Canterbury Real Estate

Welcome to Canterbury, Connecticut – a hidden gem nestled in the picturesque Windham County. This charming town, steeped in history and natural beauty, offers a unique blend of rural tranquility and vibrant community spirit. With its rich colonial heritage dating back to the 17th century, Canterbury boasts a delightful array of historic architecture, including quaint homes and iconic landmarks that tell the story of its past.

Nature enthusiasts will find themselves enchanted by the town’s stunning landscapes. Canterbury is home to vast open spaces, lush forests, and serene waterways, making it an ideal location for outdoor activities such as hiking, fishing, and birdwatching. The nearby Quinebaug River provides opportunities for kayaking and canoeing, inviting residents to immerse themselves in the beauty of the great outdoors.

The community of Canterbury is warm and welcoming, with a strong emphasis on local events and gatherings. Throughout the year, residents enjoy various festivals, farmers' markets, and seasonal celebrations that foster a sense of belonging and camaraderie. Families appreciate the excellent schools and safe neighborhoods, making it a wonderful place to raise children.

Conveniently located near major highways, Canterbury offers easy access to nearby cities while maintaining its small-town charm. Whether you’re seeking a peaceful retreat or a vibrant community filled with life, Canterbury, CT, is the perfect place to call home. Explore the possibilities and discover why so many have fallen in love with this enchanting town!

Newest Listings in Canterbury

$205,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24195270 MLS

Cozy 2-bedroom home with a warm and inviting living room featuring a wood stove. Enjoy the peaceful screened-in porch overlooking a private backyard, perfect for relaxing or entertaining. A great opportunity to make this home your own while adding your personal updates and improvements. Live in it as you renovate and build equity over time.

479 S Canterbury Rd, Canterbury

$399,600

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 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

$350,000

3 Beds ⋅ 1 Baths ⋅ COMING SOON Status ⋅ 24168798 MLS

Move right into this well-maintained 3-bedroom, 1-bath ranch in the heart of Canterbury! Offering a total of 1,764 sq. ft. per town records (1008 up and 756 in lower level), this home features beautiful flooring on main level, fresh interior paint, and a spacious, well-kept kitchen with abundant cabinet storage. All kitchen appliances were replaced in July 2025. 3 standard size bedrooms and an updated full bath complete the main level. The finished lower level provides 2 flex spaces perfect for a home office, gym, playroom, or guest area, plus a pantry/storage closet. You'll also find the laundry area, a furnace installed in 2022, and an additional refrigerator and shelving that will remain with the home. A French drain system was professionally installed around the home to keep the basement dry. Additional highlights include central air, a whole-house generator installed in 2024, a roof approximately 10-11 years old, new storm doors added in 2022 (front) and 2024 (side), and a beautifully constructed retaining wall that enhances the home's curb appeal. The basement features durable concrete floors, offering the opportunity to customize with your preferred flooring. Situated on a level 0.66-acre lot, this property also includes leased solar installed in 2016 with a 20-year PPA. The seller currently pays an average of approximately $160/month for solar plus $23.75/month to Eversource. This move-in ready home has been very well maintained.

38 Ayers Dr, Canterbury

$439,000

2 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24194589 MLS

Welcome to country living at its finest! Nestled on 5.16 private acres, this impeccably maintained custom ranch offers the perfect blend of comfort, quality, and timeless appeal. Built in 2001, this move-in ready home features 1,582 square feet of thoughtfully designed one-level living with gleaming hardwood floors, central air, first-floor laundry, and an attached two-car garage. The spacious kitchen is the heart of the home, boasting granite countertops, abundant cabinetry, a breakfast bar, and an open layout overlooking the dining area with sliders leading outside. Entertain with ease in the formal dining room or unwind in the living room, filled with natural light. The generous primary suite and second bedroom are complemented by two full baths, while the existing three-bedroom septic system offers valuable flexibility for future expansion. Surrounded by mature trees and beautifully maintained grounds, this property provides exceptional privacy without sacrificing convenience. Every room reflects true pride of ownership, making this a rare opportunity to own a meticulously cared-for home where quality, tranquility, and country charm come together.

313 Lisbon Rd, Canterbury

$310,000

2 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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

$499,900

4 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24193050 MLS

This 2,200 sq. ft. Ranch style home has a gardeners dream oasis hiding in the backyard. Lovingly planned over the years, the backyard is filled with mature plantings, stamped concrete patio with gazebo, along with a waterfall featured Koi fish-pond. Home features refinished cabinets, stainless steel appliances, quartz counters, tile backsplash, vinyl plank flooring along with an eating/dining space. The open floor plan leads to the living room with brick wood burning fireplace, hardwood floors along with access to the 20x28 heated/cooled sunroom. There are three bedrooms all on the main level including a primary bedroom suite with a beautiful renovated full bathroom featuring a tiled shower. An additional bathroom is located on the main level along with convenient first floor laundry. The basement is 75% finished between a family room along with a legal 4th bedroom. Efficient WAIR/CAIR heating, 2 car attached garage with auto door opener, 200-amp power generator ready, and even a shed for the garden tools. Schedule your showing today!

455 Westminster Rd, Canterbury

$619,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24191642 MLS

Stunning 2-Year-Young Contemporary Cape on 2+ Private Acres! Welcome to 89 Lisbon Road, a masterfully crafted home where every single detail was carefully considered. Built just two years ago, this pristine property offers the perfect blend of modern luxury, energy efficiency, and peaceful country living in beautiful Canterbury, CT. The 1332sqft upper level is ideal for spacious, open-concept living with adjoining kitchen, dining room, and living room. This space includes a Harmon Pellet Stove included for those cold winter days. Down the hall you will find a primary suite with full bath, 2 additional bedrooms and a 2nd full bath. Need even more room? The lower level features a fully finished 552sqft basement, perfect for a rec room, gym, guest space, or add another bedroom! Huge attached 2-car garage with room for vehicles and all your gear. Enjoy a freshly painted wrap-around deck, perfect for outdoor entertaining, morning coffee, or enjoying the quiet nature views. Equipped with a whole-house generator to ensure you are never left in the dark. 30-yr Architectural Shingle roof for decades of peace of mind. 400-gallon propane tank is leased. This turnkey home looks and feels brand new without the wait of new construction. Schedule your private showing today to experience the impeccable craftsmanship firsthand! Seller under contract on another home and ready to move. Schedule a showing today, you won't be disappointed!

89 Lisbon Rd, Canterbury

$449,900

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24189331 MLS

Move-in ready and beautifully maintained, this charming home offers 3 spacious bedrooms and 2 full bathrooms. The open floor plan creates a bright, welcoming living space that's perfect for everyday living and entertaining. The finished basement is an entertainer's dream, featuring a wet bar and a pool table that's included with the home. With thoughtful updates and plenty of space to relax and gather, this home is ready for its next owners to enjoy.

29 Bingham Rd, Canterbury

$595,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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

$1,200,000

3 Beds ⋅ 2 Baths ⋅ ACTIVE Status ⋅ 24179809 MLS

Exceptional opportunity to own a private country estate featuring a well-maintained Cape-style log home set on 41.83 acres of beautiful land. This charming residence offers 3 bedrooms and 2 full bathrooms, with a comfortable floor plan that includes a spacious family room and a recreation room in the lower level, providing plenty of space for relaxation, entertainment, and hobbies. Enjoy your morning coffee on the front Porch. Accessed through a gated entrance, the property offers outstanding privacy and features a large pond, creating a picturesque setting for outdoor enjoyment, wildlife viewing, or recreational activities. A standout feature is the impressive 4,500-square-foot steel building, complete with 8 overhead doors, a half bath, and a loft area, making it ideal for equipment storage, vehicles, workshops, business use, or a variety of other applications. The property is further enhanced by a fully paid-for solar energy system, helping to offset utility costs and increase energy efficiency. Whether you're seeking a private residence, recreational retreat, hobby farm, or a property with extensive storage and workspace capabilities, this unique offering combines acreage, privacy, and versatility in one exceptional package.

46 Cemetery Rd, Canterbury

$550,000

ACTIVE Status ⋅ 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

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