Vintage homes for sale & real estate in 27514, NC

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ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
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 refineme

$3,100,000

5 beds6.5 baths5,794 sq ft

908 Greenwood Rd, Chapel Hill, NC 27514

Dual dishwashers • Wine refrigerator • Private wooded lot

VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
This brick duplex offers strong rental potential and could also be converted into a single-family home, thanks to its desirable neighborhood and convenient proximity to UNC. The main apartment includes two bedrooms, a full bath, a living room with a fireplace and solid wood paneling, a kitchen, and hardwood floors. The efficiency apartment features a combined living/bedroom area, a small kitchen, and a full bath. Large front and back porches add outdoor living space. Set on a flat . 52-acre corner lot, the property includes mature trees and shrubbery, along with ample yard and gardening space. Whitehead Circle is a low-traffic community adjacent to the south campus medical schools and hospi

$625,000

3 beds2 baths1,541 sq ft

423 Whitehead Cir, Chapel Hill, NC 27514

Solid wood paneling • Hardwood floors • Outdoor living space

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Welcome to this charming three-bedroom, two-bathroom single-family residence nestled in established North Forest Hills subdivision. Just minutes from UNC campus, downtown Chapel Hill along with several NC Official Tourism Site attractions. This Corner lot offering beautiful Lake Front views and access to Lake Ellen. This home offers ample outdoor space, stunning scenery, tranquil creek view, and scenic nature watching for homeowners who appreciate room to breathe. Eat in kitchen, convenient single-car garage, and plenty of basement space to grow. Whether seeking a comfortable peaceful retreat, in the Chapel Hill area or a solid residential investment, this residence provides the foundation

$599,000

3 beds2 baths1,920 sq ft

122 Taylor St, Chapel Hill, NC 27514

Tranquil creek view • Access to lake ellen • Outdoor space

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Priced well below tax value. A wonderful downtown historic home ready for anything!! Rental? Couldn't be better with wonderful rental history and fantastic location. Or how about your HGTV fantasy renovation? Take this 1928 building and transition it to a fantastic 2026 gem. Choice is yours and you win either way. Stunning hardwood floors and detailing throughout. Roof (2025) See Historic District guidelines for details on renovation options. Move in ready no matter what you choose. Front has a rocking chair porch, classic stonework and stunning hydrangeas. Large basement storage with washer/dryer and sunny back deck. Some photos virtually staged. Property records show home built in eit

$719,000

3 beds2 baths1,645 sq ft

217 Hillsborough St, Chapel Hill, NC 27514

Sunny back deck • Downtown chapel hill • Historic home

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
RARE OPPORTUNITY to own the historic Gabriel Utley House (c. 1849), a landmark residence and Contributing Building within the Chapel Hill Historic District, ideally located at 303 E. Rosemary Street, Chapel Hill, NC, near downtown Chapel Hill and the University of North Carolina. Believed to date to approximately 1849, this remarkable home blends more than 175 years of Chapel Hill history with thoughtful modern updates. Architectural historians have identified the property as a Greek Revival-style residence, and historic records indicate it stands on land that was part of Chapel Hill's original town lots established in 1793. Preservation research suggests portions of an earlier structure ma

$1,400,000

4 beds2 baths2,152 sq ft

303 E Rosemary St, Chapel Hill, NC 27514

0.3 acre lot • 9 parking spots • Built 1849

Property at 321 Woodhaven Rd, Chapel Hill, NC 27514, 4 beds, 2 baths

$1,400,000

4 beds2 baths2,040 sq ft

321 Woodhaven Rd, Chapel Hill, NC 27514

Property at 100 Eastwood Lake Rd, Chapel Hill, NC 27514, 4 beds, 4 baths

$775,000

4 beds4 baths2,243 sq ft

100 Eastwood Lake Rd, Chapel Hill, NC 27514

Property at 223 Hillcrest Cir, Chapel Hill, NC 27514, 4 beds, 4.5 baths

$3,450,000

4 beds4.5 baths3,534 sq ft

223 Hillcrest Cir, Chapel Hill, NC 27514

Property at 210 Purefoy Rd Unit 1-6 And A&B, Chapel Hill, NC 27514, 9 beds, 8 baths

$950,000

9 beds8 baths4,320 sq ft

210 Purefoy Rd Unit 1-6 And A&B, Chapel Hill, NC 27514

Property at 213 E Franklin St Unit 400, Chapel Hill, NC 27514, 3 beds, 3.5 baths

$1,899,000

3 beds3.5 baths2,455 sq ft

213 E Franklin St Unit 400, Chapel Hill, NC 27514

Property at 401 Laurel Hill Rd, Chapel Hill, NC 27514, 3 beds, 2.5 baths

$2,985,000

3 beds2.5 baths2,862 sq ft

401 Laurel Hill Rd, Chapel Hill, NC 27514

Property at 106 Markham Dr, Chapel Hill, NC 27514, 3 beds, 2 baths

$450,000

3 beds2 baths1,377 sq ft

106 Markham Dr, Chapel Hill, NC 27514

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ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
A documented mid-century modern by architect Edward W. Waugh, AIA, one of the original faculty members at NCSU's School of Design and one of North Carolina's most influential modernist architects. 'Terry' Waugh is known for his low-slung, glass-forward residential work throughout Raleigh and Chapel Hill in the 1950s. Built in 1956 and set on a wooded lot in University Heights, this home carries the hallmarks of Waugh's design language: an informal plan built around the site rather than against it. The original wood paneling in the living room, the material signature of the era and this architect, survives beneath a later application of paint; this may be a reversible cosmetic restoration f

$760,000

4 beds3 baths2,530 sq ft

425 Brookside Dr, Chapel Hill, NC 27516

Mid-century modern • Private entrance • Focal fireplaces

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Dreaming of owning a historic bungalow? This 1930's home in the heart of Chapel Hill could be yours. Situated in the Cameron-McCauley Historic District, this updated home has location and charm. This home includes 2 bedrooms, with an updated bathroom, and a separate updated powder room. Updated kitchen cabinetry, stainless appliances, quartz counters with breakfast bar, farmhouse sink, and custom tile backsplash. This open floor plan shows off the beautiful hardwood floors, and stained heart of pine ceilings. Built-in bookshelves, crown moldings, glass door knobs are just some of the original charm kept throughout the home. The laundry room/mudroom was updated and includes side by side wash

$810,000

2 beds1.5 baths1,224 sq ft

304 Mccauley St, Chapel Hill, NC 27516

Quartz counters • Historic bungalow • Stainless appliances

3D & VIDEO TOUR

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Classic Ridgefield home with a two-car garage on a large, flat lot with mature trees and landscaping. The front door opens to a foyer and center hall with a staircase to the second floor. The main level features a spacious living room with windows on three sides, a dining room with a picture window, and a kitchen with granite counters, tile backsplash, pantry, and breakfast area. Glass doors lead to a generous screened porch, and the adjoining family room adds comfortable gathering space. A large study with built-in shelving and a full bath complete the main floor. Upstairs are three bedrooms and two remodeled bathrooms, with hardwood floors throughout both levels. Recent updates include tw

$625,000

3 beds3 baths2,208 sq ft

1307 Leclair St, Chapel Hill, NC 27517

New hvac systems • Large flat lot • Screened porch

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Classic charm meets lasting quality in this timeless one-story brick home. Built for durability and designed for comfortable, easy living, this 4-bedroom, 2-bath residence offers the convenience of a single-level floor plan. Inside, you'll find the distinctive character of a mid-century home, featuring gleaming hardwood floors, a cozy wood-burning fireplace with an insert, and abundant windows that fill the space with natural light. Relax on the inviting covered front porch, the perfect spot to enjoy the surrounding neighborhood and outdoor scenery. Ideally located in the heart of Chapel Hill, this property offers exceptional versatility. Its close proximity to the university and hospital m

$455,000

4 beds2 baths1,265 sq ft

309 Caldwell St, Chapel Hill, NC 27516

Covered front porch • One story brick home • Mid century home

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Experience graceful living in the heart of Chapel Hill, located between the Cameron-McCauley and Westwood Historic Districts. 416 Brookside Drive provides all the amenities of walkable proximity to campus, UNC Hospital, Downtown Carrboro and Franklin Street but with the tranquility and privacy of a haven nestled seemingly deep in the woods. Relax with morning coffee or evening fires on the delightfully private, back patio featuring a pergola, an outdoor fireplace, kitchen with Big Green Egg, mini-fridge, sink and even an outdoor shower! Enjoy entertaining friends and family in this party perfect property (tailgating anyone?) with a large, gourmet kitchen featuring a professional style six b

$1,100,000

4 beds4 baths3,508 sq ft

416 Brookside Dr, Chapel Hill, NC 27516

Outdoor fireplace • Gourmet kitchen • Daylight basement

ABOUT THIS HOME
Vintage Home for sale in 27514, NC:
Updated 3BR/1BA RANCH w/ 1,011 SF! Renovated in 2026 w/ a NEW roof, NEW kitchen cabinets, NEW countertops, NEW stainless steel range, NEW paint, NEW vinyl flooring, Refinished HARDWOODS, NEW bath vanity, NEW lighting, and NEW fixtures. Perfect for an owner-occupant or investor! Private 0.23-acre lot with no HOA and no subdivision. Located in the desirable Chapel Hill/Carrboro School District. Walk to Wegmans! Minutes to Franklin St, UNC, shopping, dining, and the bus line.

$375,000

3 beds1 bath1,011 sq ft

203 Scarlett Dr, Chapel Hill, NC 27517

New paint • New kitchen cabinets • New countertops

Property at 803 Branch St, Chapel Hill, NC 27516, 2 beds, 1 bath

$265,000

2 beds1 bath805 sq ft

803 Branch St, Chapel Hill, NC 27516

Property at 811 Kings Mill Rd, Chapel Hill, NC 27517, 5 beds, 3.5 baths

$975,000

5 beds3.5 baths3,342 sq ft

811 Kings Mill Rd, Chapel Hill, NC 27517

Property at 123 Windsor Cir, Chapel Hill, NC 27516, 3 beds, 2 baths

$575,000

3 beds2 baths1,710 sq ft

123 Windsor Cir, Chapel Hill, NC 27516

Property at 2112 U.s. Hwy 70a E, Hillsborough, NC 27278, 2 beds, 1 bath

$250,000

2 beds1 bath821 sq ft

2112 U.s. Hwy 70a E, Hillsborough, NC 27278

Property at 101 Hanna St, Carrboro, NC 27510, 3 beds, 1.5 baths

$499,000

3 beds1.5 baths1,235 sq ft

101 Hanna St, Carrboro, NC 27510

Property at 4204 Kerley Rd, Durham, NC 27705, 3 beds, 2.5 baths

$965,000

3 beds2.5 baths3,536 sq ft

4204 Kerley Rd, Durham, NC 27705

Property at 218 Hillsborough Rd, Carrboro, NC 27510, 4 beds, 2.5 baths

$2,125,000

4 beds2.5 baths2,308 sq ft

218 Hillsborough Rd, Carrboro, NC 27510

Property at 404 Northside Dr, Chapel Hill, NC 27516, 3 beds, 1.5 baths

$399,900

3 beds1.5 baths1,056 sq ft

404 Northside Dr, Chapel Hill, NC 27516

Property at 213-223 Mccauley St, Chapel Hill, NC 27516, 7 beds, 3 baths

$6,500,000

7 beds3 baths3,868 sq ft

213-223 Mccauley St, Chapel Hill, NC 27516

Property at 01 Collins Mountain Rd, Chapel Hill, NC 27516

$2,499,900

Land89.39 acres (lot)

01 Collins Mountain Rd, Chapel Hill, NC 27516

Vintage Homes for Sale in 27514

There are currently 12 vintage homes for sale in 27514 at a median listing price of $599K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 27514 stay on the market for 73 days and receive 6 offers. This map is refreshed with the newest listings in 27514 every 15 minutes.

In the past month, 19 homes have been sold in 27514. In addition to houses in 27514, there were also 51 condos, 19 townhouses, and 2 multi-family units for sale in 27514 last month. Find your dream home in 27514 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 27514 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 27514. If you're looking to sell your home in the 27514 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 27514 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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