Oakshire

Oakshire is a community of single family homes, and townhomes in Orlando, Florida, with a range of options priced between $270,000 and $469,000. There are currently a total of 11 homes for sale in Oakshire. The smallest Oakshire home presently available is a three bedroom two bathroom residence that is 1,256 square feet, and the largest of the Oakshire homes currently on the market has five beds and two baths and is a 5,663 square foot (2,522SF 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 $225 to $282 and $400 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, the community pool, and security. Also included is real estate taxes for common areas, 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 November 2025) reflects eighteen homes changing hands, with an average asking price of $386,158 and an average selling price of $380,444. This represents a healthy list-to-sell price ratio of 99% and $186 per square foot. During this period, Oakshire homes for sale have taken an average of 72 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

$469,000

$529,000

MLS#MFROM712437

1010 Raining Meadows Ln
Orlando, FL 32824

5

2

2

2,522 SqFt

0.13 Acres

11 Days

$425,000

MLS#MFRS5136739

1348 Heather Lake Dr
Orlando, FL 32824

4

3

2

2,579 SqFt

0.18 Acres

24 Days

$420,000

MLS#MFRO6326008

1208 Sandestin Way
Orlando, FL 32824

4

3

2

2,189 SqFt

Pool

0.08 Acres

121 Days

$414,990

MLS#MFRTB8436397

14417 Jasmine Glen Dr
Orlando, FL 32824

4

3

2

2,256 SqFt

0.11 Acres

30 Days

$385,000

MLS#MFRO6348556

1258 Sandestin Way
Orlando, FL 32824

3

3

1

2,189 SqFt

0.11 Acres

18 Days

Under Contract

$343,500

$349,500

MLS#MFRO6349054

1424 Timberbend Cir
Orlando, FL 32824

4

3

1

5,663 SqFt

0.13 Acres

37 Days

$334,900

MLS#MFRS5137781

1341 Ivy Meadow Dr
Orlando, FL 32824

3

2

1

1,720 SqFt

0.11 Acres

6 Days

Reduced

$315,000

$350,000

MLS#MFRS5135243

1321 Timberbend Cir
Orlando, FL 32824

3

2

1

1,501 SqFt

0.11 Acres

33 Days

Under Contract

$298,000

MLS#MFRS5136080

1421 Timberbend Cir
Orlando, FL 32824

3

2

1

1,587 SqFt

0.11 Acres

33 Days

$279,997

MLS#MFRS5136136

14012 Boca Key Dr
Orlando, FL 32824

3

2

1,256 SqFt

Water Front

0.07 Acres

26 Days

Under Contract

$270,000

MLS#MFRO6344661

1135 Madeira Key Way
Orlando, FL 32824

3

3

1,445 SqFt

0.05 Acres

54 Days

11 Active Listings in Oakshire