Stick/Site Built at 2299 Winterberry Drive, Winston-Salem NC 27106
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$315,000

2299 Winterberry Drive, Winston-Salem NC 27106
Winston-Salem, NC 27106
Listed by Brandon LaVallee
Bedrooms
3
Bathrooms
3
Living area
1,839 sqft
Year built
1984

About this home

This renovated ranch checks every box. A dramatic shiplap fireplace wall rises to soaring vaulted ceilings in the great room, anchoring an open floor plan that flows seamlessly into the updated kitchen and dining area. With shaker cabinets, stainless appliances, updated countertops, and subway tile backsplash make the kitchen as functional as it is sharp. Updated LVP flooring runs throughout the main level. Three bedrooms, three full baths — including a spacious main-level primary suite and a private upstairs loft suite, each with their own bath. Main level laundry and garage keep daily life simple. Out back, a large deck and level yard with plenty of room to play. That covered front porch and iconic weeping willow welcome you home. Zoned for Reagan High School and minutes from Meadowlark and Robinhood Road.

Property details

MLS
Triad MLS
MLS #
1235009
Property type
Stick/Site Built
Subdivision
Winterberry
Status
Active
Days on market
26
On market date
September 16, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
1
Parking spaces
N/A
Lot size
0.5 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card.

Elementary
Vienna Elementary
1.23 mi away · Grades -1-5
Zoned school (attendance boundary, 2015-16 data)
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
745
Student:teacher ratio
15.5:1
District
Winston Salem / Forsyth County Schools
Middle
Thomas Jefferson Middle
2.96 mi away · Grades 6-8
Zoned school (attendance boundary, 2015-16 data)
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
792
Student:teacher ratio
16.9:1
District
Winston Salem / Forsyth County Schools
High
Early College of Forsyth Co
6.94 mi away · Grades 9-12
Zoned school (attendance boundary, 2015-16 data)
3.8
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: A (2025)
Enrollment
260
Student:teacher ratio
28.9:1
District
Winston Salem / Forsyth County Schools

Walkability

Blended score for Winston-Salem's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

26
Car-dependent
out of 100
EPA National Walkability Index
7.2 / 20 -- Below average walkable
Google Places amenity density
10 / 100
Restaurants & cafes0
Grocery stores1
Parks0
Schools1
Transit stops0
Pharmacies0

Market position

How this listing compares to current activity in Winston-Salem, from live MLS data.

On the market 26 days -- 60 fewer days than Winston-Salem's current average of 86 days.
For reference, the median list price across 1,634 active listings in Winston-Salem right now is $274,900.

Mortgage calculator

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Est. monthly payment
$2,047/mo
$63,000 down
$252,000 loan
Principal & interest$1,634
Property tax (est.)$263
Home insurance (est.)$150

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Data source: Listing information provided by Triad MLS via Trestle/CoreLogic. Last updated 27 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.