Greenwood Real Estate, Homes, Condos for Sale in Chapel Hill, NC

5 Beds ⋅ 4 Baths ⋅ 10022514 MLS ⋅ CLOSED Status

Rare opportunity to own four gorgeous acres in one of Chapel Hill's most desirable neighborhoods! Welcome to 610 Greenwood Road. Originally owned by Pulitzer Prize-winning playwright Paul Green, this historic home is truly one-of-a-kind. As you enter, you're greeted by the warmth and charm of this history-packed residence. The main floor boasts two inviting living areas, a formal dining room, an eat-in breakfast scullery, and a spacious kitchen. The stunning sunroom offers a spectacular view of the backyard. A downstairs bedroom, full bathroom, office, and laundry room complete the spacious first floor. Upstairs, you'll find the primary bedroom and bath, along with three additional bedrooms, an office, and a flex room. Outside, the privacy and natural beauty of the property are yours to enjoy. The lily pond, original to the house, provides a calming presence. The property also includes a one-bedroom, one-bathroom cottage and a separate garage. Opportunities like 610 Greenwood are rare—don't miss out!

610 Greenwood Rd, Chapel Hill

$693,000

5 Beds ⋅ 2 Baths ⋅ 10090775 MLS ⋅ CLOSED Status

Enjoy the good life in Greenwood! Step back into simpler times with this charming home that blends nostalgic warmth with modern convenience. Knotty yellow pine walls and ceiling wrap you in rustic comfort, while a welcoming screened porch overlooks the expansive front yard—perfect for sipping sweet tea and watching the world go by. Inside, the spacious family room centers around a stunning river rock fireplace, its stones hand-picked from the nearby Haw River. Thoughtful updates shine in the 2005-renovated kitchen, featuring artisan-crafted cabinet doors from Gibsonville and a commercial-grade, five-burner dual fuel range—ideal for the home chef. With flexible living options including a primary suite on either level and 4-5 bedrooms, there's room for everyone. Cozy up by the gas logs in both the living and family rooms, or venture downstairs to an unfinished, temperate recreation space, laundry area, storage room/workshop. You'll also find the oversized one-car garage. Out back, enjoy the large deck and follow the path through the lush setting to your very own pickleball court! Relax on the nearly one acre lot, just down the road from Battle Park, UNC's campus, Chapel Hill's Franklin Street, and a short drive to Durham, the RTP, and the airport. Enjoy one of the finest, friendliest college towns around! This home is a rare blend of past and present—come make it yours!

803 Old Mill Rd, Chapel Hill

$1,300,000

4 Beds ⋅ 5 Baths ⋅ 10095922 MLS ⋅ CLOSED Status

Sumner Winn designed 612 Greenwood in 1958, an exquisite example of his well-known modernist architecture. The home features his beautiful corner windows, two brick mass fireplaces, and gorgeous extended post and beam exterior eaves. 612 Greenwood is nestled in one of Chapel Hill's oldest and most beloved neighborhoods, George Smart, NCModernist.org says of Winn, ''The houses Sumner Winn designed in Chapel Hill stand as enduring testaments to his vision. Though many years have passed since his departure, the spirit of his work and the warmth of his character live on. The homes and buildings he conceived possessed a thoughtful integration with their surroundings, a harmonious blend of intention and natural beauty. Sumner Winn thoughtfully contributed to the fabric of Chapel Hill, and his buildings stand as silent yet powerful reminders of a creative spirit.'' This home was restored in 2001 with new plumbing, 3 zone HVAC, fully refinished hardwood floors 2025. Lovely Art Nouveau leaded-&-stained glass, clerestory & corner beveled windows, double shower, pool and a partially finished pool house is ready for your morning meditation. Extra storage/ workshop not photographed under the garage. Unfinished / unfinished spaces in this listing have been virtually staged.

612 Greenwood Rd, Chapel Hill

$1,205,000

3 Beds ⋅ 3 Baths ⋅ 10119156 MLS ⋅ CLOSED Status

SHOWINGS START 9/10/25* Artsy, casually elegant, comfortable, convenient, one-story Midcentury Modern treasure IN THE HEART OF CHAPEL HILL*Renovated and updated with loving care*Greenwood neighborhood *LOCATION, LOCATION, LOCATION *Walk to UNC, Franklin Street, Glen Lennox, University Place*Access to Battle Branch Trail directly from Greenwood* Private enclosed Courtyard*Zen garden*Large sunroom with gorgeous view of back yard and so much light!*Incredible native plant garden and paths thru out yard -all developed over the last 25 years*Bird watchers paradise*Partially finished workshop/art studio(345 sq ft) with its own HVAC-shown in MLS as unfinished space* A COOKS KITCHEN*A 9x13 butlers pantry *Cedar Closet*Primary Suite with adjacent zen garden and sumptuous bath*Incredible storage includes cedar closet and over 600 sq ft floored attic space*No detail overlooked*Inspected and repaired*inspection summary available upon request*Move in ready*See full description of special features in docs. You don't want to miss seeing this ONE OF A KIND treasure! OPEN HOUSE 9/13 12-2PM

817 Old Mill Rd, Chapel Hill

$1,041,000

4 Beds ⋅ 5 Baths ⋅ 10039077 MLS ⋅ CLOSED Status

Gorgeous traditional mid-century in woodsy Greenwood! Located on a quiet street a stone's throw from Battle Park and downtown Chapel Hill/UNC. Heart of pine flooring on the main level, nicely sized living room features a brick fireplace, open flow dining room, all with views of the luxurious inground pool- a glorious spot for entertaining! Eat in kitchen boasts Wolf stove, huge island, updated countertops, plentiful cabinetry, study can be a main level bedroom if called. Primary on the main level features an updated bath with custom walk-in closets; 2nd level has 3 beds, flex space, bonus room, all with new carpet. Lower level den perfect for gaming. Grounds are surrounded by beautiful oak trees. Separate apartment-two bedrooms, heart of pine hardwoods; great as a rental, multigenerational, or work from home potential.

629 Sugarberry Rd, Chapel Hill

$1,075,000

4 Beds ⋅ 3 Baths ⋅ 10091381 MLS ⋅ CLOSED Status

Welcome to Greenwood, a highly sought-after neighborhood in Chapel Hill, known for its picturesque tree-lined streets and prime location within the Triangle. This charming 1950s home sits on nearly an acre and offers a blend of comfort and character. All rooms are conveniently located on one floor, featuring a brand new roof, elegant built-in bookshelves, reclaimed doors, a claw-foot tub, a screened porch, a sunroom, marble countertops, and glass knobs. The spacious primary suite boasts double closets, a window seat, and tray ceilings. The fenced backyard, deck, and patio provide ample space for recreation and entertaining, with easy access to walking trails, UNC, and Battle Park. A detached studio offers a quiet retreat for hobbies or yoga. This rare gem combines historic charm with modern updates in one of Chapel Hill's most walkable and welcoming communities.

804 Old Mill Rd, Chapel Hill

$1,875,000

4 Beds ⋅ 4 Baths ⋅ 10117025 MLS ⋅ CLOSED Status

Perfectly positioned on a nearly level lot less than one mile from UNC, this impeccably maintained executive home offers an extraordinary blend of luxury, privacy, and walkable convenience. Whether you're seeking a serene retreat or an entertainer's dream, this residence delivers on every front. Step inside to discover an award-winning renovation that elevates everyday living. Luxe kitchen features an expansive island with counter seating, custom cabinetry, high-end appliances and fixtures. Accordion-style doors seamlessly connect the indoor living space to a tranquil courtyard, creating a year-round oasis for relaxation and entertaining. Just beyond, the main floor primary suite is a true retreat with bountiful light, a showstopping ensuite bath with double vanities, free-standing tub, walk-in shower with mosaic marble tile, and deluxe walk-in closet. Enjoy two spacious living areas on the main level, plus a dedicated office. Upstairs, you'll find three well-appointed bedrooms. Generous second floor bonus space has endless functionality for evolving needs. Additional walk-in storage ensures everything has its place.

100 Greenwood Ln, Chapel Hill

$985,350

3 Beds ⋅ 4 Baths ⋅ 10100733 MLS ⋅ CLOSED Status

Mid Century Deck house on beautiul .75 acre lot in desirable Greenwood. Soaring wood ceilings, huge windows and glass doors, some original lighting. Flexible floor plan with expansive living areas. Lower level family room and updated guest suite will have you asking your guests to go home! The bones are great and with a little updating (kitchen counters, 2 baths and some flooring) what a timeless beauty this home will be! Great outdoor areas.

808 Indian Springs Rd, Chapel Hill

$449,500

2 Beds ⋅ 2 Baths ⋅ 10128213 MLS ⋅ CLOSED Status

Welcome to this charming Chapel Hill bungalow, ideally located just minutes from UNC and downtown. Nestled on a serene half-acre wooded lot, this home offers both privacy and convenience. Inside, 9-foot ceilings and hardwood floors create an open, airy feel, while the cozy sunroom fills the living space with natural light. The kitchen features granite countertops and plenty of storage. The fully finished basement includes space for a potential third bedroom, a full walk-out entrance, and generous storage throughout. A peaceful retreat close to everything—ready for its next chapter.

106 S Christopher Rd, Chapel Hill

$510,000

4 Beds ⋅ 3 Baths ⋅ 10136827 MLS ⋅ CLOSED Status

This inviting ranch home offers flexible living with a fully finished basement and a private wooded setting. The main level features two bedrooms and one-and-a-half baths, a comfortable living room with a gas fireplace, and an attached garage. The lower level includes two additional bedrooms, a full bath, a spacious recreation room with a second gas fireplace, and a private entrance. The basement has previously served as a short-term rental, offering valuable versatility for guests or income. A deck overlooks the serene, wooded backyard, providing a peaceful outdoor retreat. Conveniently located near UNC, shopping, and dining, this home combines comfort, privacy, and exceptional convenience.

620 Sugarberry Rd, Chapel Hill

$2,250,000

5 Beds ⋅ 6 Baths ⋅ 10031997 MLS ⋅ CLOSED Status

Discover this stunning historic property in the desirable Greenwood neighborhood. Expertly renovated by Stan Stutts in 2000, this home seamlessly blends modern comforts with charming historic details. Nestled on a one-acre lot, it offers over 5,400 square feet of living space, plus a separate storage shed and workshop, solar panels, and a Tesla charger. The beautiful outdoor spaces and backyard are perfect for entertaining. The second level boasts four bedrooms, including a renovated primary suite. Hardwood floors grace the main level, which also features a lovely sunroom and study. The lower level includes a bedroom, office, ample storage, and a workout space with views of the rear of the home. Enjoy proximity to all that Chapel Hill has to offer!

713 Greenwood Rd, Chapel Hill

$400,000

10063322 MLS ⋅ ACTIVE Status

Wonderful chance to own a piece of Chapel Hill history. This 1.2 acre lot in Greenwood is ripe for your dream space. Accessible to city sewer and water. 2 miles to UNC, 4 miles to I-40, close to shopping, restaurants, and all the Chapel Hill has to offer.

636 Christopher Rd, Chapel Hill

$2,395,000

5 Beds ⋅ 7 Baths ⋅ 10082801 MLS ⋅ CLOSED Status

This unparalleled elegant home offers features rarely seen, inside and out! Complete privacy yet close to everything Chapel Hill and beyond. Modern, yet warm Sitzer-Spuria design. At every turn discover quality and intrigue: Antique French limestone, richly patinated copper panels and woven balcony, Anigre wood cabinets, In-ground pool with multiple waterfalls escaping the white stucco privacy wall, polished Brazilian Teak wood floors, stone accent walls, hidden glass display shelves, solid wood naturally stained interior doors and so much more. Main-level Primary Suite. Full In-Law Suite with private entrance. Dream-worthy closets! Complete Features List to come.

805 Greenwood Rd, Chapel Hill

$2,025,000

5 Beds ⋅ 8 Baths ⋅ 10057693 MLS ⋅ CLOSED Status

Experience luxury in this exceptional estate, situated in the iconic Greenwood neighborhood just a few miles from downtown Chapel Hill. Designed by award-winning UNC architect and Fulbright scholar Paul Kapp, this home combines modern craftsman aesthetics with superior craftsmanship and thoughtfully selected finishes. The exterior showcases a timeless design with cedar shakes, a copper-shingled roof, a charming wraparound porch, and exquisite landscaping accented by custom stone walls. Inside, ample windows and high ceilings create a bright and inviting atmosphere throughout. The main level flows effortlessly from the welcoming foyer to the spacious living room and the cozy family room. The gourmet kitchen is fully equipped for the discerning chef, featuring a six-burner Wolf range, double ovens, twin Bosch dishwashers, a large island with prep sink, and SubZero refrigerator. The primary suite is located at the rear of the home, with access to a back deck, two custom walk-in closets, and a spa-like bathroom complete with a sauna and washer/dryer. Three additional bedrooms on the second floor all feature ensuite baths with generous closets. A bonus/media room opens to a covered porch and leads to a massive walk-in attic, offering over 1,000 sq. ft. of potential space to be finished as desired. The lower level, completed by Will Johnson Building, includes a mirrored exercise room, fifth bedroom, wine room, full bath with shower, and an office/mudroom with direct access to the side yard. This level adds functionality and flexibility for any lifestyle needs. Additional features include a whole-house generator, three-car garage with exterior storage closets, a circular driveway, and a Tesla charging station. Bordering Battle Park, with more than two miles of trails leading to UNC and downtown, this estate offers the perfect balance of privacy and convenience in a highly coveted location. For those seeking exceptional quality, masterful design, and a prime address, this estate home is truly one-of-a-kind.

621 Sugarberry Rd, Chapel Hill

$970,000

6 Beds ⋅ 3 Baths ⋅ 10143917 MLS ⋅ PENDING Status

Just imagine owning a home celebrated for its American architectural design. 808 Christopher Road is a rare marvel nestled in Chapel Hill's highly coveted Greenwood neighborhood. Experience this stunning property, nearly 3,000 square feet with 6 bedrooms, 3 full bathrooms, and an expansive 1.12 acres of pure possibility. The Greenwood neighborhood is one of the most established enclaves in the heart of Chapel Hill, just a mile from UNC-Chapel Hill's campus. It was founded by Pulitzer Prize-winning playwright Paul Green in the 1930s. Green's visionary design wove 200 acres of natural woodland and majestic tall hardwoods into generous lots, each lot uniquely positioned to embrace nature's beauty with park-like serenity. Today, this legacy neighborhood continues to have deep roots that attract academics, professionals, urbanites, and naturalists alike... Location, location, and luxury. Step inside and feel the difference. This is where luxury meets livability in a brilliantly designed floor plan that flows effortlessly from relaxed moments to elegant entertaining. The sun-drenched main floor welcomes you with 2-3 bedrooms, including a serene primary suite with an ensuite bath, plus an additional full bathroom for the other bedrooms. A versatile flex space invites your imagination from home office, formal dining room, yoga sanctuary, or artist's studio; the choice is yours. Natural light floods the grand family room and gourmet kitchen, where integrated dining overlooks your expansive front yard. Upstairs, discover three generous bonus rooms, each with a closet, that are ready to become whatever your life demands: private bedrooms, a fitness haven, a creative workspace, or a quiet retreat. Every bathroom features spa-like finishes that will transform daily routines into moments of luxury. The smooth integration of indoor and outdoor spaces makes it easy to meander from a drink on the front porch to the central fire pit in the expansive yard or to the grill before congregating on the back porch for supper. This sunny, wooded, and nature-filled 1.12 acres treats you with a welcoming fire pit, water feature, nighttime lighting, and the space to create your dream outdoor oasis. From your long, private driveway, you can stroll across the pedestrian crosswalk to restaurants, coffee shops, and food markets. Enjoy easy access to the bus line, or walk to UNC campus, UNC Hospitals, and downtown Chapel Hill. This mid-century modern architectural design was awarded the title of ''The Smartest Traditional Home Ever...Enthusiasts of Traditional and Contemporary agree it is outstanding,'' published by Better Homes & Gardens. 808 Christopher Rd was marketed as the only one available ''Idea Homes'' opportunity to be purchased in all of North Carolina, September 1960 BHG. https://archive.bhg.com/issue/1960/9/. The local news agreed that it was an architectural treasure that captivated the audience the moment it graced the pages of national and, shortly thereafter, local publications. The prestigious ''Idea Homes of Better Homes & Gardens'' series represented the pinnacle of mid-century design. Toured nationwide, celebrated in glossy magazines, and coveted for their cutting-edge architecture and forward-thinking lifestyle innovations. The ''Idea Homes'' were revered for modern inspiration on point with the latest design trends, cutting-edge architecture, the use of the newest materials, and forward-thinking lifestyle innovations that blended nouveau modern conveniences with traditional beauty. Once the home of a beloved artist and art teacher, the possibilities for you with this marvelous property are endless. From an investment property to a personal residence, this home is ready for every stage of your life. 808 Christopher Rd is yours to imagine! With this New Year, leap into this showcased mid-century modern for your next luxury living property! https://808ChristopherRd.c

808 Christopher Rd, Chapel Hill

$2,660,954

5 Beds ⋅ 7 Baths ⋅ 2535815 MLS ⋅ CLOSED Status

The jaw-dropping, head-turning curb appeal of this 1939 Greenwood home is undeniable. Beautifully sited on a lush, private, one-acre wooded lot enclosed by its unique Jeffersonian serpentine brick wall. The home beckons the passerby with its iconic wrap-around, rocking chair front porch. Inside, fresh modern updates seamlessly merge with timeless finishes. Fabulous kitchen is a gourmet haven and features a Wolf range, custom cabinetry, dual dishwashers, wine refrigerator, ice maker, walk-in pantry+heated wood floors! Choose from TWO primary bedroom suites, one up, one down, both w/ spa-worthy bathrooms. While the indoor spaces are magnificent, it’s the outdoor spaces that truly set this home apart and are nothing short of extraordinary. A rooftop veranda (w/outdoor shower) overlooks a heated, saltwater pool+offers panoramic views of the stunning, meticulously landscaped grounds. Numerous spaces to entertain under the stars! Fully furnished 760 SF 1BR/1BA apt over garage has its own W/D+kitchen w/ SS appliances. Outstanding location just steps from Battle Park, UNC campus+hospital, PlayMakers, restaurants+shopping.

908 Greenwood Rd, Chapel Hill

$590,000

4 Beds ⋅ 3 Baths ⋅ 2523734 MLS ⋅ CLOSED Status

A wonderful opportunity to indulge your creativity in Greenwood; one of Chapel Hill’s prestigious neighborhoods bordering the UNC-CH Campus. Located on a mature .74 acre homesite you have the opportunity of a lifetime to make this one level home your own & completely reimagine it; or start from new & build. Offering 4-beds ( 1 in Apt ) , 3-baths(1 in Apt ) & an open concept living- dining area with expansive wall of glass. It's designed to bring the outside in from each window. The sep apartment sets this home apart with full kitchen, full bath & separate entrance. It features tile flooring and a cedar closet. Opportunities for multigenerational living, live-in care, a nanny ensuite, and a plethora of work from home options await you! All this and more near Battle Park, UNC Arboretum, and all things downtown Chapel Hill!

753 Old Mill Rd, Chapel Hill

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 2528727 MLS ⋅ CLOSED Status

What a find! This gorgeous 4 bed 2.5 bath updated ranch with a seperate 1 bed 1 bath ADU is nestled in the heart of Chapel Hill.This special property is privately set amidst wooded bliss on almost 1.5 acres. The heart of the home, the kitchen, has stainless steel appliances, quartz countertops & plenty of cabinet storage with a large island. Retreat to the main primary suite, w/ WIC and private deck. A large sitting room/exercise/ office space in primary allows for views of the beautiful backyard. Abundant windows throughout and expansive screened porch frame the lush treed landscape. A private oasis, yet close to town, highways and within the coveted Chapel Hill/Carrboro school system. Your serene retreat awaits to experience the magic of Chapel Hill living.

621 Greenwood Rd, Chapel Hill

Browse All Greenwood Properties for Sale

Greenwood Real Estate & Homes

Lunt Real Estate Group

Search

Resources

About