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 $450,000. There are currently a total of 32 homes for sale in Lakeside. The smallest Lakeside home presently available is a three bedroom two bathroom residence that is 1,090 square feet (1,000SF Under Air living space), and the largest of the Lakeside homes currently on the market has four beds and three baths and is a 5,097 square foot (1,824SF 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 $20 to $342 and $351 for a Lakeside condo. 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 March 2026) reflects 59 homes changing hands, with an average asking price of $358,017 and an average selling price of $350,972. This represents a healthy list-to-sell price ratio of 98% and $159 per square foot. During this period, Lakeside homes for sale have taken an average of 67 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

$404,900

$414,900

MLS#MFRS5144236

2400 Winchester Blvd
Kissimmee, FL 34743

3

2

2

1,845 SqFt

0.26 Acres

36 Days

$398,900

MLS#MFRO6377132

2426 Timothy Ln
Kissimmee, FL 34743

4

3

2

2,364 SqFt

0.19 Acres

59 Days

Reduced

$389,900

$420,000

MLS#MFRO6308894

2376 Flamingo Lakes Dr
Kissimmee, FL 34743

3

2

1

2,158 SqFt

Pool

0.22 Acres

317 Days

Under Contract

$380,000

MLS#MFRS5142485

2450 Shelby Cir
Kissimmee, FL 34743

3

2

2

2,358 SqFt

0.13 Acres

60 Days

Reduced

$378,000

$399,900

MLS#MFRR4910312

2416 Morgan Point Blvd
Kissimmee, FL 34743

3

2

2

1,911 SqFt

Pool

0.18 Acres

117 Days

Reduced

$375,000

$388,000

MLS#MFRS5134463

2182 Mallard Creek Cir
Kissimmee, FL 34743

3

2

2

5,009 SqFt

Pool

0.12 Acres

197 Days

$359,900

MLS#MFRO6384641

2103 Derringer Ct
Kissimmee, FL 34743

3

2

2

2,560 SqFt

0.12 Acres

15 Days

$357,888

MLS#MFRS5143818

2346 Lily Pad Ln
Kissimmee, FL 34743

3

2

2

2,171 SqFt

0.12 Acres

25 Days

$355,000

MLS#MFRR4910839

2405 Lincolnshire Ct
Kissimmee, FL 34743

3

2

2

1,840 SqFt

0.15 Acres

21 Days

Under Contract

$354,900

$384,900

MLS#MFRO6322093

2149 Mallard Creek Cir
Kissimmee, FL 34743

4

2

2

2,400 SqFt

Water Front

0.2 Acres

272 Days

Reduced

$350,000

$375,000

MLS#MFRO6318455

2041 Lacie Jo Ln
Kissimmee, FL 34743

3

3

1

2,197 SqFt

0.11 Acres

283 Days

$349,990

MLS#MFRO6389540

2426 Black Powder Ln
Kissimmee, FL 34743

3

2

2

2,352 SqFt

0.12 Acres

15 Days

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.

32 Active Listings in Lakeside