REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
REAL ESTATE
For agentsBuySellInternationalCryptoJournal
ENES
ENES
For agentsBuySellInternationalCryptoJournal414.712.6275
HOMES FOR SALE · KISSIMMEE

Homes for sale in KissimmeeKissimmee homes for sale, with a plan built around you.

Where a short-term rental and a family home can both make sense. Highway 192 runs the rental communities near the parks, and downtown holds the older lakefront blocks. I live and work this market, so I know which streets hold value.

2,964 homes

FloridaWisconsin
Pedro Rivera
Pedro RiveraAs seen on · Media coverage
TMJ4Telemundo WisconsinCBS 58 Wisconsin
Nathalie Montmellisa hayesCaptivated Real EstateAshly SantiagoKiara Rivera Morla
5.0· 74 GOOGLE REVIEWS
976+ FAMILIES GUIDED · FL & WI
2964 ACTIVE LISTINGSLICENSED FL & WIHABLAMOS ESPAÑOL
LATEST IN KISSIMMEELIVE FROM THE MLS
393 SOUTHFIELD Street, Kissimmee, FL 34747For sale$649,0006 BEDS · 7.5 BATHS · 3,317 SQFT393 SOUTHFIELD Street, Kissimmee, FL 34747762 TOULON Drive, Kissimmee, FL 34759For sale$295,0004701 RUBY RED LANE, Kissimmee, FL 34746For sale$500,000
393 SOUTHFIELD Street, Kissimmee, FL 34747
393 SOUTHFIELD Street, Kissimmee, FL 34747 2
393 SOUTHFIELD Street, Kissimmee, FL 34747 3
For sale · 119 DAYS
$649,000$196/sqft

393 SOUTHFIELD Street

Kissimmee, FL

6 beds7.5 baths3,317 sqft

Courtesy of KRESSLER REAL ESTATE

762 TOULON Drive, Kissimmee, FL 34759
762 TOULON Drive, Kissimmee, FL 34759 2
762 TOULON Drive, Kissimmee, FL 34759 3
4701 RUBY RED LANE, Kissimmee, FL 34746
4701 RUBY RED LANE, Kissimmee, FL 34746 2
4701 RUBY RED LANE, Kissimmee, FL 34746 3
832 DRIVING RANGE Court, Kissimmee, FL 34747
832 DRIVING RANGE Court, Kissimmee, FL 34747 2
832 DRIVING RANGE Court, Kissimmee, FL 34747 3
For sale · 1 DAY
$418,000
3132 RIVER BRANCH Circle, Kissimmee, FL 34741
3132 RIVER BRANCH Circle, Kissimmee, FL 34741 2
3132 RIVER BRANCH Circle, Kissimmee, FL 34741 3
For sale
$325,000$215/sqft

3132 RIVER BRANCH Circle

530 ACADEMY Drive #201, Kissimmee, FL 34744
530 ACADEMY Drive #201, Kissimmee, FL 34744 2
530 ACADEMY Drive #201, Kissimmee, FL 34744 3
For rent
$1,595

530 ACADEMY Drive #201

Kissimmee, FL

1 bed
525 CARLSBAD Drive, Kissimmee, FL 34758
525 CARLSBAD Drive, Kissimmee, FL 34758 2
525 CARLSBAD Drive, Kissimmee, FL 34758 3
For sale · 75 DAYS
4712 HEMINGWAY HOUSE Street, Kissimmee, FL 34746
4712 HEMINGWAY HOUSE Street, Kissimmee, FL 34746 2
4712 HEMINGWAY HOUSE Street, Kissimmee, FL 34746 3
2530 MANESHAW Lane, Kissimmee, FL 34747
2530 MANESHAW Lane, Kissimmee, FL 34747 2
2530 MANESHAW Lane, Kissimmee, FL 34747 3
1127 GARDANNE Court, Kissimmee, FL 34759
1127 GARDANNE Court, Kissimmee, FL 34759 2
1127 GARDANNE Court, Kissimmee, FL 34759 3
For sale · 40 DAYS
$264,900
502 GREENBRIER Avenue, Kissimmee, FL 34747
502 GREENBRIER Avenue, Kissimmee, FL 34747 2
502 GREENBRIER Avenue, Kissimmee, FL 34747 3
501 SUMNER Street, Kissimmee, FL 34741
501 SUMNER Street, Kissimmee, FL 34741 2
501 SUMNER Street, Kissimmee, FL 34741 3
4381 CREEKSIDE Boulevard, Kissimmee, FL 34746
4381 CREEKSIDE Boulevard, Kissimmee, FL 34746 2
4381 CREEKSIDE Boulevard, Kissimmee, FL 34746 3
2590 BORINQUEN Drive, Kissimmee, FL 34744
2590 BORINQUEN Drive, Kissimmee, FL 34744 2
2590 BORINQUEN Drive, Kissimmee, FL 34744 3
1229 BERMUDA LAKES Lane #206, Kissimmee, FL 34741
1229 BERMUDA LAKES Lane #206, Kissimmee, FL 34741 2
1229 BERMUDA LAKES Lane #206, Kissimmee, FL 34741 3
1944 THE OAKS Boulevard, Kissimmee, FL 34746
1944 THE OAKS Boulevard, Kissimmee, FL 34746 2
1944 THE OAKS Boulevard, Kissimmee, FL 34746 3
625 DELMONTE Court, Kissimmee, FL 34758
625 DELMONTE Court, Kissimmee, FL 34758 2
625 DELMONTE Court, Kissimmee, FL 34758 3
For sale · 1 DAY
106 & 108 SAIL Place, Kissimmee, FL 34759
106 & 108 SAIL Place, Kissimmee, FL 34759 2
106 & 108 SAIL Place, Kissimmee, FL 34759 3
For sale · 23 DAYS
$105,000

106 & 108 SAIL Place

Kissimmee, FL

Courtesy of REALTY EXCHANGE, LLC

1259 WISPY CYPRESS Drive, Kissimmee, FL 34746
1259 WISPY CYPRESS Drive, Kissimmee, FL 34746 2
1259 WISPY CYPRESS Drive, Kissimmee, FL 34746 3
8866 GENEVE Court, Kissimmee, FL 34747
8866 GENEVE Court, Kissimmee, FL 34747 2
8866 GENEVE Court, Kissimmee, FL 34747 3
2690 LAKE Road, Kissimmee, FL 34744
2690 LAKE Road, Kissimmee, FL 34744 2
2690 LAKE Road, Kissimmee, FL 34744 3
0 SHARPEY Road, Kissimmee, FL 34744
0 SHARPEY Road, Kissimmee, FL 34744 2
0 SHARPEY Road, Kissimmee, FL 34744 3
8838 GENEVE Court, Kissimmee, FL 34747
8838 GENEVE Court, Kissimmee, FL 34747 2
8838 GENEVE Court, Kissimmee, FL 34747 3
For sale · 12 DAYS
2930 WHITE CEDAR Circle, Kissimmee, FL 34741
2930 WHITE CEDAR Circle, Kissimmee, FL 34741 2
2930 WHITE CEDAR Circle, Kissimmee, FL 34741 3
See 2,964 homes
← PreviousPage 69 of 124Next →

Living in Kissimmee

Where a short-term rental and a family home can both make sense. Highway 192 runs the rental communities near the parks, and downtown holds the older lakefront blocks. I live and work this market, so I know which streets hold value.

Nathalie Montmellisa hayesCaptivated Real EstateAshly SantiagoKiara Rivera Morla
5.0· 74 GOOGLE REVIEWS
976+ FAMILIES GUIDED · FL & WI
LICENSED FL & WIHABLAMOS ESPAÑOL
Sunrise over Kissimmee's lakefront park on Lake Tohopekaliga
The Kissimmee (Tohopekaliga) Lighthouse on the lakefront
A historic brick retail building on Broadway Avenue in downtown Kissimmee
PHOTOS: Chad Sparkes from Kissimmee,Florida, United States (CC BY 2.0) · Freeholdman12 (CC BY 4.0) · Pokemonprime (CC BY 4.0)

Kissimmee right now

AS OF NOV 7 · LIVE FROM THE MLS
ABOUT KISSIMMEE

Gateway city, working market.

Kissimmee sits on the south side of Orlando, wrapped around the theme-park corridor and stretched along US-192. New builds, resale subdivisions, and short-term rental zones all live here, and each one runs on its own rules.

Es un mercado activo, todos los días. I read the zoning, the HOA, and the short-term rental maps with you before you fall for a floor plan. First-time buyer, vacation home, or rental investor: same broker, same process, in English or Spanish.

QUESTIONS I GET ABOUT KISSIMMEE

Straight answers, no queue.

The count on this page is live from the MLS and changes through the day, so the number above the grid is the current one. To narrow it, filter by price and bedrooms, or call or text me at 414.712.6275 and tell me what you need in Kissimmee. I will send you a shorter, better list than any filter produces.

Yes. I am a bilingual real estate broker licensed in Florida, and I handle the entire Kissimmee transaction in Spanish if you prefer, from the first showing through inspection and closing. The same live search runs in Spanish at pedrobandorivera.com/es/buy/kissimmee, with the same listings.

A gateway city with a working market: new construction west along 192, resale neighborhoods around the lakefront and downtown, and short-term rental zones near the parks, each with its own rules and HOA.

Call or text 414.712.6275, or send the address through pedrobandorivera.com/contact. I answer my own messages the same day and schedule showings myself, so there is no lead form queue and no handoff. I work Kissimmee directly as a licensed broker, in English or Spanish.

KEEP LOOKING NEARBY

Central Florida, city by city.

KissimmeeSt. CloudCelebrationLake Nona
NEIGHBORHOOD GUIDES ON RETHOUGHT-REALESTATE.COM
Kissimmee guide→Celebration→Four Corners→Davenport→
BEFORE IT HITS THE FEED · KISSIMMEE

Don't see it yet? Tell me what you want in Kissimmee.

I hear about homes before they reach the feed, from agents I close with every month. Send me your budget and must-haves and I will go find it, in English or Spanish.

OR CALL OR TEXT414.712.6275
REAL ESTATE
CALL OR TEXT · HABLAMOS ESPAÑOL
414.712.6275
Pedro J Rivera, Broker & Founder
reThought Real Estate · Kissimmee, FL & Milwaukee, WI
Email
BUY
Orlando homesKissimmee homesMilwaukee homesBuying process
SELL
My home's valueListing processSeller's guide
AREAS
OrlandoKissimmeeSt. CloudMilwaukeeWauwatosaAll areas →
MORE
For agentsInternational projectsCryptoCalculatorsJournalWho is Pedro?
© 2026 PEDRO J RIVERA · BROKER, reTHOUGHT REAL ESTATE · LIC FL & WI
LIC FL & WIPRIVACYTERMSEQUAL HOUSING
Call Direct: 414.712.6275WhatsApp
CallWhatsApp
For sale · 92 DAYS
$295,000$162/sqft

762 TOULON Drive

Kissimmee, FL

4 beds2 baths1,818 sqft

Courtesy of KELLER WILLIAMS ADVANTAGE III

For sale · 103 DAYS
$500,000$189/sqft

4701 RUBY RED LANE

Kissimmee, FL

7 beds5.5 baths2,646 sqft

Courtesy of RE/MAX TOWN & COUNTRY REALTY

$245/sqft

832 DRIVING RANGE Court

Kissimmee, FL

3 beds3.5 baths1,704 sqft

Courtesy of SDLP REAL ESTATE GROUP LLC

Kissimmee, FL

2 beds2 baths1,512 sqft

Courtesy of VELEZ COURTESY MANAGEMENT

1 bath
886 sqft

Courtesy of CAGAN MANAGEMENT GROUP INC

$230,000$163/sqft

525 CARLSBAD Drive

Kissimmee, FL

3 beds2 baths1,412 sqft

Courtesy of KELLER WILLIAMS REALTY AT THE PARKS

For rent · 124 DAYS
$2,000

4712 HEMINGWAY HOUSE Street

Kissimmee, FL

3 beds3.5 baths1,468 sqft

Courtesy of EATON REALTY SERVICES

For sale · 35 DAYS
$419,000$291/sqft

2530 MANESHAW Lane

Kissimmee, FL

3 beds3 baths1,440 sqft

Courtesy of EXP REALTY LLC

$154/sqft

1127 GARDANNE Court

Kissimmee, FL

3 beds2 baths1,720 sqft

Courtesy of ORIGINAL REALTY LLC

For rent · 43 DAYS
$4,500

502 GREENBRIER Avenue

Kissimmee, FL

4 beds3.5 baths2,534 sqft

Courtesy of 365 REALTY, INC.

For sale · 7 DAYS
$765,999$218/sqft

501 SUMNER Street

Kissimmee, FL

5 beds4 baths3,518 sqft

Courtesy of KELLER WILLIAMS LEGACY REALTY

For sale · 1 DAY
$459,990$230/sqft

4381 CREEKSIDE Boulevard

Kissimmee, FL

4 beds3.5 baths1,999 sqft

Courtesy of AXEN REALTY, LLC

For sale · 113 DAYS
$540,000$255/sqft

2590 BORINQUEN Drive

Kissimmee, FL

3 beds2 baths2,118 sqft

Courtesy of BRIGHT TRUST REALTY LLC

For sale · 87 DAYS
$134,900$184/sqft

1229 BERMUDA LAKES Lane #206

Kissimmee, FL

1 bed1 bath733 sqft

Courtesy of CHARLES RUTENBERG REALTY ORLANDO

For sale · 123 DAYS
$345,000$151/sqft

1944 THE OAKS Boulevard

Kissimmee, FL

4 beds2 baths2,288 sqft

Courtesy of PRESTIGE REALTY GROUP LLC

$239,600$179/sqft

625 DELMONTE Court

Kissimmee, FL

3 beds2 baths1,341 sqft

Courtesy of FIVE STAR REALTY & INVESTMENT GROUP

For sale · 6 DAYS
$334,900$179/sqft

1259 WISPY CYPRESS Drive

Kissimmee, FL

4 beds3.5 baths1,876 sqft

Courtesy of FORTEZA REALTY LLC

For sale · 76 DAYS
$469,000$207/sqft

8866 GENEVE Court

Kissimmee, FL

5 beds5.5 baths2,265 sqft

Courtesy of LA ROSA REALTY LLC

For sale · 18 DAYS
$1,938,000$565/sqft

2690 LAKE Road

Kissimmee, FL

6 beds5 baths3,429 sqft

Courtesy of REALTY ONE GROUP INSPIRATION

For sale · 18 DAYS
$1,938,000

0 SHARPEY Road

Kissimmee, FL

Courtesy of REALTY ONE GROUP INSPIRATION

$435,000$192/sqft

8838 GENEVE Court

Kissimmee, FL

5 beds5.5 baths2,263 sqft

Courtesy of ORLANDO REGIONAL PROPERTY MANAGEMENT

For sale · 120 DAYS
$410,000$230/sqft

2930 WHITE CEDAR Circle

Kissimmee, FL

3 beds2 baths1,782 sqft

Courtesy of EXP REALTY LLC

$385,000
Median list price
305
Active listings
91
Avg days on market
$360
Avg price per sqft

Active listings set the median price and the count. Recently sold homes set days on market and price per square foot. Refreshed hourly.