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$209,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 2 Beds
  • 2 Full Baths
  • 1,105 Sq. Ft.
  • Updated 16 hours ago
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Bring your creativity and imagination to this 2-bedroom, 2-bath fixer-upper with 1,105 sq ft in a desirable Winter Park 32792 location. It offers a private walled backyard and a low HOA. The functional split-bedroom layout provides privacy, while the open living and dining areas create a comfortable space for everyday living or entertaining. The kitchen offers ample cabinetry and counter space, community swimming pool and tennis court. Only 3 mi to Full Sail University, 5 mi to UCF, 4 mi to AdventHealth Winter Park, and 6 mi to Park Avenue and Downtown Winter Park. Nearby shopping, dining, and grocery options are within minutes, with quick connectivity to SR-436, University Blvd, and SR-417 for commuting throughout Central Florida. An excellent opportunity to own in Winter Park with space, privacy, and strong location. This home is loaded with potential. Make it your own or have a great investment property.

Full Property Details for 2529 Windward Way

General

  • Price: $209,000
  • HOA FEE: $95/month
  • Taxes: $341 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6388076
  • Updated: 3/9/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 6
  • Interior Features: Living Room/Dining Room Combo, Vaulted Ceiling(s)
  • Appliances: Dishwasher, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Concrete, Laminate

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Inside, Laundry Closet

Additional Information

  • Shared Amenities: Pool

Exterior

  • Exterior Features: Private Yard

Parking

  • Parking Features: Curb Parking

Location

  • Area: 32792 - Winter Park/Aloma
  • County: Seminole
  • Development Name: 32792 - Winter Park/Aloma
  • Subdivision: WINDWARD SQUARE SEC 1
  • Driving Directions: From 436 go East on Howell Branch to the second entrance into Windward Sq
  • Direction Faces: South

School Information

  • Elementary School: Eastbrook Elementary
  • Middle School: Tuskawilla Middle
  • High School: Lake Howell High

Community

  • Community Name: 32792 - Winter Park/Aloma
  • Optional Amenities: Pool
  • Association: Yes
  • Assoc. Name: Nicolas Pacheco

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water: None
  • Utility Description: Cable Connected, Electricity Connected, Sewer Connected, Water Connected

Structural Information

  • Architectural Info: Contemporary, Patio
  • Architectural Style: Contemporary, Patio
  • Exterior Const.: Block, Stucco, Wood Siding
  • Roof: Built-Up
  • Common Walls: End Unit
  • Stories/Levels: One
  • Square Feet: 1,105
  • Sq. Ft. Source: Public Records
  • Year Built: 1977

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 370
  • Lot Size: 370
  • Lot Dimensions: 38 x 100 x 37 x 100
  • Street/Road Desc.: Asphalt
  • Fencing (Description): Masonry

Financial Considerations

  • Association Fee: $95
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $341
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: LOT 6 WINDWARD SQUARE SEC 1 PB 19 PG 86
  • Flood Zone Info: X
  • APN: 34213051900000060
  • Property ID: 34213051900000060

Listed by Fannie Hillman & Associates

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Listing agent

— 2529 Windward Way —

  • Fannie Hillman & Associates

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2529 Windward Way

School District:Seminole County School District
NameGradesDistance
Eastbrook Elementary School
5525 Tangerine Avenue, Winter Park, FL 32792
K-51 mi
Tuskawilla Middle School
1801 Tuskawilla Road, Oviedo, FL 32765
6-82.9 mi
Lake Howell High School
4200 Dike Road, Winter Park, FL 32792
9-122.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2529 Windward Way Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/09/2026
Listed
$209,000
147.34%
MLS
3/11/2009
Sold
$84,500
—
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 2529 Windward Way

Year
Property Taxes
Change
Tax Assessment
Change
2025
$341
12%
$56,740
3%
2024
$304
2%
$55,141
3%
2023
$299
-6%
$53,535
6%
2021
$319
-2%
$50,462
-3%
2022
$324
2%
$51,976
4%
2021
$319
5%
$49,765
2%
2019
$305
2%
$48,646
2%
2018
$298
2%
$47,739
2%
2017
$293
—
$46,757
2%
2016
$293
-1%
$45,795
1%
2015
$295
6%
$45,477
1%
2014
$279
12%
$45,116
2%
2013
$248
—
$44,449
—
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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with our affiliated lender
NMLS#: 1598647

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Listed by Fannie Hillman & Associates

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2529 Windward Way, Winter Park, FL 32792 (MLS# O6388076) is a Single Family property with 2 bedrooms and 2 full bathrooms. 2529 Windward Way is currently listed for $209,000 and was received on March 09, 2026. Want to learn more about 2529 Windward Way? Do you have questions about finding other Single Family real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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