Single Family Residence at 5550 Overlook Circle, Winston Salem
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 2 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 3 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 4 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 5 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 6 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 7 of 48
Living Room - 5550 Overlook Circle, Winston Salem
Living Room - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Dining Room - 5550 Overlook Circle, Winston Salem
Dining Room - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Dining/Living Rooms - 5550 Overlook Circle, Winston Salem
Living/Dining/Kitchen - 5550 Overlook Circle, Winston Salem
Kitchen - 5550 Overlook Circle, Winston Salem
Kitchen - 5550 Overlook Circle, Winston Salem
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 18 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 19 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 20 of 48
Great Room - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Great Room - 5550 Overlook Circle, Winston Salem
Primary Broom (main level) - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Primary Bedroom - 5550 Overlook Circle, Winston Salem
En-Suite Bathroom - 5550 Overlook Circle, Winston Salem
2nd Bedroom (main level) - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
2nd Bedroom - 5550 Overlook Circle, Winston Salem
Hall Bathroom - 5550 Overlook Circle, Winston Salem
3rd Bedroom (main level) - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
3rd bedroom - 5550 Overlook Circle, Winston Salem
Recreation Room - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Recreation Room - 5550 Overlook Circle, Winston Salem
Recreation Room - 5550 Overlook Circle, Winston Salem
Bathroom (Basement) - 5550 Overlook Circle, Winston Salem
4th Bedroom (Basement) - 5550 Overlook Circle, Winston Salem
4th Bedroom - 5550 Overlook Circle, Winston Salem
Virtually Staged - 5550 Overlook Circle, Winston Salem
Laundry (basement) - 5550 Overlook Circle, Winston Salem
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 44 of 48
2-Car Garage - 5550 Overlook Circle, Winston Salem
New Deck! - 5550 Overlook Circle, Winston Salem
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 47 of 48
Single Family Residence at 5550 Overlook Circle, Winston Salem, photo 48 of 48
48 photos

$398,900

5550 Overlook Circle
Winston Salem, NC 27105
Listed by Jordan Hairston · Real Broker, LLC
Bedrooms
4
Bathrooms
3
Living area
3,183 sqft
Year built
1967

About this home

Beautifully renovated brick ranch on .88 acres in a cul-de-sac in Pine Brook Country Club! This spacious home features generously sized rooms and an open living, dining, and kitchen layout. The updated kitchen offers a gas cooktop, quartz countertops, pullout drawers, stainless steel appliances, and a tile backsplash. The great room boasts cathedral ceilings, a brick fireplace, and access to a huge deck perfect for entertaining. Three spacious bedrooms are on the main level, including a primary suite with an ensuite bath featuring separate standard and makeup vanities. The main level also includes the laundry room. The lower level offers a huge recreation room with a brick fireplace, a refreshment area with cabinetry and a sink, a full bath, an additional bedroom, and an oversized utility room. An oversized 2-car basement garage and plenty of parking complete this impressive home!

Highlights

Fireplace

Property details

MLS
Canopy MLS
MLS #
CAR4432343
Property type
Single Family Residence
Subdivision
Pine Brook
Status
Active
Days on market
4
On market date
October 9, 2026
Stories
N/A
Total bathrooms
3
Garage spaces
2
Parking spaces
N/A
Lot size
N/A
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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
Mineral Springs Elementary
1.87 mi away · Grades -1-5
Zoned school (attendance boundary, 2015-16 data)
2.6
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: D (2025)
Enrollment
551
Student:teacher ratio
13.8:1
District
Winston Salem / Forsyth County Schools
Middle
Mineral Springs Middle
1.94 mi away · Grades 6-8
Zoned school (attendance boundary, 2015-16 data)
1.6
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: F (2025)
Enrollment
709
Student:teacher ratio
17.3:1
District
Winston Salem / Forsyth County Schools
High
Carver High
4.06 mi away · Grades 9-12
Zoned school (attendance boundary, 2015-16 data)
2.9
Local Score (state rating (2025) blended 70/30 with student-teacher ratio) -- not an official state rating
State rating: D (2025)
Enrollment
605
Student:teacher ratio
11.9:1
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). EPA National Walkability Index only -- nearby-amenity data not cached yet for this area.

18
Very car-dependent
out of 100
EPA National Walkability Index
3.7 / 20 -- Least walkable

Market position

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

On the market 4 days -- 83 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

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

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Est. monthly payment
$2,552/mo
$79,780 down
$319,120 loan
Principal & interest$2,070
Property tax (est.)$332
Home insurance (est.)$150

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Data source: Listing information provided by Canopy MLS (carolina) via Trestle/CoreLogic. Last updated 4 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.