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

Reduced 4.1%

116 Alcala Drive

$278,000

KISSIMMEE

MLS® # S5103237

3 Beds, 2 Baths, 1,525 Sf

Reduced 3.8%

2615 West Doris Street

$278,000

KISSIMMEE

MLS® # S5102636

2 Beds, 1 Baths, 976 Sf

4015 Venetian Bay Drive 106

$278,000

KISSIMMEE

MLS® # S5101781

3 Beds, 2 Baths, 1,296 Sf

Reduced 2.6%

8425 Crystal Cove Loop

$277,500

KISSIMMEE

MLS® # L4941141

3 Beds, 3 Baths, 1,291 Sf

Reduced 0.7%

3163 Britannia Boulevard C

$277,500

KISSIMMEE

MLS® # O6158911

3 Beds, 3 Baths, 1,434 Sf

Reduced 3.8%

2222 San Vittorino Circle 104

$277,000

KISSIMMEE

MLS® # S5094838

3 Beds, 2 Baths, 1,296 Sf

New

1298 Clove Drive

$275,000

KISSIMMEE

MLS® # A4609343

3 Beds, 3 Baths, 1,978 Sf

237 Royal Palm Drive

$275,000

KISSIMMEE

MLS® # S5103860

3 Beds, 2 Baths, 1,172 Sf

3015 Bonfire Beach Drive 202

$275,000

KISSIMMEE

MLS® # OM676877

2 Beds, 2 Baths, 1,271 Sf

2260 San Vital Drive 106

$275,000

KISSIMMEE

MLS® # S5103160

3 Beds, 2 Baths, 1,296 Sf

8834 Dunes Court 304

$275,000

KISSIMMEE

MLS® # O6195630

3 Beds, 2 Baths, 1,249 Sf

Reduced 4.8%

9051 Treasure Trove Lane 505

$275,000

KISSIMMEE

MLS® # O6192250

3 Beds, 2 Baths, 1,700 Sf

3321 Whitestone Circle 201

$275,000

KISSIMMEE

MLS® # S5101120

3 Beds, 2 Baths, 1,495 Sf

3143 Britannia Boulevard A

$275,000

KISSIMMEE

MLS® # S5100271

3 Beds, 2 Baths, 1,357 Sf

Reduced 5.1%

918 Cannes Drive

$275,000

KISSIMMEE

MLS® # S5098431

3 Beds, 2 Baths, 1,284 Sf

3060 Pirates Retreat Court 406

$275,000

KISSIMMEE

MLS® # O6171403

3 Beds, 2 Baths, 1,700 Sf

Reduced 1.8%

1043 Park Ridge Circle

$275,000

KISSIMMEE

MLS® # S5097735

3 Beds, 3 Baths, 1,291 Sf

Reduced 1.8%

2888 Tanzanite Terrace

$275,000

KISSIMMEE

MLS® # O6105996

3 Beds, 3 Baths, 1,831 Sf

Reduced 1.8%

2300 Silver Palm Drive 205

$275,000

KISSIMMEE

MLS® # O6166091

3 Beds, 2 Baths, 1,402 Sf

Reduced 3.8%

8908 Legacy Court 203

$275,000

KISSIMMEE

MLS® # O6161699

3 Beds, 2 Baths, 1,249 Sf

Reduced 3.5%

1089 Park Ridge Circle

$275,000

KISSIMMEE

MLS® # S5095361

3 Beds, 3 Baths, 1,291 Sf

Reduced 1.6%

2717 North Poinciana Boulevard 177

$275,000

KISSIMMEE

MLS® # O6159082

3 Beds, 2 Baths, 1,287 Sf

New

3366 Fallbrook Drive

$274,900

KISSIMMEE

MLS® # S5104360

2 Beds, 2 Baths, 1,353 Sf

8703 Knightsbridge Court C

$274,900

KISSIMMEE

MLS® # O6195025

3 Beds, 2 Baths, 1,357 Sf

Reduced 1.8%

9055 Treasure Trove Lane 203

$274,900

KISSIMMEE

MLS® # O6117636

3 Beds, 2 Baths, 1,700 Sf

Reduced 5.2%

2302 Silver Palm Drive 301

$274,000

KISSIMMEE

MLS® # O6158765

3 Beds, 2 Baths, 1,402 Sf

Reduced 1.1%

2000 Royal Bay Boulevard 129

$273,000

KISSIMMEE

MLS® # O6186518

3 Beds, 2 Baths, 1,350 Sf

431 Short Drive

$272,995

KISSIMMEE

MLS® # S5102798

3 Beds, 2 Baths, 1,170 Sf

Reduced 0.7%

114 Briarcliff Drive

$272,000

KISSIMMEE

MLS® # T3497992

4 Beds, 2 Baths, 1,882 Sf

Reduced 0.2%

3142 Britannia Boulevard C

$271,500

KISSIMMEE

MLS® # O6185653

3 Beds, 2 Baths, 1,357 Sf

New

207 Grouper Court

$270,000

KISSIMMEE

MLS® # O6203304

3 Beds, 2 Baths, 1,565 Sf

827 San Jose Court

$270,000

KISSIMMEE

MLS® # S5100136

3 Beds, 2 Baths, 1,524 Sf

2482 Sweetwater Club Circle 86

$270,000

KISSIMMEE

MLS® # O6196874

3 Beds, 2 Baths, 1,220 Sf

8711 Knightsbridge Court C

$270,000

KISSIMMEE

MLS® # O6195056

3 Beds, 2 Baths, 1,381 Sf

1604 Peach Street

$270,000

KISSIMMEE

MLS® # S5102288

3 Beds, 2 Baths, 1,216 Sf

2727 North Poinciana Boulevard 134

$270,000

KISSIMMEE

MLS® # O6193722

3 Beds, 2 Baths, 1,287 Sf

Reduced 3.6%

1911 Manatee Lane

$270,000

KISSIMMEE

MLS® # O6192463

3 Beds, 2 Baths, 1,410 Sf

2300 Butterfly Palm Way 305

$270,000

KISSIMMEE

MLS® # O6190906

3 Beds, 2 Baths, 1,402 Sf

Reduced 4.1%

606 Mayan Place

$270,000

KISSIMMEE

MLS® # S5100393

3 Beds, 2 Baths, 1,046 Sf

2706 Rio Grande Trail 2706

$270,000

KISSIMMEE

MLS® # O6168656

3 Beds, 2 Baths, 1,250 Sf

Reduced 3.6%

2733 Rivkin Drive

$270,000

KISSIMMEE

MLS® # S5094870

3 Beds, 2 Baths, 1,402 Sf

4000 San Gallo Drive 104

$269,990

KISSIMMEE

MLS® # O6191808

3 Beds, 2 Baths, 1,296 Sf

New

829 Palermo Court

$269,900

KISSIMMEE

MLS® # O6199423

3 Beds, 2 Baths, 1,272 Sf

Reduced 6.6%

1822 Manitoba Court

$269,900

KISSIMMEE

MLS® # O6197792

4 Beds, 2 Baths, 1,450 Sf

Reduced 3.6%

926 Louvre Court

$269,900

KISSIMMEE

MLS® # O6196620

3 Beds, 2 Baths, 1,248 Sf

Reduced 10%

2145 Jessa Drive

$269,900

KISSIMMEE

MLS® # S5102629

3 Beds, 2 Baths, 1,121 Sf

Reduced 7.6%

2305 Silver Palm Drive 103

$269,900

KISSIMMEE

MLS® # O6185326

3 Beds, 2 Baths, 1,268 Sf

8827 Grand Palms Circle B

$269,900

KISSIMMEE

MLS® # O6184879

3 Beds, 2 Baths, 1,222 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.