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Oldsmar Single Family Homes For Sale - 101 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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  • 307 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $385,9508 Days on yellowkey   MLS ID: TB8502335

    REDUCED by $13,950 (3.5%) on 05/06/2026

    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: $2,412 (change assumption)
    Mortgage ($2,115) + 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


  • 382 FOUNTAINVIEW CIR, OLDSMAR, FL 34677

    $520,000Listed 05/06/2026 8:33AM   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


  • 1909 CASTLE BAY CT, OLDSMAR, FL 34677

    $374,000208 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


  • 200 LEE ST, OLDSMAR, FL 34677

    $1,450,0001 Day on yellowkey   MLS ID: TB8505047

    For Sale TB8505047 - 200 LEE ST, OLDSMAR, FL 34677 1 photos

    Bed: 2   Bath: 1.0
    Liv Area Sq Ft: 1250
       Built: 1957   Tax: $4,470 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $8,318 (change assumption)
    Mortgage ($7,945) + Taxes in 2025 ($373)


    Taxes:$4,470

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 1654 BAYHILL DR, OLDSMAR, FL 34677

    $570,000203 Days on yellowkey   MLS ID: TB8438417

    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: $177
       Tax: $5,855 (2024)
    Community: Creekside
    Single Family


    Estimated Monthly Payment: $3,788 (change assumption)
    Mortgage ($3,123) + Fees ($177) + 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


  • 1384 FORESTEDGE BLVD, OLDSMAR, FL 34677

    $720,00041 Days on yellowkey   MLS ID: TB8490510

    REDUCED by $30,000 (4.0%) on 05/05/2026

    For Sale TB8490510 - 1384 FORESTEDGE BLVD, OLDSMAR, FL 34677 59 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2814
       Built: 1991
    Monthly Fee: $243
       Tax: $13,366 (2025)
    Community: Aberdeen Unit Two
    Spa: No

    Single Family


    Estimated Monthly Payment: $5,302 (change assumption)
    Mortgage ($3,945) + Fees ($243) + Taxes in 2025 ($1,114)


    Taxes:$13,366

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 140 ASHLEY LN, OLDSMAR, FL 34677

    $309,9004 Days on yellowkey   MLS ID: TB8504188

    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


  • 506 FEDERAL ST, OLDSMAR, FL 34677

    $1,180,000212 Days on yellowkey   MLS ID: TB8434625

    REDUCED by $90,000 (7.1%) on 04/24/2026

    For Sale TB8434625 - 506 FEDERAL ST, OLDSMAR, FL 34677 53 photos

    Bed: 4   Bath: 3.5   Gar: 2
    Liv Area Sq Ft: 2961
       Built: 2025   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


  • 1734 MAPLELEAF BLVD, OLDSMAR, FL 34677

    $515,00035 Days on yellowkey   MLS ID: TB8492116

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

    REDUCED by $10,000 (1.9%) on 04/23/2026

    For Sale TB8492116 - 1734 MAPLELEAF BLVD, OLDSMAR, FL 34677 82 photos

    Bed: 4   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2428
       Built: 2000
    Monthly Fee: $13
       Tax: $4,787 (2025)
    Community: Eastlake Oaks Ph 4
    Single Family


    Estimated Monthly Payment: $3,234 (change assumption)
    Mortgage ($2,822) + Fees ($13) + Taxes in 2025 ($399)


    Taxes:$4,787

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 502 TIMBER BAY CIR E, OLDSMAR, FL 34677

    $419,90092 Days on yellowkey   MLS ID: TB8467897

    3 Days Off yellowkey (back on 4/8/2026)

    For Sale TB8467897 - 502 TIMBER BAY CIR E, OLDSMAR, FL 34677 33 photos

    Bed: 4   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1658
       Built: 1983   Tax: $5,498 (2024)
    Community: Shoreview Ph I
    Single Family


    Estimated Monthly Payment: $2,759 (change assumption)
    Mortgage ($2,301) + Taxes in 2024 ($458)


    Taxes:$5,498

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 103 CUTLASS WAY, OLDSMAR, FL 34677

    $345,00072 Days on yellowkey   MLS ID: TB8479354

    For Sale TB8479354 - 103 CUTLASS WAY, OLDSMAR, FL 34677 20 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1392
       Built: 2016
    Monthly Fee: $255
       Tax: $6,017 (2025)
    Community: Hayes Park Village
    Single Family


    Estimated Monthly Payment: $2,647 (change assumption)
    Mortgage ($1,890) + Fees ($255) + Taxes in 2025 ($501)


    Taxes:$6,017

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 4922 EDGEWATER LN, OLDSMAR, FL 34677

    $594,00030 Days on yellowkey   MLS ID: W7883975

    REDUCED by $5,000 (0.8%) on 05/04/2026

    For Sale W7883975 - 4922 EDGEWATER LN, OLDSMAR, FL 34677 41 photos

    Bed: 3   Bath: 2.5   Gar: 2
    Liv Area Sq Ft: 2390
       Built: 1997
    Monthly Fee: $158
       Tax: $9,841 (2025)
    Community: Worthington
    Single Family


    Estimated Monthly Payment: $4,233 (change assumption)
    Mortgage ($3,255) + Fees ($158) + Taxes in 2025 ($820)


    Taxes:$9,841

    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

    $800,00054 Days on yellowkey   MLS ID: TB8486224

    1 Days Off yellowkey (back on 5/4/2026)

    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


  • 2009 PEPPERTREE CT, OLDSMAR, FL 34677

    $390,0007 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


  • 504 FEDERAL ST, OLDSMAR, FL 34677

    $1,180,000212 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


  • 165 MOBBLY BAY DR, OLDSMAR, FL 34677

    $1,149,900224 Days on yellowkey   MLS ID: TB8430614

    REDUCED by $70,000 (5.7%) on 05/04/2026

    For Sale TB8430614 - 165 MOBBLY BAY DR, OLDSMAR, FL 34677 100 photos

    Bed: 5   Bath: 4.0   Gar: 3
    Liv Area Sq Ft: 3945
       Built: 2012
    Monthly Fee: $183
       Tax: $8,887 (2024)
    Community: Estuary Of Mobbly Bay
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $7,224 (change assumption)
    Mortgage ($6,301) + Fees ($183) + Taxes in 2024 ($741)


    Taxes:$8,887

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 551 SALMON CT, OLDSMAR, FL 34677

    $349,9005 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


  • 1810 DRIFTWOOD CIR S, OLDSMAR, FL 34677

    $369,00041 Days on yellowkey   MLS ID: TB8490101

    REDUCED by $1,000 (0.3%) on 04/23/2026

    For Sale TB8490101 - 1810 DRIFTWOOD CIR S, OLDSMAR, FL 34677 30 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1456
       Built: 1973   Tax: $1,957 (2025)
    Community: Harbor Palms
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,185 (change assumption)
    Mortgage ($2,022) + Taxes in 2025 ($163)


    Taxes:$1,957

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 405 HOLLY HILL RD, OLDSMAR, FL 34677

    $660,0006 Days on yellowkey   MLS ID: TB8503763

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

    For Sale TB8503763 - 405 HOLLY HILL RD, OLDSMAR, FL 34677 57 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 2311
       Built: 1979
    Monthly Fee: $149
       Tax: $3,606 (2026)
    Community: East Lake Woodlands
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $4,066 (change assumption)
    Mortgage ($3,616) + Fees ($149) + Taxes in 2026 ($301)


    Taxes:$3,606

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2026

    Middle School: Carwise Middle-PN


  • 4953 POINTE CIR, OLDSMAR, FL 34677

    $885,0009 Days on yellowkey   MLS ID: TB8502016

    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: $5,964 (change assumption)
    Mortgage ($4,849) + 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




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.