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, $300,000 - $400,000

Reduced 4.6%

673 Basingstoke Court

$310,000

KISSIMMEE

MLS® # O6156644

4 Beds, 2 Baths, 1,640 Sf

Reduced 11.2%

8407 Blue Lagoon Drive

$310,000

KISSIMMEE

MLS® # O6106696

3 Beds, 3 Baths, 1,291 Sf

Reduced 3.9%

2717 Camaro Drive

$309,950

KISSIMMEE

MLS® # S5096799

3 Beds, 3 Baths, 1,440 Sf

New

2020 Lacie Jo Lane

$309,900

KISSIMMEE

MLS® # O6199107

3 Beds, 3 Baths, 1,807 Sf

New

621 Gila Drive

$309,900

KISSIMMEE

MLS® # O6195178

3 Beds, 2 Baths, 1,273 Sf

60 Dorset Drive

$309,900

KISSIMMEE

MLS® # O6197189

3 Beds, 2 Baths, 1,376 Sf

196 Ventana Drive

$309,900

KISSIMMEE

MLS® # S5103799

2 Beds, 2 Baths, 1,574 Sf

106 Birmingham Drive

$309,900

KISSIMMEE

MLS® # O6198236

3 Beds, 2 Baths, 1,272 Sf

519 Presido Park Pl

$309,900

KISSIMMEE

MLS® # S5103083

2 Beds, 2 Baths, 1,434 Sf

313 Erie Drive

$309,900

KISSIMMEE

MLS® # S5102717

4 Beds, 2 Baths, 1,912 Sf

761 Leopard Court

$309,900

KISSIMMEE

MLS® # S5102365

3 Beds, 2 Baths, 1,819 Sf

Reduced 3.1%

4778 Vero Beach Place

$309,900

KISSIMMEE

MLS® # O6162910

3 Beds, 3 Baths, 1,286 Sf

Reduced 1.6%

924 Derbyshire Drive

$309,900

KISSIMMEE

MLS® # S5088808

4 Beds, 2 Baths, 1,730 Sf

Reduced 1.9%

247 Citrus Drive

$309,000

KISSIMMEE

MLS® # O6193486

3 Beds, 1 Baths, 903 Sf

Reduced 1.9%

8103 Coconut Palm Way 105

$309,000

KISSIMMEE

MLS® # O6152487

3 Beds, 2 Baths, 1,402 Sf

Reduced 3.1%

236 Dalton Drive

$309,000

KISSIMMEE

MLS® # O6163541

3 Beds, 2 Baths, 1,414 Sf

2228 Virginia Drive

$308,500

KISSIMMEE

MLS® # O6176281

3 Beds, 1 Baths, 1,102 Sf

Reduced 3.1%

3127 Sun Lake Court A

$307,500

KISSIMMEE

MLS® # S5100293

3 Beds, 3 Baths, 1,650 Sf

642 Cornerstone Drive

$307,000

KISSIMMEE

MLS® # O6177271

3 Beds, 3 Baths, 1,512 Sf

Reduced 2.5%

530 Glade Court

$307,000

KISSIMMEE

MLS® # O6159973

3 Beds, 2 Baths, 1,656 Sf

Reduced 7.4%

1361 Anchor Bend Way

$305,800

KISSIMMEE

MLS® # O6186736

3 Beds, 3 Baths, 1,373 Sf

622 Parakeet Court

$305,000

KISSIMMEE

MLS® # O6200211

3 Beds, 2 Baths, 1,485 Sf

913 Gascony Court

$305,000

KISSIMMEE

MLS® # S5103830

3 Beds, 2 Baths, 1,968 Sf

8515 Crystal Cove Loop

$305,000

KISSIMMEE

MLS® # O6191287

3 Beds, 3 Baths, 1,291 Sf

611 Elbridge Drive

$305,000

KISSIMMEE

MLS® # O6197250

3 Beds, 2 Baths, 1,474 Sf

3109 Seaview

$305,000

KISSIMMEE

MLS® # S5103010

2 Beds, 3 Baths, 1,112 Sf

Reduced 16.4%

1130 Munster Court

$305,000

KISSIMMEE

MLS® # O6181858

5 Beds, 3 Baths, 2,121 Sf

Reduced 4.7%

903 Parasol Place

$305,000

KISSIMMEE

MLS® # S5099935

3 Beds, 2 Baths, 1,446 Sf

Reduced 1.6%

2302 Silver Palm Drive 203

$305,000

KISSIMMEE

MLS® # O6152505

3 Beds, 2 Baths, 1,268 Sf

Reduced 9%

1345 Anchor Bend Way

$302,000

KISSIMMEE

MLS® # O6165041

3 Beds, 3 Baths, 1,373 Sf

Reduced 9%

1341 Anchor Bend Way

$302,000

KISSIMMEE

MLS® # O6164998

3 Beds, 3 Baths, 1,373 Sf

New

303 Kingfish Circle

$300,000

KISSIMMEE

MLS® # O6203872

4 Beds, 2 Baths, 1,936 Sf

New

1421 Teal Court

$300,000

KISSIMMEE

MLS® # T3524682

3 Beds, 2 Baths, 1,317 Sf

2826 California Boulevard

$300,000

KISSIMMEE

MLS® # S5103854

3 Beds, 2 Baths, 1,484 Sf

Reduced 1.6%

3238 River Branch Circle

$300,000

KISSIMMEE

MLS® # O6197851

2 Beds, 2 Baths, 1,512 Sf

312 Dolphin Way

$300,000

KISSIMMEE

MLS® # O6194208

4 Beds, 2 Baths, 1,932 Sf

3008 Bird Of Paradise Lane

$300,000

KISSIMMEE

MLS® # O6192146

2 Beds, 3 Baths, 1,161 Sf

Reduced 3.2%

4160 Bergamont Court

$300,000

KISSIMMEE

MLS® # O6191274

3 Beds, 2 Baths, 1,314 Sf

218 Abbotsbury Drive

$300,000

KISSIMMEE

MLS® # W7862798

3 Beds, 2 Baths, 1,459 Sf

Reduced 1.6%

3001 Laurel Park Lane 107

$300,000

KISSIMMEE

MLS® # O6184404

4 Beds, 2 Baths, 1,779 Sf

Reduced 1.3%

545 Casanova Court

$300,000

KISSIMMEE

MLS® # S5100113

2 Beds, 2 Baths, 1,507 Sf

Reduced 10.4%

105 East Cypress Street

$300,000

KISSIMMEE

MLS® # O6168602

1,568 Sf

Reduced 3.2%

1118 Park Ridge Circle

$300,000

KISSIMMEE

MLS® # S5094285

3 Beds, 3 Baths, 1,291 Sf

Reduced 1.6%

616 Mayan Place

$300,000

KISSIMMEE

MLS® # C7480748

3 Beds, 2 Baths, 1,449 Sf

Reduced 3.2%

8407 Crystal Cove Cove

$300,000

KISSIMMEE

MLS® # O6111954

3 Beds, 3 Baths, 1,291 Sf

Choctaw Trail

$300,000

KISSIMMEE

MLS® # O6078904

5 Acres

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.