Gabriella Massaro

Gabriella Massaro Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

$739,000.00
2540 WINNERS CIRCLE, KISSIMMEE, FL - 34744
4 beds
4.5 baths
3,246 sqft
$739,000.00
2540 WINNERS CIRCLE, KISSIMMEE, FL - 34744
Gabriella Massaro
$739,000.00
4 beds
4.5 baths
3,246 sqft
2540 WINNERS CIRCLE, KISSIMMEE, FL - 34744
For Sale
Photo 1
  • Built in 2000
  • 4 garage spaces
  • $227.66/sqft
  • Lot size: 21,824 sqft
  • 38 days on market

**WELCOME HOME** NO HOA, HALF AN ACRE of land, a PRIVATE POOL, and a full SEPARATE APARTMENT on the main floor – welcome to your next chapter on Winners Circle in the Winners Park community of Kissimmee! EXTERIOR PAINT (2023), NEW WINDOWS (2022), DETACHED AIR CONDITIONED GARAGE (2022), septic tank serviced (2022) – big-ticket items are already started, giving you confidence and flexibility from day one. Situated on an expansive .50 ACRE LOT, this spacious two-story POOL HOME delivers over 3,000 square feet of living space, mature landscaping, a TILE ROOF, long paver driveway, and standout curb appeal. The SCREENED POOL with PAVER DECK creates a private backyard retreat with room to entertain, garden, or just spread out. Inside, the flexible layout is ideal for large households, multi-generational living, or anyone needing versatile space. The full first-floor apartment includes its own kitchen open to a living area, bedroom, and full bath – perfect for in-laws, guests, extended stays, or even creative work from home options! The main home features comfortable formal and family spaces, a well-equipped kitchen with casual dining, and an expansive FLORIDA ROOM complete with a full bath and cozy office space – offering endless possibilities for hobbies, remote work, or additional entertaining. Upstairs, a BONUS/LOFT anchors the remaining bedrooms, while the generous PRIMARY SUITE provides a peaceful escape with an updated private en-suite bath. Car enthusiasts, hobbyists, or entrepreneurs will appreciate the two-car attached garage plus the like-new detached, air-conditioned garage – currently used as a dojo, but easily transformed into a workshop, craft studio, gym, or business space. Updated yet still offering room to personalize, this home offers the rare combination of space, privacy, flexibility, and location. Perfectly situated just off Simpson Road, you will enjoy easy access to the Florida Turnpike, shopping, dining, area lakes, attractions, and world-famous theme parks – all while coming home to a quiet, established neighborhood with no HOA restrictions. Room to grow inside and out. Versatility for today and tomorrow. Schedule your tour today and be the winner on Winners Circle! **Seller may consider buyer concessions if made in an offer**

  • Directions: From 527A/Boggy Creek Rd, Turn right onto Simpson Rd, Turn left onto Winners Cir. Home will be on the right.
  • County: Osceola
  • Geo subdivision: WINNERS PARK

Nearby Schools

East Lake Elem

Neptune Middle (6-8)

Tohopekaliga High School

Features

Financial

Let's get in touch!

Gabriella Massaro

Gabriella Massaro

Real Estate Agent & Mortgage Loan Originator 🇺🇸 NMLS #2744990

See also

For Sale
4408 BREEZE ISLE LANE, KISSIMMEE, FL - 34744
$675,000.00
5 bds
3.5 ba
3,267 sqft
4408 BREEZE ISLE LANE, KISSIMMEE, FL - 34744
For Sale
3232 STONEWYCK STREET, ORLANDO, FL - 32824
$700,000.00
4 bds
4.0 ba
3,098 sqft
3232 STONEWYCK STREET, ORLANDO, FL - 32824
For Sale
860 SHORE DRIVE, KISSIMMEE, FL - 34744
$775,000.00
4 bds
2.5 ba
2,380 sqft
860 SHORE DRIVE, KISSIMMEE, FL - 34744
Stellar MLS
  • Source: Stellar MLS
  • MLS #: O6382446
Listing updated: March 29, 2026 at 7:05PM
Listing provided by: Jenny Wemert, WEMERT GROUP REALTY LLC
Last checked 19 hours ago
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