Homes for Sale $300K to $500K in Fleming Island, FL
This page tracks every Fleming Island 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.
69 homes listed between $300,000 and $500,000 are for sale or pending in Fleming Island, FL today across 34 communities. The median asking price is $390,000, from $312,000 to $499,900. Listings in Fleming Island without that feature have a median of $569,950. Most listings right now: Eagle Harbor (12), Not Validd (7), Pace Island (5). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Fleming Island: the listings
38 active listings match today (36% of Fleming Island inventory), median asking $369,945, $204/sq ft, median 71 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Fleming Island
The most expensive $300k–$500k homes in Fleming Island
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 2140 Blue Heron Cove Drive | $489,900 | 2,331 | Admirals Inlet |
| 2283 Lookout Landing | $489,900 | 2,282 | Eagle Harbor |
| 2299 S Brook Drive | $485,000 | 2,855 | Eagle Harbor |
| 461 Pine Eagle Drive | $485,000 | 2,612 | Pine Eagle Estates |
| 144 Oakwood Plantation Drive | $480,000 | 2,275 | Oakwood Plantation |
| 1844 Chatham Village Drive | $469,000 | 2,753 | Chatham Village |
| 2277 Eagle Perch Place | $450,000 | 1,859 | Eagle Perch |
| 461 Wynfield Circle | $439,000 | 2,111 | Wynfield |
| 1537 Winston Lane | $425,000 | 1,904 | Fleming Island Plantation |
| 327 Scenic Point Lane | $424,999 | 2,314 | The Point |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 38 | 100% |
Fleming Island 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 |
|---|---|---|---|---|
| Eagle Harbor | 12 | 0 | $454,900 | $315,000 |
| Not Validd | 7 | 7 | $350,990 | $319,990 |
| Pace Island | 5 | 0 | $424,900 | $312,000 |
| Fleming Island Estat | 5 | 2 | $329,900 | $315,000 |
| Fleming Island | 4 | 2 | $374,945 | $364,990 |
| Island Forest | 4 | 0 | $327,450 | $325,000 |
| Oakwood Plantation | 2 | 0 | $482,500 | $480,000 |
| Wynfield | 2 | 0 | $427,000 | $415,000 |
| Fleming Island Plantation | 2 | 0 | $419,950 | $399,900 |
| Hollywood Forest | 1 | 0 | $499,900 | $499,900 |
| Admirals Inlet | 1 | 0 | $489,900 | $489,900 |
| Pine Eagle Estates | 1 | 0 | $485,000 | $485,000 |
| Chatham Village | 1 | 0 | $469,000 | $469,000 |
| Fairway Village | 1 | 0 | $460,000 | $460,000 |
| Eagle Perch | 1 | 0 | $450,000 | $450,000 |
| Harvest Bend | 1 | 0 | $449,990 | $449,990 |
| Walnut Creek | 1 | 0 | $428,000 | $428,000 |
| The Point | 1 | 0 | $424,999 | $424,999 |
| Hibernia Oaks | 1 | 0 | $420,000 | $420,000 |
| Creighton Landing | 1 | 0 | $415,000 | $415,000 |
| Fleming Oaks | 1 | 0 | $415,000 | $415,000 |
| Peters Creek South | 1 | 0 | $400,000 | $400,000 |
| Brighton | 1 | 0 | $400,000 | $400,000 |
| Pine Court | 1 | 0 | $398,000 | $398,000 |
| Cypress Glen | 1 | 0 | $385,000 | $385,000 |
| Fleming Brook | 1 | 0 | $379,000 | $379,000 |
| Bay Harbor | 1 | 0 | $369,900 | $369,900 |
| Brookstone | 1 | 0 | $369,000 | $369,000 |
| Pine Island | 1 | 0 | $359,900 | $359,900 |
| Majestic Oaks | 1 | 0 | $339,900 | $339,900 |
| Hawks Landing | 1 | 0 | $329,000 | $329,000 |
| Woodlands | 1 | 0 | $315,000 | $315,000 |
| The Enclave | 1 | 0 | $315,000 | $315,000 |
| Stone Creek | 1 | 0 | $312,500 | $312,500 |
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 Fleming Island?
What do homes $300K–$500K cost in Fleming Island?
Which Fleming Island community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
Keep exploring Fleming Island
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Live data: realMLS, refreshed with every MLS pull; this page rebuilds on every ship. Community-level aggregates only: active and pending residential listings in Fleming Island, 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.