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$180,000

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 1,290 Sq. Ft.
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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.

Full Property Details for 1329 Windsor Dr

General

  • Price: $180,000
  • HOA FEE: $375/month
  • Taxes: $992 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6403991
  • Updated: 5/2/2026
  • Added to Site: 16 day(s) ago

Rental Information

  • Min. Lease: 1-2 Years

Interior

  • Number of Rooms: 6
  • Interior Features: Ceiling Fan(s), Kitchen and Family Room Combination, Open Floorplan, PrimaryBedroom Upstairs, Solid Surface Counters, Thermostat, Walk-In Closet(s)
  • Appliances: Electric Water Heater, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Inside

Additional Information

  • Shared Amenities: Park, Playground, Pool, Recreation Facilities
  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Balcony, Lighting, Rain Gutters, Sidewalk, Sliding Doors
  • Deck/Patio: Covered, Rear Porch
  • Porch/Patio/Deck: Covered, Rear Porch

Parking

  • Parking Features: Assigned, Ground Level, Guest, Open

Location

  • Area: 34741 - Kissimmee (Downtown East)
  • County: Osceola
  • Development Name: 34741 - Kissimmee (Downtown East)
  • Subdivision: WINDSOR PINES 1 CONDO
  • Driving Directions: From 192, North on John Young to Left into Windsor Pines (before Carroll), Right on Surrey.
  • Direction Faces: South

School Information

  • Elementary School: Highlands Elem
  • Middle School: Kissimmee Middle
  • High School: Osceola High School

Community

  • Community Name: 34741 - Kissimmee (Downtown East)
  • Community Features: Association Recreation - Owned, Buyer Approval Required, Community Mailbox, Deed Restrictions, Park, Playground, Pool, Sidewalks
  • Optional Amenities: Park, Playground, Pool, Recreation Facilities
  • Association: Yes
  • Assoc. Name: Association Management Group of CFL/Melanie Ault
  • Assoc. Fees Include: Common Area Taxes, Community Pool, Maintenance Structure, Maintenance Grounds, Manager, Pool Maintenance, Recreational Facilities, Trash, Water
  • Pet Restrictions: Buyer and or Buyers Agent to verify with County, City, HOA and or Condo Association., / 50lbs.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Electricity Connected, Public, Sewer Connected, Street Lights, Water Connected

Structural Information

  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 1,290
  • Sq. Ft. Source: Public Records
  • Year Built: 1982

Lot Features

  • Lot Size (Acres): 0.02
  • Lot Size (Sq. Ft.): 806
  • Lot Size: 806
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Financial Considerations

  • Association Fee: $375
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $992
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Condominium
  • Special Conditions: None
  • Legal Description: WINDSOR PINES 1 CB 1 PG 56 UNIT 18
  • Flood Zone Info: X
  • APN: 92529237100010180
  • Property ID: 92529237100010180
  • Block/Lot/Section: 1

Listed by Serhant

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— 1329 Windsor Dr —

  • Serhant

  • Serhant

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with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 1329 Windsor Dr

School District:Osceola County School District
NameGradesDistance
Highlands Elementary School, Kissimmee, FL
800 West Donegan Avenue, Kissimmee, FL 34741
PK-50.5 mi
Kissimmee Middle School
2410 Dyer Boulevard, Kissimmee, FL 34741
6-81.3 mi
Osceola High School
420 South Thacker Avenue, Kissimmee, FL 34741
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1329 Windsor Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$180,000
50%
MLS
6/15/2018
Sold
$120,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1329 Windsor Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$747
—
$87,825
3%
2024
$747
5%
$85,350
3%
2023
$713
9%
$82,865
6%
2021
$652
-3%
$78,109
-3%
2022
$672
3%
$80,452
4%
2021
$652
5%
$77,031
2%
2019
$620
-12%
$75,300
98%
2018
$704
3%
$38,000
3%
2017
$683
9%
$36,800
11%
2016
$626
9%
$33,300
12%
2015
$576
7%
$29,600
7%
2014
$540
1%
$27,600
2%
2013
$533
—
$27,000
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1329 Windsor Drive, Kissimmee, FL 34741 (MLS# O6403991) is a Condo property with 2 bedrooms, 2 full bathrooms and 1 partial bathroom. 1329 Windsor Drive is currently listed for $180,000 and was received on May 01, 2026. Want to learn more about 1329 Windsor Drive? Do you have questions about finding other Condo real estate for sale in Kissimmee? You can browse all Kissimmee real estate or contact a Coldwell Banker agent to request more information.

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