Chester, CT homes for sale & real estate

Chester, CT Homes for Sale

Introducing Highover-a 30-acre hilltop estate overlooking the lower Connecticut River, designed by renowned architect Alfred Hopkins. With over half a mile of frontage, this property offers one of the most private and naturally protected waterfront settings in Connecticut, along with direct access to Long Island Sound and the Atlantic Ocean. The estate has welcomed legendary visitors, including Albert Einstein, Katharine Hepburn, a former President, and William Gillette. The 5-bedroom, 8-bath chateau underwent a five-year renovation that preserved its timeless architecture while introducing modern comforts. A newly built 3-Bay garage and a spacious tobacco barn provide endless opportunities

Chester, CT Homes for Sale

Just Four Years Young - Cape-Style Beauty on Eight Private Acres! This one-floor living opportunity truly checks all the boxes! Privately sited on a rear eight-acre lot-level, landscaped, and professionally maintained-this gorgeous cape-style home offers both comfort and classic design. Features include a spacious and gracious first-floor primary suite, an inviting open floor plan, and quality construction with beautiful finishes throughout. A stunning floor-to-ceiling stone fireplace anchors the living room, while gleaming hardwood floors add warmth and charm. The gourmet kitchen and open dining area make entertaining easy. Additional highlights include propane warm air heat with central

Chester, CT Homes for Sale

One-floor living just steps from town and the Connecticut River. This well-maintained home features an open floor plan with a spacious family room highlighted by a cathedral ceiling. Offering 3 bedrooms on the main level, plus a finished lower level with two additional rooms-perfect for bedrooms, hobby space, or a home office. Outside, enjoy one garden sheds for storage and projects. * * * Seller is currently in process of hooking property up to city water and city sewer. * * *

Chester, CT Homes for Sale

Waterfront Colonial on a cul-de-sac near town and schools. Open floor plan Family room with fireplace. Eat-in kitchen with slider to the deck overlooking the Pratt Read Reservoir and private backyard. 4 Bedrooms. Primary Suite with full bath and walk-in closet. Hardwood floors. Central Air. Private path to the reservoir with your own recreation area.

Chester, CT Homes for Sale

This beautifully updated 4-bedroom, 2.5-bath home sits on more than 2 private acres and has been completely renovated from top to bottom. Every detail has been thoughtfully designed to combine modern comfort with timeless style. Inside, the brand-new kitchen features sleek cabinetry, quartz countertops, stainless steel appliances, and a subway tile backsplash - the perfect space for everyday living and entertaining. The spacious living areas include a sun-filled family room with skylights and walls of windows, a cozy living room with exposed beams and a brick fireplace, and a formal dining area. In this home you will find four bedrooms, including a serene primary suite with its own full ens

Chester, CT Homes for Sale

Charming Cape Cod home offering desirable first-floor living, nestled on a spacious and private lot in scenic Deep River. Surrounded by a farm-like atmosphere, this property features beautifully cleared land perfect for gardening, outdoor entertaining, or simply enjoying the peace and quiet of nature. Step inside to discover a bright, open-concept layout with thoughtful updates including a refreshed kitchen boasting maple cabinets and a large granite island. Flowing seamlessly into the living and dining areas. The main floor offers convenience and charm with 2 bedrooms, a full bath and laundry, while the unique second level boasts a true primary suite complete with a walk-in closet, sitting