Homes for Sale $300K to $500K in Winter Park, FL
This page tracks every Winter Park 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.
64 homes listed between $300,000 and $500,000 are for sale or pending in Winter Park, FL today across 50 communities. The median asking price is $429,950, from $305,000 to $499,900. Listings in Winter Park without that feature have a median of $836,000. Most listings right now: Garden Lake Estates Unit 1 (4), Aloma (2), Woodcrest Unit 5 (2). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Winter Park: the listings
40 active listings match today (14% of Winter Park inventory), median asking $434,950, $294/sq ft, median 33 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Winter Park
The most expensive $300k–$500k homes in Winter Park
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 2231 Nairn Drive | $499,000 | 1,088 | Aloma |
| 230 Strathy Lane | $499,000 | 920 | Aloma |
| 5316 Halyard Court | $495,000 | 1,380 | — |
| 1660 Gladiolas Drive | $495,000 | 2,047 | — |
| 3020 Nicholson Drive | $495,000 | 1,756 | Wrenwood |
| 981 Aragon Avenue | $494,999 | 857 | Seville Park |
| 2715 Prince John Road | $494,900 | 1,565 | winter park pines |
| 525 Ololu Drive | $490,900 | 1,786 | Killarney Circle |
| 2217 Sussex Road | $485,000 | 2,092 | — |
| 1660 Orange Avenue | $479,900 | 1,614 | Orwin Manor Westminster |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 40 | 100% |
Winter Park 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 |
|---|---|---|---|---|
| Garden Lake Estates Unit 1 | 4 | 0 | $439,995 | $389,950 |
| Aloma | 2 | 0 | $499,000 | $499,000 |
| Woodcrest Unit 5 | 2 | 0 | $487,450 | $479,900 |
| Winter Park Pines Rep | 2 | 0 | $484,950 | $475,000 |
| Orwin Manor Westminster Sec | 2 | 0 | $479,450 | $479,000 |
| Garden Lake Estates Unit 3 | 2 | 0 | $434,949 | $399,999 |
| Winter Woods Unit 01 | 2 | 0 | $430,000 | $375,000 |
| Eastbrook Sub Unit 06 2Nd Rep | 2 | 0 | $399,000 | $379,000 |
| Dubsdread Heights | 2 | 0 | $388,500 | $329,000 |
| Stansbury Estates | 2 | 0 | $388,500 | $328,000 |
| Eastbrook Sub | 2 | 0 | $379,000 | $368,000 |
| Ridge High Sub | 2 | 0 | $362,500 | $360,000 |
| Flamingo Shores | 1 | 0 | $499,900 | $499,900 |
| Terrazo Del Sol | 1 | 0 | $499,000 | $499,000 |
| Wrenwood Unit 3 3Rd Add | 1 | 0 | $495,000 | $495,000 |
| Seville Park | 1 | 0 | $494,999 | $494,999 |
| Killarney Circle | 1 | 0 | $490,900 | $490,900 |
| Cedar Ridge | 1 | 0 | $475,000 | $475,000 |
| Metzingers Add | 1 | 0 | $475,000 | $475,000 |
| Killarney Bay Condo | 1 | 0 | $475,000 | $475,000 |
| Winter Park Forest | 1 | 0 | $474,900 | $474,900 |
| Casa Aloma | 1 | 0 | $464,000 | $464,000 |
| Bel Aire Pines | 1 | 0 | $449,900 | $449,900 |
| Tanglewood Rep | 1 | 0 | $439,900 | $439,900 |
| Bel Aire | 1 | 0 | $439,900 | $439,900 |
| Pines | 1 | 0 | $439,900 | $439,900 |
| Village Green | 1 | 0 | $439,000 | $439,000 |
| Albert Lee Ridge 1St Add | 1 | 0 | $439,000 | $439,000 |
| Eastgate Sub | 1 | 0 | $430,000 | $430,000 |
| Winter Park Estates Sec 5 | 1 | 0 | $429,900 | $429,900 |
| New England Bldg | 1 | 0 | $425,000 | $425,000 |
| Ridge High 1St Add | 1 | 0 | $419,990 | $419,990 |
| Albert Lee Ridge | 1 | 0 | $415,000 | $415,000 |
| Lake Bell Terrace | 1 | 0 | $410,000 | $410,000 |
| Wrenwood Unit 3 4Th Add | 1 | 0 | $399,900 | $399,900 |
| Justamere Camp Rep | 1 | 0 | $395,000 | $395,000 |
| Winter Park Estates | 1 | 0 | $380,000 | $380,000 |
| Glencoe | 1 | 0 | $375,000 | $375,000 |
| Glencoe Sub | 1 | 0 | $369,900 | $369,900 |
| Cranes Creek | 1 | 0 | $365,000 | $365,000 |
| Virginia Heights Condo | 1 | 0 | $359,000 | $359,000 |
| Tanglewood Sec 3 Rep | 1 | 0 | $355,000 | $355,000 |
| Winter Park Gardens Condo | 1 | 0 | $350,000 | $350,000 |
| Village Condos | 1 | 0 | $349,500 | $349,500 |
| Olympia Heights | 1 | 0 | $340,000 | $340,000 |
| Via Lago/Hanging Moss Condo | 1 | 0 | $335,000 | $335,000 |
| Eastbrook Subd Unit No 05 | 1 | 0 | $334,000 | $334,000 |
| Winter Park Pointe 02 Ph 01 | 1 | 0 | $319,000 | $319,000 |
| Cranes Crk | 1 | 0 | $309,900 | $309,900 |
| Windward Square Sec 3 | 1 | 0 | $305,000 | $305,000 |
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 Winter Park?
What do homes $300K–$500K cost in Winter Park?
Which Winter Park community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Winter Park
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- Winter Park homes under $300K
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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 Winter Park, 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.