Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a picturesque neighborhood nestled in the heart of Connecticut, where charm meets convenience. Known for its lush landscapes and friendly community vibe, Chestnut Hill is the perfect place to call home. With its tree-lined streets and beautifully maintained properties, this area offers a serene escape from the hustle and bustle of city life while still being just a stone's throw away from urban amenities.

The neighborhood is renowned for its excellent schools, making it an ideal choice for families looking to provide their children with a top-notch education. Additionally, Chestnut Hill boasts a variety of parks and recreational facilities, perfect for outdoor enthusiasts and families alike. Whether you enjoy hiking, picnicking, or simply taking a leisurely stroll, the natural beauty of this area will captivate you.

For those considering a move, Chestnut Hill offers a diverse range of homes for sale. From charming single-family residences to modern townhomes, there’s something here to suit every taste and budget. Many homes feature spacious yards, updated interiors, and proximity to local amenities, ensuring a comfortable and convenient lifestyle.

As you explore Chestnut Hill, you’ll discover a welcoming community that hosts various events throughout the year, fostering a strong sense of belonging among residents. With its blend of tranquility and accessibility, Chestnut Hill invites you to experience a lifestyle that truly feels like home. Don’t miss your chance to be part of this delightful neighborhood—your dream home awaits!

Newest Chestnut Hill Homes for Sale

$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 Homes for Sale

Newest Chestnut Hill Homes for Sale

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