204 total properties
Did you mean the neighborhood Oldsmar?
View 4969 KILKENNEY WAY Oldsmar, FL MLS# TB8438530
    1 of 92
    OPEN HOUSE: Saturday 12/13 1:00 PM - 4:00 PM
    $799,900
    4

    Beds

    3.0

    Baths

    2,809

    Sq.Ft.

    4969 KILKENNEY WAY

    Oldsmar, FL

    Courtesy of RE/MAX REALTEC GROUP INC
    View 380 ROSALIND LANE Oldsmar, FL MLS# TB8437475
    $659,900
    3

    Beds

    2.1

    Baths

    2,423

    Sq.Ft.

    380 ROSALIND LANE

    Oldsmar, FL

    Courtesy of FDI REALTY
    View 505 OAKWOOD BOULEVARD Oldsmar, FL MLS# TB8432340
    $449,000
    4

    Beds

    2.0

    Baths

    1,993

    Sq.Ft.

    505 OAKWOOD BOULEVARD

    Oldsmar, FL

    Courtesy of CHARLES RUTENBERG REALTY INC
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 281 CYPRESS LANE #281 Oldsmar, FL MLS# TB8435538
    $207,500
    2

    Beds

    2.0

    Baths

    1,054

    Sq.Ft.

    281 CYPRESS LANE #281

    Oldsmar, FL

    Courtesy of UNITED REAL ESTATE SUNCOAST
    View 1909 CASTLE BAY COURT Oldsmar, FL MLS# TB8436254
    • Virtual Tour
    1 of 52
    OPEN HOUSE: Saturday 12/13 3:00 PM - 6:00 PM
    $390,000
    3

    Beds

    2.0

    Baths

    1,410

    Sq.Ft.

    1909 CASTLE BAY COURT

    Oldsmar, FL

    Courtesy of KELLER WILLIAMS REALTY- PALM H
    View 350 HOLLY HILL ROAD Oldsmar, FL MLS# TB8432259
    • Virtual Tour
    1 of 57
    $669,000
    4

    Beds

    2.0

    Baths

    2,510

    Sq.Ft.

    350 HOLLY HILL ROAD

    Oldsmar, FL

    Courtesy of COASTAL PROPERTIES GROUP INTERNATIONAL
    View 1758 OAK POND COURT Oldsmar, FL MLS# TB8435691
    • Virtual Tour
    1 of 36
    $750,000
    6

    Beds

    3.0

    Baths

    2,867

    Sq.Ft.

    1758 OAK POND COURT

    Oldsmar, FL

    Courtesy of FUTURE HOME REALTY INC
    View 4007 PALM KEY AVENUE Oldsmar, FL MLS# TB8435073
    $669,000
    4

    Beds

    3.0

    Baths

    2,587

    Sq.Ft.

    4007 PALM KEY AVENUE

    Oldsmar, FL

    Courtesy of CHARLES RUTENBERG REALTY INC
    View 5163 PINNACLE DRIVE Oldsmar, FL MLS# TB8435206
    • Virtual Tour
    1 of 55
    $619,700
    3

    Beds

    2.0

    Baths

    1,886

    Sq.Ft.

    5163 PINNACLE DRIVE

    Oldsmar, FL

    Courtesy of RE/MAX REALTEC GROUP INC
    View 1744 MAPLELEAF BLVD Oldsmar, FL MLS# TB8434852
    • Virtual Tour
    1 of 23
    $625,000
    6

    Beds

    3.0

    Baths

    3,124

    Sq.Ft.

    1744 MAPLELEAF BLVD

    Oldsmar, FL

    Courtesy of FIRST IN REAL ESTATE SERVICES
    View 2044 SHEFFIELD COURT Oldsmar, FL MLS# TB8327277
    $190,000
    2

    Beds

    2.0

    Baths

    1,296

    Sq.Ft.

    2044 SHEFFIELD COURT

    Oldsmar, FL

    Courtesy of BHHS FLORIDA PROPERTIES GROUP
    View 315 WOODS LANDING TRAIL Oldsmar, FL MLS# TB8433357
    $319,900
    2

    Beds

    2.1

    Baths

    1,200

    Sq.Ft.

    315 WOODS LANDING TRAIL

    Oldsmar, FL

    Courtesy of MIHARA & ASSOCIATES INC.
    View 300 DOUGLAS ROAD W Oldsmar, FL MLS# TB8434164
    $415,000
    Studio

    Beds

    0.0

    Baths

    300 DOUGLAS ROAD W

    Oldsmar, FL

    Courtesy of LPT REALTY, LLC
    View 646 TIMBER BAY CIRCLE W Oldsmar, FL MLS# W7879421
    $409,000
    3

    Beds

    2.0

    Baths

    1,554

    Sq.Ft.

    646 TIMBER BAY CIRCLE W

    Oldsmar, FL

    Courtesy of RE/MAX CHAMPIONS
    View 4886 WESTCHESTER COURT Oldsmar, FL MLS# TB8427987
    • Virtual Tour
    1 of 39
    OPEN HOUSE: Sunday 12/14 12:00 PM - 2:30 PM
    $569,000
    3

    Beds

    2.0

    Baths

    1,920

    Sq.Ft.

    4886 WESTCHESTER COURT

    Oldsmar, FL

    Courtesy of COLDWELL BANKER REALTY
    View 260 BALSAM DRIVE Oldsmar, FL MLS# TB8433742
    • Virtual Tour
    1 of 25
    $289,900
    2

    Beds

    2.0

    Baths

    1,250

    Sq.Ft.

    260 BALSAM DRIVE

    Oldsmar, FL

    Courtesy of MARC JOSEPH REALTY, INC
    View 2159 WARWICK DRIVE Oldsmar, FL MLS# TB8366755
    • Virtual Tour
    1 of 58
    OPEN HOUSE: Sunday 12/14 12:00 PM - 2:00 PM
    $835,000
    4

    Beds

    3.0

    Baths

    2,673

    Sq.Ft.

    2159 WARWICK DRIVE

    Oldsmar, FL

    Courtesy of PALERMO REAL ESTATE PROF. INC.
    View 190 WATER OAK WAY Oldsmar, FL MLS# TB8427990
    • Virtual Tour
    1 of 48
    $725,000
    3

    Beds

    2.1

    Baths

    2,061

    Sq.Ft.

    190 WATER OAK WAY

    Oldsmar, FL

    Courtesy of FUTURE HOME REALTY INC
    View 604 KINGSMILL COURT Oldsmar, FL MLS# TB8430567
    • Virtual Tour
    1 of 72
    $475,000
    3

    Beds

    2.0

    Baths

    1,757

    Sq.Ft.

    604 KINGSMILL COURT

    Oldsmar, FL

    Courtesy of KELLER WILLIAMS REALTY- PALM H
    View 2007 PALM KEY AVENUE Oldsmar, FL MLS# TB8430845
    $479,900
    3

    Beds

    2.1

    Baths

    1,888

    Sq.Ft.

    2007 PALM KEY AVENUE

    Oldsmar, FL

    Courtesy of BHHS FLORIDA PROPERTIES GROUP

    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

    226

    Estimated median home price

    $367,450
    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 - 100K0
    $100K - 200K36
    $200K - 300K51
    $300K - 400K42
    $400K - 500K28
    $500K - 600K16
    $600K - 700K14
    $700K - 800K11
    $800K - 900K6
    $900K - 1M2
    $1M - Max20

    Homes for Sale by Type in Oldsmar, FL

    Property TypeCount
    Single Family116
    Townhouse30
    Condo41
    Commercial6
    Rental61
    Lots and Land12
    Condo/Town/CoOp0
    CoOp0
    Multi Family1
    Mobile Home20
    Farms0

    (Data as of 12/12/2025)

    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 12/12/2025.