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Oldsmar Single Family Homes For Sale - 100 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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  • 1404 EAST LAKE WOODLANDS PKWY, OLDSMAR, FL 34677

    $1,225,00059 Days on yellowkey   MLS ID: TB8496474

    For Sale TB8496474 - 1404 EAST LAKE WOODLANDS PKWY, OLDSMAR, FL 34677 85 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 4312
       Built: 1990
    Monthly Fee: $207
       Tax: $8,294 (2025)
    Community: Greenhaven Unit Three
    Spa: No

    Single Family


    Estimated Monthly Payment: $7,610 (change assumption)
    Mortgage ($6,712) + Fees ($207) + Taxes in 2025 ($691)


    Taxes:$8,294

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 3858 SHORE BLVD, OLDSMAR, FL 34677

    $1,150,00032 Days on yellowkey   MLS ID: TB8506221

    REDUCED by $50,000 (4.2%) on 06/12/2026

    For Sale TB8506221 - 3858 SHORE BLVD, OLDSMAR, FL 34677 78 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1594
       Built: 1986   Tax: $8,857 (2025)
    Community: West Oldsmar Sec 1
    Single Family


    Estimated Monthly Payment: $7,039 (change assumption)
    Mortgage ($6,301) + Taxes in 2025 ($738)


    Taxes:$8,857

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 364 VENTURA DR, OLDSMAR, FL 34677

    $599,9003 Days on yellowkey   MLS ID: TB8517197

    For Sale TB8517197 - 364 VENTURA DR, OLDSMAR, FL 34677 62 photos

    Bed: 3   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2237
       Built: 2001
    Monthly Fee: $100
       Tax: $9,325 (2025)
    Community: Bay Arbor
    Single Family


    Estimated Monthly Payment: $4,164 (change assumption)
    Mortgage ($3,287) + Fees ($100) + Taxes in 2025 ($777)


    Taxes:$9,325

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 627 TIMBER BAY CIR W, OLDSMAR, FL 34677

    $329,00015 Days on yellowkey   MLS ID: TB8513485

    INCREASED by $19,000 (6.1%) on 06/12/2026

    For Sale TB8513485 - 627 TIMBER BAY CIR W, OLDSMAR, FL 34677 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1274
       Built: 1984   Tax: $645 (2025)
    Community: Shoreview Ph 2
    Single Family


    Estimated Monthly Payment: $1,856 (change assumption)
    Mortgage ($1,803) + Taxes in 2025 ($54)


    Taxes:$645

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 438 LAFAYETTE BLVD, OLDSMAR, FL 34677

    $584,90099 Days on yellowkey   MLS ID: TB8480797

    REDUCED by $15,000 (2.5%) on 06/10/2026

    For Sale TB8480797 - 438 LAFAYETTE BLVD, OLDSMAR, FL 34677 65 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2138
       Built: 1988   Tax: $8,284 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $3,895 (change assumption)
    Mortgage ($3,205) + Taxes in 2025 ($690)


    Taxes:$8,284

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: None


  • 604 LIMETREE DR, OLDSMAR, FL 34677

    $375,00052 Days on yellowkey   MLS ID: O6401483

    For Sale O6401483 - 604 LIMETREE DR, OLDSMAR, FL 34677 29 photos

    Bed: 3   Bath: 3.0
    Liv Area Sq Ft: 1430
       Built: 1980   Tax: $3,108 (2025)
    Community: Harbor Palms Unit Eleven
    Single Family


    Estimated Monthly Payment: $2,314 (change assumption)
    Mortgage ($2,055) + Taxes in 2025 ($259)


    Taxes:$3,108

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1924 MONTEGO CT, OLDSMAR, FL 34677

    $359,9003 Days on yellowkey   MLS ID: TB8517782

    For Sale TB8517782 - 1924 MONTEGO CT, OLDSMAR, FL 34677 29 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1269
       Built: 1980   Tax: $5,005 (2025)
    Community: Bayside Meadows-Phase I
    Single Family


    Estimated Monthly Payment: $2,389 (change assumption)
    Mortgage ($1,972) + Taxes in 2025 ($417)


    Taxes:$5,005

    Elementary School: Oldsmar Elementary-PN

    High School: None

    Tax Year: 2025

    Middle School: None


  • 368 TAVERNIER CIR, OLDSMAR, FL 34677

    $585,00012 Days on yellowkey   MLS ID: A4694760

    1 Days Off yellowkey (back on 6/11/2026)

    For Sale A4694760 - 368 TAVERNIER CIR, OLDSMAR, FL 34677 40 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1880
       Built: 1997
    Monthly Fee: $75
       Tax: $7,344 (2025)
    Community: Fountains At Cypress Lakes Ii-B The
    Single Family


    Estimated Monthly Payment: $3,892 (change assumption)
    Mortgage ($3,205) + Fees ($75) + Taxes in 2025 ($612)


    Taxes:$7,344

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1758 OAK POND CT, OLDSMAR, FL 34677

    $585,00030 Days on yellowkey   MLS ID: TB8507682

    For Sale TB8507682 - 1758 OAK POND CT, OLDSMAR, FL 34677 57 photos

    Bed: 6   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2867
       Built: 2001
    Monthly Fee: $13
       Tax: $4,224 (2025)
    Community: Eastlake Oaks Ph 4
    Single Family


    Estimated Monthly Payment: $3,570 (change assumption)
    Mortgage ($3,205) + Fees ($13) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 549 LONGWOOD CIR, OLDSMAR, FL 34677

    $515,00038 Days on yellowkey   MLS ID: A4692285

    REDUCED by $10,000 (1.9%) on 06/11/2026

    For Sale A4692285 - 549 LONGWOOD CIR, OLDSMAR, FL 34677 87 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1344
       Built: 1984
    Monthly Fee: $30
       Tax: $5,336 (2025)
    Community: Manors Of Forest Lakes The
    Single Family


    Estimated Monthly Payment: $3,296 (change assumption)
    Mortgage ($2,822) + Fees ($30) + Taxes in 2025 ($445)


    Taxes:$5,336

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 586 KINGSMILL CT, OLDSMAR, FL 34677

    $615,0009 Days on yellowkey   MLS ID: TB8512390

    For Sale TB8512390 - 586 KINGSMILL CT, OLDSMAR, FL 34677 57 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2452
       Built: 1998
    Monthly Fee: $298
       Tax: $10,436 (2025)
    Community: Kingsmill
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,537 (change assumption)
    Mortgage ($3,370) + Fees ($298) + Taxes in 2025 ($870)


    Taxes:$10,436

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 316 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $328,90029 Days on yellowkey   MLS ID: TB8508856

    REDUCED by $100 (0.0%) on 06/11/2026

    For Sale TB8508856 - 316 COUNTRY CLUB DR, OLDSMAR, FL 34677 32 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1344
       Built: 1960   Tax: $616 (2025)
    Community: Oldsmar Country Club Estates Sec 3
    Single Family


    Estimated Monthly Payment: $1,853 (change assumption)
    Mortgage ($1,802) + Taxes in 2025 ($51)


    Taxes:$616

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 355 VENTURA DR, OLDSMAR, FL 34677

    $625,00023 Days on yellowkey   MLS ID: TB8510293

    For Sale TB8510293 - 355 VENTURA DR, OLDSMAR, FL 34677 32 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1938
       Built: 2001
    Monthly Fee: $100
       Tax: $5,919 (2025)
    Community: Bay Arbor
    Single Family


    Estimated Monthly Payment: $4,018 (change assumption)
    Mortgage ($3,425) + Fees ($100) + Taxes in 2025 ($493)


    Taxes:$5,919

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 206 BEDFORD ST, OLDSMAR, FL 34677

    $359,700182 Days on yellowkey   MLS ID: TB8455925

    SHORT SALE TB8455925 - 206 BEDFORD ST, OLDSMAR, FL 34677 51 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1274
       Built: 1988   Tax: $3,766 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $2,285 (change assumption)
    Mortgage ($1,971) + Taxes in 2025 ($314)


    Taxes:$3,766

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 307 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $349,95046 Days on yellowkey   MLS ID: TB8502335

    REDUCED by $27,950 (7.4%) on 05/25/2026

    For Sale TB8502335 - 307 COUNTRY CLUB DR, OLDSMAR, FL 34677 31 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1670
       Built: 1960   Tax: $3,567 (2025)
    Community: Oldsmar Country Club Estates Sec 3
    Single Family


    Estimated Monthly Payment: $2,215 (change assumption)
    Mortgage ($1,917) + Taxes in 2025 ($297)


    Taxes:$3,567

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 634 TIMBER BAY CIRCLE W, OLDSMAR, FL 34677

    $321,50081 Days on yellowkey   MLS ID: TB8489706

    0 Days Off yellowkey (back on 4/30/2026)

    REDUCED by $3,400 (1.0%) on 04/24/2026

    For Sale TB8489706 - 634 TIMBER BAY CIRCLE W, OLDSMAR, FL 34677 27 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1056
       Built: 1985   Tax: $4,283 (2025)
    Community: Shoreview Phase 2 Blk 6, Lot 3
    Single Family


    Estimated Monthly Payment: $2,119 (change assumption)
    Mortgage ($1,762) + Taxes in 2025 ($357)


    Taxes:$4,283

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 415 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $399,0003 Days on yellowkey   MLS ID: TB8517638

    For Sale TB8517638 - 415 COUNTRY CLUB DR, OLDSMAR, FL 34677 22 photos

    Bed: 4   Bath: 2.0
    Liv Area Sq Ft: 1748
       Built: 1959   Tax: $3,505 (2024)
    Community: Oldsmar Country Club Estates Sec 2
    Single Family


    Estimated Monthly Payment: $2,478 (change assumption)
    Mortgage ($2,186) + Taxes in 2024 ($292)


    Taxes:$3,505

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: John Hopkins Middle-PN


  • 629 BAY LAKE TRL, OLDSMAR, FL 34677

    $350,0003 Days on yellowkey   MLS ID: TB8517300

    For Sale TB8517300 - 629 BAY LAKE TRL, OLDSMAR, FL 34677 40 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1338
       Built: 1984   Tax: $4,224 (2025)
    Community: Shoreview Ph 2
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,270 (change assumption)
    Mortgage ($1,918) + Taxes in 2025 ($352)


    Taxes:$4,224

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 347 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $429,000122 Days on yellowkey   MLS ID: TB8475491

    REDUCED by $20,000 (4.5%) on 04/05/2026

    For Sale TB8475491 - 347 COUNTRY CLUB DR, OLDSMAR, FL 34677 80 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1280
       Built: 1967   Tax: $1,515 (2024)
    Community: Oldsmar Country Club Estates Sec 1 Rep
    Single Family


    Estimated Monthly Payment: $2,477 (change assumption)
    Mortgage ($2,351) + Taxes in 2024 ($126)


    Taxes:$1,515

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677

    $370,00085 Days on yellowkey   MLS ID: TB8488580

    REDUCED by $10,000 (2.6%) on 04/23/2026

    For Sale TB8488580 - 1811 DRIFTWOOD CIR S, OLDSMAR, FL 34677 34 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1248
       Built: 1973   Tax: $1,036 (2025)
    Community: Harbor Palms-Unit Two
    Single Family


    Estimated Monthly Payment: $2,114 (change assumption)
    Mortgage ($2,027) + Taxes in 2025 ($86)


    Taxes:$1,036

    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.