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

1,179 Properties Found. Page 1 of 25.
Photo of Listing #S5066790

15525 West Space

$15,500,000
KISSIMMEE
MLS® # S5066790
15 Acres
Photo of Listing #S5061897

Ernest Street

$9,900,000
KISSIMMEE
MLS® # S5061897
33 Acres
Photo of Listing #S4667762
KISSIMMEE
MLS® # S4667762
37,000 Sf
Photo of Listing #O6018108
Reduced 4.4%
KISSIMMEE
MLS® # O6018108
8 Beds, 12 Baths, 9,558 Sf
Photo of Listing #S5069652

N/A

$5,400,000
KISSIMMEE
MLS® # S5069652
17,728 Sf
Photo of Listing #S4820510

West Vine Street

$4,900,000
KISSIMMEE
MLS® # S4820510
Photo of Listing #O6038617
New

4441 Anderson Road

$3,800,000
KISSIMMEE
MLS® # O6038617
12 Acres
Photo of Listing #O6034537

Sand Hill Road

$3,750,000
KISSIMMEE
MLS® # O6034537
6 Acres
Photo of Listing #S5068866
KISSIMMEE
MLS® # S5068866
10 Acres
Photo of Listing #O6015144

2481 Ham Brown Road

$3,500,000
KISSIMMEE
MLS® # O6015144
3 Beds, 2 Baths, 2,800 Sf
Photo of Listing #O6015156

2481 Ham Brown Road

$3,500,000
KISSIMMEE
MLS® # O6015156
16 Acres
Photo of Listing #S5069662
New
KISSIMMEE
MLS® # S5069662
15,044 Sf
Photo of Listing #O6019853
KISSIMMEE
MLS® # O6019853
8 Beds, 10 Baths, 5,720 Sf
Photo of Listing #U8147259
KISSIMMEE
MLS® # U8147259
8 Acres
Photo of Listing #O5978209
Reduced 61.8%
KISSIMMEE
MLS® # O5978209
44,820 Sf
Photo of Listing #R4904813
Reduced 4.7%

1511 Simmons Road

$2,850,000
KISSIMMEE
MLS® # R4904813
1,387 Sf
Photo of Listing #O5942296
KISSIMMEE
MLS® # O5942296
3 Acres
Photo of Listing #O6032100
KISSIMMEE
MLS® # O6032100
7,284 Sf
Photo of Listing #S5065177
Reduced 7.4%
KISSIMMEE
MLS® # S5065177
Photo of Listing #S5031594

4421 Reaves Road

$2,200,000
KISSIMMEE
MLS® # S5031594
5 Beds, 6 Baths, 5,044 Sf
Photo of Listing #S5066465
KISSIMMEE
MLS® # S5066465
6 Beds, 6 Baths, 4,673 Sf
Photo of Listing #O6017418
Reduced 5.4%
KISSIMMEE
MLS® # O6017418
5 Beds, 5 Baths, 3,578 Sf
Photo of Listing #S5068312

1439 Simmons Road

$1,662,000
KISSIMMEE
MLS® # S5068312
3 Beds, 3 Baths, 3,101 Sf
Photo of Listing #O6017827
Reduced 4.6%

8097 Surf Street

$1,620,000
KISSIMMEE
MLS® # O6017827
8 Beds, 11 Baths, 4,092 Sf
Photo of Listing #S5063916
KISSIMMEE
MLS® # S5063916
5 Acres
Photo of Listing #S5070192
New
KISSIMMEE
MLS® # S5070192
2,576 Sf
Photo of Listing #S5070183
New
KISSIMMEE
MLS® # S5070183
2,576 Sf
Photo of Listing #O6017163

50 Lakeview Drive

$1,500,000
KISSIMMEE
MLS® # O6017163
2 Acres
Photo of Listing #O6015808
KISSIMMEE
MLS® # O6015808
4 Beds, 3 Baths, 4,292 Sf
Photo of Listing #O6014367
KISSIMMEE
MLS® # O6014367
1,132 Sf
Photo of Listing #O6014248
KISSIMMEE
MLS® # O6014248
2 Acres
Photo of Listing #S4856294

Granada Boulevard

$1,500,000
KISSIMMEE
MLS® # S4856294
6 Acres
Photo of Listing #O5932800

Armstrong Boulevard

$1,500,000
KISSIMMEE
MLS® # O5932800
7,500 Sf
Photo of Listing #O5952176

1126 Watson Court

$1,499,900
KISSIMMEE
MLS® # O5952176
8 Beds, 8 Baths, 4,606 Sf
Photo of Listing #O6025413
KISSIMMEE
MLS® # O6025413
4 Beds, 2 Baths, 2,320 Sf
Photo of Listing #O6019067
KISSIMMEE
MLS® # O6019067
5,394 Sf
Photo of Listing #S5064781
Reduced 0.1%

3811 Bowfin Trail

$1,369,000
KISSIMMEE
MLS® # S5064781
6 Beds, 4 Baths, 4,565 Sf
Photo of Listing #O6036096
KISSIMMEE
MLS® # O6036096
8 Beds, 5 Baths, 4,289 Sf
Photo of Listing #O6033542
KISSIMMEE
MLS® # O6033542
10 Beds, 10 Baths, 4,723 Sf
Photo of Listing #S5069594
New

7725 Fairfax Drive

$1,299,000
KISSIMMEE
MLS® # S5069594
11 Beds, 12 Baths, 5,496 Sf
Photo of Listing #S5069336
Reduced 4.4%
KISSIMMEE
MLS® # S5069336
10 Beds, 10 Baths, 4,650 Sf
Photo of Listing #S5057806
Reduced 13.8%

1800 Palmetto Drive

$1,250,000
KISSIMMEE
MLS® # S5057806
3,970 Sf
Photo of Listing #O6030284
KISSIMMEE
MLS® # O6030284
4 Beds, 2 Baths, 3,300 Sf
Photo of Listing #O6016598

Westside Boulevard

$1,200,000
KISSIMMEE
MLS® # O6016598
5 Acres
Photo of Listing #S5051861
KISSIMMEE
MLS® # S5051861
5 Acres
Photo of Listing #O6031550

7708 Fairfax Drive

$1,150,000
KISSIMMEE
MLS® # O6031550
8 Beds, 9 Baths, 4,630 Sf
Photo of Listing #O6022802
Reduced 4.3%

261 Falls Drive

$1,149,000
KISSIMMEE
MLS® # O6022802
9 Beds, 9 Baths, 4,630 Sf
Photo of Listing #S5064818
Reduced 2.1%

8331 Choctaw Trail

$1,125,000
KISSIMMEE
MLS® # S5064818
5 Beds, 3 Baths, 3,258 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 June 29th, 2022 at 9:19am EDT.