908 Greenwood Road

Chapel Hill, NC 27514

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.

Listing courtesy of Laura Whayne of RE/MAX United



Listings that are marked with an icon are provided courtesy of the Triangle MLS, Inc. of North Carolina, Internet Data Exchange Database. Copyright 2026 Triangle MLS, Inc. of North Carolina. All rights reserved.

Last checked: 2026-08-10 11:17 AM UTC