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
Aerial9 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
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Aerial12 - 908 Greenwood Road, Chapel Hill, NC 27514, Chapel Hill
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
6.1
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
9
On market date
August 18, 2026
Stories
N/A
Total bathrooms
7
Garage spaces
2
Parking spaces
N/A
Lot size
1.02 acres
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Nearby schools

Within 10 miles · public school directory data (NCES)

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

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 5 days ago.

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.