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.

2,965 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
2965 ACTIVE LISTINGSLICENSED FL & WIHABLAMOS ESPAÑOL
LATEST IN KISSIMMEELIVE FROM THE MLS
2717 SKYLINE Loop, Kissimmee, FL 34758For rent$1,9503 BEDS · 3.5 BATHS · 1,834 SQFT2717 SKYLINE Loop, Kissimmee, FL 347585637 LE MARIN Way, Kissimmee, FL 34758For rent$2,450337 MARCELLO Boulevard, Kissimmee, FL 34746For sale$425,000
2717 SKYLINE Loop, Kissimmee, FL 34758
2717 SKYLINE Loop, Kissimmee, FL 34758 2
2717 SKYLINE Loop, Kissimmee, FL 34758 3
For rent
$1,950

2717 SKYLINE Loop

Kissimmee, FL

3 beds3.5 baths1,834 sqft

Courtesy of REALTY ONE GROUP ESTATES

5637 LE MARIN Way, Kissimmee, FL 34758
5637 LE MARIN Way, Kissimmee, FL 34758 2
5637 LE MARIN Way, Kissimmee, FL 34758 3
337 MARCELLO Boulevard, Kissimmee, FL 34746
337 MARCELLO Boulevard, Kissimmee, FL 34746 2
337 MARCELLO Boulevard, Kissimmee, FL 34746 3
2237 RITA Lane, Kissimmee, FL 34744
2237 RITA Lane, Kissimmee, FL 34744 2
2237 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990$226/sqft
2235 RITA Lane, Kissimmee, FL 34744
2235 RITA Lane, Kissimmee, FL 34744 2
2235 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990$226/sqft
2233 RITA Lane, Kissimmee, FL 34744
2233 RITA Lane, Kissimmee, FL 34744 2
2233 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990$226/sqft
2231 RITA Lane, Kissimmee, FL 34744
2231 RITA Lane, Kissimmee, FL 34744 2
2231 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990
2229 RITA Lane, Kissimmee, FL 34744
2229 RITA Lane, Kissimmee, FL 34744 2
2229 RITA Lane, Kissimmee, FL 34744 3
For sale · 17 DAYS
$352,990
2223 RITA Lane, Kissimmee, FL 34744
2223 RITA Lane, Kissimmee, FL 34744 2
2223 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990
2221 RITA Lane, Kissimmee, FL 34744
2221 RITA Lane, Kissimmee, FL 34744 2
2221 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990
2219 RITA Lane, Kissimmee, FL 34744
2219 RITA Lane, Kissimmee, FL 34744 2
2219 RITA Lane, Kissimmee, FL 34744 3
For sale · 45 DAYS
$336,990
225 SOUTHBRIDGE Circle, Kissimmee, FL 34744
225 SOUTHBRIDGE Circle, Kissimmee, FL 34744 2
225 SOUTHBRIDGE Circle, Kissimmee, FL 34744 3
1530 BARBERRY Drive, Kissimmee, FL 34744
1530 BARBERRY Drive, Kissimmee, FL 34744 2
1530 BARBERRY Drive, Kissimmee, FL 34744 3
2747 CALLAWAY Lane, Kissimmee, FL 34744
2747 CALLAWAY Lane, Kissimmee, FL 34744 2
2747 CALLAWAY Lane, Kissimmee, FL 34744 3
2718 CLUB CORTILE Circle #B, Kissimmee, FL 34746
2718 CLUB CORTILE Circle #B, Kissimmee, FL 34746 2
2718 CLUB CORTILE Circle #B, Kissimmee, FL 34746 3
2764 BOOKMARK Drive, Kissimmee, FL 34746
2764 BOOKMARK Drive, Kissimmee, FL 34746 2
2764 BOOKMARK Drive, Kissimmee, FL 34746 3
2460 WHITE POPPY Drive, Kissimmee, FL 34747
2460 WHITE POPPY Drive, Kissimmee, FL 34747 2
2460 WHITE POPPY Drive, Kissimmee, FL 34747 3
2104 BROOME Street, Kissimmee, FL 34743
2104 BROOME Street, Kissimmee, FL 34743 2
2104 BROOME Street, Kissimmee, FL 34743 3
For sale · 14 DAYS
$349,990
3038 PARKWAY Boulevard #306, Kissimmee, FL 34747
3038 PARKWAY Boulevard #306, Kissimmee, FL 34747 2
3038 PARKWAY Boulevard #306, Kissimmee, FL 34747 3
4432-4436-4440- SUMMER FLOWERS Place, Kissimmee, FL 34746
4432-4436-4440- SUMMER FLOWERS Place, Kissimmee, FL 34746 2
4432-4436-4440- SUMMER FLOWERS Place, Kissimmee, FL 34746 3
4440 SUMMER FLOWERS Place, Kissimmee, FL 34746
4440 SUMMER FLOWERS Place, Kissimmee, FL 34746 2
4440 SUMMER FLOWERS Place, Kissimmee, FL 34746 3
2750 BIG TIMBER Drive, Kissimmee, FL 34758
2750 BIG TIMBER Drive, Kissimmee, FL 34758 2
2750 BIG TIMBER Drive, Kissimmee, FL 34758 3
3000 MAINGATE Lane #219, Kissimmee, FL 34747
3000 MAINGATE Lane #219, Kissimmee, FL 34747 2
3000 MAINGATE Lane #219, Kissimmee, FL 34747 3
For sale · 46 DAYS
3881 BOWFIN Trail, Kissimmee, FL 34746
3881 BOWFIN Trail, Kissimmee, FL 34746 2
3881 BOWFIN Trail, Kissimmee, FL 34746 3
See 2,965 homes
← PreviousPage 34 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 rent · 9 DAYS
$2,450

5637 LE MARIN Way

Kissimmee, FL

4 beds3 baths2,109 sqft

Courtesy of NOVALUX REALTY, LLC.

For sale · 44 DAYS
$425,000$230/sqft

337 MARCELLO Boulevard

Kissimmee, FL

4 beds3 baths1,848 sqft

Courtesy of VICARI REALTY CORP

2237 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

2235 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

2233 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$226/sqft

2231 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$237/sqft

2229 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$226/sqft

2223 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$226/sqft

2221 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

$226/sqft

2219 RITA Lane

Kissimmee, FL

3 beds3.5 baths1,489 sqft

Courtesy of DR HORTON REALTY OF CENTRAL FLORIDA LLC

For sale · 50 DAYS
$330,000$257/sqft

225 SOUTHBRIDGE Circle

Kissimmee, FL

3 beds2 baths1,284 sqft

Courtesy of OPENDOOR BROKERAGE LLC

For rent · 47 DAYS
$3,200

1530 BARBERRY Drive

Kissimmee, FL

4 beds3 baths2,374 sqft

Courtesy of HOUSY REALTY INC

For sale · 52 DAYS
$365,000$223/sqft

2747 CALLAWAY Lane

Kissimmee, FL

4 beds2 baths1,639 sqft

Courtesy of MARK SPAIN REAL ESTATE

For sale · 50 DAYS
$199,000$165/sqft

2718 CLUB CORTILE Circle #B

Kissimmee, FL

3 beds2 baths1,204 sqft

Courtesy of KELLER WILLIAMS ELITE PARTNERS III REALTY

For sale · 45 DAYS
$598,500$182/sqft

2764 BOOKMARK Drive

Kissimmee, FL

5 beds5 baths3,292 sqft

Courtesy of DECONOVA INTERNATIONAL GROUP

For sale · 51 DAYS
$560,000$213/sqft

2460 WHITE POPPY Drive

Kissimmee, FL

6 beds3 baths2,626 sqft

Courtesy of LA ROSA REALTY CENTRAL FLORIDA LLC

$241/sqft

2104 BROOME Street

Kissimmee, FL

3 beds3.5 baths1,452 sqft

Courtesy of AXEN REALTY, LLC

For rent · 51 DAYS
$1,300

3038 PARKWAY Boulevard #306

Kissimmee, FL

2 beds2 baths937 sqft

Courtesy of SUNSHINE PREMIUM PROPERTIES

For sale · 10 DAYS
$1,310,000$194/sqft

4432-4436-4440- SUMMER FLOWERS Place

Kissimmee, FL

16 beds12 baths6,768 sqft

Courtesy of KELLER WILLIAMS LEGACY REALTY

For sale · 1 DAY
$325,000$197/sqft

4440 SUMMER FLOWERS Place

Kissimmee, FL

4 beds3.5 baths1,650 sqft

Courtesy of KELLER WILLIAMS LEGACY REALTY

For sale · 1 DAY
$399,000$142/sqft

2750 BIG TIMBER Drive

Kissimmee, FL

5 beds4.5 baths2,801 sqft

Courtesy of MY REALTY GROUP, LLC.

$47,000$155/sqft

3000 MAINGATE Lane #219

Kissimmee, FL

1 bed1 bath304 sqft

Courtesy of PROPERTIES IN TOWN

For sale · 12 DAYS
$419,900$166/sqft

3881 BOWFIN Trail

Kissimmee, FL

3 beds3.5 baths2,533 sqft

Courtesy of LPT REALTY, LLC

$385,000
Median list price
306
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.