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

$389,900

2 Beds ⋅ 1 Baths ⋅ 24214222 MLS

Welcome to 45 Broadview Road, a charming ranch with easy one-level living on a level 0.48-acre lot in a convenient Cheshire neighborhood. Hardwood floors run through the main level, where the bright living/dining room centers on a brick fireplace with an insert. The updated kitchen has Corian counters, a skylight, a pantry and plenty of cabinet space. Two bedrooms, the second ideal as a home office, and a tiled full bath complete the main level, with ceiling fans throughout. Downstairs, the finished family room with a wood stove adds cozy living space, along with laundry, a workshop and abundant storage. A floored attic with pull-down stairs offers even more room. A brand-new roof is being installed in early November 2026. Other features include an attached one-car garage with an automatic opener, 200-amp electrical service, wood shingle siding, city water and sewer, oil heat, 1992 Steam Boiler and a 2012 indirect hot water heater. Outside, relax on the oversized deck with a hot tub, or enjoy the patio and gazebo. The beautifully landscaped yard is filled with unusual plants, mature trees and established gardens, and two sheds give you plenty of space for tools and equipment. This sweet, well-loved home offers character and possibilities for its next owner. It's close to Cheshire's shops, restaurants and parks, and you can walk to the Farmington Canal Heritage Trail and town. Come take a look!

45 Broadview Rd, Cheshire

$675,000

4 Beds ⋅ 3 Baths ⋅ 24215798 MLS

Welcome to 35 Brookside Place, a spacious and inviting four-bedroom Colonial offering comfortable living, thoughtful updates, and exceptional spaces for entertaining. Set on a beautifully landscaped property in Cheshire, this home combines classic New England charm with the features today's buyers appreciate. Step inside to discover a versatile floor plan with generous living areas, hardwood flooring, and abundant natural light. The welcoming living room features a beautiful bay window, while a separate den with a fireplace provides a cozy place to relax. The updated eat-in kitchen is the heart of the home. Sliding glass doors lead to one of the property's most distinctive features-a spectacular sunroom with soaring curved wood framing and expansive glass walls and ceiling. Filled with natural light and overlooking the backyard, this wonderful space is perfect for morning coffee, entertaining, or simply enjoying the changing seasons. Upstairs, four generously sized bedrooms provide comfortable accommodations, including a spacious primary bedroom with ample closet space and ensuite bathroom. Another full bathroom completes the second level, while a convenient half bath and laundry area are located on the main floor. The finished lower level adds additional square feet of flexible recreation space.

35 Brookside Pl, Cheshire

$519,900

3 Beds ⋅ 2 Baths ⋅ 24215666 MLS

Welcome to this beautifully updated 3-bedroom, 2-bath Ranch located in a quiet neighborhood in Cheshire's desirable south end! This inviting home offers a bright, open floor plan featuring hardwood floors, crown molding, and a spacious living and dining area. The updated kitchen boasts white cabinetry, granite countertops, and stainless steel appliances, while the comfortable family room features a cozy fireplace. The primary bedroom includes a beautifully updated ensuite bath. Additional highlights include custom closet built-ins and custom window shades throughout the home. A partially finished lower level provides flexible space for a home office, gym, or recreation room, along with laundry and access to the 2-car garage. Enjoy outdoor entertaining on the deck overlooking the level backyard. Conveniently located near schools, parks, shopping, restaurants, and major highways. Move-in ready and a must-see!

120 Hilltop Rd, Cheshire

$479,900

4 Beds ⋅ 5 Baths ⋅ 24216201 MLS

Investors and Contractors take notice. This 3,839 Colonial is ready to be brought back to life. Features include a huge Family Room with cathedral ceilings and a fireplace with an open floor plan that includes the large eat-in kitchen, dining area, and slider to the back deck. Town shows this as a 3 bedroom home but easily can be 4 or 5 bedroom depending on how you use the other rooms. Outside there is an inground pool with spa and outdoor kitchen area. Prior water damage led to this property being stripped to the studs awaiting your custom re-build. As-Is Sale.

7 Edith Pl, Cheshire

$839,900

4 Beds ⋅ 3 Baths ⋅ 24214742 MLS

This stunning home feels brand new, with extensive updates and impeccable attention to detail. Newly refinished HW floors, fresh paint including ceilings, newer roof and siding, and beautifully remodeled kitchen and baths make this home move-in ready. The custom kitchen features new cabinetry, quartzite countertops, stainless steel appliances, a center island, built-in desk area, spacious dining space, skylights that bring in morning sun, and one of the home's three fireplaces. The dining space of the kitchen showcases a vaulted cedar-lined ceiling, more skylights, and a beautiful copper fireplace. Just off the kitchen, the family room has a dramatic vaulted ceiling, palladium windows, built-in bookshelves, and another fireplace. The inviting living room offers a decorative fireplace, custom built-in bookcases, and French doors leading to a sun-filled all-season room with a propane stove. A convenient 1st floor laundry room adds everyday practicality. Upstairs, you'll find 4 updated bedrooms, including a spacious primary suite with a remodeled bath, along with a fully renovated guest bathroom. Outdoor living is equally impressive, featuring an expansive brick patio overlooking a lush lawn and established perennial gardens, creating the perfect setting for relaxing, entertaining, and enjoying the seasons. Located in Cheshire's desirable Beacon Hill neighborhood, this exceptional home offers timeless charm with modern updates in one of the town's most sought-after settings!

256 Beacon Hill Dr, Cheshire

$469,000

4 Beds ⋅ 3 Baths ⋅ 24214579 MLS

Welcome to 68 Pleasant Drive, where a potential in-law suite with its own private entrance offers flexibility for extended family or guests. Hardwood floors, a spacious floor plan, and a convenient Cheshire location create a wonderful place to call home. Sidewalks line the road, adding to the appeal of this walkable setting close to shopping and local restaurants. The large backyard offers plenty of room for outdoor entertaining, gardening, or simply relaxing in privacy. Enjoy space, versatility, and everyday convenience in an established neighborhood. Showings begin tomorrow! NOTE: the square footage reflected in the MLS is based on town assessor records. SELLER BELIEVES it may not accurately represent the home's actual living space. The property offers additional living area beyond what is recorded. Buyers and their agents are encouraged to independently verify total square footage.

68 Pleasant Dr, Cheshire

$589,900

3 Beds ⋅ 2 Baths ⋅ 24213428 MLS

CHARMING CHESHIRE CAPE ON A NEAR-ACRE LOT - welcome to 178 Harrison Road, a well-loved three-bedroom, two-bath Cape Cod set on 0.97 lightly-wooded acres in a quiet, tree-lined neighborhood. The kitchen features granite counters, stainless appliances and timeless brick accents, flowing seamlessly to a sun-filled eat-in dining area with vaulted ceiling and walls of windows framing peaceful views of the private backyard. Multiple distinct living spaces give you room to spread out: a formal living room with tile-surround fireplace, a cozy family room with pellet stove, and a formal dining room with built-in cabinets. Hardwood flooring throughout the first-floor living areas. Three generous bedrooms including a main-floor primary, two full baths, and 2,054 square feet above grade, plus a built-out finished lower level ideal as a home gym, playroom, or office. Major capital improvements already addressed: 2024 ROOF, 2025 OWNED solar panels (no lease/loan to transfer), 2021 HVAC/Central Air, 2023 chimney liner, and underground irrigation. Oversized 2-car under-house garage offers abundant storage. Step outside to a versatile outdoor retreat with zones for every season - generous back deck, flagstone patio at the front entrance, dedicated children's play area with playscape, and plush lawn framed by stacked stone retaining walls and mature landscaping. Short distance to Cheshire schools, parks, and shopping. DONT MISS OUT!

178 Harrison Rd, Cheshire

$579,900

4 Beds ⋅ 3 Baths ⋅ 24213826 MLS

Welcome to 450 Cardinal Lane! This well-maintained 4-bedroom, 2.5-bath Colonial offers 2,042 square feet of living space on a beautifully landscaped .46-acre lot in Cheshire. The spacious first floor features a large living room, formal dining room, and a beautifully remodeled kitchen with white cabinetry, stainless steel appliances, and a comfortable eat-in area. Just off the kitchen is the inviting family room with a fireplace, access to the attached two-car garage, and direct access to the backyard. You'll also appreciate the convenience of an updated half bath on the main level. Upstairs, you'll find a generously sized primary bedroom with direct access to the full hall bathroom, along with three additional bedrooms. Hardwood flooring throughout adds warmth and character to the home. The partially finished lower level offers plenty of storage space, laundry area and a second full bathroom that has not been used in many years. Step outside to enjoy the beautiful, oversized patio overlooking the private, nicely manicured backyard, perfect for outdoor entertaining, dining, or simply relaxing. Additional highlights include a two-car attached garage with new door openers, replacement windows (2017), a brand-new roof (2026), and a newer oil tank (2020). Conveniently located near Cheshire's shopping, restaurants, parks, and recreational amenities, this lovely home offers a wonderful combination of space, comfort, and location. Don't miss this opportunity to make it your own!

450 Cardinal Ln, Cheshire

$599,900

3 Beds ⋅ 3 Baths ⋅ 24213120 MLS

Welcome to this spacious 2,280 sq ft Ranch in the desirable Nob Hill area! This inviting home offers steel beam construction, C/A, two-zone heating and beautiful views. The kitchen features granite countertops, tile floors, a breakfast bar, cooktop, stainless steel appliances and opens to the family room with HW floors and gas fireplace with an impressive brick wall. Enjoy the scenic views from the screened-in porch! The dining room features HW floors and wainscoting. The spacious living room offers a gas fireplace, built-ins, recessed lighting, and a large picture window overlooking the backyard, with potential for a home office. The primary bedroom boasts HW floors and an impressive 14 x 6 walk-in closet with shelving and recessed lighting. The primary bath features double-sink vanity with marble top. Two additional bedrooms feature HW floors. The updated main bath has double sinks. Additional highlights include a tiled foyer, large closet, mudroom with washer + dryer, updated half bath, and large pantry. The expansive walk-out lower level features a wood-burning fireplace and wet bar, perfect for recreation. Enjoy the fenced backyard and patios. Other features include: replacement windows, whole-house fan and pull-down attic. Updates include roof and chimney (2025), refrigerator and dishwasher (2024), washer and dryer (2023), and garage door and back entry door (2019). Public water and sewer in the street. A wonderful opportunity in a sought-after location!

256 Nob Hill Rd, Cheshire

$499,999

3 Beds ⋅ 3 Baths ⋅ 24213257 MLS

Come and see this terrific home in an ideal central Cheshire location in a sidewalked neighborhood next to Highland Elementary. Enter this terrific home and be welcomed by gorgeous hardwood floors, an updated modern kitchen with doorway to large 16x20 rear deck, dining room and living room with fireplace. The primary bedroom has a half bath, 2 additional bedrooms and a full bathroom complete the 1st floor. The lower level features a light and bright recreation room with walk out to the back yard, a full bathroom with shower and laundry, an office/flex use room, and utility/storage area. The rear yard features a 13.5x21 covered paver patio for enjoying your summer afternoons in the shade. Home is wired for a generator (included), 200 amp upgraded electrical, central air conditioning, new garage door opener, and much more.

268 Eastgate Dr, Cheshire

$415,000

2 Beds ⋅ 1 Baths ⋅ 24212500 MLS

Welcome to 1016 Sperry Road, a charming Cheshire ranch set on approximately 1.21 acres. This inviting home features beautiful hardwood floors throughout and offers the ease of one-level living. The garage underneath provides convenient parking and additional storage space. Step outside and discover your own private backyard oasis-a wonderful setting for relaxing, entertaining, gardening, or simply enjoying the peaceful surroundings. The expansive lot offers plenty of space to create the outdoor retreat you've always envisioned. Located in desirable Cheshire, this property offers a wonderful opportunity for buyers seeking a home with character, hardwood floors, generous outdoor space, and room to make it their own. Come see the possibilities at 1016 Sperry Road!

1016 Sperry Rd, Cheshire

$349,999

3 Beds ⋅ 2 Baths ⋅ 24211856 MLS

Welcome to 50 Saint Joseph Street, a charming brick Cape Cod offering 3 bedrooms, 1.5 baths and 1,573 square feet of living space in a convenient Cheshire location. Classic New England character meets a comfortable, functional layout featuring a bright living room with fireplace, an open kitchen and dining area, and flexible living space across two levels. The distinctive brick exterior, mature landscaping and established residential setting give this home plenty of curb appeal. Just minutes from Cheshire's popular Route 10 corridor, enjoy convenient access to local favorites including Viron Rondo Osteria, Mercato, Butcher Bros Steakhouse, and Fuoco Apizza, along with shopping and everyday necessities. Outdoor recreation is also close by, including the Farmington Canal Heritage Trail and Cheshire's many parks and recreational amenities. In addition, convenient access to I-691 makes travel throughout central Connecticut easy. A wonderful opportunity to own a classic brick Cape and enjoy everything Cheshire has to offer.

50 Saint Joseph St, Cheshire

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Cheshire Homes for Sale

Newest Cheshire Homes for Sale

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