1982 Maryland Ave
Winston-SalemNC27101
Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (39 Rentals)
Search the lowest-cost Apartments available for rent right now in the Skyland area of Winston-Salem.
1231 Gholson Ave S East
Winston-SalemNC27107
200 High St
Winston-SalemNC27101
1137 N Cameron Ave
Winston-SalemNC27101
1439 Clark Ave
Winston-SalemNC27105
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$825
Total Monthly Price
2 Bedroom Apartment Available NowTotal Monthly Price
Base Rent
$825
Total Monthly Price
$825
1225 New Hope Ln, Unit D, Unit D
1225 New Hope LnWinston-Salem, NC 27105
2001 S Main St
Winston-SalemNC27127
1514 Gholson Ave S East
Winston-SalemNC27107
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$850 - $1,0501 to 2 Bedroom Apartments Available Now
Kensington Village
479 Louise Wilson LnWinston-Salem, NC 27101
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Learn the official definition (spending 30% or more of your gross income on housing) and how to calculate your exact rent-to-income ratio. This guide offers expert tips on factoring in total housing costs (including utilities and fees) and budgeting accurately to avoid unnecessary financial strain.
1396 Chestnut Plains Ct
Winston-SalemNC27105
115 S Spruce St
Winston-SalemNC27101
1710 Lomond St
Winston-SalemNC27127
2721 Ivy Ave
Winston-SalemNC27105
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Rent Specials
$9502 Bedroom Apartments Available Now
Fairfield Apartments
2090 Cole RdWinston-Salem, NC 27107
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Rent Specials
$9902 Bedroom Apartments Available Now
2425-2445 Old Greensboro Rd
2425-2445 Old Greensboro RdWinston-Salem, NC 27101
630 Mulberry St SW
Winston-SalemNC27101
632 Mulberry St SW
Winston-SalemNC27101
2351 Felicity Cir
Winston-SalemNC27101
Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Thinking about getting a co-signer for your rental application? We break down what a co-signer is, the potential benefits, and the serious risks for both parties. Find out if it's the right choice for you.
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Rent Specials
$999 - $1,2992 to 3 Bedroom Apartments Available Now
Crestwood Gardens
2560 Ladeara Crest LnWinston-Salem, NC 27105
639 S Poplar St
Winston-SalemNC27101
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$1,020 - $1,0401 Bedroom Apartments Available Now
The Livery Apartments
648 Holly AveWinston-Salem, NC 27101
2230 Greenway Ave NW
Winston-SalemNC27105
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$1,069 - $1,470
Total Monthly Price
1 to 2 Bedroom Apartments Available NowTotal Monthly Price
Base Rent
$1,069 - $1,470
Total Monthly Price
Varies
Hilltop House
241 S Cherry StWinston-Salem, NC 27101
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$1,080 - $1,5701 to 2 Bedroom Apartments Available Now
Village Lofts Apartments
511 N Cherry StWinston-Salem, NC 27101
2240 Flag St
Winston-SalemNC27101
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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
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$1,0993 Bedroom Apartments Available Now
2560 La Deara Crest Ln, Unit 1808
2560 La Deara Crest LnWinston-Salem, NC 27105
Roommate Matching: Finding the Right Fit and Avoiding Pitfalls
When searching for a roommate, follow this list of essential steps and set clear expectations to create a solid foundation for a harmonious living situation.
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1 to 3 Bedroom Apartments
The Villas at Park Terrace
301 Walkertown AveWinston-Salem, NC 27105
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1 to 2 Bedroom Apartments
Fairview Landing
1120 Burke Village LnWinston-Salem, NC 27105
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1 to 3 Bedroom Apartments
Colony Place Apartments
900 N Cleveland AveWinston-Salem, NC 27101
1505 Williamson St
Winston-SalemNC27107
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2 Bedroom Apartments
1350 N Chestnut St
1350 N Chestnut StWinston-Salem, NC 27105
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2 Bedroom Apartments
Skyline Village Apartments
1528 Bruce StWinston-Salem, NC 27107
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2 Bedroom Apartments
Salem View Apartments
2001 S Main StWinston-Salem, NC 27127
526 E 17th St
Winston-SalemNC27105
325 W Twenty-Third St
Winston-SalemNC27105
The Art of the Rental Viewing: What to look for during a property tour
Touring a rental? This guide helps you know exactly what to look for, from safety features to hidden flaws, so you can confidently sign your lease or keep searching.
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2 Bedroom Apartments
555 East Apartments
555 N Martin Luther King Jr DrWinston-Salem, NC 27101
510 Alexander St
Winston-SalemNC27127
114 N Jackson Ave
Winston-SalemNC27101
Showing Results 1-39, Page 1 of 1
Skyland, Winston-Salem, NC Local Guide
How much does it cost to rent an apartment in Skyland?
| Bedroom | Average Rent | Cheapest Rent | Highest Rent |
|---|---|---|---|
| Skyland Studio Apartments | $1,362 | $1,175 | $1,549 |
| Skyland 1 Bedroom Apartments | $1,473 | $795 | $2,055 |
| Skyland 2 Bedroom Apartments | $1,765 | $695 | $3,514 |
| Skyland 3 Bedroom Apartments | $1,970 | $1,099 | $3,597 |
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Browse Apartments in this Neighborhood
There are currently 39 rentals with your search options within a 2 mile radius of the Skyland Neighborhood of Winston-Salem, NC.
See all Apartments in Winston-SalemExplore Winston-Salem
Skyland, Winston-Salem, NC Local Guide
- Nearby Winston-Salem neighborhoods
- Nearby Cities
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- Local Counties
- School Districts
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 Kensington Village priced from $850. Fairfield Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $950. Here are the most affordable Skyland apartments for rent in Winston-Salem, NC:
| Apartment Listing | Model Name | Bed/Bath | Priced From |
|---|---|---|---|
| Kensington Village | The Saville | 1BR,1BA | $850 |
| Fairfield Apartments | 2BR / 1BA | 2BR,1BA | $950 |
| 2425-2445 Old Greensboro Rd | 2 Bedroom | 2BR,1BA | $990 |
| The Livery Apartments | 1 Bed | 1BR,1BA | $1,020 |
| Hilltop House | A3 | 1BR,1BA | $1,069 |
| Village Lofts Apartments | 1BR/1.0BA | 1BR,1BA | $1,080 |
| Crestwood Gardens | 3 Bed/ 1 Bath | 3BR,1BA | $1,099 |
| Skyview Townhomes | 2 Bedroom | 2BR,1BA | $1,200 |
| Brown School Lofts at Legacy Heights | 1 Bedroom Garden | 1BR,1BA | $1,275 |
Best Value Apartments for Rent in Skyland, NC
As of April 17, 2026 the best value apartment in the Skyland area is the $1.30 price per square foot 664 W 2nd St Model at 664 W 2nd St in the in the South Central Winston Salem neighborhood starting from $1,295. The second greatest value Skyland apartment is the Kahlo Model at Gallery Lofts starting at $1,500 with a $1.53 price per square foot in the Downtown 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. |
|---|---|---|---|
| 664 W 2nd St | 664 W 2nd St | 2BR,1BA | $1.30 |
| Gallery Lofts | Kahlo | 1BR,1BA | $1.53 |
| 2425-2445 Old Greensboro Rd | 2 Bedroom | 2BR,1BA | $1.10 |
| Village Lofts Apartments | 2BR/2.0BA | 2BR,2BA | $1.89 |
| Crestwood Gardens | Cottage 3 Bed / 1 Bath | 3BR,1BA | $1.62 |
| 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 |
| The Livery Apartments | 1 Bed | 1BR,1BA | $1.89 |
| Kensington Village | The Saville | 1BR,1BA | $1.60 |
10 Hidden Costs of Renting You Should Budget for Before Signing a Lease
Avoid financial stress when renting. Learn about the 10 most common hidden costs—from pet fees to utilities—you must budget for before you sign a lease.
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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.
Read ArticleThe Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Moving is tough, especially long-distance. Learn how to minimize stress & expenses with proven strategies from a real estate pro, covering everything from logistics to finances.
Read ArticleCash or credit? Understanding the Importance of Credit Score in Real Estate and Renting
Discover how your credit score impacts your ability to lease or buy a home. Learn how credit scores are determined, how to check yours, and strategies to improve it for real estate success.
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How much rent can you afford?
The common "Rule of Thumb" is that rent should be no more than 30% of your income. How much is that? Enter your monthly income and click "Calculate My Budget" to find out.
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Pet Friendly LifestyleSkyland, Winston-Salem, NC
Ranked #81
Among cities in North Carolina for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.0Pet 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 (409)
7 out of 10
School data provided by Great Schools
Frequently Asked Questions about Cheap Skyland Apartments
What is the price of a cheap apartment in Skyland?
The cheapest apartment in Skyland is Kensington Village which is listed at $850, while the average apartment in Skyland costs $1,885.
What types of apartments are the cheapest in Skyland?
Student, low-income, and by-the-bed apartments are typically the cheapest rentals in most cities, though they require qualifying criteria to rent. There are 37 regular apartments in Skyland that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.
How do the prices of cheap apartments compare to the average apartment in Skyland?
Cheap apartments in Skyland have an average cost of $693 which is $1,192 cheaper than the average rent for all rentals in Skyland.
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
What Does “Rent Burdened” Mean? How Much Rent Is Too Much
Written by: Lauren Harrington
This article draws from first-hand renter experiences and recurring financial challenges reported after moving in.
Maximizing Your Refund: Essential Tax Tips for Renters
Written by: Christine Leonard, Esq.
Other than tax professionals, I can’t think of anyone who looks forward to tax season. For everybody else, April is a stressful month to collect information and meet deadlines.
18 Must-Ask Rental Tour Questions That Reveal the Truth about a Property
Written by: Lauren Harrington
Renting your next home can feel thrilling and overwhelming at the same time.
A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment
Written by: Bob Mallory
Packing up everything you own to move is so stressful for many that ending your apartment lease can feel like a small or unimportant task. Ending your lease involves more than simply turning over your keys on the last day.