Cheap Homes for Rent in Rolling Oaks Neighborhood of Windsor Mill, MD from $1,900 (1 Rental)

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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

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 ListingModel NameBed/BathPrice Per Sq.Ft.
Residences at Pomona Park3 Bed 2 Bath3BR,2BA$1.55
Annen Woods Apartments2 Bedroom 2 Bath Deluxe2BR,2BA$1.44
Marrion Square Apartments3 Bedroom 2 Bath3BR,2BA$1.52
Villas at 4607Kings Peak2BR,2BA$1.47
Liberty Place2 Bed 1 Bath2BR,1BA$1.25
The Townhomes at Diamond RidgeThree Bedroom 1.5 Bath Townhome - 1,080 sqft3BR,1.5BA$1.56
Liberty WestRenovated Two Bedroom2BR,1BA$1.55
BrenbrookThe Americana1BR,1BA$1.47
Northwest Crossing Apartment HomesTwo Bedroom 1.5 Bath2BR,1.5BA$1.54
Gwynn Oaks Landing Apartments and TownhomesOne Bedroom - 705 sqft1BR,1BA$1.62

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Pet Friendly Lifestyle
Rolling Oaks, Windsor Mill, MD

Ranked #3

Among cities in Maryland for Apartment listings with Pet Friendly Amenities.

Pet Friendliness Lifestyle Score

3.5
Pet Friendly

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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.

decorative image for A Baltimore Local Expert’s Guide To 10 Budget-Friendly Neighborhoods to Rent article

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.

decorative image for The Rental Move-In Inspection Checklist: A Guide for Renters article

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.

decorative image for Your Guide to Co-Signers: The Risks, Rewards, and Everything in Between article

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.

decorative image for The Ultimate Long-Distance Moving Checklist: Tips from a Real Estate Pro article

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.