Chestnut Hill Homes with Historic Antique Style

Welcome to Chestnut Hill, a hidden gem nestled in the picturesque town of Killingworth, Connecticut, located in the heart of Middlesex County. This charming neighborhood is renowned for its serene atmosphere and stunning natural beauty, offering residents a perfect blend of tranquility and community spirit.

Chestnut Hill is characterized by its historic antique-style homes, each telling a story of the past while providing modern comforts. These beautifully preserved residences showcase timeless architecture, with intricate details and rich craftsmanship that reflect the charm of yesteryears. Walking through the tree-lined streets, you’ll feel the warmth of a community that values its heritage, where neighbors greet each other and share a sense of belonging.

The neighborhood is surrounded by lush greenery and offers ample opportunities for outdoor activities, including hiking trails and parks that invite you to explore the beauty of nature. The tranquil atmosphere makes it a perfect retreat from the hustle and bustle of city life, while still being conveniently located near essential amenities and services.

In Chestnut Hill, you’ll find a variety of local shops, cozy cafes, and delightful eateries that contribute to the neighborhood’s vibrant community vibe. Families will appreciate the excellent school district, ensuring a quality education for children.

Whether you're drawn to the historic charm of the homes or the welcoming community, Chestnut Hill in Killingworth is a place where you can truly feel at home. Discover the magic of living in a neighborhood steeped in history, where every corner has a story to tell.

Newest Chestnut Hill Homes with Historic Antique Style

$824,900

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ ACTIVE Status ⋅ 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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