Chestnut Tree Hill Homes for Sale

Chestnut Tree Hill Homes for Sale

Welcome to Chestnut Tree Hill, a hidden gem nestled in the heart of Oxford, Connecticut! This picturesque neighborhood, located in New Haven County, offers a perfect blend of serene suburban living and vibrant community spirit. With its tree-lined streets, charming homes, and welcoming atmosphere, Chestnut Tree Hill is an ideal place for families, professionals, and retirees alike.

The area is known for its stunning natural beauty, with ample green spaces and parks that invite outdoor activities year-round. Residents can enjoy leisurely strolls, picnics, and recreational sports in the nearby parks, making it easy to embrace an active lifestyle. The neighborhood also boasts a strong sense of community, with local events and gatherings that foster connections among neighbors.

Chestnut Tree Hill features a diverse array of homes for sale, catering to various tastes and budgets. From cozy single-family residences to spacious modern designs, there’s something for everyone in this charming enclave. Many homes showcase beautiful architectural details, manicured lawns, and inviting outdoor spaces, perfect for entertaining or unwinding after a long day.

Conveniently located, Chestnut Tree Hill offers easy access to major highways, making commuting to nearby cities a breeze. Residents also benefit from excellent schools, shopping centers, and dining options, ensuring that all your needs are just a stone's throw away.

If you're searching for a place that combines tranquility with a vibrant community, look no further than Chestnut Tree Hill. Explore the available homes for sale today and discover the perfect fit for your lifestyle in this enchanting neighborhood!

Newest Chestnut Tree Hill Homes for Sale

$565,000
3 Beds 3 Baths 24196298 MLS
Set on 1.52 beautiful level acres, this oversized raised ranch offers exceptional space, flexibility & endless possibilities. Featuring 3-4 bedrooms & 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 & charm are 2 fireplaces - 1 gas & 1 wood-burning - creating cozy spaces to enjoy. 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 & 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! Home is FOR SALE ONLY - there is a tik tok scam that it is also for rent - its NOT!

124 Chestnut Tree Hill Road Ext, Oxford

$919,000
4 Beds 4 Baths 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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