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

2830 Virginia Drive

$374,900

KISSIMMEE

MLS® # O6196461

4 Beds, 2 Baths, 1,637 Sf

2709 Giardino Loop

$374,900

KISSIMMEE

MLS® # S5102430

3 Beds, 3 Baths, 1,602 Sf

Reduced 1.3%

191 Owenshire Circle

$374,500

KISSIMMEE

MLS® # S5101944

3 Beds, 2 Baths, 1,560 Sf

New

1021 Wood Cove

$374,000

KISSIMMEE

MLS® # S5103865

4 Beds, 3 Baths, 1,699 Sf

Reduced 0.3%

1983 Cricket Cradle Drive

$374,000

KISSIMMEE

MLS® # O6167245

4 Beds, 2 Baths, 1,843 Sf

Reduced 0.3%

2698 Chantilly Avenue

$373,990

KISSIMMEE

MLS® # S5095923

3 Beds, 3 Baths, 1,528 Sf

5372 Diplomat Court 108

$373,900

KISSIMMEE

MLS® # S5098633

4 Beds, 3 Baths, 1,694 Sf

Reduced 0.5%

2757 Missoula Street

$373,000

KISSIMMEE

MLS® # S5092620

4 Beds, 2 Baths, 1,972 Sf

1480 Erin Breeze Lane

$372,575

KISSIMMEE

MLS® # S5103346

3 Beds, 3 Baths, 1,515 Sf

Reduced 0.7%

4724 Doyle Drive

$372,500

KISSIMMEE

MLS® # O6132957

3 Beds, 2 Baths, 1,970 Sf

Reduced 2.1%

2927 Windmill Drive

$372,000

KISSIMMEE

MLS® # S5099400

3 Beds, 3 Baths, 1,690 Sf

Reduced 2.1%

367 Florida Parkway

$372,000

KISSIMMEE

MLS® # S5097360

3 Beds, 2 Baths, 1,400 Sf

1488 Erin Breeze Lane

$370,309

KISSIMMEE

MLS® # S5103782

3 Beds, 3 Baths, 1,515 Sf

3101 Grasmere View Parkway

$370,000

KISSIMMEE

MLS® # O6196092

4 Beds, 3 Baths, 2,393 Sf

1284 South Beach Circle

$370,000

KISSIMMEE

MLS® # O6189818

4 Beds, 4 Baths, 1,642 Sf

3088 Pointe Place Avenue

$370,000

KISSIMMEE

MLS® # O6174170

4 Beds, 2 Baths, 1,698 Sf

Reduced 3.9%

2693 Kendall Avenue

$370,000

KISSIMMEE

MLS® # O6166948

3 Beds, 2 Baths, 1,702 Sf

Reduced 2.6%

366 Blue Lake Circle

$370,000

KISSIMMEE

MLS® # S5096819

3 Beds, 2 Baths, 2,133 Sf

Reduced 5.1%

3150 Paradox Circle 403

$370,000

KISSIMMEE

MLS® # S5093343

2 Beds, 2 Baths, 1,196 Sf

Reduced 4.4%

5225 Sunset Canyon Drive

$370,000

KISSIMMEE

MLS® # O6149858

3 Beds, 2 Baths, 1,795 Sf

2903 Edenshire Way 102

$370,000

KISSIMMEE

MLS® # O6112639

3 Beds, 2 Baths, 1,300 Sf

New

2069 Rio Grande Canyon Loop

$369,950

KISSIMMEE

MLS® # L4944166

5 Beds, 3 Baths, 2,806 Sf

New

264 Owenshire Circle

$369,900

KISSIMMEE

MLS® # O6199437

3 Beds, 2 Baths, 1,329 Sf

927 Cambridge Court

$369,900

KISSIMMEE

MLS® # O6191157

4 Beds, 2 Baths, 2,088 Sf

Reduced 2.6%

298 Valencia Avenue

$369,900

KISSIMMEE

MLS® # O6182149

3 Beds, 2 Baths, 1,238 Sf

Reduced 1.4%

2954 Lucayan Harbour Circle 104

$369,900

KISSIMMEE

MLS® # S5101977

4 Beds, 3 Baths, 1,694 Sf

Reduced 1.3%

4400 Creeks Run Boulevard

$369,900

KISSIMMEE

MLS® # O6188083

4 Beds, 2 Baths, 1,936 Sf

Reduced 2.7%

4002 Marina Isle Drive

$369,900

KISSIMMEE

MLS® # T3509301

3 Beds, 2 Baths, 1,895 Sf

762 Squirrel Court

$369,900

KISSIMMEE

MLS® # O6170175

4 Beds, 3 Baths, 2,093 Sf

Reduced 5.1%

215 Magical Way

$369,900

KISSIMMEE

MLS® # O6164071

3 Beds, 2 Baths, 1,664 Sf

Reduced 3.9%

5370 Diplomat Court 104

$369,900

KISSIMMEE

MLS® # O6164474

4 Beds, 3 Baths, 1,694 Sf

Reduced 7.5%

4741 Clock Tower Drive 103

$369,900

KISSIMMEE

MLS® # O6132095

2 Beds, 2 Baths, 1,196 Sf

1030 Las Fuentes Drive

$369,500

KISSIMMEE

MLS® # S5094291

3 Beds, 3 Baths, 1,295 Sf

New

2722 Summer Retreat Lane

$369,000

KISSIMMEE

MLS® # O6201394

2 Beds, 2 Baths, 1,559 Sf

3575 Pineridge Circle

$369,000

KISSIMMEE

MLS® # O6193840

4 Beds, 3 Baths, 1,827 Sf

3141 Paradox Circle 103 103

$369,000

KISSIMMEE

MLS® # S5094108

2 Beds, 2 Baths, 1,196 Sf

Reduced 1.3%

3240 Cupid Place

$369,000

KISSIMMEE

MLS® # O6178740

4 Beds, 3 Baths, 1,694 Sf

Reduced 6.6%

2720 Pineridge Circle

$369,000

KISSIMMEE

MLS® # S5097756

4 Beds, 2 Baths, 1,749 Sf

Reduced 1.6%

1031 Vaquero Lane

$369,000

KISSIMMEE

MLS® # O6173489

3 Beds, 2 Baths, 1,822 Sf

3180 Paradox Circle 406

$369,000

KISSIMMEE

MLS® # O6164176

2 Beds, 2 Baths, 1,186 Sf

Reduced 99%

5364 Diplomat Court 106

$369,000

KISSIMMEE

MLS® # S5091028

3 Beds, 2 Baths, 1,300 Sf

New

1646 Bull Hill Road

$368,990

KISSIMMEE

MLS® # O6201998

3 Beds, 3 Baths, 1,816 Sf

1448 Erin Breeze Lane

$368,982

KISSIMMEE

MLS® # S5103347

3 Beds, 3 Baths, 1,515 Sf

1472 Erin Breeze Lane

$368,614

KISSIMMEE

MLS® # S5103342

3 Beds, 3 Baths, 1,515 Sf

3150 Paradox Circle 307

$367,900

KISSIMMEE

MLS® # O6195575

2 Beds, 2 Baths, 1,186 Sf

Reduced 0.5%

5368 Diplomat Court 105

$367,900

KISSIMMEE

MLS® # S5094301

4 Beds, 3 Baths, 1,694 Sf

2750 Summer Retreat Lane

$366,390

KISSIMMEE

MLS® # O6198528

2 Beds, 2 Baths, 1,579 Sf

New

2701 Impala Lane

$365,000

KISSIMMEE

MLS® # O6200878

4 Beds, 4 Baths, 1,852 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.