Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a picturesque neighborhood nestled in the heart of Killingworth, Connecticut, within the charming Middlesex County. This serene community is a hidden gem, offering a perfect blend of rural tranquility and modern convenience. With its lush landscapes, rolling hills, and vibrant flora, Chestnut Hill is ideal for those seeking a peaceful retreat from the hustle and bustle of city life.

The homes for sale in Chestnut Hill reflect the area's unique character, showcasing a variety of architectural styles that cater to diverse tastes. From cozy cottages to spacious family homes, each property is thoughtfully designed to harmonize with the natural surroundings. Many residences feature expansive yards, perfect for outdoor entertaining, gardening, or simply enjoying the serene views. Inside, you'll find open floor plans, modern amenities, and plenty of natural light, creating an inviting atmosphere for family and friends.

Beyond the beautiful homes, Chestnut Hill boasts a strong sense of community. Residents enjoy easy access to local parks, hiking trails, and recreational activities, making it an ideal location for outdoor enthusiasts. The nearby town center offers quaint shops, delightful eateries, and essential services, ensuring that everything you need is just a short drive away.

Whether you're looking to settle down or find a weekend getaway, Chestnut Hill presents an exceptional opportunity to embrace a lifestyle filled with comfort, charm, and natural beauty. Explore the homes for sale today and discover why this enchanting neighborhood is the perfect place to call home!

Newest Chestnut Hill Homes for Sale

$824,900

3 Beds ⋅ 3 Baths ⋅ 24207798 MLS

Tucked away on 4.5 beautiful acres in Killingworth, 79 Chestnut Hill Road offers exceptional privacy, peaceful pond views, and a welcoming sense of home from the moment you arrive. This distinctive 3-bedroom, 3-bath antique residence is filled with warmth and character, thoughtfully updated to provide the comfort and convenience of modern living. Extensive improvements completed between 2008 and 2026 include fresh interior paint, beautifully refinished natural hardwood floors, and a new elevated bluestone patio. Additional updates include the roof, windows, exterior paint, gutters, and water heater, along with updated electrical and plumbing, three-zone heating, central air, and a whole-house automatic generator. The kitchen and bathrooms have also been tastefully updated while preserving the home's timeless charm. Outside, mature trees, protected rear privacy, and an expansive, usable lawn create a serene backdrop with plenty of room to garden, entertain, explore, or simply enjoy the changing seasons. Whether spending a quiet morning at home, an afternoon outdoors, or an evening gathered with family and friends, this property offers a lifestyle that feels comfortable, private, and timeless. Offering generous land, historic character, substantial modern infrastructure, and convenient access to the shoreline and surrounding towns, 79 Chestnut Hill Road is a truly special property best experienced in person.

79 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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