Date
Details
Price
Change
Source
5/28/2026
Listed
$299,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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1/20
$299,000 Just Listed
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Property Description
Welcome Home in the heart of Winter Park! Fantastic single-level townhouse fully remodeled with 3 bedrooms and 2 bathrooms, featuring beautiful cathedral ceilings upon entry and modern upgrades throughout. This move-in ready property offers a brand-new 2026 roof, freshly painted interior and exterior, a beautifully renovated kitchen, and fully updated bathrooms with elegant quartz countertops. Featuring a newer A/C system and new water heater, this home provides extra peace of mind for the new owners. Situated on a spacious corner lot, this home is perfect for families seeking comfort, style, and convenience. Enjoy your own private fenced backyard, ideal for relaxing, entertaining, or pets. The community offers a low HOA with fantastic amenities including a swimming pool, tennis courts, and playground. Conveniently located just 8 miles from UCF with quick access to shopping, dining, entertainment, and major highways. A perfect blend of location, lifestyle, and value!
Full Property Details
Full Property Details for 2529 Windward Way
General
- Price: $299,000
- HOA FEE: $99/month
- Taxes: $332 (2025)
- Status: Active
- Type: Townhouse
- Source: MidFloridaRegionalMLS
- MLS ID: S5150790
- Updated: 5/29/2026
- Added to Site: 1 day(s) ago
Rental Information
- Min. Lease: 7 Months
Interior
- Number of Rooms: 7
- Interior Features: Cathedral Ceiling(s), Thermostat
- Appliances: Dishwasher, Microwave, Range, Refrigerator
- Furnishings: Unfurnished
- Flooring: Vinyl
Rooms
Bathrooms
- Total Bathrooms: 2
- Full Bathrooms: 2
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Closet
Exterior
- Exterior Features: Private Mailbox, Sliding Doors
Parking
- Parking Features: Assigned, Driveway, Parking Pad
Location
- Area: 32792 - Winter Park/Aloma
- County: Seminole
- Development Name: 32792 - Winter Park/Aloma
- Subdivision: WINDWARD SQUARE SEC 1
- Driving Directions: From 436, right Howell Branch, right on Antilles Dr, right on Windward Way, located on the right.
- Direction Faces: South
Community
- Community Name: 32792 - Winter Park/Aloma
- Community Features: Clubhouse, Playground, Pool, Tennis Court(s)
- Association: Yes
- Assoc. Name: Specialty Management Company
- Assoc. Fees Include: Community Pool, Maintenance Structure, Pool Maintenance
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central
Utilities
- Sewer: Public Sewer
- Water: Public
- Utility Description: Public
Structural Information
- Exterior Const.: Block, Stucco
- Roof: Membrane
- 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.): 3,760
- Lot Size: 3760
- Street/Road Desc.: Concrete
Financial Considerations
- Association Fee: $99
- Assoc Fee Freq.: Monthly
- Assoc Fee Desc.: Required
- Tax Amount: $332.45
- 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 My Q Realty, Llc
We Value Your Privacy
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Listing agent
— 2529 Windward Way —
My Q Realty, Llc
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 2529 Windward Way
School District:Seminole County School District
| Name | Grades | Distance |
|---|---|---|
Eastbrook Elementary School 5525 Tangerine Avenue, Winter Park, FL 32792 | K-5 | 1 mi |
Tuskawilla Middle School 1801 Tuskawilla Road, Oviedo, FL 32765 | 6-8 | 2.9 mi |
Lake Howell High School 4200 Dike Road, Winter Park, FL 32792 | 9-12 | 2.4 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 2529 Windward Way
Tax History
Tax History for 2529 Windward Way
Year
Property Taxes
Change
Tax Assessment
Change
2025
$332
9%
$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
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 2529 Windward Way
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2529 Windward Way, Winter Park, FL 32792 (MLS# S5150790) is a Townhouse property with 3 bedrooms and 2 full bathrooms. 2529 Windward Way is currently listed for $299,000 and was received on May 28, 2026. Want to learn more about 2529 Windward Way? Do you have questions about finding other Townhouse 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.