2529 Windward Way, FL
Stellar MLS

$299,000

2529 Windward Way

Winter Park, FL 32792

Pending
3
Beds
2
Baths
1,105
Sq Ft
0.09
Acres
1977
Built
$271/sqft360° tour
Townhouse

Property type

1977

Year built

3,760 sqft

Lot size

$271

Price / sq ft

$99/mo

HOA dues

5

Days on market

X

Flood zone

About this home

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!

Estimated monthly payment

Principal & interest$1,512
Property taxes$28
Home insurance (est.)$137
HOA dues$99

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history5 days on market

  1. Status: Pending
    Jun 2, 2026
  2. Listed$299,000
    May 28, 2026
  3. Price increased$299,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Townhouse
Status
Pending
Days on market
5
Subdivision
Windward Square Sec 1
County
Seminole
Year built
1977
Living area
1,105 sq ft
Price/sq ft
$271
Building area
1,171 sq ft (Public Records)
Lot size
3,760 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12117C0260F)
Annual taxes
$332 (2025)
Parcel #
34-21-30-519-0000-0060
Zoning
RMF-13
MLS #
S5150790

Interior Details

Bedrooms
3
Full bathrooms
2
Flooring
Vinyl
Appliances
Dishwasher, Microwave, Range, Refrigerator
Interior features
Cathedral Ceiling(s), Thermostat
Laundry
Laundry Closet
Stories / Levels
One
Direction faces
South

Heating & Cooling

Heating
Central
Cooling
Central Air

Parking

Attached garage
No
Parking features
Assigned, Driveway, Parking Pad

HOA & Financial

HOA fee
$99 / Monthly
Monthly HOA
$99/mo
Total monthly fees
$99/mo
Total annual fees
$1,188
HOA name
Specialty Management Company
CDD
No
Homestead exemption
Yes
Min lease term
7 Months
Listing terms
Cash, Conventional, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
Buyer and Buyer’s Agent are responsible for independently verifying all lease/rental restrictions, requirements, and approvals directly with the HOA/County.
Approval process
Buyer and Buyer’s Agent are responsible for independently verifying all lease/rental restrictions, requirements, and approvals directly with the HOA/County.

Exterior & Construction

Exterior features
Private Mailbox, Sliding Doors
Construction materials
Block, Stucco
Roof
Membrane
Foundation
Slab
Road surface
Concrete

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
Public

Community

Pets allowed
No

Room Details

RoomLevelDimensions
Primary BedroomFirst
Bedroom 2First
Bedroom 3First
KitchenFirst
Primary BathroomFirst
Bathroom 2First
Great RoomFirst

Listing Details

Listing date
2026-05-28
On market date
2026-05-28
Original list price
$299,000
Occupant type
Vacant
MLS area
32792 - Winter Park/Aloma
Listing AOR
Osceola
Status changed
2026-06-02
Tax legal description
LOT 6 WINDWARD SQUARE SEC 1 PB 19 PG 86

Flood risk

Minimal riskFEMA Zone XPanel 12117C0260F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From 436, right Howell Branch,right on Antilles Dr, right on Windward Way, located on the right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of June 2, 2026 at 2:09 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA