Lakeside Kissimmee

Lakeside is a community of single family homes, condos, and townhomes in Kissimmee, Florida, with a range of options priced between $200,000 and $597,000. There are currently a total of 28 homes for sale in Lakeside. The smallest Lakeside home presently available is a three bedroom two bathroom residence that is 1,314 square feet (1,059SF Under Air living space), and the largest of the Lakeside homes currently on the market has five beds and three baths and is a 5,009 square foot (2,767SF 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 Lakeside range from $207 to $342 and $351 for a Lakeside condo and $216 to $650 for a townhome. This fee includes common area maintenance, grounds maintenance, building maintenance, maintaining the community roads, roof repair and replacement, and the community pool. Also included is security, a 24-hour guard, real estate taxes for common areas, property insurance, 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 Lakeside home.

Lakeside amenities include a clubhouse, and swimming pool. Sports facilities include a championship golf course, tennis courts, and basketball court. There is also a community park, a playground, as well as walking or jogging trails.

The Lakeside 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 Lakeside - Kissimmee Gateway (ISM), which is five miles away; Orlando International (MCO), which is nine miles away; Orlando Executive (ORL), which is sixteen miles away, and Orlando Sanford International (SFB), which is 33 miles away from Lakeside.

Lakeside real estate activity on the Kissimmee MLS during the past year (as of November 2025) reflects 69 homes changing hands, with an average asking price of $346,735 and an average selling price of $343,412. This represents a healthy list-to-sell price ratio of 99% and $165 per square foot. During this period, Lakeside homes for sale have taken an average of 70 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 Lakeside are selling quickly. Set up a new listing alert, and we will notify you immediately when a new home in Lakeside 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.

Lakeside Homes For Sale

$597,000

MLS#MFRS5132964

2207 Mallard Creek Cir
Kissimmee, FL 34743

5

3

2

3,197 SqFt

Pool

0.14 Acres

25 Days

Under Contract

$465,000

MLS#MFRO6339579

2300 Gull Ct
Kissimmee, FL 34743

5

4

2

2,560 SqFt

Pool

0.2 Acres

74 Days

Reduced

$399,900

$414,900

MLS#MFRO6323430

2262 Stonehedge Loop
Kissimmee, FL 34743

3

3

2

2,442 SqFt

0.18 Acres

132 Days

Reduced

$399,000

$419,900

MLS#MFRO6317300

2421 Queenswood Cir
Kissimmee, FL 34743

3

2

2

1,925 SqFt

Pool

Water Front

0.21 Acres

148 Days

$399,000

MLS#MFRS5133020

2419 Lancashire Ln
Kissimmee, FL 34743

4

2

2

2,103 SqFt

0.16 Acres

81 Days

Reduced

$399,000

$420,000

MLS#MFRO6308894

2376 Flamingo Lakes Dr
Kissimmee, FL 34743

3

2

1

2,158 SqFt

Pool

0.22 Acres

180 Days

Under Contract

$394,990

$409,990

MLS#MFRS5136604

2304 Lily Pad Ln
Kissimmee, FL 34743

4

2

2

2,371 SqFt

Pool

0.16 Acres

26 Days

$390,000

MLS#MFRS5135550

1800 Baguettte Ct
Kissimmee, FL 34743

4

2

2

2,400 SqFt

0.19 Acres

44 Days

$390,000

MLS#MFRO6344933

2472 Winfield Dr
Kissimmee, FL 34743

4

2

2

2,677 SqFt

Pool

0.18 Acres

53 Days

$388,000

MLS#MFRS5134463

2182 Mallard Creek Cir
Kissimmee, FL 34743

3

2

2

5,009 SqFt

Pool

0.12 Acres

60 Days

Under Contract

$380,000

MLS#MFRS5136124

2263 Mallard Creek Cir
Kissimmee, FL 34743

4

3

2

2,562 SqFt

Pool

0.12 Acres

32 Days

$375,000

MLS#MFRO6306570

2108 Shannon Lakes Blvd
Kissimmee, FL 34743

4

2

2

1,842 SqFt

0.17 Acres

185 Days

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28 Active Listings in Lakeside