Homes for Sale $300K to $500K in Windermere, FL
This page tracks every Windermere listing with an asking price between $300,000 and $500,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.
53 homes listed between $300,000 and $500,000 are for sale or pending in Windermere, FL today across 33 communities. The median asking price is $409,900, from $320,000 to $499,990. Listings in Windermere without that feature have a median of $1,289,000. Most listings right now: Lake Sawyer South Ph 03 (4), Windermere Trls Prcl 3 (3), Carrington (3). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Windermere: the listings
41 active listings match today (18% of Windermere inventory), median asking $410,000, $251/sq ft, median 36 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Windermere
The most expensive $300k–$500k homes in Windermere
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 7867 Berkshire Oak Alley | $499,990 | 2,221 | Westside Village |
| 13535 Bramham Lane | $489,900 | 1,820 | Lakes Windermere Peachtree |
| 7668 Fairgrove Avenue | $485,000 | 1,866 | — |
| 11861 Vermillion Avenue | $475,000 | 1,600 | windermere trails |
| 12353 Via Derna Place | $460,000 | 1,974 | Carrington |
| 11951 Vermillion Avenue | $459,000 | 1,539 | windermere trails |
| 13755 Bravante Alley | $455,000 | 2,091 | Vineyards Of Horizons West |
| 9764 Gotha Road | $450,000 | 1,216 | Gotha Town |
| 8470 Iron Mountain Trail | $449,900 | 1,664 | windermere trails |
| 12333 Via Derna Place | $449,000 | 1,919 | Carrington |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 41 | 100% |
Windermere homes $300K–$500K by community
Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.
| Community | Homes $300K–$500K | New build | Median list | From |
|---|---|---|---|---|
| Lake Sawyer South Ph 03 | 4 | 0 | $374,450 | $350,000 |
| Windermere Trls Prcl 3 | 3 | 0 | $459,000 | $449,900 |
| Carrington | 3 | 0 | $449,000 | $430,000 |
| Windermere Sound Ph 2 | 3 | 0 | $445,000 | $440,000 |
| Windermere Trls Prcl 3 | 2 | 0 | $456,500 | $438,000 |
| Lake Burden South Ph I | 2 | 0 | $436,500 | $424,000 |
| Lake Burden South Ph 2 | 2 | 0 | $424,500 | $410,000 |
| Tennyson Pk/Summerport | 2 | 0 | $390,000 | $375,000 |
| Lakes/Windermere Lake Reams Twnh | 2 | 0 | $389,950 | $379,900 |
| Lakes/Windermere-Lk Reams Twhm | 2 | 0 | $379,500 | $360,000 |
| Lake Sawyer South Ph 3 | 2 | 0 | $349,500 | $349,000 |
| Lakeside/Lks/Windermere | 2 | 0 | $326,000 | $325,000 |
| Lakeside At Lakes Of Windermere | 2 | 0 | $322,500 | $320,000 |
| Westside Village | 1 | 0 | $499,990 | $499,990 |
| Lakes/Windermere-Peachtree | 1 | 0 | $489,900 | $489,900 |
| Windermere Sound Ph 2 | 1 | 0 | $485,000 | $485,000 |
| Windermere Trls Ph 3B | 1 | 0 | $470,000 | $470,000 |
| Vineyards/Horizons West Ph 2B | 1 | 0 | $455,000 | $455,000 |
| Gotha Town | 1 | 0 | $450,000 | $450,000 |
| Ashlin Park Ph 2 | 1 | 0 | $445,000 | $445,000 |
| Vineyards/Horizons West Ph 4 | 1 | 0 | $444,900 | $444,900 |
| Preston Square | 1 | 0 | $444,900 | $444,900 |
| Lakes Of Windermere Lake Reams Townhomes Phase 3 | 1 | 0 | $410,000 | $410,000 |
| Oasis Cove Ii/Lakeside Village Ph | 1 | 0 | $399,999 | $399,999 |
| Whickham Park | 1 | 0 | $399,000 | $399,000 |
| Summerport Edens Hammock | 1 | 0 | $399,000 | $399,000 |
| Lakes/Windermere-Lk Reams Twnh | 1 | 0 | $394,900 | $394,900 |
| Summerport Ph 03 | 1 | 0 | $379,900 | $379,900 |
| Southbridge Village | 1 | 0 | $375,000 | $375,000 |
| Oasis Cove/Lakeside Village Ph Vii | 1 | 0 | $359,900 | $359,900 |
| Wickham Park 04 05 06 09 10 11 12 01 | 1 | 0 | $354,900 | $354,900 |
| Belmere Village G2 48 65 | 1 | 0 | $349,900 | $349,900 |
| Oasis Cove I/Lakeside Village Ph 01 | 1 | 0 | $330,000 | $330,000 |
Where this band sits in the market
The answer block above shows how the median of this band compares with the rest of the city’s listings, which tells you whether $300,000–$500,000 is the middle of the market here or the top of it. Within the band, compare on price per square foot and year built: newer subdivisions usually price higher per foot with lower expected maintenance, older ones the reverse. Each community page carries the HOA and CDD picture, the year-built range and the sales history, so two homes at the same price can be told apart in a few minutes.
Questions to ask about any listing in this band
What are the total monthly carrying costs (taxes, insurance, HOA, CDD) and how do they compare with a similar home two communities over? What is the age of the roof, HVAC and water heater? Is the community’s HOA financially healthy (reserves, no pending assessment)? How many days has the listing been on the market and has the price moved? A local agent who works the area will know which communities in this band are trading at asking and which are negotiating.
Common questions
How many homes listed between $300,000 and $500,000 are for sale in Windermere?
What do homes $300K–$500K cost in Windermere?
Which Windermere community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
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Live data: Stellar MLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Windermere, FL whose MLS record reports an asking price between $300,000 and $500,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.