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Megan Dowdy Realty
Market report, updated
Winter Park Home Values and Market Report
Search in the city of Winter Park
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Market at a glance
Over the last 12 months, homes sold for 96.4% of list price in 62 days on average.
Average price, last 12 months
What sellers asked vs. what homes actually sold for, by closing month.
Homes sold per month
Closed sales, last 12 months.
Peak: 126 sales in Jun. Last month: 75.
Where the market stands
All homes in this report, by status.
Buyer's or seller's market?
Months it would take to sell every active home at the pace of the last 6 months.
Homes are selling quickly, which favors sellers in this market.
Average price by status
Average days on market
Browse homes by status
Choose a status to see its numbers, charts and listings.
Active homes
Currently for salePrice vs. living area
Each dot is one of the 250 newest homes. Hover a dot for its address, click it to see the home.
14 homes didn’t report living area and aren’t shown.
4 homes are larger or pricier than this chart’s scale and aren’t shown.
How long homes have been listed
Number of homes by days on market.
Bedroom mix
Number of homes by bedroom count.
35 homes didn’t report bedrooms and aren’t shown.
Highest price per ft²
Top 7 homes among the newest.
All active listings (370)
The map shows the 249 newest homes with a location. Click a marker for the home.
| Address | Beds | Baths | Living ft² | List price | $ / ft² | Days on market |
|---|---|---|---|---|---|---|
| 1667 Walnut AvenueWinter Park, FL 32789 | 4 | 4 | 3,535 | $2,275,000 | $643 | 1 day |
| 1250 S Denning Drive Unit 203Winter Park, FL 32789 | 2 | 2 | 908 | $260,000 | $286 | 1 day |
| 1008 N Pennsylvania AvenueWinter Park, FL 32789 | 4 | 5 | 3,530 | $2,500,000 | $708 | 1 day |
| 610 Penn PlaceWinter Park, FL 32789 | 4 | 4 | 3,174 | $1,895,000 | $597 | 1 day |
| 1351 Mayfield AvenueWinter Park, FL 32789 | 5 | 5 | 3,677 | $3,050,000 | $829 | 1 day |
| 2821 Riddle DriveWinter Park, FL 32789 | 4 | 4 | 2,445 | $299,900 | $122 | 2 days |
| 531 Worthington DriveWinter Park, FL 32789 | — | — | — | $1,100,000 | — | 2 days |
| 2531 Passamonte Drive Unit 4HWinter Park, FL 32792 | 3 | 3 | 1,790 | $369,000 | $206 | 2 days |
| 2821 Chantilly AvenueWinter Park, FL 32789 | 3 | 2 | 1,440 | $415,000 | $288 | 2 days |
| Address not availableWinter Park, FL 32789 | 4 | 5 | 2,830 | $2,100,000 | $742 | 3 days |
Under contract homes
Pending and contingent salesPrice vs. living area
Each dot is a home. Hover a dot for its address, click it to see the home.
5 homes didn’t report living area and aren’t shown.
Days on market before going under contract
Number of homes by days on market.
Bedroom mix
Number of homes by bedroom count.
6 homes didn’t report bedrooms and aren’t shown.
Highest price per ft²
Top 7 homes in this status.
All under contract listings
Every home in this list is on the map. Click a marker for the home.
| Address | Beds | Baths | Living ft² | List price | $ / ft² | Days on market |
|---|---|---|---|---|---|---|
| 662 Trinidad Court Unit 662Winter Park, FL 32792 | 1 | 1 | 759 | $177,000 | $233 | 2 days |
| 1124 N Pennsylvania AvenueWinter Park, FL 32789 | 3 | 3 | 2,254 | $1,650,000 | $732 | 0 days |
| 5415 N Lake Burkett LaneWinter Park, FL 32792 | 3 | 3 | 2,027 | $435,000 | $214 | 5 days |
| 2141 Lake DriveWinter Park, FL 32789 | 3 | 2 | 1,824 | $569,900 | $312 | 5 days |
| 3462 Seagrape DriveWinter Park, FL 32792 | 3 | 1 | 1,227 | $225,000 | $183 | 6 days |
| 200 St Andrews Boulevard Unit 906Winter Park, FL 32792 | 1 | 1 | 727 | $175,000 | $240 | 9 days |
| 257 Lincolnshire RoadWinter Park, FL 32792 | 3 | 2 | 1,610 | $550,000 | $341 | 9 days |
| 1900 Sunset DriveWinter Park, FL 32789 | 4 | 4 | 2,754 | $1,650,000 | $599 | 4 days |
| 541 Virginia DriveWinter Park, FL 32789 | 4 | 4 | 4,725 | $5,695,000 | $1,205 | 7 days |
| 2168 Ridge DriveWinter Park, FL 32792 | 3 | 2 | 1,208 | $359,900 | $297 | 11 days |
Sold homes
Closed in the last 12 monthsPrice vs. living area
Each dot is one of the 250 newest homes. Hover a dot for its address, click it to see the home.
8 homes didn’t report living area and aren’t shown.
2 homes are larger or pricier than this chart’s scale and aren’t shown.
How long homes took to sell
Number of homes by days on market.
Bedroom mix
Number of homes by bedroom count.
48 homes didn’t report bedrooms and aren’t shown.
Highest price per ft²
Top 7 homes among the newest.
Sold price vs. list price
How close homes sold to their asking price.
All sold listings (1,026)
The map shows the 250 newest homes with a location. Click a marker for the home.
| Address | Beds | Baths | Living ft² | Sold price | Sold / list | $ / ft² | Days to sell | Sold date |
|---|---|---|---|---|---|---|---|---|
| 7640 Village Green DrWinter Park, FL 32792 | 3 | 2 | 1,631 | $445,000 | 101.4% | $272 | 13 days | Nov 13, 2026 |
| 2667 Cochise TrailWinter Park, FL 32789 | 4 | 3 | 2,868 | $900,000 | 91.4% | $313 | 76 days | Nov 13, 2026 |
| 433 Gilbert RoadWinter Park, FL 32792 | 3 | 2 | 1,800 | $660,000 | 98.5% | $366 | 78 days | Nov 13, 2026 |
| 1261 Indiana AvenueWinter Park, FL 32789 | 3 | 3 | 1,660 | $525,000 | 97.2% | $316 | 154 days | Nov 13, 2026 |
| 1211 Schultz AvenueWinter Park, FL 32789 | 3 | 2 | 1,085 | $475,000 | 100.0% | $437 | 12 days | Nov 12, 2026 |
| 2302 Barbados DriveWinter Park, FL 32792 | 2 | 2 | 1,544 | $265,000 | 96.4% | $171 | 41 days | Nov 12, 2026 |
| 952 Moss LaneWinter Park, FL 32789 | 4 | 5 | 3,474 | $1,235,000 | 93.6% | $355 | 17 days | Nov 12, 2026 |
| 645 Pansy AvenueWinter Park, FL 32789 | 4 | 5 | 3,661 | $2,250,000 | 94.1% | $614 | 27 days | Nov 12, 2026 |
| 1138 S Pennsylvania AvenueWinter Park, FL 32789 | 3 | 3 | 2,434 | $875,000 | 94.6% | $359 | 125 days | Nov 12, 2026 |
| 1552 Little Wren LaneWinter Park, FL 32792 | 3 | 3 | 2,308 | $440,000 | 100.0% | $190 | 2 days | Nov 10, 2026 |
Questions about this market?
These numbers move every month. For what they mean for your home, or for a home you have your eye on, get in touch.