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 landscapes and close-knit community, Greenwood offers residents a serene lifestyle while being just moments away from the vibrant energy of downtown Chapel Hill. This delightful neighborhood is perfect for families, young professionals, and retirees alike, providing a welcoming atmosphere where neighbors become friends.

The homes in Greenwood are thoughtfully designed, featuring a blend of contemporary aesthetics and traditional charm. With spacious layouts, modern amenities, and beautifully landscaped yards, these residences cater to a variety of lifestyles. Many homes boast large windows that invite natural light, creating warm and inviting living spaces that are perfect for both entertaining and relaxation.

One of the standout features of living in Greenwood is its proximity to East Chapel Hill High School, a highly regarded institution known for its academic excellence and strong community involvement. Families with school-aged children will appreciate the convenience of having a top-tier school just a stone’s throw away, making daily commutes easy and stress-free.

In addition to its educational offerings, Greenwood is conveniently located near parks, shopping, and dining options, allowing residents to enjoy the best of Chapel Hill’s vibrant culture. Whether you’re exploring the scenic trails of nearby parks or indulging in local cuisine, Greenwood truly embodies the essence of North Carolina living. Discover your dream home in Greenwood and experience the perfect blend of comfort, community, and convenience in this idyllic Chapel Hill neighborhood.

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

$1,950,000

5 Beds ⋅ 5 Baths ⋅ 10193531 MLS ⋅ ACTIVE Status

Completely reimagined, renovated, expanded and rebuilt by Design Works Construction in partnership with favorite local architect Chad Wilkins, this home is a showstopper. Located in the heart of Greenwood, one of Chapel Hills most treasured neighborhoods, 753 Old Mill is ready for you to live the life you imagined! The main floor offers exceptional and expansive gathering space, perfectly scaled for the biggest bashes and intimate daily living. Pull up a seat at the island and take in the view of the extra large grassy lot and generous patio through the panoramic kitchen windows. A scullery and mud room offer all the practical space you need while making it possible to live gently and minimally...if that's your thing! 2 rooms and a full bath create the perfect main floor guest wing, office suite, or a bit of both and don't miss the in law suite/rec room at the far end complete with kitchenette, full bath, and private entrance and driveway. Upstairs 3 perfectly situated en suite bedrooms embrace abundant natural light and clean lines. Just the right room in just the right places. Back downstairs, a retracting paneled glass door brings the outdoors in. With a front porch, back patio, and rear covered porch as well, whatever the weather, 753 is a great place to be outside. And if you have World Cup Fever still, you will love the lighted practice field, perfect for training up the next Messi.

753 Old Mill Rd, Chapel Hill

$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

$2,900,000

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 .