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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.

Pedro Rivera
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976+ FAMILIES GUIDED · FL & WI
4323 ACTIVE LISTINGSLICENSED FL & WIHABLAMOS ESPAÑOL
LATEST IN KISSIMMEELIVE FROM THE MLS
4001 SANTA MARIA Drive #107, Kissimmee, FL 34741FOR SALE$253,0004 BEDS · 3 BATHS · 1,470 SQFT4001 SANTA MARIA Drive #107, Kissimmee, FL 347411035 JASON RIDGE Court, Kissimmee, FL 34747FOR SALE$415,0002239 SANTA LUCIA Street, Kissimmee, FL 34743FOR SALE$338,497
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 26 · LIVE FROM THE MLS
$384,900
Median list price
287
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.

4001 SANTA MARIA Drive #107, Kissimmee, FL 34741
4001 SANTA MARIA Drive #107, Kissimmee, FL 34741 2
4001 SANTA MARIA Drive #107, Kissimmee, FL 34741 3
FOR SALE
$253,000$172/sqft

4001 SANTA MARIA Drive #107

Kissimmee, FL

4 beds3 baths1,470 sqft

COURTESY OF IMPERIAL REALTY CENTRAL FL.

1035 JASON RIDGE Court, Kissimmee, FL 34747
1035 JASON RIDGE Court, Kissimmee, FL 34747 2
1035 JASON RIDGE Court, Kissimmee, FL 34747 3
2239 SANTA LUCIA Street, Kissimmee, FL 34743
2239 SANTA LUCIA Street, Kissimmee, FL 34743 2
2239 SANTA LUCIA Street, Kissimmee, FL 34743 3
FOR SALE · 337 DAYS
$338,497$320/sqft

2239 SANTA LUCIA Street

Kissimmee, FL

8911 TROPICAL HAVEN Court, Kissimmee, FL 34747
8911 TROPICAL HAVEN Court, Kissimmee, FL 34747 2
8911 TROPICAL HAVEN Court, Kissimmee, FL 34747 3
4307 PEBBLES THROW Drive, Kissimmee, FL 34746
4307 PEBBLES THROW Drive, Kissimmee, FL 34746 2
4307 PEBBLES THROW Drive, Kissimmee, FL 34746 3
23 PETERLEE Court, Kissimmee, FL 34758
23 PETERLEE Court, Kissimmee, FL 34758 2
23 PETERLEE Court, Kissimmee, FL 34758 3
FOR SALE
$305,000$179/sqft

23 PETERLEE Court

Kissimmee, FL

4 beds
647 HERALDO Court, Kissimmee, FL 34758FOR SALE
$274,900$158/sqft

647 HERALDO Court

Kissimmee, FL

4 beds2 baths1,744 sqft

COURTESY OF PROPERTY LOGIC RE

4754 BLUE DIAMOND Street, Kissimmee, FL 34746
4754 BLUE DIAMOND Street, Kissimmee, FL 34746 2
4754 BLUE DIAMOND Street, Kissimmee, FL 34746 3
1407 TITIAN Court, Kissimmee, FL 34747
1407 TITIAN Court, Kissimmee, FL 34747 2
1407 TITIAN Court, Kissimmee, FL 34747 3
663 JAGUAR Court, Kissimmee, FL 34759
663 JAGUAR Court, Kissimmee, FL 34759 2
663 JAGUAR Court, Kissimmee, FL 34759 3
127 AURELIA Court, Kissimmee, FL 34758FOR SALE
$269,900$156/sqft

127 AURELIA Court

Kissimmee, FL

3 beds2 baths1,731 sqft

COURTESY OF OLYMPUS EXECUTIVE REALTY INC

3023 RIO GRANDE Trail #3023, Kissimmee, FL 34741
3023 RIO GRANDE Trail #3023, Kissimmee, FL 34741 2
3023 RIO GRANDE Trail #3023, Kissimmee, FL 34741 3
1705 EVERGREEN Street, Kissimmee, FL 34746
1705 EVERGREEN Street, Kissimmee, FL 34746 2
1705 EVERGREEN Street, Kissimmee, FL 34746 3
FOR SALE
$180,000$346/sqft

1705 EVERGREEN Street

Kissimmee, FL

2 beds2 baths520 sqft

COURTESY OF LPT REALTY, LLC

307 COLONY Court, Kissimmee, FL 34758
307 COLONY Court, Kissimmee, FL 34758 2
307 COLONY Court, Kissimmee, FL 34758 3
2421 RUDDENSTONE Way, Kissimmee, FL 34744
2421 RUDDENSTONE Way, Kissimmee, FL 34744 2
2421 RUDDENSTONE Way, Kissimmee, FL 34744 3
1713 SOUTHFORK Drive, Kissimmee, FL 34744
1713 SOUTHFORK Drive, Kissimmee, FL 34744 2
1713 SOUTHFORK Drive, Kissimmee, FL 34744 3
301 LESESNE Street, Kissimmee, FL 34744
301 LESESNE Street, Kissimmee, FL 34744 2
301 LESESNE Street, Kissimmee, FL 34744 3
2146 CYPRESS BAY Boulevard, Kissimmee, FL 34743
2146 CYPRESS BAY Boulevard, Kissimmee, FL 34743 2
FOR RENT
$1,600

2146 CYPRESS BAY Boulevard

Kissimmee, FL

2 beds2 baths1,000 sqft

COURTESY OF REMAX PREMIER PROPERTIES

22 CLYDE Avenue #4, Kissimmee, FL 34741
22 CLYDE Avenue #4, Kissimmee, FL 34741 2
22 CLYDE Avenue #4, Kissimmee, FL 34741 3
FOR RENT
$975

22 CLYDE Avenue #4

Kissimmee, FL

1 beds1 baths500 sqft

COURTESY OF WEICHERT REALTORS HALLMARK PRO

22 CLYDE Avenue #5, Kissimmee, FL 34741
22 CLYDE Avenue #5, Kissimmee, FL 34741 2
22 CLYDE Avenue #5, Kissimmee, FL 34741 3
FOR RENT
$1,175

22 CLYDE Avenue #5

Kissimmee, FL

2 beds1 baths1,023 sqft
2154 CYPRESS BAY Boulevard, Kissimmee, FL 34743
2154 CYPRESS BAY Boulevard, Kissimmee, FL 34743 2
2154 CYPRESS BAY Boulevard, Kissimmee, FL 34743 3
FOR RENT
$1,600

2154 CYPRESS BAY Boulevard

Kissimmee, FL

2 beds2 baths1,000 sqft

COURTESY OF REMAX PREMIER PROPERTIES

22 CLYDE Avenue #6, Kissimmee, FL 34741
22 CLYDE Avenue #6, Kissimmee, FL 34741 2
22 CLYDE Avenue #6, Kissimmee, FL 34741 3
FOR RENT
$1,175

22 CLYDE Avenue #6

Kissimmee, FL

2 beds1 baths1,023 sqft
482 PRESTWICK Place, Kissimmee, FL 34759
482 PRESTWICK Place, Kissimmee, FL 34759 2
482 PRESTWICK Place, Kissimmee, FL 34759 3
FOR SALE
Kissimmee, FL 34743
Kissimmee, FL 34743 2
Kissimmee, FL 34743 3
FOR RENT
$2,310

Kissimmee, FL 34743

3 beds2 baths1,775 sqft

COURTESY OF PROGRESS RESIDENTIAL PROP

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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.

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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
REAL ESTATE
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Pedro J Rivera, Broker & Founder
reThought Real Estate · Kissimmee, FL & Milwaukee, WI
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FOR SALE
$415,000$240/sqft

1035 JASON RIDGE Court

Kissimmee, FL

4 beds2 baths1,727 sqft

COURTESY OF MOBED REALTY, P.A.

3 beds
2 baths
1,059 sqft

COURTESY OF BLUE KEY PROPERTY MANAGEMENT

FOR SALE
$999,995$229/sqft

8911 TROPICAL HAVEN Court

Kissimmee, FL

9 beds7.5 baths4,363 sqft

COURTESY OF SUNTRAN INTNL CORPORATION

FOR SALE
$630,000$218/sqft

4307 PEBBLES THROW Drive

Kissimmee, FL

5 beds3.5 baths2,896 sqft

COURTESY OF REALTY OF AMERICA

2 baths
1,704 sqft

COURTESY OF OPENDOOR BROKERAGE LLC

FOR SALE
$549,900$169/sqft

4754 BLUE DIAMOND Street

Kissimmee, FL

5 beds5.5 baths3,257 sqft

COURTESY OF MARK SPAIN REAL ESTATE

FOR SALE
$849,999$370/sqft

1407 TITIAN Court

Kissimmee, FL

4 beds3 baths2,295 sqft

COURTESY OF TOP TIER RESORT REALTY

FOR SALE · 756 DAYS
$239,900$183/sqft

663 JAGUAR Court

Kissimmee, FL

3 beds2 baths1,308 sqft

COURTESY OF CHARLES RUTENBERG REALTY ORLANDO

FOR RENT · 44 DAYS
$1,750

3023 RIO GRANDE Trail #3023

Kissimmee, FL

3 beds2 baths1,250 sqft

COURTESY OF KELLER WILLIAMS ADVANTAGE III

FOR SALE · 141 DAYS
$260,000$145/sqft

307 COLONY Court

Kissimmee, FL

3 beds2 baths1,790 sqft

COURTESY OF KELLER WILLIAMS REALTY SMART 1

FOR SALE
$375,000$240/sqft

2421 RUDDENSTONE Way

Kissimmee, FL

3 beds2 baths1,560 sqft

COURTESY OF MILA REALTY

FOR RENT
$2,500

1713 SOUTHFORK Drive

Kissimmee, FL

3 beds2 baths1,508 sqft

COURTESY OF AGENT TRUST REALTY CORPORATION

FOR RENT
$2,190

301 LESESNE Street

Kissimmee, FL

3 beds2 baths1,375 sqft

COURTESY OF LPT REALTY, LLC

COURTESY OF WEICHERT REALTORS HALLMARK PRO

COURTESY OF WEICHERT REALTORS HALLMARK PRO

$99,900$133/sqft

482 PRESTWICK Place

Kissimmee, FL

1 beds2.5 baths750 sqft

COURTESY OF HOUSEWELL.COM REALTY OF FLORIDA LLC