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About This Home

This 4-bedroom, 5-bathroom single family at 2540 WINNERS CIRCLE in KISSIMMEE, FL is listed for $739,000 ($228 per sqft). Built in 2000, the home offers 3,246 sqft of living space on a 0.50 acres lot.

Agent Description

**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**

Key Features

  • Built in 2000
  • 0.50 acre lot
  • Private pool

Property Details

4 full, 1 half
2000

Amenities

PoolRV Parking

Monthly Cost Estimate

$3,952/mo

20% down · 6.5% · 30 years

Principal$534
Interest$3,202
Insurance$216

Estimates only. Actual payments may vary.

Location

2540 WINNERS CIRCLE

KISSIMMEE, FL 34744

WINNERS PARK

Features & Amenities

Interior Features

Ceiling Fans(s)Eat-in KitchenKitchen/Family Room ComboLiving Room/Dining Room ComboPrimarybedroom UpstairsSolid Surface CountersStone CountersWalk-in Closet(s)Window Treatments

Exterior Features

PavedHurricane ShuttersLightingPrivate MailboxRain GuttersSliding DoorsStoragePool

Property Details

Flooring

CarpetTile

Construction

BlockStucco

Parking

BoatDrivewayGarageGarage - AttachedGolf CartGuestOn StreetOversizedRV

Heating

CentralElectric (Heating)

Cooling

Central Air

Appliances

DishwasherDryerMicrowaveRangeRefrigeratorWasherWater - Softener

Questions & Answers

This 4-bedroom, 5-bathroom single family at 2540 WINNERS CIRCLE is listed at $739,000 ($228/sqft). The estimated monthly payment is $3,202 based on 20% down at 6.5% interest.

Key features include: Built in 2000, 0.50 acre lot, Private pool. Interior Features: Ceiling Fans(s), Eat-in Kitchen, Kitchen/Family Room Combo. Exterior Features: Paved, Hurricane Shutters, Lighting.

This property is listed by Jenny Wemert and can be reached at 4074128488 or listingteam@wemertgrouprealty.com.

JW

Jenny Wemert

Agent at WEMERT GROUP REALTY LLC

(407) 412-8488

Listed by WEMERT GROUP REALTY LLC · View on Broker Site

MLS# O6382446· Source: listhub· Updated 50 days ago

Copyright © 2026 Stellar MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

2540 WINNERS CIRCLE, KISSIMMEE, FL 34744

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