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Oldsmar Homes For Sale & Real Estate - 177 homes

Oldsmar homes for sale are located in Pinellas County, Florida. Find homes in Oldsmar for sale with data from the Multiple Listing Service (MLS). Our REALTORS® can assist you in your real estate search for Oldsmar houses.

Location: Oldsmar

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  • 380 WELLINGTON AVE, OLDSMAR, FL 34677

    $1,155,000368 Days on yellowkey   MLS ID: TB8373443

    For Sale TB8373443 - 380 WELLINGTON AVE, OLDSMAR, FL 34677 42 photos

    Bed: 4   Bath: 3.5   Gar: 4
    Liv Area Sq Ft: 3420
       Built: 1992   Tax: $6,112 (2024)
    Community: Country Club Add To Oldsmar Rev
    Single Family


    Estimated Monthly Payment: $6,838 (change assumption)
    Mortgage ($6,329) + Taxes in 2024 ($509)


    Taxes:$6,112

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677

    $246,00053 Days on yellowkey   MLS ID: TB8478422

    For Sale TB8478422 - 388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677 33 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1105
       Built: 1997
    Monthly Fee: $433
       Tax: $1,771 (2025)
    Community: Countryside Key
    Townhouse


    Estimated Monthly Payment: $1,929 (change assumption)
    Mortgage ($1,348) + Fees ($433) + Taxes in 2025 ($148)


    Taxes:$1,771

    Elementary School: Curlew Creek Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 316 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $339,00062 Days on yellowkey   MLS ID: TB8475078

    REDUCED by $10,000 (2.9%) on 03/31/2026

    For Sale TB8475078 - 316 COUNTRY CLUB DR, OLDSMAR, FL 34677 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1344
       Built: 1960   Tax: $562 (2025)
    Community: Oldsmar Country Club Estates Sec 3
    Single Family


    Estimated Monthly Payment: $1,904 (change assumption)
    Mortgage ($1,857) + Taxes in 2025 ($47)


    Taxes:$562

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1806 FOREST DR, OLDSMAR, FL 34677

    $418,000166 Days on yellowkey   MLS ID: TB8442794

    For Sale TB8442794 - 1806 FOREST DR, OLDSMAR, FL 34677 24 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1475
       Built: 1973   Tax: $4,086 (2024)
    Community: Harbor Palms
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,290) + Taxes in 2024 ($340)


    Taxes:$4,086

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 115 WINDWARD PL #15, OLDSMAR, FL 34677

    $180,00017 Days on yellowkey   MLS ID: TB8490824

    For Sale TB8490824 - 115 WINDWARD PL #15, OLDSMAR, FL 34677 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 879
       Built: 1984
    Monthly Fee: $431
       Tax: $2,768 (2025)
    Community: Meadows Condo At East Lake Woodlands
    Condo


    Estimated Monthly Payment: $1,648 (change assumption)
    Mortgage ($986) + Fees ($431) + Taxes in 2025 ($231)


    Taxes:$2,768

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 408 LAKEVIEW DR, OLDSMAR, FL 34677

    $499,90053 Days on yellowkey   MLS ID: TB8478309

    For Sale TB8478309 - 408 LAKEVIEW DR, OLDSMAR, FL 34677 45 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1598
       Built: 1983
    Monthly Fee: $35
       Tax: $3,714 (2025)
    Community: Manors Of Forest Lakes The
    Single Family


    Estimated Monthly Payment: $3,084 (change assumption)
    Mortgage ($2,739) + Fees ($35) + Taxes in 2025 ($310)


    Taxes:$3,714

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 303 MARTHA LN #303, OLDSMAR, FL 34677

    $189,90031 Days on yellowkey   MLS ID: TB8485863

    For Sale TB8485863 - 303 MARTHA LN #303, OLDSMAR, FL 34677 32 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1094
       Built: 1979   Tax: $613 (2025)
    Community: East Lake Woodlands Condo
    Condo


    Estimated Monthly Payment: $1,092 (change assumption)
    Mortgage ($1,041) + Taxes in 2025 ($51)


    Taxes:$613

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 3073 DUANE AVE, OLDSMAR, FL 34677

    $459,000239 Days on yellowkey   MLS ID: TB8417476

    For Sale TB8417476 - 3073 DUANE AVE, OLDSMAR, FL 34677 43 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 2122
       Built: 1973   Tax: $1,936 (2024)
    Community: West Oldsmar Sec 1
    Single Family


    Estimated Monthly Payment: $2,676 (change assumption)
    Mortgage ($2,515) + Taxes in 2024 ($161)


    Taxes:$1,936

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 382 ROSALIND LN, OLDSMAR, FL 34677

    $822,000269 Days on yellowkey   MLS ID: TB8408993

    For Sale TB8408993 - 382 ROSALIND LN, OLDSMAR, FL 34677 75 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3273
       Built: 2001
    Monthly Fee: $100
       Tax: $8,003 (2024)
    Community: Bay Arbor
    Single Family


    Estimated Monthly Payment: $5,271 (change assumption)
    Mortgage ($4,504) + Fees ($100) + Taxes in 2024 ($667)


    Taxes:$8,003

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1764 OAK POND CT, OLDSMAR, FL 34677

    $550,00028 Days on yellowkey   MLS ID: TB8487110

    0 Days Off yellowkey (back on 3/29/2026)

    For Sale TB8487110 - 1764 OAK POND CT, OLDSMAR, FL 34677 39 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2000
       Built: 2000
    Monthly Fee: $13
       Tax: $7,494 (2025)
    Community: Eastlake Oaks Ph 4
    Single Family


    Estimated Monthly Payment: $3,651 (change assumption)
    Mortgage ($3,014) + Fees ($13) + Taxes in 2025 ($625)


    Taxes:$7,494

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1821 DRIFTWOOD CIR N, OLDSMAR, FL 34677

    $395,00076 Days on yellowkey   MLS ID: TB8469044

    2 Days Off yellowkey (back on 2/23/2026)

    For Sale TB8469044 - 1821 DRIFTWOOD CIR N, OLDSMAR, FL 34677 68 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 2034
       Built: 1972   Tax: $1,582 (2024)
    Community: Harbor Palms-Unit Two
    Single Family


    Estimated Monthly Payment: $2,296 (change assumption)
    Mortgage ($2,164) + Taxes in 2024 ($132)


    Taxes:$1,582

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 908 VINEYARD LN, OLDSMAR, FL 34677

    $385,00041 Days on yellowkey   MLS ID: TB8481839

    For Sale TB8481839 - 908 VINEYARD LN, OLDSMAR, FL 34677 36 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1773
       Built: 2017
    Monthly Fee: $418
       Tax: $4,090 (2025)
    Community: Tuscany Woods Preserve
    Townhouse


    Estimated Monthly Payment: $2,868 (change assumption)
    Mortgage ($2,110) + Fees ($418) + Taxes in 2025 ($341)


    Taxes:$4,090

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4738 PEBBLE BROOK DR, OLDSMAR, FL 34677

    $549,00099 Days on yellowkey   MLS ID: TB8460875

    For Sale TB8460875 - 4738 PEBBLE BROOK DR, OLDSMAR, FL 34677 40 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1938
       Built: 1996
    Monthly Fee: $470
       Tax: $4,041 (2025)
    Community: Cross Creek - Unit Two
    Single Family


    Estimated Monthly Payment: $3,815 (change assumption)
    Mortgage ($3,008) + Fees ($470) + Taxes in 2025 ($337)


    Taxes:$4,041

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2270 CHRISTY LN, OLDSMAR, FL 34677

    $1,250,00055 Days on yellowkey   MLS ID: TB8477474

    For Sale TB8477474 - 2270 CHRISTY LN, OLDSMAR, FL 34677 62 photos

    Bed: 4   Bath: 4.5
    Liv Area Sq Ft: 3993
       Built: 1996
    Monthly Fee: $181
       Tax: $11,849 (2025)
    Community: Turtle Creek Unit-Three
    Single Family


    Estimated Monthly Payment: $8,018 (change assumption)
    Mortgage ($6,849) + Fees ($181) + Taxes in 2025 ($987)


    Taxes:$11,849

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2151 DIAMOND CT, OLDSMAR, FL 34677

    $1,389,000169 Days on yellowkey   MLS ID: TB8440175

    For Sale TB8440175 - 2151 DIAMOND CT, OLDSMAR, FL 34677 88 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 3850
       Built: 1998
    Monthly Fee: $142
       Tax: $9,378 (2024)
    Community: Diamond Crest
    Single Family


    Estimated Monthly Payment: $8,534 (change assumption)
    Mortgage ($7,611) + Fees ($142) + Taxes in 2024 ($782)


    Taxes:$9,378

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 201 DUNKIRK RD, OLDSMAR, FL 34677

    $399,00031 Days on yellowkey   MLS ID: TB8486754

    For Sale TB8486754 - 201 DUNKIRK RD, OLDSMAR, FL 34677 23 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1760
       Built: 1959   Tax: $3,373 (2025)
    Community: Oldsmar Country Club Estates Sec 1 Rep
    Single Family


    Estimated Monthly Payment: $2,467 (change assumption)
    Mortgage ($2,186) + Taxes in 2025 ($281)


    Taxes:$3,373

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 209 HEMINGWAY DR, OLDSMAR, FL 34677

    $294,90039 Days on yellowkey   MLS ID: TB8483445

    For Sale TB8483445 - 209 HEMINGWAY DR, OLDSMAR, FL 34677 18 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1086
       Built: 1997
    Monthly Fee: $240
       Tax: $672 (2024)
    Community: Sun Ketch Twnhms At Cypress Lakes
    Townhouse


    Estimated Monthly Payment: $1,912 (change assumption)
    Mortgage ($1,616) + Fees ($240) + Taxes in 2024 ($56)


    Taxes:$672

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 107 MARY DR #107, OLDSMAR, FL 34677

    $189,00095 Days on yellowkey   MLS ID: TB8462887

    For Sale TB8462887 - 107 MARY DR #107, OLDSMAR, FL 34677 86 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1094
       Built: 1981   Tax: $3,445 (2025)
    Community: East Lake Woodlands Condo
    Condo


    Estimated Monthly Payment: $1,323 (change assumption)
    Mortgage ($1,036) + Taxes in 2025 ($287)


    Taxes:$3,445

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 278 PELICAN DR N, OLDSMAR, FL 34677

    $179,999131 Days on yellowkey   MLS ID: TB8453637

    For Sale TB8453637 - 278 PELICAN DR N, OLDSMAR, FL 34677 27 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1128
       Built: 1985
    Monthly Fee: $60
       Tax: $2,239 (2024)
    Community: Gull-Aire Village
    Manufactured Home


    Estimated Monthly Payment: $1,233 (change assumption)
    Mortgage ($986) + Fees ($60) + Taxes in 2024 ($187)


    Taxes:$2,239

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1730 OAK POND CT, OLDSMAR, FL 34677

    $584,00060 Days on yellowkey   MLS ID: TB8476142

    1 Days Off yellowkey (back on 3/29/2026)

    For Sale TB8476142 - 1730 OAK POND CT, OLDSMAR, FL 34677 41 photos

    Bed: 3   Bath: 2.5
    Liv Area Sq Ft: 1918
       Built: 1998
    Monthly Fee: $13
       Tax: $7,594 (2025)
    Community: Eastlake Oaks
    Single Family


    Estimated Monthly Payment: $3,846 (change assumption)
    Mortgage ($3,200) + Fees ($13) + Taxes in 2025 ($633)


    Taxes:$7,594

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN




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Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.