Homes for Sale Under $300K in Oldsmar, FL

This page tracks every Oldsmar listing with an asking price under $300,000, by community, with live counts and asking prices. Prices are asking prices from the MLS, not values, and the list changes with every refresh.

79 homes listed under $300,000 are for sale or pending in Oldsmar, FL today across 26 communities. The median asking price is $195,000, from $110,000 to $299,900. Listings in Oldsmar without that feature have a median of $469,900. Most listings right now: Gull-Aire Village (15), East Lake Woodlands Condo (13), East Lake Woodlands Cypress Estates (8). Updated September 11, 2026 from the MLS.

Oldsmar homes under $300K by community

Click a community for its full guide: prices, HOA reality, insurance posture and the homes for sale.

Community	Homes Under $300K	Median list	From
Gull-Aire Village	15	$198,500	$154,900
East Lake Woodlands Condo	13	$199,900	$149,900
East Lake Woodlands Cypress Estates	8	$184,950	$149,000
Gardens Of Forest Lakes Condo The	7	$125,000	$110,000
East Lake Woodlands Woodlake Run	6	$190,750	$175,000
East Lake Woodlands Cluster Homes	5	$249,900	$220,000
Oldsmar Revised Map	2	$299,900	$299,900
Bayside Meadows Ph Ii	2	$257,400	$214,900
Countryside Key	2	$252,250	$229,500
Sheffield Village At Bayside Meadows	2	$243,450	$242,000
Meadows Condo At East Lake Woodlands	2	$184,000	$180,000
St Andrews Condo	1	$299,900	$299,900
East Lake Woodlands Patio Homes	1	$299,000	$299,000
Bayside Meadows Sec	1	$291,000	$291,000
Quail Forest Cluster Homes	1	$288,000	$288,000
Shoreview Phase 2	1	$280,000	$280,000
Heatherwood Unit One Condo	1	$279,900	$279,900
Oldsmar Rev Map	1	$269,000	$269,000
Harbor Palms-Unit Five	1	$259,900	$259,900
East Lake Woodlands Pinewinds	1	$239,900	$239,900
East Lake Woodlands	1	$189,999	$189,999
Emerald Bay	1	$189,000	$189,000
	1	$179,950	$179,950
Meadows Condo Unit Two At East Lake Woodlands The	1	$179,900	$179,900
East Lake Woodlands Condo Unit 7	1	$175,000	$175,000
Tampashores Bay Sec	1	$158,990	$158,990

What under $300,000 buys and what to check

In this price band the differences between listings are usually age, size and condition rather than location alone, so read each listing’s year built, square footage and property type (a condo or manufactured home and a single-family home can sit at the same price with very different monthly costs). Budget the full monthly number, not the price: taxes, insurance, and HOA or CDD fees are all on each listing page, and our true cost of ownership calculator puts them into one figure. Insurance quotes on older roofs and older electrical can change which of two similar homes is actually cheaper.

Questions to ask about any listing in this band

How old is the roof, and will insurers write it? Is there a four-point inspection on file? What did the seller pay for insurance last year? In a condo, what are the dues, is there a special assessment or milestone inspection pending, and what do the reserves look like? Is the price a recent reduction, and how long has it been listed? A local agent who works the area will know which communities in this band have the fewest surprises at inspection.

Common questions

How many homes listed under $300,000 are for sale in Oldsmar?

As of September 11, 2026, 79 Oldsmar, FL listings whose MLS record reports an asking price under $300,000 are active or pending, across 26 communities. The count updates with every MLS refresh.

What do homes under $300K cost in Oldsmar?

The median asking price today is $195,000, with listings from $110,000 to $299,900. Oldsmar listings without that feature have a median of $469,900.

Which Oldsmar community has the most homes under $300K for sale?

Gull-Aire Village has the most right now (15), followed by East Lake Woodlands Condo (13), East Lake Woodlands Cypress Estates (8), Gardens Of Forest Lakes Condo The (7).

What is the monthly payment on a home under $300,000?

At today’s rates with 20% down, principal and interest on a $300,000 purchase runs in the $1,500–$1,700 a month range before taxes, insurance and any HOA; each listing page shows the property tax and fees for that home, and the true-cost calculator linked above turns them into one monthly number.

Keep exploring Oldsmar

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 under $300,000. Prices are asking prices, not values. Property features and prices only; nothing on this page describes residents. Equal Housing Opportunity.

Listings courtesy of Stellar MLS as distributed by MLS GRID.