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

701 Properties Found. Page 1 of 15.
Photo of Listing #S5015482

3098 Will Hughey Rd

$10,000,000
Kissimmee
MLS® # S5015482
11 Acres
Photo of Listing #S4832428
Kissimmee
MLS® # S4832428
48,962 Sf
Photo of Listing #O5898603

8590 Apache Trl

$5,000,000
Kissimmee
MLS® # O5898603
5 Beds, 9 Baths, 11,138 Sf
Photo of Listing #P4914773

Goodman

$4,500,000
Kissimmee
MLS® # P4914773
68 Acres
Photo of Listing #S4667762
Kissimmee
MLS® # S4667762
37,000 Sf
Photo of Listing #S5043981

N Poinciana Blvd

$4,000,000
Kissimmee
MLS® # S5043981
8 Acres
Photo of Listing #O5560748

Captain Kidd Blvd

$3,500,000
Kissimmee
MLS® # O5560748
17 Acres
Photo of Listing #O5897853
Reduced 31.3%

Ham Brown Rd

$3,300,000
Kissimmee
MLS® # O5897853
20 Acres
Photo of Listing #S5048790
Kissimmee
MLS® # S5048790
12,496 Sf
Photo of Listing #O5918414
Reduced 9.4%
Kissimmee
MLS® # O5918414
3 Acres
Photo of Listing #S5046026
Kissimmee
MLS® # S5046026
3 Acres
Photo of Listing #O5915225
Kissimmee
MLS® # O5915225
17,400 Sf
Photo of Listing #S5036295
Reduced 8%

4441 Anderson Rd

$2,300,000
Kissimmee
MLS® # S5036295
3 Beds, 2 Baths, 1,608 Sf
Photo of Listing #O5854329

1714 Louis Dr

$2,275,000
Kissimmee
MLS® # O5854329
8 Acres
Photo of Listing #O5911912
Kissimmee
MLS® # O5911912
6 Beds, 6 Baths, 5,667 Sf
Photo of Listing #S5031594

4421 Reaves Rd

$2,200,000
Kissimmee
MLS® # S5031594
5 Beds, 6 Baths, 5,044 Sf
Photo of Listing #S4820510

W Vine St

$1,999,999
Kissimmee
MLS® # S4820510
Photo of Listing #O5912022

Simpson Rd

$1,950,000
Kissimmee
MLS® # O5912022
3 Acres
Photo of Listing #O5824323
Kissimmee
MLS® # O5824323
3,426 Sf
Photo of Listing #S5026633
Kissimmee
MLS® # S5026633
2 Acres
Photo of Listing #R4904188
Kissimmee
MLS® # R4904188
7 Acres
Photo of Listing #S5009637

952 Jack Calhoun Dr

$1,700,000
Kissimmee
MLS® # S5009637
6,600 Sf
Photo of Listing #O5860608
Reduced 15.3%
Kissimmee
MLS® # O5860608
3 Acres
Photo of Listing #OM551661

Siesta Lago Dr

$1,595,000
Kissimmee
MLS® # OM551661
6 Acres
Photo of Listing #S5028716

1011 W Carroll St

$1,590,000
Kissimmee
MLS® # S5028716
3,546 Sf
Photo of Listing #S5040434

2982 Michigan Ave

$1,500,000
Kissimmee
MLS® # S5040434
6,373 Sf
Photo of Listing #O5790804
Kissimmee
MLS® # O5790804
8 Acres
Photo of Listing #S4856294

Granada Blvd

$1,500,000
Kissimmee
MLS® # S4856294
6 Acres
Photo of Listing #O5904326

907 Person St

$1,275,000
Kissimmee
MLS® # O5904326
4,041 Sf
Photo of Listing #S5048340

201 Broadway

$1,200,000
Kissimmee
MLS® # S5048340
11,975 Sf
Photo of Listing #O5916989
Kissimmee
MLS® # O5916989
14 Acres
Photo of Listing #O5935934
New

7695 Graben St

$1,190,000
Kissimmee
MLS® # O5935934
12 Beds, 13 Baths, 6,351 Sf
Photo of Listing #O5934896

7913 Jacks Club Dr

$1,162,106
Kissimmee
MLS® # O5934896
5 Beds, 6 Baths, 4,319 Sf
Photo of Listing #S4853056
Kissimmee
MLS® # S4853056
4 Acres
Photo of Listing #R4903618
Kissimmee
MLS® # R4903618
3,556 Sf
Photo of Listing #S5026587
Kissimmee
MLS® # S5026587
875 Sf
Photo of Listing #O5921371

217 Southfield St

$1,098,000
Kissimmee
MLS® # O5921371
10 Beds, 10 Baths, 5,189 Sf
Photo of Listing #O5931879

8525 Patricia Trl

$1,013,000
Kissimmee
MLS® # O5931879
6 Beds, 6 Baths, 5,157 Sf
Photo of Listing #O5931568

221 Falls Dr

$999,000
Kissimmee
MLS® # O5931568
9 Beds, 9 Baths, 4,630 Sf
Photo of Listing #S5043887

N Thacker Ave

$990,000
Kissimmee
MLS® # S5043887
2 Acres
Photo of Listing #S5048774
New
Kissimmee
MLS® # S5048774
10 Beds, 10 Baths, 4,723 Sf
Photo of Listing #P4913748

Twilight Trl

$980,000
Kissimmee
MLS® # P4913748
10 Acres
Photo of Listing #O5889316

307 Broadway

$950,000
Kissimmee
MLS® # O5889316
8,180 Sf
Photo of Listing #S5045970
Kissimmee
MLS® # S5045970
15 Beds, 15 Baths, 6,255 Sf
Photo of Listing #S5043236
Reduced 13.6%
Kissimmee
MLS® # S5043236
7 Beds, 8 Baths, 6,562 Sf
Photo of Listing #S5043153

50 Lakeview Dr

$950,000
Kissimmee
MLS® # S5043153
2 Acres
Photo of Listing #O5918509
Kissimmee
MLS® # O5918509
14 Beds, 11 Baths, 6,255 Sf
Photo of Listing #O5932499

181 Lasso Dr

$899,900
Kissimmee
MLS® # O5932499
10 Beds, 10 Baths, 4,707 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 April 13th, 2021 at 12:47pm EDT.