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HOMES FOR SALE · KISSIMMEE

Kissimmee 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.

Gina Morgandomellisa hayesAleanys CruzCaptivated Real EstateAshly Santiago
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976+ FAMILIES GUIDED · FL & WI
4216 ACTIVE LISTINGSLICENSED FL & WIHABLAMOS ESPAÑOL
LATEST IN KISSIMMEELIVE FROM THE MLS
4519 TRINITY Way #THC4, Kissimmee, FL 34746FOR RENT$2,5513 BEDS · 3.5 BATHS · 1,826 SQFT4519 TRINITY Way #THC4, Kissimmee, FL 347462428 DUBAI Street, Kissimmee, FL 34747FOR SALE$419,0002659 TRAFALGAR Boulevard, Kissimmee, FL 34758FOR SALE
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 SEP 10 · LIVE FROM THE MLS
4519 TRINITY Way #THC4, Kissimmee, FL 34746
4519 TRINITY Way #THC4, Kissimmee, FL 34746 2
4519 TRINITY Way #THC4, Kissimmee, FL 34746 3
FOR RENT · 713 DAYS
$2,551

4519 TRINITY Way #THC4

Kissimmee, FL

3 beds3.5 baths
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
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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
Pedro Rivera
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Pedro J Rivera, Broker & Founder
reThought Real Estate · Kissimmee, FL & Milwaukee, WI
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© 2026 PEDRO J RIVERA · BROKER, reTHOUGHT REAL ESTATE · LIC FL & WI
LIC FL & WIPRIVACYTERMSEQUAL HOUSING
Call Direct: 414.712.6275WhatsApp
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$489,999
$390,000
Median list price
280
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.

1,826 sqft

COURTESY OF THE APARTMENT BROTHERS LLC

2428 DUBAI Street, Kissimmee, FL 34747
2428 DUBAI Street, Kissimmee, FL 34747 2
2428 DUBAI Street, Kissimmee, FL 34747 3
FOR SALE · 708 DAYS
$419,000$185/sqft

2428 DUBAI Street

Kissimmee, FL

5 beds4 baths2,263 sqft

COURTESY OF SERHANT

2659 TRAFALGAR Boulevard, Kissimmee, FL 34758
2659 TRAFALGAR Boulevard, Kissimmee, FL 34758 2
2659 TRAFALGAR Boulevard, Kissimmee, FL 34758 3
FOR SALE · 424 DAYS
$489,999$211/sqft

2659 TRAFALGAR Boulevard

Kissimmee, FL

4 beds4.5 baths2,323 sqft

COURTESY OF LPT REALTY, LLC

2663 TRAFALGAR Boulevard, Kissimmee, FL 34758
2663 TRAFALGAR Boulevard, Kissimmee, FL 34758 2
2663 TRAFALGAR Boulevard, Kissimmee, FL 34758 3
FOR SALE · 581 DAYS
$489,999$202/sqft

2663 TRAFALGAR Boulevard

Kissimmee, FL

4 beds4.5 baths2,423 sqft

COURTESY OF LPT REALTY, LLC

4721 CLOCK TOWER Drive #108, Kissimmee, FL 34746
4721 CLOCK TOWER Drive #108, Kissimmee, FL 34746 2
4721 CLOCK TOWER Drive #108, Kissimmee, FL 34746 3
FOR SALE · 622 DAYS
$399,000$300/sqft

4721 CLOCK TOWER Drive #108

Kissimmee, FL

3 beds2 baths1,329 sqft

COURTESY OF GLASSTONE GROUP INC

4963 E PALL MALL Street, Kissimmee, FL 34758
4963 E PALL MALL Street, Kissimmee, FL 34758 2
4963 E PALL MALL Street, Kissimmee, FL 34758 3
FOR SALE · 678 DAYS
$409,999$279/sqft

4963 E PALL MALL Street

Kissimmee, FL

4 beds3.5 baths1,469 sqft

COURTESY OF LPT REALTY, LLC

4939 WORCHESTER Drive, Kissimmee, FL 34746
4939 WORCHESTER Drive, Kissimmee, FL 34746 2
4939 WORCHESTER Drive, Kissimmee, FL 34746 3
FOR SALE · 663 DAYS
$399,900$207/sqft

4939 WORCHESTER Drive

Kissimmee, FL

4 beds2 baths1,936 sqft

COURTESY OF LA ROSA REALTY KISSIMMEE

1676 TROPICAL PALMS Circle, Kissimmee, FL 34747
1676 TROPICAL PALMS Circle, Kissimmee, FL 34747 2
1676 TROPICAL PALMS Circle, Kissimmee, FL 34747 3
FOR SALE · 714 DAYS
$465,000$217/sqft

1676 TROPICAL PALMS Circle

Kissimmee, FL

4 beds5.5 baths2,145 sqft

COURTESY OF INTERNATIONAL REAL ESTATE LLC

2606 LODI Circle #105, Kissimmee, FL 34746
2606 LODI Circle #105, Kissimmee, FL 34746 2
2606 LODI Circle #105, Kissimmee, FL 34746 3
FOR SALE · 614 DAYS
$225,000$174/sqft

2606 LODI Circle #105

Kissimmee, FL

3 beds2 baths1,296 sqft

COURTESY OF GOLDEN DOOR REALTY

1864 CARIBBEAN VIEW Terrace, Kissimmee, FL 34747
1864 CARIBBEAN VIEW Terrace, Kissimmee, FL 34747 2
1864 CARIBBEAN VIEW Terrace, Kissimmee, FL 34747 3
FOR SALE · 613 DAYS
$785,000$180/sqft

1864 CARIBBEAN VIEW Terrace

Kissimmee, FL

9 beds7.5 baths4,363 sqft

COURTESY OF AGENT TRUST REALTY CORPORATION

2857 BOOKMARK Drive, Kissimmee, FL 34746
2857 BOOKMARK Drive, Kissimmee, FL 34746 2
2857 BOOKMARK Drive, Kissimmee, FL 34746 3
FOR SALE · 535 DAYS
$1,026,000$239/sqft

2857 BOOKMARK Drive

Kissimmee, FL

9 beds5 baths4,289 sqft

COURTESY OF PINEYWOODS REALTY LLC

5555 UNDISCLOSED, Kissimmee, FL 34741
5555 UNDISCLOSED, Kissimmee, FL 34741 2
5555 UNDISCLOSED, Kissimmee, FL 34741 3
FOR SALE · 375 DAYS
$300,000

5555 UNDISCLOSED

Kissimmee, FL

COURTESY OF SWEET HOMES REALTY LLC

2705 BUSHMAN Drive, Kissimmee, FL 34746
2705 BUSHMAN Drive, Kissimmee, FL 34746 2
2705 BUSHMAN Drive, Kissimmee, FL 34746 3
FOR SALE · 370 DAYS
$320,000$222/sqft

2705 BUSHMAN Drive

Kissimmee, FL

3 beds3 baths1,440 sqft

COURTESY OF PEOPLE'S CHOICE REALTY SVC LLC

4519 TRINITY Way #TH-C3, Kissimmee, FL 34746
4519 TRINITY Way #TH-C3, Kissimmee, FL 34746 2
4519 TRINITY Way #TH-C3, Kissimmee, FL 34746 3
FOR RENT · 711 DAYS
$2,296

4519 TRINITY Way #TH-C3

Kissimmee, FL

3 beds3.5 baths1,677 sqft

COURTESY OF THE APARTMENT BROTHERS LLC

2626 HAM BROWN Road #Emilia, Kissimmee, FL 34746
2626 HAM BROWN Road #Emilia, Kissimmee, FL 34746 2
2626 HAM BROWN Road #Emilia, Kissimmee, FL 34746 3
FOR RENT · 720 DAYS
$2,620

2626 HAM BROWN Road #Emilia

Kissimmee, FL

4 beds3.5 baths2,022 sqft

COURTESY OF THE APARTMENT BROTHERS LLC

2626 HAM BROWN Road #Magdalena, Kissimmee, FL 34746
2626 HAM BROWN Road #Magdalena, Kissimmee, FL 34746 2
2626 HAM BROWN Road #Magdalena, Kissimmee, FL 34746 3
FOR RENT · 720 DAYS
$2,670

2626 HAM BROWN Road #Magdalena

Kissimmee, FL

4 beds3.5 baths2,040 sqft

COURTESY OF THE APARTMENT BROTHERS LLC

448 NAPLES Court, Kissimmee, FL 34759
448 NAPLES Court, Kissimmee, FL 34759 2
FOR SALE · 547 DAYS
$44,000

448 NAPLES Court

Kissimmee, FL

COURTESY OF AMERICAN RESALES

MARTIGUES Drive, Kissimmee, FL 34759
MARTIGUES Drive, Kissimmee, FL 34759 2
FOR SALE · 632 DAYS
$54,000

MARTIGUES Drive

Kissimmee, FL

COURTESY OF AMERICAN RESALES

2744 BOOKMARK Drive, Kissimmee, FL 34746
2744 BOOKMARK Drive, Kissimmee, FL 34746 2
2744 BOOKMARK Drive, Kissimmee, FL 34746 3
FOR SALE · 694 DAYS
$598,800$182/sqft

2744 BOOKMARK Drive

Kissimmee, FL

5 beds5 baths3,292 sqft

COURTESY OF DECONOVA INTERNATIONAL GROUP

Kissimmee, FL 34759
Kissimmee, FL 34759 2
Kissimmee, FL 34759 3
FOR SALE · 699 DAYS
$254,500$195/sqft

Kissimmee, FL 34759

3 beds2 baths1,308 sqft

COURTESY OF CAVENDISH REALTY

8713 ROCKINGHAM Terrace #D, Kissimmee, FL 34747
8713 ROCKINGHAM Terrace #D, Kissimmee, FL 34747 2
8713 ROCKINGHAM Terrace #D, Kissimmee, FL 34747 3
FOR SALE · 539 DAYS
$250,000$216/sqft

8713 ROCKINGHAM Terrace #D

Kissimmee, FL

2 beds2 baths1,157 sqft

COURTESY OF RESOURCE ONE REALTY

4189 PARAGRAPH Drive, Kissimmee, FL 34746
4189 PARAGRAPH Drive, Kissimmee, FL 34746 2
4189 PARAGRAPH Drive, Kissimmee, FL 34746 3
FOR SALE · 719 DAYS
$980,000$228/sqft

4189 PARAGRAPH Drive

Kissimmee, FL

8 beds5 baths4,289 sqft

COURTESY OF SCATES REALTY & INVESTMENT PRO

8612 LA ISLA Drive, Kissimmee, FL 34747
8612 LA ISLA Drive, Kissimmee, FL 34747 2
8612 LA ISLA Drive, Kissimmee, FL 34747 3
FOR SALE · 726 DAYS
$460,000$199/sqft

8612 LA ISLA Drive

Kissimmee, FL

5 beds4 baths2,317 sqft

COURTESY OF AMERICAN IDEAL HOMES, LLC

PINE NEEDLE Trail, Kissimmee, FL 34746FOR SALE · 499 DAYS
$185,000

PINE NEEDLE Trail

Kissimmee, FL

COURTESY OF LA ROSA REALTY KISSIMMEE

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