Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (58 Rentals)

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

property at 2001 S Main St

$825 - $945

1 To 2 Bedroom Rentals

Available Now

2001 S Main St

Winston-SalemNC27127

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

$995 - $1,200

1 To 2 Bedroom Rentals

Available Now

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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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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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
  • 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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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
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2001 S Main St
2 Bedroom Apartments

2001 S Main St

2001 S Main StWinston-Salem, NC 27127
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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 1-50, Page 1 of 2

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. 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 Lancaster2BR,1BA$925
Fairfield Apartments2BR / 1BA2BR,1BA$950
Hilltop HouseA31BR,1BA$989
Privately Owned Crestwood Gardens!2 Bed/ 1 Bath2BR,1BA$999
Village Lofts Apartments1BR/1.0BA1BR,1BA$1,125
Brown School Lofts at Legacy Heights1 Bedroom Garden1BR,1BA$1,275
Gateway Apartments1.11BR,1BA$1,300
The ArtreauxA1.01BR,1BA$1,316
Plant 64 Apartment Homes1K1BR,1BA$1,334
Chatham Place Apartments1BR/1.0BA1BR,1BA$1,400

Best Value Apartments for Rent in Skyland, NC

As of January 16, 2026 the best value apartment in the Skyland area is the $1.83 price per square foot B2 Model at Link Apartments® 4th Street in the in the Downtown Winston Salem neighborhood starting from $2,025. The second greatest value Skyland apartment is the Kahlo Model at Gallery Lofts starting at $1,515 with a $1.55 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.
Link Apartments® 4th StreetB22BR,2BA$1.83
Gallery LoftsKahlo1BR,1BA$1.55
Winston Factory LoftsUNIT 606B2BR,2BA$1.93
Privately Owned Crestwood Gardens!Cottage 3 Bed / 1 Bath3BR,1BA$1.37
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
Brown School Lofts at Legacy Heights1 Bedroom Garden1BR,1BA$1.92
Hilltop HouseA51BR,1BA$1.92

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 #65

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

Frequently Asked Questions about Cheap Skyland Apartments

What is the price of a cheap apartment in Skyland?

The cheapest apartment in Skyland is Hilltop House which is listed at $989, while the average apartment in Skyland costs $1,899.

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 $830 which is $1,069 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

decorative image for A Renters Guide for Tips on Writing Your Notice for Not Renewing Your Apartment article

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.

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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!