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

$275,000

2 Beds ⋅ 2 Baths ⋅ 24194452 MLS

Being sold AS IS WHERE IS. Opportunity awaits in this well-built 2-bedroom home located in a desirable neighborhood. Featuring a bright and spacious family room filled with natural light, this home offers a comfortable layout and solid bones ready for your personal vision. The roof was replaced in 2017, providing a great start for future improvements. While the home would benefit from modern updates, it offers tremendous potential for homeowners, investors, or anyone looking to build equity. Conveniently located close to local amenities, this property is ready for its next chapter. Bring your ideas and make it your own!

185 Green Hill Ln, Cheshire

$849,900

4 Beds ⋅ 3 Baths ⋅ 24194347 MLS

Coming Soon, showings start Wednesday! More pictures coming soon. Stately home set on just under 2 acres in a beautiful country setting. Built from the foundation up in 2006, this home offers soaring ceilings, flowing rooms and space for everyone! The welcoming foyer leads to the dining room highlighted by a fireplace with pellet stove insert, and the living room beyond - both with hardwood floors. A balcony from the upper level looks down on the kitchen with high ceilings, dramatic chefs vent, beautiful granite countertops and new refrigerator. Also included on the main level is an office, a bedroom that can be utilized as a den, and a laundry room that leads to the huge three car garage. Upstairs you'll find three large bedrooms with new LVP flooring, including the primary suite with walk-in closet and spa bath with whirlpool tub. Another office, another full bath and a bright reading nook complete the upper level. The lower level is semi-finished (no heat) to offer more room to spread out. Numerous updates include a brand new roof (2026), new driveway (2025), new well tank, newer washer and dryer, and an electric car charger in the garage. Welcome Home!

662 Coleman Rd, Cheshire

$559,900

4 Beds ⋅ 3 Baths ⋅ 24194294 MLS

Nestled in one of South Cheshire's most sought-after neighborhoods, this spacious home offers endless potential and an unbeatable location. Enjoy sidewalks throughout the neighborhood, just steps from the brand-new Norton Elementary School and the Farmington Canal Linear Trail. The updated kitchen features granite countertops, a breakfast bar, and opens seamlessly to the dining area and expansive family room, creating the perfect open-concept living space. The inviting family room includes a fireplace and leads to a three-season sunroom with cathedral ceilings, skylights, a ceiling fan, and peaceful views of the large, level backyard. The first floor also offers an updated half bath, a versatile den with a laundry closet, and a private office with built-in shelving. Upstairs, you'll find four bedrooms with hardwood flooring throughout (including beneath the hallway carpet). The primary suite features a full bath, while a second full bath serves the remaining bedrooms. Major updates include an energy-efficient heat pump with central air installed approximately 10 years ago and a roof that is only 5 years old. Bring your vision and make this wonderful home your own in a neighborhood you'll love for years to come!

341 Sharon Dr, Cheshire

$650,000

4 Beds ⋅ 3 Baths ⋅ 24192046 MLS

Nestled in one of Cheshire's most sought-after neighborhoods, 46 Dundee Drive puts you just steps from Barnum School, a rare convenience for growing families. From the moment you arrive, it's clear this home has been meticulously refreshed from top to bottom: fresh paint throughout, brand-new carpet on the staircase and entire second floor (except two bedrooms), and a fully renovated basement featuring sleek new LVT flooring, ready to flex as a playroom, home office, or media retreat. The kitchen shines with all-new appliances, making meal prep feel like a pleasure, not a chore. Peace of mind comes standard with a new roof installed in 2024, so the big-ticket items are already behind you. Whether you're right-sizing, starting out, or simply ready for something turnkey, this home checks every box. Priced to move and positioned for a quick close. Schedule your private showing today.

46 Dundee Dr, Cheshire

$475,000

3 Beds ⋅ 2 Baths ⋅ 24187815 MLS

This expansive Cape Cod is filled with charm, character, and plenty of space to make your own. The spacious eat-in kitchen offers abundant storage and cooking space, along with flexible room for a dining table, breakfast bar, or both. Step outside to the large Trex deck, where you can enjoy your morning coffee while overlooking the private, peaceful wooded yard. A charming screened porch provides another relaxing spot to read, unwind, or simply enjoy the sounds of nature. The main level includes a generously sized front-to-back living room with a propane fireplace, as well as a spacious dining room that could also serve as a home office, playroom, or additional sitting area. Upstairs, you'll find three bedrooms and a full bath. The finished lower level offers an inviting family or recreation room, along with an additional flexible space ready to suit your needs. Outside, the property includes a hot tub, two storage sheds, and plenty of yard space for entertaining, gardening, or future expansion. This special home offers comfort, versatility, and wonderful indoor and outdoor living spaces.

479 Blacks Rd, Cheshire

$449,900

3 Beds ⋅ 2 Baths ⋅ 24187993 MLS

Highest and Best due by 5 pm Sunday 7/26. Welcome home to this well-maintained home offering comfort, convenience, and thoughtful updates throughout. The inviting family room features a cozy Vermont Castings wood stove, while mini-split systems provide efficient air conditioning on the first floor. Enjoy summer days in the 24' round above-ground pool (54" deep) with an deck that's just 5 years old, perfect for entertaining. Recent improvements include Andersen replacement windows, a new boiler, 2022 Smart indirect hot water tank, upgraded 200-amp electrical service, new oil tank, insulated Bilco basement door, and a 2-year-old driveway. A Generac whole-house generator (2021), fueled by leased propane, provides added peace of mind. With open fields directly across the street, this home offers enhanced privacy, beautiful open views, and the opportunity to enjoy birds, deer, and other local wildlife right from your front yard. Conveniently located within walking distance of Doolittle School and the Farmington Canal Heritage (Linear) Trail, with easy access to I-91 and I-84 for commuting. Shopping, dining, and everyday conveniences are just minutes away.

460 Oak Ave, Cheshire

$779,000

4 Beds ⋅ 3 Baths ⋅ 24190019 MLS

Exceptional, beautifully built, updated and maintained, custom center hall Colonial on over 1 acre of private, professionally maintained gardens and yard. Property abuts open space. Bluestone steps and stone walls surround this magnificent home. Hardwood floors throughout. Newer granite, tiled kitchen features large island,wet bar, wine cooler and window seat with storage. Kitchen by Gedney. Family room has white-washed brick, propane fireplace, built in cabinetry and slider to large deck. Front and rear paver walkways with stunning gardens. First floor laundry (12x9) has sink, under counter washer/dryer, built in hamper and ironing board. Formal living room (currently used as office)and formal dining room. Primary bedroom has remodeled bath with shower. 3 additional generous bedrooms and remodeled full bath. Lower level has 2 carpeted rooms and fabulous wine cellar. Lower level has its own heat/ac zone 3 zones). Pull down stairs in garage for extra storage.

19 E Ridge Ct, Cheshire

$1,748,600

6 Beds ⋅ 7 Baths ⋅ 24190202 MLS

Welcome to The Cheshire Estate on Whispering Hollow Court. Set on a private 1.84-acre lot in an intimate enclave of homes on a cul-de-sac, this modern brick Colonial offers over 10,000 sf of living space across three levels - a rare opportunity to live comfortably and entertain often. The two-story great room anchors the main level, with French doors opening to the patio, outdoor kitchen, and pool for effortless indoor/outdoor entertaining - enjoy quiet mornings by the water and evenings out back to socialize. The main level also features the primary suite, complete with a private sitting room and fireplace - a true retreat at the end of the day - along with a sunroom and a wood-paneled study. The finished lower level adds a home gym and an indoor basketball court, convertible to a squash or racquetball court, so game nights and workouts happen without ever leaving home. Adding rare flexibility, a semi-private au pair apartment (approx. 40' x 22') includes its own kitchen, full bath, living room, and bedroom - ideal for extended family, live-in help, or guests who want their own space to come and go as they please. This isn't just a home - it's a lifestyle built around space, privacy, and the freedom to live exactly how you want.

25 Whispering Hollow Ct, Cheshire

$615,000

3 Beds ⋅ 2 Baths ⋅ 24191300 MLS

Need serious garage space? This property features a brand-new commercial-sized detached garage that's ideal for collectors, mechanics, contractors, landscapers, hobbyists, or anyone looking for exceptional storage or workspace. Welcome to 722 Allen Avenue, Cheshire! This beautifully updated 3-bedroom, 2-bath ranch is set on a level 1-acre lot with public water and public sewer and offers the perfect blend of comfort, flexibility, and exceptional space. The open floor plan features a spacious living room with hardwood floors and a fireplace, a dining room with hardwood flooring, and an updated kitchen that flows seamlessly into the main living areas. The primary suite offers a cathedral ceiling, private full bath, and convenient first-floor laundry. Two additional bedrooms and a full hall bath complete the home. Additional features include a family room with access to the attached 2-car garage, a walk-up attic, and an oversized screened-in porch overlooking the private backyard. The true standout feature is the brand-new commercial-sized detached garage with electric. With updated kitchen and baths, hardwood floors, one-level living, an oversized detached garage, and a desirable Cheshire location, this unique property offers endless possibilities - must-see!

722 Allen Ave, Cheshire

$561,885

4 Beds ⋅ 3 Baths ⋅ 24189652 MLS

Welcome to this beautifully maintained Colonial, ideally situated in a sought-after neighborhood featuring underground utilities and sidewalks. From the inviting front porch to the private backyard, this home offers timeless charm and exceptional value. The first floor features gleaming hardwood floors throughout, a spacious living room with a cozy fireplace, and a formal dining room with two classic built-in corner hutches. A sliding glass door opens to a tranquil, tree-shaded patio overlooking a beautifully landscaped backyard with privacy fencing-perfect for relaxing or entertaining. Upstairs, you'll find four generously sized bedrooms, each equipped with ceiling fans. Additional updates include a roof that's only six years old, a brand-new hot water heater and furnace, plus the peace of mind of a whole-house Kohler generator for year-round comfort and security. A unique buying opportunity: This property is currently subject to an Affordable Housing Restrictive Covenant that is scheduled to expire in approximately three years. The current list price reflects the maximum allowed for a CHFA-financed purchase and CHFA buyers must meet applicable CHFA income guidelines. Other option is 80 per cent of State of CT median income guidelines. Cash buyers are also eligible to purhase property within certain income restrictions. See Attachment for Restrictive Covenant. Some notice required for showing.

88 Dundee Dr, Cheshire

$1,711,500

4 Beds ⋅ 5 Baths ⋅ 24190982 MLS

Lovely contemporary Colonial set on 2.26 acres offers over 6,000 square feet of above-grade living space w/ a versatile multi-level layout. Step into the dramatic two-story brick foyer featuring floor-to-ceiling windows, & radiant floor heating throughout the 1st floor. This level offers outstanding add'l living space w/ a comfortable family room, 43' x 15' rec room, private office, full BA, & walkout access to the covered lower deck. Whether you're looking for a home gym, guest retreat, or simply extra space to spread out, you have endless possibilities! The main living level features a large kitchen w/granite countertops, center island, quality appliances, & sunny breakfast nook with lots of windows overlooking the peaceful landscape. Dining room, living room, & vaulted Great Room w/ pellet stove provide inviting spaces for everyday living & entertaining. Upper deck is conveniently accessible from the breakfast nook or great room. The primary suite features radiant floor heating, en-suite BA, double closets, & walk-in closet. 1/2 BA w/ laundry completes this level. Upstairs you'll find 3 generously sized BRs, including one w/ its own private BA, plus an additional full BA. Backing directly to Cheshire Land Trust, this property offers exceptional privacy, a putting green, pickleball court, & peaceful views from nearly every room. Whether enjoying your morning coffee on the deck or relaxing indoors, the natural setting has a sense of tranquility that's hard to find.

644 S Brooksvale Rd, Cheshire

$450,000

5 Beds ⋅ 2 Baths ⋅ 24190599 MLS

Five Bedroom Cape in desirable South Cheshire CT. Great established Neighborhood, walking distance to Farmington Canal Trail. Located in Norton School district. New school. This five bedroom home has a New boiler and water tank in 2020. Main level Bathroom has been recently remodeled. Laminate flooring over hardwood. Crown molding. Sold AS-IS.

110 Green Hill Ln, Cheshire

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