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Overview

3 bd2 ba1,914 sqft2 car garageSingle Family
TypeSingle Family
HOANone listed
Built1999
Lot109,466 sqft
Living area1,914 sqft
Price / sqft$285
Garage2 car

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About this home

Ceiling Fans(s)Rain GuttersDryerMicrowaveRangeRefrigeratorWasher

2507 Winners Cir is a 1999-built home in D S Estates, Kissimmee. Inside you'll find 3 bedrooms, 2 bathrooms, and 1,914 square feet of living space. Listed at $545,000 (about $285/sqft), 188 days on market. Flood zone X - outside the FEMA high-risk areas, which keeps insurance manageable.

From the listing

Now listed below recently appraised value and recent inspection completed! Available again, buyer financing fell through. Welcome home to 2.5 acres of private Florida living! This charming 3-bedroom, 2-bathroom block home in Kissimmee offers the rare combination of expansive acreage and ultimate convenience, all with NO HOA. Located just moments from Osceola Heritage Park and offering quick access to major thoroughfares, this property is perfectly situated for easy commuting and entertainment. The original owners have meticulously maintained and updated the residence, ensuring move-in readiness. Significant recent improvements include a NEW ROOF in 2018, a NEW 4 TON HVAC SYSTEM with a Ditek Surge Protector installed in 2022, NEW Water Heater 2026, an exterior repaint in 2025, and a new septic pump and service in early 2026. Additionally, enjoy the freshly rescreened porch and new vinyl privacy fencing. The home was also built with Pest Tubes in the walls and filled quarterly. Step inside to find vaulted ceilings and three skylights illuminating the open living areas, which feature a formal living room with a bay window and a cozy family room complete with a wood-burning fireplace. The primary suite offers a private retreat with a double pocket sliding glass door leading to the lanai, and a spacious bath featuring a double vanity, walk-in shower, and soaker tub. The home features a mix of laminate in the bedrooms and living/dining areas and tile in the kitchen and baths for ease of maintenance. Enjoy the tranquil Florida outdoors from the screened lanai, complete with new fans and a durable Chattanooga Rock floor, which provides scenic views of trees and wilderness on your 2.5-acre lot. The back of the home features an extended paver patio perfect for outdoor entertaining. Additionally, if a pool is in your future plans, the second guest bath includes a convenient door leading directly to the patio.

The essentials

Built
1999
Price / sqft
$285
On market
188 days
Annual tax
$2,483
Flood zone
X · Low risk
Lot
109,466 sqft
Type
Single Family Residence

At a glance

Single family
Built 1999
2 car garage
2.51 acres
Lot size
1,914 sqft
Living area

Payment

Est. monthly payment
$3,321/mo
Down payment (20%)
$109,000
Property taxes
$207/mo
Rate assumed
6.8% · 30 yr
View full breakdown

Details

Type
Single Family Residence
Year Built
1999
Lot
109,466 sqft
Cooling
Central Air
Heating
Central
Parking
-
Days on Market
188
Ceiling Fans(s)
Rain Gutters
Dryer
Microwave
Range
Refrigerator
Washer
Elementary
East Lake Elem
Middle
Neptune Middle (6-8)
High
Tohopekaliga High School

Districts can re-zone, so verify directly with the district before relying on these.

Homestead exemption on file Flood Zone X
Annual Tax (2025)
$2,483
Parcel #
17-25-30-2921-0001-0010

Taxes reflect the most recent assessment in the MLS feed. Actual tax owed can vary, so confirm with the county property appraiser before closing.

Subdivision
D S Estates
County
Osceola
MLS Area
34744 - Kissimmee
Lot Size
109,466 sqft

Price history

Date
Event
Price
6/13/2026
Price change
Source: Stellar MLS #S5147254
$545,000-0.7%
$285/sqft
4/5/2026
Listed for sale
Source: Stellar MLS #S5147254
$549,000
$287/sqft

Neighborhood

2507 Winners Cir
Kissimmee, FL, 34744 · 34744 - Kissimmee

Market insights

Offer Insights

Choose an offer strength

List price: $545,000
$540,000 – $545,000
99.5% – 100% of listTops out right at the list price
80% of listList price
218 of the last 340 home closings in 34744 landed at this number or higher (64%). The median one sat 36 days before it went under contract, and this one is on day 188 after a $4,000 cut.

Sample: 340 closed home sales in 34744 over the last 8 months, Stellar MLS. A starting point, not a guarantee.

Talk through an offer with our team

Calculator

Est. monthly payment
$3,322/mo
Principal & interest$2,842
Property taxes$207
Insurance$273
Down payment20% · $109,000
Interest rate6.80%
Loan term

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Property taxes are this home's actual annual bill from the MLS, divided by twelve. Insurance estimated at 0.60%. Rate defaults to 6.8% on a 30-year fixed. Tap a pencil to use your own numbers. Estimates only, not a loan quote.

Quick answers.

Price

$545,000

$285 per sq ft

Beds and baths

3 beds, 2 baths

Size

1,914 sq ft

Time on market

188 days

Year built

1999

Monthly payment

About $3,321/mo

That is 20% down on a 30-year fixed at 6.8%, plus the home's $2,483 annual tax bill, insurance.

Flood zone

Zone X

That is outside the high-risk areas, so flood insurance is usually optional rather than required by a lender.

Offer

What should I offer?

Have another question?

Brokered byKELLER WILLIAMS REALTY AT THE LAKESListing agent: Ashley HellesvigListing data from Stellar MLS, MLS# S5147254.

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