Chestnut Oaks Homes for Sale

Welcome to Chestnut Oaks, a hidden gem nestled in the heart of North Carolina, where tranquility meets modern living. This charming subdivision offers a perfect blend of suburban comfort and natural beauty, making it an ideal place for families, retirees, and anyone looking to embrace a peaceful lifestyle.

Chestnut Oaks is characterized by its picturesque tree-lined streets, spacious lots, and beautifully designed homes that reflect a variety of architectural styles. Each residence is thoughtfully crafted to provide both aesthetic appeal and functional living spaces, ensuring that every family can find their perfect sanctuary. With homes for sale that cater to diverse tastes and budgets, this community is ready to welcome new neighbors who appreciate quality and charm.

Residents of Chestnut Oaks enjoy a wealth of amenities, including well-maintained parks, walking trails, and recreational areas that encourage an active lifestyle. The community also boasts a strong sense of camaraderie, with friendly neighbors who gather for seasonal events and neighborhood activities, fostering connections that make living here truly special.

Conveniently located near shopping centers, top-rated schools, and major highways, Chestnut Oaks offers easy access to everything you need while maintaining a serene atmosphere. Whether you're seeking a cozy family home or a spacious retreat, Chestnut Oaks has something for everyone.

Explore the homes for sale in Chestnut Oaks today and discover the perfect place to call home in this vibrant and welcoming community. Your dream home awaits!

Newest Chestnut Oaks Homes for Sale

$460,000

3 Beds ⋅ 3 Baths ⋅ 4400390 MLS

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. Professional photos and measurements will be uploaded August 5.

4140 Cedar Point Avenue, Matthews

$565,000

3 Beds ⋅ 3 Baths ⋅ 4398881 MLS

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

$425,000

3 Beds ⋅ 2 Baths ⋅ 4392209 MLS

*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

$396,770

4 Beds ⋅ 6 Baths ⋅ 1218960 MLS

Bring us your offer. Many furnishings stay. We are serious about getting this large townhome to the next owner. 4 PRIMARY Bedrooms with ensuite baths. Rare opportunity to own an exceptionally spacious home designed for comfort, flexibility, & easy living. Most exterior maintenance & yard work are handled by the HOA, allowing you to relax & enjoy life. Incredible value per sq ft with a layout ideal for multi-generational living & guests. This unique property features 2 garages & 2 separate driveways. Lower level includes a private entrance, patio, great room, huge bedroom, & 2 full baths — all on one level. You'll also find a powder room, spacious great room, dining room, & bright eat-in kitchen w/skylight, & walk-in pantry. Enjoy mornings on the charming front porch with swing & puppy gate. Oversized rooms, abundant closets, & extensive storage. Agent related to seller. Review the floor-plan & room sizes — C this home to appreciate all it offers. Down from 450k - no known issues.

633 Huntington Drive, High Point

$338,000

3 Beds ⋅ 1 Baths ⋅ 4307170 MLS

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

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Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .