1329 Windsor Dr

Off Market

1329 Windsor Dr

Kissimmee FL 34741

1560 sq. ft.

806 sq. ft.

Condo

Last sold for $118,000

Shawn Layton, last sold this property on 09 October 2026 after 160 days on market.

Overview

Two stories, two bedrooms, two and a half baths, with the boring expensive stuff already handled. NEW roof overhead, NEW AC, NEW hot water heater, special assessment already paid, NEW living room flooring downstairs, NEW carpet up, and FRESH paint throughout. The first floor opens into a foyer that gives way to a full dining room on one side and a kitchen with breakfast bar seating on the other, both flanking a living room that stretches to back sliders. A second set of sliders off the front leads to a private patio, so you get cross-breeze and two outdoor spots before you even head upstairs. A half bath sits tucked off the kitchen for guests. Upstairs holds two true primary suites, each with its own full bathroom and its own private balcony. One faces the front, one faces the back, both have walk-in closets, and the laundry closet lives upstairs where the laundry actually is. Windsor Pines comes with a community pool and a playground, and the location does the rest of the work. You're a few minutes from The Loop, where the grocery run, the dinner reservation, and the movie all happen in one parking lot. Ten minutes to downtown Kissimmee and the lakefront, straight onto Osceola Parkway or the Turnpike when you need to be elsewhere, and about fifteen minutes from the Disney gates when you don't. Two primaries. Two porches. Two private balconies. One opportunity.

Features

2 bedrooms

3 bathrooms

1560 sq. ft. floor area

806 sq. ft. lot size

Condo

Estimated Value

Based on this property and similar 2 bedroom condos sold in Kissimmee over the last 12 months, the estimated median property value of 1329 Windsor Dr is $167k.

Median value

$167k

Estimated value range

$110k - $230k

Median days on market

Estimated value trend

-7%

decrease over the last 12 months

Average days on market is based on recent, comparable sales in Kissimmee. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 1329 Windsor Dr

2026

Sold

$118,000

09 Oct 2026 by Shawn Layton, of SERHANT

2018

Sold

$120,000

15 Jun 2018 by Matt Davies

Happy sellers in Kissimmee

90%

90% of sellers in Kissimmee reported that their sale price either exceeded or met their price expectations.

Kissimmee stands out for consistently delivering exceptional satisfaction and strong market results for homeowners.

This is based on voluntary sentiment collected from 4 reviews in Kissimmee over the last 12 months.

Local market activity for 2 bedroom condos in Kissimmee

In the last 12 months, 33 two-bedroom condos similar to 1329 Windsor Dr, have been sold.

This represents a 22% increase in two-bedroom condos sales when compared to the previous 12 months.

Sold

For Sale

Interested in selling?

People are reaching out to these agents in Kissimmee for a market analysis.

Joaydha Santos

at THE RENTAL & SALES GALLERY LLC

(18 reviews)

Get a market analysis

Ninibeth Perez Fernandez

at Realty ONE Group Estates | Sunrise

(17 reviews)

Get a market analysis

Amelia Hunter

at LPT Realty Lake Mary

(44 reviews)

Get a market analysis

Keith Miles, Jr

at PROPERTIES IN TOWN

(27 reviews)

Get a market analysis

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in Kissimmee

Joaydha Santos

Joaydha Santos is a recommended agent for Kissimmee. They have 1 local sale and collected 5 local reviews across the last 12 months.

5 (18 reviews)
5 Reviews in Kissimmee
1 Sale in Kissimmee

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Ninibeth Perez Fernandez

Ninibeth Perez Fernandez is a recommended agent for Kissimmee. They have 3 local sales and collected 4 local reviews across the last 12 months.

5 (17 reviews)
4 Reviews in Kissimmee
3 Sales in Kissimmee

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Amelia Hunter

Sellers who recommend Amelia Hunter have praised them for being local expert, reliable, responsive, empathetic, clear communication, dedicated, and honest