Chestnut Tree Hill Real Estate

Welcome to Chestnut Tree Hill, a hidden gem nestled in the charming town of Oxford, Connecticut, within New Haven County. This picturesque neighborhood is a harmonious blend of natural beauty and suburban convenience, making it an ideal place for families, professionals, and retirees alike.

Chestnut Tree Hill is characterized by its serene tree-lined streets, where you’ll find beautifully maintained homes that reflect a variety of architectural styles. The community is known for its friendly atmosphere, where neighbors become friends and gatherings are a regular occurrence. Residents enjoy the peace of suburban living while still being just a short drive away from bustling urban centers.

Nature enthusiasts will appreciate the abundance of outdoor recreational opportunities nearby. The area is dotted with parks, walking trails, and scenic spots perfect for picnicking or leisurely strolls. The nearby Housatonic River offers additional options for kayaking and fishing, ensuring that adventure is always just around the corner.

Families will find that Chestnut Tree Hill is served by excellent schools, making it a desirable location for those with children. The community is committed to providing a nurturing environment that encourages education and growth.

Convenience is key in Chestnut Tree Hill, with easy access to major highways, shopping centers, and dining options. Whether you’re looking for a cozy café or a vibrant restaurant scene, Oxford has it all.

In Chestnut Tree Hill, you’ll discover a welcoming community, beautiful surroundings, and a lifestyle that perfectly balances tranquility and accessibility. Come explore this enchanting neighborhood and see why so many have chosen to call it home!

Newest Listings in Chestnut Tree Hill

$565,000

3 Beds ⋅ 3 Baths ⋅ 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 ⋅ 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

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.