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Homes for Sale in Chesterfield Winston-Salem NC

Browse 58 homes for sale in Chesterfield neighborhood of Winston-Salem, North Carolina.

Exterior photo of 300 Christine Court, Winston-Salem NC 27127. MLS: 1204789

300 Christine CourtWinston-Salem, NC 27127

2 Bed
2 Bath
1,336 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

Exterior Front

245 Christine CourtWinston Salem, NC 27127

3 Bed
4 Bath
3,401 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

202 Chesterfield Drive

202 Chesterfield DriveWashington, NC 27889

3 Bed
1 Bath
1,010 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

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 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 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

Exterior photo of 191 Christine Court, Winston Salem NC 27127. MLS: 781968

191 Christine CourtWinston Salem, NC 27127

3 Bed
3 Bath
2,428 SQFT

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Frequently Asked Questions

How is the for sale real estate market for homes in Chesterfield NC?: In November of 2025, prices for Chesterfield neighborhood, North Carolina homes for sale were down 3.6% compared to the previous year. The median sale price was $294,000; on average, they sold within 31 days compared to 25 days on market the previous year. There were 1 homes for sale in November 2025, a decrease from 1 during the same month in the previous year.
How many homes are for sale in Chesterfield NC?: There are 1 homes in Chesterfield neighborhood, North Carolina for sale. Last year in November, there were listing. The newest listing for sale has 2+ bedrooms, 2+ bathrooms, 1,336 SQFT, .46 acres, and pet friendly for $275,000 at 300 Christine Court.
Are prices rising or falling for homes in Chesterfield NC?: Compared to the previous month, prices are falling for homes in Chesterfield neighborhood, North Carolina. The median sale price was $294,000 in November 2025, which is lower than a month previous at $380,000. The median sale price fell 3.6% compared to the $305,000 median sale price a year ago in November 2024.
What is the average price per square foot for homes in Chesterfield NC?: $205.84 is the average price per square foot for homes Chesterfield neighborhood, North Carolina. This is an increase compared to the $173.76 average price per square foot last month, November 2025, and an increase compared to the $170 average a year prior in November 2024. Currently, a 1,336 SQFT house at 300 Christine Court in Chesterfield neighborhood, North Carolina has the lowest price per square foot at $205.84, while a 1,336 SQFT house at 300 Christine Court in Chesterfield neighborhood, North Carolina has the highest at $205.84.
What is the median list price for homes for sale in Chesterfield NC?: $275,000 is the median list price for homes for sale in Chesterfield neighborhood, North Carolina. This is a decrease compared to the $294,000 median sale price last month, November 2025, and a decrease compared to the $305,000 median sale price a year prior in November 2024.
What is the average days on market for homes for sale in Chesterfield NC?: 31 days on market is the November 2025 average for homes for sale in Chesterfield neighborhood, North Carolina. This represents an increase from the previous month's average of 13 days on market, and an increase from the same month the year prior of 25 days on market average. Most recently, a 2+ bedrooms, 2+ bathrooms, 1,336 SQFT, .46 acres, and pet friendly house at 300 Christine Court in Chesterfield neighborhood, North Carolina has been on the market for 1 day, while 300 Christine Court in Chesterfield neighborhood, North Carolina with 2+ bedrooms, 2+ bathrooms, 1,336 SQFT, .46 acres, and pet friendly has been on the market for 0 days.

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