Red Door Company

Homes for Sale in Chesterfield Winston-Salem NC

Browse 57 homes for sale in Chesterfield neighborhood of Winston-Salem, North Carolina.

Exterior photo of 309 Cheltenham Drive, Winston-Salem NC 27103. MLS: 1216231

309 Cheltenham DriveWinston-Salem, NC 27103

3 Bed
2 Bath
1,399 SQFT

Exterior photo of 245 Christine Court, Winston-Salem NC 27127. MLS: 1196533

245 Christine CourtWinston-Salem, NC 27127

3 Bed
4 Bath
3,338 SQFT

Exterior photo of 120 Tara Gail Lane, Winston-Salem NC 27127. MLS: 1150638

120 Tara Gail LaneWinston-Salem, NC 27127

3 Bed
2 Bath
1,900 SQFT

Exterior photo of 155 Tara Gail Lane, Winston-Salem NC 27127. MLS: 1076412

155 Tara Gail LaneWinston-Salem, NC 27127

4 Bed
3 Bath
2,350 SQFT

4516 Old Larkin Court_01

4516 Old Larkin CourtWake Forest, NC 27587

4 Bed
3 Bath
3,041 SQFT

Exterior photo of 313 Cheltenham Drive, Winston-Salem NC 27103. MLS: 1182149

313 Cheltenham DriveWinston-Salem, NC 27103

3 Bed
2 Bath
1,619 SQFT

Exterior photo of 389 Christine Court, Winston-Salem NC 27127. MLS: 1196934

389 Christine CourtWinston-Salem, NC 27127

3 Bed
3 Bath
2,169 SQFT

Exterior photo of 191 Christine Court, Winston-Salem NC 27127. MLS: 1150612

191 Christine CourtWinston-Salem, NC 27127

3 Bed
3 Bath
2,431 SQFT

Exterior photo of 360 Christine Court, Winston-Salem NC 27127. MLS: 1069236

360 Christine CourtWinston-Salem, NC 27127

3 Bed
3 Bath
2,338 SQFT

Exterior photo of 283 Sara Lane, Winston-Salem NC 27103. MLS: 1129320

283 Sara LaneWinston-Salem, NC 27103

3 Bed
2 Bath
1,665 SQFT

Exterior photo of 758 N Payne Road, Winston-Salem NC 27127. MLS: 1011126

758 N Payne RoadWinston-Salem, NC 27127

3 Bed
2 Bath
1,623 SQFT

Living Area

202 Chesterfield DriveWashington, NC 27889

3 Bed
1 Bath
1,010 SQFT

Exterior photo of 280 Christine Court, Winston-Salem NC 27127. MLS: 774377

280 Christine CourtWinston-Salem, NC 27127

3 Bed
3 Bath
1,995 SQFT

Exterior photo of 1985 Hickory Tree Road, Winston-Salem NC 27127. MLS: 1157396

1985 Hickory Tree RoadWinston-Salem, NC 27127

3 Bed
2 Bath
1,790 SQFT

Exterior photo of 184 Cale Bradley Court, Winston-Salem NC 27127. MLS: 1195530

184 Cale Bradley CourtWinston-Salem, NC 27127

3 Bed
2 Bath
1,692 SQFT

Visualization is a key part of your home buying experience. As you are looking at these pictures, take a minute to see yourself there. in each photo, moving from room to room. See and feel how it will be living here in this home. Here you are looking at the front right side of the home where you see the paved driveway and turnaround, the nice grass, the landscaping and how about that front porch.

1945 Hickory Tree RoadWinston-Salem, NC 27127

3 Bed
3 Bath
2,070 SQFT

Front

188 Tara Gail LaneMidway, NC 27127

2 Bed
2 Bath
1,961 SQFT

Downtown 4BR, 2BA Craftsman Bungalow With Large Welcoming Rocking Chair Porch! Walking Distance to Downtown Attractions, Restaurants, Short Drive to I-40.

712 Laurel StreetWinston-Salem, NC 27101

4 Bed
2 Bath
1,566 SQFT

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Frequently Asked Questions

How many homes are for sale in Chesterfield NC?: There are 1 homes in Chesterfield neighborhood, North Carolina for sale. The newest listing for sale has 3+ bedrooms, 2+ bathrooms, .25 acres, and pet friendly for $295,500 at 309 Cheltenham Drive.
What is the average price per square foot for homes in Chesterfield NC?: $211.22 is the average price per square foot for homes Chesterfield neighborhood, North Carolina. This is an increase compared to the $188 average a year prior in March 2025. Currently, a 0 SQFT House at 309 Cheltenham Drive in Chesterfield neighborhood, North Carolina has the lowest price per square foot at $211.22, while a 0 SQFT House at 309 Cheltenham Drive in Chesterfield neighborhood, North Carolina has the highest at $211.22.
What is the median list price for homes for sale in Chesterfield NC?: $295,500 is the median list price for homes for sale in Chesterfield neighborhood, North Carolina. This is an increase compared to the $270,000 median sale price a year prior in March 2025.
What is the average days on market for homes for sale in Chesterfield NC?: Most recently, a 3+ bedrooms, 2+ bathrooms, .25 acres, and pet friendly House at 309 Cheltenham Drive in Chesterfield neighborhood, North Carolina has been on the market for 1 day, while 309 Cheltenham Drive in Chesterfield neighborhood, North Carolina with 3+ bedrooms, 2+ bathrooms, .25 acres, and pet friendly has been on the market for 0 days.

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