Homes for Sale $300K to $500K in Oldsmar, FL
This page tracks every Oldsmar 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.
57 homes listed between $300,000 and $500,000 are for sale or pending in Oldsmar, FL today across 33 communities. The median asking price is $379,999, from $300,000 to $499,000. Listings in Oldsmar without that feature have a median of $239,000. Most listings right now: Seaside Estates (5), Bayside Terrace (5), East Lake Woodlands Cluster Homes (5). Updated October 2, 2026 from the MLS.
Live $300k–$500k homes in Oldsmar: the listings
49 active listings match today (33% of Oldsmar inventory), median asking $385,000, $247/sq ft, median 26 days on market. Photo cards link to the listing; refreshed nightly.
Newest $300k–$500k homes in Oldsmar
The most expensive $300k–$500k homes in Oldsmar
| Listing | Asking | Sq ft | Community |
|---|---|---|---|
| 854 Christina Circle | $499,000 | 2,065 | Bays End |
| 900 Lucas Lane | $495,000 | 1,685 | Hunters Trail Townhomes |
| 311 Country Club Drive | $489,000 | 1,732 | oldsmar country club estates |
| 1103 Mango Court | $489,000 | 2,230 | — |
| 117 Brent Circle | $475,000 | 1,834 | Seaside Estates |
| 317 Shore Drive | $474,700 | 1,660 | — |
| 508 Washington Avenue | $473,900 | 1,507 | west oldsmar |
| 603 Canal Way | $469,900 | 1,754 | Gull Aire Village |
| 129 Brent Circle | $460,000 | 1,834 | Seaside Estates |
| 116 Brent Circle | $450,000 | 1,834 | Seaside Estates |
$300K–$500K Homes by price
| Band | For sale | Share |
|---|---|---|
| $300K–$500K | 49 | 100% |
Oldsmar 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 |
|---|---|---|---|---|
| Seaside Estates | 5 | 0 | $450,000 | $374,000 |
| Bayside Terrace | 5 | 0 | $399,000 | $380,000 |
| East Lake Woodlands Cluster Homes | 5 | 0 | $324,900 | $309,900 |
| Oldsmar Country Club Estates Sec 3 | 4 | 0 | $417,500 | $320,998 |
| Harbor Palms-Unit Two | 3 | 0 | $404,000 | $329,000 |
| Shoreview Ph 2 | 3 | 0 | $312,000 | $310,000 |
| Oldsmar Rev Map | 2 | 0 | $414,800 | $355,700 |
| East Lake Woodlands Patio Homes | 2 | 0 | $384,999 | $379,999 |
| Gull-Aire Village | 2 | 0 | $384,950 | $300,000 |
| Harbor Palms-Unit Five | 2 | 0 | $352,400 | $349,900 |
| Bays End | 1 | 0 | $499,000 | $499,000 |
| Hunters Trail Twnhms | 1 | 0 | $495,000 | $495,000 |
| Country Club Add To Oldsmar Rev | 1 | 0 | $474,700 | $474,700 |
| Tampashores Hotel Plaza Sec | 1 | 0 | $439,000 | $439,000 |
| Manors Of Forest Lakes The Ph 2 | 1 | 0 | $425,000 | $425,000 |
| East Lake Woodlands Pinewinds | 1 | 0 | $425,000 | $425,000 |
| Harbor Palms Unit Eleven | 1 | 0 | $419,900 | $419,900 |
| Gull-Aire Village Ph 2B | 1 | 0 | $419,500 | $419,500 |
| Heatherwood Unit One Condo | 1 | 0 | $397,000 | $397,000 |
| Sun Ketch Twnhms At Cypress Lakes | 1 | 0 | $395,000 | $395,000 |
| Oldsmar Country Club Estates Sec 1 Rep | 1 | 0 | $395,000 | $395,000 |
| Bayside Terrace - Pt Rep | 1 | 0 | $375,000 | $375,000 |
| Oldsmar Galleria Condo | 1 | 0 | $345,000 | $345,000 |
| Harbor Palms-Unit One | 1 | 0 | $344,900 | $344,900 |
| Bayside Meadows-Phase I | 1 | 0 | $340,000 | $340,000 |
| Sheffield Village Ph Ii At Bayside Meadows | 1 | 0 | $335,000 | $335,000 |
| Hayes Park Village | 1 | 0 | $335,000 | $335,000 |
| Gull-Aire Village Ph 2C | 1 | 0 | $332,000 | $332,000 |
| Bayside Meadows Ph Ii | 1 | 0 | $330,000 | $330,000 |
| Tuscany Woods South | 1 | 0 | $330,000 | $330,000 |
| Oldsmar Country Club Estates Sec 2 | 1 | 0 | $324,900 | $324,900 |
| Harbor Palms - Unit Six | 1 | 0 | $319,000 | $319,000 |
| East Lake Woodlans Woods Landing Townhomes | 1 | 0 | $300,000 | $300,000 |
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 Oldsmar?
What do homes $300K–$500K cost in Oldsmar?
Which Oldsmar community has the most homes $300K–$500K for sale?
What is the monthly payment on a $400,000 home?
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Homes $300K–$500K in nearby Pinellas County cities
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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 Oldsmar, 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.