Greenwood Homes with Chapel Hill Carrboro - Grey Culbreth Middle School

Welcome to Greenwood, a charming subdivision nestled in the heart of Chapel Hill, North Carolina. This picturesque community is perfectly situated in Orange County, offering residents a serene suburban lifestyle while being just a stone's throw away from the vibrant culture and amenities of Chapel Hill.

Greenwood is known for its beautifully designed homes, which range from modern townhouses to spacious single-family residences, catering to a variety of lifestyles and preferences. With well-maintained streets and lush landscaping, the neighborhood exudes a warm and inviting atmosphere, making it an ideal place for families, young professionals, and retirees alike.

One of the standout features of Greenwood is its proximity to top-rated educational institutions, including the esteemed Chapel Hill Carrboro - Grey Culbreth Middle School. Families residing in this subdivision can take pride in knowing their children have access to quality education within a supportive community. The school is renowned for its dedicated staff and engaging curriculum, ensuring that young learners receive the best foundation for their future.

In addition to its excellent schools, Greenwood offers residents a range of recreational opportunities. Nearby parks and green spaces provide the perfect backdrop for outdoor activities, while local shops and restaurants add to the vibrant community feel. Whether you're looking for a peaceful retreat or an active lifestyle, Greenwood has it all.

Discover the charm of Greenwood today and experience the perfect blend of community, education, and convenience in one of North Carolina’s most desirable locations. Your dream home awaits!

Newest Greenwood Homes with Chapel Hill Carrboro - Grey Culbreth Middle School

$995,000

5 Beds ⋅ 4 Baths ⋅ 10190810 MLS ⋅ ACTIVE Status

Nestled among beautiful mature trees in one of Chapel Hill's premier neighborhoods, Greenwood, which was created by Pulitzer-Prize winning playwriter, Paul Green, this all-brick home offers timeless charm, flexible living space, and endless potential. Hardwood floors, skylights, and a whole-house fan fill the home with natural light and comfort, while the spacious deck overlooks a peaceful setting. The heated & cooled sunroom (a later addition) offers a warm & cozy experience. The kitchen features granite countertops, granite backsplash, stainless steel appliances, and a gas cooktop. The daylight walkout basement includes a large apartment with its own kitchen, full bath, living space, and private entrance—ideal for multi-generational living, guests, or a home office. Additional features include a wood stove insert, pull-down attic storage, gas heat, and no HOA. A rare opportunity to make this well-built home your own in a beautiful, established setting.

611 Greenwood Rd, Chapel Hill

$3,100,000

5 Beds ⋅ 7 Baths ⋅ 10185062 MLS ⋅ ACTIVE Status

Undeniable curb appeal announces this extraordinary 1939 Greenwood estate before you even step inside. Set on a private, one-acre wooded lot and cloaked in mystery by its rare Jeffersonian serpentine brick wall, the property unfolds along a brick paver, wood-lined walkway to an iconic wrap-around porch — the kind built for rocking chairs, sweet tea, and long evenings. Step through the door and discover a masterful blend of old-world character and modern luxury across three finished levels. Gleaming hardwood floors flow throughout light-filled rooms, anchored by a gathering room framed in a wall of windows, transom detail, and custom built-ins. The chef's kitchen is a study in refinement: a Wolf gas range, dual dishwashers, wine refrigerator, ice maker, walk-in pantry. A sophisticated wet bar, complete with glass-front cabinetry, sets the stage for effortless entertaining. Rest and retreat are equally elevated with 2 exquisite primary suites — one on each level — offering spa-caliber bathrooms appointed with a classic claw-foot soaking tub, oversized walk-in closets, and separate glass showers. A third-floor retreat adds even more flexibility, room perfect for a bedroom/office/playroom, full bath, and private gym — ideal for guests, a home fitness studio, or a peaceful work-from-home escape. The outdoor living is every bit as extraordinary as what's found within. Ascend from the upper primary suite to a private rooftop veranda, then descend a graceful spiral staircase to a fully fenced, resort-style rear yard centered on a stunning heated pool — a private oasis designed for al fresco entertaining beneath the stars. Completing this exceptional offering is a fully furnished 708-square-foot guest apartment or in-law suite above the garage, thoughtfully finished with its own kitchen, stainless appliances, washer/dryer, and a generous 13x16 living room — perfect for guests, extended family, or a private studio retreat. Ideally situated just moments from Battle Park, the University of North Carolina campus and hospital, PlayMakers Repertory Company, and Chapel Hill's finest dining and shopping — this is a rare offering where timeless architecture meets uncompromising luxury.

908 Greenwood Rd, Chapel Hill

$375,000

10063322 MLS ⋅ ACTIVE Status

Wonderful chance to own a piece of Chapel Hill history. This 1.2 acre lot in Greenwood is ripe for your dream space. Accessible to city sewer and water. 2 miles to UNC, 4 miles to I-40, close to shopping, restaurants, and all the Chapel Hill has to offer.

636 Christopher Rd, 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 .