01Front - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial1 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial7 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial3 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial4 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
14FoyerView - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
12Foyer - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
13FoyerWithStairs - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
19EntryHallBuiltIns - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
16Dining - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
15Living - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
18WetBarArea - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
17CabinetBuiltIn - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
20Kitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
24Kitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
22Kitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
23Kitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
25CasualDining - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
21Kitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
27GatheringRoom - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
26GatheringRoom - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
28EnclosedPorch - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
29HallToPrimary - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
30Primary - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
31PrimaryFireplace - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
32PrimaryBath - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
33Bath - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
35Office - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
38Bedroom3 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
43ClosetInBedroom3 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
41BathWithShower - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
42BathwithShower - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
39Bedroom4 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
40FullBath - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
37Bedroom2 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
45ThirdFloorRoom - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
46ThirdFloorBath1 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
47ThirdFloorBath2 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
48WorkoutRoom - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
55Rooftop - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
50Pool - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
03Front - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial13 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
10FrontPorch - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
51Terrace - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
04FrontWalkway - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
05Front - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
06Sheep - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
07Driveway - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
08GarageExterior - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
09SidePorch - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
11CourtyardGate - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
34WasherDryerFirstFloor - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
36SecondFloorHallWithLaundry - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
44ThirdFloor - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
49Pool - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
50PoolView2 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
52Terrace - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
53Pond - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
54BackYard - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
55RoofTopStairs - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
56RoofTopShower - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
57Rooftop - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
58Playhouse - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
59SideYard - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
60Giraffe - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
61FloweringBush - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
62Back - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
63GardenShed - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
64Back - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
65BrickSidePatio - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
66WalkwayToApartment - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
67Apartment - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
68Apartment - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
69AptKitchen - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
70AptBedroom - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
71AptBath - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
908_GreenwoodFloorplan - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial2 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial5 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial6 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
Aerial8 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
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02Front - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
87 photos

$3,100,000

908 Greenwood Road, Chapel Hill, NC 27514
Chapel Hill, NC 27514
Listed by Laura Whayne · RE/MAX United
Bedrooms
5
Bathrooms
6.5
Living area
N/A
Year built
1939

About this home

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.

Highlights

Fireplace

Property details

MLS #
10185062
Property type
Single Family Residence
Subdivision
Greenwood
Status
Active
Days on market
42
On market date
August 18, 2026
Stories
N/A
Total bathrooms
6.5
Garage spaces
2
Parking spaces
N/A
Lot size
1.02 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
FPG Elementary
2.42 mi away · Grades -1-5
Zoned school (attendance boundary, 2015-16 data)
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
530
Student:teacher ratio
14.3:1
District
Chapel Hill-Carrboro City Schools
Middle
Culbreth Middle
2.52 mi away · Grades 6-8
Zoned school (attendance boundary, 2015-16 data)
3.6
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: C (2025)
Enrollment
664
Student:teacher ratio
11.6:1
District
Chapel Hill-Carrboro City Schools
High
East Chapel Hill High
3.34 mi away · Grades 9-12
Zoned school (attendance boundary, 2015-16 data)
4.4
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: A (2025)
Enrollment
1,475
Student:teacher ratio
16.4:1
District
Chapel Hill-Carrboro City Schools

Walkability

Blended score for Chapel Hill's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

80
Walkable
out of 100
EPA National Walkability Index
14.5 / 20 -- Above average walkable
Google Places amenity density
90 / 100
Restaurants & cafes20
Grocery stores2
Parks11
Schools9
Transit stops20
Pharmacies3

Market position

How this listing compares to current activity in Chapel Hill, from live MLS data.

On the market 42 days -- 74 fewer days than Chapel Hill's current average of 116 days.
For reference, the median list price across 625 active listings in Chapel Hill right now is $529,000.

Mortgage calculator

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Est. monthly payment
$18,819/mo
$620,000 down
$2,480,000 loan
Principal & interest$16,085
Property tax (est.)$2,583
Home insurance (est.)$150

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Data source: Listing information provided by Doorify MLS via Trestle/CoreLogic. Last updated August 23, 2026.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.