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29 Winding Road, Asheville
$525,000
3 Beds ⋅ 3 Baths ⋅ 4407595 MLS ⋅ CLOSED 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

Sold listing courtesy of Town and Mountain Realty
91 Winston Avenue, Asheville
$479,000
3 Beds ⋅ 3 Baths ⋅ 4401592 MLS ⋅ CLOSED 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

Sold listing courtesy of Town and Mountain Realty
3 Fourth Street, Asheville
$420,000
3 Beds ⋅ 3 Baths ⋅ 4320976 MLS ⋅ CLOSED Status
This is a beautiful 2 level new construction home in the heart of Oakley! This house is very spacious with 1514 square footage. Where the modern design meets every day comfort. Thoughtfully crafted with high-end finishes and an open concept layout. Laundry room on main level. About a 15-20 Minute drive to downtown Asheville. About a 5 minute drive to the Biltmore Estate area. New construction tax value will be subject to change on this property.

3 Fourth Street, Asheville

Listing courtesy of CENTURY 21 Mountain Lifestyles. bree@c21hialta.com

Sold listing courtesy of EXP Realty LLC
34 Oakley Road, Asheville
$345,000
2 Beds ⋅ 1 Baths ⋅ 4371433 MLS ⋅ CLOSED Status
Located in the desirable Oakley neighborhood, offering comfort, character, and convenience just minutes from Biltmore Village, downtown Asheville, and the Blue Ridge Parkway. Situated on a corner lot, the property offers excellent curb appeal. A thoughtfully landscaped yard with horticulturist selected plantings that provide year round interest. The spacious, fully fenced yard is perfect for dogs, gardening, or simply enjoying a private outdoor retreat. Inside this cozy 2 bedroom, you’ll find light-filled living spaces and a functional layout that is move in ready, while still offering the opportunity for a new owner to add updates and make it their own over time. An unfinished basement provides excellent potential for expansion, storage, or a workshop. Whether you're searching for a primary residence or investment, this property offers both immediate livability and future potential in a convenient location.

34 Oakley Road, Asheville

Listing courtesy of Looking Glass Realty AVL LLC. jesse@lookingglassrealty.com

Sold listing courtesy of Looking Glass Realty AVL LLC
16 Main Street, Asheville
$340,000
3 Beds ⋅ 1 Baths ⋅ 4399925 MLS ⋅ CLOSED 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

Sold listing courtesy of Mosaic Community Lifestyle Realty
130 Winston Avenue, Asheville
$315,000
2 Beds ⋅ 1 Baths ⋅ 4385170 MLS ⋅ CLOSED 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

Sold listing courtesy of BHGRE Integrity Partners

“ 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”

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