Greenwood Homes with Chapel Hill Carrboro - East Chapel Hill High School

Welcome to Greenwood, a charming subdivision nestled in the heart of Chapel Hill, North Carolina. Known for its picturesque streets and vibrant community spirit, Greenwood offers a perfect blend of suburban tranquility and urban convenience. This delightful neighborhood is located in Orange County, an area celebrated for its rich history, beautiful landscapes, and strong sense of community.

Homes in Greenwood boast a variety of architectural styles, catering to diverse tastes and preferences. From modern single-family homes to cozy townhouses, each residence is designed with comfort and functionality in mind. Many properties feature spacious yards, perfect for outdoor gatherings and family activities, while others showcase beautifully landscaped gardens that enhance the neighborhood's charm.

One of the standout features of Greenwood is its proximity to top-rated schools, including the esteemed East Chapel Hill High School. Families residing in this community benefit from access to quality education, making it an ideal choice for those looking to raise children in a nurturing environment. The school’s commitment to academic excellence and extracurricular activities ensures that students receive a well-rounded education.

In addition to its educational offerings, Greenwood is conveniently located near a plethora of shopping, dining, and recreational options. Residents can enjoy easy access to local parks, hiking trails, and cultural attractions, fostering an active lifestyle and a strong sense of community.

Whether you’re a first-time homebuyer or looking to settle down in a welcoming neighborhood, Greenwood in Chapel Hill is the perfect place to call home. Come experience the warmth and charm of this vibrant community today!

Newest Greenwood Homes with Chapel Hill Carrboro - East Chapel Hill High 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 .