REFINE SEARCH
Status
Keywords
Price
 
Bedrooms
Bathrooms
Garages
Liv Area Sq Ft
Min Year
Max Year
Property Types
No Image
Age Restricted
Foreclosure
Short Sale
Pets Allowed
Furnished
Pool
Spa
Reduced Price
Back on yellowkey
Possible Short Term Rental
Carports
Max Association Fee (monthly)
Max Monthly Payment
Search

Oldsmar Homes For Sale & Real Estate - 204 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

Sort:
  • 340 CANAL WAY, OLDSMAR, FL 34677

    $184,00040 Days on yellowkey   MLS ID: TB8491525

    REDUCED by $14,000 (7.1%) on 05/06/2026

    For Sale TB8491525 - 340 CANAL WAY, OLDSMAR, FL 34677 26 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1056
       Built: 1993
    Monthly Fee: $50
       Tax: $2,288 (2025)
    Community: Gull-Aire Village
    Manufactured Home


    Estimated Monthly Payment: $1,249 (change assumption)
    Mortgage ($1,008) + Fees ($50) + Taxes in 2025 ($191)


    Taxes:$2,288

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 475 WOODS LANDING TRL, OLDSMAR, FL 34677

    $255,000121 Days on yellowkey   MLS ID: A4676723

    0 Days Off yellowkey (back on 5/6/2026)

    For Sale A4676723 - 475 WOODS LANDING TRL, OLDSMAR, FL 34677 37 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1200
       Built: 1984
    Monthly Fee: $591
       Tax: $4,082 (2024)
    Community: East Lake Woodlands Woods Landing Twnhms
    Townhouse


    Estimated Monthly Payment: $2,328 (change assumption)
    Mortgage ($1,397) + Fees ($591) + Taxes in 2024 ($340)


    Taxes:$4,082

    Elementary School: Forest Lakes Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2024

    Middle School: Carwise Middle-PN


  • 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


  • 291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677

    $240,000112 Days on yellowkey   MLS ID: TB8463435

    REDUCED by $9,900 (4.0%) on 05/06/2026

    For Sale TB8463435 - 291 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677 34 photos

    Bed: 2   Bath: 2.5
    Liv Area Sq Ft: 1110
       Built: 1996
    Monthly Fee: $454
       Tax: $2,205 (2025)
    Community: Countryside Key
    Townhouse


    Estimated Monthly Payment: $1,953 (change assumption)
    Mortgage ($1,315) + Fees ($454) + Taxes in 2025 ($184)


    Taxes:$2,205

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 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


  • 417 DOLPHIN DR S, OLDSMAR, FL 34677

    $269,0005 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


  • 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


  • 209 CORKWOOD LN, OLDSMAR, FL 34677

    $245,408326 Days on yellowkey   MLS ID: TB8396745

    INCREASED by $508 (0.2%) on 04/17/2026

    For Sale TB8396745 - 209 CORKWOOD LN, OLDSMAR, FL 34677 30 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 900
       Built: 1984
    Monthly Fee: $268
       Tax: $2,960 (2024)
    Community: Villas Of Forest Lakes
    Villa


    Estimated Monthly Payment: $1,859 (change assumption)
    Mortgage ($1,345) + Fees ($268) + Taxes in 2024 ($247)


    Taxes:$2,960

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 2031 DOVER CT, OLDSMAR, FL 34677

    $289,00015 Days on yellowkey   MLS ID: TB8500444

    REDUCED by $11,000 (3.7%) on 05/05/2026

    For Sale TB8500444 - 2031 DOVER CT, OLDSMAR, FL 34677 33 photos

    Bed: 2   Bath: 2.0   Gar: 1
    Liv Area Sq Ft: 1215
       Built: 1982
    Monthly Fee: $135
       Tax: $4,212 (2025)
    Community: Bayside Meadows Ph Ii
    Villa


    Estimated Monthly Payment: $2,070 (change assumption)
    Mortgage ($1,584) + Fees ($135) + Taxes in 2025 ($351)


    Taxes:$4,212

    Elementary School: None

    High School: None

    Tax Year: 2025

    Middle School: None


  • 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


  • 433 SAILFISH BLVD, OLDSMAR, FL 34677

    $256,00065 Days on yellowkey   MLS ID: TB8481608

    REDUCED by $3,000 (1.2%) on 04/06/2026

    For Sale TB8481608 - 433 SAILFISH BLVD, OLDSMAR, FL 34677 48 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 960
       Built: 1987
    Monthly Fee: $70
       Tax: $1,585 (2025)
    Community: Gull-Aire Village
    Spa: No

    Manufactured Home


    Estimated Monthly Payment: $1,605 (change assumption)
    Mortgage ($1,403) + Fees ($70) + Taxes in 2025 ($132)


    Taxes:$1,585

    Elementary School: Oldsmar Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 10 LESLEY LN, OLDSMAR, FL 34677

    $310,00012 Days on yellowkey   MLS ID: TB8501611

    For Sale TB8501611 - 10 LESLEY LN, OLDSMAR, FL 34677 44 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1250
       Built: 1982
    Monthly Fee: $451
       Tax: $3,869 (2025)
    Community: Quail Forest Cluster Homes
    Spa: No

    Villa


    Estimated Monthly Payment: $2,472 (change assumption)
    Mortgage ($1,699) + Fees ($451) + Taxes in 2025 ($322)


    Taxes:$3,869

    Elementary School: Cypress Woods Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN


  • 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


  • 403 E TUSCAN LN E, OLDSMAR, FL 34677

    $330,000382 Days on yellowkey   MLS ID: TB8376561

    1 Days Off yellowkey (back on 1/14/2026)

    For Sale TB8376561 - 403 E TUSCAN LN E, OLDSMAR, FL 34677 27 photos

    Bed: 3   Bath: 2.5   Gar: 1
    Liv Area Sq Ft: 1525
       Built: 2015
    Monthly Fee: $333
       Tax: $5,075 (2024)
    Community: Tuscany Woods South
    Townhouse


    Estimated Monthly Payment: $2,564 (change assumption)
    Mortgage ($1,808) + Fees ($333) + Taxes in 2024 ($423)


    Taxes:$5,075

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 106 LAKESIDE CT, OLDSMAR, FL 34677

    $158,000398 Days on yellowkey   MLS ID: TB8350281

    REDUCED by $2,000 (1.3%) on 04/14/2026

    For Sale TB8350281 - 106 LAKESIDE CT, OLDSMAR, FL 34677 13 photos

    Bed: 2   Bath: 2.0
    Liv Area Sq Ft: 1094
       Built: 1981   Tax: $2,932 (2024)
    Community: East Lake Woodlands Condo
    Condo


    Estimated Monthly Payment: $1,110 (change assumption)
    Mortgage ($866) + Taxes in 2024 ($244)


    Taxes:$2,932

    Elementary School: None

    High School: None

    Tax Year: 2024

    Middle School: None


  • 388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677

    $246,00075 Days on yellowkey   MLS ID: TB8478422

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

    For Sale TB8478422 - 388 COUNTRYSIDE KEY BLVD, OLDSMAR, FL 34677 33 photos

    Bed: 2   Bath: 1.5
    Liv Area Sq Ft: 1105
       Built: 1997
    Monthly Fee: $433
       Tax: $1,771 (2025)
    Community: Countryside Key
    Townhouse


    Estimated Monthly Payment: $1,929 (change assumption)
    Mortgage ($1,348) + Fees ($433) + Taxes in 2025 ($148)


    Taxes:$1,771

    Elementary School: Curlew Creek Elementary-PN

    High School: East Lake High-PN

    Tax Year: 2025

    Middle School: Carwise Middle-PN




Why Bother Searching Elsewhere for Oldsmar Homes for Sale and Other Real Estate?

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.