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

$771,900

3 Beds ⋅ 3 Baths ⋅ 24216806 MLS ⋅ The Reserve At Stonebridge Crossing BLDG.

FINAL NEW CONSTRUCTION OPPORTUNITY AT THE RESERVE AT STONEBRIDGE CROSSING! Ready for immediate occupancy, this beautifully appointed carriage home offers the last opportunity to become an original homeowner in this sought-after Cheshire community. Featuring nearly 3,000 square feet of finished living space, this thoughtfully designed home combines luxury finishes, architectural appeal, and the convenience of low-maintenance living. A dramatic two-story great room with soaring ceilings and abundant natural light anchors the open-concept main level, complemented by engineered hardwood flooring and a beautifully upgraded Pro Kitchen featuring ceiling-height cabinetry, granite countertops, a 36-inch JennAir induction range, farmhouse sink, custom coffee bar, and wine refrigerator. The first-floor primary suite offers a spacious walk-in closet, spa-inspired bath with oversized tiled shower, and convenient main-level laundry. Upstairs, an open loft overlooks the great room and connects two additional bedrooms, a full bath, private home office, and second laundry room. The finished lower level adds approximately 525 square feet of flexible recreation space and an additional full bathroom. Built to EG Home's Zero Energy Ready standards, this home includes solar panels, high-efficiency heating and cooling, advanced insulation, and enhanced indoor air filtration. Enjoy community amenities including walking trails, a pavilion, and fire pit, with convenient access to every day living.

27 Soderman Way Unit 27, Cheshire

$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

$425,000

2 Beds ⋅ 3 Baths ⋅ 24214748 MLS ⋅ Quarry Village BLDG.

Step inside this stunning, fully updated end-unit condo, offering an exceptional blend of style, comfort, and modern finishes throughout! The impressive living room features soaring vaulted ceilings, a skylight that fills the space with natural light, and a beautiful wood-burning fireplace with a honed granite hearth and surround. French doors lead directly to a spacious deck overlooking the backyard, perfect for relaxing or entertaining. The fully renovated kitchen is a showstopper, featuring custom cabinetry, a center island, and gorgeous quartz countertops, flowing seamlessly into the spacious dining area. Luxury vinyl flooring extends throughout the main level, creating a warm and cohesive feel. The beautifully appointed bathrooms feature custom Birch vanities, quartz countertops, and elegant brass fixtures. Upstairs, you'll find a spacious primary bedroom with a walk-in closet, abundant natural light, and a stunning private bathroom featuring a custom vanity and oversized walk-in shower with marble surround and glass doors. The additional full bathroom is equally impressive, offering a luxurious soaking tub with marble surround and porcelain tile flooring. Luxury vinyl flooring continues throughout the second level. The large unfinished basement provides plenty of storage space and features an existing basement water management system. Additional highlights include a newer furnace, central air conditioning, and hot water heater.

72 Quarry Village Rd Unit 72, 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

$230,000

2 Beds ⋅ 3 Baths ⋅ 24214604 MLS ⋅ Deepwood BLDG.

Enjoy the convenience of townhouse living with the space and comfort of home in Cheshire's Deepwood community. This two-bedroom condo offers 1 full and 2 half baths, hardwood floors, crown molding, and a kitchen with granite countertops. Spacious living and dining areas welcome you on the main level, while upstairs features two generously sized bedrooms with hardwood floors, an updated full bath, and convenient laundry. The finished, heated lower level adds approx. 304 sq. ft. of living space with a family room, half bath, and separate unfinished storage area. Step outside and enjoy access to backyard open space, a welcome feature that adds to the home-like setting. Improvements include a new roof (October 2026), & anticipated paving. Air-conditioning units and two assigned parking spaces add everyday convenience. Access to Farmington CanalHeritage Trail, and nearby shopping, restaurants, and commuter routes including I-691 and I-84.

420 Robin Ct Unit 420, 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. First showings begin Saturday 10/17- bring your best offer!

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

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Cheshire Real Estate

Newest Listings in Cheshire

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