44 total properties
Did you mean the neighborhood Oldsmar?
View 910 WAVERLY ST AVENUE Oldsmar, FL MLS# A4687818
  • Recently Listed with Virtual Tour
1 of 7
$249,999
Studio

Beds

0.0

Baths

910 WAVERLY ST AVENUE

Oldsmar, FL

Courtesy of NEW ALLIANCE GROUP REALTY
View 208 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8490712
  • Recently Listed with Virtual Tour
1 of 36
OPEN HOUSE: Saturday 3/28 11:30 AM - 2:00 PM
$314,900
2

Beds

2.0

Baths

1,207

Sq.Ft.

208 HEMINGWAY DRIVE

Oldsmar, FL

Courtesy of RE/MAX MARKETING SPECIALISTS
View 634 TIMBER BAY CIRCLE W Oldsmar, FL MLS# TB8489706
  • Recently Listed with Virtual Tour
1 of 27
$329,000
3

Beds

2.0

Baths

1,056

Sq.Ft.

634 TIMBER BAY CIRCLE W

Oldsmar, FL

Courtesy of AMERICAN HERITAGE REALTY, INC.
The time to sell is now! THE TIME TO SELL IS NOW!
View 240 TADS TRAIL Oldsmar, FL MLS# TB8487439
  • Recently Listed with Virtual Tour
1 of 25
OPEN HOUSE: Saturday 3/28 12:00 PM - 2:00 PM
$249,000
2

Beds

2.0

Baths

1,380

Sq.Ft.

240 TADS TRAIL

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY
View 40 SYLVIA PLACE Oldsmar, FL MLS# TB8487410
  • Recently Listed with Virtual Tour
1 of 40
$299,000
3

Beds

2.0

Baths

1,385

Sq.Ft.

40 SYLVIA PLACE

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 1705 IRONWOOD COURT E Oldsmar, FL MLS# TB8486052
  • Recently Listed with Virtual Tour
1 of 28
$335,000
2

Beds

2.0

Baths

1,206

Sq.Ft.

1705 IRONWOOD COURT E

Oldsmar, FL

Courtesy of KELLER WILLIAMS TAMPA PROP.
View 529 JETSTAR LANE Oldsmar, FL MLS# TB8482197
  • Virtual Tour
1 of 24
$274,000
2

Beds

2.1

Baths

1,013

Sq.Ft.

529 JETSTAR LANE

Oldsmar, FL

Courtesy of FUTURE HOME REALTY INC
View 358 LAKE WAY Oldsmar, FL MLS# TB8486181
  • Adult Community with Virtual Tour
1 of 48
$259,900
3

Beds

2.0

Baths

1,296

Sq.Ft.

358 LAKE WAY

Oldsmar, FL

Courtesy of THE SOMERDAY GROUP PL
View 202 ARLINGTON AVENUE E Oldsmar, FL MLS# TB8485006
$300,000
3

Beds

2.0

Baths

1,436

Sq.Ft.

202 ARLINGTON AVENUE E

Oldsmar, FL

Courtesy of MARK SPAIN REAL ESTATE
View 2020 DOVER COURT Oldsmar, FL MLS# TB8486084
  • Recently Listed with Virtual Tour
1 of 32
OPEN HOUSE: Saturday 3/28 12:00 PM - 2:00 PM
$255,000
2

Beds

2.0

Baths

1,143

Sq.Ft.

2020 DOVER COURT

Oldsmar, FL

Courtesy of EXP REALTY
View 1815 DRIFTWOOD CIRCLE S Oldsmar, FL MLS# TB8483505
$285,000
3

Beds

2.0

Baths

1,855

Sq.Ft.

1815 DRIFTWOOD CIRCLE S

Oldsmar, FL

Courtesy of COLDWELL BANKER REALTY
View 209 HEMINGWAY DRIVE Oldsmar, FL MLS# TB8483445
    1 of 18
    OPEN HOUSE: Sunday 3/29 12:00 PM - 2:00 PM
    $294,900
    2

    Beds

    2.0

    Baths

    1,086

    Sq.Ft.

    209 HEMINGWAY DRIVE

    Oldsmar, FL

    Courtesy of SMITH & ASSOCIATES REAL ESTATE
    View 108 DOLPHIN DRIVE E Oldsmar, FL MLS# TB8482185
    • Adult Community with Virtual Tour
    1 of 32
    OPEN HOUSE: Saturday 3/28 12:30 PM - 2:30 PM
    $319,000
    3

    Beds

    2.0

    Baths

    1,372

    Sq.Ft.

    108 DOLPHIN DRIVE E

    Oldsmar, FL

    Courtesy of KELLER WILLIAMS REALTY- PALM H
    View 433 SAILFISH BOULEVARD Oldsmar, FL MLS# TB8481608
    • Adult Community with Virtual Tour
    1 of 46
    $259,000
    2

    Beds

    2.0

    Baths

    960

    Sq.Ft.

    433 SAILFISH BOULEVARD

    Oldsmar, FL

    Courtesy of AH REALTY SERVICES, LLC
    View 388 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8478422
    $256,000
    2

    Beds

    1.1

    Baths

    1,105

    Sq.Ft.

    388 COUNTRYSIDE KEY BOULEVARD

    Oldsmar, FL

    Courtesy of TROPIC SHORES REALTY
    View 40 SHAMROCK WAY 40 Oldsmar, FL MLS# TB8471405
    • Virtual Tour
    1 of 44
    OPEN HOUSE: Saturday 3/28 1:00 PM - 3:00 PM
    $255,000
    2

    Beds

    2.0

    Baths

    1,502

    Sq.Ft.

    40 SHAMROCK WAY 40

    Oldsmar, FL

    Courtesy of EXP REALTY LLC
    View 80 BIRDSONG COURT Oldsmar, FL MLS# TB8477396
    • Virtual Tour
    1 of 35
    $249,000
    2

    Beds

    2.0

    Baths

    1,053

    Sq.Ft.

    80 BIRDSONG COURT

    Oldsmar, FL

    Courtesy of RE/MAX ACTION FIRST OF FLORIDA
    View 428 PELICAN DRIVE S Oldsmar, FL MLS# TB8474552
    • Adult Community with Virtual Tour
    1 of 52
    $249,000
    2

    Beds

    2.0

    Baths

    1,671

    Sq.Ft.

    428 PELICAN DRIVE S

    Oldsmar, FL

    Courtesy of BHHS FLORIDA PROPERTIES GROUP
    View 235 WOODS LANDING TRAIL 235 Oldsmar, FL MLS# TB8474969
    $299,900
    2

    Beds

    2.0

    Baths

    1,201

    Sq.Ft.

    235 WOODS LANDING TRAIL 235

    Oldsmar, FL

    Courtesy of SOUTHERN LIFE REALTY
    View 291 COUNTRYSIDE KEY BOULEVARD Oldsmar, FL MLS# TB8463435
    $265,000
    2

    Beds

    2.1

    Baths

    1,110

    Sq.Ft.

    291 COUNTRYSIDE KEY BOULEVARD

    Oldsmar, FL

    Courtesy of EXP REALTY LLC

    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

    239

    Estimated median home price

    $385,000
    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 - 200K36
    $200K - 300K50
    $300K - 400K44
    $400K - 500K29
    $500K - 600K22
    $600K - 700K13
    $700K - 800K8
    $800K - 900K9
    $900K - 1M4
    $1M - Max23

    Homes for Sale by Type in Oldsmar, FL

    Property TypeCount
    Single Family136
    Townhouse32
    Condo38
    Commercial4
    Rental34
    Lots and Land8
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home20
    Farms0

    (Data as of 3/27/2026)

    Information deemed reliable but not guaranteed.

    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 3/28/2026.