181 total properties
Did you mean the neighborhood Oldsmar?
View 416 COUNTRY CLUB DRIVE Oldsmar, FL MLS# TB8475710
$385,000
3

Beds

2.0

Baths

1,293

Sq.Ft.

416 COUNTRY CLUB DRIVE

Oldsmar, FL

View 108 BRENT CIRCLE Oldsmar, FL MLS# TB8483935
  • Virtual Tour
1 of 30
$384,000
3

Beds

3.0

Baths

1,834

Sq.Ft.

108 BRENT CIRCLE

Oldsmar, FL

View 1505 SUNSET WIND LOOP Oldsmar, FL MLS# W7883526
$380,000
3

Beds

2.1

Baths

1,667

Sq.Ft.

1505 SUNSET WIND LOOP

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM HARBOR
The time to sell is now! THE TIME TO SELL IS NOW!
View 370 S WOODLANDS DRIVE Oldsmar, FL MLS# TB8361268
$379,999
2

Beds

2.0

Baths

1,500

Sq.Ft.

370 S WOODLANDS DRIVE

Oldsmar, FL

Courtesy of 27NORTH REALTY
View 271 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8426952
  • Virtual Tour
1 of 31
$365,000
3

Beds

2.1

Baths

1,452

Sq.Ft.

271 HEMINGWAY DRIVE

Oldsmar, FL

View 3087 DUANE AVENUE Oldsmar, FL MLS# TB8527948
  • Virtual Tour
1 of 30
$365,000
3

Beds

2.0

Baths

1,296

Sq.Ft.

3087 DUANE AVENUE

Oldsmar, FL

Courtesy of AMERICAN HERITAGE REALTY, INC.
View 1909 CASTLE BAY COURT Oldsmar, FL MLS# TB8535099
  • Recently Listed with Virtual Tour
1 of 53
$365,000
3

Beds

2.0

Baths

1,410

Sq.Ft.

1909 CASTLE BAY COURT

Oldsmar, FL

View 2009 PEPPERTREE COURT Oldsmar, FL MLS# O6403164
    1 of 74
    OPEN HOUSE: Saturday 8/22 11:30 AM - 1:00 PM
    $364,999
    3

    Beds

    2.0

    Baths

    1,233

    Sq.Ft.

    2009 PEPPERTREE COURT

    Oldsmar, FL

    View 1811 DRIFTWOOD CIRCLE S Oldsmar, FL MLS# TB8488580
    $359,900
    3

    Beds

    2.0

    Baths

    1,248

    Sq.Ft.

    1811 DRIFTWOOD CIRCLE S

    Oldsmar, FL

    Courtesy of CHARLES RUTENBERG REALTY INC
    View 1504 MERLOT COURT Oldsmar, FL MLS# TB8532311
    • Virtual Tour
    1 of 55
    $355,000
    3

    Beds

    2.1

    Baths

    1,525

    Sq.Ft.

    1504 MERLOT COURT

    Oldsmar, FL

    View 415 COUNTRY CLUB DRIVE Oldsmar, FL MLS# TB8517638
    $350,000
    4

    Beds

    2.0

    Baths

    1,748

    Sq.Ft.

    415 COUNTRY CLUB DRIVE

    Oldsmar, FL

    View 1916 HUDSON COURT Oldsmar, FL MLS# TB8528046
    • Recently Listed with Virtual Tour
    1 of 26
    $350,000
    3

    Beds

    2.0

    Baths

    1,333

    Sq.Ft.

    1916 HUDSON COURT

    Oldsmar, FL

    Courtesy of MARK SPAIN REAL ESTATE
    View 442 EVERGREEN DRIVE Oldsmar, FL MLS# TB8517079
    • Virtual Tour
    1 of 44
    $349,900
    3

    Beds

    2.0

    Baths

    1,190

    Sq.Ft.

    442 EVERGREEN DRIVE

    Oldsmar, FL

    Courtesy of EXP REALTY LLC
    View 415 MAPLEWOOD CIRCLE Oldsmar, FL MLS# TB8539039
    • Recently Listed with Virtual Tour
    1 of 44
    $349,900
    3

    Beds

    1.0

    Baths

    1,583

    Sq.Ft.

    415 MAPLEWOOD CIRCLE

    Oldsmar, FL

    View 206 BEDFORD STREET Oldsmar, FL MLS# TB8455925
    • Virtual Tour
    1 of 54
    $349,700
    3

    Beds

    2.0

    Baths

    1,274

    Sq.Ft.

    206 BEDFORD STREET

    Oldsmar, FL

    View 103 CUTLASS WAY Oldsmar, FL MLS# TB8479354
    • Virtual Tour
    1 of 20
    $345,000
    3

    Beds

    2.1

    Baths

    1,392

    Sq.Ft.

    103 CUTLASS WAY

    Oldsmar, FL

    Courtesy of FLORIDA COMMERCIAL GROUP
    View 611 TANGERINE DRIVE Oldsmar, FL MLS# TB8513141
    • Virtual Tour
    1 of 37
    $345,000
    3

    Beds

    2.0

    Baths

    1,382

    Sq.Ft.

    611 TANGERINE DRIVE

    Oldsmar, FL

    Courtesy of AMERICAN HERITAGE REALTY, INC.
    View 208 CUTLASS WAY Oldsmar, FL MLS# TB8501214
    • Virtual Tour
    1 of 54
    $340,000
    3

    Beds

    2.1

    Baths

    1,392

    Sq.Ft.

    208 CUTLASS WAY

    Oldsmar, FL

    Courtesy of DALTON WADE INC
    View 606 CABERNET WAY Oldsmar, FL MLS# TB8512784
    • Virtual Tour
    1 of 53
    $339,900
    3

    Beds

    2.1

    Baths

    1,525

    Sq.Ft.

    606 CABERNET WAY

    Oldsmar, FL

    Courtesy of THE SOMERDAY GROUP PL
    View 602 BAY LAKE TRAIL Oldsmar, FL MLS# TB8503595
    $335,000
    3

    Beds

    2.0

    Baths

    1,554

    Sq.Ft.

    602 BAY LAKE TRAIL

    Oldsmar, FL

    About Oldsmar

    The Oldsmar area enjoys the distinction of offering the county’s only contiguous land connection to the City of Tampa and Hillsborough County.  Perhaps this “no bridges” location has helped to foster the area’s rapid growth in lovely residential communities. Local attractions include the thoroughbred horse racing at Tampa Bay Downs Race Track, the bargains at Oldsmar Flea Market, and the skating rink at the Tampa Bay Skating Academy.  Housing ranges from spacious single-family homes to executive homes and estates or stately older residences in the heart of town.  The regional Upper Tampa Bay Chamber of Commerce headquartered in Oldsmar also covers the unincorporated communities of Town and Country and Northwest Hillsborough.

    Listings in Oldsmar, FL

    203

    Estimated median home price

    $335,000
    Oldsmar FL Homes for Sale & Properties

    Weichert Realtors is one of the nation's leading providers of Oldsmar, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Oldsmar, FL.

    Homes for Sale by Price in Oldsmar, FL

    PriceCount
    $0 - 100K1
    $100K - 200K48
    $200K - 300K41
    $300K - 400K39
    $400K - 500K23
    $500K - 600K18
    $600K - 700K8
    $700K - 800K5
    $800K - 900K4
    $900K - 1M1
    $1M - Max15

    Homes for Sale by Type in Oldsmar, FL

    Property TypeCount
    Single Family106
    Townhouse22
    Condo46
    Commercial3
    Rental51
    Lots and Land7
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home19
    Farms0

    (Data as of 8/21/2026)

    Information deemed reliable but not guaranteed.

    The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the Daytona Board of Realtors, and includes listings held by other brokerage firms. Detailed information about Real Estate listings held by brokerage firms (licensees) other than Weichert Realtors include the name of the listing brokers.

    The information being provided is for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

    Data is updated as of 8/21/2026.

    Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

    Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

    Data is updated as of 8/21/2026.