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Oldsmar Single Family Homes For Sale - 97 homes

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

Location: Oldsmar

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  • 140 ASHLEY LN, OLDSMAR, FL 34677

    $309,90035 Days on yellowkey   MLS ID: TB8504188

    1 Days Off yellowkey (back on 5/22/2026)

    For Sale TB8504188 - 140 ASHLEY LN, OLDSMAR, FL 34677 41 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1460
       Built: 1981
    Monthly Fee: $440
       Tax: $1,408 (2025)
    Community: East Lake Woodlands Cluster Homes
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,255 (change assumption)
    Mortgage ($1,698) + Fees ($440) + Taxes in 2025 ($117)


    Taxes:$1,408

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 208 CUTLASS WAY, OLDSMAR, FL 34677

    $350,00043 Days on yellowkey   MLS ID: TB8501214

    REDUCED by $20,000 (5.4%) on 04/29/2026

    For Sale TB8501214 - 208 CUTLASS WAY, OLDSMAR, FL 34677 54 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1392
       Built: 2015
    Monthly Fee: $285
       Tax: $3,417 (2025)
    Community: Hayes Park Village
    Single Family


    Estimated Monthly Payment: $2,488 (change assumption)
    Mortgage ($1,918) + Fees ($285) + Taxes in 2025 ($285)


    Taxes:$3,417

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 506 SHORE DR E, OLDSMAR, FL 34677

    $900,00019 Days on yellowkey   MLS ID: TB8509618

    For Sale TB8509618 - 506 SHORE DR E, OLDSMAR, FL 34677 31 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1313
       Built: 1955   Tax: $9,895 (2025)
    Community: Tampashores Bay Sec
    Single Family


    Estimated Monthly Payment: $5,756 (change assumption)
    Mortgage ($4,931) + Taxes in 2025 ($825)


    Taxes:$9,895

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1534 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677

    $1,249,00020 Days on yellowkey   MLS ID: TB8509589

    1 Days Off yellowkey (back on 5/20/2026)

    For Sale TB8509589 - 1534 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677 64 photos

    Bed: 4   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3402
       Built: 1994
    Monthly Fee: $200
       Tax: $7,125 (2024)
    Community: Greenhaven Unit-Four
    Single Family


    Estimated Monthly Payment: $7,637 (change assumption)
    Mortgage ($6,844) + Fees ($200) + Taxes in 2024 ($594)


    Taxes:$7,125

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 511 BUCKINGHAM AVE E, OLDSMAR, FL 34677

    $1,300,00023 Days on yellowkey   MLS ID: TB8507804

    2 Days Off yellowkey (back on 5/20/2026)

    For Sale TB8507804 - 511 BUCKINGHAM AVE E, OLDSMAR, FL 34677 77 photos

    Bed: 5   Bath: 4.5   Gar: 2
    Liv Area Sq Ft: 3436
       Built: 2026   Tax: $1,427 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $7,242 (change assumption)
    Mortgage ($7,123) + Taxes in 2025 ($119)


    Taxes:$1,427

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 545 LAKE CYPRESS CIR, OLDSMAR, FL 34677

    $485,90093 Days on yellowkey   MLS ID: TB8482985

    0 Days Off yellowkey (back on 5/19/2026)

    REDUCED by $9,100 (1.8%) on 04/15/2026

    For Sale TB8482985 - 545 LAKE CYPRESS CIR, OLDSMAR, FL 34677 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1694
       Built: 2000
    Monthly Fee: $140
       Tax: $6,865 (2025)
    Community: Preserve At Cypress Lakes Ph Ii The
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,374 (change assumption)
    Mortgage ($2,662) + Fees ($140) + Taxes in 2025 ($572)


    Taxes:$6,865

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 848 CHRISTINA CIR, OLDSMAR, FL 34677

    $560,00021 Days on yellowkey   MLS ID: TB8509369

    0 Days Off yellowkey (back on 5/19/2026)

    For Sale TB8509369 - 848 CHRISTINA CIR, OLDSMAR, FL 34677 39 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1756
       Built: 1994
    Monthly Fee: $68
       Tax: $4,544 (2025)
    Community: Bay's End
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,515 (change assumption)
    Mortgage ($3,068) + Fees ($68) + Taxes in 2025 ($379)


    Taxes:$4,544

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 2009 PEPPERTREE CT, OLDSMAR, FL 34677

    $390,00038 Days on yellowkey   MLS ID: O6403164

    For Sale O6403164 - 2009 PEPPERTREE CT, OLDSMAR, FL 34677 70 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1233
       Built: 1981   Tax: $927 (2025)
    Community: Bayside Meadows Ph Ii
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $2,214 (change assumption)
    Mortgage ($2,137) + Taxes in 2025 ($77)


    Taxes:$927

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 551 SALMON CT, OLDSMAR, FL 34677

    $349,90036 Days on yellowkey   MLS ID: TB8502478

    For Sale TB8502478 - 551 SALMON CT, OLDSMAR, FL 34677 54 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1344
       Built: 2002
    Monthly Fee: $70
       Tax: $175 (2025)
    Community: Gull-Aire Village Ph 2C
    Single Family


    Estimated Monthly Payment: $2,002 (change assumption)
    Mortgage ($1,917) + Fees ($70) + Taxes in 2025 ($15)


    Taxes:$175

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1909 CASTLE BAY CT, OLDSMAR, FL 34677

    $370,000239 Days on yellowkey   MLS ID: TB8436254

    REDUCED by $4,000 (1.1%) on 05/19/2026

    For Sale TB8436254 - 1909 CASTLE BAY CT, OLDSMAR, FL 34677 52 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1410
       Built: 1984   Tax: $2,696 (2024)
    Community: Sheffield Village Ph Ii At Bayside Meadows
    Single Family


    Estimated Monthly Payment: $2,252 (change assumption)
    Mortgage ($2,027) + Taxes in 2024 ($225)


    Taxes:$2,696

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1654 BAYHILL DR, OLDSMAR, FL 34677

    $570,000234 Days on yellowkey   MLS ID: TB8438417

    0 Days Off yellowkey (back on 5/18/2026)

    For Sale TB8438417 - 1654 BAYHILL DR, OLDSMAR, FL 34677 62 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2320
       Built: 1995
    Monthly Fee: $199
       Tax: $5,855 (2024)
    Community: Creekside
    Single Family


    Estimated Monthly Payment: $3,810 (change assumption)
    Mortgage ($3,123) + Fees ($199) + Taxes in 2024 ($488)


    Taxes:$5,855

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 311 VISTA CRUISER LN, OLDSMAR, FL 34677

    $350,000194 Days on yellowkey   MLS ID: TB8450597

    REDUCED by $5,000 (1.4%) on 04/28/2026

    For Sale TB8450597 - 311 VISTA CRUISER LN, OLDSMAR, FL 34677 50 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 1547
       Built: 2015
    Monthly Fee: $248
       Tax: $3,551 (2024)
    Community: Hayes Park Village
    Single Family


    Estimated Monthly Payment: $2,462 (change assumption)
    Mortgage ($1,918) + Fees ($248) + Taxes in 2024 ($296)


    Taxes:$3,551

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1795 BAYHILL DR, OLDSMAR, FL 34677

    $539,90054 Days on yellowkey   MLS ID: TB8476650

    FORECLOSURE TB8476650 - 1795 BAYHILL DR, OLDSMAR, FL 34677 58 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1844
       Built: 1994
    Monthly Fee: $199
       Tax: $8,406 (2025)
    Community: Creekside
    Single Family


    Estimated Monthly Payment: $3,858 (change assumption)
    Mortgage ($2,958) + Fees ($199) + Taxes in 2025 ($701)


    Taxes:$8,406

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 317 SHORE DR E, OLDSMAR, FL 34677

    $484,700128 Days on yellowkey   MLS ID: FC315737

    REDUCED by $4,970 (1.0%) on 04/21/2026

    For Sale FC315737 - 317 SHORE DR E, OLDSMAR, FL 34677 42 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1660
       Built: 2000   Tax: $6,929 (2024)
    Community: Country Club Add To Oldsmar Rev
    Single Family


    Estimated Monthly Payment: $3,233 (change assumption)
    Mortgage ($2,656) + Taxes in 2024 ($577)


    Taxes:$6,929

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 324 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $385,000405 Days on yellowkey   MLS ID: TB8379269

    For Sale TB8379269 - 324 COUNTRY CLUB DR, OLDSMAR, FL 34677 46 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1288
       Built: 1960   Tax: $3,828 (2024)
    Community: Oldsmar Country Club Estates Sec 3
    Single Family


    Estimated Monthly Payment: $2,429 (change assumption)
    Mortgage ($2,110) + Taxes in 2024 ($319)


    Taxes:$3,828

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 432 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $475,00096 Days on yellowkey   MLS ID: A4684573

    For Sale A4684573 - 432 COUNTRY CLUB DR, OLDSMAR, FL 34677 40 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1936
       Built: 1960   Tax: $3,551 (2025)
    Community: Oldsmar Country Club Estates Sec 2 Blk 3, Lot 6
    Single Family


    Estimated Monthly Payment: $2,899 (change assumption)
    Mortgage ($2,603) + Taxes in 2025 ($296)


    Taxes:$3,551

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 509 CYPRESS VIEW DR, OLDSMAR, FL 34677

    $624,90049 Days on yellowkey   MLS ID: TB8496854

    3 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $9,100 (1.4%) on 05/06/2026

    For Sale TB8496854 - 509 CYPRESS VIEW DR, OLDSMAR, FL 34677 52 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2084
       Built: 1998
    Monthly Fee: $140
       Tax: $4,902 (2025)
    Community: Preserve At Cypress Lakes Ph I The
    Single Family


    Estimated Monthly Payment: $3,973 (change assumption)
    Mortgage ($3,424) + Fees ($140) + Taxes in 2025 ($409)


    Taxes:$4,902

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 2151 DIAMOND CT, OLDSMAR, FL 34677

    $1,350,000222 Days on yellowkey   MLS ID: TB8440175

    REDUCED by $39,000 (2.8%) on 04/21/2026

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

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3850
       Built: 1998
    Monthly Fee: $142
       Tax: $9,378 (2024)
    Community: Diamond Crest
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $8,321 (change assumption)
    Mortgage ($7,397) + 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


  • 1744 MAPLELEAF BLVD, OLDSMAR, FL 34677

    $610,00092 Days on yellowkey   MLS ID: W7883065

    0 Days Off yellowkey (back on 5/12/2026)

    REDUCED by $15,000 (2.4%) on 04/20/2026

    For Sale W7883065 - 1744 MAPLELEAF BLVD, OLDSMAR, FL 34677 82 photos

    Bed: 6   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3124
       Built: 2000
    Monthly Fee: $12
       Tax: $4,563 (2025)
    Community: Eastlake Oaks Ph 4
    Spa: No

    Single Family


    Estimated Monthly Payment: $3,735 (change assumption)
    Mortgage ($3,342) + Fees ($12) + Taxes in 2025 ($380)


    Taxes:$4,563

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 435 LAKEVIEW DR, OLDSMAR, FL 34677

    $475,00072 Days on yellowkey   MLS ID: TB8489554

    REDUCED by $14,000 (2.9%) on 05/12/2026

    For Sale TB8489554 - 435 LAKEVIEW DR, OLDSMAR, FL 34677 44 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1570
       Built: 1984
    Monthly Fee: $35
       Tax: $6,675 (2025)
    Community: Manors Of Forest Lakes The
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $3,194 (change assumption)
    Mortgage ($2,603) + Fees ($35) + Taxes in 2025 ($556)


    Taxes:$6,675

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




Why Bother Searching Elsewhere for Oldsmar Single Family Homes for Sale?

Oldsmar home, townhome, and condo, villa, and other listing sale data is continuously updated on yellowkeyrealty.com. yellowkeyrealty.com offers one of the most exhaustive, current, and relevant set of data you can find on single family homes for sale in Oldsmar . You can use our website to view Multiple Listing Service (MLS) data on Oldsmar single family homes. Feel free to reach out to a REALTOR ® at 1-954-369-1486 if you are unable to find specific information on any of our Oldsmar single family home listings.



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.