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

2305 Silver Palm Drive 102

$325,000

KISSIMMEE

MLS® # S5090970

3 Beds, 2 Baths, 1,402 Sf

745 Volterra Boulevard

$324,900

KISSIMMEE

MLS® # S5103137

2 Beds, 2 Baths, 1,467 Sf

457 Spike Court

$324,000

KISSIMMEE

MLS® # S5102666

4 Beds, 2 Baths, 1,782 Sf

Reduced 0.9%

2913 Puerta Del Sol Boulevard

$324,000

KISSIMMEE

MLS® # O6142889

3 Beds, 3 Baths, 1,540 Sf

Reduced 0.5%

2762 Club Cortile Circle

$323,500

KISSIMMEE

MLS® # S5091405

4 Beds, 3 Baths, 1,880 Sf

New

2905 Edenshire Way 102

$320,000

KISSIMMEE

MLS® # T3521569

3 Beds, 2 Baths, 1,300 Sf

New

152 Gulf Dr

$320,000

KISSIMMEE

MLS® # S5103487

3 Beds, 2 Baths, 1,797 Sf

818 South Emory Avenue

$320,000

KISSIMMEE

MLS® # S5103292

3 Beds, 2 Baths, 1,095 Sf

Reduced 1.5%

8493 Crystal Cove Loop

$320,000

KISSIMMEE

MLS® # P4927848

3 Beds, 3 Baths, 1,291 Sf

Reduced 5.9%

141 Pompano Beach Drive

$320,000

KISSIMMEE

MLS® # O6190369

3 Beds, 3 Baths, 1,286 Sf

Reduced 3%

1042 Universal Rest Place

$320,000

KISSIMMEE

MLS® # S5099139

3 Beds, 2 Baths, 1,728 Sf

Reduced 5.3%

N/A

$320,000

KISSIMMEE

MLS® # O6113256

3 Beds, 3 Baths, 1,650 Sf

3137 Sun Lake Court B

$320,000

KISSIMMEE

MLS® # O6096244

3 Beds, 2 Baths, 1,650 Sf

8102 Princess Palm Lane 103

$319,990

KISSIMMEE

MLS® # O6188748

3 Beds, 2 Baths, 1,268 Sf

Reduced 1.5%

824 Ognon Court

$319,990

KISSIMMEE

MLS® # C7486515

4 Beds, 2 Baths, 1,665 Sf

281 Vestrella Drive

$319,900

KISSIMMEE

MLS® # O6195860

2 Beds, 2 Baths, 1,305 Sf

2208 San Vittorino Circle 101

$319,900

KISSIMMEE

MLS® # O6192167

4 Beds, 3 Baths, 1,470 Sf

Reduced 1.6%

411 Peppermill Circle

$319,900

KISSIMMEE

MLS® # O6179892

3 Beds, 3 Baths, 1,941 Sf

Reduced 1.5%

8550 Crystal Cove Loop

$319,900

KISSIMMEE

MLS® # S5098705

3 Beds, 3 Baths, 1,277 Sf

7631 Heritage Crossing Way 302

$319,900

KISSIMMEE

MLS® # O6174068

3 Beds, 2 Baths, 1,344 Sf

8836 Dunes Court 13-307

$319,900

KISSIMMEE

MLS® # O6169383

4 Beds, 2 Baths, 1,456 Sf

Reduced 3.6%

4005 Santa Maria Drive 103

$319,900

KISSIMMEE

MLS® # A4587322

3 Beds, 2 Baths, 1,296 Sf

New

1301 Anchor Bend Way

$319,000

KISSIMMEE

MLS® # O6199851

3 Beds, 3 Baths, 1,553 Sf

Reduced 3%

4875 Coral Castle Drive

$319,000

KISSIMMEE

MLS® # O6195314

3 Beds, 3 Baths, 1,762 Sf

Reduced 2.4%

831 Bella Viana Road

$319,000

KISSIMMEE

MLS® # S5097053

2 Beds, 2 Baths, 1,712 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 3.3%

160 Big Black Drive

$319,000

KISSIMMEE

MLS® # S5094858

4 Beds, 2 Baths, 1,793 Sf

Reduced 4.5%

609 Estrada Lane

$319,000

KISSIMMEE

MLS® # R4907096

3 Beds, 2 Baths, 1,565 Sf

511 Brighton Court

$318,990

KISSIMMEE

MLS® # S5102480

4 Beds, 2 Baths, 2,236 Sf

8943 Shine Drive

$318,900

KISSIMMEE

MLS® # S5102569

3 Beds, 2 Baths, 1,300 Sf

Reduced 2.2%

1121 Normandy Drive

$318,000

KISSIMMEE

MLS® # O6184809

3 Beds, 2 Baths, 1,738 Sf

1321 Anchor Bend Way

$317,315

KISSIMMEE

MLS® # O6186658

3 Beds, 3 Baths, 1,373 Sf

1317 Anchor Bend Way

$317,215

KISSIMMEE

MLS® # O6186726

3 Beds, 3 Baths, 1,373 Sf

Reduced 0.9%

901 Dartmouth Ct

$317,000

KISSIMMEE

MLS® # O6137010

3 Beds, 2 Baths, 1,810 Sf

3402 Fallbrook Drive

$315,900

KISSIMMEE

MLS® # S5102825

2 Beds, 2 Baths, 1,353 Sf

New

N/A

$315,000

KISSIMMEE

MLS® # O6198240

3 Beds, 2 Baths, 1,332 Sf

New

720 Del Ray Drive

$315,000

KISSIMMEE

MLS® # T3520180

3 Beds, 2 Baths, 1,414 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

4562 Yellowgold Road E 105

$315,000

KISSIMMEE

MLS® # O6191795

3 Beds, 2 Baths, 1,296 Sf

2903 Sunstone Drive

$315,000

KISSIMMEE

MLS® # O6189841

4 Beds, 3 Baths, 1,985 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

1113 Park Ridge Circle

$315,000

KISSIMMEE

MLS® # O6178070

3 Beds, 3 Baths, 1,277 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.