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 $199,990 and $799,999. There are currently a total of 28 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 four baths and is a 4,984 square foot (4,580SF 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 $23 to $505 and range from $22 to $300 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 June 2026) reflects 48 homes changing hands, with an average asking price of $410,852 and an average selling price of $400,665. This represents a healthy list-to-sell price ratio of 98% and $131 per square foot. During this period, The Oaks homes for sale have taken an average of 119 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 BEX Realty agent, who would happily assist you further with all your Central Florida real estate needs.

The Oaks Homes For Sale

Reduced

$799,999

$824,900

MLS#MFRO6395237

2120 Bunker View Ct
Kissimmee, FL 34746

5

4

4,580 SqFt

Water Front

0.36 Acres

84 Days

$688,999

MLS#MFRS5146993

2987 Boating Blvd
Kissimmee, FL 34746

4

4

2

4,084 SqFt

Pool

0.16 Acres

83 Days

Reduced

$615,000

$625,000

MLS#MFRO6376700

3110 Bass Boat Way
Kissimmee, FL 34746

4

4

3

4,263 SqFt

Water Front

0.18 Acres

150 Days

Under Contract

$560,000

$625,000

MLS#MFRO6323394

2460 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,347 SqFt

Pool

0.28 Acres

354 Days

Under Contract

$539,900

$575,000

MLS#MFRO6371236

1524 The Oaks Blvd
Kissimmee, FL 34746

4

3

2

3,488 SqFt

Pool

0.18 Acres

166 Days

Reduced

$534,500

$569,000

MLS#MFRO6361402

2165 The Oaks Blvd
Kissimmee, FL 34746

4

4

2

3,357 SqFt

0.18 Acres

217 Days

Reduced

$519,900

$549,950

MLS#MFRS5138344

2924 Boating Blvd
Kissimmee, FL 34746

5

3

2

3,744 SqFt

Water Front

0.17 Acres

223 Days

Reduced

$515,000

$525,000

MLS#MFRS5142892

2617 Teeside Ct
Kissimmee, FL 34746

3

4

3

3,979 SqFt

Pool

0.25 Acres

142 Days

Reduced

$450,000

$460,000

MLS#MFRO6377376

2936 Boating Blvd
Kissimmee, FL 34746

5

3

2

3,007 SqFt

0.17 Acres

147 Days

Reduced

$444,900

$449,900

MLS#MFRS5137135

2801 Baywood Ln
Kissimmee, FL 34746

3

3

2

3,121 SqFt

Pool

0.22 Acres

237 Days

Reduced

$440,000

$445,000

MLS#MFRL4961656

2926 Boating Blvd
Kissimmee, FL 34746

4

3

2

3,836 SqFt

0.16 Acres

46 Days

$415,000

MLS#MFRG5108633

1718 Golfview Dr
Kissimmee, FL 34746

3

2

2

2,130 SqFt

Pool

0.18 Acres

96 Days

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28 Active Listings in The Oaks