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Oldsmar Single Family Homes For Sale - 102 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

    $399,9002 Days on yellowkey   MLS ID: TB8502335

    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: $2,488 (change assumption)
    Mortgage ($2,191) + 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


  • 2272 WARWICK DR, OLDSMAR, FL 34677

    $725,0002 Days on yellowkey   MLS ID: TB8502055

    For Sale TB8502055 - 2272 WARWICK DR, OLDSMAR, FL 34677 46 photos

    Bed: 4   Bath: 3.0   Gar: 3
    Liv Area Sq Ft: 2512
       Built: 1995
    Monthly Fee: $133
       Tax: $3,084 (2025)
    Community: Warwick Hills
    Spa: No

    Single Family


    Estimated Monthly Payment: $4,362 (change assumption)
    Mortgage ($3,973) + Fees ($133) + Taxes in 2025 ($257)


    Taxes:$3,084

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 2151 DIAMOND CT, OLDSMAR, FL 34677

    $1,350,000185 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


  • 1806 FOREST DR, OLDSMAR, FL 34677

    $418,000182 Days on yellowkey   MLS ID: TB8442794

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

    For Sale TB8442794 - 1806 FOREST DR, OLDSMAR, FL 34677 24 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1539
       Built: 1973   Tax: $4,086 (2024)
    Community: Harbor Palms
    Single Family


    Estimated Monthly Payment: $2,631 (change assumption)
    Mortgage ($2,290) + Taxes in 2024 ($340)


    Taxes:$4,086

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 507 SHORE DR E, OLDSMAR, FL 34677

    $239,00042 Days on yellowkey   MLS ID: TB8488465

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

    For Sale TB8488465 - 507 SHORE DR E, OLDSMAR, FL 34677 8 photos

    Bed: 3   Bath: 3.0   Gar: 1
    Liv Area Sq Ft: 1237
       Built: 1972   Tax: $1,158 (2025)
    Community: Tampashores Bay Sec
    Single Family


    Estimated Monthly Payment: $1,406 (change assumption)
    Mortgage ($1,310) + Taxes in 2025 ($96)


    Taxes:$1,158

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 382 ROSALIND LN, OLDSMAR, FL 34677

    $822,000285 Days on yellowkey   MLS ID: TB8408993

    For Sale TB8408993 - 382 ROSALIND LN, OLDSMAR, FL 34677 75 photos

    Bed: 4   Bath: 3.0   Gar: 2
    Liv Area Sq Ft: 3273
       Built: 2001
    Monthly Fee: $100
       Tax: $8,003 (2024)
    Community: Bay Arbor
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,271 (change assumption)
    Mortgage ($4,504) + Fees ($100) + Taxes in 2024 ($667)


    Taxes:$8,003

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1802 CHINABERRY DR, OLDSMAR, FL 34677

    $375,000192 Days on yellowkey   MLS ID: TB8439498

    INCREASED by $6,000 (1.6%) on 04/30/2026

    For Sale TB8439498 - 1802 CHINABERRY DR, OLDSMAR, FL 34677 34 photos

    Bed: 2   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1358
       Built: 1972   Tax: $865 (2024)
    Community: Harbor Palms-Unit One
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,127 (change assumption)
    Mortgage ($2,055) + Taxes in 2024 ($72)


    Taxes:$865

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 470 HICKORYNUT AVE, OLDSMAR, FL 34677

    $795,00050 Days on yellowkey   MLS ID: TB8485715

    REDUCED by $20,000 (2.5%) on 04/02/2026

    For Sale TB8485715 - 470 HICKORYNUT AVE, OLDSMAR, FL 34677 37 photos

    Bed: 4   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2922
       Built: 1987
    Monthly Fee: $110
       Tax: $10,515 (2025)
    Community: East Lake Woodlands
    Spa: Yes

    Single Family


    Estimated Monthly Payment: $5,342 (change assumption)
    Mortgage ($4,356) + Fees ($110) + Taxes in 2025 ($876)


    Taxes:$10,515

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 105 KILSYTHE ST, OLDSMAR, FL 34677

    $305,000Listed 04/30/2026 7:18AM   MLS ID: TB8502588

    For Sale TB8502588 - 105 KILSYTHE ST, OLDSMAR, FL 34677 65 photos

    Bed: 3   Bath: 2.0   Gar: 2
    Liv Area Sq Ft: 1036
       Built: 1981   Tax: $4,256 (2025)
    Community: Shoreview Ph I
    Single Family


    Estimated Monthly Payment: $2,026 (change assumption)
    Mortgage ($1,671) + Taxes in 2025 ($355)


    Taxes:$4,256

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 313 JEFFERSON AVE S, OLDSMAR, FL 34677

    $450,0001 Day on yellowkey   MLS ID: TB8502786

    For Sale TB8502786 - 313 JEFFERSON AVE S, OLDSMAR, FL 34677 63 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1841
       Built: 1940   Tax: $4,298 (2025)
    Community: Oldsmar Rev Map
    Single Family


    Estimated Monthly Payment: $2,824 (change assumption)
    Mortgage ($2,466) + Taxes in 2025 ($358)


    Taxes:$4,298

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 395 WINGATE CIR, OLDSMAR, FL 34677

    $575,000161 Days on yellowkey   MLS ID: TB8450027

    REDUCED by $15,000 (2.5%) on 04/29/2026

    For Sale TB8450027 - 395 WINGATE CIR, OLDSMAR, FL 34677 77 photos

    Bed: 5   Bath: 2.5   Gar: 3
    Liv Area Sq Ft: 2827
       Built: 2001
    Monthly Fee: $100
       Tax: $9,963 (2025)
    Community: Bay Arbor
    Single Family


    Estimated Monthly Payment: $4,081 (change assumption)
    Mortgage ($3,151) + Fees ($100) + Taxes in 2025 ($830)


    Taxes:$9,963

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 509 CYPRESS VIEW DR, OLDSMAR, FL 34677

    $634,00012 Days on yellowkey   MLS ID: TB8496854

    REDUCED by $15,000 (2.3%) on 04/27/2026

    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: $4,022 (change assumption)
    Mortgage ($3,474) + Fees ($140) + Taxes in 2025 ($409)


    Taxes:$4,902

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 208 CUTLASS WAY, OLDSMAR, FL 34677

    $350,0006 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


  • 103 CUTLASS WAY, OLDSMAR, FL 34677

    $345,00066 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


  • 316 COUNTRY CLUB DR, OLDSMAR, FL 34677

    $329,00078 Days on yellowkey   MLS ID: TB8475078

    REDUCED by $10,000 (2.9%) on 04/15/2026

    For Sale TB8475078 - 316 COUNTRY CLUB DR, OLDSMAR, FL 34677 30 photos

    Bed: 3   Bath: 2.0
    Liv Area Sq Ft: 1344
       Built: 1960   Tax: $562 (2025)
    Community: Oldsmar Country Club Estates Sec 3
    Single Family


    Estimated Monthly Payment: $1,850 (change assumption)
    Mortgage ($1,803) + Taxes in 2025 ($47)


    Taxes:$562

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677

    $379,900164 Days on yellowkey   MLS ID: TB8447176

    0 Days Off yellowkey (back on 4/24/2026)

    For Sale TB8447176 - 1820 DRIFTWOOD CIR N, OLDSMAR, FL 34677 31 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1528
       Built: 1973   Tax: $1,160 (2024)
    Community: Harbor Palms-Unit Two
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,178 (change assumption)
    Mortgage ($2,082) + Taxes in 2024 ($97)


    Taxes:$1,160

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 1362 E LAKE WOODLANDS PKWY, OLDSMAR, FL 34677

    $849,00097 Days on yellowkey   MLS ID: TB8467569

    3 Days Off yellowkey (back on 4/29/2026)

    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


  • 1802 FOREST DR, OLDSMAR, FL 34677

    $365,000163 Days on yellowkey   MLS ID: O6361686

    0 Days Off yellowkey (back on 3/28/2026)

    For Sale O6361686 - 1802 FOREST DR, OLDSMAR, FL 34677 25 photos

    Bed: 3   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1607
       Built: 1973   Tax: $2,998 (2024)
    Community: Harbor Palms-Unit Three
    Spa: No

    Single Family


    Estimated Monthly Payment: $2,250 (change assumption)
    Mortgage ($2,000) + Taxes in 2024 ($250)


    Taxes:$2,998

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 311 VISTA CRUISER LN, OLDSMAR, FL 34677

    $350,000157 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


  • 4953 POINTE CIR, OLDSMAR, FL 34677

    $885,0003 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.