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 $200,000 and $824,900. There are currently a total of 37 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 $529 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 May 2026) reflects 51 homes changing hands, with an average asking price of $417,373 and an average selling price of $407,745. This represents a healthy list-to-sell price ratio of 98% and $136 per square foot. During this period, The Oaks homes for sale have taken an average of 107 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

$812,900

$824,900

MLS#MFRO6395237

2120 Bunker View Ct
Kissimmee, FL 34746

5

4

4,580 SqFt

Water Front

0.36 Acres

39 Days

$688,999

MLS#MFRS5146993

2987 Boating Blvd
Kissimmee, FL 34746

4

4

2

4,084 SqFt

Pool

0.16 Acres

38 Days

$670,000

MLS#AX-11994713

1754 Boat Launch Rd
Kissimmee, FL 34746

4

3

3

3,513 SqFt

Water Front

0.204 Acres

37 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

105 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

309 Days

Under Contract

$594,800

$624,990

MLS#MFRO6366323

1563 Angler Ave
Kissimmee, FL 34746

6

4

2

4,984 SqFt

0.24 Acres

149 Days

Reduced

$539,900

$575,000

MLS#MFRO6371236

1524 The Oaks Blvd
Kissimmee, FL 34746

4

3

2

3,488 SqFt

Pool

0.18 Acres

121 Days

Reduced

$535,000

$569,000

MLS#MFRO6361402

2165 The Oaks Blvd
Kissimmee, FL 34746

4

4

2

3,357 SqFt

0.18 Acres

172 Days

Reduced

$520,000

$525,000

MLS#MFRS5142892

2617 Teeside Ct
Kissimmee, FL 34746

3

4

3

3,979 SqFt

Pool

0.25 Acres

97 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

178 Days

Under Contract

$499,000

$529,900

MLS#MFRO6332997

2622 Roughside Cir
Kissimmee, FL 34746

4

3

2

3,530 SqFt

Pool

0.28 Acres

278 Days

Reduced

$489,450

$525,000

MLS#MFRO6363370

1822 Trophy Bass Way
Kissimmee, FL 34746

4

3

3

3,770 SqFt

Water Front

0.22 Acres

164 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, The Oaks in Melbourne, The Oaks in Cape Canaveral, The Oaks in Port Charlotte, The Oaks in Oakland Park or The Oaks in Davie.

37 Active Listings in The Oaks