Chestnut Hill Real Estate

Welcome to Chestnut Hill, a picturesque neighborhood nestled in the heart of Connecticut, where charm meets convenience. Known for its serene atmosphere and stunning landscapes, Chestnut Hill offers residents a perfect blend of suburban tranquility and urban accessibility. This inviting community is characterized by its tree-lined streets, beautifully maintained homes, and a welcoming spirit that makes it an ideal place for families, young professionals, and retirees alike.

One of the standout features of Chestnut Hill is its strong sense of community. Residents often gather for seasonal events, farmers' markets, and neighborhood block parties, fostering connections that turn neighbors into friends. The local parks are perfect for leisurely strolls, picnics, or simply enjoying the natural beauty that surrounds you. With ample green spaces, families can enjoy outdoor activities, while children can play safely in the well-kept playgrounds.

For those who appreciate the arts and culture, Chestnut Hill is conveniently located near vibrant downtown areas that boast a variety of shops, restaurants, and entertainment options. Whether you're indulging in a gourmet meal or exploring local boutiques, there's always something new to discover.

Moreover, Chestnut Hill is served by excellent schools, making it a great choice for families seeking quality education for their children. With easy access to major highways and public transportation, commuting to nearby cities for work or leisure is a breeze.

If you’re looking for a community that embodies the perfect blend of comfort, charm, and convenience, Chestnut Hill is the place to call home. Discover the warmth and beauty of this delightful neighborhood today!

Newest Listings in Chestnut Hill

$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

Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.