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Homes for Sale in Cheslyn Winston-Salem NC

Browse 64 homes for sale in Cheslyn neighborhood of Winston-Salem, North Carolina.

Exterior photo of 4530 Deighton Court, Winston-Salem NC 27106. MLS: 1231428

4530 Deighton CourtWinston-Salem, NC 27106

3 Bed
3 Bath
3,226 SQFT

Exterior photo of 2589 Leighswood Drive, Winston-Salem NC 27106. MLS: 1122874

2589 Leighswood DriveWinston-Salem, NC 27106

4 Bed
3 Bath
2,332 SQFT

Exterior photo of 2583 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1194082

2583 Crosland Hill DriveWinston-Salem, NC 27106

3 Bed
3 Bath
2,018 SQFT

Exterior photo of 2643 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1037083

2643 Crosland Hill DriveWinston-Salem, NC 27106

5 Bed
3 Bath
2,696 SQFT

Exterior photo of 4538 Deighton Court, Winston-Salem NC 27106. MLS: 1174582

4538 Deighton CourtWinston-Salem, NC 27106

3 Bed
3 Bath
2,051 SQFT

Your Dream Home

2635 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
4 Bath
3,118 SQFT

Exterior photo of 2631 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1218428

2631 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
4 Bath
3,156 SQFT

Exterior photo of 4539 Deighton Court, Winston-Salem NC 27106. MLS: 1028095

4539 Deighton CourtWinston-Salem, NC 27106

4 Bed
3 Bath
2,376 SQFT

Exterior photo of 2640 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1145970

2640 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
3 Bath
2,688 SQFT

Exterior photo of 2636 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1219011

2636 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
4 Bath
3,105 SQFT

Exterior photo of 2635 Leighswood Drive, Winston-Salem NC 27106. MLS: 1182096

2635 Leighswood DriveWinston-Salem, NC 27106

3 Bed
3 Bath
3,222 SQFT

Exterior photo of 2626 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1098949

2626 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
4 Bath
3,105 SQFT

Exterior photo of 2611 Leighswood Drive, Winston-Salem NC 27106. MLS: 1041822

2611 Leighswood DriveWinston-Salem, NC 27106

4 Bed
3 Bath
2,202 SQFT

Exterior photo of 2568 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1162156

2568 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
3 Bath
3,072 SQFT

Exterior photo of 2632 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1140076

2632 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
3 Bath
2,889 SQFT

Exterior

2610 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
3 Bath
3,069 SQFT

Exterior photo of 2627 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1113701

2627 Crosland Hill DriveWinston-Salem, NC 27106

3 Bed
3 Bath
2,238 SQFT

Exterior photo of 2611 Crosland Hill Drive, Winston-Salem NC 27106. MLS: 1139731

2611 Crosland Hill DriveWinston-Salem, NC 27106

4 Bed
3 Bath
2,428 SQFT

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Frequently Asked Questions

How is the for sale real estate market for homes in Cheslyn NC?: In August of 2026, the median sale price for Cheslyn neighborhood, North Carolina homes for sale is $445,000. On average, they sold within 77 days. There were 1 homes for sale in August 2026.
How many homes are for sale in Cheslyn NC?: There are 1 homes in Cheslyn neighborhood, North Carolina for sale. Last month, there were 1 listing, and 1 a year prior in August 2025. The newest listing for sale has 3+ bedrooms, 3+ bathrooms, .22 acres, and pet friendly for $379,900 at 4530 Deighton Court.
What is the average price per square foot for homes in Cheslyn NC?: $117.76 is the average price per square foot for homes Cheslyn neighborhood, North Carolina. This is a decrease compared to the $143.32 average price per square foot last month, August 2026. Currently, a 0 SQFT House at 4530 Deighton Court in Cheslyn neighborhood, North Carolina has the lowest price per square foot at $117.76, while a 0 SQFT House at 4530 Deighton Court in Cheslyn neighborhood, North Carolina has the highest at $117.76.
What is the median list price for homes for sale in Cheslyn NC?: $379,900 is the median list price for homes for sale in Cheslyn neighborhood, North Carolina. This is a decrease compared to the $445,000 median sale price last month, August 2026.
What is the average days on market for homes for sale in Cheslyn NC?: 77 days on market is the August 2026 average for homes for sale in Cheslyn neighborhood, North Carolina. Most recently, a 3+ bedrooms, 3+ bathrooms, .22 acres, and pet friendly House at 4530 Deighton Court in Cheslyn neighborhood, North Carolina has been on the market for 13 days, while 4530 Deighton Court in Cheslyn neighborhood, North Carolina with 3+ bedrooms, 3+ bathrooms, .22 acres, and pet friendly has been on the market for 13 days.

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