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

201 Cobalt Drive

$340,990

KISSIMMEE

MLS® # O6201150

4 Beds, 2 Baths, 1,828 Sf

547 Big Sioux Court

$340,900

KISSIMMEE

MLS® # O6173101

4 Beds, 3 Baths, 2,596 Sf

New

2339 Caravelle Circle

$340,000

KISSIMMEE

MLS® # O6204391

4 Beds, 3 Baths, 1,400 Sf

New

4501 Dakota Point Court

$340,000

KISSIMMEE

MLS® # S5104653

3 Beds, 2 Baths, 1,228 Sf

4877 Coral Castle Drive

$340,000

KISSIMMEE

MLS® # O6199732

3 Beds, 3 Baths, 1,844 Sf

2824 Oakwater Drive 2824

$340,000

KISSIMMEE

MLS® # S5101166

3 Beds, 2 Baths, 1,255 Sf

1884 Red Canyon Drive

$340,000

KISSIMMEE

MLS® # S5099881

3 Beds, 3 Baths, 1,624 Sf

3203 Oyster Lane

$340,000

KISSIMMEE

MLS® # S5098159

3 Beds, 2 Baths, 1,300 Sf

8406 Crystal Cove Loop

$340,000

KISSIMMEE

MLS® # O6147754

3 Beds, 3 Baths, 1,291 Sf

8975 Shine Drive

$340,000

KISSIMMEE

MLS® # O6136213

3 Beds, 2 Baths, 1,300 Sf

Reduced 1.4%

1005 Park Ridge Circle

$340,000

KISSIMMEE

MLS® # S5087858

3 Beds, 3 Baths, 1,291 Sf

New

609 Hudson Valley Drive

$339,999

KISSIMMEE

MLS® # S5104378

4 Beds, 2 Baths, 1,560 Sf

Reduced 1.4%

2211 San Vittorino Circle 102

$339,999

KISSIMMEE

MLS® # O6161943

4 Beds, 3 Baths, 1,470 Sf

Reduced 2.9%

197 Los Gatos Place

$339,999

KISSIMMEE

MLS® # O6149203

2 Beds, 2 Baths, 2,103 Sf

Reduced 1.4%

845 Marquis Court

$339,999

KISSIMMEE

MLS® # S5087215

4 Beds, 2 Baths, 1,620 Sf

2523 Hassonite Street

$339,900

KISSIMMEE

MLS® # O6196449

3 Beds, 3 Baths, 1,769 Sf

4732 Coral Castle Drive

$339,900

KISSIMMEE

MLS® # O6190716

3 Beds, 3 Baths, 1,762 Sf

1851 Houston Street 1851

$339,900

KISSIMMEE

MLS® # U8238721

3 Beds, 3 Baths, 1,452 Sf

4692 Ross Lanier Lane

$339,900

KISSIMMEE

MLS® # S5101981

3 Beds, 2 Baths, 1,671 Sf

Reduced 4.2%

2409 Silver Palm Drive

$339,900

KISSIMMEE

MLS® # S5099026

3 Beds, 3 Baths, 1,440 Sf

Reduced 1.4%

2305 Butterfly Palm Way 205

$339,900

KISSIMMEE

MLS® # O6126321

3 Beds, 2 Baths, 1,268 Sf

New

1001 Via Santae Lane 105

$339,000

KISSIMMEE

MLS® # S5104536

1 Beds, 1 Baths, 792 Sf

7506 Bliss Way

$339,000

KISSIMMEE

MLS® # O6201392

3 Beds, 3 Baths, 1,808 Sf

8415 Crystal Cove Loop

$339,000

KISSIMMEE

MLS® # S5104071

3 Beds, 3 Baths, 1,291 Sf

Reduced 2%

3460 Beau Road

$339,000

KISSIMMEE

MLS® # O6190276

3 Beds, 3 Baths, 2,019 Sf

3013 Bonfire Beach Drive 201

$339,000

KISSIMMEE

MLS® # S5101551

3 Beds, 2 Baths, 1,444 Sf

Reduced 0.3%

3210 Gold Lane

$339,000

KISSIMMEE

MLS® # O6179219

3 Beds, 2 Baths, 1,300 Sf

2665 Triumph Way

$338,900

KISSIMMEE

MLS® # O6200362

2 Beds, 3 Baths, 1,350 Sf

Reduced 0.4%

2924 Clarabelle Court

$338,500

KISSIMMEE

MLS® # O6176833

3 Beds, 3 Baths, 1,703 Sf

1428 Isleta Loop

$337,990

KISSIMMEE

MLS® # O6196627

3 Beds, 3 Baths, 1,673 Sf

1426 Isleta Loop

$337,990

KISSIMMEE

MLS® # O6196614

3 Beds, 3 Baths, 1,673 Sf

1424 Isleta Loop

$337,990

KISSIMMEE

MLS® # O6195347

3 Beds, 3 Baths, 1,673 Sf

1422 Isleta Loop

$337,990

KISSIMMEE

MLS® # O6195336

3 Beds, 3 Baths, 1,673 Sf

4730 Coral Castle Dr

$337,900

KISSIMMEE

MLS® # O6190698

3 Beds, 3 Baths, 1,762 Sf

2640 Roadster Lane

$337,900

KISSIMMEE

MLS® # O6189926

2 Beds, 3 Baths, 1,350 Sf

Reduced 3.7%

214 Tiffany Court

$337,000

KISSIMMEE

MLS® # O6192198

3 Beds, 2 Baths, 1,536 Sf

2176 Rio Grande Canyon Loop

$335,000

KISSIMMEE

MLS® # S5104249

4 Beds, 2 Baths, 1,731 Sf

628 Deauville Court

$335,000

KISSIMMEE

MLS® # O6197460

3 Beds, 2 Baths, 1,499 Sf

5360 Diplomat Ct 103

$335,000

KISSIMMEE

MLS® # O6196421

3 Beds, 2 Baths, 1,300 Sf

Reduced 2.9%

1639 Tench Court

$335,000

KISSIMMEE

MLS® # A4606255

4 Beds, 3 Baths, 1,714 Sf

Reduced 4.3%

826 James Drive

$335,000

KISSIMMEE

MLS® # V4935562

4 Beds, 2 Baths, 1,665 Sf

1318 Dunbarton Court

$335,000

KISSIMMEE

MLS® # O6190055

4 Beds, 2 Baths, 1,665 Sf

Reduced 1.5%

2900 Via Tuscany Way

$335,000

KISSIMMEE

MLS® # S5099858

3 Beds, 3 Baths, 1,585 Sf

Reduced 1.5%

188 East Cedarwood Circle

$335,000

KISSIMMEE

MLS® # S5100586

3 Beds, 2 Baths, 1,162 Sf

2745 Corvette Lane

$335,000

KISSIMMEE

MLS® # O6179252

2 Beds, 3 Baths, 1,290 Sf

Reduced 1.4%

1537 Colony Avenue

$335,000

KISSIMMEE

MLS® # S5099746

3 Beds, 2 Baths, 1,079 Sf

Reduced 1.5%

2371 Caravelle Circle

$335,000

KISSIMMEE

MLS® # S5098376

4 Beds, 3 Baths, 1,512 Sf

4708 Coral Castle Drive

$335,000

KISSIMMEE

MLS® # O6170861

3 Beds, 3 Baths, 1,762 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.