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

1020 Las Fuentes Drive

$364,000

KISSIMMEE

MLS® # O6197598

3 Beds, 3 Baths, 1,295 Sf

New

4015 Ambrose Avenue

$363,005

KISSIMMEE

MLS® # T3524507

3 Beds, 2 Baths, 1,555 Sf

Reduced 0.3%

2964 Lucayan Harbor Court 101

$362,900

KISSIMMEE

MLS® # O6154105

4 Beds, 3 Baths, 1,694 Sf

Reduced 2.7%

812 Del Prado Drive

$360,900

KISSIMMEE

MLS® # R4907686

3 Beds, 2 Baths, 1,571 Sf

1313 Portage Street

$360,000

KISSIMMEE

MLS® # S5103889

3 Beds, 2 Baths, 1,404 Sf

4917 Rockvale Drive

$360,000

KISSIMMEE

MLS® # O6198024

4 Beds, 2 Baths, 1,820 Sf

2964 Lucayan Harbour Circle 108

$360,000

KISSIMMEE

MLS® # S5103475

4 Beds, 3 Baths, 1,694 Sf

4956 Thames Street E

$360,000

KISSIMMEE

MLS® # O6195614

4 Beds, 3 Baths, 1,744 Sf

1149 Cambourne Drive

$360,000

KISSIMMEE

MLS® # O6196519

4 Beds, 3 Baths, 2,166 Sf

4557 Corsa Lane

$360,000

KISSIMMEE

MLS® # O6190088

3 Beds, 3 Baths, 1,295 Sf

4751 Clock Tower Drive 304

$360,000

KISSIMMEE

MLS® # O6189985

2 Beds, 2 Baths, 1,126 Sf

Reduced 4%

4705 Cheyenne Point Trl Trail

$360,000

KISSIMMEE

MLS® # O6189111

3 Beds, 2 Baths, 1,302 Sf

4680 Marcos Circle

$360,000

KISSIMMEE

MLS® # S5101344

3 Beds, 2 Baths, 1,525 Sf

7664 Comrow Street 102

$360,000

KISSIMMEE

MLS® # O6185270

2 Beds, 2 Baths, 1,081 Sf

Reduced 1.4%

2584 Amati Drive

$360,000

KISSIMMEE

MLS® # O6182112

3 Beds, 3 Baths, 1,528 Sf

Reduced 5.3%

4721 Clock Tower Drive 302

$360,000

KISSIMMEE

MLS® # O6179617

2 Beds, 2 Baths, 1,186 Sf

Reduced 3.7%

331 Medina Court

$360,000

KISSIMMEE

MLS® # O6165552

4 Beds, 2 Baths, 1,704 Sf

Reduced 1.4%

152 Aurora Lane

$360,000

KISSIMMEE

MLS® # O6158837

4 Beds, 3 Baths, 2,818 Sf

908 Gloucester Court

$359,990

KISSIMMEE

MLS® # C7492081

4 Beds, 3 Baths, 1,941 Sf

222 Anastasia Drive

$359,900

KISSIMMEE

MLS® # S5103545

2 Beds, 2 Baths, 2,057 Sf

Reduced 5.3%

217 North Emory Avenue

$359,900

KISSIMMEE

MLS® # O6197891

4 Beds, 2 Baths, 1,382 Sf

Reduced 1.4%

2784 Almaton Loop 405

$359,900

KISSIMMEE

MLS® # O6149052

3 Beds, 2 Baths, 1,410 Sf

2522 Bowmer Drive

$359,900

KISSIMMEE

MLS® # S5101514

3 Beds, 2 Baths, 1,140 Sf

938 Park Terrace Circle

$359,500

KISSIMMEE

MLS® # P4930291

4 Beds, 4 Baths, 1,645 Sf

New

1299 Axel Graeson Avenue

$359,255

KISSIMMEE

MLS® # O6204119

3 Beds, 3 Baths, 1,551 Sf

New

1307 Axel Graeson Avenue

$359,255

KISSIMMEE

MLS® # O6203153

3 Beds, 3 Baths, 1,551 Sf

1303 Axel Graeson Avenue

$359,155

KISSIMMEE

MLS® # O6200783

3 Beds, 3 Baths, 1,551 Sf

New

1301 Axel Graeson Avenue

$359,055

KISSIMMEE

MLS® # O6203137

3 Beds, 3 Baths, 1,551 Sf

3445 Hawkin Dr

$359,000

KISSIMMEE

MLS® # S5104247

3 Beds, 2 Baths, 1,524 Sf

New

1419 Orchid Lane

$359,000

KISSIMMEE

MLS® # O6200733

3 Beds, 2 Baths, 1,120 Sf

Reduced 0.8%

7628 Sand Pierre Court

$359,000

KISSIMMEE

MLS® # O6147212

2 Beds, 2 Baths, 1,435 Sf

4731 Clock Tower Drive 203

$359,000

KISSIMMEE

MLS® # O6190317

2 Beds, 2 Baths, 1,196 Sf

Reduced 1.6%

3265 Tomahawk Drive

$359,000

KISSIMMEE

MLS® # S5085049

3 Beds, 2 Baths, 1,328 Sf

Reduced 2.7%

3151 Paradox Circle 304 304

$358,990

KISSIMMEE

MLS® # O6129545

2 Beds, 2 Baths, 1,126 Sf

Reduced 4.3%

5364 Diplomat Court 108

$358,900

KISSIMMEE

MLS® # O6133175

4 Beds, 3 Baths, 1,694 Sf

2738 Summer Retreat Lane

$358,240

KISSIMMEE

MLS® # O6198536

2 Beds, 2 Baths, 1,579 Sf

2762 Summer Retreat Lane

$358,120

KISSIMMEE

MLS® # O6198393

2 Beds, 2 Baths, 1,579 Sf

Reduced 1.2%

1965 Traverse Way

$358,000

KISSIMMEE

MLS® # S5100153

3 Beds, 2 Baths, 1,448 Sf

1430 Isleta Loop

$357,990

KISSIMMEE

MLS® # O6197846

3 Beds, 3 Baths, 1,758 Sf

Reduced 0.7%

640 Baldwin Drive

$357,500

KISSIMMEE

MLS® # O6176459

3 Beds, 2 Baths, 1,422 Sf

3444 Tranquil Trail

$356,700

KISSIMMEE

MLS® # O6197583

3 Beds, 3 Baths, 1,365 Sf

Reduced 2.5%

3151 Rocky River Road

$356,000

KISSIMMEE

MLS® # O6149616

3 Beds, 2 Baths, 1,542 Sf

New

1781 Mccoy Lane

$355,990

KISSIMMEE

MLS® # O6204168

3 Beds, 3 Baths, 1,640 Sf

New

1427 Isleta Loop

$355,990

KISSIMMEE

MLS® # O6202533

3 Beds, 3 Baths, 1,758 Sf

1779 Mccoy Lane

$355,990

KISSIMMEE

MLS® # O6199108

3 Beds, 3 Baths, 1,640 Sf

1771 Mccoy Lane

$355,990

KISSIMMEE

MLS® # O6197787

3 Beds, 3 Baths, 1,640 Sf

1769 Mccoy Lane

$355,990

KISSIMMEE

MLS® # O6196570

3 Beds, 3 Baths, 1,640 Sf

9067 Beach Tea Way

$355,990

KISSIMMEE

MLS® # O6177035

3 Beds, 3 Baths, 1,473 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.