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

1831 Wimbledon Street

$389,900

KISSIMMEE

MLS® # O6185306

3 Beds, 2 Baths, 1,770 Sf

Reduced 1.3%

2506 Aster Cove Lane

$389,900

KISSIMMEE

MLS® # O6182135

3 Beds, 2 Baths, 1,869 Sf

Reduced 3.2%

7809 Somersworth Drive

$389,900

KISSIMMEE

MLS® # T3485468

3 Beds, 2 Baths, 1,500 Sf

5688 Le Marin Way

$389,805

KISSIMMEE

MLS® # O6190650

4 Beds, 3 Baths, 2,271 Sf

Reduced 0.1%

5108 Adelaide Drive

$389,500

KISSIMMEE

MLS® # S5088237

4 Beds, 4 Baths, 1,637 Sf

3001 Jolene Court

$389,499

KISSIMMEE

MLS® # S5102411

3 Beds, 2 Baths, 1,548 Sf

454 Janice Kay Place

$389,000

KISSIMMEE

MLS® # O6196316

4 Beds, 2 Baths, 1,960 Sf

2470 Marshfield Preserve Way

$389,000

KISSIMMEE

MLS® # O6195147

3 Beds, 2 Baths, 2,037 Sf

Reduced 2.5%

8980 Cuban Palm Road

$389,000

KISSIMMEE

MLS® # S5092680

4 Beds, 3 Baths, 1,902 Sf

Reduced 2.5%

3161 Paradox Circle 303

$389,000

KISSIMMEE

MLS® # FC298261

2 Beds, 2 Baths, 1,196 Sf

Reduced 2.7%

4577 Ficus Tree Road

$389,000

KISSIMMEE

MLS® # S5098311

4 Beds, 3 Baths, 2,847 Sf

Reduced 1%

3110 Stonington Run

$389,000

KISSIMMEE

MLS® # A4573627

4 Beds, 3 Baths, 2,749 Sf

4849 West Irlo Bronson Mem Highway

$389,000

KISSIMMEE

MLS® # O6120433

1 Beds, 1 Baths, 658 Sf

Reduced 6%

7770 Sandy Ridge Drive 108

$389,000

KISSIMMEE

MLS® # O6089663

3 Beds, 3 Baths, 1,491 Sf

Reduced 1.8%

303 Blue Lake Circle

$388,000

KISSIMMEE

MLS® # S5099921

4 Beds, 2 Baths, 2,087 Sf

New

4844 Noble Cypress Street

$387,990

KISSIMMEE

MLS® # O6199819

4 Beds, 3 Baths, 1,876 Sf

157 Palazzo Lane

$387,503

KISSIMMEE

MLS® # S5102813

2 Beds, 2 Baths, 1,703 Sf

New

3073 Bloomsbury Dr

$385,000

KISSIMMEE

MLS® # S5103819

3 Beds, 2 Baths, 1,313 Sf

3261 Tranquil Trail

$385,000

KISSIMMEE

MLS® # T3518832

3 Beds, 3 Baths, 1,361 Sf

2651 Pine Needle Trail

$385,000

KISSIMMEE

MLS® # O6192017

3 Beds, 2 Baths, 1,667 Sf

Reduced 2.5%

2532 Tanner Terrace

$385,000

KISSIMMEE

MLS® # O6191684

3 Beds, 2 Baths, 1,489 Sf

309 Oceanside Court

$385,000

KISSIMMEE

MLS® # S5102229

3 Beds, 2 Baths, 1,296 Sf

Reduced 3.7%

2901 Edenshire Way 104

$385,000

KISSIMMEE

MLS® # O6090812

4 Beds, 3 Baths, 1,694 Sf

Reduced 3.8%

3120 Paradox Circle 102

$385,000

KISSIMMEE

MLS® # S5089634

2 Beds, 2 Baths, 1,186 Sf

1121 Gardanne Court

$385,000

KISSIMMEE

MLS® # O6176908

4 Beds, 2 Baths, 1,973 Sf

2693 Kendall Avenue

$385,000

KISSIMMEE

MLS® # O6166948

3 Beds, 2 Baths, 1,702 Sf

Apache Trail

$385,000

KISSIMMEE

MLS® # O6138634

5 Acres

New

864 Ognon Court

$384,999

KISSIMMEE

MLS® # O6198056

4 Beds, 3 Baths, 2,215 Sf

Reduced 1.3%

8955 California Palm Road

$384,999

KISSIMMEE

MLS® # O6173812

4 Beds, 3 Baths, 1,902 Sf

New

2871 Orange Haven Way

$384,990

KISSIMMEE

MLS® # T3520856

4 Beds, 3 Baths, 2,178 Sf

7664 Comrow Street 201

$384,900

KISSIMMEE

MLS® # O6197010

3 Beds, 2 Baths, 1,246 Sf

Reduced 0.8%

1025 Fraser Place

$384,900

KISSIMMEE

MLS® # S5102754

4 Beds, 3 Baths, 2,110 Sf

4750 Sparkling Shell Avenue

$383,190

KISSIMMEE

MLS® # O6194591

3 Beds, 3 Baths, 1,699 Sf

Reduced 0.5%

220 Aquamarine Ln Lane

$383,000

KISSIMMEE

MLS® # O6184417

4 Beds, 2 Baths, 1,974 Sf

905 Basilica Lane

$382,990

KISSIMMEE

MLS® # O6180836

5 Beds, 3 Baths, 2,601 Sf

N/A

$381,990

KISSIMMEE

MLS® # S5102823

4 Beds, 2 Baths, 1,676 Sf

4773 Sparkling Shell Avenue

$380,990

KISSIMMEE

MLS® # O6183696

3 Beds, 3 Baths, 1,699 Sf

905 Gloucester Court

$380,000

KISSIMMEE

MLS® # S5101396

4 Beds, 3 Baths, 2,844 Sf

Enhanced

905 Lake Berkley Drive

$380,000

KISSIMMEE

MLS® # O6188537

3 Beds, 2 Baths, 1,542 Sf

N/A

$380,000

KISSIMMEE

MLS® # S5099575

4 Beds, 2 Baths, 1,578 Sf

3222 Cupid Place

$380,000

KISSIMMEE

MLS® # O6181286

4 Beds, 3 Baths, 1,694 Sf

2414 Fassona Drive

$380,000

KISSIMMEE

MLS® # O6180507

3 Beds, 3 Baths, 1,603 Sf

2449 Varenna Loop

$380,000

KISSIMMEE

MLS® # S5099998

3 Beds, 3 Baths, 1,602 Sf

4614 Tribute Trail

$380,000

KISSIMMEE

MLS® # S5098579

3 Beds, 3 Baths, 1,828 Sf

Reduced 3.8%

3337 Reedy Glen Drive

$380,000

KISSIMMEE

MLS® # O6177602

4 Beds, 2 Baths, 1,952 Sf

Reduced 6.2%

3150 Paradox Circle 306

$380,000

KISSIMMEE

MLS® # O6153131

2 Beds, 2 Baths, 1,196 Sf

Reduced 1.8%

5669 Sycamore Canyon Drive

$380,000

KISSIMMEE

MLS® # O6141132

4 Beds, 2 Baths, 2,010 Sf

Reduced 3.8%

4510 Dakota Point Court

$380,000

KISSIMMEE

MLS® # S5089983

3 Beds, 2 Baths, 1,330 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.