Cheap Apartments for Rent in the Sleepy Hollow Neighborhood of Leesburg, FL from $500 (11 Rentals)

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Search the lowest-cost Apartments available for rent right now in the Sleepy Hollow area of Leesburg.

property at 33305 Ryan Dr

33305 Ryan Dr

LeesburgFL34788
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Palm Brook
1 to 2 Bedroom Apartments

Palm Brook

1 Brook CirLeesburg, FL 34748
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The Blackwell
1 Bedroom Apartments

The Blackwell

815 Washington StLeesburg, FL 34748

Sleepy Hollow, Leesburg, FL Local Guide

Cheapest Available Sleepy Hollow Apartments for Rent

 

The cheapest available apartment rental in the Sleepy Hollow area of Leesburg, FL is a 1 Bed unit found at Windemere Villas A 55+ Community priced from $995. Arbours at Silver Lake has the second lowest priced unit, which is a 1 Bed apartment currently listed from $1,075. Here are the most affordable Sleepy Hollow apartments for rent in Leesburg, FL:

Apartment ListingModel NameBed/BathPriced From
Windemere Villas A 55+ Community1BR/1BA1BR,1BA$995
Arbours at Silver LakeONE BEDROOM1BR,1BA$1,075
The Blackwell1/1 Renovated Upstairs1BR,1BA$1,099
Laurel Oaks2bedroom/2bathroom2BR,2BA$1,110
Gardens on GriffinWillow 1x11BR,1BA$1,225

Best Value Apartments for Rent in Sleepy Hollow, FL

As of March 29, 2025 the best value apartment in the Sleepy Hollow area is the $1.06 price per square foot 33201 Irongate Dr Model at 33201 Irongate Dr in the in the Silver Lake Estates neighborhood starting from $2,295. The second greatest value Sleepy Hollow apartment is the 33327 Irongate Dr Model at 33327 Irongate Dr starting at $1,955 with a $1.21 price per square foot in the Silver Lake Estates neighborhood. Here is today’s list of the best values for Sleepy Hollow apartments based on price per square foot:

Apartment ListingModel NameBed/BathPrice Per Sq.Ft.
33201 Irongate Dr33201 Irongate Dr3BR,2BA$1.06
33327 Irongate Dr33327 Irongate Dr3BR,2BA$1.21
Lake Griffin ReserveAllex3BR,2BA$1.41
Laurel Oaks2bedroom/2bathroom2BR,2BA$1.07
Lake Harris CoveTwo Bedroom Two Bath2BR,2BA$1.48
Arbours at Silver LakeONE BEDROOM1BR,1BA$1.29
Gardens on GriffinWillow 1x11BR,1BA$1.66
Windemere Villas A 55+ Community1BR/1BA1BR,1BA$1.53
Blueberry HillOne Bedroom One Bath Apartment1BR,1BA$2.13
The Blackwell1/1 Renovated Downstairs1BR,1BA$2.21

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Pet Friendly Lifestyle
Sleepy Hollow, Leesburg, FL

Ranked #1

Among neighborhoods in Leesburg, FL for Apartment listings with Pet Friendly Amenities

Pet Friendliness Lifestyle Score

4.0
Pet Friendly

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Lifestyle Ratings

Our team of engineers and researchers is proud to bring you our detailed rental search system called 'Lifestyle ratings', composed of rentals in areas across the United States and customized analysis for Leesburg, Florida. LifeStyle Ratings are a useful tool for comparing and sorting apartments and neighborhoods when choosing your rental home. This takes in many factors including filtering automatically for outdoor amenities like tennis courts, luxury housing options, kid and pet-friendly communities, availability of transit options, and much more. These search options are in the site filters at the top of this page.

Getting Around the Sleepy Hollow Neighborhood in Leesburg, FL

Walk Score®

9 / 100

Car-Dependent

Almost all errands require a car

Bike Score®

17 / 100

Somewhat Bikeable

Minimal bike infrastructure

Frequently Asked Questions about Cheap Sleepy Hollow Apartments

What is the price of a cheap apartment in Sleepy Hollow?

The cheapest apartment in Sleepy Hollow is Windemere Villas A 55+ Community which is listed at $995, while the average apartment in Sleepy Hollow costs $1,602.

What types of apartments are the cheapest in Sleepy Hollow?

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 3 regular apartments in Sleepy Hollow that we think qualify as ‘cheap apartments’ that do not have special requirements to apply to rent.

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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Understanding Amenity Fees: Know Where You Might Be Able to Save Money

Written by: Amber Kanuckel

With the rising costs of housing, a lot of renters are asking this question: Is it possible to opt out of various amenities that your rental property offers so that you can avoid paying the fees.

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Renting Smart: Lease Basics Every Renter Needs

Written by: Christine Leonard, Esq.

Often, in the excitement of finding a new place to live, there’s a rush to make it happen, and - too often - a new tenant signs a lease without reading it carefully.

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Battling the Butts: Your Guide to the Reality of Smoke-Free Renting

Written by: Andrea Lee Negroni, JD

While many apartment buildings are “no smoking” properties, it’s hard to know exactly how many. In 2017, the National Apartment Association reported more than half of rental properties had smoke free policies.

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How Your Move-In Inspection Can Protect Your Security Deposit

Written by: Christine Leonard, Esq.

If you’re anything like most people, housing costs represent a huge chunk of your monthly budget. On top of that, moving can be both a stressful and expensive affair.