Chestnut Hill Real Estate

Welcome to Chestnut Hill, a charming neighborhood nestled in the heart of Connecticut. Known for its picturesque landscapes and warm community spirit, Chestnut Hill offers a perfect blend of suburban tranquility and urban convenience.

As you stroll through the tree-lined streets, you’ll be greeted by beautifully maintained homes, each with its own unique character. The neighborhood boasts a variety of architectural styles, from classic colonials to modern designs, ensuring that there’s something for everyone. Chestnut Hill is not just a place to live; it’s a community where neighbors become friends, and every corner holds a story.

Families will appreciate the top-rated schools in the area, providing a nurturing environment for children of all ages. Parks and recreational facilities are abundant, offering plenty of opportunities for outdoor activities, whether it’s a leisurely walk, a picnic, or a weekend soccer game. The local community center hosts events throughout the year, fostering a sense of camaraderie among residents.

For those who enjoy shopping and dining, Chestnut Hill is conveniently located near a variety of local boutiques, cafes, and restaurants that cater to all tastes. Whether you’re in the mood for a cozy coffee shop or an upscale dining experience, you’ll find it just a stone’s throw away.

With its ideal location, friendly atmosphere, and rich community life, Chestnut Hill is not just a neighborhood; it’s a place you’ll be proud to call home. Come explore the charm and beauty of Chestnut Hill, where your dream home awaits!

Newest Listings in Chestnut Hill

$500,000

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 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 ⋅ 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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Chestnut Hill Real Estate

Newest Listings in Chestnut Hill

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