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Homes Under $300K in Oldsmar, FL
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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 75 Listings
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Homes Under $300K in Oldsmar, FL

24 of 75 Listings

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Thomas O'Leary

Realty.com

Lic. #BK3453168

Call Thomas
  1. 112 Cypress Ct #112 — photo13Active

    $149,900

    2 bd · 2 ba · 1,054 sqft

    112 Cypress Ct #112, Oldsmar, FL

    Wil Sanders · EXP REALTY LLC

  2. 392 Cobia Way — photo32Active

    $178,000

    2 bd · 2 ba · 1,344 sqft

    392 Cobia Way, Oldsmar, FL

    Anne Hode · AH REALTY SERVICES, LLC

  3. 145 Poole Pl — photo34Active

    $235,000

    2 bd · 2 ba · 1,380 sqft

    145 Poole Pl, Oldsmar, FL

    Giselle Rachels · SOUTH CEDAR REAL ESTATE, INC

  4. 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

  5. 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

  6. 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

  7. 131 Woodlake Wynde — photo42Active

    $159,500

    2 bd · 2 ba · 924 sqft

    131 Woodlake Wynde, Oldsmar, FL

    Rebecca Norton · COLDWELL BANKER REALTY

  8. 210 Woodlake Wynde — photo28Active

    $177,000

    2 bd · 2 ba · 888 sqft

    210 Woodlake Wynde, Oldsmar, FL

    Paul DeSantis, PA · PREMIER SOTHEBYS INTL REALTY

  9. 2031 Dover Ct — photoPrice ReducedOpen house Sun, Oct 18 · 1:00 PM19Active

    $220,000

    2 bd · 2 ba · 1,215 sqft

    2031 Dover Ct, Oldsmar, FL

    Vivian Clifton · LOKATION

  10. 389 Tranquil Ct — photo50Active

    $179,000

    2 bd · 2 ba · 1,032 sqft

    389 Tranquil Ct, Oldsmar, FL

    Jayne Phoenix · BHHS FLORIDA PROPERTIES GROUP

  11. 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

  12. 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

  13. 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

  14. 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

  15. 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

  16. 428 Pelican Dr S — photo56Active

    $249,000

    2 bd · 2 ba · 1,671 sqft

    428 Pelican Dr S, Oldsmar, FL

    Cyndi Olmstead · CONCI, REALTORS

  17. 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

  18. 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

  19. 135 Pinewinds Blvd — photo49Active

    $239,900

    2 bd · 2 ba · 1,053 sqft

    135 Pinewinds Blvd, Oldsmar, FL

    Holly Iannucci, LLC · LA ROSA REALTY BEACHES LLC

  20. 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

  21. 317 Woodlake Wynde — photo22Active

    $197,500

    2 bd · 2 ba · 924 sqft

    317 Woodlake Wynde, Oldsmar, FL

    Robert Paolini · EXP REALTY LLC

  22. 56 Pelican Dr S — photoPrice Reduced61Active

    $182,900

    2 bd · 2 ba · 1,196 sqft

    56 Pelican Dr S, Oldsmar, FL

    Jada Maynard · MAYNARD PROPERTY GROUP LLC

  23. 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

  24. 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

12…4

About Homes Under $300K in Oldsmar, FL

Homes Under $300K in Oldsmar, FL: 75 active listings as of October 18, 2026, 00:33 UTC.

Property types among these 75 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Condominium4053.3%
Manufactured Home1925.3%
Townhouse56.7%

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Listing data & MLS disclosures

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Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Listing information is provided for consumers? personal, non-commercial use, solely to identify prospective properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Information deemed reliable but not guaranteed. Copyright © 2026 MLS GRID. All Rights Reserved.
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    Thomas O'Leary

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    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.