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 5%

2979 Red Oak Drive

$379,999

KISSIMMEE

MLS® # O6194358

3 Beds, 2 Baths, 1,220 Sf

3021 Seaview Castle Drive

$379,900

KISSIMMEE

MLS® # O6197682

3 Beds, 3 Baths, 1,540 Sf

217 North Emory Avenue

$379,900

KISSIMMEE

MLS® # O6197891

4 Beds, 2 Baths, 1,382 Sf

298 Valencia Avenue

$379,900

KISSIMMEE

MLS® # O6182149

3 Beds, 2 Baths, 1,238 Sf

3007 Bloomsbury Drive

$379,900

KISSIMMEE

MLS® # S5102265

3 Beds, 2 Baths, 1,613 Sf

Reduced 1.3%

2557 Davenport Circle

$379,900

KISSIMMEE

MLS® # O6193428

3 Beds, 2 Baths, 1,233 Sf

1117 Normandy Drive

$379,900

KISSIMMEE

MLS® # O6189690

4 Beds, 3 Baths, 2,758 Sf

Reduced 5%

1880 Ancestry

$379,900

KISSIMMEE

MLS® # O6183149

3 Beds, 2 Baths, 1,432 Sf

Reduced 2.6%

2663 Horseshoe Bay Drive

$379,900

KISSIMMEE

MLS® # S5097742

3 Beds, 2 Baths, 1,351 Sf

Reduced 2.6%

4105 Baykal Court

$379,900

KISSIMMEE

MLS® # S5096498

3 Beds, 2 Baths, 1,949 Sf

Reduced 4.8%

2923 Banana Palm Drive

$379,900

KISSIMMEE

MLS® # O6148906

4 Beds, 3 Baths, 1,902 Sf

2653 Gold Dust Circle

$379,500

KISSIMMEE

MLS® # O6195629

3 Beds, 2 Baths, 1,521 Sf

191 Owenshire Circle

$379,500

KISSIMMEE

MLS® # S5101944

3 Beds, 2 Baths, 1,560 Sf

Reduced 1.4%

4504 Bluff Oak Loop

$379,500

KISSIMMEE

MLS® # O6164934

4 Beds, 2 Baths, 1,843 Sf

Reduced 0.1%

535 Delido Way

$379,500

KISSIMMEE

MLS® # O6153058

4 Beds, 2 Baths, 2,236 Sf

Reduced 1.8%

4753 Sparkling Shell Avenue

$379,190

KISSIMMEE

MLS® # O6188310

3 Beds, 3 Baths, 1,699 Sf

New

219 Big Sioux Drive

$379,000

KISSIMMEE

MLS® # O6198314

4 Beds, 3 Baths, 2,806 Sf

Reduced 2.6%

1466 Vicks Drive

$379,000

KISSIMMEE

MLS® # W7863882

3 Beds, 2 Baths, 1,356 Sf

2495 Palm Tree Drive

$379,000

KISSIMMEE

MLS® # S5102195

4 Beds, 3 Baths, 2,272 Sf

5118 Adelaide Drive

$379,000

KISSIMMEE

MLS® # O6176370

4 Beds, 4 Baths, 1,637 Sf

Reduced 5%

519 Bromley Court

$379,000

KISSIMMEE

MLS® # A4596406

4 Beds, 5 Baths, 3,894 Sf

Reduced 2.1%

650 Mesilla Drive

$379,000

KISSIMMEE

MLS® # S5096410

4 Beds, 2 Baths, 2,088 Sf

Reduced 0.3%

N/A

$378,900

KISSIMMEE

MLS® # S5098494

4 Beds, 2 Baths, 1,828 Sf

Reduced 1.3%

58 Peterlee Court

$378,000

KISSIMMEE

MLS® # O6183068

4 Beds, 4 Baths, 2,948 Sf

New

8958 Candy Palm Road

$377,500

KISSIMMEE

MLS® # O6197853

4 Beds, 3 Baths, 1,902 Sf

Reduced 2.1%

2910 Springlake Village Boulevard

$377,000

KISSIMMEE

MLS® # S5097765

3 Beds, 2 Baths, 1,369 Sf

Reduced 0.5%

N/A

$377,000

KISSIMMEE

MLS® # O6127592

4 Beds, 2 Baths, 2,240 Sf

2026 Rankin Street

$375,990

KISSIMMEE

MLS® # O6145811

3 Beds, 3 Baths, 1,816 Sf

Reduced 2.4%

3121 Paradox Circle 207 207

$375,900

KISSIMMEE

MLS® # S5084320

2 Beds, 2 Baths, 1,186 Sf

5649 Le Marin Way

$375,845

KISSIMMEE

MLS® # O6194651

4 Beds, 2 Baths, 1,848 Sf

5654 Le Marin Way

$375,795

KISSIMMEE

MLS® # O6190881

4 Beds, 2 Baths, 1,848 Sf

New

2624 Giardino Loop

$375,000

KISSIMMEE

MLS® # O6200055

3 Beds, 3 Baths, 1,603 Sf

New

66 Orquid Court

$375,000

KISSIMMEE

MLS® # O6198394

4 Beds, 3 Baths, 1,861 Sf

Reduced 5.1%

218 Dalton Drive

$375,000

KISSIMMEE

MLS® # O6196404

4 Beds, 3 Baths, 2,792 Sf

249 Fig Court

$375,000

KISSIMMEE

MLS® # P4930045

4 Beds, 2 Baths, 1,869 Sf

3038 Eagle Crossing Drive

$375,000

KISSIMMEE

MLS® # O6194281

3 Beds, 2 Baths, 1,795 Sf

2932 Cello Lane

$375,000

KISSIMMEE

MLS® # O6194207

3 Beds, 3 Baths, 1,690 Sf

2388 Topaz Trail

$375,000

KISSIMMEE

MLS® # O6191519

3 Beds, 2 Baths, 1,684 Sf

4705 Cheyenne Point Trl Trail

$375,000

KISSIMMEE

MLS® # O6189111

3 Beds, 2 Baths, 1,302 Sf

3180 Paradox Circle 203

$375,000

KISSIMMEE

MLS® # O6187509

2 Beds, 2 Baths, 1,196 Sf

4721 Clock Tower Dr 304

$375,000

KISSIMMEE

MLS® # O6187386

2 Beds, 2 Baths, 1,126 Sf

2418 Ashecroft Drive

$375,000

KISSIMMEE

MLS® # S5099164

4 Beds, 2 Baths, 1,560 Sf

Reduced 1.3%

8968 Silver Place

$375,000

KISSIMMEE

MLS® # O6168125

3 Beds, 2 Baths, 1,300 Sf

Reduced 1.3%

1983 Cricket Cradle Drive

$375,000

KISSIMMEE

MLS® # O6167245

4 Beds, 2 Baths, 1,843 Sf

Reduced 1.3%

547 Brighton Court

$375,000

KISSIMMEE

MLS® # O6163175

4 Beds, 3 Baths, 2,691 Sf

Reduced 50.6%

8117 Surf Street

$375,000

KISSIMMEE

MLS® # O6161909

3 Beds, 2 Baths, 1,787 Sf

Reduced 3.6%

3102 Westbrook Road

$375,000

KISSIMMEE

MLS® # S5094377

4 Beds, 3 Baths, 2,393 Sf

Reduced 6.2%

3208 Oyster Lane

$375,000

KISSIMMEE

MLS® # O6114442

4 Beds, 3 Baths, 1,694 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.