Moving to Winter Park, Florida: The 2026 Data Guide
As of 2026-10-02, the median home sold in Winter Park, Florida over the last 12 months went for $560,000 (661 closings across 305 communities in Momentum’s MLS record), about $302 per square foot for a median 1,829-sq-ft home built around 1973. Homes currently listed have been on the market a median of 26 days, and with 240 active listings against that sales pace the city is carrying roughly 4.4 months of supply. Sellers have been getting about 96% of their original asking price. That median is 40% above the median across Momentum’s Florida and Georgia coverage.
Winter Park right now — October 2026
Live pages for your move: 362 homes for sale in Winter Park · Luxury homes · New construction · Condos (91) · Townhomes (23) · Homes by ZIP (2 ZIPs) · New listings this week · Price reductions · What your budget buys in Orange County · Cost of living · Best neighborhoods · Property tax · Flood zones by neighborhood · Orange County homes for sale.
MLS closed sales and live inventory, Momentum Research; refreshed nightly. Updated October 2, 2026.
What your budget buys in Winter Park
Three price points from 649 recent Winter Park closings in our record, each showing what actually closed within 10% of that price:
- Around $360,000: the typical sale in this band was a 3-bed, 2-bath home of about 1,359 sq ft, built around 1964 (51 sales).
- Around $560,000: the typical sale in this band was a 3-bed, 2-bath home of about 1,678 sq ft, built around 1965 (66 sales).
- Around $1,300,000: the typical sale in this band was a 4-bed, 3.5-bath home of about 2,821 sq ft, built around 2013 (37 sales).
The real monthly cost of owning in Winter Park
Take the median $560,000 home with 20% down at today’s 7.28% 30-year rate: principal and interest run about $3,065/month. Orange County’s typical total millage is 16.67 mills, so after the $50,000 homestead exemption the property tax is roughly $8,504/year ($709/month) for a new owner — the seller’s capped bill on the listing will be lower and is not your number. Citizens Property Insurance’s average premium in Orange County is about $1,409/year; private-market quotes vary with roof age and wind mitigation. 22% of current Winter Park listings carry an HOA, with a median of $372/month where one applies. All in, budget on the order of $3,891/month to own the median Winter Park home.
For the full worksheet — taxes by scenario, the homestead exemption, and how the Save Our Homes cap works after year one — see the Orange County property tax guide and our home insurance by county map.
Where people are buying: Winter Park’s most active communities
The communities with the most closings in the last 12 months, with each one’s median sale and how long its current listings have been on the market. Every name links to that community’s own guide with live listings.
| Community | Sales (12 mo) | Median | Days listed |
|---|---|---|---|
| Winter Park Pines | 23 | $600,000 | 19 |
| Four Seasons Condo | 21 | $180,000 | 35 |
| Country Lane | 14 | $386,000 | 10 |
| Comstock Park | 13 | $1,700,000 | 25 |
| Winter Park Woods Condo | 13 | $78,000 | 12 |
| Charmont | 11 | $1,000,500 | 35 |
| Lost Creek | 11 | $525,000 | 23 |
| Casa Aloma | 10 | $436,200 | 35 |
Winter Park by ZIP code
Sales and medians by ZIP over the same 12 months: 32789 (395 sales, median $955,000), 32792 (247 sales, median $410,000).
What’s for sale: property types, new construction, and age of homes
Of the last 12 months of sales, 72% were single-family homes, 5% townhomes or villas, and 23% condos. New construction accounted for 5% of closings. The housing stock skews older: 16% of homes sold were built in 2015 or later and 59% before 1980.
Getting around from Winter Park
Measured from the center of Winter Park’s recent sales: Orlando International Airport (MCO) is about 12 miles; Daytona Beach is about 46 miles; Lakeland is about 54 miles; Melbourne is about 57 miles. Distances are straight-line; drive times depend on the corridor and time of day.
Schools, taxes, and insurance: where to verify
School assignments change; check the Orange County school grades page for the district’s current grades, and confirm zoning for a specific address directly with the district. Property tax figures on this page use Orange County’s typical millage of 16.67; municipal and special-district millage varies inside the county. Insurance uses Citizens’ Orange County average of $1,409/year; a wind-mitigation inspection and roof age can move a private quote a long way in either direction.
Winter Park: the case for and against
What works in Winter Park’s favor
- homes move quickly (median 26 days listed), so well-priced homes get competition
- insurance is comparatively manageable here (Citizens average $1,409/year)
- most listings (78%) have no HOA
- no state income tax, and Florida’s Save Our Homes cap limits assessment growth once you homestead
What to plan for
- prices run 40% above the statewide median in our coverage
- property taxes reset to your purchase price, so never budget off the seller’s bill
Your Winter Park relocation toolkit
- Homes for sale in Winter Park right now
- Cost of living in Winter Park
- Best neighborhoods in Winter Park
- New construction in Winter Park
- Find an agent in Winter Park
- Winter Park ZIP codes with prices
- Search every Winter Park community
Common questions about moving to Winter Park
How much does a house cost in Winter Park, FL?
What does it cost per month to own a home in Winter Park?
What are property taxes like in Winter Park?
Is Winter Park a buyer's or seller's market right now?
Is there a lot of new construction in Winter Park?
Does Florida have a state income tax?
Sales figures are Momentum Realty’s MLS record of closings in Winter Park communities over the trailing 12 months (community snapshots as of their last refresh; price-band examples from the most recent closings on file); tax and insurance figures are Orange County data. Estimates, not guarantees; verify before relying on them. General relocation guidance, not financial advice. Equal Housing Opportunity.