Chestnut Hill Homes for Sale

Chestnut Hill Homes for Sale

Welcome to Chestnut Hill, a hidden gem nestled in the charming town of Killingworth, Connecticut. This picturesque neighborhood is part of Middlesex County, where the tranquility of suburban life meets the beauty of nature. Chestnut Hill is characterized by its lush landscapes, friendly community vibe, and an abundance of outdoor activities, making it an ideal place for families, retirees, and everyone in between.

As you stroll through the tree-lined streets, you’ll be captivated by the stunning architecture of the homes, which range from quaint cottages to spacious contemporary designs. Many properties boast expansive yards, perfect for gardening, entertaining, or simply enjoying the serene surroundings. The community is known for its strong sense of camaraderie, with neighbors often coming together for local events, seasonal festivities, and outdoor gatherings.

For those who enjoy an active lifestyle, Chestnut Hill offers easy access to numerous parks, hiking trails, and recreational facilities. The nearby Killingworth town center features quaint shops, delightful eateries, and essential services, ensuring that residents have everything they need just a short drive away.

Currently, there are beautiful homes for sale in Chestnut Hill, each offering unique features and the potential for personalization. Whether you're looking for your first home or a place to settle down, this neighborhood provides a welcoming atmosphere and the perfect backdrop for creating lasting memories. Explore the enchanting world of Chestnut Hill and discover your dream home today!

Newest Chestnut Hill Homes for Sale

245 Chestnut Hill Rd, Killingworth
$549,900
4 Beds ⋅ 3 Baths ⋅ 24219383 MLS
Beautifully updated Cape Cod set on two private acres near the Killingworth/Madison town line. This well-maintained home offers four bedrooms, updated living spaces, and numerous recent improvements, including vinyl siding, replacement windows and slider, a renovated kitchen, updated bathrooms, refinished hardwood floors, and a new well neutralizing system. The main level features hardwood floors, a spacious family room, formal dining room with a wall of built-ins offering plenty of storage and buffet space, and a bright breakfast area with a pellet stove featuring an attractive stone surround that can efficiently heat the entire home. The updated kitchen includes a pantry, granite counters, breakfast bar, and the laundry has been relocated to the second floor for convenience. All four generously sized bedrooms are located upstairs, including the primary bedroom with hardwood floors and a private full bath. The other bedrooms share an updated full bath. Outside, a 20 x 20 Trex deck bordered by a beautiful stone wall overlooks the private, wooded backyard, providing plenty of space for outdoor dining and entertaining. The driveway has also been recently repaved. Enjoy the privacy of this two-acre setting while being just minutes from Madison's beaches, shopping, restaurants, and commuter routes. With so many recent updates already completed, this home is ready for its next owners.

245 Chestnut Hill Rd, Killingworth
173 Chestnut Hill Rd, Killingworth
$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
79 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
30 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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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.

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