
Cheap Homes for Rent in Rolling Oaks Neighborhood of Windsor Mill, MD from $1,900 (1 Rental)
Search the lowest-cost Homes available for rent right now in the Rolling Oaks area of Windsor Mill.

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.
Rolling Oaks, Windsor Mill, MD Local Guide

How much does it cost to rent a home in Rolling Oaks?
Bedroom | Average Rent | Cheapest Rent | Highest Rent |
---|---|---|---|
Rolling Oaks 3 Bedroom Homes for Rent | $1,995 | $1,995 | $1,995 |
Rolling Oaks 4 Bedroom Homes for Rent | $3,581 | $3,300 | $3,863 |
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Rolling Oaks, Windsor Mill, MD Local Guide
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Best Value Apartments for Rent in Rolling Oaks, MD
As of September 10, 2025 the best value apartment in the Rolling Oaks area is the $1.55 price per square foot 3 Bed 2 Bath Model at Residences at Pomona Park in the in the Rolling Oaks neighborhood starting from $2,633. The second greatest value Rolling Oaks apartment is the 2 Bedroom 2 Bath Deluxe Model at Annen Woods Apartments starting at $1,817 with a $1.44 price per square foot in the Rolling Oaks neighborhood. Here is today’s list of the best values for Rolling Oaks apartments based on price per square foot:
Apartment Listing | Model Name | Bed/Bath | Price Per Sq.Ft. |
---|---|---|---|
Residences at Pomona Park | 3 Bed 2 Bath | 3BR,2BA | $1.55 |
Annen Woods Apartments | 2 Bedroom 2 Bath Deluxe | 2BR,2BA | $1.44 |
Marrion Square Apartments | 3 Bedroom 2 Bath | 3BR,2BA | $1.52 |
Villas at 4607 | Kings Peak | 2BR,2BA | $1.47 |
Liberty Place | 2 Bed 1 Bath | 2BR,1BA | $1.25 |
The Townhomes at Diamond Ridge | Three Bedroom 1.5 Bath Townhome - 1,080 sqft | 3BR,1.5BA | $1.56 |
Liberty West | Renovated Two Bedroom | 2BR,1BA | $1.55 |
Brenbrook | The Americana | 1BR,1BA | $1.47 |
Northwest Crossing Apartment Homes | Two Bedroom 1.5 Bath | 2BR,1.5BA | $1.54 |
Gwynn Oaks Landing Apartments and Townhomes | One Bedroom - 705 sqft | 1BR,1BA | $1.62 |
Quick Rent Budget Calculator
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Pet Friendly LifestyleRolling Oaks, Windsor Mill, MD
Ranked #3
Among cities in Maryland for Apartment listings with Pet Friendly Amenities.
Pet Friendliness Lifestyle Score
3.5Pet Friendly
Best Local Schools in Rolling Oaks, Windsor Mill, MD
Northwest Academy of Health Sciences
School data provided by Great Schools
Frequently Asked Questions about Rolling Oaks
What type of rentals are currently available in Rolling Oaks?
There are currently 58 Apartments for Rent in Rolling Oaks, MD with pricing that ranges from $985 to $2,808. There are also 2 Single Family Homes for rent, Condos, and Townhome rentals currently available in Rolling Oaks ranging from $1,995 to $3,863.
What is the current price range for Rental Homes in Rolling Oaks?
Today's rental pricing for Homes for Rent, Condos and Townhomes in Rolling Oaks ranges from $1,995 to $3,863 with an average monthly rent of $2,788.
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.

A Baltimore Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent
Written by: Sarah Bregel
There are few cities more eclectic and diverse than Baltimore, Maryland. I should know. I've lived in various parts of Baltimore for most of my life.

The Rental Move-In Inspection Checklist: A Guide for Renters
Written by: Trey Huguley
The move-in inspection checklist is a crucial tool for both tenants and landlords. This checklist, provided by the team at ApartmentHomeLiving.com, helps document the condition of an apartment at the time of move-in.

Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between
Written by: Christine Leonard, Esq.
For many people, obstacles can arise during the rental application process for a variety of issues.

The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro
Written by: Christine Leonard, Esq.
Hard truth. Moving is never easy. I’ve done it all – from local moves to cross-country relocations From packing to unpacking the last box, I have found moving to be an exhausting, expensive and stressful experience every time.