MLS data updated Oct 14, 2026
Windward SquareReal Estate Market Report · October 2026
Windward Square real estate market report · Winter Park, FL
Winter Park, FL
Windward Square is a residential community in Winter Park, Florida. This live report tracks active and pending listings, 12-month sale prices and days on market, and public-record sales for the surrounding ZIP.
Median sold: $272K · Median days on market: 13 · Sold-to-list: 97.8% · Source: Stellar MLS, last 12 mo
About 2.8 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
Aggregate statistics from Stellar MLS closed sales over the last 12 months and live MLS inventory. A market read, not an appraisal of any home or a listing of individual sales.
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Windward Square · 4th Quarter 2026
13 sales · Stellar MLS · last 12 mo
$272K
Median Sale Price
13 days
Median Days on Market
97.8%
Sold-to-List
$244
Median $/sqft
Recent Sales Map
44 recent individual sales in and around Windward Square · FL public records · no addresses published
Approximate sale locations — dots are offset ±1 home for privacy
| Beds | Baths | Sq Ft | Listed | Sold ▼ | List Price | Sold Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|---|---|---|
| — | — | 3,858 | — | 12/1/25 | — | $935,000 | $242 | — |
| — | — | 2,059 | — | 12/1/25 | — | $770,000 | $374 | — |
| — | — | 1,419 | — | 12/1/25 | — | $675,000 | $476 | — |
| — | — | 2,256 | — | 12/1/25 | — | $605,000 | $268 | — |
| — | — | 1,370 | — | 12/1/25 | — | $530,000 | $387 | — |
| — | — | 2,225 | — | 12/1/25 | — | $479,000 | $215 | — |
| — | — | 1,125 | — | 12/1/25 | — | $470,000 | $418 | — |
| — | — | 1,738 | — | 12/1/25 | — | $455,000 | $262 | — |
| — | — | 1,364 | — | 12/1/25 | — | $450,000 | $330 | — |
| — | — | 1,829 | — | 12/1/25 | — | $450,000 | $246 | — |
| — | — | 1,677 | — | 12/1/25 | — | $450,000 | $268 | — |
| — | — | 1,785 | — | 12/1/25 | — | $440,000 | $246 | — |
| — | — | 1,578 | — | 12/1/25 | — | $420,000 | $266 | — |
| — | — | 1,050 | — | 12/1/25 | — | $418,000 | $398 | — |
| — | — | 1,382 | — | 12/1/25 | — | $415,000 | $300 | — |
| — | — | 1,200 | — | 12/1/25 | — | $395,000 | $329 | — |
| — | — | 1,200 | — | 12/1/25 | — | $375,000 | $313 | — |
| — | — | 1,530 | — | 12/1/25 | — | $365,000 | $239 | — |
| — | — | 1,214 | — | 12/1/25 | — | $350,000 | $288 | — |
| — | — | 1,821 | — | 12/1/25 | — | $343,000 | $188 | — |
| — | — | 1,676 | — | 12/1/25 | — | $340,000 | $203 | — |
| — | — | 1,221 | — | 12/1/25 | — | $315,000 | $258 | — |
| — | — | 1,415 | — | 12/1/25 | — | $245,000 | $173 | — |
| — | — | 1,281 | — | 12/1/25 | — | $205,000 | $160 | — |
| — | — | 1,219 | — | 12/1/25 | — | $205,000 | $168 | — |
| — | — | 987 | — | 12/1/25 | — | $200,000 | $203 | — |
| — | — | 1,151 | — | 12/1/25 | — | $199,000 | $173 | — |
| — | — | 1,120 | — | 12/1/25 | — | $195,000 | $174 | — |
| — | — | 4,560 | — | 11/1/25 | — | $1,500,000 | $329 | — |
| — | — | 2,455 | — | 11/1/25 | — | $899,000 | $366 | — |
| — | — | 2,498 | — | 11/1/25 | — | $764,000 | $306 | — |
| — | — | 2,111 | — | 11/1/25 | — | $750,000 | $355 | — |
| — | — | 1,829 | — | 11/1/25 | — | $699,500 | $382 | — |
| — | — | 2,256 | — | 11/1/25 | — | $660,000 | $293 | — |
| — | — | 1,772 | — | 11/1/25 | — | $545,000 | $308 | — |
| — | — | 2,124 | — | 11/1/25 | — | $528,000 | $249 | — |
| — | — | 1,277 | — | 11/1/25 | — | $500,000 | $392 | — |
| — | — | 2,427 | — | 11/1/25 | — | $469,500 | $193 | — |
| — | — | 1,978 | — | 11/1/25 | — | $460,000 | $233 | — |
| — | — | 1,929 | — | 11/1/25 | — | $350,000 | $181 | — |
| — | — | 1,320 | — | 11/1/25 | — | $330,000 | $250 | — |
| — | — | 1,004 | — | 11/1/25 | — | $290,000 | $289 | — |
| — | — | 1,018 | — | 11/1/25 | — | $180,000 | $177 | — |
| — | — | 1,393 | — | 11/1/25 | — | $177,000 | $127 | — |
Currently For Sale
3 active listings in Windward Square
$178/sqft
View details
$204/sqft
View details
$150/sqft
View details
| Beds | Baths | Sq Ft | List Price | $/Sq Ft | DOM |
|---|---|---|---|---|---|
| 2 | 2 | 1,544 | $275,000 | $178 | 33 |
| 3 | 2 | 1,467 | $299,990 | $204 | 37 |
| 3 | 3 | 1,803 | $270,000 | $150 | 91 |
Windward Square Market — Common Questions
Is Windward Square a buyer's or seller's market in 2026?+
Windward Square is currently a seller's market with about 2.8 months of inventory. About 2.8 months of inventory — homes are selling faster than new ones come on the market, so sellers hold the leverage (under 4 months = seller's market).
What is the median home sale price in Windward Square?+
Based on Stellar MLS closed sales over the last 12 months, the median sale price in Windward Square is approximately $272K.
How many homes are for sale in Windward Square?+
There are currently 3 active listings in Windward Square, with homes selling at roughly 1.1 per month. That works out to about 2.8 months of inventory.
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Ryan Solberg
MaxLife Realty
321.373.3536
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What clients say
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More communities in Winter Park
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- Comstock Park13 sales in 12 mo
- Country Lane13 sales in 12 mo
- Garden Lake Estates13 sales in 12 mo
- Virginia Heights, Winter Park12 sales in 12 mo
- Charmont11 sales in 12 mo
- Winter Park Estates11 sales in 12 mo
- Casa Aloma10 sales in 12 mo
- Enclave at Hawks Crest10 sales in 12 mo
- Lost Creek10 sales in 12 mo
- Wrenwood Heights10 sales in 12 mo
- Lakeside Manor Apartments9 sales in 12 mo
Report generated October 14, 2026 at 8:38 PM ET · Powered by Stellar MLS
MLS Data:Active and pending listing data is sourced from the Stellar MLS as distributed by 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. The MLS GRID does not guarantee the accuracy of this data, which may not reflect all real estate activity in the area.
Sold Data: Sales analysis is derived from Florida Department of Revenue public property records (arm's-length transactions). Ryan Solberg and MaxLife Realty LLC are not affiliated with Windward Squareor its HOA. This report is not intended to solicit properties already listed for sale nor to cause a breach of an existing agency relationship. Data should be independently verified. E&OE.
Based on information submitted to the MLS GRID as of October 14, 2026 at 12:39 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.
Moving to Windward Square
Utilities & Services
Windward Square is in Orange County, Florida. Here's who to call to get power, water, and trash service set up in your name before closing.
Electric
Orlando Utilities Commission (OUC) · (407) 423-9018City of Orlando and parts of unincorporated Orange County. OUC also provides water in its territory.
Duke Energy Florida · (800) 700-8744Most of unincorporated Orange County, plus Winter Garden, Apopka, and Ocoee.
Water & Sewer
Orange County Utilities · (407) 836-5515Unincorporated Orange County (water & sewer).
OUC — Water (City of Orlando) · (407) 423-9018City of Orlando — OUC provides both water and electric.
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 October 14, 2026 at 12:39 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.
All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.
Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA