Chestnut Hill Homes with Cape Cod Style

Welcome to Chestnut Hill, a hidden gem nestled in the heart of Killingworth, Connecticut, in Middlesex County. This charming neighborhood offers a serene escape from the hustle and bustle of city life, while still providing convenient access to local amenities and attractions. With its picturesque landscapes and friendly community atmosphere, Chestnut Hill is the perfect place to call home.

One of the standout features of this delightful area is its stunning Cape Cod-style homes. These residences exude timeless charm and character, showcasing steeply pitched roofs, symmetrical facades, and inviting front porches that beckon you to sit and enjoy the view. Inside, these homes often boast cozy fireplaces, hardwood floors, and spacious layouts, making them ideal for both families and those seeking a peaceful retreat.

Chestnut Hill is not just about beautiful homes; it’s also about the lifestyle. Residents enjoy a close-knit community with a strong sense of belonging. The neighborhood is surrounded by lush greenery and offers plenty of outdoor activities, from hiking trails to local parks, perfect for weekend adventures or leisurely strolls. Additionally, the area is known for its excellent schools and friendly neighbors, making it an ideal spot for families.

Whether you’re looking for a quaint Cape Cod home or a vibrant community to settle down in, Chestnut Hill in Killingworth is the perfect blend of comfort, charm, and convenience. Come explore this enchanting neighborhood and discover your dream home today!

Newest Chestnut Hill Homes with Cape Cod Style

$574,900

4 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24192282 MLS

Beautifully updated Cape Cod, ideally situated on two private acres near the Killingworth/Madison town line, offering the perfect blend of classic charm and modern updates. Recent improvements include vinyl siding, replacement windows and slider, a renovated kitchen, updated bathrooms, refinished hardwood floors, and a newly installed well neutralizing system. Recently painted throughout, the inviting main level features hardwood floors, a formal dining room, a spacious family room, and a bright breakfast area highlighted by a new pellet stove with a beautiful stone surround that can efficiently heat the entire home. The thoughtfully designed kitchen is complemented by a convenient pantry, while the laundry has been relocated to the second level for added convenience. Upstairs, you'll find four generously sized bedrooms, all on the same level. The spacious primary suite features hardwood flooring and a private bath, while the remaining bedrooms share an updated full bath. Step outside to your private backyard retreat, complete with a newer 20 x 20 Trex deck framed by a stunning stone wall, creating the perfect space for entertaining, dining, or simply relaxing in the peaceful wooded setting. Located just minutes from Madison's beaches, shopping, restaurants, and commuter routes, this move in ready home offers exceptional space, thoughtful updates, and comfortable everyday living.

245 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

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.