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Oldsmar Homes For Sale & Real Estate - 207 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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  • 1909 CASTLE BAY CT, OLDSMAR, FL 34677

    $374,000214 Days on yellowkey   MLS ID: TB8436254

    REDUCED by $4,000 (1.1%) on 05/06/2026

    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: $2,274 (change assumption)
    Mortgage ($2,049) + 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


  • 4953 POINTE CIR, OLDSMAR, FL 34677

    $875,00015 Days on yellowkey   MLS ID: TB8502016

    REDUCED by $10,000 (1.1%) on 05/12/2026

    For Sale TB8502016 - 4953 POINTE CIR, OLDSMAR, FL 34677 39 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2513
       Built: 1997
    Monthly Fee: $142
       Tax: $11,677 (2025)
    Community: Cross Pointe
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,909 (change assumption)
    Mortgage ($4,794) + Fees ($142) + Taxes in 2025 ($973)


    Taxes:$11,677

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 208 CYPRESS CT, OLDSMAR, FL 34677

    $159,90088 Days on yellowkey   MLS ID: TB8475945

    For Sale TB8475945 - 208 CYPRESS CT, OLDSMAR, FL 34677 33 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1054
       Built: 1980   Tax: $2,954 (2025)
    Community: East Lake Woodlands Cypress Estates
    Condo


    Estimated Monthly Payment: $1,122 (change assumption)
    Mortgage ($876) + Taxes in 2025 ($246)


    Taxes:$2,954

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 50 WOODLAKE PL, OLDSMAR, FL 34677

    $218,000Listed 05/11/2026 10:04PM   MLS ID: TB8507105

    For Sale TB8507105 - 50 WOODLAKE PL, OLDSMAR, FL 34677 42 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 924
       Built: 1983   Tax: $3,197 (2025)
    Community: East Lake Woodlands Woodlake Run
    Condo


    Estimated Monthly Payment: $1,461 (change assumption)
    Mortgage ($1,194) + Taxes in 2025 ($266)


    Taxes:$3,197

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 40 SYLVIA PL, OLDSMAR, FL 34677

    $294,90050 Days on yellowkey   MLS ID: TB8487410

    REDUCED by $4,100 (1.4%) on 05/11/2026

    For Sale TB8487410 - 40 SYLVIA PL, OLDSMAR, FL 34677 40 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1385
       Built: 1978
    Monthly Fee: $450
       Tax: $5,439 (2025)
    Community: East Lake Woodlands Cluster Homes
    Villa


    Estimated Monthly Payment: $2,519 (change assumption)
    Mortgage ($1,616) + Fees ($450) + Taxes in 2025 ($453)


    Taxes:$5,439

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 120 EVELYN CT, OLDSMAR, FL 34677

    $278,00016 Days on yellowkey   MLS ID: TB8501596

    REDUCED by $11,000 (3.8%) on 05/11/2026

    For Sale TB8501596 - 120 EVELYN CT, OLDSMAR, FL 34677 46 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1450
       Built: 1979
    Monthly Fee: $490
       Tax: $5,156 (2025)
    Community: East Lake Woodlands Cluster Homes
    Villa


    Estimated Monthly Payment: $2,443 (change assumption)
    Mortgage ($1,523) + Fees ($490) + Taxes in 2025 ($430)


    Taxes:$5,156

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 50 WILLOWOOD LN, OLDSMAR, FL 34677

    $1,499,90088 Days on yellowkey   MLS ID: TB8475420

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

    Bed: 5   Bath: 4.5   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


  • 2328 WARWICK DR, OLDSMAR, FL 34677

    $854,000263 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


  • 382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677

    $520,0006 Days on yellowkey   MLS ID: TB8499334

    For Sale TB8499334 - 382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677 28 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1875
       Built: 1995
    Monthly Fee: $95
       Tax: $5,232 (2025)
    Community: Fountains At Cypress Lakes The
    Single Family


    Estimated Monthly Payment: $3,380 (change assumption)
    Mortgage ($2,849) + Fees ($95) + Taxes in 2025 ($436)


    Taxes:$5,232

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 438 LAFAYETTE BLVD, OLDSMAR, FL 34677

    $599,90067 Days on yellowkey   MLS ID: TB8480797

    REDUCED by $25,000 (4.0%) on 04/13/2026

    For Sale TB8480797 - 438 LAFAYETTE BLVD, OLDSMAR, FL 34677 64 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: $3,977 (change assumption)
    Mortgage ($3,287) + Taxes in 2025 ($690)


    Taxes:$8,284

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: None


  • 260 MICHAELS CIR, OLDSMAR, FL 34677

    $280,0003 Days on yellowkey   MLS ID: TB8507054

    For Sale TB8507054 - 260 MICHAELS CIR, OLDSMAR, FL 34677 18 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1385
       Built: 1980
    Monthly Fee: $362
       Tax: $5,013 (2025)
    Community: East Lake Woodlands Cluster Homes
    Villa


    Estimated Monthly Payment: $2,314 (change assumption)
    Mortgage ($1,534) + Fees ($362) + Taxes in 2025 ($418)


    Taxes:$5,013

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: John Hopkins Middle-PN


  • 141 LAKEVIEW WAY #141, OLDSMAR, FL 34677

    $173,90067 Days on yellowkey   MLS ID: TB8483907

    REDUCED by $1,000 (0.6%) on 04/30/2026

    For Sale TB8483907 - 141 LAKEVIEW WAY #141, OLDSMAR, FL 34677 28 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1094
       Built: 1980   Tax: $3,466 (2025)
    Community: East Lake Woodlands
    Spa: No

    Condo


    Estimated Monthly Payment: $1,242 (change assumption)
    Mortgage ($953) + Taxes in 2025 ($289)


    Taxes:$3,466

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 504 FEDERAL ST, OLDSMAR, FL 34677

    $1,180,000218 Days on yellowkey   MLS ID: TB8427180

    REDUCED by $90,000 (7.1%) on 04/25/2026

    For Sale TB8427180 - 504 FEDERAL ST, OLDSMAR, FL 34677 52 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2961
       Built: 2026   Tax: $1,498 (2024)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $6,590 (change assumption)
    Mortgage ($6,466) + Taxes in 2024 ($125)


    Taxes:$1,498

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 2009 PEPPERTREE CT, OLDSMAR, FL 34677

    $390,00013 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


  • 123 DOLPHIN DR S, OLDSMAR, FL 34677

    $259,900181 Days on yellowkey   MLS ID: TB8447450

    For Sale TB8447450 - 123 DOLPHIN DR S, OLDSMAR, FL 34677 21 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1248
       Built: 1984
    Monthly Fee: $60
       Tax: $419 (2025)
    Community: Gull-Aire Village
    Manufactured Home


    Estimated Monthly Payment: $1,519 (change assumption)
    Mortgage ($1,424) + Fees ($60) + Taxes in 2025 ($35)


    Taxes:$419

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 304 WOODLAKE WYNDE #304, OLDSMAR, FL 34677

    $179,90012 Days on yellowkey   MLS ID: TB8498051

    For Sale TB8498051 - 304 WOODLAKE WYNDE #304, OLDSMAR, FL 34677 24 photos

    Bed: 1   Bath: 1.0
    Liv Area Sq Ft: 674
       Built: 1985
    Monthly Fee: $418
       Tax: $2,403 (2025)
    Community: East Lake Woodlands Woodlake Run
    Condo


    Estimated Monthly Payment: $1,604 (change assumption)
    Mortgage ($986) + Fees ($418) + Taxes in 2025 ($200)


    Taxes:$2,403

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 208 HEMINGWAY DR, OLDSMAR, FL 34677

    $305,00047 Days on yellowkey   MLS ID: TB8490712

    REDUCED by $9,900 (3.1%) on 05/09/2026

    For Sale TB8490712 - 208 HEMINGWAY DR, OLDSMAR, FL 34677 36 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1207
       Built: 1997
    Monthly Fee: $265
       Tax: $4,507 (2025)
    Community: Sun Ketch Twnhms At Cypress Lakes
    Villa


    Estimated Monthly Payment: $2,312 (change assumption)
    Mortgage ($1,671) + Fees ($265) + Taxes in 2025 ($376)


    Taxes:$4,507

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 420 CYPRESS VIEW DR, OLDSMAR, FL 34677

    $485,0005 Days on yellowkey   MLS ID: TB8505264

    0 Days Off yellowkey (back on 5/9/2026)

    For Sale TB8505264 - 420 CYPRESS VIEW DR, OLDSMAR, FL 34677 38 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1870
       Built: 1998
    Monthly Fee: $140
       Tax: $4,405 (2025)
    Community: Preserve At Cypress Lakes Ph I The
    Single Family


    Estimated Monthly Payment: $3,165 (change assumption)
    Mortgage ($2,657) + Fees ($140) + Taxes in 2025 ($367)


    Taxes:$4,405

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 160 JAMES CT, OLDSMAR, FL 34677

    $363,90011 Days on yellowkey   MLS ID: TB8503480

    For Sale TB8503480 - 160 JAMES CT, OLDSMAR, FL 34677 59 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1445
       Built: 1981
    Monthly Fee: $451
       Tax: $5,927 (2025)
    Community: Quail Forest Cluster Homes
    Villa


    Estimated Monthly Payment: $2,939 (change assumption)
    Mortgage ($1,994) + Fees ($451) + Taxes in 2025 ($494)


    Taxes:$5,927

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 417 DOLPHIN DR S, OLDSMAR, FL 34677

    $269,00011 Days on yellowkey   MLS ID: TB8504194

    For Sale TB8504194 - 417 DOLPHIN DR S, OLDSMAR, FL 34677 54 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1253
       Built: 1985
    Monthly Fee: $70
       Tax: $3,616 (2025)
    Community: Gull-Aire Village
    Manufactured Home


    Estimated Monthly Payment: $1,845 (change assumption)
    Mortgage ($1,474) + Fees ($70) + Taxes in 2025 ($301)


    Taxes:$3,616

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None




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Oldsmar home, townhome, condo, villa, and other listing sales 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 houses for sale in Oldsmar . You can use our website to view Multiple Listing Service (MLS) data on Oldsmar Real Estate. 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 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.