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$875,000
4 Beds ⋅ 4 Baths ⋅ 10164400 MLS ⋅ CLOSED Status
A Legend Oaks Original -- And One of the Best. Some homes are maintained. This one has been cherished. Meticulously cared for by its original owners and custom built by Parker Orleans, this 4-bedroom, 3.5-bath beauty on nearly an acre in coveted Legend Oaks is a rare find in every sense of the word. Arrive to a full-length covered front porch made for rocking chairs and slow mornings. Step inside to a gracious entry foyer where real hardwood floors, soaring ceilings, and walls of windows set the tone immediately. The flow here is exceptional, living and dining rooms that are tailored for entertaining, a tucked-away home office with French doors for privacy, and a family room that connects effortlessly to the heart of the home. The chef's kitchen is nothing short of spectacular. Granite countertops, a massive island with seating, double ovens, a 5-burner gas cooktop, stainless steel French door refrigerator, abundant cabinetry, and a dedicated pantry -- it's all here. Adjacent to the kitchen, the sun-drenched morning room is one of those spaces you'll never want to leave, whether you're lingering over breakfast or curled up by the fireplace on a crisp winter morning. The primary suite features a trey ceiling and not one but two spectacular walk-in closets loaded with custom built-ins. The recently renovated luxury bath is pure indulgence with new cabinetry, granite countertops, double vanities, and a frameless walk-in shower with a gorgeous tile surround. Three additional bedrooms, a loft with rear stairs to the family room below, and an incredible flex room with vaulted ceilings and picture windows overlooking the park-like backyard. Use it as a media room, home gym, second office, or playroom- the possibilities are genuinely limitless. Outdoor Living at Its Absolute Best! The screened porch with skylights and ceiling fan is a four-season sanctuary. It opens to a spacious deck perfect for sunning, stargazing, or simply doing nothing at all. The yard itself is the crown jewel- a lovingly designed secret garden featuring mature native plants and trees, raised garden beds ready for spring planting, and a level of privacy that feels like your own personal nature preserve. The extra-wide turnaround does double duty as a driveway and a basketball court. A dedicated laundry room and drop zone with utility sink and cabinetry. Updated LED lighting and ceiling fans throughout. Custom blinds and shutters. A side-entry, 3-car oversized garage with workshop space. Legend Oaks offers a Chapel Hill address with the bonus of low Chatham County taxes. You're 5 minutes from three grocery stores, restaurants, a pharmacy, hardware store, and medical offices -- human and animal alike -- and just 15 minutes from UNC, Chapel Hill, and multiple top-rated golf courses. The neighborhood itself is a dream for walkers, runners, and cyclists. This is the one. Come see it before someone else does.

485 Legend Oaks Dr, Chapel Hill
$860,000
4 Beds ⋅ 4 Baths ⋅ 10147645 MLS ⋅ CLOSED Status
Welcome to your turn-key dream home! Looking for a beautifully maintained, clean, pristine and move-in ready home with every detail already perfected? Situated on 2+ private wooded acres, this stunning 4 BR, 3.5 Bath custom home offers solitude, relaxation and plenty of breathing room just minutes from the heart of Chapel Hill. From the moment you arrive, you'll notice the home is perfectly situated atop arguably one of the best lots in desirable Legend Oaks, backing to a level backyard with gorgeous, wooded views and overlooking a quiet cul-de-sac in front! The interior shines with natural light, 10-FT ceilings and special features throughout - see all home upgrades/features list attached. The heart of the home is an open-concept great room with gas fireplace and a gourmet kitchen including 5-burner gas range, double wall ovens, custom bar & breakfast room, all highlighted by real hardwood floors (throughout majority of home), a huge center island, and seamless flow to the screened porch and deck overlooking a picturesque, wooded setting! The main level boasts a luxurious primary suite with both ''duelling'' walk-in closets & ''duelling'' bathroom vanities with a large garden tub and separate walk-in shower. Completing the easy main-level living is a spacious private office with French doors, formal dining room and 1st floor laundry room. Upstairs, you'll find 3 additional bedrooms, 2 full bathrooms (1 en-suite) and an expansive raised bonus/game/flex room. Multiple trey ceilings, LED's everywhere, Stainless steel appliances including W/D all convey, tons of storage inside/outside, newer HVAC's (2022/23), tankless water heater with circulator, and much more make life easy and low- maintenance. Located in this large lot vibrant community right on the edge of Chapel Hill - with low Chatham County taxes - this location combines peaceful living with unbeatable convenience. Enjoy easy access to: UNC Hospitals (<15 min), Southern Village Parks, the NC Botanical Gardens, Jordan Lake, Downtown Carrboro, Fearrington Village, RDU Airport (30 min), entertainment and events at Playmakers Theatre or Kenan Stadium. Don't miss your chance to come see your new home lovingly cared for by the original owners and custom built by Parker Orleans!

76 S Duelling Oaks Dr, Chapel Hill
$739,900
3 Beds ⋅ 3 Baths ⋅ 10120875 MLS ⋅ CLOSED Status
This beautiful home is at the end of a cul-de-sac on a large flat 1.13 acre landscaped lot. Open floor plan with 2 story family room with new hardwood floors and walls of windows provide great natural light. Wonderful eat in kitchen that opens to back deck has new double ovens, new dishwasher, granite, stainless, & center island. Dramatic wrought iron staircase to 2nd floor bedrooms and bonus room. Large primary bedroom is on main floor with sitting area, tray ceilings. Master bath with double vanities, separate soaking tub, shower, and water closet. Well appointed dining room perfect for entertaining. Beautiful study with custom bookcases. Side entrance garage with electric car re-chargers. Solar panels save approximately $1,300 per year and the powerwall battery mounted in the garage provides an uninterruptible power supply when public utilities are down. House is wired for sound and has a sprinkler system.

99 Grassy Creek Way, Chapel Hill
$687,500
4 Beds ⋅ 3 Baths ⋅ 10127456 MLS ⋅ CLOSED Status
Beautiful Home in Legend Oaks — Spacious, Bright & Perfectly Located! Welcome to this beautifully maintained home in the sought-after Legend Oaks subdivision, offering the perfect blend of privacy and convenience. Ideally located near shopping and just minutes from Chapel Hill, this residence sits on a large, wooded lot at the end of a quiet cul-de-sac — a peaceful retreat surrounded by mature landscaping. Step inside to find a light-filled two-story home with a flexible floor plan designed to fit a variety of lifestyles. The spacious foyer opens to a versatile room that's perfect as a home office, library, or sitting room, flowing seamlessly into the formal dining room. Across the back of the main level, you'll love the open-concept living area featuring a family room with fireplace, a sunny breakfast nook, and a chef's kitchen with a large island and abundant cabinet and counter space. Enjoy indoor-outdoor living with access to the screened porch and deck, overlooking a private backyard sanctuary complete with a storage shed (conveys). Upstairs, a bright and airy loft anchors the second floor, leading to an expansive primary suite with a sitting area and a huge walk-in closet. Three additional spacious bedrooms provide plenty of room for family, guests, or hobbies. This exceptional home offers space, style, and comfort in a serene setting — truly a must-see! Home warranty included.

106 N Duelling Oaks Dr, Chapel Hill

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 .