3,348 total properties
Listings provided on behalf of Weichert Realtors - Hallmark Properties
View 236 BAY HEAD DRIVE Kissimmee, FL MLS# S5152644
  • Recently Listed with Virtual Tour
1 of 12
$289,000
2

Beds

2.0

Baths

1,108

Sq.Ft.

236 BAY HEAD DRIVE

Kissimmee, FL

View 375 TRAILER LANE Kissimmee, FL MLS# S5152657
  • Recently Listed with Virtual Tour
1 of 8
$135,000
1

Beds

1.0

Baths

625

Sq.Ft.

375 TRAILER LANE

Kissimmee, FL

Courtesy of THE ARROW REALTY TEAM LLC
View 1944 THE OAKS BOULEVARD Kissimmee, FL MLS# S5152726
  • Recently Listed with Virtual Tour
1 of 27
$439,900
4

Beds

2.0

Baths

2,288

Sq.Ft.

1944 THE OAKS BOULEVARD

Kissimmee, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 3161 WINDING TRAIL Kissimmee, FL MLS# S5152605
  • Recently Listed
1 of 31
$310,000
3

Beds

2.0

Baths

1,556

Sq.Ft.

3161 WINDING TRAIL

Kissimmee, FL

View 404 QUARRY ROCK CIRCLE Kissimmee, FL MLS# S5152730
  • Recently Listed
1 of 31
OPEN HOUSE: Saturday 7/4 12:00 PM - 2:00 PM
$445,000
6

Beds

5.0

Baths

3,024

Sq.Ft.

404 QUARRY ROCK CIRCLE

Kissimmee, FL

Courtesy of KELLER WILLIAMS REALTY AT THE LAKES
View 4453 LE REVE COURT Kissimmee, FL MLS# TB8523540
  • Recently Listed
1 of 10
$390,000
4

Beds

3.1

Baths

1,752

Sq.Ft.

4453 LE REVE COURT

Kissimmee, FL

Courtesy of INVESTCOR REALTY LLC
View 2590 BORINQUEN DRIVE Kissimmee, FL MLS# O6422091
  • Recently Listed
1 of 43
$560,000
3

Beds

2.0

Baths

2,118

Sq.Ft.

2590 BORINQUEN DRIVE

Kissimmee, FL

View 2160 PRESTON LANE Kissimmee, FL MLS# O6420516
  • Recently Listed with Virtual Tour
1 of 31
$360,000
4

Beds

2.0

Baths

1,677

Sq.Ft.

2160 PRESTON LANE

Kissimmee, FL

View 625 S DELMONTE COURT Kissimmee, FL MLS# S5152409
  • Recently Listed with Virtual Tour
1 of 19
$239,600
3

Beds

2.0

Baths

1,341

Sq.Ft.

625 S DELMONTE COURT

Kissimmee, FL

View 907 HENDON PLACE Kissimmee, FL MLS# O6420435
  • Recently Listed with Virtual Tour
1 of 36
$265,000
3

Beds

2.0

Baths

1,382

Sq.Ft.

907 HENDON PLACE

Kissimmee, FL

Courtesy of KELLER WILLIAMS CLASSIC
View 2321 WATER VIEW LOOP Kissimmee, FL MLS# O6420540
  • Recently Listed with Virtual Tour
1 of 23
$269,000
3

Beds

2.1

Baths

1,460

Sq.Ft.

2321 WATER VIEW LOOP

Kissimmee, FL

View 308 CLERMONT DRIVE Kissimmee, FL MLS# O6420545
  • Recently Listed with Virtual Tour
1 of 41
$291,500
3

Beds

2.0

Baths

1,887

Sq.Ft.

308 CLERMONT DRIVE

Kissimmee, FL

View 2581 SAGE DRIVE Kissimmee, FL MLS# O6420913
  • Recently Listed
1 of 30
$297,500
3

Beds

2.0

Baths

1,434

Sq.Ft.

2581 SAGE DRIVE

Kissimmee, FL

View 452 SOUTHFIELD STREET Kissimmee, FL MLS# S5152724
  • Recently Listed with Virtual Tour
1 of 31
$679,000
6

Beds

6.1

Baths

3,317

Sq.Ft.

452 SOUTHFIELD STREET

Kissimmee, FL

View 2851 JASPER RUN Kissimmee, FL MLS# TB8523929
  • Recently Listed
1 of 40
$499,999
5

Beds

5.1

Baths

3,156

Sq.Ft.

2851 JASPER RUN

Kissimmee, FL

View 8844 GRAND PALMS CIRCLE A Kissimmee, FL MLS# O6420581
$214,900
3

Beds

2.0

Baths

1,245

Sq.Ft.

8844 GRAND PALMS CIRCLE A

Kissimmee, FL

View 62 BOLTON COURT Kissimmee, FL MLS# O6408570
  • Recently Listed
1 of 23
$309,000
4

Beds

2.0

Baths

1,874

Sq.Ft.

62 BOLTON COURT

Kissimmee, FL

View 704 PASTEUR LANE Kissimmee, FL MLS# O6418295
  • Recently Listed
1 of 26
$309,000
4

Beds

2.0

Baths

1,874

Sq.Ft.

704 PASTEUR LANE

Kissimmee, FL

View 1259 WISPY CYPRESS DRIVE Kissimmee, FL MLS# O6419499
  • Recently Listed with Virtual Tour
1 of 77
$339,900
4

Beds

2.1

Baths

1,876

Sq.Ft.

1259 WISPY CYPRESS DRIVE

Kissimmee, FL

View 1661 LOXELY TRAIL Kissimmee, FL MLS# O6420236
  • New Construction with Virtual Tour
1 of 19
$357,990
3

Beds

2.0

Baths

1,555

Sq.Ft.

1661 LOXELY TRAIL

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

3,668

Estimated median home price

$389,995
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 - 100K116
$100K - 200K174
$200K - 300K677
$300K - 400K1,031
$400K - 500K682
$500K - 600K387
$600K - 700K226
$700K - 800K97
$800K - 900K71
$900K - 1M59
$1M - Max148

Homes for Sale by Type in Kissimmee, FL

Property TypeCount
Single Family2,046
Townhouse821
Condo499
Commercial82
Rental999
Lots and Land175
Condo/Town/CoOp0
CoOp0
Multi Family22
Mobile Home20
Farms0

(Data as of 7/4/2026)

Information deemed reliable but not guaranteed.

The data relating to real estate for sale on this web site comes in part from the IDX Program of the Tallahassee Multiple Listing Service. Detailed information regarding Real estate listings held by brokerage firms 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.

Copyright 2026 Northeast Florida Multiple Listing Service, 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 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.

Data is updated as of 7/4/2026.

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 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 7/4/2026.

The data relating to real estate for sale/lease on this web site come in part from the New Smyrna Beach Board of REALTORS® Multiple Listing Service (MLS) in which this real estate firm (Broker) participates. The properties displayed may not be all of the properties in the MLS's database, or all of the properties listed with the Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with the MLS IDX logo. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein or for their use or interpretation by the user. Federal law prohibits discrimination on the basis of race, color, sex, religion, handicap, familial status or national origin in the sale, rental or financing of housing.

This data updated periodically, at an interval not to exceed 7 days.

IDX information 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.

Some properties which appear for sale on this website may subsequently have sold and may no longer be available.

© Copyright 2026 New Smyrna Beach Board of REALTORS, Inc. All rights Reserved.

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 7/4/2026.