by Global Lifestyle Properties

Check Availability
$625,000
● House - For Sale

2540 WINNERS CIRCLE

KISSIMMEE, FL 34744
bedrooms
4 Beds
bathrooms
4 Baths, 1 Half Bath
square feet
3,246 Ft²
$3,377
Est. Monthly

About This Property

Virtually Staged. **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**
Unit Size
3,246 Ft²
Days on Market
226 days
Land Size
0.50 acres
Price per sqft
$193
Property Type
House
Property Taxes
$307
HOA Dues
-
Year Built
2000

Listed By

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Last updated: 18 days ago (Stellar MLS #O6382446)

Price History

Date / Event Date Event Price
Sep 16, 2026 Relisted $625,000
Relisted
Jul 7, 2026 In contract -
In contract
Jul 4, 2026 Price Decreased $650,000
↓ $39K (5.7%)
Price Decreased
Jun 24, 2026 Price Decreased $689,000
↓ $10K (1.4%)
Price Decreased
May 29, 2026 Price Decreased $699,000
↓ $26K (3.6%)
Price Decreased
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Property Highlights

Garage
Parking Available
Air Conditioning
Parking Details
Has Garage
Attached Garage
Has Open Parking
Parking Features: Boat, Driveway, Garage Door Opener, Golf Cart Garage, Guest, On Street, Oversized, Parking Pad, RV Access/Parking, Curb Parking, Ground Level
Garage Spaces: 4
Interior Details
Half Bathrooms: 1
Full Bathrooms: 4
Interior Features: Ceiling Fan(s), Stone Counters, Walk-In Closet(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Living Room/Dining Room Combo, PrimaryBedroom Upstairs, Solid Surface Counters, Window Treatments
Appliances: Dishwasher, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer, Water Purifier, Water Softener
Flooring Type: Carpet, Tile
Door Features: Sliding Doors
Laundry Features: In Garage
Rooms: 12
Exterior Details
Square Footage: 3246
Square Footage Source: $0
Year Built: 2000
Building Area Total: 3710
Levels: Two
Other Structures: Other, Shed(s), Workshop
Building Area Units: Square Feet
Window Features: Aluminum Frames, Blinds, Double Pane Windows, ENERGY STAR Qualified Windows, Thermal Windows
Construction Materials: Block, Stucco
Patio and Porch Features: Covered, Enclosed, Front Porch, Patio, Rear Porch
Pool Features: Gunite, In Ground, Screen Enclosure, Auto Cleaner, Lighting
Pool is Private
Lot Features: Cul-De-Sac, Landscaped, Oversized Lot, Street Dead-End
Lot Size Area: 21824
Lot Size Units: Square Feet
Lot Size Acres: 0.5
Lot Size Square Feet: 21824
Tax Lot: 6
Water Source: Public
Financial Details
Tax Annual Amount: $3,688
Lease Considered: Yes
Utilities Details
Cooling Type: Central Air
Heating Type: Central, Electric
Sewer : Septic Tank

Building Info

Overview

    General

  • Year Built: 2000
  • Effective Year Built: 2000
  • Building Count: 1
  • Bedroom Count: 4
  • Bathroom Count: 4
  • Full Bathrooms: 3
  • Partial Bathrooms: 4
  • Building Condition: 3
  • Building Quality: 4
  • Construction Type: 12
  • Building Style: 15
  • Exterior Walls Type: 7
  • Interior Walls Type: 3
  • Roof Shape Type: 7
  • Roof Cover Type: 4
  • Floor Count: 200
  • Living Units: 1
  • Floor Cover: 9
  • Basement Type: 0
  • Basement Area: 0
  • Garage Type: 1
  • Garage Square Area: 400
  • Parking Space Count: 2
  • Patio Type: 8
  • Porch Type: 35
  • Pool Type: 12

    Dimensions

  • Lot Size Square Feet: 21,823
  • Total Building Area: 3,646
  • Gross Building Area: 3,710
  • Building Area: 3,246
  • Building Area Measurement: L

    Heating and Cooling

  • Air Conditioning: 4
  • Heating: 24
  • Heated Square Feet: 3,246
  • Heating Fuel Type: 0

    Utilities

  • Sewer System: 0
  • Water Service: 0

Building

  • Building Type: 0
  • Property Class: R
  • Subdivision: WINNERS PARK
  • Land Acres: 0000000501
  • Standard Land Use Code: 1001
  • County Land Use Code: 0111
  • State Land Use Code: 0111
  • Legal Description 1: WINNERS PARK PB 7 PG 48 LOT 6

Neighborhood

  • School District Name: Osceola County School District
  • Census Tract: 042800

Zoning

  • Zoning: OR1C

Geography

  • Assessors Map Reference: 13-17
  • Subdivision Tract Number: 5515
  • Parcel: 17-25-30-5515-0001-0060
  • Block: 60
  • Lot: 6
  • Meridian: SEC 17 TWN 25S RNG 30E
  • Municipality: WINNERS PARK MSTU
  • Latitude: 28.3077
  • Longitude: -81.3409

    Address

  • Full Address: 2540 Winners Cir
  • Address - House Number: 2540
  • Address - Street Name: Winners
  • Address - Suffix Type: Cir
  • State: FL
  • City Name: Kissimmee
  • Carrier Code: R022
  • 4-Digit Zip Code: 3987
  • Zip Code: 34744

Valuation

    Tax

  • Total Area: 3,710
  • Tax Year: 2022
  • Tax Amount: $327,737
  • Tax Rate Code Area: 344

    Appraisal Valuation

  • Standard Deviation: 0.151
  • Valuation Date: Jan 03, 2024
  • Confidence Score: 81
  • Final Value: 528,169
  • High Value: 607,949
  • Low Value: 448,388

    Market Valuation

  • Market Total Value: $334,300
  • Market Land Value: $55,000
  • Market Improvement Value: $279,300

    Assessments Valuation

  • Assessed Year: 2022
  • Assessed Total Value: $209,442

    Exemptions

  • Homeowner Exemption: Yes

    Sales

  • Current Sale Contract Date: Apr 16, 2003
  • Current Sale Recording Date: May 01, 2003
  • Current Sale Price:
  • Current Sale Document Type: 71
  • Previous Sale Recording Date: Jan 08, 1999
  • Previous Sale Contract Date: Dec 31, 1998
  • Previous Sale Document Type: 71

    Financing

  • First Mortgage Financing Type: FIX
Data used for valuation calculations is provided by RealtyHop, and other third party sources

Comparables

Unit
Status
Type
Beds
Baths
ft²
Price/ft²
Asking Price
Listed On
Closing Price
Sold On
HOA + Taxes

About Bluegrass Estates


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Frequently Asked Questions

When was property at 2540 Winners Circle built and last sold?
The property at 2540 Winners Circle was built in 2000 and last sold on Apr 16, 2003 for $196,000.
How much is this home worth?
The estimated value of the home located at 2540 Winners Circle is $634,272.
What are some comparable homes to 2540 Winners Circle?
There are currently no comparable homes to 2540 Winners Circle.