View 2609 MONTEGO BAY BOULEVARD Kissimmee, FL MLS# S5155301
  • Recently Listed with Virtual Tour
1 of 14
$2,600
3

Beds

2.0

Baths

1,502

Sq.Ft.

2609 MONTEGO BAY BOULEVARD

Kissimmee, FL

Courtesy of FLORIDA HOMES REALTY & MORTGAGE
View 2770 CLUB CORTILE CIRCLE A Kissimmee, FL MLS# O6432997
  • Recently Listed with Virtual Tour
1 of 11
$1,850
3

Beds

2.0

Baths

1,202

Sq.Ft.

2770 CLUB CORTILE CIRCLE A

Kissimmee, FL

Courtesy of LA ROSA REALTY CW PROPERTIES L
View 637 REGENCY WAY Kissimmee, FL MLS# O6432534
  • Recently Listed with Virtual Tour
1 of 16
$2,070
3

Beds

2.0

Baths

1,443

Sq.Ft.

637 REGENCY WAY

Kissimmee, FL

Courtesy of MAIN STREET RENEWAL LLC
The time to sell is now! THE TIME TO SELL IS NOW!
View 1594 FRANCES STREET Kissimmee, FL MLS# S5155414
  • Recently Listed with Virtual Tour
1 of 72
$2,950
4

Beds

2.0

Baths

1,536

Sq.Ft.

1594 FRANCES STREET

Kissimmee, FL

Courtesy of AGENT TRUST REALTY CORPORATION
View 2495 RAPOLLO DRIVE Kissimmee, FL MLS# O6432616
  • Recently Listed with Virtual Tour
1 of 66
$3,050
4

Beds

2.1

Baths

2,365

Sq.Ft.

2495 RAPOLLO DRIVE

Kissimmee, FL

Courtesy of NONA LEGACY POWERED BY LA ROSA
View 4748 BLUE DIAMOND STREET Kissimmee, FL MLS# O6432299
  • Recently Listed with Virtual Tour
1 of 13
$2,800
4

Beds

2.1

Baths

2,631

Sq.Ft.

4748 BLUE DIAMOND STREET

Kissimmee, FL

View 787 LUCAYA DRIVE 787 Kissimmee, FL MLS# O6432640
  • Recently Listed with Virtual Tour
1 of 19
$1,300
2

Beds

2.0

Baths

954

Sq.Ft.

787 LUCAYA DRIVE 787

Kissimmee, FL

Courtesy of CENTURY 21 CARIOTI
View 313 CAEN COURT Kissimmee, FL MLS# O6432773
  • Recently Listed with Virtual Tour
1 of 16
$1,845
3

Beds

2.0

Baths

1,396

Sq.Ft.

313 CAEN COURT

Kissimmee, FL

Courtesy of MAIN STREET RENEWAL LLC
View 3202 Cupid Place Kissimmee, FL MLS# A12069632
  • Recently Listed with Virtual Tour
1 of 33
$1,900
3

Beds

2.0

Baths

3202 Cupid Place

Kissimmee, FL

Courtesy of LOKATION
View 813 W MAGNOLIA STREET Kissimmee, FL MLS# O6430474
  • Recently Listed with Virtual Tour
1 of 30
$1,750
2

Beds

1.0

Baths

896

Sq.Ft.

813 W MAGNOLIA STREET

Kissimmee, FL

Courtesy of RE FLORIDA HOMES
View 352 COCOA COURT Kissimmee, FL MLS# S5155449
  • Recently Listed
1 of 17
$1,699
2

Beds

2.0

Baths

1,001

Sq.Ft.

352 COCOA COURT

Kissimmee, FL

View 64 CORDONA DRIVE A Kissimmee, FL MLS# S5155486
  • Recently Listed with Virtual Tour
1 of 24
$1,700
3

Beds

2.0

Baths

1,300

Sq.Ft.

64 CORDONA DRIVE A

Kissimmee, FL

View 2706 MONTICELLO WAY Kissimmee, FL MLS# S5155500
$3,300
4

Beds

2.1

Baths

2,328

Sq.Ft.

2706 MONTICELLO WAY

Kissimmee, FL

View 4759 CLOISTER STREET Kissimmee, FL MLS# O6433108
  • Recently Listed with Virtual Tour
1 of 13
$2,550
4

Beds

2.0

Baths

1,848

Sq.Ft.

4759 CLOISTER STREET

Kissimmee, FL

View 202 WATTS LANE D Kissimmee, FL MLS# S5155331
  • Recently Listed with Virtual Tour
1 of 18
$1,650
2

Beds

2.1

Baths

1,088

Sq.Ft.

202 WATTS LANE D

Kissimmee, FL

Courtesy of NONA LEGACY POWERED BY LA ROSA
View 4819 WORCHESTER DRIVE Kissimmee, FL MLS# O6432248
  • Recently Listed with Virtual Tour
1 of 27
$2,650
4

Beds

2.0

Baths

1,936

Sq.Ft.

4819 WORCHESTER DRIVE

Kissimmee, FL

Courtesy of EXP REALTY LLC
View 198 MAJORS LANE Kissimmee, FL MLS# O6432330
  • Recently Listed with Virtual Tour
1 of 18
$1,900
3

Beds

2.0

Baths

4,488

Sq.Ft.

198 MAJORS LANE

Kissimmee, FL

View 2660 SAN SIMEON WAY Kissimmee, FL MLS# TB8537602
  • Recently Listed with Virtual Tour
1 of 15
$3,055
4

Beds

2.1

Baths

2,338

Sq.Ft.

2660 SAN SIMEON WAY

Kissimmee, FL

Courtesy of DARWIN HOMES, LLC.
View 2433 BENJAMIN DRIVE Kissimmee, FL MLS# S5154812
  • Recently Listed
1 of 32
$2,300
3

Beds

2.0

Baths

1,580

Sq.Ft.

2433 BENJAMIN DRIVE

Kissimmee, FL

Courtesy of KELLER WILLIAMS LEGACY REALTY
View 5006 MANGROVE ALLEY 205 Kissimmee, FL MLS# S5155394
  • Recently Listed with Virtual Tour
1 of 10
$1,200
1

Beds

1.0

Baths

677

Sq.Ft.

5006 MANGROVE ALLEY 205

Kissimmee, FL

About Kissimmee

Newcomers who want all the world-class amenities of a major metropolitan area but the relaxed pace and feeling of small-town living will enjoy Kissimmee.  Few towns can claim the nearby attractions that residents of Kissimmee enjoy, including leisure activities, recreational facilities, shopping outlets, dinner shows, and internationally famous theme parks.  Even closer to the community are unique attractions ranging from the World of Orchids and Chinatown to the Flying Tigers Warbird Restoration Air Museum.  The Osceola Center for the Arts anchors a strong cultural community.  Outdoor enthusiasts will find riding stables, golf courses, tennis courts, water sports, and crowd-pleasing spectator sports.  The Osceola County Stadium is the spring training home of the Houston Astros baseball team, and hosts summer games for the Astros' minor league team.  Festivals and celebrations brighten every season, highlighted by one of the nation's most famous rodeos.  Residents and visitors alike enjoy strolling through the restored downtown district with its quaint shops and cafes.  A diverse selection of housing ranges from cozy bungalows in the heart of town to magnificent estates or luxurious condominiums in beautiful new developments.

Listings in Kissimmee, FL

3,556

Estimated median home price

$385,000
Kissimmee FL Homes for Sale & Properties

Weichert Realtors is one of the nation's leading providers of Kissimmee, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Kissimmee, FL.

Homes for Sale by Price in Kissimmee, FL

PriceCount
$0 - 100K117
$100K - 200K160
$200K - 300K681
$300K - 400K1,006
$400K - 500K666
$500K - 600K362
$600K - 700K207
$700K - 800K87
$800K - 900K68
$900K - 1M53
$1M - Max149

Homes for Sale by Type in Kissimmee, FL

Property TypeCount
Single Family1,992
Townhouse798
Condo472
Commercial81
Rental998
Lots and Land170
Condo/Town/CoOp0
CoOp0
Multi Family23
Mobile Home18
Farms0

(Data as of 8/12/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Data is updated as of 8/13/2026.

The data relating to real estate for sale on this web site comes in part from the BROKER RECIPROCITY Program of M.L.S. of Naples, Inc. Real estate listings held by brokerage firms other than Weichert Realtors are marked with the BROKER RECIPROCITY logo (little black house) and detailed information about them includes the name of the listing brokerage.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Any use of search facilities of data on the site other than by consumers looking to purchase real estate is prohibited.

The information displayed on this website comes in part from the Broker Reciprocity Program of Brevard County, Florida. Real estate listings held by brokerage firms other than WEICHERT in Florida are marked with the Broker Reciprocity thumbnail. Copyright 2006, the Multiple Listing Service of South Brevard County, Inc. and Space Coast Association of REALTORS®, Inc. All rights reserved.

The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

The information being provided is for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective consumers may be interested in purchasing

Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

Data is updated as of 8/13/2026.