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Oldsmar Single Family Homes For Sale - 98 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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  • 1471 BRIARGROVE WAY, OLDSMAR, FL 34677

    $899,99930 Days on yellowkey   MLS ID: TB8488174

    REDUCED by $19,001 (2.1%) on 04/13/2026

    For Sale TB8488174 - 1471 BRIARGROVE WAY, OLDSMAR, FL 34677 100 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3140
       Built: 1991
    Monthly Fee: $243
       Tax: $9,749 (2025)
    Community: Aberdeen Unit Two
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,987 (change assumption)
    Mortgage ($4,931) + Fees ($243) + Taxes in 2025 ($812)


    Taxes:$9,749

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 2159 WARWICK DR, OLDSMAR, FL 34677

    $800,00037 Days on yellowkey   MLS ID: TB8486224

    For Sale TB8486224 - 2159 WARWICK DR, OLDSMAR, FL 34677 56 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2673
       Built: 1996
    Monthly Fee: $133
       Tax: $6,682 (2025)
    Community: Warwick Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,073 (change assumption)
    Mortgage ($4,383) + Fees ($133) + Taxes in 2025 ($557)


    Taxes:$6,682

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 204 BENGAL CIR, OLDSMAR, FL 34677

    $735,00044 Days on yellowkey   MLS ID: O6388593

    REDUCED by $15,000 (2.0%) on 04/16/2026

    For Sale O6388593 - 204 BENGAL CIR, OLDSMAR, FL 34677 34 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2429
       Built: 2013
    Monthly Fee: $65
       Tax: $5,728 (2025)
    Community: Bungalow Bay Estates
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,570 (change assumption)
    Mortgage ($4,027) + Fees ($65) + Taxes in 2025 ($477)


    Taxes:$5,728

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1404 EAST LAKE WOODLANDS PKWY, OLDSMAR, FL 34677

    $1,225,0004 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


  • 634 TIMBER BAY CIRCLE W, OLDSMAR, FL 34677

    $324,90026 Days on yellowkey   MLS ID: TB8489706

    REDUCED by $4,100 (1.2%) on 04/04/2026

    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: $2,137 (change assumption)
    Mortgage ($1,780) + 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


  • 800 SAINT PETERSBURG DR W, OLDSMAR, FL 34677

    $409,00029 Days on yellowkey   MLS ID: TB8489139

    REDUCED by $10,000 (2.4%) on 04/06/2026

    For Sale TB8489139 - 800 SAINT PETERSBURG DR W, OLDSMAR, FL 34677 20 photos

    Bed: 4   Bath: 3.0
    Liv Area Sq Ft: 1712
       Built: 1949   Tax: $3,631 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $2,544 (change assumption)
    Mortgage ($2,241) + Taxes in 2025 ($303)


    Taxes:$3,631

    Elementary School: Oakhurst Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 2328 WARWICK DR, OLDSMAR, FL 34677

    $854,000240 Days on yellowkey   MLS ID: TB8419306

    REDUCED by $20,000 (2.3%) on 04/13/2026

    For Sale TB8419306 - 2328 WARWICK DR, OLDSMAR, FL 34677 68 photos

    Bed: 4   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 3294
       Built: 1995
    Monthly Fee: $127
       Tax: $5,742 (2024)
    Community: Warwick Hills
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,285 (change assumption)
    Mortgage ($4,679) + Fees ($127) + Taxes in 2024 ($478)


    Taxes:$5,742

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 316 SHORE DR E, OLDSMAR, FL 34677

    $1,469,999275 Days on yellowkey   MLS ID: TB8408673

    0 Days Off yellowkey (back on 4/19/2026)

    For Sale TB8408673 - 316 SHORE DR E, OLDSMAR, FL 34677 34 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 2496
       Built: 1975   Tax: $17,562 (2024)
    Community: Country Club Add To Oldsmar Rev
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $9,518 (change assumption)
    Mortgage ($8,055) + Taxes in 2024 ($1,464)


    Taxes:$17,562

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1744 MAPLELEAF BLVD, OLDSMAR, FL 34677

    $625,00044 Days on yellowkey   MLS ID: W7883065

    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: $3,817 (change assumption)
    Mortgage ($3,425) + 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


  • 1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677

    $849,00086 Days on yellowkey   MLS ID: TB8467569

    REDUCED by $30,000 (3.4%) on 04/07/2026

    For Sale TB8467569 - 1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677 47 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2650
       Built: 1992
    Monthly Fee: $207
       Tax: $11,111 (2024)
    Community: Greenhaven Unit Three
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,785 (change assumption)
    Mortgage ($4,652) + Fees ($207) + Taxes in 2024 ($926)


    Taxes:$11,111

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 50 WILLOWOOD LN, OLDSMAR, FL 34677

    $1,499,90065 Days on yellowkey   MLS ID: TB8475420

    For Sale TB8475420 - 50 WILLOWOOD LN, OLDSMAR, FL 34677 84 photos

    Bed: 5   Bath: 3.5   Gar: 3
    Liv Area Sq Ft: 4172
       Built: 1987
    Monthly Fee: $240
       Tax: $8,709 (2024)
    Community: Deerpath Unit One
    Single Family


    Estimated Monthly Payment: $9,184 (change assumption)
    Mortgage ($8,218) + Fees ($240) + Taxes in 2024 ($726)


    Taxes:$8,709

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 35 GREENHAVEN TRL, OLDSMAR, FL 34677

    $789,90043 Days on yellowkey   MLS ID: TB8484093

    0 Days Off yellowkey (back on 4/11/2026)

    For Sale TB8484093 - 35 GREENHAVEN TRL, OLDSMAR, FL 34677 60 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 3098
       Built: 1988
    Monthly Fee: $182
       Tax: $6,658 (2025)
    Community: Greenhaven Unit Two
    Single Family


    Estimated Monthly Payment: $5,065 (change assumption)
    Mortgage ($4,328) + Fees ($182) + Taxes in 2025 ($555)


    Taxes:$6,658

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 509 CYPRESS VIEW DR, OLDSMAR, FL 34677

    $649,0001 Day on yellowkey   MLS ID: TB8496854

    For Sale TB8496854 - 509 CYPRESS VIEW DR, OLDSMAR, FL 34677 36 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: $4,105 (change assumption)
    Mortgage ($3,556) + Fees ($140) + Taxes in 2025 ($409)


    Taxes:$4,902

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 219 BAY ARBOR BLVD, OLDSMAR, FL 34677

    $560,0001 Day on yellowkey   MLS ID: TB8498550

    For Sale TB8498550 - 219 BAY ARBOR BLVD, OLDSMAR, FL 34677 45 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 1873
       Built: 2000
    Monthly Fee: $100
       Tax: $7,973 (2025)
    Community: Bay Arbor Unit 1A
    Single Family


    Estimated Monthly Payment: $3,833 (change assumption)
    Mortgage ($3,068) + Fees ($100) + Taxes in 2025 ($664)


    Taxes:$7,973

    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

    $499,90058 Days on yellowkey   MLS ID: TB8478309

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

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1598
       Built: 1983
    Monthly Fee: $35
       Tax: $3,714 (2025)
    Community: Manors Of Forest Lakes The
    Spa: Yes

    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


  • 100 KILSYTHE ST, OLDSMAR, FL 34677

    $450,0008 Days on yellowkey   MLS ID: TB8496212

    For Sale TB8496212 - 100 KILSYTHE ST, OLDSMAR, FL 34677 48 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1100
       Built: 1986   Tax: $5,670 (2025)
    Community: Country Club Add To Oldsmar Rev
    Single Family


    Estimated Monthly Payment: $2,938 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($472)


    Taxes:$5,670

    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

    $378,000191 Days on yellowkey   MLS ID: TB8436254

    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: $2,296 (change assumption)
    Mortgage ($2,071) + 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


  • 4858 AUGUSTA AVE, OLDSMAR, FL 34677

    $679,90023 Days on yellowkey   MLS ID: TB8489820

    0 Days Off yellowkey (back on 4/17/2026)

    REDUCED by $10,000 (1.4%) on 04/14/2026

    For Sale TB8489820 - 4858 AUGUSTA AVE, OLDSMAR, FL 34677 20 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2500
       Built: 1996
    Monthly Fee: $151
       Tax: $4,097 (2024)
    Community: East Lake Woodlands Worthington
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,218 (change assumption)
    Mortgage ($3,725) + Fees ($151) + Taxes in 2024 ($341)


    Taxes:$4,097

    Elementary School: None

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1502 WOODSTREAM DR, OLDSMAR, FL 34677

    $689,000202 Days on yellowkey   MLS ID: TB8428089

    2 Days Off yellowkey (back on 4/17/2026)

    For Sale TB8428089 - 1502 WOODSTREAM DR, OLDSMAR, FL 34677 47 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2234
       Built: 1996
    Monthly Fee: $470
       Tax: $5,116 (2024)
    Community: Cross Creek - Unit Two
    Single Family


    Estimated Monthly Payment: $4,672 (change assumption)
    Mortgage ($3,775) + Fees ($470) + Taxes in 2024 ($426)


    Taxes:$5,116

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 1705 IRONWOOD CT E, OLDSMAR, FL 34677

    $330,00037 Days on yellowkey   MLS ID: TB8486052

    REDUCED by $5,000 (1.5%) on 04/02/2026

    For Sale TB8486052 - 1705 IRONWOOD CT E, OLDSMAR, FL 34677 28 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1206
       Built: 1973   Tax: $1,600 (2025)
    Community: Harbor Palms-Unit Six
    Single Family


    Estimated Monthly Payment: $1,942 (change assumption)
    Mortgage ($1,808) + Taxes in 2025 ($133)


    Taxes:$1,600

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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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.