Moving to Winter Garden, Florida: The 2026 Data Guide
As of 2026-09-27, the median home sold in Winter Garden, Florida over the last 12 months went for $575,000 (1,337 closings across 329 communities in Momentum’s MLS record), about $255 per square foot for a median 2,216-sq-ft home built around 2017. Homes currently listed have been on the market a median of 40 days, and with 1,663 active listings against that sales pace the city is carrying roughly 14.9 months of supply. Sellers have been getting about 96% of their original asking price. That median is 44% above the median across Momentum’s Florida and Georgia coverage.
Winter Garden right now — September 2026
Live pages for your move: 709 homes for sale in Winter Garden · Luxury homes · New construction · Condos (117) · Townhomes (112) · Homes by ZIP (1 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 September 27, 2026.
What your budget buys in Winter Garden
Three price points from 995 recent Winter Garden closings in our record, each showing what actually closed within 10% of that price:
- Around $460,000: the typical sale in this band was a 3-bed, 2.5-bath home of about 1,788 sq ft, built around 2019 (195 sales).
- Around $575,000: the typical sale in this band was a 4-bed, 2.5-bath home of about 2,306 sq ft, built around 2016 (204 sales).
- Around $780,000: the typical sale in this band was a 4-bed, 3.5-bath home of about 3,046 sq ft, built around 2018 (175 sales).
The real monthly cost of owning in Winter Garden
Take the median $575,000 home with 20% down at today’s 7.03% 30-year rate: principal and interest run about $3,070/month. Orange County’s typical total millage is 16.67 mills, so after the $50,000 homestead exemption the property tax is roughly $8,754/year ($729/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. 74% of current Winter Garden listings carry an HOA, with a median of $212/month where one applies. All in, budget on the order of $4,129/month to own the median Winter Garden home including a typical HOA.
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 Garden’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 |
|---|---|---|---|
| Waterleigh | 183 | $575,000 | 40 |
| Serenade at Ovation | 47 | $451,542 | 84 |
| Parkview at Hamlin | 42 | $479,740 | 37 |
| Watermark | 35 | $695,000 | 62 |
| Lake Star At Ovation | 31 | $629,990 | 27 |
| Hickory Hammock | 28 | $907,500 | 22 |
| Del Webb Oasis | 27 | $480,000 | 68 |
| Hamlin Reserve | 26 | $521,000 | 38 |
Winter Garden by ZIP code
Sales and medians by ZIP over the same 12 months: 34787 (989 sales, median $575,000).
What’s for sale: property types, new construction, and age of homes
Of the last 12 months of sales, 79% were single-family homes, 18% townhomes or villas, and 3% condos. New construction accounted for 36% of closings, led by Waterleigh, Serenade at Ovation, Parkview at Hamlin, Lake Star At Ovation, Northlake At Ovation. The housing stock skews newer: 60% of homes sold were built in 2015 or later and 5% before 1980.
Getting around from Winter Garden
Measured from the center of Winter Garden’s recent sales: Downtown Orlando is about 15 miles; Orlando International Airport (MCO) is about 19 miles; Lakeland is about 38 miles; Ocala 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 Garden: the case for and against
What works in Winter Garden’s favor
- homes move quickly (median 40 days listed), so well-priced homes get competition
- about 14.9 months of supply gives buyers room to negotiate
- 36% of sales are new construction, so builder incentives and warranties are part of the market
- insurance is comparatively manageable here (Citizens average $1,409/year)
- no state income tax, and Florida’s Save Our Homes cap limits assessment growth once you homestead
What to plan for
- prices run 44% above the statewide median in our coverage
- 74% of listings carry an HOA (median $212/month)
- property taxes reset to your purchase price, so never budget off the seller’s bill
Your Winter Garden relocation toolkit
- Homes for sale in Winter Garden right now
- Cost of living in Winter Garden
- Best neighborhoods in Winter Garden
- New construction in Winter Garden
- Find an agent in Winter Garden
- Winter Garden ZIP codes with prices
- Search every Winter Garden community
Common questions about moving to Winter Garden
How much does a house cost in Winter Garden, FL?
What does it cost per month to own a home in Winter Garden?
What are property taxes like in Winter Garden?
Is Winter Garden a buyer's or seller's market right now?
Is there a lot of new construction in Winter Garden?
Does Florida have a state income tax?
Sales figures are Momentum Realty’s MLS record of closings in Winter Garden 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.