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401 Tripp Hollow Rd, Canterbury
$699,900
3 Beds ⋅ 3 Baths ⋅ 24148662 MLS
Set on a dead-end road & abutting the Brooklyn border, 401 Tripp Hollow is a refined new construction Colonial by one of the area's most premier builders. One of the final opportunities w/in this subdivision, the home offers over 2,650 square feet of impeccably designed living space on a private 5+ acre setting that delivers rare seclusion, privacy, & timeless appeal. The 1st floor welcomes you w/an open foyer & a seamless, flowing layout ideal for both everyday living & entertaining. Thoughtful design & premium craftsmanship are evident throughout, highlighted by granite countertops, carefully curated finishes, & a bright, open-concept feel. The main living spaces connect effortlessly to a large rear deck overlooking the back yard, creating the perfect setting for outdoor entertaining or quiet relaxation surrounded by nature. The 2nd level features 3 spacious beds, including a luxurious primary suite complete w/a walk-in closet & a full bath w/double vanity. Secondary beds are generously sized, light-filled, & offer abundant closet space. An expansive bonus room provides exceptional flexibility for a media lounge, private office, or additional living area, while 2nd-floor laundry adds everyday convenience. Additional amenities include central air, underground utilities, a generator-ready setup, efficient propane forced air! Set back from the road for maximum privacy, this exceptional residence is expected to be completed within the next 60 days. Truly exceptional!

401 Tripp Hollow Rd, Canterbury

26 N Society Rd, Canterbury
$620,000
3 Beds ⋅ 3 Baths ⋅ 24135751 MLS
Charming New England brick Cape set on a little over 17 private acres overlooking a picturesque pond and rolling hills. Home offers 3 bedrooms and 2.5 baths including a first-floor primary bedroom suite. This property features a massive newly built insulated and heated 28x36 post-and-beam garage/workshop with a full second floor ideal for studio, office or multi-purpose use. Nature lovers will appreciate the surrounding woods, peaceful views, and room to roam - perfect for a true homestead lifestyle, hobby farm, hunting, trail riding etc. With its rare combination of acreage, privacy, this is an opportunity NOT OFTEN found in Canterbury. POSSIBLE potential future subdivision opportunity for added value (buyer to do due diligence).

26 N Society Rd, Canterbury

135 Barstow Rd, Canterbury
$615,000
3 Beds ⋅ 3 Baths ⋅ 24165806 MLS
Welcome to this beautifully crafted new construction Cape set on a private 4-acre lot, offering the perfect blend of modern comfort and timeless design. This 3-bedroom, 2.5-bath home features a desirable first-floor master suite and an open-concept kitchen and dining area complete with stainless steel appliances, granite countertops, and maple cabinetry. Hardwood floors, oak stairs, and abundant recessed lighting highlight the quality craftsmanship throughout, while the electric fireplace adds a warm, inviting touch. Enjoy year-round comfort with central air and propane forced air heat, plus peace of mind with 200-amp electrical service, generator hookup, and exterior flood lighting surrounding the home. Additional features include a finished basement area, convenient first-floor laundry hookups, ample second-floor storage, and a 2-car under garage. Outside, a paved driveway, hydroseeded lawn, and both front and rear pressure-treated decks complete this exceptional property.

135 Barstow Rd, Canterbury

76 John Brook Rd, Canterbury
$615,000
4 Beds ⋅ 3 Baths ⋅ 24145632 MLS
Set on a scenic 4.58-acre private lot, this beautifully maintained Cape offers space, comfort, and recent upgrades in a peaceful Canterbury setting. With approximately 2,920 sq ft of living space, the home features 4 bedrooms, 2 full baths, 1 half bath, and a versatile floor plan well suited for both everyday living and entertaining. Recent improvements add tremendous value, including a new 40-year architectural shingle roof, new hot water tanks, and an upgraded in-ground pool that now functions as a salt-water, spa-like retreat during the season-perfect for summer enjoyment and hosting. The home offers generously sized rooms, multiple living areas, and classic New England charm throughout. Surrounded by mature trees and natural beauty, the property provides a true sense of privacy while remaining conveniently located to local amenities and commuter routes. A rare opportunity to own a thoughtfully updated home on nearly five acres, offering both tranquility and functionality. Being sold AS IS

76 John Brook Rd, Canterbury

63 Buck Hill Rd, Canterbury
$611,000
3 Beds ⋅ 2 Baths ⋅ 24141893 MLS
SELLER ENJOYS A ZERO ELECTRIC BILL AND A QUARTERLY CHECK! The BEST of country living and modern design, all on 10 PRIVATE ACRES. Land is well suited for hunting, agricultural use, gardening and outdoor recreation. This SINGLE-LEVEL RANCH with 2238 sq ft of living space and a 3 CAR GARAGE offers HARDWOOD FLOORS, spacious eat-in kitchen with STAINLESS STEEL appliances and a 32 x 27 GREAT ROOM - perfect for a DINING ROOM/FAMILY ROOM. Home offers a desirable split bedroom floor plan with a large primary suite offering a walk-in closet and a private full bath. Two generously sized additional bedrooms and a 2nd full bath complete the layout. Additional living space can be created in the attic space which had plywood floors and electricity and is accessed from the great room. Walkout basement includes 2 finished heated rooms with electric, oil and wood/coal, as heating sources. Stay cozy with a wood stove and coal, as a supplemental heat source or enjoy year-round comfort with 2 MINI SPLITS for heating and cooling. Home boasts 39 energy efficient SOLAR PANELS, which are OWNED and PAID-IN-FULL! Home also offers electric hot water heat pump, 2 OIL TANKS, a 1500 gallon septic tank and a GENERATOR hookup for peace of mind. Outside, relax by the above-ground POOL, entertain on the large deck, and take in the tranquility of your PRIVATE RETREAT.

63 Buck Hill Rd, Canterbury

153 Wauregan Rd, Canterbury
$580,000
4 Beds ⋅ 3 Baths ⋅ 24136168 MLS
Move right in to this spacious 4 bed, 2.5 bath newer Colonial on 3 acres - set peacefully in the desirable town of Canterbury! Large rooms - one of the 4 could also be used as a second living room or rec room on the second level, a primary suite with walk in closet and it's own private bathroom, hardwoods on the first floor, central a/c, and a big open yard with a custom wooden playset, chicken coop and plenty of privacy! The walk out basement has a nice workshop area and tons of potential for more living space if needed! The electrical has been wired for a generator connection to ease any worry over power outages in storms! Canterbury is a quintessential New England town, charming with its unique local businesses, farms and history. Come see!

153 Wauregan Rd, Canterbury

208 Gooseneck Hill Rd, Canterbury
$550,000
3 Beds ⋅ 3 Baths ⋅ 24143458 MLS
Mechanic's dream on 5 acres. This 3-bedroom ranch combines comfortable one-level living with exceptional space for hobbies, projects, and outdoor enjoyment. Inside, you'll find hardwood floors throughout, a living room with a wood-burning fireplace with insert, and a primary bedroom with its own full bath. The eat-in kitchen includes sliders leading to the back deck, an ideal spot to relax or entertain while overlooking the peaceful property. Car enthusiasts and hobbyists will appreciate the industrial-sized 50 x 60 heated garage equipped with a 2-post lift, creating an incredible workshop setup. A large open room that was originally the home's attached two-car garage was later used as a dog grooming space and has since been cleared out, leaving a blank slate ready for a workshop, home business, additional living space, or convert back to garage. The partially finished walkout basement adds additional usable space with potential for an in-law setup, recreation area, or home office. Outside, the 5-acre property offers privacy and room to roam, along with an additional outbuilding previously used as a dog kennel. A property like this rarely combines land, workspace, and versatile living areas in one setting.

208 Gooseneck Hill Rd, Canterbury

393 N Canterbury Rd, Canterbury
$550,000
4 Beds ⋅ 2 Baths ⋅ 24152199 MLS
Back on the market, massive price drop and appraisal available! Built in 1750 and celebrating its 275th anniversary, this distinguished antique Colonial farmhouse remains a pristine exemplar of early New England architecture. Set on 8.5 acres and nestled on scenic route 169, the estate features a secluded pond, a gently winding brook, and two traditional barns-all original to its historic rural setting. This graceful home offers 5 bedrooms, 2 full bathrooms, and approximately 2,443 sf of living space. On the interior, you'll find antique wide-plank hardwood floors, five fireplaces, handhewn beams, and updated wood siding-each detail preserving the home's timeless charm and architectural integrity . The warm living room, centered around a fireplace, provides a cozy backdrop for gatherings, flowing naturally into the dining space and kitchen with serene views of the surrounding grounds. A remarkable feature is the massive fully enclosed porch, offering an expansive retreat to enjoy the tranquility of your private acreage. The property's two barns present versatile opportunities-from livestock and hay storage to creative reuse. The pond and brook wind through open fields and wooded borders, bordered by classic stone walls-an idyllic, historically authentic New England landscape. With three covered parking spots, this home balances practical convenience with period appeal. 393 North Canterbury Road is a remarkable offering for those who cherish historic New England architecture

393 N Canterbury Rd, Canterbury

505 Brooklyn Rd, Canterbury
$525,000
3 Beds ⋅ 4 Baths ⋅ 24172747 MLS
Nestled on a quiet country road, this well-maintained 1988 Colonial offers the perfect blend of comfort, privacy, and charm. Set on 5 beautiful acres, the property features a paved driveway, inviting front porch-ideal for morning coffee-and thoughtfully designed landscaping that enhances the home's peaceful setting. Inside, you'll find hardwood flooring throughout the first floor, a spacious and functional layout, and a kitchen featuring custom cabinetry. The living room features a beautiful fireplace with a wood stove insert, creating the perfect spot to cozy up during the colder months. Andersen windows throughout the home provide abundant natural light, while central air ensures year-round comfort. Step out onto the back deck and unwind to the sounds of nature, making it the perfect space for relaxing or entertaining. This property offers a rare opportunity to enjoy country living with modern conveniences. PROFESSIONAL PHOTOS COMING ON 5/11

505 Brooklyn Rd, Canterbury

455 Westminster Rd, Canterbury
$492,000
4 Beds ⋅ 2 Baths ⋅ 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

86 Goodwin Rd, Canterbury
$480,000
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

520 Lisbon Rd, Canterbury
$475,000
4 Beds ⋅ 3 Baths ⋅ 24178379 MLS
Three acres, an updated Contemporary home, and room to make it your own. Whether you're dreaming of a garden, some animals, or just space between you and your neighbors - 520 Lisbon Rd delivers. Inside, the clean lines of the Contemporary style pair nicely with a fully updated kitchen featuring a large island, granite countertops and a cathedral ceiling. The first-floor primary suite is huge, with two closets and an updated ensuite. Three bedrooms and another updated bathroom are just upstairs. There's even a finished bonus room above the garage for work or play. An attached 2-car garage, a wood stove for those cold Connecticut nights, and a large deck for those warm summer days, making this property ready for all that life hands you. New septic in 2024, new roof in 2021, and the furnace was just serviced and inspected - all that's left to do is move in. The updates are done, bring your vision. Come see what home feels like.

520 Lisbon Rd, Canterbury

313 Lisbon Rd, Canterbury
$470,000
2 Beds ⋅ 2 Baths ⋅ 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

234 N Society Rd, Canterbury
$470,000
3 Beds ⋅ 2 Baths ⋅ 24179626 MLS
This stunning three bedroom, two bathroom contemporary home perfectly blends modern design with a peaceful country setting. Complete with solar panels and sitting on 2 level acres this place is perfect for homesteaders of all kinds. There is a large barn with power and a separate well, a designated and fully fenced raised bed garden, ready for your summer plantings. There are 2 apple trees,2 pear trees, a peach tree and 2 blueberry bushes already producing fruit, not to mention a chicken coop with enclosed run for your feathered friends. Inside, you will experience the feeling of grandeur with dramatic high ceilings and large windows that flood the home with natural light. A beautiful open staircase exposes the loft area upstairs, a perfect office space, reading nook or additional sitting area. The open concept, living, dining and kitchen areas flow seamlessly, with sliders leading to a large rear deck overlooking the expansive, fenced back yard, making this home perfect for entertaining as well. With an attached oversized garage, a primary bedroom on the first floor adjoined to the bathroom and two more bedrooms and a second full bath on the second floor, this layout is the perfect set up for anyone. Don't miss your opportunity to make this place your own.

234 N Society Rd, Canterbury

4 Bingham Rd, Canterbury
$465,000
3 Beds ⋅ 2 Baths ⋅ 24182346 MLS
This is the property you have been waiting for! Nice three bedroom cape with plenty of updates including 3 new split systems to keep you cool this summer and warm in the winter. New roof, paint and flooring allow you to move right in. The first floor offers eat in kitchen with new counter top and a new refrigerator. Large living room with access to yard, a woodstove that will keep you warm , new plank flooring and split unit to keep you cool. Combination dining room/den or use it any way you like. This room has new carpet and a gas line ready to hook up a propane fireplace should you want. There is a primary bedroom with split unit on first floor. A full bathroom rounds out first floor. Upstairs you will find a landing area at top of stairs, would make a nice computer niche, two bedrooms freshly painted, along with new carpet and a half bath. Outside offers a park like 10 acre lot with 2 ponds, chicken coop, barn/garage and a combination of open, usable land and wooded land. Contractors, mechanics, horse lovers take note! Garage is steel beam construction so no lolly columns or post in the way, an unfinished loft for potential finishing or extra storage, 220 available to handle any power needs. Room to easily fit three cars plus equipment. This property would make a great equestrian set up as well! Beautiful pond in the cleared portion with a second smaller pond in the woods. Chicken coop stays. This is country life at its best! 2001 addition has a full basemnt under it.

4 Bingham Rd, Canterbury

249 S Canterbury Rd, Canterbury
$459,900
4 Beds ⋅ 3 Baths ⋅ 24149736 MLS
A Wonderful opportunity to own a BRAND NEW and quality constructed home in Canterbury, ready for a new owner to move right in and enjoy. Spacious FOUR bedroom and THREE FULL bath, Contemporary Raised Ranch, consisting of 1890 square feet of living space. The home has an open concept with vaulted ceilings and hardwood floors in the upper living area and kitchen. The kitchen is fully applianced, with granite counter tops and a center island. The four bedrooms are spacious and the home has the flexibility for the primary bedroom to be on either the upper of lower level. There is a huge two-car garage, exterior deck, large side yard, energy efficient warm air heat, central air, and much more. Do not miss the opportunity to own beautiful brand new home!!!

249 S Canterbury Rd, Canterbury

173 Bennett Pond Rd, Canterbury
$455,000
3 Beds ⋅ 2 Baths ⋅ 24169550 MLS
***Seller has received Multiple Offers and has asked for Highest and Best by 3:00PM Sunday*** Fully renovated and designed for easy one-level living, this well-built ranch at 173 Bennet Pond Rd. offers over 1,600 square feet of move-in ready space in quiet Canterbury CT. Extensive updates provide true peace of mind, including a brand new kitchen with quartz countertops and stainless steel appliances, updated bathrooms, new plumbing, updated electrical, new heating/cooling and a new septic system. The layout is both functional and efficient, featuring an open kitchen and dining area, and a spacious living room with vaulted ceiling, abundant natural light, and a slider leading to a private deck. A convenient mudroom with attached laundry enhances everyday ease. The home offers three bedrooms and two full bathrooms, including a primary suite with en suite bath. An oversized attached two-car garage adds excellent storage and accessibility, while a bonus space off the garage provides flexibility for a workshop, home gym, or additional storage. Set on over 2.5 acres with a private pond, the property offers a peaceful setting to complement its practical design. A turnkey opportunity for buyers seeking modern updates, low-maintenance living, and the convenience of a single-level home.

173 Bennett Pond Rd, Canterbury

233 N Society Rd, Canterbury
$455,000
2 Beds ⋅ 3 Baths ⋅ 24155241 MLS
Striking west facing A-Frame contemporary designed to capture natural light and stunning sunset views through expansive front windows. This 2 bedroom, 3 full bath home blends architectural charm with everyday comfort. The main level offers an open concept living and dining area with plank style tile flowing throughout, cathedral ceilings and a propane fireplace featuring an updated mantel and surround. Sliders open to a spacious front deck, ideal for relaxing at sunset. The kitchen includes granite countertops, generous cabinetry, and ample prep space. A first floor guest bedroom, full bath with tub, and laundry room with utility sink just off the heated and cooled 2 car attached garage provide true main level convenience. Upstairs, the lofted primary suite overlooks the living area and front windows. The suite features a full bath with skylight and laundry chute, plus an oversized walk in closet complete with its own sauna for a private retreat feel. The finished lower level expands the living space with an exercise room, game room, storage area, and a third full bath with tub. Additional highlights include central air, a hard wired Generac generator, partially fenced yard, and recent updates within the past year including refreshed paint, fireplace improvements, and new refrigerator, washer, and dryer. Easy access to Rt 14 and Rt 169.

233 N Society Rd, Canterbury

58 Campbell Dr, Canterbury
$440,000
4 Beds ⋅ 2 Baths ⋅ 24177220 MLS
HIGHEST AND BEST *** offers due Tuesday June 2nd by 9 PM Welcome to 58 Campbell Drive, where comfort, space, and convenience come together in this beautifully maintained home offering the ease of single level living on a large, level lot. Thoughtfully updated and meticulously cared for, this property features an ideal layout with generous living spaces and exceptional functionality both inside and out. The updated kitchen opens to a bright and inviting breakfast room, creating the perfect setting for everyday living and casual dining. A spacious den with sliders overlooks the sprawling backyard and provides seamless access to outdoor entertaining space. The warm and welcoming living area is centered around a classic wood burning fireplace with beautiful brick masonry detail, adding timeless character and charm. Additional highlights include hardwood floors, fresh interior paint, replacement windows, newer siding, and an approximately eight year old roof, offering peace of mind for years to come. The oversized two car garage provides excellent storage and convenience, while the fully finished lower level with a full bathroom offers incredible flexibility for extended living space, a recreation room, home office, guest suite, or gym.

58 Campbell Dr, Canterbury

38 Ayers Dr, Canterbury
$382,000
3 Beds ⋅ 1 Baths ⋅ 24168798 MLS
MULTIPLE OFFERS - HIGHEST & BEST DUE BY TUESDAY 8/4 1PM. 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.

38 Ayers Dr, Canterbury

516 Brooklyn Rd, Canterbury
$380,000
3 Beds ⋅ 2 Baths ⋅ 24122648 MLS
Looking back, this property has many stories to tell! Built in the 1790's by a prosperous local farmer, the house has been a bustling family and farm hub for more than 200 years including its last owners who set up an alpaca farm and lavished care on the 12.34 wooded and open acres. With large perennial and veggie gardens, formal yard spaces and inground pool to make their mark. The 2740 SF home has 3 bedrooms and 1-1/2 baths, a bright and airy kitchen open to a fireplaced keeping room, and formal living and dining rooms flanking a beautifully finished main entry staircase. The house boasts many original features including wide board floors, a bee-hive oven, and walk-in chestnut pantry. Many improvements have happened over the years from a newer roof and sills to an updated septic/well. A surprise is the Buderus furnace (with 3 zones) installed 10 yrs ago. This home has been loved through the ages and is now ready for its next stewards to guide it along to today's lifestyle!

516 Brooklyn Rd, Canterbury

31 Lovell Ln, Canterbury
$370,000
3 Beds ⋅ 1 Baths ⋅ 24158554 MLS
Welcome to 31 Lovell Lane, a home that immediately feels comfortable the moment you arrive. Tucked back from Route 14 in the heart of Canterbury, this 3 bedroom, 1 bathroom home offers 1,140 square feet of thoughtfully maintained living space and true move in ready convenience. Nearly every detail has been cared for, with updated paint and wallpaper throughout the home completed within the last two years, giving the interior a fresh and welcoming feel. The home is heated by oil, but on those classic New England nights you can light the pellet stove and enjoy the cozy atmosphere it creates. Newer appliances make everyday living simple and stress free. Outside, the property becomes your own personal retreat. Cool off during the summer in the large above ground oval pool installed in 2025, or unwind at the end of the day in your private hot tub. Despite the peaceful setting, you are only minutes from restaurants, grocery stores, and the post office. Whether you are buying your first home, downsizing, or simply looking for a place that feels just right without stretching your budget, 31 Lovell Lane is a home that deserves a spot at the top of your must see list.

31 Lovell Ln, Canterbury

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