Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (42 Rentals)

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

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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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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Fairview Landing
1 to 2 Bedroom Apartments

Fairview Landing

1120 Burke Village LnWinston-Salem, NC 27105
  • Utilities Included

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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Colony Place Apartments
1 to 3 Bedroom Apartments

Colony Place Apartments

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

Aster Park Apartments

1620 Hope LnWinston-Salem, NC 27105
  • Utilities Included
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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

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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555 East Apartments
2 Bedroom Apartments

555 East Apartments

555 N Martin Luther King Jr DrWinston-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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Showing Results 1-42, 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
Village Lofts Apartments0BR/1.0BAStudio,1BA$1,000
Chatham Place Apartments1BR/1.0BA1BR,1BA$1,000
Link Apartments® Innovation QuarterS21BR,1BA$1,219
Link Apartments® 4th StreetA11BR,1BA$1,242
The ArtreauxA3.2Studio,1BA$1,299
Gateway Apartments1.11BR,1BA$1,300
50 West Fourth Residences1 Beds, 1 Baths1BR,1BA$1,325
Plant 64 Apartment Homes1K1BR,1BA$1,380

Best Value Apartments for Rent in Skyland, NC

As of October 17, 2025 the best value apartment in the Skyland area is the $1.39 price per square foot Calder Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $1,915. The second greatest value Skyland apartment is the B4 Model at Hilltop House starting at $1,630 with a $1.67 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 ListingModel NameBed/BathPrice Per Sq.Ft.
Gallery LoftsCalder2BR,2BA$1.39
Hilltop HouseB42BR,2BA$1.67
Brown School Lofts at Legacy Heights2 Bedroom Garden2BR,1BA$1.63
Privately Owned Crestwood Gardens!Cottage 3 Bed / 1 Bath3BR,1BA$1.37
Gateway Apartments1.11BR,1BA$1.68
Kensington VillageThe Lancaster2BR,1BA$1.31
50 West Fourth Residences1 Beds, 1 Baths1BR,1BA$1.92
Plant 64 Apartment Homes1E1BR,1BA$2.15
Winston Factory LoftsUNIT 202B, 302B, 402B, 502B, 602B1BR,1BA$2.40
Village Lofts Apartments0BR/1.0BAStudio ,1BA$2.39

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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Pet Friendly Lifestyle
Skyland, Winston-Salem, NC

Ranked #58

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

Pet Friendliness Lifestyle Score

3.0
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 Chatham Place Apartments which is listed at $1,000, while the average apartment in Skyland costs $1,803.

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 45 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 $810 which is $993 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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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.

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The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro

Written by: Christine Leonard, Esq.

Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.