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

225 Chadworth Drive

$317,990

KISSIMMEE

MLS® # C7485138

3 Beds, 2 Baths, 1,477 Sf

Reduced 0.9%

901 Dartmouth Ct

$317,000

KISSIMMEE

MLS® # O6137010

3 Beds, 2 Baths, 1,810 Sf

201 Anzio Drive

$315,990

KISSIMMEE

MLS® # C7482671

3 Beds, 2 Baths, 1,477 Sf

New

33 Willow Lane

$315,900

KISSIMMEE

MLS® # O6202470

4 Beds, 2 Baths, 1,669 Sf

3402 Fallbrook Drive

$315,900

KISSIMMEE

MLS® # S5102825

2 Beds, 2 Baths, 1,353 Sf

N/A

$315,000

KISSIMMEE

MLS® # O6198240

3 Beds, 2 Baths, 1,332 Sf

5104 Dominica Drive

$315,000

KISSIMMEE

MLS® # O6195717

3 Beds, 3 Baths, 1,312 Sf

2952 Lucayan Harbour Circle 103

$315,000

KISSIMMEE

MLS® # O6195036

3 Beds, 2 Baths, 1,300 Sf

8 Amalfi Way

$315,000

KISSIMMEE

MLS® # S5102573

3 Beds, 2 Baths, 1,232 Sf

Reduced 7.1%

345 Marquee Drive

$315,000

KISSIMMEE

MLS® # O6189819

3 Beds, 2 Baths, 1,650 Sf

1328 Burnley Court

$315,000

KISSIMMEE

MLS® # O6188143

4 Beds, 2 Baths, 1,820 Sf

Reduced 3.1%

2028 Cypress Bay Boulevard

$315,000

KISSIMMEE

MLS® # S5100096

3 Beds, 3 Baths, 1,824 Sf

Reduced 1.6%

4704 Flagler Beach Way

$315,000

KISSIMMEE

MLS® # O6174173

3 Beds, 3 Baths, 1,286 Sf

1204 South Beach Circle

$315,000

KISSIMMEE

MLS® # O6158432

3 Beds, 3 Baths, 1,468 Sf

Reduced 2.5%

4703 Ormond Beach Way

$315,000

KISSIMMEE

MLS® # S5085396

3 Beds, 3 Baths, 1,286 Sf

Reduced 3.1%

2136 Hibiscus Place

$314,990

KISSIMMEE

MLS® # S5102530

3 Beds, 2 Baths, 1,445 Sf

Reduced 1.6%

609 Regency Way

$314,900

KISSIMMEE

MLS® # O6145067

3 Beds, 2 Baths, 1,607 Sf

7526 Bliss Way 7526

$314,900

KISSIMMEE

MLS® # O6194775

3 Beds, 2 Baths, 1,427 Sf

5469 Paradise Cay Circle

$314,900

KISSIMMEE

MLS® # O6190774

3 Beds, 3 Baths, 1,187 Sf

Reduced 0.3%

2903 Sunstone Drive

$314,000

KISSIMMEE

MLS® # O6189841

4 Beds, 3 Baths, 1,985 Sf

Reduced 0.7%

2725 Club Cortile Circle

$312,900

KISSIMMEE

MLS® # S5099918

3 Beds, 3 Baths, 1,670 Sf

409 Spice Court

$312,498

KISSIMMEE

MLS® # S5102736

3 Beds, 2 Baths, 1,500 Sf

959 Derbyshire Drive

$312,000

KISSIMMEE

MLS® # S5100460

3 Beds, 2 Baths, 1,614 Sf

504 Delido Way

$311,000

KISSIMMEE

MLS® # L4940140

3 Beds, 2 Baths, 1,465 Sf

1363 Pacific Road

$310,000

KISSIMMEE

MLS® # O6200296

4 Beds, 4 Baths, 1,901 Sf

85 Pine Island Circle

$310,000

KISSIMMEE

MLS® # S5103757

3 Beds, 2 Baths, 1,070 Sf

2200 San Zanobi Drive 108

$310,000

KISSIMMEE

MLS® # S5102991

4 Beds, 3 Baths, 1,470 Sf

Reduced 1.6%

4562 Yellowgold Road E 105

$310,000

KISSIMMEE

MLS® # O6191795

3 Beds, 2 Baths, 1,296 Sf

7502 Bliss Way 7502

$310,000

KISSIMMEE

MLS® # O6191977

3 Beds, 2 Baths, 1,255 Sf

Reduced 1.6%

303 Kingfish Drive

$310,000

KISSIMMEE

MLS® # S5090054

4 Beds, 2 Baths, 1,788 Sf

8403 Blue Lagoon Drive

$310,000

KISSIMMEE

MLS® # S5100624

3 Beds, 3 Baths, 1,291 Sf

Reduced 8.1%

2700 Merrieweather Lane

$310,000

KISSIMMEE

MLS® # L4942462

3 Beds, 3 Baths, 1,703 Sf

Reduced 3.1%

2525 North Beaumont Avenue

$310,000

KISSIMMEE

MLS® # S5095656

3 Beds, 2 Baths, 1,304 Sf

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

2020 Lacie Jo Lane

$309,900

KISSIMMEE

MLS® # O6199107

3 Beds, 3 Baths, 1,807 Sf

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

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.