Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (45 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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Hilltop House
$989 - $1,610
Total Monthly Price

Total Monthly Price

Base Rent
$939 - $1,560
Required Monthly Fees
$50
Total Monthly Price
$989 - $1,610
1 to 2 Bedroom Apartments Available Now

Hilltop House

241 S Cherry StWinston-Salem, NC 27101
Affordability
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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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Fairview Landing
1 to 2 Bedroom Apartments

Fairview Landing

1120 Burke Village LnWinston-Salem, NC 27105
  • 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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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

Smart Renter's Guide: Calculating Affordable Rent & Housing Costs

Wondering how to determine your rental budget? This comprehensive guide covers everything from the 30% rule to hidden fees and effective budgeting strategies.

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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

Navigating the Rental Market: Tips for First-Time Renters

Entering the rental market? Learn these simple tips and strategies to avoid common pitfalls and make confident choices. Rent with peace of mind.

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Showing Results 1-45, 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 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 ListingModel NameBed/BathPriced From
Kensington VillageThe Saville1BR,1BA$850
Fairfield Apartments2BR / 1BA2BR,1BA$950
Hilltop HouseA31BR,1BA$989
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$990
Crestwood Gardens2 Bed/ 1 Bath2BR,1BA$999
Chatham Place Apartments1BR/1.0BA1BR,1BA$1,040
Village Lofts Apartments1BR/1.0BA1BR,1BA$1,130
Skyview Townhomes2 Bedroom2BR,1BA$1,200
Link Apartments® 4th StreetA11BR,1BA$1,208
Brown School Lofts at Legacy Heights1 Bedroom Garden1BR,1BA$1,275

Best Value Apartments for Rent in Skyland, NC

As of March 02, 2026 the best value apartment in the Skyland area is the $1.55 price per square foot Kahlo Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $1,515. The second greatest value Skyland apartment is the UNIT 104B, 204B, 304B, 404B, 504B Model at Winston Factory Lofts starting at $1,695 with a $1.77 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 ListingModel NameBed/BathPrice Per Sq.Ft.
Gallery LoftsKahlo1BR,1BA$1.55
Winston Factory LoftsUNIT 104B, 204B, 304B, 404B, 504B2BR,2BA$1.77
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$1.10
109 Vintage Ave, Unit Henny's Haven109 Vintage Ave1BR,1BA$1.63
Chatham Place Apartments1BR/1.0BA1BR,1BA$1.32
Fairfield Apartments2BR / 1BA2BR,1BA$1.22
Gateway Apartments1.11BR,1BA$1.68
Crestwood Gardens2 Bed/ 1 Bath2BR,1BA$1.31
Hilltop HouseA41BR,1BA$1.85
Kensington VillageThe Saville1BR,1BA$1.60

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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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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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 #78

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

Frequently Asked Questions about Cheap Skyland Apartments

How much is rent for a Cheap One Bedroom Skyland Apartment?

The lowest price for a Cheap One Bedroom Skyland Apartment is $850 at Kensington Village.

What is the lowest price for a Cheap Two Bedroom Skyland Apartment for rent?

Today's best deal for a Cheap Two Bedroom Apartment in Skyland is starting from $925 at Kensington Village.

What is the most affordable Skyland Three Bedroom Apartment?

The best deal on a cheap Skyland Three Bedroom Apartment rental is at Crestwood Gardens and starts from $1,099.

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

decorative image for Maximizing Your Refund: Essential Tax Tips for Renters article

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.

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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.

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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.

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Renting with Roommates: Realistic Expectations for Shared Lease

Written by: Christine Leonard, Esq.

Given the high costs for housing, I have found that many people are looking for a roommate to share expenses. These arrangements can increase opportunities for more desirable and larger spaces.