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 $245,000 and $783,750. There are currently a total of 32 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 (3,968SF 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 November 2025) reflects 51 homes changing hands, with an average asking price of $406,218 and an average selling price of $393,461. This represents a healthy list-to-sell price ratio of 97% and $142 per square foot. During this period, The Oaks homes for sale have taken an average of 92 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

7 Days

Reduced

$605,000

$625,000

MLS#MFRO6323394

2460 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,347 SqFt

Pool

0.28 Acres

128 Days

$584,900

MLS#MFRS5126074

1976 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,416 SqFt

Water Front

0.18 Acres

191 Days

Reduced

$579,000

$589,900

MLS#MFRO6349376

1527 Angler Ave
Kissimmee, FL 34746

5

5

2

3,607 SqFt

Water Front

0.21 Acres

37 Days

Reduced

$574,900

$589,900

MLS#MFRS5118554

3034 Boating Blvd
Kissimmee, FL 34746

4

3

2

2,927 SqFt

Pool

0.16 Acres

296 Days

Reduced

$530,000

$540,000

MLS#MFRO6319826

2530 The Oaks Blvd
Kissimmee, FL 34746

4

3

2

3,707 SqFt

Pool

0.19 Acres

144 Days

Reduced

$510,000

$535,000

MLS#MFRO6254515

2108 Drive Way
Kissimmee, FL 34746

4

3

2

3,209 SqFt

Pool

0.17 Acres

366 Days

$509,000

MLS#MFRS5134312

1516 Angler Ave
Kissimmee, FL 34746

3

3

2

3,994 SqFt

0.16 Acres

55 Days

Reduced

$499,000

$529,900

MLS#MFRO6332997

2622 Roughside Cir
Kissimmee, FL 34746

4

3

2

3,530 SqFt

Pool

0.28 Acres

97 Days

Reduced

$499,000

$550,000

MLS#MFRO6325623

2298 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,260 SqFt

Water Front

0.17 Acres

123 Days

Under Contract

$475,000

$495,000

MLS#MFRG5100687

2601 Roughside Cir
Kissimmee, FL 34746

4

3

2

3,340 SqFt

Pool

0.29 Acres

88 Days

$460,000

MLS#MFRO6336847

2200 The Oaks Blvd
Kissimmee, FL 34746

4

4

2

3,356 SqFt

Pool

0.19 Acres

83 Days

You may also be interested in The Oaks in Boca Raton, The Oaks in Hobe Sound, The Oaks in Jupiter, The Oaks in Sanford, The Oaks in Land O Lakes, The Oaks in Tampa, The Oaks in Palm City, The Oaks in Thonotosassa, The Oaks in Bradenton, The Oaks in Lakeland or The Oaks in Melbourne.

32 Active Listings in The Oaks