Chestnut Oaks Homes for Sale

Welcome to Chestnut Oaks, a hidden gem nestled in the charming city of Matthews, North Carolina. This delightful neighborhood offers a perfect blend of suburban tranquility and urban convenience, making it an ideal place for families, professionals, and retirees alike. With its picturesque tree-lined streets and beautifully manicured lawns, Chestnut Oaks exudes a warm, welcoming atmosphere that invites you to call it home.

The community is known for its friendly neighbors and a strong sense of camaraderie, creating a tight-knit environment where everyone feels connected. Residents enjoy easy access to a variety of amenities, including shopping centers, parks, and top-rated schools, all just a stone's throw away. The nearby Matthews Community Center and the scenic Squirrel Lake Park provide ample opportunities for outdoor activities, family picnics, and leisurely strolls, ensuring that there’s always something to do.

Chestnut Oaks features a diverse selection of homes for sale, catering to various tastes and lifestyles. From charming single-family residences to modern townhomes, there’s a perfect fit for everyone. Many of these homes boast spacious layouts, contemporary finishes, and inviting outdoor spaces, making them ideal for both entertaining and relaxation. The real estate market in Chestnut Oaks is vibrant and competitive, offering a fantastic opportunity to invest in your dream home.

With its blend of community spirit, convenient location, and beautiful homes, Chestnut Oaks is not just a neighborhood; it’s a place where memories are made. Come explore the possibilities and discover the perfect home in this enchanting Matthews community!

Newest Chestnut Oaks Homes for Sale

$460,000

3 Beds ⋅ 3 Baths ⋅ 4400390 MLS ⋅ COMING SOON Status

Welcome to this beautifully maintained and updated Charleston-inspired Matthews home, where timeless curb appeal, thoughtful updates, inviting living spaces, and a convenient location come together to create the perfect place to call home. Featuring inviting double front porches, including a second-story porch just off the primary bedroom, this move-in-ready home offers the perfect place to enjoy your morning coffee, unwind in the evening, or relax on the screened porch. The kitchen was updated in 2021 with professionally painted cabinets, new countertops, a farmhouse sink, and a dishwasher. A new double-oven range and microwave were installed in 2023. Carpet and LVP flooring were done in 2021, while the AC and water heater were both replaced in 2020. The entire interior was painted in 2025, with the exception of two secondary bedrooms (one painted in 2021). Interior light fixtures were replaced in 2025. A new screened porch door was installed in 2026. Outside, the backyard was enhanced in 2022 with a stone patio, walkway, and stone planters, creating an inviting outdoor space for relaxing or entertaining. Ideally situated near an abundance of shopping, dining, grocery stores, parks, and healthcare facilities, this home offers exceptional convenience with easy access to everything you need for everyday living.

4140 Cedar Point Avenue, Matthews

Listing courtesy of Michael Andrew Group LLC. michaelncrealtor@gmail.com

$565,000

3 Beds ⋅ 3 Baths ⋅ 4398881 MLS ⋅ ACTIVE UNDER CONTRACT Status

Live in your own storybook village, where tree-lined streets wind past homes with inviting front porches, Victorian-inspired details, and the kind of architectural character rarely found in newer neighborhoods. Chestnut Oaks was designed to feel different—and from the moment you arrive, it does. That same sense of craftsmanship continues inside this home, where warm heart pine floors, wainscoting, decorative trim, and extensive stacked crown molding create spaces with depth, warmth, and personality. A soaring two-story foyer sets the tone, leading into a dramatic great room where vaulted ceilings and a stacked-stone fireplace create a natural centerpiece for both quiet evenings and lively gatherings. The kitchen sits at the heart of the home, with solid surface countertops, a tile backsplash, gas range, and an easy connection to the surrounding living spaces and outdoor deck. The main-level primary suite feels like a true retreat, offering a generous walk-in closet and spacious bath with dual vanities, separate tub and shower, and private water closet. Upstairs, the home continues to surprise. Two separate loft areas offer the freedom to create spaces that fit the way you live—perhaps a reading nook overlooking the living spaces below, a home office, media room, playroom, or creative studio. One loft also offers the potential to be enclosed, creating an additional bedroom, bonus room, or more private workspace as your needs change. Thoughtful details appear in unexpected places, from the barn door at the laundry area to the layers of millwork that give the home its distinctive character. Step outside to enjoy dinner on the deck, a weekend gathering with friends, or a quiet evening relaxing in the hot tub under the stars. In a world of cookie cutter neighborhoods, Chestnut Oaks stands apart. Here, architecture has personality, homes have character, and coming home feels a little like stepping into a story of your own.

1228 Saint Johns Avenue, Matthews

Listing courtesy of Keller Williams South Park. kbernard@empowerhome.com

$425,000

3 Beds ⋅ 2 Baths ⋅ 4392209 MLS ⋅ ACTIVE Status

*PRICE REDUCTION!* Charming and move-in ready, this beautifully maintained 1-story home offers the perfect blend of comfort and functionality. Featuring 3 bedrooms and 2 full baths, the home showcases neutral tones throughout, open floorplan, and two car garage. The spacious kitchen is the heart of the home, offering an open-concept layout with stainless steel appliances, abundant cabinet space, a large center island, and a charming breakfast nook complete with a cozy window seat. The generous primary suite features a tray ceiling and includes a relaxing en suite bath, while two additional bedrooms provide flexibility for guests, family, or a home office. Step outside to the inviting patio, perfect for entertaining friends and family or simply enjoying a quiet evening outdoors. A detached 2-car garage offers ample space for parking, storage, or hobbies. HVAC system updated in 2022.

1205 Gainsborough Drive, Matthews

Listing courtesy of Berkshire Hathaway HomeServices Carolinas Realty. jarod.orrell@bhhscarolinas.com

$338,000

3 Beds ⋅ 1 Baths ⋅ 4307170 MLS ⋅ ACTIVE Status

Seller is motivated! Bring your best offer! Welcome to your peaceful retreat in rural Chapel Hill, NC! Nestled on a full acre in a serene country setting, this charming home offers 1,098 square feet of comfortable living space in a wonderful neighborhood—ready for you to make it your own! Enjoy the quiet and privacy of rural life while still being conveniently close to everything Chapel Hill has to offer. With plenty of room to roam, this spacious lot is perfect for gardening, outdoor play, or simply relaxing under the Carolina sky. Recent updates provide peace of mind for years to come: Brand new roof installed in 2025 with a transferrable warranty Encapsulated crawl space (2025) with transferrable warranty Electric heat pump added in 2024 for efficient year-round comfort Luxury vinyl plank flooring throughout the home Ceiling fans in every room for added comfort The home is truly move-in ready and includes all appliances—microwave, dishwasher, refrigerator, and range—making your transition seamless. Whether you're looking for your first home, a quiet retreat, or a property with room to grow, this home checks all the boxes. Don’t miss out on this rare find—schedule your showing today!

2538 Gemena Road, Chapel Hill

Listing courtesy of Shelton Real Estate Center LLC. angiepugh335940@gmail.com

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