Homes for Sale $300K to $500K in Wildwood, FL
This page tracks every Wildwood 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.
44 homes listed between $300,000 and $500,000 are for sale or pending in Wildwood, FL today across 16 communities. The median asking price is $334,535, from $303,990 to $499,900. Listings in Wildwood without that feature have a median of $249,990. Most listings right now: Woodland Crossings (8), Triumph South (6), Highfield At Twisted Oaks Ph 2 (5). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Wildwood: the listings
31 active listings match today (22% of Wildwood inventory), median asking $330,000, $171/sq ft, median 42 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Wildwood
The most expensive $300k–$500k homes in Wildwood
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 5430 County Road 125 | $499,900 | 2,076 | — |
| 7175 County Road 213 | $411,000 | 2,133 | — |
| 1161 Timberwood Drive | $385,565 | 2,314 | Woodland Crossings |
| 4691 Cr 118 | $380,000 | 1,464 | — |
| 9285 County Road 125B | $379,900 | 1,987 | — |
| 4678 Cornerstone Road | $379,000 | 2,605 | Triumph South |
| 1155 Timberwood Drive | $369,900 | 2,109 | Woodland Crossings |
| 3537 E C 462 | $369,000 | 1,500 | — |
| 3280 Windswept Way | $358,610 | 1,850 | Highfield At Twisted Oaks |
| 9205 Newmons Place | $357,240 | 2,262 | Highfield At Twisted Oaks |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 31 | 100% |
Wildwood 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 |
|---|---|---|---|---|
| Woodland Crossings | 8 | 8 | $346,680 | $305,465 |
| Triumph South | 6 | 6 | $313,295 | $305,990 |
| Highfield At Twisted Oaks Ph 2 | 5 | 5 | $357,240 | $352,910 |
| Highfield At Twisted Oaks | 5 | 5 | $317,990 | $307,190 |
| Triumph South Ph 1 | 3 | 0 | $372,000 | $315,000 |
| Beaumont Ph 2 & 3 | 3 | 0 | $329,000 | $304,999 |
| Pepper Tree Village | 2 | 0 | $346,250 | $340,000 |
| Beaumont | 2 | 0 | $329,950 | $329,900 |
| Fairways/Rolling Hills 1St Add | 1 | 0 | $499,900 | $499,900 |
| Lake Miona Heights | 1 | 0 | $380,000 | $380,000 |
| Fairways At Rolling Hills | 1 | 0 | $379,900 | $379,900 |
| Fairways/Rolling Hills | 1 | 0 | $349,900 | $349,900 |
| Beaumont Ph 1 | 1 | 0 | $330,000 | $330,000 |
| Meadouvista | 1 | 1 | $319,999 | $319,999 |
| Medouvista | 1 | 1 | $319,999 | $319,999 |
| Tillman Oaks | 1 | 1 | $303,990 | $303,990 |
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 Wildwood?
What do homes $300K–$500K cost in Wildwood?
Which Wildwood community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Wildwood
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Homes $300K–$500K in nearby Sumter County cities
- The Villages homes $300K–$500K (215 for sale)
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- Sumterville homes $300K–$500K (18 for sale)
- Webster homes $300K–$500K (18 for sale)
- Bushnell homes $300K–$500K (12 for sale)
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 Wildwood, 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.