Don’t miss out on a great opportunity to own a SINGLE-STORY, LOW HOA townhouse in Winter Park’s popular Windward Square community. Imagine yourself enjoying any of its three pools, tennis courts, BBQ area, or outdoor reading benches AND being located a mere 5 minutes from grocery shopping and dining esablishments. More shopping, dining, and opportunities to just relax and watch busy shoppers are available nearby, in Winter Park’s downtown Park Avenue district. This two-bedroom, no carpet unit offers a living/dining room combo with beautiful morning light. In addition to its smartly situated full bathroom, a separate sink and dressing area is available in the master bedroom, for owner convenience. Walk-in closets are found in both bedrooms, and the townhouse has a designated laundry closet, too (washer and dryer convey). Sliding patio doors open to a fully-fenced backyard, affording privacy and the ability to garden, BBQ, or watch Fido play. An exterior storage closet provides space for yard or hobby items you own. You will love the 3-car parking pad right in front of your unit. No more searching for visitor parking spots! Just around the corner you’ll find the clubhouse and all the community amenities that give Windward Square its “easy living” reputation. Schedule your private showing today! ROOF: 2023 HVAC: 2023
Sold for $235,000
$235,000
2529 Leeward Way, Winter Park, FL 32792
2beds
912sqft
Townhouse
Built in 1977
2,359 Square Feet Lot
$228,300 Zestimate®
$258/sqft
$1,698 Estimated rent
Home value
$228,300
$205,000 - $253,000
$1,698/mo
Zestimate® history
Owner options
List your home for rent
$1,698/mo
Rent Zestimate®
Find your next renter with Zillow Rental Manager. Plus, with online applications, you can quickly screen prospective tenants – for free.
$1,698/mo
Rent Zestimate®
Refinance and save
$1,761/mo
Est. payment
Refinancing to a lower rate could help reduce your monthly payments and save thousands over the life of the loan.
$1,761/mo
Est. payment
Explore your selling options
Work with a Zillow partner agent
Leverage their expertise and Zillow's premium Showcase listings to get your home seen by more buyers.
Get startedList with your own agent
Get your home in front of millions of buyers by listing it on Zillow.
Learn how to do itSell it yourself
Take full control of how buyers see your home on Zillow by listing For Sale by Owner (FSBO).
List your homeWhat's special
Three poolsTennis courtsBeautiful morning lightBbq areaDesignated laundry closetSliding patio doorsFully-fenced backyard
Zillow last checked:
Listing updated:
Listed by:
Chris Creegan 407-622-1111,
CREEGAN GROUP 407-622-1111,
Melinda Stewart 407-579-8781,
CREEGAN GROUP
Bought with:
Mike Yebba, III, 3388886
KELLER WILLIAMS WINTER PARK
Source: Stellar MLS,MLS#: O6288240
Originating MLS: Orlando Regional
Originating MLS: Orlando Regional
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 2
- Bathrooms: 1
- Full bathrooms: 1
Primary bedroom
- Features: Walk-In Closet(s)
- Level: First
- Area: 152.08 Square Feet
- Dimensions: 13.11x11.6
Bedroom 2
- Features: Walk-In Closet(s)
- Level: First
- Area: 119.9 Square Feet
- Dimensions: 11x10.9
Bathroom 1
- Features: Makeup/Vanity Space, Tub With Shower
- Level: First
- Area: 43.5 Square Feet
- Dimensions: 5x8.7
Kitchen
- Level: First
- Area: 68.87 Square Feet
- Dimensions: 9.7x7.1
Living room
- Level: First
- Area: 236.8 Square Feet
- Dimensions: 14.8x16
Heating
- Electric
Cooling
- Central Air
Appliances
- Included: Dishwasher, Disposal, Dryer, Electric Water Heater, Range, Refrigerator, Washer
- Laundry: Laundry Closet
Features
- Living Room/Dining Room Combo, Walk-In Closet(s)
- Flooring: Laminate, Tile
- Doors: Sliding Doors
- Has fireplace: No
Interior area
- Total structure area: 882
- Total interior livable area: 912 sqft
Property
Features
- Levels: One
- Stories: 1
- Exterior features: Courtyard, Private Mailbox, Rain Gutters, Sidewalk, Storage, Tennis Court(s)
Lot
- Size: 2,359 Square Feet
Details
- Parcel number: 34213052100001170
- Zoning: RMF-13
- Special conditions: None
Construction
Type & style
- Home type: Townhouse
- Property subtype: Townhouse
Materials
- Block, Concrete, Stucco
- Foundation: Slab
- Roof: Shingle
Condition
- New construction: No
- Year built: 1977
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Fire Hydrant, Public, Street Lights
Community & HOA
Community
- Features: Clubhouse, Deed Restrictions, Park, Playground, Pool, Sidewalks, Tennis Court(s)
- Pet fee: $0 monthly
- Subdivision: WINDWARD SQUARE SEC 2
HOA
- Has HOA: Yes
- Services included: Common Area Taxes, Community Pool, Maintenance Grounds, Pool Maintenance, Recreational Facilities
- HOA fee: $95 monthly
- HOA name: Sharee Scott
- HOA phone: 407-647-2622
Location
- Region: Winter Park
Financial & listing details
- Price per square foot: $258/sqft
- Tax assessed value: $199,874
- Annual tax amount: $262
- Date on market: 3/13/2025
- Cumulative days on market: 12 days
- Listing terms: Cash,Conventional,FHA,VA Loan
- Ownership: Fee Simple
- Total actual rent: 0
- Electric utility on property: Yes
- Road surface type: Asphalt
Price history
| Date | Event | Price |
|---|---|---|
| 4/29/2025 | Sold | $235,000$258/sqft |
Source:  Stellar MLS #O6288240 Report a problem | ||
| 4/8/2025 | Pending sale | $235,000$258/sqft |
Source: Stellar MLS #O6288240 Report a problem | ||
| 4/3/2025 | Listed for sale | $235,000$258/sqft |
Source: Stellar MLS #O6288240 Report a problem | ||
| 3/22/2025 | Pending sale | $235,000$258/sqft |
Source: Stellar MLS #O6288240 Report a problem | ||
| 3/13/2025 | Listed for sale | $235,000+62.1%$258/sqft |
Source: Stellar MLS #O6288240 Report a problem | ||
| 1/9/2007 | Sold | $145,000$159/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $298 +13.7% | $50,161 +2.9% |
| 2024 | $262 +5.5% | $48,747 +3% |
| 2023 | $248 +6.7% | $47,327 +3% |
| 2022 | $233 -7.5% | $45,949 +3% |
| 2021 | $252 +3.4% | $44,611 +1.4% |
| 2020 | $243 +3.1% | $43,995 +2.3% |
| 2019 | $236 | $43,006 +1.9% |
| 2018 | $236 +2.8% | $42,204 +2.1% |
| 2017 | $230 +2.5% | $41,336 +1.4% |
| 2016 | $224 +0.9% | $40,769 +1.4% |
| 2015 | $222 | $40,205 +0.8% |
| 2014 | $222 +27% | $39,886 +1.5% |
| 2013 | $175 -9.7% | $39,297 -5% |
| 2012 | $194 -36.8% | $41,354 -16.3% |
| 2011 | $307 -18.2% | $49,411 -13.6% |
| 2010 | $375 -37.4% | $57,182 -29.8% |
| 2009 | $599 -34.8% | $81,508 -23.1% |
| 2008 | $918 -52.3% | $105,957 -2.9% |
| 2007 | $1,927 +308.5% | $109,129 +113.2% |
| 2006 | $472 +4.6% | $51,189 +3% |
| 2005 | $451 +3.5% | $49,698 +3% |
| 2004 | $436 +2.8% | $48,250 +1.9% |
| 2003 | $424 +3.8% | $47,350 +2.4% |
| 2002 | $408 +10.7% | $46,240 +4.6% |
| 2000 | $369 | $44,186 |
Find assessor info on the county website
Neighborhood: 32792
Nearby homes
- $261,3002 bd2 ba1k sqft2527 Leeward Way, Winter Park, FL 32792Off Market
- $258,6003 bd2 ba1.2k sqft2531 Leeward Way, Winter Park, FL 32792Off Market
- $275,0003 bd2 ba1.4k sqft2533 Leeward Way, Winter Park, FL 32792Sold
- $281,7003 bd2 ba1.4k sqft2525 Leeward Way, Winter Park, FL 32792Off Market
- $265,1002 bd1 ba1.1k sqft2628 Exuma Way, Winter Park, FL 32792Off Market
- $218,8002 bd1 ba854 sqft2630 Exuma Way, Winter Park, FL 32792Off Market
- $291,4003 bd2 ba1.7k sqft2535 Leeward Way, Winter Park, FL 32792Off Market
- $266,0002 bd2 ba1k sqft2523 Leeward Way, Winter Park, FL 32792Off Market
Nearby schools
GreatSchools rating
- 7/10Eastbrook Elementary SchoolGrades: PK-5Distance: 1 mi
- 8/10Tuskawilla Middle SchoolGrades: 6-8Distance: 2.9 mi
- 7/10Lake Howell High SchoolGrades: 9-12Distance: 2.5 mi
Schools provided by the listing agent
- Elementary: Eastbrook Elementary
- Middle: Tuskawilla Middle
- High: Lake Howell High
Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$228,300
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$228,300
- Florida
- Seminole County
- Winter Park
- 32792
- 2529 Leeward Way
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Winter Park Topics
