Oakley Real Estate

Welcome to Oakley, a charming subdivision nestled in the heart of Asheville, North Carolina! Known for its breathtaking natural beauty and vibrant community spirit, Oakley is a hidden gem that offers a perfect blend of suburban tranquility and urban convenience.

Situated in Buncombe County, Oakley boasts a variety of homes that cater to diverse lifestyles, from cozy cottages to modern family residences. The tree-lined streets are adorned with lush greenery, creating a picturesque backdrop for daily life. Residents here enjoy a strong sense of community, with friendly neighbors who take pride in their homes and the neighborhood.

One of Oakley’s standout features is its proximity to Asheville’s bustling downtown, where you can indulge in an array of local shops, art galleries, and farm-to-table restaurants. The area is also known for its rich cultural scene, with numerous festivals and events that celebrate the unique spirit of the region. Outdoor enthusiasts will appreciate the nearby parks and trails, perfect for hiking, biking, or simply enjoying the stunning mountain landscapes.

Families in Oakley benefit from access to quality schools and recreational facilities, making it an ideal place to raise children. With a variety of community events and activities, there’s always something happening to bring residents together.

In Oakley, you’ll find not just a place to live, but a vibrant community that welcomes you with open arms. Experience the charm of Asheville living in this delightful subdivision, where every day feels like a getaway in the beautiful Blue Ridge Mountains!

Newest Listings in Oakley

$525,000

3 Beds ⋅ 3 Baths ⋅ 4407595 MLS

Welcome to your move-in ready sanctuary in the highly desirable Oakley neighborhood! Perfectly positioned just minutes from the vibrant heart of downtown Asheville, this thoughtfully updated home offers the ultimate blend of mountain-city convenience and suburban tranquility. Step inside to discover a bright, inviting main level featuring three generously sized bedrooms all on one floor—a highly sought-after layout that ensures easy, accessible living. This home has been meticulously maintained and beautifully upgraded over the last few years. Enjoy cooking and entertaining with striking new quartz countertops, and rest easy knowing the heavy lifting has already been done for you with a recently updated HVAC system, hot water heater, and several other modern improvements. Need extra room to spread out? The finished lower level offers incredible versatility. Whether you are dreaming of a dedicated home gym, a cozy media room for movie nights, a quiet remote workspace, or a dedicated play zone, this expansive flex area is ready to adapt to your exact lifestyle needs. Outside, the property truly shines. The above-average, spacious fully fenced backyard is your private outdoor retreat. Gather around the custom fire pit or in the hot tub with friends and family to take full advantage of crisp Asheville autumns, cool Appalachian summer evenings, and every beautiful season in between. With its prime Oakley location, versatile square footage, and major recent upgrades, this home is completely turnkey and ready for its next chapter. Don't miss your chance to own a move-in ready piece of Asheville—schedule your private showing today!

29 Winding Road, Asheville

$409,900

3 Beds ⋅ 2 Baths ⋅ 4407081 MLS

Welcome to 376 School Road E in Asheville, North Carolina, a well-maintained 1,856-square-foot ranch home offering three bedrooms, two full bathrooms, thoughtful updates and a convenient Asheville location. This inviting property blends comfortable single-level living with practical features, a spacious family room, a fenced backyard, and move-in-ready appeal. The home presents a warm, welcoming atmosphere for everyday living, relaxing, and entertaining. The interior provides a comfortable and functional floor plan for a variety of needs, for hosting guests, working from home, enjoying hobbies, or creating separate gathering and relaxation areas. A large family room serves as one of the standout features of the home. This spacious gathering area offers room for seating, entertainment, games, reading, or time with family and friends. A warm wood stove creates a cozy focal point and adds character to the room, making it an especially inviting place during the cooler fall and winter months. Outside, the nicely fenced yard expands the home’s usable living space and provides a comfortable setting for recreation, relaxation, and privacy. Situated in Asheville, the property provides convenient access to the city’s restaurants, shops, cultural attractions, entertainment, outdoor recreation, and everyday services.

376 School E Road, Asheville

$350,000

2 Beds ⋅ 1 Baths ⋅ 4352652 MLS

Are small city lots making you feel limited with the space you can afford? This cute Oakley home sits on a large fenced-in 0.46 acre lot in a great section of Oakley full of trees and a great community. The home offers so much with recent renovations that include a NEW furnace and HVAC system, new flooring, new hot water heater, new paint inside and new lower cabinets in the kitchen and a new roof installed 2024! More improvements are listed in the attachments. If you want a great home in a great neighborhood and the ability to stroll to Biltmore Village and the new All Day Darling eatery easily, this home may be for you. Seller is offer a credit for a new refrigerator to the buyer in the amount of $1,000 as well. Make this bright and cheerful city home yours today!

49 First Street, Asheville

$399,000

3 Beds ⋅ 3 Baths ⋅ 4399525 MLS

Charming two-story traditional nestled on a cozy dead-end street in the desirable Oakley area of Asheville. This home combines comfort, functionality, and a peaceful setting just minutes from shopping, dining, schools, and Downtown Asheville. The main level offers a spacious living room, dining room that opens to the back patio, half bath and kitchen with stainless steel appliances. The upper level you will find all 3 bedrooms, and 2 full bathrooms for added privacy and convenience. The generous sized backyard is perfect for gardening, play, pets, or simply enjoying the outdoors.

17 Pinecrest Drive, Asheville

$495,000

3 Beds ⋅ 3 Baths ⋅ 4401592 MLS

Experience modern living in the heart of Oakley with this stunning new construction home! Featuring 3 bedrooms, 2 full baths, and a one-car garage, this thoughtfully designed home combines sleek contemporary style with everyday functionality. The open-concept floor plan is anchored by a beautifully appointed modern kitchen with clean lines, stylish finishes, and plenty of space to gather. The spacious primary suite offers a relaxing retreat, while the additional bedrooms provide flexibility for guests, a home office, or hobbies. Enjoy the convenience of being just a short walk to Oakley Elementary and only 7 minutes from vibrant downtown Asheville, where you'll find award-winning restaurants, shopping, breweries, and entertainment. This is the perfect opportunity to enjoy low-maintenance, modern living in one of Asheville's most desirable neighborhoods.

91 Winston Avenue, Asheville

$424,900

3 Beds ⋅ 2 Baths ⋅ 4398974 MLS

This comfy cottage is perfectly situated in a little pocket neighborhood of the sought-after Oakley community, possibly the best place to live in Asheville when it comes to getting around. Less than 10 downtown, 10 to South Asheville amenities, 5 to Biltmore Village, Whole Foods, or the Blue Ridge Parkway. Built in 2018, this place lives like new and has a perfect floor plan for everyday living. Everyone can spread out in the open living, kitchen and dining areas or sneak away for a private retreat with a split bedroom floor plan. And - this place offers a two car garage - such a rare amenity for in-town living. Cook together while friends gather at the island in the gorgeous kitchen appointed with white shaker-style cabinetry, granite countertops and quality stainless steel appliances. Grill out and dine al fresco with afternoon shade on the back deck. Or stroll over for breakfast, lunch and dinner at the upcoming All Day Darling being built just a few blocks away. Then wave at a neighbor and watch the sunset with a cool drink from the covered front porch. Live smart with newer construction, efficient HVAC, energy saving windows & doors, and a low maintenance yard. Live well with abundant natural light, wood floors throughout, and high caliber finishes including a walk-in shower with glass doors. Life is good in Oakley. Come on over and have your slice of the pie with a two car garage and all of the extras!

7 May Street, Asheville

$345,000

3 Beds ⋅ 1 Baths ⋅ 4399925 MLS

Fresh, stylish and full of opportunity, this beautifully updated 3BR/1BA home in the heart of Oakley is ready for its next chapter. Fresh interior paint creates a bright, like-new feel, while the stunning remodeled kitchen features new appliances, floating shelves, and designer finishes that elevate the home's modern appeal. Situated on a level .29-acre lot, the outdoor spaces are just as inviting, with a fire pit area, storage shed and covered carport/workshop perfect for hobbies, storage, or extra parking. Zoned RM-8, this property offers exceptional flexibility for future expansion, investment or redevelopment. An added bonus: the adjoining lot at 14 Main Street is also available for purchase, creating a rare opportunity to own nearly twice the space in one of Asheville's most convenient locations. Just minutes to Biltmore Village, downtown Asheville, shopping, dining and major highways, this move-in-ready property offers the perfect combination of comfort, location and potential!

16 Main Street, Asheville

$399,900

3 Beds ⋅ 3 Baths ⋅ 4393611 MLS

Price Adjusted - Exceptional value and peace of mind! Looking for an intelligent 3-bedroom, 3-bathroom home that optimizes your budget? Tucked quietly away from the street, this hidden gem features a brand-new HVAC system, removing big-ticket maintenance worries for years to come. The property features an expansive lower-level basement perfect for a workshop, home gym, or future finished equity. Enjoy an accessible entry point into the highly competitive Asheville market without sacrificing essential space or bedroom count. Location-wise, you are center stage to the best of Asheville. Easy Commutes: Enjoy effortless access to I-240, Downtown Asheville, and historic Biltmore Village. You are just a 0.2-miles from the upcoming, highly anticipated second location of the local favorite cafe, All Day Darling. Featuring off-street parking for up to 3 cars via a shared driveway, this home is private yet close to absolutely everything. Don’t miss your chance to own a piece of one of Asheville's hottest neighborhoods! Schedule your price tour today to discover the full potential.

501 Fairview Road, Asheville

$339,000

2 Beds ⋅ 1 Baths ⋅ 4385170 MLS

This charming bungalow on a quiet street in the heart of desirable Oakley was carefully and thoroughly restored from top to bottom in 2020. Upgrades include completely updated electrical, plumbing and heating/air systems, double-hung windows, new roof, Kohler bath fixtures, stainless GE appliances and much, much more. Cathedral ceilings in the main living area turn this small footprint into an airy, highly-flexible, low-maintenance space. Featuring a mix of period charms and modern conveniences, the home offers a unique blend of style, functionality and energy efficiency. Unscathed by Helene, the home is situated on high ground on a sunny, flat, spacious lot with future expansion potential, ideal for a detached garage, backyard ADU or a backyard gardener’s dream. Parcel has been identified as eligible for flag lot subdivision under Asheville’s updated UDO plan. Buyer to confirm. Situated with easy access to Interstates 40 & 240, Biltmore, and the Blue Ridge Parkway, this adorable home is close to everything the Asheville area has to offer!

130 Winston Avenue, Asheville

$129,000

4309679 MLS

This is a rare opportunity to secure the last of three premium plots in the center of Asheville’s Oakley neighborhood — a walkable community steeped in local history. The land and street carry the name of their original owner, L. L. Merchant, known for constructing Asheville’s tallest Gothic Revival building, The Jackson, in 1924. Designed with two anti-erosion terraces and a newly constructed rear retaining wall, this primed parcel is ready for your architectural vision. Direct connections are in place for natural gas, electricity, cable, city recycling, hydrant access, public works, and dedicated frontage for a city-installed sidewalk, meaning you can break ground without delay. In addition to the infrastructure, the land is already alive. Mature ten-year-old fruit trees — including Asian plum, apricot, and muscadine vine — produce thousands of pieces of fruit each season, making this not just a lot, but an urban orchard. The RS8 zoning unlocks extraordinary building potential that sets this lot apart from virtually anything else on the Asheville market. At 2,100 feet elevation with unrestricted views, a primary structure can rise to a full 40 feet — tall enough for a rooftop deck to capture panoramic views of Asheville’s iconic mountain sunsets over Mount Pisgah and the Blue Ridge. Better still, modern zoning also permits a separate Accessory Dwelling Unit (ADU) up to 25 feet tall, allowing an 800-square-foot guest house — flexibility that dramatically amplifies the investment value. A perfect location seals the case. Just one mile from Biltmore Village, Whole Foods, and Asheville Mall, and a five-minute walk to Oakley Park’s tennis and pickleball courts, the public library, and Oakley Elementary — and only one minute from the fire and police departments — 20 Merchant Street places you in one of the city’s most convenient and community-rooted neighborhoods. Contact me today and let’s make your dream home a reality.

20 Merchant Street, Asheville

Start Your Search

“The data relating to real estate on this website derive in part from the Internet Data Exchange program. Brokers make an effort to deliver accurate information, but buyers should independently verify any information on which they will rely in a transaction. All properties are subject to prior sale, change or withdrawal. Neither The M Homes Group nor any listing broker shall be responsible for any typographical errors, misinformation, or misprints, and they shall be held totally harmless from any damages arising from reliance upon this data. This data is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties they may be interested in purchasing. © 2026 Carolina Multiple Listing Services, Inc.”

Listings provided courtesy of Triangle MLS, Inc. of NC, Internet Data Exchange Database. Information deemed reliable but not guaranteed. © 2026 Triangle MLS, Inc. of North Carolina. Data last updated .