Cheap Apartments for Rent in the Skyland Neighborhood of Winston-Salem, NC from $500 (34 Rentals)

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

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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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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property at 812 West St

812 West St

Winston-SalemNC27101
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Fairview Landing
1 Bedroom Apartments

Fairview Landing

1120 Burke Village LnWinston-Salem, NC 27105
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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
2 Bedroom Apartments

Aster Park Apartments

1620 Hope LnWinston-Salem, NC 27105
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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
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

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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555 East Apartment Homes
2 Bedroom Apartments

555 East Apartment Homes

555 N Martin Luther King Jr DrWinston-Salem, NC 27101
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Showing Results 1-34, 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 $820. Fairfield Apartments has the second lowest priced unit, which is a 2 Beds apartment currently listed from $925. Here are the most affordable Skyland apartments for rent in Winston-Salem, NC:

Apartment ListingModel NameBed/BathPriced From
Kensington VillageThe Saville1BR,1BA$820
Fairfield Apartments2BR / 1BA2BR,1BA$925
Hilltop HouseA31BR,1BA$949
Crestwood Gardens Apartments2 Bed/ 1 Bath2BR,1BA$999
Chatham Place Apartments1 Bed / 1 Bath1BR,1BA$1,000
Gateway Apartments1.11BR,1BA$1,300
Village Lofts of Winston-Salem2 Bed / 2 Bath2BR,2BA$1,500
50 West Fourth Residences2 Beds, 2 Baths2BR,2BA$1,525
Winston Factory LoftsSUITE 213A, 413A, 513A1BR,1BA$1,595

Best Value Apartments for Rent in Skyland, NC

As of May 28, 2025 the best value apartment in the Skyland area is the $1.55 price per square foot Rivera Model at Gallery Lofts in the in the Downtown Winston Salem neighborhood starting from $1,600. The second greatest value Skyland apartment is the 2 Beds, 2 Baths Model at 50 West Fourth Residences starting at $1,525 with a $1.64 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 LoftsRivera1BR,1BA$1.55
50 West Fourth Residences2 Beds, 2 Baths2BR,2BA$1.64
Village Lofts of Winston-Salem2 Bed / 2 Bath2BR,2BA$1.62
Plant 64 Apartment Homes1P21BR,1BA$2.15
Crestwood Gardens ApartmentsCottage 3 Bed / 1 Bath3BR,1BA$1.37
1225 New Hope Ln, Unit B1225 New Hope Ln2BR,1BA$1.06
Fairfield Apartments2BR / 1BA2BR,1BA$1.19
Gateway Apartments1.11BR,1BA$1.68
Hilltop HouseA41BR,1BA$1.74
Kensington VillageThe Saville1BR,1BA$1.54

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 #46

Among neighborhoods in Winston-Salem, NC 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

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

The lowest price for a Cheap One Bedroom Skyland Apartment is $820 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 Apartments and starts from $1,099.

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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The Art of the Rental Viewing: What to look for during a property tour

Written by: Marie Brown

You’ve scrolled through countless listings, walked through a blur of rentals, and finally found what feels like the one. The pictures? Fantastic. The neighborhood seems just right.

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Know Your Budget: Calculating What You Can Realistically Afford When Renting

Written by: Lauren Harrington

Renting an apartment or house isn’t just about looking through online ads, choosing a few apartments or homes you want to tour, filling out an application, and putting down a deposit. Those things are all necessary and important.

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The Freedom of Short-Term Leases: Exploring the Advantages for Renters

Written by: Bobbi Jackson

If you’re looking to relocate right now, a popular solution that may best fit your current rental needs is a short-term lease.

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Navigating the Rental Market: Tips for First-Time Renters

Written by: Sandy Baker

Making the decision to rent is exciting and terrifying at the same time. For many people, there are a lot of unknowns.