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Homes Under $300K in Oldsmar, FL
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Start here

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3 bedsWith a pool

Homes Under $300K in Oldsmar, FL

Homes Under $300K in Oldsmar, FL

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24 of 73 Listings
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Homes Under $300K in Oldsmar, FL

24 of 73 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 127 Nancy Dr #127 — photo53Active

    $205,000

    2 bd · 2 ba · 1,094 sqft

    127 Nancy Dr #127, Oldsmar, FL

    Charlie Bodine · REAL ESTATE FIRM OF FLORIDA, LLC

  2. 151 Lakeview Way #151 — photo45Active

    $189,000

    2 bd · 2 ba · 1,094 sqft

    151 Lakeview Way #151, Oldsmar, FL

    Kim Adams · RE/MAX ELITE REALTY

  3. 110 Lakeside Ct #110 — photo34Active

    $149,900

    2 bd · 2 ba · 1,094 sqft

    110 Lakeside Ct #110, Oldsmar, FL

    Mark Fazzini · RE/MAX REALTEC GROUP INC

  4. 131 Woodlake Wynde — photo42Active

    $159,500

    2 bd · 2 ba · 924 sqft

    131 Woodlake Wynde, Oldsmar, FL

    Rebecca Norton · COLDWELL BANKER REALTY

  5. 210 Woodlake Wynde — photo28Active

    $177,000

    2 bd · 2 ba · 888 sqft

    210 Woodlake Wynde, Oldsmar, FL

    Paul DeSantis, PA · PREMIER SOTHEBYS INTL REALTY

  6. 2031 Dover Ct — photoOpen house Tue, Oct 13 · 1:00 PM19Active

    $247,500

    2 bd · 2 ba · 1,215 sqft

    2031 Dover Ct, Oldsmar, FL

    Vivian Clifton · LOKATION

  7. 389 Tranquil Ct — photo50Active

    $179,000

    2 bd · 2 ba · 1,032 sqft

    389 Tranquil Ct, Oldsmar, FL

    Jayne Phoenix · BHHS FLORIDA PROPERTIES GROUP

  8. 82 Pelican Dr N — photo45Active

    $179,000

    2 bd · 2 ba · 958 sqft

    82 Pelican Dr N, Oldsmar, FL

    Jayne Phoenix · BHHS FLORIDA PROPERTIES GROUP

  9. 225 Tarpon Lane — photoOpen house Sun, Oct 18 · 11:30 AM36Active

    $169,900

    2 bd · 2 ba · 1,120 sqft

    225 Tarpon Lane, Oldsmar, FL

    Anne Hode · AH REALTY SERVICES, LLC

  10. 129 Camphor Cir #C — photo60Active

    $155,000

    2 bd · 2 ba · 915 sqft

    129 Camphor Cir #C, Oldsmar, FL

    Garrett Grimes · KELLER WILLIAMS REALTY PORTFOLIO COLLECTION

  11. 221 Caryl Way #221 — photoPrice Reduced18Active

    $175,000

    2 bd · 2 ba · 1,094 sqft

    221 Caryl Way #221, Oldsmar, FL

    Joseph Richards · KELLER WILLIAMS TAMPA PROPERTIES

  12. 34 Pelican Dr E — photo40Active

    $209,900

    2 bd · 2 ba · 1,136 sqft

    34 Pelican Dr E, Oldsmar, FL

    Jayne Phoenix · BHHS FLORIDA PROPERTIES GROUP

  13. 428 Pelican Dr S — photo56Active

    $249,000

    2 bd · 2 ba · 1,671 sqft

    428 Pelican Dr S, Oldsmar, FL

    Cyndi Olmstead · CONCI, REALTORS

  14. 340 Canal Way — photoPrice Reduced30Active

    $149,500

    2 bd · 2 ba · 1,056 sqft

    340 Canal Way, Oldsmar, FL

    Paul Radtke · BHHS FLORIDA PROPERTIES GROUP

  15. 128 Nancy Dr — photoPrice Reduced64Active

    $215,000

    2 bd · 2 ba · 1,094 sqft

    128 Nancy Dr, Oldsmar, FL

    Vanessa Leonard · KELLER WILLIAMS REALTY- PALM HARBOR

  16. 105 Lakeside Ct #Elw VI Unit 5 — photo50Active

    $230,000

    2 bd · 2 ba · 1,150 sqft

    105 Lakeside Ct #Elw VI Unit 5, Oldsmar, FL

    Rose Railey · B & K REAL ESTATE & PROPERTY MANAGEMENT PA

  17. 317 Woodlake Wynde — photo22Active

    $197,500

    2 bd · 2 ba · 924 sqft

    317 Woodlake Wynde, Oldsmar, FL

    Robert Paolini · EXP REALTY LLC

  18. 56 Pelican Dr S — photoPrice Reduced61Active

    $184,900

    2 bd · 2 ba · 1,196 sqft

    56 Pelican Dr S, Oldsmar, FL

    Jada Maynard · MAYNARD PROPERTY GROUP LLC

  19. 133 Sabal Ct #F — photoPrice Reduced24Active

    $119,500

    2 bd · 2 ba · 915 sqft

    133 Sabal Ct #F, Oldsmar, FL

    Hope DeVivo · DALTON WADE INC

  20. 215 Woods Landing Trl — photo36Active

    $300,000

    3 bd · 3 ba · 1,450 sqft

    215 Woods Landing Trl, Oldsmar, FL

    David Pratt · CENTURY 21 COASTAL ALLIANCE

  21. 105 Lakeview Way #105 — photoPrice Reduced41Active

    $209,799

    2 bd · 2 ba · 1,094 sqft

    105 Lakeview Way #105, Oldsmar, FL

    Sabrina Westenbarger · CENTURY 21 CIRCLE

  22. 322 Bass Ct — photoPrice Reduced32Active

    $149,000

    2 bd · 2 ba · 1,144 sqft

    322 Bass Ct, Oldsmar, FL

    Michele Strong · ENGEL & VOLKERS BELLEAIR

  23. 279 Countryside Key Blvd — photo45Active

    $275,000

    2 bd · 2 ba · 1,105 sqft

    279 Countryside Key Blvd, Oldsmar, FL

    Charlie Bodine · REAL ESTATE FIRM OF FLORIDA, LLC

  24. 160 Lakeview Way #160 — photoPrice Reduced36Active

    $159,900

    2 bd · 2 ba · 1,094 sqft

    160 Lakeview Way #160, Oldsmar, FL

    Rene Mailaender · RE/MAX REALTEC GROUP INC

12…4

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  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #BK3453168

    Call Thomas

    Oldsmar, FL community profile

    Population
    15,092
    Median income
    $72,414
    Housing units
    6,425
    People per sq. mi.
    1,048.1
    Area
    14.4 sq. mi.

    Source: HJN community data

    Oldsmar housing market

    September 2026 · This period is still settling

    Oldsmar 12-month median sale price trend

    Selling at 98.6% of asking price

    Buyers here are paying below asking. MLS · 29 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 21, 2026

    Median sale price
    $350,000$244,237–$560,950 typical range
    Price per sq. ft.
    $229
    Sales
    27
    Paid in cash
    55.6%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $355,300
    Homes for sale
    152
    Median days on market
    44 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    11.1%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 11, 2026

    Median home size
    1,550 sq. ft.