UNDER CONTRACT

Contingent

$525,000

Est. $3,223/mo —

•

1,778

sq ft

29 Winding Rd, Asheville, NC 28803

About this home

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!

Single-familyProperty Type

2007Year Built

0.26 acresLot Size

$295Price/Sq.Ft.

1 car garageParking

Listed by Chris Smith • Century 21 Connected

Contact: brokerchrissmith@gmail.com

Listing updated: Aug 9, 2026 at 01:20pm

Redfin checked: a few seconds ago

•Source:CANOPYMLS as Distributed by MLS Grid #4407595

Payment calculator

$3,223 per month

Principal and interest$2,865

Property taxes

$244

HOA dues

Home insurance

$114

Utilities

Add

5 minutes to get started. No credit impact.

Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

OPEN WED, 5PM TO 6:30PM3D WALKTHROUGH
$890,000
3 beds2.5 baths2,390 sq ft
101 Balsamwood Rd, Leicester, NC 28748
OPEN SAT, 12PM TO 2PM3D WALKTHROUGH
$598,000
3 beds2.5 baths2,047 sq ft
65 Beechwood Rd, Asheville, NC 28805
OPEN SAT, 2PM TO 4PM3D WALKTHROUGH
$765,000
2 beds2 baths1,648 sq ft
6 Starwood Valley Trl, Arden, NC 28704
OPEN SUN, 2AM TO 4PM
$995,000
2 beds2 baths2,808 sq ft
37 Ashe Park Cir, Asheville, NC 28806
OPEN SUN, 2PM TO 4PM
$470,000
2 beds2 baths1,751 sq ft
16 Cedarwood Dr, Asheville, NC 28803
OPEN SUN, 2PM TO 4PM
$375,000
3 beds2 baths1,456 sq ft
10 Enochs Way, Fletcher, NC 28732
OPEN SUN, 2PM TO 4PM3D WALKTHROUGH
$466,900
4 beds3 baths1,911 sq ft
57 N Sunberry Trl, Fletcher, NC 28732
OPEN SUN, 2PM TO 4PM
$435,000
2 beds2 baths1,447 sq ft
403 Kyfields Dr, Weaverville, NC 28787
OPEN SUN, 2PM TO 4PM
$1,150,000
3 beds3.5 baths4,135 sq ft
440 Sondley Woods Pl, Asheville, NC 28805
OPEN SUN, 2PM TO 4PM
$449,500
3 beds2 baths1,658 sq ft
13 Laurel Place Dr, Asheville, NC 28803

Around this home

Schools

K - 12
Preschool & daycare

Oakley Elementary

Public PreK-5 • Assigned • 1.0mi

3/10

A C Reynolds Middle

Public 6-8 • Assigned • 3.4mi

8/10

A C Reynolds High

Public PreK-12 • Assigned • 3.3mi

8/10

Provided by GreatSchools

About

Oakley

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

The average home goes pending in 69 days.

SALE-TO-LIST

Most homes are selling 3% below list price.

LIST PRICE

Median sale price in this area is $527,270. (0% higher than this home)

PRICE DROP

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

Sale and tax history for 29 Winding Rd

Sale History
Tax History

Date

Event

Price

CANOPYMLS as Distributed by MLS Grid #4407595

Aug 9, 2026

Contingent

—

Jul 31, 2026

Listed

$525,000

$295/sq ft

Jul 28, 2026

Coming Soon

$525,000

$295/sq ft

Public Records

Jul 1, 2022

Sold

$473,000

$266/sq ft

CANOPYMLS as Distributed by MLS Grid #3860092

Jul 1, 2022

Sold

$475,000

$267/sq ft

May 15, 2022

Contingent

—

May 12, 2022

Listed

$475,000

$267/sq ft

+32

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

Baths

2.5

Stories

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)

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.

SOLD MAY 4, 2026
$595,000 Last sold price
4 beds3.5 baths2,092 sq ft
117 Third St, Asheville, NC 28803
$11/sq ft
larger lot
18 years newer
SOLD JUN 8, 2026
$515,000 Last sold price
3 beds2.5 baths1,592 sq ft
37 First St, Asheville, NC 28803
$28/sq ft
19 years newer
no basement
SOLD JUL 27, 2026
$687,500 Last sold price
3 beds2.5 baths1,729 sq ft
71 Mclain St, Asheville, NC 28803
$103/sq ft
8 years newer
no basement
SOLD AUG 12, 2026
$395,000 Last sold price
3 beds2 baths1,415 sq ft
62 1st St, Asheville, NC 28803
$16/sq ft
smaller lot
43 years older
SOLD SEP 15, 2026
$500,000 Last sold price
3 beds1.5 baths1,725 sq ft
109 Forest Hill Dr, Asheville, NC 28803
$5/sq ft
80 years older
unfinished basement
SOLD APR 6, 2026
$342,000 Last sold price
3 beds2 baths1,667 sq ft
93 Wanoca Ave, Asheville, NC 28803
$90/sq ft
smaller lot
61 years older

Rental earnings

Est. $2,468 per month, based on comparable rentals

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New listings for sale in 28803

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Details provided by CANOPYMLS as Distributed by MLS Grid and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Market insights

Property details

Sale and tax history for 29 Winding Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 29 Winding Rd

This home may not be allowing tours right now

Nearby similar homes

New listings for sale in 28803

More real estate resources