Chestnut Hill Homes for Sale

Welcome to the charming neighborhood of Chestnut Hill in CT! Known for its tree-lined streets, beautiful homes, and strong sense of community, Chestnut Hill is a highly sought-after area for homebuyers looking for a peaceful yet vibrant place to call home.

Chestnut Hill boasts a variety of homes for sale, ranging from cozy bungalows to spacious family estates, ensuring there is something for everyone in this picturesque neighborhood. With well-maintained properties and a mix of architectural styles, Chestnut Hill offers a unique blend of character and charm.

Residents of Chestnut Hill enjoy a convenient location with easy access to local amenities, including parks, schools, shopping centers, and dining options. The neighborhood's close-knit community spirit is evident in its regular events and gatherings, making it a welcoming place for families, young professionals, and retirees alike.

Whether you're looking to buy your first home, upgrade to a larger space, or downsize to a more manageable property, Chestnut Hill has something to offer. Don't miss the opportunity to explore the homes for sale in this lovely neighborhood and discover why Chestnut Hill is a place that many are proud to call home.

Newest Chestnut Hill Homes for Sale

$574,900

4 Beds ⋅ 3 Baths ⋅ 24192282 MLS

Beautifully updated Cape Cod, ideally situated on two private acres near the Killingworth/Madison town line, offering the perfect blend of classic charm and modern updates. Recent improvements include vinyl siding, replacement windows and slider, a renovated kitchen, updated bathrooms, refinished hardwood floors, and a newly installed well neutralizing system. Recently painted throughout, the inviting main level features hardwood floors, a formal dining room, a spacious family room, and a bright breakfast area highlighted by a new pellet stove with a beautiful stone surround that can efficiently heat the entire home. The thoughtfully designed kitchen is complemented by a convenient pantry, while the laundry has been relocated to the second level for added convenience. Upstairs, you'll find four generously sized bedrooms, all on the same level. The spacious primary suite features hardwood flooring and a private bath, while the remaining bedrooms share an updated full bath. Step outside to your private backyard retreat, complete with a newer 20 x 20 Trex deck framed by a stunning stone wall, creating the perfect space for entertaining, dining, or simply relaxing in the peaceful wooded setting. Located just minutes from Madison's beaches, shopping, restaurants, and commuter routes, this move in ready home offers exceptional space, thoughtful updates, and comfortable everyday living.

245 Chestnut Hill Rd, Killingworth

$340,000

4 Beds ⋅ 1 Baths ⋅ 24096243 MLS

** A Unique Opportunity at 30 Chestnut Hill Road, Killingworth** Step into a piece of history with this charming antique home, circa 1820-now available from a seasoned preservationist and architect with decades of experience restoring historic homes and barns. This property has already undergone critical structural repairs and has a watertight roof, setting the stage for the next phase of transformation. Exterior work-including masonry, roof detailing, windows, and finish-is underway. Current renovation plans envision a spacious 3-bedroom, 2.5-bath layout featuring a dedicated office, library, and over 3,000 square feet of living space. When completed, the home-along with a barn/garage addition and refreshed landscaping-is projected to be valued between $800,000 and $925,000. An optional larger barn built on the existing foundation at the rear of the property could add approximately $248,000 in additional value. The seller is now seeking a new steward for this exceptional property. There's also the option to retain the current owner as architect and contractor to help bring the vision to life. This is a rare chance to be part of a meaningful restoration-combining history, craftsmanship, and future potential.

30 Chestnut Hill Rd, Killingworth

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