The Oaks Kissimmee

The Oaks is a community of single family homes, condos, and townhomes in Kissimmee, Florida, with a range of options priced between $219,900 and $783,750. There are currently a total of 42 homes for sale in The Oaks. The smallest Oaks home presently available is a three bedroom two bathroom residence that is 1,136 square feet, and the largest of the The Oaks homes currently on the market has six beds and five baths and is a 5,558 square foot (4,303SF Under Air) residence.

Property management fees in Osceola County vary depending on the community and sometimes vary between homes in the community. The current HOA fees for homes in The Oaks range from $127 to $550 and $250 for a The Oaks condo and $154 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, pest control, Cable TV & internet, and recreation facilities. Please check the individual listing pages for the exact homeowners association fees for a particular The Oaks home.

The Oaks amenities include a clubhouse, swimming pool, and a state-of-the-art fitness center. Sports facilities include a championship golf course, tennis courts, pickleball courts, and basketball court. There is also a community park, a playground, a dog park, as well as walking or jogging trails.

The Oaks HOA rules do allow homeowners to have pets although there are certain breed restrictions. There is a limit of how many pets you may have, and there is a restriction on pet size. Dogs and cats are allowed.

There are four commercial airports that serve The Oaks - Kissimmee Gateway (ISM), which is two miles away; Orlando International (MCO), which is fourteen miles away; Orlando Executive (ORL), which is twenty one miles away, and Orlando Sanford International (SFB), which is 38 miles away from The Oaks.

The Oaks real estate activity on the Kissimmee MLS during the past year (as of March 2026) reflects 49 homes changing hands, with an average asking price of $406,225 and an average selling price of $395,867. This represents a healthy list-to-sell price ratio of 97% and $139 per square foot. During this period, The Oaks homes for sale have taken an average of 113 days to sell.

In addition, there are numerous other communities in Kissimmee to choose from, or you may browse all available Kissimmee Real Estate, including some new construction opportunities. Homes for sale in The Oaks are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in The Oaks 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.

The Oaks Homes For Sale

$783,750

MLS#MFRS5137706

1820 Trophy Bass Way
Kissimmee, FL 34746

6

5

2

5,558 SqFt

0.22 Acres

146 Days

Under Contract

$675,000

$700,000

MLS#MFRO6375071

3105 Bass Boat Way
Kissimmee, FL 34746

4

3

3

3,749 SqFt

Pool

Water Front

0.22 Acres

61 Days

$625,000

MLS#MFRO6376700

3110 Bass Boat Way
Kissimmee, FL 34746

4

4

3

4,263 SqFt

Water Front

0.18 Acres

63 Days

Reduced

$604,990

$624,990

MLS#MFRO6366323

1563 Angler Ave
Kissimmee, FL 34746

6

4

2

4,984 SqFt

0.24 Acres

107 Days

Reduced

$595,000

$625,000

MLS#MFRO6323394

2460 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,347 SqFt

Pool

0.28 Acres

267 Days

Reduced

$549,900

$575,000

MLS#MFRO6371236

1524 The Oaks Blvd
Kissimmee, FL 34746

4

3

2

3,488 SqFt

Pool

0.18 Acres

79 Days

Reduced

$549,000

$569,000

MLS#MFRO6361402

2165 The Oaks Blvd
Kissimmee, FL 34746

4

4

2

3,357 SqFt

0.18 Acres

130 Days

Reduced

$535,000

$589,900

MLS#MFRO6349376

1527 Angler Ave
Kissimmee, FL 34746

5

5

2

3,607 SqFt

Water Front

0.21 Acres

176 Days

Under Contract

$525,000

MLS#MFRO6380884

2220 Tournament Ct
Kissimmee, FL 34746

4

4

2

5,324 SqFt

Pool

0.34 Acres

47 Days

$525,000

MLS#MFRS5142892

2617 Teeside Ct
Kissimmee, FL 34746

3

4

3

3,979 SqFt

Pool

0.25 Acres

55 Days

Reduced

$525,000

$540,000

MLS#MFRO6319826

2530 The Oaks Blvd
Kissimmee, FL 34746

4

3

2

3,707 SqFt

Pool

0.19 Acres

283 Days

Reduced

$525,000

$545,000

MLS#MFRO6365324

3113 Bass Boat Way
Kissimmee, FL 34746

5

4

3

3,170 SqFt

0.15 Acres

113 Days

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42 Active Listings in The Oaks