Cheshire Homes for Sale

Welcome to Cheshire, Connecticut—a charming town that beautifully blends suburban tranquility with vibrant community life. Nestled in New Haven County, Cheshire is known for its picturesque landscapes, excellent schools, and a strong sense of community. With its tree-lined streets, historic homes, and modern amenities, Cheshire is an ideal place for families, professionals, and anyone seeking a peaceful yet engaging lifestyle.

Cheshire boasts a rich history, evident in its well-preserved architecture and inviting neighborhoods. Residents enjoy a plethora of recreational activities, from hiking along the scenic trails of the nearby Sleeping Giant State Park to exploring the quaint shops and restaurants in the town center. The local parks, such as Bartlem Park and Cheshire Park, offer family-friendly facilities, making it easy to enjoy outdoor activities year-round.

For those looking to make Cheshire their home, you’ll find a diverse array of homes for sale that cater to various tastes and budgets. From charming colonial-style houses to modern, spacious townhomes, each property reflects the town’s unique character and warmth. The real estate market in Cheshire is thriving, with opportunities for first-time buyers, growing families, and those seeking a serene retirement retreat.

With its strong community spirit, excellent schools, and beautiful surroundings, Cheshire is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover the perfect property to call your own in this delightful New England town!

Newest Cheshire Homes for Sale

$459,900

3 Beds ⋅ 1 Baths ⋅ 24199844 MLS

Move In ready! Home Sweet Home! Look No Further! Tired of hearing the same old thing? 950 Peck Lane is so amazing, you will stop your search here! Come see for yourself what this 3 bedroom 1 1/2 bath ranch style home offers and watch your wish list dwindle to nothing. Outstanding features include beautiful hardwood floors throughout, updated kitchen and baths, a 1 car attached garage, central air. Outside welcomes you to a deck and gorgeous, level backyard with direct access to Farmington Canal Rail Trail where morning walks or bike rides start or end your day. Siding, Septic Tank, Driveway, Roof, Well Water Tank have all been replaced since 2013. Whole house generator and security system are additional features a new homeowner will inherit. See complete list of upgrades with dates in attachments. This home is 100% ready for a new homeowner to enjoy for years to come.

950 Peck Ln, Cheshire

$450,000

3 Beds ⋅ 2 Baths ⋅ 24205907 MLS

Welcome home to 125 Wallingford Road in Cheshire, CT! Loaded with curb appeal from the moment you arrive, this sweet 1900s home welcomes you with a wonderful wrap-around porch and fenced-in back yard. Extensively renovated in 2009, this charming 3-bedroom, 2-bath home beautifully blends modern updates with the character of its era. Inside, natural light fills the open main level, where wide red oak hardwood floors run throughout. The updated kitchen features white cabinetry, granite countertops, stainless steel appliances and a butcher-block-topped island with seating-perfect for casual meals, working from home or gathering with friends. Two dining areas offer flexibility for everyday living and entertaining. A convenient entry by the back door helps keep things organized, while an office off the kitchen provides a dedicated workspace. There is a main level, beautifully updated full bath with tiled shower. Upstairs are three comfortable bedrooms with hardwood floors and another updated full bath. Major improvements include a new septic tank in 2022 and a new roof and solar installation in 2023. Public water. Centrally located within walking distance of downtown coffee shops, the library, Town Hall and Cheshire Academy, plus a short drive to The Shops at Stone Bridge and convenient access to the Farmington Canal Heritage Trail. Beautifully updated, full of charm and close to so much-125 Wallingford Road is not to be missed!

125 Wallingford Rd, Cheshire

$664,900

4 Beds ⋅ 3 Baths ⋅ 24204339 MLS

Everything you have been looking for is waiting for you in this fabulous home in great neighborhood in the desirable south end of Cheshire and is part of the Roaring Brook Association that offers amazing hiking trails and nature walks. Remodeled custom kitchen and bathrooms, open floor plan that walks out to bright sunroom with electric heat to extend season overlooking private yard with blue-stone patio and firepit. Beautifully decorated with neutral colors makes it easy to see yourself in this lovely home. Kitchen is open to great room with wood burning fireplace, large dining room, first floor office space, and welcoming foyer. Upstairs you have a large Primary suite and three additional bedrooms. Lower level includes a finished office, family room, and workout space. Just pack your boxes and move right in!

750 Foster Ct, Cheshire

$484,900

4 Beds ⋅ 2 Baths ⋅ 24203699 MLS

Amazing quality and custom workmanship throughout this colonial featuring Kitchen with coffered ceiling, Kraft-Maid hickory kitchen cabinets, granite counters, copper backsplash, tongue and groove ceilings & recessed lighting! Vaulted wood ceiling in family room with cultured stone propane fireplace & ceiling fan. Dining room has crown molding and open to kitchen. Formal living room with built in "reading nook" under stairs. First floor full bath has shower, built in radiator/towel warmer, with wood ceiling. First floor bedroom/den. 2nd floor has 3 very generous bedrooms, one with custom builtins & walk-in closet. The full bath with tub on 2nd floor features a tongue and grove ceiling. New oil tank and hot water heater. Close to Linear Trail and Ball & Socket Arts Place. 5-circuit generator hook-up.

72 Willow St, Cheshire

$439,900

3 Beds ⋅ 2 Baths ⋅ 24199826 MLS

Welcome home to 1338 Avon Boulevard, a beautifully updated Cape Cod tucked on a private, tree-lined 0.4-acre lot in sought-after Cheshire. This 3-bedroom, 2-bath retreat blends classic New England charm with thoughtful modern upgrades throughout. Step inside to an open, light-filled living and dining area with gleaming hardwood floors and a statement chandelier, flowing into a chef-inspired kitchen featuring rich blue cabinetry, butcher block countertops, hexagon tile backsplash, and stainless steel appliances. The main level also offers a serene bedroom retreat with a spa-inspired bath: skylights flood the vaulted ceiling with natural light over a dual-vanity counter, matte black fixtures, a glass-enclosed multi-jet shower, and a freestanding soaking tub surrounded by lush greenery. Outside, enjoy your own private oasis. Mature trees and landscaping frame a stone patio built for entertaining, complete with a cozy fire pit seating area. The attached garage adds everyday convenience, while central air and forced-air heat keep you comfortable year-round. Set on a quiet, tree-lined street with easy access to shopping, dining, and commuter routes, this move-in-ready home won't last. Schedule your private showing today!

1338 Avon Blvd, Cheshire

$750,000

3 Beds ⋅ 4 Baths ⋅ 24202169 MLS

Welcome to this spectacular Cape Cod home, where timeless charm meets modern updates and breathtaking mountain views. The beautifully renovated chef's kitchen features custom cabinetry, abundant drawers, and thoughtful storage. Enjoy meals while taking in views of the scenic backyard and peaceful surroundings. A standout feature is the newly updated 345 sq. ft. screened porch with attractive flooring and ceiling fans, creating the perfect space for morning coffee, afternoon tea, or evening relaxation overlooking the tranquil koi pond. The flexible floor plan includes a spacious dining room, den, study/music room, and private four-season room. A first-floor full bath, one of four full baths in the home, adds convenience. Additional highlights include three fireplaces (two wood-burning and one gas), three-zone heating, central air, and newer windows throughout. Major improvements completed within the last 16 years include the roof, furnace, central air system, and primary bath, providing peace of mind for years to come. Outside, the impressive grounds offer stunning views and a serene natural setting. Four garages provide exceptional space for vehicles, storage, workshops, and hobbies. Adding to the property's unique appeal is the original barn from the 1957 home, complemented by established gardens and expansive outdoor space. Ideal for artists, gardeners, and hobbyists, this remarkable property offers comfort, versatility, and natural beauty in an exceptional setting.

775 Mountain Rd, Cheshire

$725,000

5 Beds ⋅ 5 Baths ⋅ 24201342 MLS

Fabulous oversized Colonial tucked away at the end of a quiet cul-de-sac in southern Cheshire! Lovingly maintained by its original owners since 1997, this home has so much to offer! A welcoming two-story foyer opens to a formal Living Room with French doors leading to a formal Dining Room. The large Eat-in-Kitchen features Corian countertops, island with cooktop, and sliders to the backyard. A generous open-concept Family Room with vaulted ceilings and woodburning fireplace makes the perfect place to relax or entertain. A dedicated home office, Laundry Room and Half Bathroom complete the main level. Upstairs, five generously sized Bedrooms provide exceptional flexibility. The spacious Primary Suite features a Full Bathroom and walk-in closet, while two additional Full Bathrooms conveniently serve the remaining four Bedrooms. The finished lower level takes entertainment to another level with an equipped home theater, wet bar, huge flex space with built-ins, and a Half Bathroom. The park-like, level backyard is your own private oasis boasting a lovely 20 x 40 in-ground pool and an enormous ground-level deck. Updates and amenities include: central air conditioning; public water and sewer; Tesla solar Power Purchase Agreement; roof (2018); 200 amp electrical system; whole house generator; 4 HVAC zones; 2 car attached garage; central vacuum; pool liner (2018); propane line to grill; and underground irrigation system. 80 Autumn Court is the perfect place to call home!

80 Autumn Ct, Cheshire

$1,999,000

4 Beds ⋅ 2 Baths ⋅ 24203800 MLS

They are not making anymore land! Owner motivated to pass this beautiful property to a new owner! This colonial is situated on a 25.5 acres of rolling fields and wooded property. Offering includes house lot MBL 8-2 and MBL 1-2. Behind this property is hundreds of acres of town owned land. Great property to either use as a estate with lots of land, farming, maybe a few extra lots, or try to change zone for something else... Situated next to I-84 for great visibility. Inquire with listing agent for more info.

1827 Marion Rd, Cheshire

$529,900

2 Beds ⋅ 3 Baths ⋅ 24203640 MLS

Tucked well back from the road on 4.13 beautiful acres, this inviting Raised Ranch offers a peaceful, private setting surrounded by nature and lovely garden areas. The home features 1,234 sq. ft. on the main level plus an additional 576 sq. ft. of beautifully finished living space in the walk-out lower level. The light and bright main level features a beautifully updated kitchen with white cabinetry and center island, open to the dining area with sliders leading to a spacious deck with awning-the perfect spot to relax and enjoy the serene surroundings. A sun-filled living room, two bedrooms and two full baths complete this level. The generously sized primary bedroom features its own private full bath. The finished walk-out lower level offers additional flexible living space with built-ins, a half bath and laundry area-ideal for a family room, home office, gym or guest space. Set back among the woods with plenty of privacy and beautiful natural surroundings, this special property is a wonderful retreat for nature lovers while still offering the convenience of Cheshire living. Come see the beauty of what the town of Cheshire offers with its open space, Roaring Brook Falls, The Farmington Canal Heritage Trail, Parks & Outdoor Recreation. Offering several retail districts that feature a variety of shops and restaurants including Whole Foods, Starbucks, Barnes & Noble. Seller to find suitable housing.

225 Timber Ln, Cheshire

$455,000

3 Beds ⋅ 1 Baths ⋅ 24203408 MLS

Welcome to 445 Lincoln Drive in Cheshire! This beautifully remodeled home offers the perfect blend of modern updates and comfortable living. Step inside to discover a bright, inviting interior featuring a renovated kitchen with stylish finishes, an updated bathroom, and thoughtful improvements throughout. The finished lower level provides valuable additional living space-perfect for a family room, home office, gym, playroom, or guest area. Whether you're entertaining friends or enjoying a quiet evening at home, this move-in-ready property offers the flexibility and comfort today's buyers are looking for. Conveniently located near shopping, restaurants, parks, and major commuter routes, this is a wonderful opportunity to enjoy all that Cheshire has to offer.

445 Lincoln Dr, Cheshire

$449,900

3 Beds ⋅ 2 Baths ⋅ 24202606 MLS

Settle right into this thoughtfully maintained Cheshire Farmhouse Cape, where classic character, smart updates, and an unexpectedly flexible layout come together on a beautiful .81-acre lot. Hardwood floors and abundant natural light carry through the main level, highlighted by a fireplaced living room, dining area, and updated kitchen with stainless appliances, generous cabinetry, and breakfast-bar seating. A first-floor bedroom, full bath, and dedicated home office with closet create valuable flexibility for guests, work-from-home needs, or single-level living. Upstairs boasts two spacious bedrooms and a second full bath. Outside, the newer wraparound front porch adds standout curb appeal, while the expansive level yard, stone patio, garage, and shed offer room to entertain, garden, play, or simply enjoy the setting. Major updates include a new roof plus new boiler, water heater, and oil tank. Enjoy all that Cheshire has to offer, including award-winning schools, the new Whole Foods Market, Route 10 shopping and restaurants, the Farmington Canal Heritage Trail, Sleeping Giant State Park, and convenient access to I-691, I-84, and the Merritt Parkway.

137 Harrison Rd, Cheshire

$1,379,000

5 Beds ⋅ 5 Baths ⋅ 24202325 MLS

Discover this truly exceptional custom Colonial home, distinguished by its thoughtful design, custom millwork, architectural details, and masterful craftsmanship both inside and out, situated on a desirable 2.37 acres corner lot in one of South Cheshire's most sought-after areas. Custom wrought iron gates welcome you into this warm, inviting home, flooded with natural light from the abundant large windows, skylights, and French doors. The heart of the home is the beautifully remodeled kitchen, with its expansive center island offering both exceptional functionality and a wonderful gathering space. The kitchen flows into the spacious family room which provides easy access to the covered porch, allowing effortless, comfortable daily living and entertaining. The first-floor primary bedroom provides convenience and privacy, while three large bedrooms upstairs offer generous space for all. Enjoy year-round sunshine in both the four-season terrace room and the separate sunroom, that bring the outdoors in. Versatile finished space with a full bath above the garage, offers possibilities for home offices, studio, recreation room, and more. The exceptional outdoor setting offers a resort-like experience, the covered rear porch featuring a raised cedar ceiling, skylights, and terracotta tile, provides an inviting gathering space. Follow the path through the gardens to the heated in-ground Gunite swimming pool and hot tub, creating your own retreat for relaxation and entertaining!

885 S Brooksvale Rd, Cheshire

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