Chestnut Hill Real Estate

Welcome to Chestnut Hill, a picturesque neighborhood nestled in the heart of Connecticut that seamlessly blends suburban tranquility with vibrant community spirit. Known for its lush landscapes and charming architecture, Chestnut Hill offers a serene escape while still being conveniently located near urban amenities.

As you stroll through the tree-lined streets, you’ll be captivated by the stunning homes that reflect a variety of architectural styles, from classic colonials to modern designs. Many properties boast spacious yards, providing the perfect backdrop for family gatherings and outdoor activities. The community is characterized by its friendly atmosphere, where neighbors know each other by name, fostering a sense of belonging that is hard to find elsewhere.

Nature enthusiasts will appreciate the nearby parks and recreational areas, which offer ample opportunities for hiking, biking, and picnicking. The local parks are not just places for leisure but also serve as community hubs where events and gatherings bring residents together throughout the year.

Chestnut Hill is also conveniently located near top-rated schools, making it an ideal choice for families looking to provide their children with an excellent education. With a variety of shopping, dining, and entertainment options just a short drive away, residents enjoy the best of both worlds—a peaceful neighborhood with easy access to the excitement of city life.

Whether you’re looking to settle down or invest in a vibrant community, Chestnut Hill is a hidden gem that promises a fulfilling lifestyle in the beautiful state of Connecticut. Come explore what makes this neighborhood so special and discover the perfect place to call home!

Newest Listings in Chestnut Hill

$500,000

3 Beds ⋅ 3 Baths ⋅ 24208096 MLS

A charming and comfortable ranch set along Chestnut Hill, one of Killingworth's most picturesque roads. This inviting home offers a wonderful blend of warmth, privacy, and natural beauty. The open living and dining area features a handsome stone fireplace and hearth, while a wall of glass fills the space with natural light. French doors lead to a sunroom that extends the living area and captures views of the surrounding property. A gas fireplace adds year-round comfort and ambiance. The kitchen features granite countertops and a breakfast bar. Three bedrooms and two baths are located on the main level. Handsome hardwood floors throughout. A spacious 36' x 12' deck provides ample room for grilling, relaxing, and entertaining. Enjoy a sense of peace and privacy while taking in views of the yard and surrounding woods. The expansive lower level offers excellent flexibility, with space for a rec room, studio, home office, or family room. A half bath and convenient access to the attached two-car garage add to its versatility. Set on 3.8 acres, the property offers plenty of room to enjoy the outdoors. A generous fenced-in area is ideal for play, gardening, and pets. Located in southern Killingworth, the home offers convenient access to the shoreline, downtown Madison, shopping, and restaurants. Boston and New York are within a few hours' drive, and commuting routes are easily accessible.

173 Chestnut Hill Rd, Killingworth

$749,900

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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Chestnut Hill Real Estate

Newest Listings in Chestnut Hill

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