Canterbury Homes under $600,000

Welcome to Canterbury, Connecticut – a charming town nestled in the heart of Windham County, where history meets modern living amidst picturesque landscapes. Known for its rich colonial heritage, Canterbury offers a serene rural atmosphere that appeals to families, retirees, and nature enthusiasts alike. With its quaint streets, lush greenery, and friendly community, it’s no wonder that this town is becoming a sought-after destination for homebuyers.

Canterbury is characterized by its stunning natural beauty, featuring miles of scenic trails and parks, perfect for hiking, biking, and enjoying the great outdoors. The town's commitment to preserving its historical sites adds a unique charm, with landmarks like the Canterbury Historical Society and the historic Canterbury Green. Local events and farmers' markets foster a sense of community, making it easy to connect with neighbors and create lasting memories.

For those in search of their dream home, Canterbury offers an array of properties priced under $600,000. Whether you’re looking for a cozy single-family home, a charming cottage, or a spacious residence with room to grow, the options are plentiful. Many of these homes feature modern amenities while retaining the character and warmth that the region is known for.

Living in Canterbury means enjoying a tranquil lifestyle while still being within reach of larger cities like Hartford and Norwich, providing the perfect balance between rural charm and urban convenience. Explore the inviting homes in Canterbury today, and discover the perfect place to call home in this delightful New England town!

Newest Canterbury Homes under $600,000

$385,000

3 Beds ⋅ 1 Baths ⋅ 24211687 MLS

Welcome to 62 Bates Pond Road in Canterbury, Connecticut - a 3 bed 1 bath SFR with a newly finished basement on a little over 2 acres of land. This property offers privacy, space, and comfortable living in a peaceful setting. Come see what this Canterbury property has to offer.

62 Bates Pond Rd, Canterbury

$285,000

3 Beds ⋅ 1 Baths ⋅ 24210550 MLS

Calling all visionaries, hobby farmers, and country-life dreamers - this one's for you. Set on a sprawling 3+ acre lot in the heart of Canterbury, this 2-3 bedroom, 1-bath cape is full of potential and ready for its next chapter. Original hardwood floors, and the spacious primary suite leads to its own private deck. Two additional bedrooms offer built-ins and cozy, flexible space. A bonus sunroom off the kitchen- is a blank canvas for a home office, plant room, or cozy sitting area, and a walk-up attic adds even more room to grow into. The big-ticket items are already done: newer roof (2024), well pump and oil tank (2020), and a Peerless oil boiler (2019) mean less to worry about and more to look forward to. Outside, a large 2-car garage/barn- bring your chickens, goats, gardens, or just your imagination. Private well and septic on-site. Being sold as-is, it's an incredible opportunity to build sweat equity right in the center of town. Whether you're a renovator, an investor, or someone chasing that homestead dream, 29 Lisbon Rd is ready for you to make it your own.

29 Lisbon Rd, Canterbury

$324,900

3 Beds ⋅ 1 Baths ⋅ 24209406 MLS

RARELY available is this 3 bedroom ranch sitting on a PICTURESQUE 5.4 acre lot at 35 Jimmy Road in Canterbury! ONE LEVEL LIVING featuring a convenient and inviting floor plan w/ modern amenities, plenty of natural light shining throughout, and 1056 SQFT of comfortable living space! The remodeled kitchen features granite countertops, SS appliances, range hood, plenty of cabinetry, pantry w/ slide out shelving and opens up to the dining area w/ french doors to private back deck. 3 generously sized bedrooms and a full bath w/ skylight. Relax out back on your 15x25 TREX deck overlooking the private back yard and enjoy the serene and tranquil country setting, a true nature lover's paradise, sitting on a 5+ acre lot nestled amongst the trees w/ plenty of room for just about anything, your own personal private OASIS! Additional features include a new well pump/tank, generator hook-up, solar panels to offset electrical/heating costs, and a wood stove in basement as an additional heating option. Located in a quiet and peaceful country setting while providing easy access to local schools, shops, restaurants, parks, I-395 and Route 6, this special home will not last and can be yours now!

35 Jimmy Rd, Canterbury

$439,900

3 Beds ⋅ 2 Baths ⋅ 24209121 MLS

Canterbury's scenic country roads and rural charm set the scene, and this home fits right in! A large, cleared yard, trees for added privacy, and evenings around the fire pit make it easy to picture life here. Inside, this move in ready home offers three bedrooms, hardwood floors, central air, and updates throughout. An additional office on the lower level gives you space to work from home without giving up a bedroom. Newer mechanicals and a quality roof add to the appeal. When the weather warms up, the backyard is the place to be. Take a dip in the above ground pool, have dinner on the deck, or toss a ball for your four legged friend. There is room to garden, play, and enjoy the outdoors. And then there is the 30 x 30 garage, with space for vehicles, tools, and the projects you have been waiting to tackle. Ample driveway parking means room for company, too. With so much to enjoy and an attractive price you will see the only thing missing is YOU!

146 Hanover 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.

1 Library 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

$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

$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

Start Your Search

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but is not guaranteed. © 2026 State-Wide Multiple Listing Service. All rights reserved. Data Last Updated:

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.