Oakley Homes with AC Reynolds Middle School

Welcome to Oakley, a vibrant and welcoming neighborhood nestled in the heart of Asheville, North Carolina. Known for its charming tree-lined streets and friendly atmosphere, Oakley is a hidden gem that offers residents a perfect blend of suburban tranquility and urban convenience. With its close-knit community feel, this neighborhood is ideal for families, young professionals, and retirees alike.

One of the standout features of Oakley is its proximity to top-rated educational institutions, including the highly regarded AC Reynolds Middle School. Families will appreciate the quality education and supportive environment that this school provides, making Oakley a desirable location for those prioritizing their children’s learning and development. The school’s commitment to academic excellence and extracurricular activities fosters a sense of community and encourages student engagement.

Beyond education, Oakley boasts a variety of amenities that cater to everyday needs and leisure activities. Residents can enjoy local parks, walking trails, and community events that bring neighbors together throughout the year. A short drive or bike ride will lead you to the eclectic shops, restaurants, and cultural attractions of downtown Asheville, ensuring that you’re never far from the vibrant energy of the city.

Whether you’re looking for a cozy family home or a charming cottage, Oakley offers a diverse range of housing options that cater to various lifestyles and budgets. With its blend of community spirit, educational opportunities, and convenient access to the best of Asheville, Oakley is not just a place to live; it’s a place to thrive. Come discover your new home in this delightful neighborhood!

Newest Oakley Homes with AC Reynolds Middle School

$525,000

3 Beds ⋅ 3 Baths ⋅ 4407595 MLS ⋅ ACTIVE Status

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

Listing courtesy of Century 21 Connected. brokerchrissmith@gmail.com

$409,900

3 Beds ⋅ 2 Baths ⋅ 4407081 MLS ⋅ ACTIVE Status

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

Listing courtesy of NextHome Partners. brad@nexthome828.com

$350,000

2 Beds ⋅ 1 Baths ⋅ 4352652 MLS ⋅ ACTIVE Status

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

Listing courtesy of Carolina Mountain Sales. rachaelgiesenschlag@gmail.com

$399,000

3 Beds ⋅ 3 Baths ⋅ 4399525 MLS ⋅ ACTIVE Status

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

Listing courtesy of Property Mgmt Of Asheville. bly.pma@gmail.com

$495,000

3 Beds ⋅ 3 Baths ⋅ 4401592 MLS ⋅ ACTIVE Status

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

Listing courtesy of EXP Realty LLC. ClarissaSellsWNC@gmail.com

$424,900

3 Beds ⋅ 2 Baths ⋅ 4398974 MLS ⋅ ACTIVE Status

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

Listing courtesy of Town and Mountain Realty. jody@jodywhitehurst.com

$345,000

3 Beds ⋅ 1 Baths ⋅ 4399925 MLS ⋅ ACTIVE UNDER CONTRACT Status

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

Listing courtesy of Howard Hanna Beverly-Hanks Asheville-Biltmore Park. 828-702-2879

$339,000

2 Beds ⋅ 1 Baths ⋅ 4385170 MLS ⋅ ACTIVE UNDER CONTRACT Status

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

Listing courtesy of Town and Mountain Realty. athena@townandmountain.com

Start Your Search

“ Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Some IDX listings have been excluded from this website. Properties may or may not be listed by the office/agent presenting the information © 2026 Canopy MLS as distributed by MLS GRID”

Last Updated: