Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (48 Rentals)

How Many Bedrooms?Done
Select your price rangeDone
to
Note: Properties with the Total Monthly Price badge include all required fees. Hover over the badge for details.
Lifestyle Matching SearchDone
Learn more about Lifestyle Search
By AmenitiesDone
By Community TypeDone
Features and AvailabilityDone
Done

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

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.

Read Article

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.

Read Article
close
View Me
Hilltop House
Rent Specials
$1,048 - $1,690
Total Monthly Price

Total Monthly Price

Base Rent
$1,048 - $1,690
Total Monthly Price
Varies
1 to 2 Bedroom Apartments Available Now

Hilltop House

241 S Cherry StWinston-Salem, NC 27101
Pet Friendly
  • Verified
  • Customer Reviewed
  • 3D Tour

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.

Read Article
close
View Me
Fairview Landing
1 to 2 Bedroom Apartments

Fairview Landing

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

Colony Place Apartments

900 N Cleveland AveWinston-Salem, NC 27101
  • 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.

Read Article
close
View Me
1350 N Chestnut St
2 Bedroom Apartments

1350 N Chestnut St

1350 N Chestnut StWinston-Salem, NC 27105
close
View Me
555 East Apartments
2 Bedroom Apartments

555 East Apartments

555 N Martin Luther King Jr DrWinston-Salem, NC 27101
  • Utilities Included
close
View Me
Aster Park Apartments
1 to 4 Bedroom Apartments

Aster Park Apartments

1620 Hope LnWinston-Salem, NC 27105
  • Utilities Included
close
View Me
Salem Gardens
1 to 4 Bedroom Apartments

Salem Gardens

7 Salem Garden DrWinston-Salem, NC 27107
  • 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.

Read Article
close
View Me
209 N Spring St
1 to 2 Bedroom Apartments

209 N Spring St

209 N Spring StWinston-Salem, NC 27101
Showing Results 1-48, 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
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$990
The Livery Apartments1 Bed1BR,1BA$1,020
50 West Fourth Residences0 Beds, 1 BathsStudio,1BA$1,175
Hilltop HouseA41BR,1BA$1,179
Skyview Townhomes2 Bedroom2BR,1BA$1,200
Village Lofts Apartments1BR/1.0BA1BR,1BA$1,220
Brown School Lofts1 Bdrm Garden, 660 SqFt, Market,1BR,1BA$1,275

Best Value Apartments for Rent in Skyland, NC

As of June 02, 2026 the best value apartment in the Skyland area is the $1.51 price per square foot O'Keefe Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $1,705. The second greatest value Skyland apartment is the Two Bedroom One Bath Model at 664 2nd St NW starting at $1,295 with a $1.30 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 LoftsO'Keefe1BR,1BA$1.51
664 2nd St NWTwo Bedroom One Bath2BR,1BA$1.30
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$1.10
Village Lofts Apartments2BR/2.0BA2BR,2BA$1.89
1225 New Hope Ln, Unit D1225 New Hope Ln2BR,1BA$1.03
Fairfield Apartments2BR / 1BA2BR,1BA$1.22
Gateway Apartments1.11BR,1BA$1.68
Brown School Lofts1 Bdrm Garden, 660 SqFt, Market,1BR,1BA$1.93
The Livery Apartments1 Bed1BR,1BA$1.89
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.

Read Article
Decorative image

Real Estate and Rental Term Glossary | ApartmentHomeLiving.com Renter University

From the letter A all the way to the letter Z, the Real Estate and Rental Term Glossary from the content team at ApartmentHomeLiving.com provides our visitors and shoppers with a little clarity and helpful guidance in navigating the real estate world through definitions and explainers for the top subjects and terms that someone may come across during the leasing, buying, or selling process.

Read Article
Decorative image

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.

decorative image of people with a giant lease agreement

Pet Friendly Lifestyle
Skyland, Winston-Salem, NC

Ranked #63

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

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

decorative image of woman handing cat to small boy

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 Winston Factory Lofts and starts from $2,150.

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 Neighborhood and Market Insights: How to Choose the Right Area to Rent article

Neighborhood and Market Insights: How to Choose the Right Area to Rent

Written by: Robin Stewart

Apartment-hunting can be a gargantuan task. Renters have a wish list of items—some luxuries, some necessities—but finding what you seek in the right place is perhaps the most important part of the journey.

decorative image for A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back article

A Seasoned Property Manager's Step-by-Step Guide to Getting Your Deposit Back

Written by: Lauren Harrington

I’m going to talk with you as a seasoned property manager and friend. So, let’s start with your security deposit. I want you to think about this guide as insider information. You deserve your deposit back.

decorative image for Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts article

Expert Solutions for Creating the Perfect Work-From-Home Apartment Layouts

Written by: Lauren Harrington

This article is based on first-hand experience managing apartment communities and helping renters adapt to their spaces after moving in.

decorative image for What Does “Rent Burdened” Mean? How Much Rent Is Too Much article

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.