Cheshire Real Estate

Welcome to Cheshire, Connecticut – a charming town that perfectly blends suburban tranquility with vibrant community spirit. Nestled in New Haven County, Cheshire is renowned for its picturesque landscapes, top-notch schools, and a welcoming atmosphere that makes it a sought-after destination for families and professionals alike.

With a population of just over 29,000 residents, Cheshire boasts a close-knit community that takes pride in its rich history and well-maintained neighborhoods. The town is dotted with beautiful parks, including the expansive Cheshire Park, where residents can enjoy walking trails, sports fields, and picnic areas. The scenic beauty of Cheshire is complemented by its historic downtown, featuring a delightful mix of local shops, cafes, and restaurants that cater to diverse tastes.

Education is a cornerstone of the Cheshire community, with highly-rated public schools that consistently rank among the best in the state. Families are drawn to the area for its commitment to quality education and the numerous extracurricular opportunities available to children.

Cheshire also offers convenient access to major highways, making commuting to nearby cities like New Haven and Hartford a breeze. Whether you're looking for a peaceful retreat or an active lifestyle, Cheshire provides the perfect balance.

In addition to its local charm, the town hosts various community events throughout the year, fostering a strong sense of belonging among residents. From farmers' markets to seasonal festivals, there's always something happening in Cheshire.

Discover the allure of Cheshire, where small-town charm meets modern living, and experience the warmth of a community that feels like home.

Newest Listings in Cheshire

$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

$229,000

24204296 MLS

Your blank canvas - with a head start A rare opportunity to build the home you've been picturing on a 1.84-acre lot in Cheshire. The existing structure will be removed prior to closing - or within 60 days of closing at the latest - leaving you a cleared, ready-to-build site with the foundation remaining in place. That foundation is the difference-maker. Pouring a new foundation is one of the most expensive and time-consuming early phases of any new build. Here, that groundwork is already done, which can meaningfully cut cost and shave weeks off your construction timeline. Bring your own plans and builder, or design around the existing footprint. Why this lot Foundation already in place - a substantial cost and schedule advantage over a raw lot Building to be removed - the site will be cleared, so you start with a clean slate above grade Private well and septic - no dependency on municipal water/sewer hookups R-80 zoning - single-family residential 1.84 acres of space to design around

1116 Wallingford 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

24203808 MLS

They are not making anymore land! MAKE OFFER! 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

$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

$199,000

2 Beds ⋅ 1 Baths ⋅ 24203224 MLS ⋅ Birchwood BLDG.

Stylish, beautifully renovated and filled with natural light, this end-unit condominium is located in the well-maintained Birchwood community, surrounded by expansive green space and ample parking. Beautiful, move in condition! The open floor plan offers two spacious bedrooms, a large living room, and a stylish white kitchen with granite countertops, self-closing cabinets with lighting and stainless steel appliances. The beautifully remodeled bathroom features modern tile, a contemporary vanity, and a glass-enclosed shower. Additional amenities include a large private storage unit and shared laundry in the basement. The HOA fee covers water, heat, hot water, management, grounds and road maintenance - truly exceptional value. With no current special assessments and strong association reserves, this home provides peace of mind and affordability. Enjoy a prime Cheshire location with access to Farmington Canal Trail just minutes from excellent restaurants and charming cafes. New Stonebridge shopping center features Whole Foods, Barnes & Noble, TJ Maxx, J. Crew and other popular retailers. This is a wonderful opportunity to own a truly beautiful home and enjoy easy, no-maintenance living in one of Connecticut's most desirable towns with very good school system.

502 Oak Ave Unit 17, Cheshire

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