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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.
| DAYS ON MARKET | 18 | LAST UPDATED | 8/18/2026 |
|---|---|---|---|
| TRACT | Greenwood | YEAR BUILT | 1939 |
| GARAGE SPACES | 2.0 | COUNTY | Orange |
| STATUS | Active | PROPERTY TYPE(S) | Single Family |
| Elementary School | Chapel Hill Carrboro - Northside Elementary School |
|---|---|
| Jr. High School | Chapel Hill Carrboro - Grey Culbreth Middle School |
| High School | Chapel Hill Carrboro - East Chapel Hill High Schoo |
| ADDITIONAL DETAILS | |
| AIR | Ceiling Fan(s), Central Air, Electric, Heat Pump |
|---|---|
| AIR CONDITIONING | Yes |
| APPLIANCES | Bar Fridge, Built-In Refrigerator, Dishwasher, Dryer, Free-Standing Refrigerator, Gas Range, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Stainless Steel Appliance(s), Washer, Washer/Dryer, Wine Cooler |
| BASEMENT | Crawl Space, Yes |
| CONSTRUCTION | Fiber Cement |
| EXTERIOR | Balcony, Fire Pit, Garden, Lighting, Private Yard, Rain Gutters, Storage |
| FIREPLACE | Yes |
| GARAGE | Yes |
| HEAT | Electric, Fireplace(s), Forced Air |
| INTERIOR | Bar, Bookcases, Breakfast Bar, Built-in Features, Ceiling Fan(s), Central Vacuum, Chandelier, Crown Molding, Double Vanity, Entrance Foyer, High Ceilings, High Speed Internet, In-Law Floorplan, Kitchen Island, Master Downstairs, Pantry, Recessed Lighting, Smart Home, Soaking Tub, Track Lighting, Walk-In Closet(s), Wet Bar |
| LOT | 1.02 acre(s) |
| LOT DESCRIPTION | Back Yard, Few Trees, Garden, Landscaped, Secluded, Wooded |
| LOT DIMENSIONS | 1.02 |
| PARKING | Driveway, Garage, Parking Pad |
| POOL | Yes |
| POOL DESCRIPTION | Fenced, In Ground, Outdoor Pool, Private |
| PRIMARY ON MAIN | Yes |
| SEWER | Public Sewer |
| STORIES | 3+ |
| STYLE | Traditional |
| SUBDIVISION | Greenwood |
| TAXES | 28173.53 |
| UTILITIES | Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected |
| VIEW | Yes |
| VIEW DESCRIPTION | Forest, Trees/Woods |
| WATER | Public |
TOTAL MONTHLY PAYMENT
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Information Not Guaranteed.
Listings marked with an icon are provided courtesy of the Doorify MLS, Inc. of North Carolina, Internet Data Exchange Database.
Closed (sold) listings may have been listed and/or sold by a real estate firm other than the firm(s) featured on this website. Closed data is not available until the sale of the property is recorded in the MLS. Home sale data is not an appraisal, CMA, competitive or comparative market analysis, or home valuation of any property
Copyright 2026 Doorify MLS, Inc. of North Carolina. All rights reserved.
Data last updated: 9/4/26 6:08 PM PDT.
This IDX solution is (c) Diverse Solutions 2026.

