Winter Garden vs Windermere (2026): How Do Home Prices, Taxes, Commutes & Home Types Compare?
Tile-roof homes with pools around a fountain pond in Keene's Pointe, Windermere, with a large lake beyond.
Image: Jared Jones Team
Quick answer
Winter Garden ZIP 34787 homes sold for a median $607,500 (1,956 sales, 12 months ending Oct 2, 2026) and Windermere ZIP 34786 homes for $817,250 (638 sales, 12 months ending Oct 19, 2026), per Stellar MLS. Inside town limits, Windermere's median was $1,155,000 (60 sales), versus $645,000 in Winter Garden city limits.
| Fact | Figure |
|---|---|
| Closed sales, 12 months (ZIPs) | Winter Garden 34787: 1,956; Windermere 34786: 638 |
| Median sold price (ZIPs) | Winter Garden 34787: $607,500; Windermere 34786: $817,250 |
| Middle half of sale prices, Windermere 34786 | $555,000–$1,330,000 |
| Median price per sq ft (ZIPs) | Winter Garden: $254.63; Windermere: $288.89 |
| Median heated sq ft (ZIPs) | Winter Garden: 2,472; Windermere: 2,884 |
| Detached-home median, sales (ZIPs) | Winter Garden: $681,758 (1,598); Windermere: $962,250 (532) |
| Townhome median, sales (ZIPs) | Winter Garden: $429,840 (358); Windermere: $391,000 (106) |
| Median days to contract (ZIPs) | Winter Garden: 41; Windermere: 38 |
| Median sale-to-list (ZIPs) | Winter Garden: 98%; Windermere: 97% |
| Median year built, homes sold (ZIPs) | Winter Garden: 2019; Windermere: 2006 |
| Sales with a private pool (ZIPs) | Winter Garden: 18.9%; Windermere: 46.7% |
| Active listings, median list (ZIPs) | Winter Garden: 565 ($684,990), as of Oct 2, 2026; Windermere: 217 ($1,189,000), as of Oct 20, 2026 |
| Months of supply, 12-month pace (ZIPs) | Winter Garden: 3.5; Windermere: 4.1 |
| Inside city/town limits: closed sales and median | City of Winter Garden: 559 at $645,000; Town of Windermere: 60 at $1,155,000 |
| Inside city/town limits: median price per sq ft | City of Winter Garden: $249.57; Town of Windermere: $414.70 |
| Windermere 34786 outside town limits (unincorporated) | 565 sales at $753,000 |
| City/town millage | City of Winter Garden: 4.8565; Town of Windermere: 3.7425 |
| Total millage inside city/town limits | Winter Garden: 16.2943; Town of Windermere: 15.4839 |
| Total millage, most unincorporated 34786 parcels | 16.1366 or 16.3894 (by mill code) |
| Drive between the two (City Hall to Town Hall) | About 16–17 min, 8.3–9.2 miles |
| Drive to Orlando City Hall | Winter Garden: about 23–24 min; Windermere: about 22 min |
| Drive to Magic Kingdom ticket and transportation center | Winter Garden: about 30–38 min; Windermere: about 25–29 min |
| Public schools | Orange County Public Schools for both; confirm assignment by address |
Sources: Stellar MLS (closings Oct 2, 2025–Oct 2, 2026 for ZIP 34787 and Oct 20, 2025–Oct 19, 2026 for ZIP 34786; active listings as of Oct 2, 2026 for ZIP 34787 and Oct 20, 2026 for ZIP 34786; pulled Oct 2, 2026 (34787) and Oct 20, 2026 (34786); analysis: Jared Jones Team); Orange County Property Appraiser parcel data (city codes) and 2025 Final Millage (checked Oct 7, 2026); free-flow map check (Oct 7, 2026); OCPS school locator.
Geography: ZIP rows compare Winter Garden ZIP 34787 with Windermere ZIP 34786. Both ZIPs reach well beyond their municipal limits: about 89% of Windermere 34786 sales were in unincorporated Orange County, and Winter Garden 34787 includes much of Horizon West. The city and town rows use Orange County Property Appraiser city codes to keep only sales inside City of Winter Garden or Town of Windermere limits. Drive times start at each City Hall or Town Hall.
How do Winter Garden and Windermere home prices compare?
Over the 12 months ending Oct 2, 2026, Winter Garden ZIP 34787 recorded 1,956 detached-home and townhome sales at a median $607,500. Over the 12 months ending Oct 19, 2026, Windermere ZIP 34786 recorded 638 sales at a median $817,250 (Stellar MLS, same method for both ZIPs). Per square foot, the medians were $254.63 in Winter Garden and $288.89 in Windermere, and the median home sold was 2,472 square feet in Winter Garden and 2,884 in Windermere. The middle half of Windermere 34786 sales landed between $555,000 and $1,330,000.
Inside municipal limits the gap is wider. The Town of Windermere had 60 sales at a median $1,155,000, or $414.70 per square foot, while the City of Winter Garden had 559 sales at a median $645,000, or $249.57 per square foot. Sixty sales is a small sample, so treat the town figure as a range marker, not a monthly trend. The 565 Windermere 34786 sales in unincorporated Orange County had a median $753,000.
Homes went under contract in a median 41 days in Winter Garden 34787 and 38 days in Windermere 34786, and sold at a median 98% and 97% of list price. We use the MLS Days to Contract field because many builder closings are entered at or near closing, which pulls cumulative days on market toward zero.
What types and ages of homes sell in each area?
Detached homes made up 1,598 of Winter Garden 34787's 1,956 sales, at a median $681,758, and townhomes made up 358 at a median $429,840. In Windermere 34786, 532 detached homes sold at a median $962,250 and 106 townhomes at a median $391,000 (12 months ending Oct 19, 2026).
The median home sold was built in 2019 in Winter Garden 34787 and in 2006 in Windermere 34786. Inside Town of Windermere limits, all 60 sales were single-family homes, with a median year built of 1986–87 and a median 2,908 square feet. About 18.9% of Winter Garden 34787 sales had a private pool, compared with 46.7% in Windermere 34786 and 70.0% inside town limits. The plat names with the most 34786 sales outside town limits were Keene's Pointe, Palms at Windermere, Preston Square, Windermere Terrace and Isleworth.
What are the Town of Windermere and the City of Winter Garden like as places?
The Town of Windermere is a small municipality on the Butler Chain of Lakes, with its Town Hall at 614 Main Street. A 2025 Florida Senate resolution marking the town's 100th anniversary notes that it was incorporated in 1925, that it is designated a Tree City USA, and that the Butler Chain of Lakes was the first lake system in Florida designated an Outstanding Florida Water, in 1985. The Orange County Property Appraiser lists 1,458 parcels inside town limits.
The City of Winter Garden's City Hall is on Plant Street in its historic downtown, and the city's ZIP 34787 also takes in newer communities to the south, many of them in unincorporated Horizon West. For that side of the area, see Plant Street vs Horizon West.
Two-story homes around a fountain pond in Black Lake Estates, Winter Garden, with a large lake beyond.
Image: Jared Jones Team
How do property taxes compare?
The Town of Windermere's rate is lower. On the Orange County Property Appraiser's 2025 final millage table, the Town of Windermere levied 3.7425 mills and the City of Winter Garden 4.8565 mills. Total millage inside town limits was 15.4839 mills (every town parcel is in mill code 75), versus 16.2943 mills inside Winter Garden city limits.
On $100,000 of taxable value, that works out to about $1,548 in the town and about $1,629 in the city before flat assessments such as garbage or stormwater. Most Windermere 34786 homes sit outside town limits in unincorporated Orange County, at 16.1366 or 16.3894 total mills depending on mill code, so check the mill code on each parcel's Property Appraiser record. Our Winter Garden property taxes guide explains homestead, Save Our Homes and portability.
How do commutes compare?
Windermere sits a little closer to downtown Orlando and to Walt Disney World. In a free-flow map check on Oct 7, 2026, the drive from Windermere Town Hall to Orlando City Hall took about 22 minutes, versus about 23 to 24 minutes from Winter Garden City Hall. To the Magic Kingdom ticket and transportation center, it took about 25 to 29 minutes from Windermere and about 30 to 38 minutes from Winter Garden, where the two routing engines picked different routes. The drive between the two halls took about 16 to 17 minutes.
These are no-traffic estimates, so rush-hour trips usually run longer. Drive your own route at your real departure time. Our commute and roads guide covers SR 429 and SR 516 work in more detail.
What should buyers check before choosing?
- Town or city limits vs unincorporated: the mailing city does not tell you the tax district. Most Windermere 34786 homes are outside town limits.
- Utility provider for water, sewer and power at the specific address.
- Flood zone and insurance quotes for the exact property, especially on a lake.
- HOA and any CDD assessment on the parcel.
- Assigned Orange County public schools, confirmed by address with OCPS.
Selling in one area to buy in the other?
Plan the sale and purchase together so your timing and cash line up. Windermere 34786 had 217 active listings as of Oct 20, 2026 (median list $1,189,000), about 4.1 months of supply, and Winter Garden 34787 had 565 as of Oct 2, 2026 (median list $684,990), about 3.5 months. Review Winter Garden days on market by price band and what it costs to sell in Winter Garden. Weighing Winter Garden against Windermere? Call or text 407-706-5000 and we will pull side-by-side comps for the homes you are considering.
Frequently asked questions
How do Winter Garden and Windermere home prices compare?
Winter Garden ZIP 34787 homes sold for a median $607,500 across 1,956 sales (12 months ending Oct 2, 2026), and Windermere ZIP 34786 homes for a median $817,250 across 638 sales (12 months ending Oct 19, 2026), per Stellar MLS. Per square foot, the medians were $254.63 and $288.89. Home size and age differ between the two.
What do homes cost inside Town of Windermere limits?
Over the 12 months ending Oct 19, 2026, 60 homes inside Town of Windermere limits sold for a median $1,155,000, or $414.70 per square foot, per Stellar MLS sales matched to Orange County Property Appraiser city codes. All were single-family homes. Inside City of Winter Garden limits, 559 homes sold for a median $645,000 over the 12 months ending Oct 2, 2026.
Is a Windermere address inside the Town of Windermere?
Usually not. About 89% of Windermere ZIP 34786 sales over the 12 months ending Oct 19, 2026 were in unincorporated Orange County, not the town. The Orange County Property Appraiser record shows each parcel’s city code and mill code, which set the tax rate and local government. Check it before you write an offer.
Which has higher property taxes, Winter Garden or Windermere?
Inside municipal limits, Winter Garden is higher. The Orange County Property Appraiser’s 2025 final table shows 3.7425 town mills in Windermere and 4.8565 city mills in Winter Garden, with totals of 15.4839 and 16.2943 mills. Most Windermere 34786 homes are unincorporated, at 16.1366 or 16.3894 total mills.
Are Winter Garden and Windermere in the same county and school district?
Yes. Both Winter Garden and Windermere are in Orange County, and both are served by Orange County Public Schools. School assignments are set by address, so confirm the assigned schools for any specific home with the OCPS school locator before you write an offer.
How far apart are Winter Garden and Windermere?
In a free-flow map check on Oct 7, 2026, the drive from Winter Garden City Hall to Windermere Town Hall took about 16 to 17 minutes, covering 8.3 to 9.2 miles. From Windermere Town Hall to Orlando City Hall took about 22 minutes. These are no-traffic estimates, so rush-hour trips usually take longer.
Can one agent help me sell in one area and buy in the other?
Yes. The Jared Jones Team works across Winter Garden, Windermere and the rest of west Orange County, so one team can price and list your current home and help you buy in the other area. Call or text 407-706-5000 to plan the timing of both moves.
Sources
- Orange County Property Appraiser, 2025 Final Millage Rates
- Orange County Property Appraiser: GIS parcel data (city and mill codes) (checked Oct 7, 2026)
- Town of Windermere: Town Hall contact (checked Oct 7, 2026)
- Florida Senate: SR 1884 (2025), Town of Windermere 100th anniversary (checked Oct 7, 2026)
- Free-flow drive-time map check (OpenStreetMap routing), Oct 7, 2026
- Stellar MLS (ZIP 34787 closings Oct 2, 2025–Oct 2, 2026, active listings as of Oct 2, 2026; ZIP 34786 closings Oct 20, 2025–Oct 19, 2026, active listings as of Oct 20, 2026); analysis: Jared Jones Team
- Jared Jones Team, Brokered by eXp Realty, Oct 2026
Related Wave 1 guides
- Winter Garden & Horizon West Real Estate (2026) hub
- Winter Garden vs Ocoee (2026)
- Plant Street vs Horizon West
- Winter Garden Property Taxes Explained (2026)
- Cost of Living in Winter Garden, FL (2026)
- Horizon West Commute & Roads Guide 2026
- What Is the Winter Garden Housing Market Doing in October 2026?
- How Long Does It Take to Sell a Home in Winter Garden? (2026)
- Seller Closing Costs in Winter Garden (2026)
- Winter Garden Real Estate
- Windermere Real Estate
Buying or selling in Winter Garden or Horizon West?
Get street-level pricing, an honest commute read and a clear plan to close. Call or text 407-706-5000.