199 total properties
Did you mean the neighborhood Oldsmar?
View 50 WILLOWOOD LANE Oldsmar, FL MLS# TB8475420
  • Virtual Tour
1 of 84
$1,499,900
6

Beds

4.1

Baths

4,475

Sq.Ft.

50 WILLOWOOD LANE

Oldsmar, FL

Courtesy of REAL BROKER, LLC
View 205 CHESTNUT STREET Oldsmar, FL MLS# TB8537182
  • Recently Listed with Virtual Tour
1 of 8
$1,499,000
Studio

Beds

0.0

Baths

205 CHESTNUT STREET

Oldsmar, FL

Courtesy of SUNSHINE REALTY COMPANY LLC
View 2151 DIAMOND COURT Oldsmar, FL MLS# TB8440175
  • Virtual Tour
1 of 88
$1,350,000
4

Beds

3.0

Baths

3,850

Sq.Ft.

2151 DIAMOND COURT

Oldsmar, FL

The time to sell is now! THE TIME TO SELL IS NOW!
View 200 LEE STREET Oldsmar, FL MLS# TB8505047
$1,350,000
2

Beds

1.0

Baths

1,250

Sq.Ft.

200 LEE STREET

Oldsmar, FL

View 200 E STATE STREET E Oldsmar, FL MLS# TB8504841
$1,350,000
1,536

Sq.Ft.

200 E STATE STREET E

Oldsmar, FL

View 3684 TAMPA ROAD 101 Oldsmar, FL MLS# TB8452564
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1 of 28
$1,300,000
3,850

Sq.Ft.

3684 TAMPA ROAD 101

Oldsmar, FL

View 375 WELLINGTON AVENUE Oldsmar, FL MLS# TB8492687
$1,280,000
4

Beds

3.0

Baths

2,624

Sq.Ft.

375 WELLINGTON AVENUE

Oldsmar, FL

Courtesy of KELLER WILLIAMS REALTY- PALM HARBOR
View 1404 EAST LAKE WOODLANDS PARKWAY Oldsmar, FL MLS# TB8496474
  • Virtual Tour
1 of 85
OPEN HOUSE: Sunday 8/23 12:00 PM - 3:00 PM
$1,225,000
4

Beds

3.0

Baths

4,312

Sq.Ft.

1404 EAST LAKE WOODLANDS PARKWAY

Oldsmar, FL

View 640 Brooker Creek Blvd 430 Oldsmar, FL MLS# A12030989
$1,200,000
5,680

Sq.Ft.

640 Brooker Creek Blvd 430

Oldsmar, FL

Courtesy of SMITH ASSOCIATES, INC
View 35 GREENHAVEN TRAIL Oldsmar, FL MLS# TB8531583
$1,124,900
4

Beds

3.0

Baths

3,098

Sq.Ft.

35 GREENHAVEN TRAIL

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 3858 SHORE BOULEVARD Oldsmar, FL MLS# TB8506221
$1,100,000
3

Beds

2.0

Baths

1,594

Sq.Ft.

3858 SHORE BOULEVARD

Oldsmar, FL

Courtesy of CHARLES RUTENBERG REALTY INC
View 1319 FORESTEDGE BOULEVARD Oldsmar, FL MLS# TB8517867
$1,100,000
5

Beds

3.1

Baths

3,849

Sq.Ft.

1319 FORESTEDGE BOULEVARD

Oldsmar, FL

Courtesy of RE/MAX REALTEC GROUP INC
View 85 KELLEYS TRAIL Oldsmar, FL MLS# TB8527215
  • Virtual Tour
1 of 84
$1,100,000
5

Beds

3.0

Baths

3,390

Sq.Ft.

85 KELLEYS TRAIL

Oldsmar, FL

View 4931 TURTLE CREEK TRAIL Oldsmar, FL MLS# TB8518188
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1 of 67
OPEN HOUSE: Sunday 8/23 12:00 PM - 3:00 PM
$1,055,000
4

Beds

3.0

Baths

3,189

Sq.Ft.

4931 TURTLE CREEK TRAIL

Oldsmar, FL

View 4995 CAMBERLEY LANE Oldsmar, FL MLS# TB8523334
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1 of 58
$935,000
3

Beds

2.1

Baths

3,410

Sq.Ft.

4995 CAMBERLEY LANE

Oldsmar, FL

View 475 HOLLY HILL ROAD Oldsmar, FL MLS# TB8529182
$899,500
4

Beds

4.0

Baths

3,441

Sq.Ft.

475 HOLLY HILL ROAD

Oldsmar, FL

View 4987 CROSS POINTE DRIVE Oldsmar, FL MLS# TB8536934
$849,900
4

Beds

3.0

Baths

2,631

Sq.Ft.

4987 CROSS POINTE DRIVE

Oldsmar, FL

View 1723 CAPTIVA DRIVE Oldsmar, FL MLS# TB8538123
  • Recently Listed with Virtual Tour
1 of 84
$830,700
4

Beds

3.0

Baths

2,736

Sq.Ft.

1723 CAPTIVA DRIVE

Oldsmar, FL

Courtesy of COASTAL PROPERTIES GROUP INTERNATIONAL
View 2328 WARWICK DRIVE Oldsmar, FL MLS# TB8419306
    1 of 68
    OPEN HOUSE: Sunday 8/23 1:00 PM - 3:00 PM
    $829,000
    4

    Beds

    3.1

    Baths

    3,294

    Sq.Ft.

    2328 WARWICK DRIVE

    Oldsmar, FL

    Courtesy of COASTAL PROPERTIES GROUP INTERNATIONAL
    View 743 WELLINGTON COURT Oldsmar, FL MLS# TB8541470
    • Recently Listed with Virtual Tour
    1 of 47
    $800,000
    4

    Beds

    3.1

    Baths

    3,058

    Sq.Ft.

    743 WELLINGTON COURT

    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

    201

    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 - 200K47
    $200K - 300K41
    $300K - 400K39
    $400K - 500K22
    $500K - 600K18
    $600K - 700K7
    $700K - 800K6
    $800K - 900K4
    $900K - 1M1
    $1M - Max15

    Homes for Sale by Type in Oldsmar, FL

    Property TypeCount
    Single Family105
    Townhouse22
    Condo45
    Commercial3
    Rental54
    Lots and Land7
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home19
    Farms0

    (Data as of 8/23/2026)

    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 8/23/2026.

    The data relating to the real estate for sale on this web site comes in part from the Realtor Association of Greater Miami and the Beaches.

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

    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 8/23/2026.