Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a hidden gem nestled in the heart of Connecticut! This charming neighborhood is renowned for its picturesque landscapes, friendly community, and a perfect blend of suburban tranquility and urban convenience. With tree-lined streets and beautifully maintained homes, Chestnut Hill exudes a welcoming atmosphere that makes it an ideal place for families, young professionals, and retirees alike.

One of the standout features of Chestnut Hill is its rich array of outdoor spaces. Residents enjoy easy access to parks, walking trails, and recreational facilities, making it a haven for nature lovers and outdoor enthusiasts. Whether you’re taking a leisurely stroll, enjoying a picnic, or engaging in sports activities, the natural beauty of the area provides the perfect backdrop for an active lifestyle.

As for the homes for sale in Chestnut Hill, you’ll find a diverse selection that caters to various tastes and budgets. From charming single-family homes with classic architecture to modern townhouses with contemporary amenities, there’s something for everyone. Many properties boast spacious yards, ideal for entertaining or creating your own garden oasis. The neighborhood’s strong sense of community is reflected in the well-maintained homes and friendly neighbors, making it easy to settle in and feel at home.

With its excellent schools, proximity to shopping and dining, and a vibrant local culture, Chestnut Hill is not just a place to live; it’s a place to thrive. Explore the homes for sale today and discover why so many are choosing to call this delightful neighborhood their forever 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 with new wall of built-ins offering incredible storage and buffet area, 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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