Cheshire Real Estate

Welcome to Cheshire, Connecticut – a picturesque town nestled in the heart of New Haven County. Known for its charming neighborhoods, rich history, and vibrant community spirit, Cheshire offers a unique blend of suburban tranquility and easy access to urban amenities.

With a population of just over 29,000 residents, Cheshire prides itself on its strong sense of community and family-friendly atmosphere. The town is renowned for its excellent school system, making it an ideal place for families seeking a nurturing environment for their children. The local parks, such as the expansive Cheshire Park and the scenic Bartlem Park, provide ample opportunities for outdoor activities, from hiking and biking to picnicking and playing sports.

Cheshire’s historical roots run deep, with many well-preserved buildings and landmarks that tell the story of its past. Strolling through the town center, you’ll find a delightful mix of quaint shops, cafes, and restaurants, each offering a taste of local flavor. The annual Cheshire Fall Festival and other community events foster a sense of belonging, bringing residents together to celebrate their town’s unique character.

Conveniently located near major highways, Cheshire offers easy access to nearby cities like New Haven and Hartford, making it a perfect choice for commuters. Whether you’re drawn to its scenic landscapes, vibrant community life, or top-notch schools, Cheshire is a hidden gem waiting to be explored. Discover the charm of Cheshire – where small-town warmth meets modern convenience!

Newest Listings in Cheshire

$612,000

2 Beds ⋅ 2 Baths ⋅ 24219785 MLS ⋅ Cheshire Crossing BLDG.

This MUST-SEE beautiful ranch-style home is in one of Cheshire's finest 55+ adult communities. This beautifully designed single-level unit perfectly blends convenience, luxury, and expansive space. Featuring 2 spacious bedrooms and 2 full bathrooms, the open-concept layout flows effortlessly into a stunning, sun-drenched sunroom-the perfect spot for your morning coffee or curling up with a good book. The heart of the home seamlessly connects the living and dining areas, creating an inviting environment for everyday life, relaxation, and effortless entertaining. An office entered through beautiful glass french doors makes getting things done easy. The vaulted ceiling, quality moldings and architectural features enhance this unit's appeal. Abundant storage is available in the spacious, convenient 2-car attached garage and an enormous full basement. The basement offers endless potential for a workshop, home gym, or seasonal storage. Enjoy the peace of mind that comes with a maintenance-free lifestyle in a vibrant, quiet community close to Cheshire's charming town center, walking trails, and dining. Don't miss out. Come and see it.

25 Bramble Way, Cheshire

$429,900

2 Beds ⋅ 2 Baths ⋅ 24220055 MLS

Move right into this beautifully maintained 2-bedroom, 2-bath ranch in a desirable established neighborhood! The bright, spacious living room features hardwood floors and a cozy gas fireplace. The updated kitchen boasts granite countertops, tile flooring and stainless appliances, flowing seamlessly into the family room with a full bath and convenient laundry area. The dining room, accented by hardwood floors, connect to both the kitchen and family room, creating an ideal space for entertaining. Both bedrooms have hardwood floors and ceiling fans. Additional highlights include central air, upgraded electrical service, a newer roof, newer windows, natural gas, city water and sewer, and an updated hall bath. Detached one car garage. Situated on a beautiful level lot, this move-in-ready home is one you won't want to miss!

105 Deepwood Dr, Cheshire

$699,925

3 Beds ⋅ 3 Baths ⋅ 24219186 MLS ⋅ The Reserve At Stonebridge Crossing BLDG.

Experience luxury living in this beautifully appointed 2025-built residence offering approximately 2,450 square feet of thoughtfully designed living space, featuring 3 bedrooms and 2.5 bathrooms. Built with EG Home's renowned energy-efficient construction, this exceptional home combines modern sophistication, quality craftsmanship, and everyday comfort. The chef-inspired kitchen features a sleek induction cooktop, elegant finishes, and an inviting layout perfect for entertaining. The desirable main-level primary suite offers a spacious private retreat with a luxurious bathroom, walk-in closet, and additional closet space. Convenient main-level laundry adds ease to everyday living. Upstairs, discover additional bedrooms and versatile spaces ideal for a home office or flexible living arrangements. An expansive unfinished basement offers endless possibilities for future customization, while the attached two-car garage provides added convenience. One of this home's most captivating features is its picturesque wooded backdrop, offering beautiful seasonal views and a peaceful setting where deer and wild turkeys have been spotted. Enjoy a quiet neighborhood where neighbors spend time outdoors and gather at the community pavilion. The Farmington Canal Heritage Trail is within walking distance and offers a dedicated path for walking, biking, and running away from road traffic. Schedule your private showing and experience it for yourself!

74 Shea Cir, Cheshire

$524,900

3 Beds ⋅ 3 Baths ⋅ 24216659 MLS

More than 30 years of care, a brand-new roof, and a backyard ready for your next gathering-this classic Cheshire Colonial is ready to welcome you home. Lovingly maintained by its original owners, this 3 bedroom, 2-1/2 bath home sits on 0.46 acres and offers 1,632 square feet plus a partially finished lower level. Hardwood floors bring warmth and character, while a comfortable layout offers space to come together and spread out. Formal living and dining rooms set the scene for holidays and special occasions, the eat-in kitchen welcomes everyday meals, and the family room with a fireplace is an inviting place to settle in at the end of the day. A convenient half bath completes the main level. Upstairs, the primary bedroom features its own full bath, with two additional bedrooms and a second full bath rounding out the floor. The partially finished lower level offers flexible space for movie nights, a home office, workouts, or hobbies, along with generous storage. Take your morning coffee out to the deck, gather friends for a summer dinner, or spend an afternoon tending the garden. Overlooking the backyard, the deck extends your living space outdoors. An attached two-car garage, low-maintenance vinyl siding, public water, septic, and oil-fired hot-water heat add everyday practicality. A new roof in 2026 and a boiler replaced in 2017 are valuable updates.

1430 S Main St, Cheshire

$355,000

2 Beds ⋅ 2 Baths ⋅ 24218209 MLS ⋅ Old Towne BLDG.

Welcome to 7 Old Towne Road! This 2 bedroom, 2 bath, move-in ready RANCH unit is located in the highly sought after Old Towne Condos. It is an end, corner unit that sits adjacent to a wooded area with views of nature all around. There is ample parking directly in front of the unit along with its one car attached garage. This home has been completely remodeled. The main level features two large bedrooms, the primary with a bathtub and separate area with a sink. The stacked washer & dryer are conveniently located right outside both bedrooms and main bathroom. The open living and dinning room features plenty of space for entertaining. The living room also features a fireplace, vaulted ceilings and a slider that leads outside to a cozy, private back patio. All mechanicals were replaced at time of remodel in 2022, are high efficiency models and have programable thermostats. In addition to this unit's highlights, the private community features a pool. The complex is next to a local favorite coffee house and is close to route 10 giving you access to the center of Cheshire. This well established complex is near all amenities. This is a must see! Agent/Owner Related HIGHEST & BEST BY 1PM 11/5/26

7 Old Towne Rd Unit 7, Cheshire

$949,900

4 Beds ⋅ 4 Baths ⋅ 24215562 MLS

Room to gather, privacy to unwind, and 2.58 acres to call your own-welcome to 704 Andrea Court. Set in one of Cheshire's most sought-after cul-de-sac neighborhoods, this classic Colonial has been cherished by its original owners for 30 years. With 3,145 square feet, four bedrooms, four full baths, and additional 700 sq ft in the finished walk out lower-level space, there's room for everyday living, memorable celebrations, and whatever your next chapter brings. Formal living and dining rooms offer inviting spaces to entertain, while the heart of the home is the eat-in kitchen opening to a family room with a fireplace, french door to 2 tier deck. From morning coffee to holiday gatherings, this connected layout keeps everyone together. Office, full bath and laundry room completes the main level. Upstairs, the primary suite offers a private full bath and walk-in closet, with three additional bedrooms and another full bath providing comfortable accommodations and flexibility. The finished walk out lower level expands the possibilities with space for a recreation room, home gym, sauna, and fourth full bath. An attached two-car garage, central air, oil-fired forced-air heat, private well, and septic round out the property. Enjoy convenient access to Routes 68 and 15 and the best of Cheshire-from the Farmington Canal Heritage Trail and Roaring Brook Falls to town parks, open space, and shopping and dining, including Whole Foods, Starbucks, and Barnes & Noble. Come see your new home!

704 Andrea Ct, Cheshire

$239,800

2 Beds ⋅ 2 Baths ⋅ 24215579 MLS ⋅ Cheshire Hillside Village BLDG.

This beautiful spacious 1,200 square foot home is one of the largest in Hillside Village and features two bedrooms, one and a half baths, and an office, nestled in the woods, yet across the street from Maplecroft Plaza. The main bathroom, the sliding door in the dining room to the deck, and the picture window in the family room were all upgraded in 2024. The primary bedroom is spacious, has a half bath and two closets including a walk-in. The floor plan offers endless possibilities, and the condo fee includes heat, hot water, and water. Parking is close by and you can cross over the nearby bridge and jog or walk on the track at Cheshire Academy, as this well- designed community. It's easily accessible to I-84, I-91, I-691, and the Merritt Parkway, so visiting the grandchildren is easy. All occupants must be at least age 62.

353 E Mitchell Ave Unit 353, Cheshire

$525,000

3 Beds ⋅ 2 Baths ⋅ 24216017 MLS

Welcome to this delightful South End Colonial offering plenty of space, comfort, and versatility! This well-maintained home boasts a modern kitchen with granite countertops and newer stainless-steel appliances. The beautiful dining room is accented by custom paneled wainscoting, while the spacious front-to-back living room offers hardwood floors and plenty of room to gather and entertain. A bonus room on the main level provides flexible space for a home office, gym, or playroom. Upstairs, the primary bedroom offers three closets and a charming built-in window seat, along with two additional bedrooms and a full bath. The finished lower level adds approximately 360 square feet of living space, perfect for a family room, recreation area, or home gym, with additional unfinished space for storage and a workshop. The propane heating system and central air conditioning condenser were replaced in 2018. Outside, enjoy a level yard, deck, patio, and storage shed, along with the convenience of a one-car garage. With its inviting living spaces, thoughtful details, and convenient location, this home has so much to offer!

4 Cherrywood Cir, Cheshire

$850,000

4 Beds ⋅ 4 Baths ⋅ 24216993 MLS

It's here! 6 Mt Sanford is move-in ready showcasing all the newest designs for carefree living. Don't miss this brand new farmhouse style contemporary Colonial in south Cheshire. A picturesque country setting close to shopping & easy highway access.This stunning home blends modern elegance with exceptional craftsmanship throughout. Soaring 9-ft ceilings, 1.5" thick engineered HW floors throughout & a gas fireplace w/slate surround & wood mantle invites you into this bright open floor design. The gourmet kitchen features quartz countertops, subway tile backsplash, massive center island, stainless steel appliances, a custom chimney-style vented hood,& walk-in pantry. A perfect space for everyday living & entertaining. Step outside onto a private 20x16 back patio off the kitchen or to the welcoming front of the home which has a lovely lighted covered farmer's porch ideal for relaxing. A private office and separate mudroom complete the main floor. Upstairs a luxurious primary suite is joined by two additional bedrooms, which share a Jack-n-Jill bathroom, plus a private en-suite guest bedroom & bath. A second floor laundry adds extra convenience. Potential additional space in basement, that could be easily finished.Private backyard, protected from any future development.

6 Mount Sanford Rd, Cheshire

$595,000

4 Beds ⋅ 2 Baths ⋅ 24217571 MLS

A TRUE SHOWSTOPPER IN CHESHIRE! Welcome to 327 West Main Street, where timeless New England charm meets modern updates! This beautifully refreshed 4-bedroom, 2-full-bath home offers the character and craftsmanship you love in an older home, with the updates and conveniences today's buyers are looking for. From the moment you arrive, you'll appreciate the attention to detail throughout. Recent improvements include new windows, gutters, fresh interior paint, an on-demand hot water system, and a new mini-split system for year-round comfort and efficiency. Step outside and get ready to enjoy your own backyard retreat, complete with a brand-new above-ground pool and deck, perfect for summer entertaining! You'll also love the covered front and rear porches, ideal for enjoying your morning coffee or unwinding at the end of the day. And just when you think you've seen it all, there's MORE! The detached 3-car garage is an incredible bonus, featuring an epoxy floor and finished loft space above. Whether you're looking for a home office, fitness space, art studio, workshop, or simply extra room for your hobbies, the possibilities are endless! Homes offering this much character, versatility, and modern convenience don't come along every day. Move right in and start enjoying everything this unique Cheshire property has to offer!

327 W Main St, Cheshire

$350,000

2 Beds ⋅ 2 Baths ⋅ 24216609 MLS ⋅ Southwick At Cheshire BLDG.

Southwick at Cheshire is offering unit 12 in this sought after 55+ community. This cottage style condo offers 2 bed, 2 bath and in unit washer and dryer. The living space is the ideal open layout to downsize to without feeling like you've compromised lifestyle. Vaulted ceilings, architectural columns and a beautiful staircase leading to a large upper level loft add an extra special touch to this floorplan. This unit comes with a 1 car detached garage. We welcome you in to see for yourself what your next chapter can look like in this centrally located town of Cheshire where restaurants, shopping and highway access will ultimately check all the boxes on your wish list.

12 Southwick Court Unit 12, Cheshire

$889,000

5 Beds ⋅ 5 Baths ⋅ 24212574 MLS

Gracefully positioned within one of Cheshire's premier neighborhoods, this impressive 4,734 sf beauty features 5 beds, 5 baths, showcases classic architectural elegance, exceptional curb appeal and a picturesque, professionally landscaped grounds, designed for year-round enjoyment. A two-story foyer highlighted by an arched transom casts an abundance of natural light & introduces lovely architectural details and distinctive, colorful finishes throughout. Expansive kitchen with abundant cabinetry, generous counter space, breakfast bar, pantry, & sunny breakfast nook, along with a sunlit living room with fireplace, both offering convenient access to the rear deck for entertaining. The main level is further complemented by a formal dining room, convenient laundry room, 1/2 bath, & two private offices with custom built-ins & French doors, offering outstanding flexibility for remote work, guest room, study space, or additional living areas. Elegant open staircase to second level offers an exceptional primary suite featuring a spa-inspired full bath with a jetted tub, double vanity, stall shower & walk-in closet. Three generously sized secondary bedrooms & two well-appointed full baths, including a Jack-&-Jill bath, complete the upper level. Finished lower level with walk-out offers a full bath, abundance of storage & an adaptable floorplan with plenty of room to expand. Fabulous location to the new Stonebridge shops, parks, local farms, etc., A true must see to appreciate!

100 Scenic Ct, Cheshire

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Cheshire Real Estate

Newest Listings in Cheshire

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