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Kissimmee Florida

This lovely town in Osceola County, Florida, is known for its proximity to the Kissimmee Chain of Lakes, a beautiful area with many lakes of different sizes that are all connected by meandering creeks and canals. This spot is very popular with tourists who love the out-of-doors; however, it is also close to the ever-popular Walt Disney World and the world-class city of Orlando.

Interested in purchasing a vacation home in the Kissimmee area?
Please visit our Orlando Vacation Homes

Kissimmee Homes for Sale

2,236 Properties Found. Page 1 of 47.
Photo of Listing #S5093408

2211 West Vine Street

$15,500,000
KISSIMMEE
MLS® # S5093408
144,332 Sf
Photo of Listing #S5085096
Reduced 31.5%
KISSIMMEE
MLS® # S5085096
29 Acres
Photo of Listing #O6158900
KISSIMMEE
MLS® # O6158900
8 Acres
Photo of Listing #O6158891
KISSIMMEE
MLS® # O6158891
4,400 Sf
Photo of Listing #S5085102
Reduced 61.5%
KISSIMMEE
MLS® # S5085102
41 Acres
Photo of Listing #S5098426

2231 Fortune Road

$6,500,000
KISSIMMEE
MLS® # S5098426
9,000 Sf
Photo of Listing #L4934618

Twilight Trail

$5,500,000
KISSIMMEE
MLS® # L4934618
10 Acres
Photo of Listing #S5093535
Reduced 33.3%

2275 Fortune Road

$5,000,000
KISSIMMEE
MLS® # S5093535
28,924 Sf
Photo of Listing #S4820510

West Vine Street

$4,900,000
KISSIMMEE
MLS® # S4820510
Photo of Listing #R4905868

South Goodman Road

$4,800,000
KISSIMMEE
MLS® # R4905868
17 Acres
Photo of Listing #O6118276

4441 Anderson Road

$4,500,000
KISSIMMEE
MLS® # O6118276
3,948 Sf
Photo of Listing #O6170952

N/A

$4,100,000
KISSIMMEE
MLS® # O6170952
11,496 Sf
Photo of Listing #O6164185
Reduced 22.4%
KISSIMMEE
MLS® # O6164185
12,524 Sf
Photo of Listing #O6153717
KISSIMMEE
MLS® # O6153717
5,777 Sf
Photo of Listing #O6143511
KISSIMMEE
MLS® # O6143511
Photo of Listing #O6143696
KISSIMMEE
MLS® # O6143696
4 Acres
Photo of Listing #O6157530

2700 Myers Road

$3,200,000
KISSIMMEE
MLS® # O6157530
5 Acres
Photo of Listing #O5918414
KISSIMMEE
MLS® # O5918414
3 Acres
Photo of Listing #S5100558
KISSIMMEE
MLS® # S5100558
10,462 Sf
Photo of Listing #O5942296
KISSIMMEE
MLS® # O5942296
3 Acres
Photo of Listing #O6181188
KISSIMMEE
MLS® # O6181188
6 Beds, 6 Baths, 4,692 Sf
Photo of Listing #S5101169
New
KISSIMMEE
MLS® # S5101169
18 Beds, 12 Baths, 5,970 Sf
Photo of Listing #O6181997
KISSIMMEE
MLS® # O6181997
7,200 Sf
Photo of Listing #O6116897
Reduced 12.5%
KISSIMMEE
MLS® # O6116897
11,005 Sf
Photo of Listing #O6104903

907 Person Street

$2,500,000
KISSIMMEE
MLS® # O6104903
1,619 Sf
Photo of Listing #R4906147
Reduced 13.8%

Old Vineland Road

$2,500,000
KISSIMMEE
MLS® # R4906147
14 Acres
Photo of Listing #O6066876
Reduced 14.9%
KISSIMMEE
MLS® # O6066876
8 Beds, 10 Baths, 5,590 Sf
Photo of Listing #S5095722
KISSIMMEE
MLS® # S5095722
9 Beds, 10 Baths, 5,838 Sf
Photo of Listing #S5072743
Reduced 2%
KISSIMMEE
MLS® # S5072743
7 Acres
Photo of Listing #O6181815
KISSIMMEE
MLS® # O6181815
5 Beds, 6 Baths, 4,319 Sf
Photo of Listing #O6170009
KISSIMMEE
MLS® # O6170009
6 Beds, 7 Baths, 4,385 Sf
Photo of Listing #O6156227

8398 Happy Trail

$2,295,000
KISSIMMEE
MLS® # O6156227
4 Beds, 4 Baths, 3,667 Sf
Photo of Listing #O6140238
Reduced 5.9%
KISSIMMEE
MLS® # O6140238
9 Beds, 9 Baths, 4,590 Sf
Photo of Listing #S5098354

N John Young Pkwy

$2,200,000
KISSIMMEE
MLS® # S5098354
5 Acres
Photo of Listing #O6168676
Reduced 20%

N/A

$2,000,000
KISSIMMEE
MLS® # O6168676
Photo of Listing #O6178310
Reduced 13.1%
KISSIMMEE
MLS® # O6178310
Photo of Listing #S5092621
KISSIMMEE
MLS® # S5092621
1,296 Sf
Photo of Listing #S5065177
Reduced 11.3%
KISSIMMEE
MLS® # S5065177
Photo of Listing #O6154550

Pleasant Hill Road

$1,950,000
KISSIMMEE
MLS® # O6154550
1 Acres
Photo of Listing #O6100191
Reduced 0.1%
KISSIMMEE
MLS® # O6100191
10 Beds, 10 Baths, 5,546 Sf
Photo of Listing #S5100179

168 Bowie Lane

$1,927,000
KISSIMMEE
MLS® # S5100179
7,411 Sf
Photo of Listing #S5100164

168 Bowie Lane

$1,927,000
KISSIMMEE
MLS® # S5100164
7,411 Sf
Photo of Listing #O6187856
New

222 Pawnee Trail

$1,900,000
KISSIMMEE
MLS® # O6187856
3 Beds, 5 Baths, 6,559 Sf
Photo of Listing #O6113358

1300 Garden Street

$1,900,000
KISSIMMEE
MLS® # O6113358
4,000 Sf
Photo of Listing #O6176550
KISSIMMEE
MLS® # O6176550
8 Beds, 11 Baths, 4,518 Sf
Photo of Listing #S5100473
KISSIMMEE
MLS® # S5100473
6,550 Sf
Photo of Listing #O6134478
Reduced 0.5%
KISSIMMEE
MLS® # O6134478
5 Beds, 8 Baths, 4,582 Sf
Photo of Listing #O6139323
Reduced 3.7%

8097 Surf Street

$1,825,000
KISSIMMEE
MLS® # O6139323
8 Beds, 11 Baths, 4,092 Sf

One big draw for Kissimmee is that it is a popular place to stay for tourists, and there are a lot of people who buy homes in the town and rent them to other vacationers when they are back at home. These vacation home sales are making the Kissimmee real estate scene shimmer with activity because many who would not be able to afford a vacation home under normal circumstances can now have one in one of the country’s most beautiful natural areas.

Because of the tourist draw, the restaurants and shopping in Kissimmee are also well above average. There are over 100 hotels, and the dining needs to be top-notch to serve so many visitors—and it is. Also, new developments are being planned constantly in the town as well as the Chain of Lakes regions. People looking for investment properties and vacation homes can find affordable and beautiful surroundings in Kissimmee.

Even with all the development, Kissimmee home prices are staying attractive and steady. Whether a newcomer is buying a personal residence or vacation home, this little town has much to offer including great prices. However, it won’t last long, so when you think about relocating to Florida, check Kissimmee first.

All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified.

Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Listing data comes from My Florida Regional MLS DBA Stellar MLS.

Listing information last updated on March 19th, 2024 at 9:50am EDT.