1425 Gholson Ave
Winston-SalemNC27107
Cheap Homes for Rent in the Skyland Neighborhood of Winston-Salem, NC from $695 (21 Rentals)
Search the lowest-cost Homes available for rent right now in the Skyland area of Winston-Salem.
1401 Underwood Ave
Winston-SalemNC27105
301 N Spring St
Winston-SalemNC27101
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$8501 Bedroom Apartments Available Now
1514 E 14th St, Unit A
1514 E 14th StWinston-Salem, NC 27105
2931 Old Greensboro Rd
Winston-SalemNC27101
1520 Fitch St
Winston-SalemNC27107
2017 E 18th St
Winston-SalemNC27105
Rent According to Income: A Look at Income-Restricted Rentals
Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.
2305 Booker St
Winston-SalemNC27105
625 Glenbrook Dr
Winston-SalemNC27101
918 Franklin St SW
Winston-SalemNC27101
1416 E Twenty-Fourth St
Winston-SalemNC27105
1500 Montague St
Winston-SalemNC27107
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$9992 Bedroom Apartments Available Now
2560 Ladeara Crest Ln, Unit 2508-1
2560 Ladeara Crest LnWinston-Salem, NC 27105
1615 Argonne Blvd
Winston-SalemNC27107
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.
1608 Emerald St
Winston-SalemNC27105
1926 Kentucky Ave
Winston-SalemNC27101
409 Mason St NE
Winston-SalemNC27101
406 E 17th St
Winston-SalemNC27105
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$1,0993 Bedroom Apartments Available Now
2560 La Deara Crest Ln, Unit 1804
2560 La Deara Crest LnWinston-Salem, NC 27105
124 E 14th St
Winston-SalemNC27105
1602 E 23rd St
Winston-SalemNC27105
How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide
Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.
Showing Results 1-21, Page 1 of 1
Skyland, Winston-Salem, NC Local Guide
How much does it cost to rent a home in Skyland?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Skyland 2 Bedroom Homes for Rent | $1,267 | $895 | $2,200 |
| Skyland 3 Bedroom Homes for Rent | $1,540 | $995 | $3,800 |
| Skyland 4 Bedroom Homes for Rent | $1,516 | $1,350 | $1,700 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Homes for Rent in this Neighborhood
There are currently 21 rentals with your search options within a 2 mile radius of the Skyland Neighborhood of Winston-Salem, NC.
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Skyland, Winston-Salem, NC Local Guide
- Nearby Winston-Salem neighborhoods
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Cheapest Available Skyland Apartments for Rent
The cheapest available apartment rental in the Skyland area of Winston-Salem, NC is a 1 Bed unit found at 1350 N. Chestnut St. priced from $850. The Livery Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $875. Here are the most affordable Skyland apartments for rent in Winston-Salem, NC:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| 1350 N. Chestnut St. | 1BR/1.0BA | 1BR,1BA | $850 |
| The Livery Apartments | 1 Bed | 1BR,1BA | $875 |
| Kensington Village | The Saville | 1BR,1BA | $910 |
| Crestwood Gardens | 2 Bed/ 1 Bath | 2BR,1BA | $925 |
| Fairfield Apartments | 2BR / 1BA | 2BR,1BA | $950 |
Best Value Apartments for Rent in Skyland, NC
As of August 31, 2026 the best value apartment in the Skyland area is the $1.51 price per square foot Miro Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $2,120. The second greatest value Skyland apartment is the Two Bedroom One Bath Model at 664 2nd St NW starting at $1,095 with a $1.10 price per square foot in the South Central Winston Salem neighborhood. Here is today’s list of the best values for Skyland apartments based on price per square foot:
| Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
|---|---|---|---|
| Gallery Lofts | Miro | 2BR,2BA | $1.51 |
| 664 2nd St NW | Two Bedroom One Bath | 2BR,1BA | $1.10 |
| Village Lofts | 2BR/2.0BA | 2BR,2BA | $1.61 |
| 2425-2445 Old Greensboro Rd | 2 Bedroom | 2BR,1BA | $1.10 |
| 705 Alexander St, Unit 1 | 705 Alexander St | 2BR,1BA | $0.98 |
| 1225 New Hope Ln, Unit D | 1225 New Hope Ln | 2BR,1BA | $1.03 |
| Fairfield Apartments | 2BR / 1BA | 2BR,1BA | $1.22 |
| Gateway Apartments | 1.1 | 1BR,1BA | $1.68 |
| Crestwood Gardens | 2 Bed/ 1 Bath | 2BR,1BA | $1.22 |
| The Livery Apartments | 1 Bed | 1BR,1BA | $1.64 |
Don't Settle: How to Negotiate Your Apartment Lease and Save Money
Discover the insider tips from an attorney and real estate agent on how to negotiate your next apartment lease. Find out what's on the table and what's not, so you can save money and get the best terms possible.
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Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University
From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.
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Pet Friendly LifestyleSkyland, Winston-Salem, NC
Ranked #80
Among cities in North Carolina for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Best Local Schools in Skyland, Winston-Salem, NC
Ashley Elementary
Winston Salem & Forsyth County School District
Public School - Grades PK-5 (373)
2 out of 10
The Downtown School
Winston Salem & Forsyth County School District
Public School - Grades PK-8 (400)
7 out of 10
School data provided by Great Schools
Frequently Asked Questions about Skyland
What type of rentals are currently available in Skyland?
There are currently 123 Apartments for Rent in Skyland, NC with pricing that ranges from $675 to $3,775. There are also 53 Single Family Homes for rent, Condos, and Townhome rentals currently available in Skyland ranging from $695 to $3,800.
What is the current price range for Rental Homes in Skyland?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Skyland ranges from $695 to $3,800 with an average monthly rent of $1,377.
Expert Rental Resources
The rental experts at ApartmentHomeLiving.com provide you with top advice, tools, and tips for understanding the leasing process and finding the perfect rental. Here are a few helpful rental and leasing articles from our experts to guide you on your search.
Articles, How-To's, and Tips
Rent According to Income: A Look at Income-Restricted Rentals
Written by: Robin Stewart
The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.
Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags
Written by: Robin Stewart
Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.
First Apartment Regrets: Real Renters Share What They'd Do Differently
Written by: Robin Stewart
Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.
Renters Insurance 101: What It Is, What It Covers, and Why You Need It
Written by: Robin Stewart
Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.