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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

2,572 Properties Found. Page 1 of 54.
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 #S5103046

Simpson Road

$6,250,000
KISSIMMEE
MLS® # S5103046
21 Acres
Photo of Listing #S4820510

West Vine Street

$4,900,000
KISSIMMEE
MLS® # S4820510
Photo of Listing #L4943863
Reduced 11.2%

Twilight Trail

$4,885,000
KISSIMMEE
MLS® # L4943863
10 Acres
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 #O6204727
KISSIMMEE
MLS® # O6204727
11 Acres
Photo of Listing #O6170952
Reduced 4.9%

N/A

$3,900,000
KISSIMMEE
MLS® # O6170952
11,496 Sf
Photo of Listing #O6164185
Reduced 22.4%
KISSIMMEE
MLS® # O6164185
12,524 Sf
Photo of Listing #O6143511
KISSIMMEE
MLS® # O6143511
Photo of Listing #O6143696
KISSIMMEE
MLS® # O6143696
4 Acres
Photo of Listing #O5918414
KISSIMMEE
MLS® # O5918414
3 Acres
Photo of Listing #O6181188
KISSIMMEE
MLS® # O6181188
6 Beds, 6 Baths, 4,692 Sf
Photo of Listing #O6191843
Reduced 5%

249 Auburn Avenue

$2,850,000
KISSIMMEE
MLS® # O6191843
12 Beds, 13 Baths, 6,351 Sf
Photo of Listing #O6181997
KISSIMMEE
MLS® # O6181997
7,200 Sf
Photo of Listing #S5101169
Reduced 6.8%
KISSIMMEE
MLS® # S5101169
18 Beds, 12 Baths, 5,970 Sf
Photo of Listing #S5102884

510 Golfpark Drive

$2,659,000
KISSIMMEE
MLS® # S5102884
6 Beds, 6 Baths, 5,547 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 #O6189236
KISSIMMEE
MLS® # O6189236
8 Beds, 10 Baths, 5,590 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 #O6156227

8398 Happy Trail

$2,295,000
KISSIMMEE
MLS® # O6156227
4 Beds, 4 Baths, 3,667 Sf
Photo of Listing #O6205279
New

Dyer Boulevard

$2,250,000
KISSIMMEE
MLS® # O6205279
2 Acres
Photo of Listing #O6140238
Reduced 0.4%
KISSIMMEE
MLS® # O6140238
9 Beds, 9 Baths, 4,590 Sf
Photo of Listing #O6157530
Reduced 15.4%

2700 Myers Road

$2,200,000
KISSIMMEE
MLS® # O6157530
5 Acres
Photo of Listing #O6194986
Reduced 8.9%
KISSIMMEE
MLS® # O6194986
6 Beds, 8 Baths, 5,250 Sf
Photo of Listing #S5104788

Laurel Avenue

$2,000,000
KISSIMMEE
MLS® # S5104788
45 Acres
Photo of Listing #O6168676
Reduced 20%

N/A

$2,000,000
KISSIMMEE
MLS® # O6168676
Photo of Listing #S5095722
Reduced 0.1%
KISSIMMEE
MLS® # S5095722
9 Beds, 10 Baths, 5,838 Sf
Photo of Listing #O6178310
Reduced 13.1%
KISSIMMEE
MLS® # O6178310
Photo of Listing #O6154550

Pleasant Hill Road

$1,950,000
KISSIMMEE
MLS® # O6154550
1 Acres
Photo of Listing #O6176550
KISSIMMEE
MLS® # O6176550
8 Beds, 11 Baths, 4,518 Sf
Photo of Listing #O6203542
KISSIMMEE
MLS® # O6203542
6 Beds, 6 Baths, 4,737 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 #O6197876
Reduced 4.7%
KISSIMMEE
MLS® # O6197876
5 Beds, 6 Baths, 4,466 Sf
Photo of Listing #O6171090
KISSIMMEE
MLS® # O6171090
13 Beds, 13 Baths, 6,351 Sf
Photo of Listing #S5098141
KISSIMMEE
MLS® # S5098141
5 Beds, 4 Baths, 3,685 Sf
Photo of Listing #O6184685

7661 Fairfax Drive

$1,745,000
KISSIMMEE
MLS® # O6184685
12 Beds, 13 Baths, 6,351 Sf
Photo of Listing #O6134483
Reduced 0.3%
KISSIMMEE
MLS® # O6134483
4 Beds, 5 Baths, 4,195 Sf
Photo of Listing #S5083443
Reduced 6.8%

414 Church St

$1,700,000
KISSIMMEE
MLS® # S5083443
9 Beds, 9 Baths, 4,400 Sf
Photo of Listing #S5086571

2409 Shanti Drive

$1,700,000
KISSIMMEE
MLS® # S5086571
15 Beds, 17 Baths, 6,249 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 May 23rd, 2024 at 6:05pm EDT.