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 $220,000 and $615,000. There are currently a total of 38 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 five beds and four baths and is a 4,416 square foot (3,592SF 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 condos 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 September 2025) reflects 50 homes changing hands, with an average asking price of $409,040 and an average selling price of $397,548. This represents a healthy list-to-sell price ratio of 97% and $144 per square foot. During this period, The Oaks homes for sale have taken an average of 87 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

Reduced

$615,000

$625,000

MLS#MFRO6323394

2460 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,347 SqFt

Pool

0.28 Acres

83 Days

Reduced

$590,000

$619,000

MLS#MFRO6286887

3039 Boating Blvd. Blvd
Kissimmee, FL 34746

5

4

3

4,263 SqFt

Pool

Water Front

0.18 Acres

204 Days

$584,900

MLS#MFRS5126074

1976 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,416 SqFt

Water Front

0.18 Acres

146 Days

Reduced

$574,900

$589,900

MLS#MFRS5118554

3034 Boating Blvd
Kissimmee, FL 34746

4

3

2

2,927 SqFt

Pool

0.16 Acres

251 Days

Reduced

$565,000

$590,000

MLS#MFRO6326305

1758 Boat Launch Rd
Kissimmee, FL 34746

3

3

3

3,536 SqFt

Pool

Water Front

0.26 Acres

76 Days

Reduced

$535,000

$550,000

MLS#MFRO6305715

2803 Boating Blvd
Kissimmee, FL 34746

5

5

2

3,837 SqFt

Pool

Water Front

0.18 Acres

143 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

99 Days

Reduced

$525,000

$550,000

MLS#MFRO6325623

2298 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,260 SqFt

Water Front

0.17 Acres

78 Days

Reduced

$510,000

$535,000

MLS#MFRO6254515

2108 Drive Way
Kissimmee, FL 34746

4

3

2

3,209 SqFt

Pool

0.17 Acres

321 Days

$509,000

MLS#MFRS5134312

1516 Angler Ave
Kissimmee, FL 34746

3

3

2

3,994 SqFt

0.16 Acres

10 Days

Reduced

$499,000

$529,900

MLS#MFRO6332997

2622 Roughside Cir
Kissimmee, FL 34746

4

3

2

3,530 SqFt

Pool

0.28 Acres

52 Days

Under Contract

$480,000

$600,000

MLS#MFRO6283348

2260 The Oaks Blvd
Kissimmee, FL 34746

5

4

2

4,407 SqFt

Pool

0.16 Acres

216 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 or The Oaks in Bradenton.

38 Active Listings in The Oaks