque acres, this beautiful Colonial offers a wonderful combination of privacy, comfort, and country charm! Set well back from the road and surrounded by mature trees, this inviting 4-bedroom, 2-full-bath home offers 1,862 sq. ft. of bright, welcoming living space. Inside, discover beautiful hardwood floors, tasteful finishes, and an abundance of natural light. The attractive kitchen features granite countertops, stylish cabinetry, tile backsplash, and stainless steel appliances. The comfortable living room includes a masonry chimney with woodstove hookup, perfect for creating a cozy gathering space. A particularly desirable feature is the first floor bedroom and full bath, offering flexibility for convenient main-level living or a wonderful home office with peaceful yard views. Sliders from the dining room lead to a spacious deck, ideal for outdoor dining, entertaining, or simply enjoying the natural surroundings. Upstairs are three additional bedrooms and a full bath. The semi-finished basement offers terrific bonus space for a rec room, home gym, hobbies, home office, or more, along with additional storage. A detached 1-car garage/outbuilding completes the picture. Beautifully maintained, thoughtfully presented, and ready to enjoy!

92 Brooklyn Rd, Canterbury
291 Bingham Rd Unit LOT 19, Canterbury
$110,000
2 Beds ⋅ 1 Baths ⋅ 24214395 MLS
Situated in a quiet and established 55+mobile home community, this well-maintained residence offers affordable, low-maintenance living in a peaceful rural setting. The functional layout features a bright open living area filled with natural light, creating a cozy and welcoming atmosphere for daily relaxation. An efficient kitchen comes equipped with solid cabinet storage and practical workspace, flowing seamlessly into the adjacent dining area. The home features brand new windows (2024) and includes a whole-house generator, providing exceptional peace of mind and year-round comfort. The comfortable bedrooms serve as quiet retreats, complete with good closet storage and easy access to a clean full bathroom setup. Residents enjoy a relaxed, hassle-free lifestyle surrounded by scenic country landscapes, along with private off-street parking. Conveniently located near local parks, state forests, and area amenities, this home provides rural Connecticut charm with easy access to Route 14, Route 169, and I-395 for effortless regional travel.

291 Bingham Rd Unit LOT 19, Canterbury
522 S Canterbury Rd, Canterbury
$400,000
3 Beds ⋅ 2 Baths ⋅ 24213879 MLS
Highest and best offers are due Monday, October 19, 2026, at 5:00 PM. Set on 3.62 acres in Canterbury, this well-maintained 3-bedroom, 2-bath Ranch offers one-level living with numerous improvements! The spacious living room features hardwood floors and a brick fireplace with wood stove insert. The eat-in kitchen offers ample cabinetry and counter space, while the separate dining room features hardwood flooring and a large picture window. All three bedrooms and two full baths are conveniently located on the main level. Major improvements include a new roof with architectural shingles (2023), mini-splits and hybrid water heater (2022), well pump and water tank (2023), seamless gutters (2024), vinyl siding, exterior doors and several windows (2025), and a new patio (2026). The lower level offers additional recreational space, a home office and ample storage. An attached one-car garage is currently used as a home gym, with an adjoining foyer offering mudroom and storage space. A detached rustic barn provides additional covered parking and storage. Enjoy the covered front porch, rear patio, fenced yard and expansive lawns. The property also features large, mature blueberry bushes and an established strawberry patch, perfect for enjoying homegrown fruit. Convenient to Routes 668, 169 and I-395! With substantial improvements already completed and plenty of space inside and out, this property offers a wonderful opportunity to enjoy country living!

522 S Canterbury Rd, Canterbury
254 N Society Rd, Canterbury
$300,000
3 Beds ⋅ 1 Baths ⋅ 24212379 MLS
Walk-in from the inviting front porch of this L-shaped ranch. Quiet country setting with a beautiful backyard and view. The home features spacious rooms including a eat-in kitchen, livingroom with hardwood floors and a gas heating stove. This 3 bedroom home has expansion possibilties in the lower level walkout basement with laundry and garage access. The roof was replaced last year. Conveinient location close to Route 395 and Route 6. Just a short ride to shopping and restaurants.

254 N Society Rd, Canterbury
21/10/A Water St, Canterbury
$200,000
24212217 MLS
Opportunity awaits with this 16.76-acre parcel in Canterbury's Rural District! With frontage along both Water Street (approx. 300') and Kinne Road (approx 350'), this undeveloped property offers exciting possibilities for a variety of buyers. Explore the potential for subdivision and development, or create a private homesite surrounded by acres of your own land. The property's size, configuration and access from two roads may offer flexibility when considering future development plans. RD zoning allows residential and agricultural uses by right, among other potential uses subject to applicable approvals. Whether you're a builder/developer looking for your next project, an investor adding land to your portfolio, or a buyer dreaming of a secluded country property with room to spread out, this parcel is worth exploring. Conveniently located in Canterbury while offering the space and privacy that make rural living so appealing. Buyer to perform due diligence regarding subdivision potential, wetlands, soils, septic, utilities, road frontage and intended use.

21/10/A Water St, Canterbury
62 Bates Pond Rd, Canterbury
$375,000
3 Beds ⋅ 1 Baths ⋅ 24211687 MLS
Welcome to 62 Bates Pond Road in Canterbury-a three-bedroom, one-bath home on just over two acres, offering privacy and a peaceful country setting. The newly finished basement provides flexible space for relaxing, entertaining, a home office, or hobbies. Canterbury offers town-funded high school options, including Woodstock Academy and other area schools, with tuition supported through local taxes. The home will be sold with a full oil tank and a brand-new generator included with the purchase

62 Bates Pond Rd, Canterbury
111 Corey Rd, Canterbury
$649,000
3 Beds ⋅ 3 Baths ⋅ 24209263 MLS
Privacy abounds at this impeccably maintained, custom-built Colonial nestled on over 20 private, wooded acres. Loving care shines through from the original owner of this 2001 gem, featuring a unique and thoughtful floor plan. The main level boasts gleaming hardwood floors, a bright and sunny eat-in kitchen with sliders to the rear deck, and distinct family and living rooms separated by beautiful glass French doors. Stay cozy this winter with the woodstove, perfectly positioned to lower your heating bills with a endless supply of firewood right from your own land! Upstairs, the primary suite offers a peaceful retreat with a private full bath and walk-in closet. Two additional bedrooms flank a shared landing, sitting just steps down the hall from a second full bath that conveniently houses the laundry. A clever hallway nook makes the perfect crafting corner or mini-library, leading into a gigantic bonus room-currently a fantastic billiards and gaming space with endless possibilities. Complete with central air, a classic front porch, a 2-car attached garage, and flexible Canterbury high school choices, this peaceful oasis is within walking distance to the Kinne Preserve hiking trails while remaining an easy commute to major highways. Schedule your private showing today!

111 Corey Rd, Canterbury
1 Library Rd, Canterbury
$425,000
3 Beds ⋅ 3 Baths ⋅ 24207637 MLS
Historic charm meets modern style in this beautifully updated 1800s Colonial offering over 2,100 square feet of spacious living. Set on a beautiful open corner lot in the heart of town, this distinctive home enjoys a picturesque setting surrounded by the character and architecture of a historic New England community. Step inside to discover generously sized rooms and a thoughtfully remodeled interior that brings modern comfort to a classic home. The bright, inviting kitchen features crisp white cabinetry, granite countertops and updated finishes, while the beautifully renovated bathrooms offer a fresh, stylish feel. With more than 2,100 square feet, the home provides wonderful space for everyday living and entertaining, with the character and room sizes that make older Colonials so special. Outside, the open corner lot creates an attractive setting with plenty of space to enjoy. A wonderful opportunity for the buyer who appreciates the charm and history of an 1800s home but wants the beauty and convenience of a modern remodel. Classic New England character, updated interiors and a beautiful in-town location come together in a home that truly stands out. $25,000 credit being offered towards septic repairs.

1 Library Rd, Canterbury
121 Walker Rd, Canterbury
$499,000
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
17 Wauregan Rd, Canterbury
$520,000
3 Beds ⋅ 2 Baths ⋅ 24195989 MLS
NEW Price, NEW opportunity! 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! Come take a look!

17 Wauregan Rd, Canterbury
11 N Canterbury 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
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