Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $575 (59 Rentals)

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

property at 412 W 1st St

$795 - $995

1 Bedroom Rentals

Available Now

412 W 1st St

Winston-SalemNC27101

Rent According to Income: A Look at Income-Restricted Rentals

Find income-restricted rentals and housing subsidies. Explore government programs designed to help low-income families secure stable, affordable housing.

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Renters Insurance 101: What It Is, What It Covers, and Why You Need It

From theft to fire to water damage, the unexpected can happen to any renter. Discover why renters insurance is one of the smartest and most affordable investments you can make as a tenant.

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property at 1615 Argonne Blvd

$1,050

Total Monthly Price

Total Monthly Price

Base Rent
$1,050
Total Monthly Price
$1,050

2 Bedroom, 2 Bath Home for Rent

Available Now

1615 Argonne Blvd

Winston-SalemNC27107
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Hilltop House
$1,072 - $1,353
Total Monthly Price

Total Monthly Price

Base Rent
$1,072 - $1,353
Total Monthly Price
$1,072 - $1,353
1 to 2 Bedroom Apartments Available Sep 4

Hilltop House

241 S Cherry StWinston-Salem, NC 27101
Pet Friendly
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property at 1926 Kentucky Ave

$1,075

Total Monthly Price

Total Monthly Price

Base Rent
$1,075
Total Monthly Price
$1,075

3 Bedroom, 1 Bath Home for Rent

Available Now

1926 Kentucky Ave

Winston-SalemNC27101

How I Find the Perfect Rental for My Clients: A Real Estate Pro's Guide

Finding the right apartment starts with three things: location, cost, and amenities. Get the insider perspective from a real estate professional on how to nail all three.

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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
  • Utilities Included

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.

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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
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Aster Park Apartments
1 to 4 Bedroom Apartments

Aster Park Apartments

1620 Hope LnWinston-Salem, NC 27105
  • Utilities Included

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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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 1 Bed unit found at 1350 N. Chestnut St. priced from $850. The Livery Apartments has the second lowest priced unit, which is a 1 Bed apartment currently listed from $875. Here are the most affordable Skyland apartments for rent in Winston-Salem, NC:

Apartment ListingModel NameBed/BathPriced From
1350 N. Chestnut St.1BR/1.0BA1BR,1BA$850
The Livery Apartments1 Bed1BR,1BA$875
Kensington VillageThe Saville1BR,1BA$910
Crestwood Gardens2 Bed/ 1 Bath2BR,1BA$925
Fairfield Apartments2BR / 1BA2BR,1BA$950
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$990
Village Lofts1BR/1.0BA1BR,1BA$1,035
664 2nd St NWTwo Bedroom One Bath2BR,1BA$1,095

Best Value Apartments for Rent in Skyland, NC

As of August 31, 2026 the best value apartment in the Skyland area is the $1.51 price per square foot Miro Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $2,120. The second greatest value Skyland apartment is the Two Bedroom One Bath Model at 664 2nd St NW starting at $1,095 with a $1.10 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 LoftsMiro2BR,2BA$1.51
664 2nd St NWTwo Bedroom One Bath2BR,1BA$1.10
Village Lofts2BR/2.0BA2BR,2BA$1.61
2425-2445 Old Greensboro Rd2 Bedroom2BR,1BA$1.10
705 Alexander St, Unit 1705 Alexander St2BR,1BA$0.98
1225 New Hope Ln, Unit D1225 New Hope Ln2BR,1BA$1.03
Fairfield Apartments2BR / 1BA2BR,1BA$1.22
Gateway Apartments1.11BR,1BA$1.68
Crestwood Gardens2 Bed/ 1 Bath2BR,1BA$1.22
The Livery Apartments1 Bed1BR,1BA$1.64

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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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.

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Pet Friendly Lifestyle
Skyland, Winston-Salem, NC

Ranked #80

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 a cheap apartment in Skyland?

A cheap apartment is any apartment up to the 30% percentile of cost for the area, which in Skyland is under $1,095.

What is the price of a cheap apartment in Skyland?

The cheapest apartment in Skyland is 1350 N. Chestnut St. which is listed at $850, while the average apartment in Skyland costs $1,455.

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 42 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 $787 which is $668 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

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Rent According to Income: A Look at Income-Restricted Rentals

Written by: Robin Stewart

The idea of affordable housing can be subjective. Every individual is in a different place financially and vocationally. What one may easily afford could be a struggle for someone else.

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Practical Tips for Renters: How to Identify a Great Rental and Avoid Red Flags

Written by: Robin Stewart

Renters want to find a great apartment, the right place for them, one that checks all the boxes of location, rental cost, amenities, safety, and more.

decorative image for First Apartment Regrets: Real Renters Share What They'd Do Differently article

First Apartment Regrets: Real Renters Share What They'd Do Differently

Written by: Robin Stewart

Hindsight is 20/20. Live and Learn. With age comes wisdom. We’re familiar with all those expressions, and all of them apply to lessons first-time renters learn.

decorative image for Renters Insurance 101: What It Is, What It Covers, and Why You Need It article

Renters Insurance 101: What It Is, What It Covers, and Why You Need It

Written by: Robin Stewart

Insurance seems to be a part of life. In some states, having insurance is the law, as is the case for automobile insurance. Renters are no exception.