INNOVATE Real Estate
Stick/Site Built at 288 Hillside Court, Winston-Salem NC 27107
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$425,000

288 Hillside Court, Winston-Salem NC 27107
Winston-Salem, NC 27107
Listed by Kim Kennedy
Bedrooms
3
Bathrooms
3
Living area
2,142 sqft
Year built
1977

About this home

Privacy, acreage, low taxes, no HOA, all brick home on a full basement in the Midway and Oak Grove school district of Davidson County. Property has 5.98 +/- acres. Home situated in a cul-de-sac at the back of a quiet neighborhood. The lot is mostly wooded with a winding paved driveway leading to the house. House is surrounded by woods, but has a spacious yard to enjoy the outdoors in privacy. Main level has 3 bedrooms, 2 baths, open vaulted living room has fireplace with wood stove, formal dining, kitchen and laundry. Basement partially finished with 2 additional rooms with closet and window and a den with wood burning fireplace. There is a 2 car basement garage and double carport on the main level. Relax on the covered front porch or sit in the sun on the open back deck. This is a one owner home. Roof replaced in 2025, new heat pump in 2023, water heater 2021. Basement had new sump pump installed in 2021. Finished areas of basement were unpermitted. Septic is for a 3 bedroom home.

Property details

MLS
Triad MLS
MLS #
1229706
Property type
Stick/Site Built
Subdivision
Brentwood Forest
Status
Active
Days on market
66
On market date
July 31, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
4
Parking spaces
N/A
Lot size
5.98 acres

Location

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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
Friendship Elementary
0.82 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
488
Student:teacher ratio
16.3:1
District
Davidson County Schools
Middle
Oak Grove Middle
1.27 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: C (2025)
Enrollment
725
Student:teacher ratio
16.5:1
District
Davidson County Schools
High
Oak Grove High
1.04 mi away · Grades 9-12
Nearest school -- attendance-zone data not available here
3.7
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: B (2025)
Enrollment
895
Student:teacher ratio
16.6:1
District
Davidson 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). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

14
Very car-dependent
out of 100
EPA National Walkability Index
2.8 / 20 -- Least walkable

Market position

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

On the market 66 days -- 21 fewer days than Winston-Salem's current average of 87 days.
For reference, the median list price across 1,619 active listings in Winston-Salem right now is $275,000.

Mortgage calculator

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Est. monthly payment
$2,709/mo
$85,000 down
$340,000 loan
Principal & interest$2,205
Property tax (est.)$354
Home insurance (est.)$150

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Data source: Listing information provided by Triad MLS via Trestle/CoreLogic. Last updated 28 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.