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 $465,000. There are currently a total of 27 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 5,184 square foot (2,083SF 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 $28 to $338 and $351 for a Lakeside condos 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 September 2025) reflects 69 homes changing hands, with an average asking price of $346,370 and an average selling price of $342,609. 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 64 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

Under Contract

$465,000

MLS#MFRO6339579

2300 Gull Ct
Kissimmee, FL 34743

5

4

2

2,560 SqFt

Pool

0.2 Acres

28 Days

Reduced

$410,000

$420,000

MLS#MFRO6308894

2376 Flamingo Lakes Dr
Kissimmee, FL 34743

3

2

1

2,158 SqFt

Pool

0.22 Acres

134 Days

Reduced

$409,900

$414,900

MLS#MFRO6323430

2262 Stonehedge Loop
Kissimmee, FL 34743

3

3

2

2,442 SqFt

0.18 Acres

86 Days

Reduced

$409,000

$419,900

MLS#MFRO6317300

2421 Queenswood Cir
Kissimmee, FL 34743

3

2

2

1,925 SqFt

Pool

Water Front

0.21 Acres

102 Days

Reduced

$399,900

$425,000

MLS#MFRO6312549

2506 Shelby Cir
Kissimmee, FL 34743

3

2

2

2,202 SqFt

0.15 Acres

122 Days

$399,000

MLS#MFRS5134995

2300 Saphire Ct
Kissimmee, FL 34743

3

2

2

1,862 SqFt

0.24 Acres

3 Days

$399,000

MLS#MFRS5133020

2419 Lancashire Ln
Kissimmee, FL 34743

4

2

2

2,103 SqFt

0.16 Acres

35 Days

Under Contract

$390,000

MLS#MFRO6344933

2472 Winfield Dr
Kissimmee, FL 34743

3

2

2

2,677 SqFt

Pool

0.18 Acres

7 Days

$388,000

MLS#MFRS5134463

2182 Mallard Creek Cir
Kissimmee, FL 34743

3

2

2

5,009 SqFt

Pool

0.12 Acres

14 Days

$375,000

MLS#MFRO6306570

2108 Shannon Lakes Blvd
Kissimmee, FL 34743

4

2

2

1,842 SqFt

0.17 Acres

139 Days

Reduced

$374,990

$389,990

MLS#MFRS5124446

2049 Shannon Lakes Blvd
Kissimmee, FL 34743

3

2

2

1,674 SqFt

Pool

0.13 Acres

149 Days

$374,900

MLS#MFRO6326899

2113 Broome St
Kissimmee, FL 34743

3

3

2

1,956 SqFt

0.02 Acres

73 Days

New Construction

You may also be interested in Lakeside in Tamarac, Lakeside in Miami, Lakeside in Naples, Lakeside in Hudson, Lakeside in Apopka, Lakeside in Tavares, Lakeside in Riverview, Lakeside in Lauderdale Lakes or Lakeside in Stuart.

27 Active Listings in Lakeside