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!
Oakley, located between Biltmore Village and East Asheville, is a residential and commercial Asheville neighborhood with a walkable main drag and a low-key, lived-in feel. The neighborhood’s character concentrates along Fairview Road near the Oakley Library, where corner markets, casual eateries, and everyday errands cluster in a compact strip. Local pillars include Highland Brewing Company’s meadow-side taproom, the Copper Crown, and the Blue Ridge Biscuit Company. Housing leans toward mid-century ranches and older cottages, with pockets of newer infill. Side streets roll gently toward the Swannanoa River corridor, adding a green edge to the grid. Daily life centers on patios, takeout counters, and short drives to trailheads and river parks.
Provided by Walk Score and Local Logic
Market insights
29 Winding Rd · $525,000
DAYS ON MARKET
53 days
The average home goes pending in 69 days.
SALE-TO-LIST
96.7%
Most homes are selling 3% below list price.
LIST PRICE
$525,000
Median sale price in this area is $527,270. (0% higher than this home)
PRICE DROP
0 price drops
26% of homes in this area have had a price drop in the past month.
Property details
Interior
Exterior
Finance
Kitchen
Bathroom
Bedroom
Living
Dining
Interior features
Breakfast bar
Pantry
Walk-in closets
Screen door(s)
Bedrooms
Three bedrooms (all on the upper level)
Bathrooms
Two full bathrooms
One half bathroom
Kitchen
Dishwasher
Disposal
Electric oven and range
Refrigerator
Laundry & utility
Laundry located in the basement
Electric water heater
Flooring
Carpet
Tile
Wood
Heating & cooling
Central heating and cooling
Electric heating
Heat pump
Exterior features
Covered patio/porch areas
Front porch
Rear porch
Deck
Fire pit
Fenced backyard
Home design
Single-family residence
Site-built construction
Two-level home
RS8 zoning
Parking
Attached garage (garage faces rear)
One garage space
Driveway
Basement access to parking
Construction
Hardboard siding
Basement foundation
Basement is finished with exterior entry and walk-out access; includes storage space
Utilities
City water
Public sewer
Electricity connected
HOA & community
No HOA dues
Other
Property located on a cul-de-sac with sloped lot and green area
Publicly maintained paved asphalt road
Electricity and solar
View estimated energy costs and solar savings for this home
Lovely home situated in the heart of town on a private cul-de-sac. Large lot with off street parking and a one car garage. Lots of natural light throughout. Primary suite with walk-in closet and en-suite bathroom. Bright kitchen with pantry, breakfast bar and dining area opens to the deck perfect for grilling. Lower level flex space ideal for home office, recreation, or exercise room. Great backyard with plenty of green space ideal for play or gardening. Walkable to all things Biltmore Village and minutes from downtown Asheville, Mission Hospital and all of Asheville's outdoor perks. Don't miss this one.
CANOPYMLS as Distributed by MLS Grid #3381222
Jun 7, 2018
Sold
$315,000
$177/sq ft
Jun 6, 2018
Pending
—
Apr 24, 2018
Contingent
—
Apr 16, 2018
Listed
$327,500
$184/sq ft
+25
Hold up! Are you seeing this? This freshly painted, light and bright home with new carpet is ready to move in and is just minutes away from Biltmore Village and downtown Asheville. 29 Winding Road has Oak hardwoods throughout the main, hallways and stairs and offers an attractive stacked stone fireplace in the family room. The kitchen has dining area plus a breakfast bar and offers a back deck for grilling. Upstairs you will find 3 nice sized bedrooms with the master bath having tile floors, oversized vanity and garden tub. Downstairs has a bonus room and multiple closets for storage. This home sits on a fantastic lot with private backyard escape and fire pit off a culdesac street. Come see what 29 Winding Road has to offer you and schedule your tour today.
CANOPYMLS as Distributed by MLS Grid #NCM574760
Jan 23, 2015
Sold
$235,000
$132/sq ft
Jan 23, 2015
Sold
$235,000
$132/sq ft
Jan 11, 2015
Delisted
—
Dec 9, 2014
Listed
$239,000
$134/sq ft
Public Records
Dec 4, 2006
Sold
$100,000
$56/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$2,925 (+6.6%)
$72,100 + $223,800
$295,900
2024
$2,743 (+2.9%)
$72,100 + $223,800
$295,900
2023
$2,666 (+1.1%)
$72,100 + $223,800
$295,900
2022
$2,636
$72,100 + $223,800
$295,900
2021
$2,636 (+17.5%)
$72,100 + $223,800
$295,900
2020
$2,244
$72,100 + $223,800
$295,900
2019
$2,244
$51,600 + $182,700
$234,300
2018
$2,244 (−1.0%)
$51,600 + $182,700
$234,300
2017
$2,268 (+9.7%)
$51,600 + $182,700
$234,300
2016
$2,067
$51,600 + $182,700
$234,300
2015
$2,067 (+1.4%)
$26,200 + $165,400
$191,600
2014
$2,038
$26,200 + $165,400
$191,600
Public record
Public record
Zoning
Beds
2
Baths
2.5
Stories
2
Lot width
—
Lot depth
—
Lot size
0.26 Acres
Year renovated
2007
Finished Sq. Ft.
1,740
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,740
Year built
2007
Style
Single Family Residential
County
Buncombe County
APN
965801823600000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Aug 10, 2026.
RS8
RESOURCE MANAGEMENT OVERLAY
Residential Single-Family High Density District
It is the intent of the RS-8 Residential Single-Family High Density District to establish a high density per acre for single-family dwellings where public infrastructure is sufficient to support such development and to stabilize and protect the district's residential character in areas of existing high density single-family development while promoting a suitable environment for single-family living. Non-single-family development normally required to provide the basic elements of a balanced and attractive residential area is also permitted.
Zone overlays
Resource Management Overlay
Permitted uses
Include but are not limited to:
Community / recreation center
Housing-Single unit
Fire house
Library
Police station
Golf related
Communications tower
Cemetery
Park & open space
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
4/10 Heat Factor
7 days above 98° expected this year, 19 days in 30 years
2/10 Wind Factor
Minor risk of severe winds over next 30 years
3/10 Air Factor
3 unhealthy days expected this year, 4 days in 30 years
Provided by First Street
Historical weather
Asheville, NC • 28803
Average low and high temperatures (°F)
44
26
54
33
66
41
73
50
73
55
82
63
86
67
78
63
75
59
69
48
60
42
50
32
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
93/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 14% for direct sun exposure in Asheville. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.9 hrs
5.3 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 29 Winding Rd
$520,614
$4,386 under list price of $525K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $342K to $688K.