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 1.5%

8550 Crystal Cove Loop

$319,900

KISSIMMEE

MLS® # S5098705

3 Beds, 3 Baths, 1,277 Sf

Reduced 3.6%

4005 Santa Maria Drive 103

$319,900

KISSIMMEE

MLS® # A4587322

3 Beds, 2 Baths, 1,296 Sf

New

4512 Teoli Court

$319,000

KISSIMMEE

MLS® # S5105041

3 Beds, 3 Baths, 2,178 Sf

2019 Cypress Bay Blvd

$319,000

KISSIMMEE

MLS® # O6198203

3 Beds, 3 Baths, 1,807 Sf

Reduced 3%

4875 Coral Castle Drive

$319,000

KISSIMMEE

MLS® # O6195314

3 Beds, 3 Baths, 1,762 Sf

Reduced 0.3%

141 Pompano Beach Drive

$319,000

KISSIMMEE

MLS® # O6190369

3 Beds, 3 Baths, 1,286 Sf

Reduced 1.8%

3198 River Branch Circle

$319,000

KISSIMMEE

MLS® # S5097148

2 Beds, 2 Baths, 1,512 Sf

Reduced 0.3%

3607 Main Harbor Drive

$319,000

KISSIMMEE

MLS® # O6164991

3 Beds, 3 Baths, 1,553 Sf

Reduced 0.3%

137 Aurelia Court

$319,000

KISSIMMEE

MLS® # O6160672

4 Beds, 2 Baths, 1,744 Sf

Reduced 4.5%

609 Estrada Lane

$319,000

KISSIMMEE

MLS® # R4907096

3 Beds, 2 Baths, 1,565 Sf

Reduced 2.2%

1121 Normandy Drive

$318,000

KISSIMMEE

MLS® # O6184809

3 Beds, 2 Baths, 1,738 Sf

Reduced 5.9%

214 Tiffany Court

$317,000

KISSIMMEE

MLS® # O6192198

3 Beds, 2 Baths, 1,536 Sf

Reduced 0.9%

901 Dartmouth Ct

$317,000

KISSIMMEE

MLS® # O6137010

3 Beds, 2 Baths, 1,810 Sf

Reduced 8.6%

753 Parrot Court

$316,990

KISSIMMEE

MLS® # O6201228

3 Beds, 2 Baths, 1,498 Sf

Reduced 0.6%

225 Chadworth Drive

$315,990

KISSIMMEE

MLS® # C7485138

3 Beds, 2 Baths, 1,477 Sf

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

New

4563 Yellowgold Road E 21-106

$315,000

KISSIMMEE

MLS® # O6207029

3 Beds, 2 Baths, 1,296 Sf

N/A

$315,000

KISSIMMEE

MLS® # O6198240

3 Beds, 2 Baths, 1,332 Sf

Reduced 4.5%

511 Elbridge Place

$315,000

KISSIMMEE

MLS® # S5102943

5 Beds, 3 Baths, 2,734 Sf

Reduced 1.6%

8493 Crystal Cove Loop

$315,000

KISSIMMEE

MLS® # P4927848

3 Beds, 3 Baths, 1,291 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 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

Reduced 3.1%

745 Volterra Boulevard

$314,900

KISSIMMEE

MLS® # S5103137

2 Beds, 2 Baths, 1,467 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 0.9%

201 Anzio Drive

$312,990

KISSIMMEE

MLS® # C7482671

3 Beds, 2 Baths, 1,477 Sf

Reduced 0.7%

2725 Club Cortile Circle

$312,900

KISSIMMEE

MLS® # S5099918

3 Beds, 3 Baths, 1,670 Sf

Reduced 2%

8943 Shine Drive

$312,499

KISSIMMEE

MLS® # S5102569

3 Beds, 2 Baths, 1,300 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

3430 Palmer Drive

$312,000

KISSIMMEE

MLS® # S5097549

3 Beds, 2 Baths, 1,134 Sf

Reduced 2.5%

504 Delido Way

$311,000

KISSIMMEE

MLS® # L4940140

3 Beds, 2 Baths, 1,465 Sf

New

222 Rock Springs Drive

$310,000

KISSIMMEE

MLS® # S5105124

2 Beds, 2 Baths, 1,574 Sf

New

3351 Whitestone Circle 204

$310,000

KISSIMMEE

MLS® # O6205826

3 Beds, 2 Baths, 1,433 Sf

85 Pine Island Circle

$310,000

KISSIMMEE

MLS® # S5103757

3 Beds, 2 Baths, 1,070 Sf

Reduced 1.6%

5104 Dominica Drive

$310,000

KISSIMMEE

MLS® # O6195717

3 Beds, 3 Baths, 1,312 Sf

2200 San Zanobi Drive 108

$310,000

KISSIMMEE

MLS® # S5102991

4 Beds, 3 Baths, 1,470 Sf

Reduced 1.6%

2952 Lucayan Harbour Circle 103

$310,000

KISSIMMEE

MLS® # O6195036

3 Beds, 2 Baths, 1,300 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

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.