Oakland, Orange County, FL Office Spaces for Rent

Find the best Oakland, Orange County, FL office space among 16 for rent listings currently on the market.

16123 W Colonial Dr

16123 W Colonial Dr, Oakland, FL
Property Type

Office
For Lease Contact for pricing

1 space available / 2,500 SF
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Winter Garden Regional Medical Building

14237 W Colonial Dr, Winter Garden, FL
Property Type

Office
For Lease

$32.00/SF/YR
1 space available / 2,350 SF
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Gateway Center

15701 State Road 50, Greater Hills, Clermont, FL
Property Type

Office
For Lease

$22.00/SF/YR
1 space available / 1,840 SF
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Gateway Center

15701 State Road 50, Greater Hills, Clermont, FL
Property Type

Office
For Lease

$22.00/SF/YR
1 space available / 1,840 SF
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FL, Winter Garden - Plant St
Regus
504 West Plant Street, Winter Garden, FL
Property Type

Private Offices
For Lease

From $539/month
Space for 1 to 15 people
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21 W Smith St

21 W Smith St, Winter Garden, FL
Property Type

Office
For Lease

$35.00/SF/YR
2 spaces available / 1,300 SF
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Dillard Place - Suite 114

1002 Dillard Street, Winter Garden, FL
Property Type

Office
For Lease

$28.00/SF/YR
1 space available / 1,500 SF
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Dillard St Center

730 S Dillard St, Winter Garden, FL
Property Type

Retail
For Lease

$25.00/SF/YR
1 space available / 2,279 SF
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Daniels Medical Office Park - 1219-1239 Daniels Road

1219 Daniels Road, Winter Garden, FL
Property Type

Office
For Lease Contact for pricing

2 spaces available / 7,462 - 10,000 SF
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Stoneybrook Exchange - Building 9

Stoneybrook W Pkwy & Windermere Rd, Winter Garden, FL
Property Type

Mixed Use
For Lease

$35.00 - $42.00/SF/YR
5 spaces available / 1,500 - 2,810 SF
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1133 Crown Park Circle

1133 Crown Park Circle, Winter Garden, FL
Property Type

Office
For Lease

$26.00/SF/YR
1 space available / 6,500 SF
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Frequently Asked Questions

Asking prices vary based on the property location, rating, amenities such as proximity to restaurants, cafes, and entertainment venues, as well as convenience of access to public transport, airports, and thoroughfares.
Most experts recommend an average of between 75 and 150 square feet of office space per person. However, it is important to keep in mind that how much office space you ultimately need depends on your activity and how you need to use the space, as much as it does on how many people it should accommodate. If you already know what size office would best suit your needs, use the available space size filter at the top of the search page to focus your search on the best fit for you.

You’ll find a home for almost any size of business in Oakland, as the local office market offers a wide range of options. Office spaces currently on the market go up to as much as 2,500 square feet in size for an individual listing.
You can find 1 office listing(s) for lease in Oakland, which add up to a total of 2,500 square feet. Availability on the market includes a variety of office use types, such as Medical Office.

The most common office use type currently available for lease in Oakland is Medical Office, which is offered in 1 or 100.00% of listings.
Sublease opportunities on the market include Medical Office.
The best choice of neighborhood for your office space will greatly depend on the elements that are most relevant to your business and your employees. However, a good criterion to start with is to look at the areas of the city that have the highest concentration of office properties, as these areas are generally well connected to transit options and have a good degree of amenity availability.
Each individual’s commuting experience will of course be different depending on a number of factors. Check the location description details for the office listings that catch your eye, to get an overview of walkability, access to public transport, the quality of infrastructure dedicated to biking commuters, as well as the proximity to parking facilities, fuel stations, and other essential amenities.
The Oakland office market incorporates a mix of properties of various ages, ratings, construction grades, and other quality indicators. Class B office space accounts for 100% of spaces listed on the leasing market.

Buildings completed in and since the year 2000 account for 200% of office properties in the city and incorporate a total of 51,962 square feet. About 100% of office space in Oakland is in buildings that have been renovated at least once since 2000.
There are, of course, a lot of things to factor in when you are looking for office space. Aspects including the accessibility of the location, the quality of the facility, the size of the space, the convenience of nearby amenities, the type and duration of the lease, and of course the cost are all part of the search and decision process. For a quick checklist of what you should take into account when researching the market, consider these seven tips for choosing the best office location for your business. Alternatively, for a comprehensive take on everything to consider when looking for office space, see our in-depth guide to finding office space for small or growing companies. The guide also includes insights from seasoned professionals and can serve as a helpful resource for growing companies, no matter their current size.
Are you looking to lease office space in the vicinity of your current location or in a particular neighborhood of Oakland? Using the interactive map, you can easily navigate to your preferred location and customize your search area around a specific point of interest. Select “Radius” from the Search Mode options menu, click on the map to set your search reference point, and expand the radius to select your desired search area. Browse available listings to find the best office space that meets your location, as well as other business needs.

Oakland, Orange County, FL Office Inventory Breakdown

There are a number of factors that make a city attractive for businesses to relocate or expand, as well as for investors to enhance their portfolios through local acquisitions. Among the most important factors to consider are the size and quality of the local office market, which is an essential component of the local economy.

Total Office Space in Oakland: 52,800 Sq. Ft.

In 2025 the Oakland office market encompassed 52,800 square feet of space.

Oakland Office Market Breakdown by Building Size
Building Size Range	Total Square Feet	Share of Total Office
50k to 100k Sq. Ft.	52,800 Sq. Ft.	100%

Oakland Office Market Breakdown by Building Quality Rating
Class	Total Square Feet	Share of Total Office
Class B	52,800 Sq. Ft.	100%

Data was provided by CommercialEdge, refers to properties larger than 50,000 square feet.

About us

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Oakland, Orange County, FL Office Spaces for Rent

16123 W Colonial Dr

Winter Garden Regional Medical Building

Gateway Center

Gateway Center

FL, Winter Garden - Plant St

21 W Smith St

Dillard Place - Suite 114

Dillard St Center

Daniels Medical Office Park - 1219-1239 Daniels Road

Stoneybrook Exchange - Building 9

1133 Crown Park Circle

Frequently Asked Questions

Oakland, Orange County, FL Office Inventory Breakdown

Total Office Space in Oakland: 52,800 Sq. Ft.

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