Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (37 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Skyland area of Winston-Salem.

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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property at 2351 Felicity Cir

2351 Felicity Cir

Winston-SalemNC27101

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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Cash 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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Fairview Landing
1 to 2 Bedroom Apartments

Fairview Landing

1120 Burke Village LnWinston-Salem, NC 27105
  • Utilities Included
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Colony Place Apartments
1 to 3 Bedroom Apartments

Colony Place Apartments

900 N Cleveland AveWinston-Salem, NC 27101
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Aster Park Apartments
1 to 4 Bedroom Apartments

Aster Park Apartments

1620 Hope LnWinston-Salem, NC 27105
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Hillside Gardens
2 Bedroom Apartments

Hillside Gardens

1350 N Chestnut StWinston-Salem, NC 27105
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The Livery Apartments
Studio to 1 Bedroom Apartments

The Livery Apartments

648 Holly AveWinston-Salem, NC 27101
  • Utilities Included

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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555 East Apartments
2 Bedroom Apartments

555 East Apartments

555 N Martin Luther King Jr DrWinston-Salem, NC 27101
  • Utilities Included
Showing Results 1-37, Page 1 of 1

Skyland, Winston-Salem, NC Local Guide

Cheapest Available Skyland Apartments for Rent

 

The cheapest available apartment rental in the Skyland area of Winston-Salem, NC is a 2 Beds unit found at Kensington Village priced from $925. Privately Owned Crestwood Gardens! has the second lowest priced unit, which is a 2 Beds apartment currently listed from $999. Here are the most affordable Skyland apartments for rent in Winston-Salem, NC:

Apartment ListingModel NameBed/BathPriced From
Kensington VillageThe Lancaster2BR,1BA$925
Privately Owned Crestwood Gardens!2 Bed/ 1 Bath2BR,1BA$999
Link Apartments® 4th StreetA11BR,1BA$1,188
209 N Spring St1BR/1.0BA1BR,1BA$1,195
Brown School Lofts at Legacy Heights1 Bedroom Garden1BR,1BA$1,275
Gateway Apartments1.11BR,1BA$1,300
Plant 64 Apartment Homes1K1BR,1BA$1,350
The ArtreauxA2.01BR,1BA$1,354
Chatham Place Apartments1BR/1.0BA1BR,1BA$1,400
Village Lofts Apartments2BR/1.0BA2BR,1BA$1,460

Best Value Apartments for Rent in Skyland, NC

As of December 01, 2025 the best value apartment in the Skyland area is the $1.51 price per square foot Kahlo Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $1,480. The second greatest value Skyland apartment is the Cottage 3 Bed / 1 Bath Model at Privately Owned Crestwood Gardens! starting at $1,099 with a $1.37 price per square foot in the East Winston Salem neighborhood. Here is today’s list of the best values for Skyland apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
Gallery LoftsKahlo1BR,1BA$1.51
Privately Owned Crestwood Gardens!Cottage 3 Bed / 1 Bath3BR,1BA$1.37
209 N Spring St1BR/1.0BA1BR,1BA$1.51
Fairfield Apartments2BR / 1BA2BR,1BA$1.22
Gateway Apartments1.11BR,1BA$1.68
Village Lofts Apartments2BR/1.0BA2BR,1BA$2.01
Kensington VillageThe Lancaster2BR,1BA$1.31
Plant 64 Apartment Homes1E1BR,1BA$2.26
Brown School Lofts at Legacy Heights1 Bedroom Garden1BR,1BA$1.92
Hilltop HouseA41BR,1BA$1.89

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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The 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.

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Quick Rent Budget Calculator

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 Lifestyle
Skyland, Winston-Salem, NC

Ranked #74

Among cities in North Carolina for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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Best Local Schools in
Skyland, Winston-Salem, NC

School data provided by Great Schools

Getting Around the Skyland Neighborhood in Winston-Salem, NC

Walk Score®

18 / 100

Car-Dependent

Almost all errands require a car

Bike Score®

35 / 100

Somewhat Bikeable

Minimal bike infrastructure

What Are Walk Score®, Transit Score®, and Bike Score® Ratings?

  • Walk Score® measures the walkability of any address.
  • Transit Score® measures access to public transit.
  • Bike Score® measures the bikeability of any address.

Frequently Asked Questions about Cheap Skyland Apartments

What is the price of a cheap apartment in Skyland?

The cheapest apartment in Skyland is Link Apartments® 4th Street which is listed at $1,188, while the average apartment in Skyland costs $1,902.

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 44 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 $886 which is $1,016 cheaper than the average rent for all rentals in Skyland.

Expert Rental Resources

Helpful Apartment Articles, How-To's and Tips

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.

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Apartment Common Area Rules: What Renters Need to Know

Written by: Christine Leonard, Esq.

Back in the day when I rented one of my first apartments, the property didn’t even have laundry in the building. Now, rental properties are often competing against each other to provide the best amenities.

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How to Negotiate Your Apartment Lease and Save Money

Written by: Christine Leonard, Esq.

Everything is a negotiation in real estate! 

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The Rental Move-In Inspection Checklist: A Guide for Renters

Written by: Trey Huguley

The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

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Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between

Written by: Christine Leonard, Esq.

For many people, obstacles can arise during the rental application process for a variety of issues.