Oakshire

Oakshire is a community of single family homes, and townhomes in Orlando, Florida, with a range of options priced between $270,000 and $425,000. There are currently a total of 7 homes for sale in Oakshire. The smallest Oakshire home presently available is a four bedroom two bathroom residence that is 1,276 square feet (1,246SF Under Air living space), and the largest of the Oakshire homes currently on the market has four beds and two baths and is a 2,579 square foot (1,837SF Under Air) residence.

Property management fees in Orange County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in Oakshire range from $250 to $264 and $400 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, the community pool, security, and real estate taxes for common areas. Also included is property insurance, water, trash removal, sewer, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular Oakshire home.

The Oakshire HOA rules do allow homeowners to have pets although there are certain breed restrictions. Dogs and cats are allowed.

There are four commercial airports that serve Oakshire - Kissimmee Gateway (ISM), which is six miles away; Orlando International (MCO), which is six miles away; Orlando Executive (ORL), which is thirteen miles away, and Orlando Sanford International (SFB), which is 30 miles away from Oakshire.

Oakshire real estate activity on the Orlando MLS during the past year (as of September 2025) reflects twenty three homes changing hands, with an average asking price of $397,620 and an average selling price of $391,130. This represents a healthy list-to-sell price ratio of 98% and $168 per square foot. During this period, Oakshire homes for sale have taken an average of 61 days to sell.

In addition, there are numerous other communities in Orlando to choose from, or you may browse all available Orlando Real Estate, including some new construction opportunities. Homes for sale in Oakshire are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Oakshire hits the market. You can also always contact your ZFC Real Estate agent, who would happily assist you further with all your Central Florida real estate needs.

Oakshire Homes For Sale

Reduced

$425,000

$430,000

MLS#MFRO6341303

1348 Heather Lake Dr
Orlando, FL 32824

4

3

2

2,579 SqFt

0.18 Acres

22 Days

$420,000

MLS#MFRO6326008

1208 Sandestin Way
Orlando, FL 32824

4

3

2

2,189 SqFt

Pool

0.08 Acres

76 Days

Reduced

$409,990

$419,990

MLS#MFRS5129575

1101 Sandestin Way
Orlando, FL 32824

4

3

1

1,865 SqFt

Pool

0.13 Acres

79 Days

$394,990

MLS#MFRO6341902

14208 Crystal Key Pl
Orlando, FL 32824

4

3

1

2,189 SqFt

Pool

0.07 Acres

13 Days

$285,000

MLS#MFRS5127445

13940 Corrine Key Pl
Orlando, FL 32824

3

2

1,565 SqFt

0.07 Acres

121 Days

Reduced

$279,900

$299,999

MLS#MFRO6279210

13900 Corrine Key Pl
Orlando, FL 32824

3

2

1,276 SqFt

0.07 Acres

226 Days

$270,000

MLS#MFRO6344661

1135 Madeira Key Way
Orlando, FL 32824

3

3

1,445 SqFt

0.05 Acres

9 Days

7 Active Listings in Oakshire