Chestnut Tree Hill Homes for Sale

Chestnut Tree Hill Homes for Sale

Welcome to Chestnut Tree Hill, a hidden gem nestled in the picturesque town of Oxford, Connecticut. This charming neighborhood, located in New Haven County, offers a delightful blend of suburban tranquility and vibrant community spirit. As you wander through the tree-lined streets, you'll find beautifully maintained homes that reflect a variety of architectural styles, catering to diverse tastes and lifestyles.

Chestnut Tree Hill is known for its spacious lots and scenic views, making it an ideal setting for families and individuals seeking a serene escape from the hustle and bustle of city life. The area boasts excellent schools, parks, and recreational facilities, ensuring that residents have access to everything they need to thrive. With its close-knit community atmosphere, neighbors often come together for local events, fostering friendships and a sense of belonging.

For those interested in making Chestnut Tree Hill their home, a selection of homes for sale awaits. From charming single-family residences to modern new builds, there is something for everyone in this inviting neighborhood. Each property reflects the care and pride of ownership, offering ample space for both relaxation and entertaining.

Explore Chestnut Tree Hill, where the beauty of nature meets the warmth of community. Whether you're a first-time homebuyer or looking to settle down in a peaceful environment, this neighborhood is sure to capture your heart. Don't miss the opportunity to find your dream home in this enchanting part of Oxford, CT!

Newest Chestnut Tree Hill Homes for Sale

$565,000
3 Beds 3 Baths ACTIVE Status 24196298 MLS
Set on 1.52 beautiful level acres, this oversized raised ranch offers exceptional space, flexibility and endless possibilities. Featuring 3-4 bedrooms and 3 full baths, this versatile floor plan allows you to customize the living space to fit your lifestyle, whether you need a home office, guest suite, playroom, multi- generational living, or additional bedroom. The layout also offers excellent potential for an in-law setup with its flexible room arrangement. A huge family room over the garage provides the perfect gathering space for entertaining or relaxing. This was previously used as a extra large bedroom! Adding to the homes warmth and charm are two fireplaces - one gas and one wood-burning - creating cozy spaces to enjoy or relax in the inviting three-season porch or out on the deck. The finished lower level includes an additional room ideal for a playroom, fitness room or office. With generous living spaces inside and a beautiful level lot outside, this home is ready to accommodate a variety of needs and lifestyles for years to come. Major updates provide peace of mind, including a whole house generator, an 11 year old roof and a driveway that was paved in 2017. There is a 2 car attached garage and an additional detached 3rd garage. The original 2 car garage is now a huge work room ready for whatever projects you can dream up! Come make this beautiful home your own by adding all of your personal touches to make it yours!

124 Chestnut Tree Hill Road Ext, Oxford

$919,000
4 Beds 4 Baths ACTIVE Status 24187521 MLS
Welcome to your own private sanctuary. Nestled on a stunning lot with a large private pond, launch a canoe, kayak or pedal board directly from your backyard and spend your days gliding across the calm glistening waters. Enjoy morning coffee your covered deck while taking in breathtaking views of your own private pond sanctuary. Inside, brand new hardwood floors grace the second floor, basement, and a stunning custom chevron patterned Great Room. The first floor floors are fully refinished. The kitchen features custom cherrywood cabinetry, wet bar, a new quartz island countertop, fresh cabinet hardware, and custom Roman shades carried through to the dining area. Custom wood trim, molding, and tray ceilings elevate the primary bedroom and dining room, while a custom frame surround the brand new Heat and Glow gas fireplace beneath a striking new chandelier in the Great Room. Surround sound runs throughout the main level, perfect for entertaining. A natural gas whole house generator adds peace of mind year round. A first floor bedroom is perfect as a home office or in law setup. The large detached garage upper level offers incredible potential to be finished as an in law suite or private apartment. Additional updates include new GE Profile washer and dryer, ADT security system with Nest cameras, new exterior lighting, radon remediation system and newly painted interior. This is not just a home. It is a lifestyle. Private. Peaceful. Perfected.

37 Jenny Ln Unit 2, Oxford

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