Cheshire, CT Homes for Sale

Your Dream Home in the Heart of Cheshire! Welcome to this stunning 5-bedroom/potential 7 bedroom, 5.5-bath Colonial located in the center of Cheshire. With over 5,000 sq. ft. of living space and set on more than an acre, this masterpiece offers the perfect blend of luxury, comfort, and convenience. The seller has spared no detail in the design and upkeep of this exceptional home. Main Floor

Amy LaMaster The Bella Group, LLC

Welcome to the opportunity to build your dream home in a highly desirable location. Nestled on a secluded rear lot that is just under an acre, this thoughtfully designed 4-bedroom, 2.5-bath Colonial will offer 2,792 square feet of beautifully crafted living space with the perfect blend of privacy and modern comfort. Designed with today's lifestyle in mind, the open concept layout will seamlessly

Michael Dziedzic Precision Realty LLC

Welcome to this exceptional estate set deep off the road on 3.3 private, beautifully wooded acres in Cheshire, Connecticut. The main residence offers over 4,000 sq. ft. of living space, combining comfort, elegance, and versatility for today's lifestyle. Inside, you'll find five generous bedrooms, multiple living and entertaining areas, and a warm, inviting fireplace on the main level. The fully

Nancy Newman LPT Realty

Welcome to this stunning, practically brand-new 2,975 sq. ft. condo, built in 2024 and thoughtfully designed for modern living. Over $150,000 of upgrades! Immaculate and move-in ready, this open-concept home offers the perfect blend of style, comfort, and convenience in a fantastic location. The spacious first-floor primary suite features an elegant tray ceiling, a generous walk-in closet, and a

Stanley Martone Lamacchia Realty

Brand-new construction completed on 12/12/2025 and currently receiving final finishing touches by the owner. This beautiful home offers 4 spacious bedrooms, 3 full bathrooms, and a 2-car garage with an additional 506 square feet of garage space. The Town has issued the Certificate of Occupancy (CO). Thoughtfully designed layout with modern finishes throughout. A rare opportunity to own a newly

Carlos Ventura Ventura Group Realty LLC

HOUSE IS FRAMED AND READY FOR BUYER CHOICES! GREAT NEW CONSTRUCTION READY FOR QUICK DELIVERY FOR NEW OWNERS!! Amazing open layout on this modern colonial. This home is perfect for entertaining with a huge kit island open to a spacious Family Room. The floor plan is versatile with 4 bedrooms on the second floor and an optional 5th bedroom/office on the main level. Perfect for a work from home

Roy Evjen Evjen Agency

Welcome to Blackberry Woods, Cheshire's newest neighborhood! This private, secluded lot presents a rare opportunity to build your dream home with a respected local builder known for quality craftsmanship, meticulous attention to detail, and energy-efficient design. The Magnolia model showcases 9' ceilings, hardwood flooring in the main living areas, and a custom-designed kitchen that seamlessly

Abby Breau New England Prestige Realty

Privately set on nearly two acres in coveted South Cheshire, just moments from Roaring Brook Falls, this exceptional mountain-inspired estate offers a refined lifestyle defined by privacy, scale, and natural beauty. Thoughtfully renovated with meticulous attention to detail, the home features five bedrooms and three full bathrooms, including flexible living spaces ideal for extended arrangements.

Megan Northrop William Raveis Real Estate

Welcome to 106 Woodland Drive in highly sought-after Cheshire!! This stunning, fully renovated home has been beautifully reimagined from to top to bottom, offering modern style, comfort and functionality throughout. Featuring 3 bedrooms and 2 full bathrooms, this home is the definition of true move in ready living. Step inside to discover a showstopping, brand-new kitchen designed to impress,

Felipe Segura Coldwell Banker Realty

Inspiring country home. Inground pool, tennis court and equestrian features.

Joel Matson Coldwell Banker Realty

Welcome to the Copper Hill Association, a highly desirable and beautifully maintained neighborhood in Cheshire made up of just 32 single family ranch style homes. Conveniently located near shopping, restaurants and major roads, this friendly, peaceful community is known for its quiet streets, attractive homes, and welcoming atmosphere. Copper Hill offers a wonderful balance of comfort,

Michael Zerbini IMT Realty

Welcome to this charming ranch style single family home, thoughtfully updated and conveniently located just minutes from I84 and Route 8, with easy access to the Merritt Parkway and I91 for an easy commute. From the moment you walk in, you will appreciate the bright and refreshed feel throughout. The kitchen has been updated with quartz countertops, stainless steel appliances, and brand new

Eric Chou eXp Realty

Welcome to Old Towne Condos, a highly desirable center-of-town community offering convenience & walkability. This spacious 1,536 sq. ft., 2-bedroom, 2-1/2 bath Townhouse unit features a welcoming eat-in kitchen at the front of the home, a formal dining room, and a sunken living room complete with a wood-burning fireplace and French doors leading to a covered sun porch. The porch overlooks a very

The Sally Bowman Team Berkshire Hathaway NE Prop.

Welcome to this charming 4-bedroom, 2-bath home set on a picturesque 2-acre lot offering exceptional privacy and space to enjoy the outdoors. Tucked back from the road, this property features a large, sun-filled family room with a fireplace (for decorative purposes only), an inviting eat-in kitchen, and a convenient first-floor laundry area. The expansive yard is perfect for gardening, play, or

The Sally Bowman Team Berkshire Hathaway NE Prop.

Welcome to this stunning 2-year-young townhouse offering modern design and exceptional comfort. The open-concept main level is ideal for both everyday living and entertaining, featuring a beautiful kitchen with sleek quartz countertops, ample cabinetry, and a seamless flow into the living and dining areas. Rich hardwood flooring spans the entire first floor and continues through the upper-level

Tracey Fiasconaro Berkshire Hathaway NE Prop.

This beautiful one bedroom of Southwick at Cheshire is just what you've been looking for. Southwick at Cheshire is a 55+ community with beautiful grounds, a cozy communal library, billiard room, and many common spaces for social exchange. This single owner unit has been thoughtfully maintained for nearly 20 years. Upgrades include maple hardwood floors throughout kitchen and dining/living area,

Rebecca Bower Forever Homes Real Estate LLC

Highest and Best by Saturday 3/7/26 6pm Opportunity awaits at this historic property in the heart of Cheshire. Situated on Wallingford Road, this home offers a rare chance for investors, builders, or visionaries to restore or completely reimagine a piece of local history. The existing structure is in need of a full rebuild, presenting the perfect blank canvas to create a custom residence tailored

Christopher John Mentley New Haus Group LLC

Enjoy a peaceful country setting in this energy-efficient two-bedroom townhouse featuring a bonus finished lower level-ideal for a home office, family room, or guest space (not included in square footage). A separate laundry and utility area adds convenience. The eat-in kitchen offers newer stainless steel appliances, complemented by updated kitchen and baths throughout. An atrium door opens to a

Mark Gracia William Raveis Real Estate

Welcome to this beautifully upgraded townhouse condo located in a highly desirable complex. This spacious home offers 3 bedrooms and 2.5 baths with an open floor plan ideal for today's lifestyle. The main level features hardwood floors throughout, a bright living area and sliders to a private deck perfect for outdoor enjoyment. The kitchen is equipped with stainless steel appliances, granite

Sandra Deschenes Fercodini Properties, Inc.

Welcome to this expansive Colonial nestled on almost 2 secluded acres in one of Cheshire's sought-after neighborhoods. Presenting 4 bedrooms (potential for a 5th) each with its own walk-in closet, this home provides exceptional space and flexibility. Step into the grand foyer, highlighted by a beautiful chandelier and a newer window that fills the entry with natural light. The main level offers a

Stephanie Plaza Lamacchia Realty

Experience your dream home. This beautifully updated property boasts a large eat-in kitchen with sleek granite countertops, a practical island for dining, and a spacious area for entertaining. The elegant living room features a warm fireplace, perfect for cozy evenings. Three generously sized bedrooms are accompanied by two full bathrooms, with a third bathroom conveniently located on the first

Christopher Gueniat Northwest CT Realty