Cheshire, CT Homes for Sale with Acreage

This custom-built, one-owner home is nestled at the end of a quiet cul-de-sac in sought after Cheshire, Connecticut. Set on 2.2 acres of park like grounds, the home offers unmatched privacy and serene surroundings. Thoughtfully designed with meticulous craftsmanship, this home features three bedrooms, including a primary suite with a private exercise room with jacuzzi. The home also offers a two

Lori Valimont Berkshire Hathaway NE Prop.

Welcome to this exceptional 4-bedroom, 3.5-bath Colonial nestled on over 3 private acres at the end of a cul-de-sac in one of Cheshire's desirable neighborhoods. Set back from the road with a long private driveway, this home offers the perfect balance of privacy and convenience. Designed for both everyday living and entertaining, the flexible floor plan features spacious living areas, a private

Stephanie Plaza Lamacchia Realty

First-Floor Living at Its Finest! Bright and beautifully designed contemporary home offering over 3,400 square feet of versatile living space in a highly desirable neighborhood. Step into the dramatic foyer and be welcomed by a stunning open staircase that sets the tone for this exceptional home. The spacious eat-in kitchen features granite countertops, built-ins, desk area, newer wine cooler,

Stacey Deangelis Calcagni Real Estate

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, &

Jennifer Bundock Coldwell Banker Realty

Charm abounds in this custom built reproduction Saltbox completely remodeled down to the studs featuring 5 bedrooms and 3 1/2 tiled baths. Home is in a picturesque setting with spring fed pond on almost 2 acres. Sparkling hardwood floors througout the home. Gracious large living room features hardwood floors, fireplace and wood storage box. Brand new kithen remodeled down to the studs, featuring

Roberta Havlick William Raveis Real Estate

Come see this rare 2 family find in the heart of Cheshire. Both units have been fully updated with new kitchens, granite countertops, stainless steel appliances, updated baths, plumbing, electrical, and HVAC. Schedule your showing today

Michael Dziedzic Precision Realty LLC

Welcome to this beautifully maintained 5 bedroom, 3.5-bath Colonial, perfectly situated on 1.25 picturesque acres with its own private pond, creating a peaceful and private retreat right in your backyard. Designed with both comfort and entertaining in mind, this spacious home features an open-concept floor plan, soaring 9-foot ceilings, and gleaming hardwood floors throughout. The heart of the

Shari DiDomenico Berkshire Hathaway NE Prop.

Timeless Center Hall French Colonial featuring 5 Bedrooms and 3.5 Baths, gracefully set within a quiet neighborhood. This charming residence showcases exceptional curb appeal, highlighted by beautifully crafted stone walls and professionally designed landscaping that draw the eye to its stately brick facade and custom, functional shutters. Just beyond the inviting entryway, you'll find a

Phil Giampietro Coldwell Banker Realty

Welcome to 25 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 six bedrooms - 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

George Santos William Raveis Real Estate

Welcome to 1050 Jarvis St! This Colonial was completed in Dec 2025, and is set on a private 1.9-acre lot. This home offers 4 bedrooms, 3 full baths, a dedicated office, and energy-efficient systems throughout. The kitchen features quartz countertops, a walk-in pantry, stainless appliances and opens to the dining room, perfect for gatherings. The main level also features living room, dedicated

Jennifer Bundock Coldwell Banker Realty

NEW ROOF GOING ON JULY15TH AND 16TH. NEW RADON MITIGATION SYSTEM INSTALLED. This gorgeous home on Cook Hill Road sits set back from the road on a 2+ acer level lot. This open floor plan home is sure to please. Large kitchen featuring double ovens, cook top, plenty of counter space and multiple pantry's is a cook's dream. The kitchen is open to an ample casual dining area that overlooks the

Betsy Stellato LAER Realty Partners

Welcome home to this beautifully updated ranch in a highly desirable neighborhood, just minutes from shopping, restaurants, and everyday conveniences. This move-in ready home features hardwood floors throughout and a spacious living room with a classic brick fireplace and Vermont Castings wood-burning insert, creating a warm and inviting gathering space. The dining room flows seamlessly into the

Stacey Deangelis Calcagni Real Estate

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.

Karen Brimberg William Raveis Real Estate

Charming ranch on a park-like 1.2-acre lot with blooming perennials near the Cheshire line! Detached 2-car garage. LR/DR combo w/ built-in shelving. 2 BR, 1 bath, PLUS a massive family room addition - vaulted ceiling, gas FP, window seat - easily repurposed as primary bedroom. Updates incl: NEW CAIR, waterproofing w/ warranty, roof '15/gutters '23, well pump '24, whole-home generator '19,

Allison Hughes William Raveis Real Estate