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.
60 homes listed between $300,000 and $500,000 are for sale or pending in Oldsmar, FL today across 34 communities. The median asking price is $379,999, from $300,000 to $495,000. Listings in Oldsmar without that feature have a median of $249,950. Most listings right now: Seaside Estates (5), East Lake Woodlands Cluster Homes (5), Bayside Terrace (4). Updated September 11, 2026 from the MLS.
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 |
| East Lake Woodlands Cluster Homes | 5 | 0 | $349,900 | $309,900 |
| 4 | 0 | $433,500 | $380,000 | |
| Oldsmar Country Club Estates Sec 3 | 3 | 0 | $445,000 | $395,000 |
| Shoreview Ph 2 | 3 | 0 | $320,000 | $310,000 |
| Gull-Aire Village | 3 | 0 | $300,000 | $300,000 |
| Oldsmar Rev Map | 2 | 0 | $422,350 | $355,700 |
| West Oldsmar Sec 1 | 2 | 0 | $407,450 | $365,000 |
| Harbor Palms-Unit One | 2 | 0 | $396,950 | $344,900 |
| Harbor Palms-Unit Two | 2 | 0 | $392,400 | $359,900 |
| East Lake Woodlands Patio Homes | 2 | 0 | $389,949 | $379,999 |
| Heatherwood Unit One Condo | 2 | 0 | $364,450 | $329,900 |
| Oldsmar Country Club Estates Sec 2 | 2 | 0 | $354,950 | $324,900 |
| Hayes Park Village | 2 | 0 | $342,500 | $340,000 |
| Hunters Trail Twnhms | 1 | 0 | $495,000 | $495,000 |
| Fountains At Cypress Lakes Ii-A The | 1 | 0 | $495,000 | $495,000 |
| 1 | 0 | $484,700 | $484,700 | |
| 1 | 0 | $475,000 | $475,000 | |
| 1 | 0 | $439,000 | $439,000 | |
| 1 | 0 | $425,000 | $425,000 | |
| East Lake Woodlands Pinewinds | 1 | 0 | $425,000 | $425,000 |
| 1 | 0 | $419,000 | $419,000 | |
| Oldsmar Country Club Estates Sec 1 | 1 | 0 | $399,000 | $399,000 |
| Sun Ketch Twnhms At Cypress Lakes | 1 | 0 | $395,000 | $395,000 |
| 1 | 0 | $375,000 | $375,000 | |
| Sheffield Village Ph Ii At Bayside Meadows | 1 | 0 | $365,000 | $365,000 |
| Bayside Meadows Ph Ii | 1 | 0 | $355,000 | $355,000 |
| Tuscany Woods Preserve | 1 | 0 | $355,000 | $355,000 |
| Oldsmar Galleria Condo | 1 | 0 | $345,000 | $345,000 |
| Harbor Palms Unit Eleven | 1 | 0 | $339,900 | $339,900 |
| Tuscany Woods South | 1 | 0 | $330,000 | $330,000 |
| Harbor Palms - Unit Six | 1 | 0 | $329,000 | $329,000 |
| Harbor Palms-Unit Six | 1 | 0 | $320,000 | $320,000 |
| 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?
Keep exploring Oldsmar
- All homes for sale in Oldsmar
- Oldsmar pool homes
- Oldsmar waterfront homes
- Oldsmar golf course homes
- Oldsmar gated community homes
- Oldsmar 4-bedroom homes
- Oldsmar homes under $300K
- Homes $300K–$500K in every city
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.