What $750K Buys in Winter Garden, Windermere and Clermont FL

In November 2026, $750,000 sits above the typical sale price in Winter Garden and Clermont and below it in Windermere. Using recent sold data, that budget works out to roughly 2,900 to 3,000 square feet in Winter Garden, about 3,400 to 3,500 square feet in Clermont, and somewhere between 1,750 and 2,700 square feet in Windermere. Those are estimates built from medians, and any one house can land above or below them. They do show how far the same budget stretches across three neighboring cities.

The figures below come from three public sources, each labeled. Redfin reports sold data for the three months ending September 2026. A Stellar MLS InfoSparks report published November 2, 2026 by Premier Sotheby's International Realty covers single-family sales for October 2026. A MaxLife Realty report built on Stellar MLS covers Clermont's last 12 months as of November 2, 2026. None of these numbers come from Bella Trae Realty's own MLS pull.

The Three Medians Side by Side

Winter Garden: Redfin puts the median sale price at about $600,000 for the three months ending September 2026, up 7.1% from a year earlier, with a median of $251 per square foot. The Stellar MLS report shows a single-family median of $646,250 for October 2026 at $259 per square foot, with homes selling in a median 32 days.

Clermont: Redfin shows a median of about $442,000 for the same three months, down 4.0% from a year earlier, at $216 per square foot. The MaxLife report shows a 12-month median sold price of $470,000 at $219 per square foot, a 28-day median time on market and a 98.3% sold-to-list ratio.

Windermere: the sources split widely here. Redfin shows a median of about $1.2 million for the three months ending September 2026, based on a small sample of 19 sales in September. The Stellar MLS report shows a single-family median of $795,000 for October 2026 at $278 per square foot. Small sales counts swing medians hard, so treat Windermere as a range.

Winter Garden at $750K

Dividing $750,000 by the $251 to $259 price per square foot gives roughly 2,900 to 3,000 square feet at the median rate. In practice that budget puts you in the upper half of the Winter Garden market, since the single-family median sits near $646,000. Buyers at this level often compare newer Horizon West neighborhoods against established 34787 subdivisions closer to Plant Street and the West Orange Trail.

What changes the math: lot size, a pool, the age of the roof and whether the community carries a CDD assessment on the tax bill. Two homes listed at $750,000 can have very different monthly costs once those are added in. Ask for the tax bill and HOA documents early, before you write an offer.

Clermont at $750K

Clermont gives the most space per dollar of the three. At $216 to $219 per square foot, $750,000 works out to about 3,400 to 3,500 square feet at the median rate. With the 12-month median sold price at $470,000, a $750,000 budget sits well above the typical Clermont sale.

That headroom is why buyers at this price often look at lakefront and lake-view homes on the Clermont Chain of Lakes, larger lots in the hills south of town, or golf communities. Lakefront and hilltop homes trade at a premium over the city median, so the square footage will shrink on those streets. If you are near the water, ask about the flood zone and any seawall or dock condition before you commit.

Windermere at $750K

Windermere is the tightest fit of the three. At the October 2026 single-family rate of $278 per square foot, $750,000 lines up with about 2,700 square feet. At Redfin's three-month figure of $426 per square foot, it lines up with about 1,750. The gap comes from which sales landed in each window, with lakefront and gated estates pulling the Redfin number up.

With a single-family median of $795,000, a $750,000 budget sits just under the middle of the market. Expect to weigh trade-offs: an older home on a larger lot, a newer home in a Windermere-address subdivision outside the town limits, or a smaller home closer to the Butler Chain of Lakes. Confirm whether a property sits inside the Town of Windermere or only carries the mailing address, since that affects which rules and services apply.

How Hard to Negotiate in Each City

Redfin's sale-to-list figures for the three months ending September 2026 give a rough read on leverage. Clermont homes sold at 98.7% of list, Winter Garden at 97.7% and Windermere at 95.5%. Redfin also reports that 34.0% of Clermont homes, 40.5% of Winter Garden homes and 35.6% of Windermere homes had a price drop.

In plain terms, Windermere buyers have had the most room to negotiate off list price, and Clermont sellers have held price best. These are citywide averages. A well-priced home in any of the three can still draw more than one offer, and a stale listing can take a deeper cut.

Making $750K Work for You

Start with the monthly payment you want, then work back to price, since taxes, insurance, HOA dues and any CDD can add hundreds of dollars a month between homes at the same list price. Get a written insurance quote on any house you are serious about, especially one with an older roof. Compare the same square footage across cities before you settle on one.

Bella Trae Realty works across Winter Garden, Windermere and Clermont, so we can line up homes at your budget in all three and show you the real carrying costs side by side. Contact Bella Trae Realty today to see what $750,000 buys on the streets you care about.

Sources: Redfin housing market pages for Winter Garden, Windermere and Clermont, FL (three months ending September 2026), retrieved November 3, 2026. Stellar MLS InfoSparks single-family data for October 2026, compiled by Premier Sotheby's International Realty (published November 2, 2026). MaxLife Realty Clermont report based on Stellar MLS, last 12 months as of November 2, 2026. Square footage figures are Bella Trae Realty calculations ($750,000 divided by the median price per square foot) and are estimates only. Photo: "Downtown Winter Garden (Plant Street - June 10, 2024)" by Freeholdman12, CC BY 4.0, via Wikimedia Commons.