10,815

Oldsmar, FL Homes

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  • /31

    $349,950

    $50K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,670 Sq Ft

    307 Country Club Dr, Oldsmar, FL 34677

    Virtually Staged. HONEY STOP THE CAR! THIS IS THE ONE! LOCATION LOCATION LOCATION! Welcome to this FULLY RENOVATED, PRIME OLDSMAR LOCATION. This RARE OPPORTUNITY is a 3 Bed 2 Bath Home that checks every box for buyers looking for a move-in-ready property and investors searching for a smart opportunity in one of Tampa Bay’s fastest-growing hidden gems. This fully updated residence has been

    Mark Fazzini RE/MAX REALTEC GROUP INC

    307 Country Club Dr, Oldsmar, FL 34677
  • /2

    $600,000

    Sold Nov 20, 2025

    341 Bay Arbor Blvd, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 2,034 Sq Ft
    • Built 2001

    Last Sold Summary

    • 4% Below List Price
    • $295/SF
    • 76 Days On Market

    Current Estimated Value $616,222

    Last Listing Agent Christina Nostro MIHARA & ASSOCIATES INC.

    341 Bay Arbor Blvd, Oldsmar, FL 34677
    • /6

      Not Listed For Sale

      505 Saint Petersburg Dr W, Oldsmar, FL 34677

      • 2 Beds
      • Built 1956
      505 Saint Petersburg Dr W, Oldsmar, FL 34677

      Last Sold Summary

      • 24 Days On Market

  • /57

    $575,000

    $10K PRICE DROP
    • 6 Beds
    • 2.5 Baths
    • 2,867 Sq Ft

    1758 Oak Pond Ct, Oldsmar, FL 34677

    Virtually Staged. ROOM TO ROAM!!! From the moment you arrive at 1758 Oak Pond, the 6 bedroom 3 bath home’s beautifully maintained exterior and impressive curb appeal set the tone for the exceptional living experience within. A spacious two-car garage and elegant front entry welcome you inside, where a dramatic two-story foyer creates an immediate sense of grandeur and sophistication. Natural

    Vanessa Leonard KELLER WILLIAMS REALTY- PALM HARBOR

    1758 Oak Pond Ct, Oldsmar, FL 34677
  • /2

    $810,000

    Sold Aug 29, 2025

    2075 Warwick Dr, Oldsmar, FL 34677

    • 4 Beds
    • 2.5 Baths
    • 3,294 Sq Ft
    • Built 1995

    Last Sold Summary

    • 7% Below List Price
    • $246/SF
    • 140 Days On Market

    Current Estimated Value $844,285

    Last Listing Agent Terry Long COLDWELL BANKER REALTY

    2075 Warwick Dr, Oldsmar, FL 34677
    • /43

      Not Listed For Sale

      490 Trout Ln, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,031 Sq Ft
      • Built 1993
      490 Trout Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 22 Days On Market

  • /16

    $269,000

    $40K PRICE DROP Pending
    • 3 Beds
    • 2.5 Baths
    • 1,452 Sq Ft

    202 Hemingway Dr, Oldsmar, FL 34677

    AS IS – Owner selling due to health concerns! This spacious 3-bedroom, 2.5 bath, townhome in the highly desirable community of Sun Ketch Townhomes of Cypress Lakes needs some cosmetic attention, but the structure and amenities are already there: vaulted ceilings, an inside laundry room, a kitchen pantry, a walk-in bathtub in the primary bathroom, and an enclosed porch, and much more. A new A/C

    Mark Ganier RE/MAX REALTEC GROUP INC

    202 Hemingway Dr, Oldsmar, FL 34677
  • /2

    $159,000

    Sold Jan 23, 2026

    127 Cypress Ln Unit 27, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,053 Sq Ft
    • Built 1980

    Last Sold Summary

    • $151/SF
    • 0 Days On Market

    Current Estimated Value $157,389

    Last Listing Agent Ashtin Brock BHHS FLORIDA PROPERTIES GROUP

    127 Cypress Ln Unit 27, Oldsmar, FL 34677
    • /18

      Est $365,550

      Not Listed For Sale

      1110 Vineyard Ln, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 1,525 Sq Ft
      • Built 2018
      1110 Vineyard Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 25 Days On Market

  • /22

    $390,000

    $9K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,748 Sq Ft

    415 Country Club Dr, Oldsmar, FL 34677

    Beautiful waterfront-view home overlooking the water from the backyard, located in the desirable Oldsmar Country Club Estates community. This fully renovated property features 4 bedrooms and 2 bathrooms and sits on a 0.21-acre lot with no HOA restrictions, offering comfort, functionality, and an excellent location.The home features new flooring throughout, a renovated kitchen with quartz

    Madelin Artigas FRIENDS REALTY LLC

    415 Country Club Dr, Oldsmar, FL 34677
  • /2

    $1,025,000

    Sold Aug 18, 2025

    1307 Forestedge Blvd, Oldsmar, FL 34677

    • 5 Beds
    • 3.5 Baths
    • 3,636 Sq Ft
    • Built 1990

    Last Sold Summary

    • 18% Below List Price
    • $282/SF
    • 70 Days On Market

    Current Estimated Value $1,052,144

    Last Listing Agent Mark Fazzini RE/MAX REALTEC GROUP INC

    1307 Forestedge Blvd, Oldsmar, FL 34677
    • /2

      Est $208,551

      Not Listed For Sale

      222 Nina Way Unit 222, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,094 Sq Ft
      • Built 1979
      222 Nina Way Unit 222, Oldsmar, FL 34677

      Last Sold Summary

      • 104 Days On Market

  • /33

    $255,000

    $45K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,215 Sq Ft

    2031 Dover Ct, Oldsmar, FL 34677

    Short Sale. -The shortsale process have been initiated to expedite closing. Buyers and their agents welcome to show, all offers are subject to lender approval. Excellent opportunity!- Welcome to your peaceful retreat! This beautifully updated 2-bedroom, 2-bathroom, 1-car garage villa combines comfort, charm, and convenience in a quiet, sidewalk-lined neighborhood ideal for leisurely strolls and a

    Jansz Umboh LOKATION

    2031 Dover Ct, Oldsmar, FL 34677
  • /2

    $295,000

    Sold Jan 26, 2026

    507 Canal Way, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft
    • Built 2002

    Last Sold Summary

    • 2% Below List Price
    • $197/SF
    • 38 Days On Market

    Last Listing Agent Sue Hirsch COLDWELL BANKER REALTY

    507 Canal Way, Oldsmar, FL 34677
    • /43

      Not Listed For Sale

      500 Cobia Way, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,480 Sq Ft
      • Built 1997
      500 Cobia Way, Oldsmar, FL 34677

      Last Sold Summary

      • 65 Days On Market

  • /31

    $900,000

    • 2 Beds
    • 2 Baths
    • 1,313 Sq Ft

    506 Shore Dr E, Oldsmar, FL 34677

    Exceptional waterfront opportunity on one of Oldsmar’s most desirable streets. Situated on a 75x205 (.33 acre) waterfront homesite overlooking beautiful Old Tampa Bay, this property presents a rare opportunity to create a custom luxury estate in an area experiencing significant redevelopment and impressive new construction. Currently utilized as a vacation rental, the home offers income producing

    John Pestalozzi Jr WESTWARD REAL ESTATE

    506 Shore Dr E, Oldsmar, FL 34677
  • /2

    $221,000

    Sold Feb 20, 2026

    106 Dolphin Dr E, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,092 Sq Ft
    • Built 1991

    Last Sold Summary

    • 1% Below List Price
    • $202/SF
    • 82 Days On Market

    Last Listing Agent Anne Hode AH REALTY SERVICES, LLC

    106 Dolphin Dr E, Oldsmar, FL 34677
    • /41

      Not Listed For Sale

      98 Dolphin Dr N, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,240 Sq Ft
      • Built 1984
      98 Dolphin Dr N, Oldsmar, FL 34677

      Last Sold Summary

      • 37 Days On Market

  • /10

    $50,000

    $99K PRICE DROP
    • Land
    • 3,920 Sq Ft
    • $555,556 per Acre

    257 Pelican Dr N, Oldsmar, FL 34677

    Rare opportunity to purchase a vacant lot in Gull-Aire Village for your new manufactured home. Gull-Aire Village is an active 55+ community and offers clubhouse, library, shuffleboard, Bocce ball court, and large heated pool & spa. Golf cart friendly. HOA is $70.00 per month. One pet-any size is allowed. If you have two pets the second pet will need an emotional support letter from Buyer’ doctor.

    Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

    257 Pelican Dr N, Oldsmar, FL 34677
  • /2

    $265,000

    Sold Jun 07, 2026

    0 St Petersburg Dr Unit U8068220, Oldsmar, FL 34677

    • Land
    • 23,958 Sq Ft
    • $481,818 per Acre

    Last Sold Summary

    • 41% Below List Price
    • 2,055 Days On Market

    Last Listing Agent Ginger Tatarzewski FUTURE HOME REALTY INC

    0 St Petersburg Dr Unit U8068220, Oldsmar, FL 34677
    • /17

      Not Listed For Sale

      0 St Petersburg Dr Unit MFRU8202338, Oldsmar, FL 34677

      0 St Petersburg Dr Unit MFRU8202338, Oldsmar, FL 34677

      Last Sold Summary

      • 87 Days On Market

  • /52

    $815,000

    Open Sat 2PM - 4PM
    • 3 Beds
    • 3.5 Baths
    • 3,058 Sq Ft

    743 Wellington Ct, Oldsmar, FL 34677

    Welcome to luxury living in the highly sought-after Wellington Estates community of Oldsmar. This stunning ENERGY STAR® certified residence offers over 3,000 square feet of thoughtfully designed living space featuring 3 bedrooms, a private den/office, 3.5 bathrooms, and an expansive bonus room that can easily serve as a media room, game room, home gym, or fourth bedroom. The home also includes a

    Tanner Tillung EXP REALTY LLC

    743 Wellington Ct, Oldsmar, FL 34677
  • /2

    $475,000

    Sold Aug 26, 2025

    50 Water Oak Way, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,921 Sq Ft
    • Built 1980

    Last Sold Summary

    • 5% Below List Price
    • $247/SF
    • 68 Days On Market

    Current Estimated Value $482,905

    Last Listing Agent Tom Orlando FUTURE HOME REALTY INC

    50 Water Oak Way, Oldsmar, FL 34677
    • /34

      Est $358,136

      Not Listed For Sale

      209 Cutlass Way, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 1,392 Sq Ft
      • Built 2016
      209 Cutlass Way, Oldsmar, FL 34677

      Last Sold Summary

      • 1 Day On Market

  • /21

    $210,000

    $72K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,250 Sq Ft

    80 Lance Ct, Oldsmar, FL 34677

    Must see to believe!!!!! OFFERING at 210k a TURN KEY 2/2 Villa located in the HIGHLY DESIRABLE Country Club, Golf and Tennis Community of Eastlake Woodlands. The solid block constructed END UNIT home offers extra outdoor space for relaxing with family and friends. As you approach this end unit at the end of a quiet cul-de-sac you'll find space to the right of the front door for storage, closet

    Casey Riordan LPT REALTY, LLC

    80 Lance Ct, Oldsmar, FL 34677
  • /2

    $745,000

    Sold Mar 09, 2026

    116 Shore Drive Place, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 2,148 Sq Ft
    • Built 1957

    Last Sold Summary

    • 15% Above List Price
    • $347/SF
    • 23 Days On Market

    Current Estimated Value $709,312

    Last Listing Agent Steve Doran COLDWELL BANKER REALTY

    116 Shore Drive Place, Oldsmar, FL 34677
    • /46

      Not Listed For Sale

      108 Woodlake Wynde Unit 108, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 924 Sq Ft
      • Built 1983
      108 Woodlake Wynde Unit 108, Oldsmar, FL 34677

      Last Sold Summary

      • 7 Days On Market

  • /31

    $160,000

    $25K PRICE DROP Pending
    • 2 Beds
    • 2 Baths
    • 1,053 Sq Ft

    256 Cypress Ln, Oldsmar, FL 34677

    Under contract-accepting backup offers. Lowest priced condo with updates in Eastlake Woodlands! Experience Eastlake Woodlands Country Club living at its finest in this beautifully updated Cypress Estates condo. Wake up to serene LARGE POND VIEW from your private, screened balcony—your morning coffee spot or evening retreat. Step inside to a bright, airy split floor plan where the spacious primary

    Tiffany Spyridakos SMITH & ASSOCIATES REAL ESTATE

    256 Cypress Ln, Oldsmar, FL 34677
  • /2

    $250,750

    Sold Mar 31, 2026

    202 Arlington Ave E, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,436 Sq Ft
    • Built 1961

    Last Sold Summary

    • 16% Below List Price
    • $175/SF
    • 8 Days On Market

    Current Estimated Value $265,805

    Last Listing Agent Mariela Saban MARK SPAIN REAL ESTATE

    202 Arlington Ave E, Oldsmar, FL 34677
    • /55

      Est $501,739

      Not Listed For Sale

      2214 Sunset Wind Loop, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 2,230 Sq Ft
      • Built 2019
      2214 Sunset Wind Loop, Oldsmar, FL 34677

      Last Sold Summary

      • 47 Days On Market

  • /44

    $399,000

    $26K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,952 Sq Ft

    600 S Woodlands Dr, Oldsmar, FL 34677

    One or more photo(s) has been virtually staged. This beautifully updated 3-bedroom, 2-bath attached villa style home is nestled in the highly sought-after Eastlake Woodlands community, offering serene preserve views in the front from your private fenced in patio and peaceful wooded and golf course views in the back. The home features a carport with a storage closet and a thoughtfully designed

    Jarod Brewer RE/MAX ACTION FIRST OF FLORIDA

    600 S Woodlands Dr, Oldsmar, FL 34677
  • /2

    $555,000

    Sold Feb 27, 2026

    1522 Riverdale Dr, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 2,355 Sq Ft
    • Built 1996

    Last Sold Summary

    • 20% Below List Price
    • $236/SF
    • 277 Days On Market

    Current Estimated Value $566,790

    Last Listing Agent Claudia Tweed COLDWELL BANKER REALTY

    1522 Riverdale Dr, Oldsmar, FL 34677
    • /6

      Not Listed For Sale

      0 Dartmouth Ave Unit U8194648, Oldsmar, FL 34677

      0 Dartmouth Ave Unit U8194648, Oldsmar, FL 34677

      Last Sold Summary

      • 125 Days On Market

  • /20

    $329,900

    $66K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,668 Sq Ft

    114 Clays Trail Unit 114, Oldsmar, FL 34677

    Light and bright 3BED/2BA Condominium with attached garage. Vaulted ceilings, potting shelves, sky-lites, and sunburst windows! Elegant living/dining room, posh master bath with shower and separate steeping tub. Split bedroom plan, spacious eat-in kitchen with Oak cabinetry and breakfast bar. Extensive tile flooring, tiled and screened in lanai, tranquil pond views and nature galore! East Lake

    George Kolistopoulos ADVANCED REALTY GROUP INC

    114 Clays Trail Unit 114, Oldsmar, FL 34677
  • /2

    $509,999

    Sold Aug 08, 2025

    514 Cedar Woods Dr, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,688 Sq Ft
    • Built 1998

    Last Sold Summary

    • 1% Below List Price
    • $302/SF
    • 129 Days On Market

    Current Estimated Value $528,973

    Last Listing Agent Caleb T Ritter 7TH AVE REALTY AND APPRAISAL

    514 Cedar Woods Dr, Oldsmar, FL 34677
    • /28

      Not Listed For Sale

      107 Dolphin Dr E, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,090 Sq Ft
      • Built 1991
      107 Dolphin Dr E, Oldsmar, FL 34677

      Last Sold Summary

      • 10 Days On Market

  • /66

    $660,000

    • 3 Beds
    • 2.5 Baths
    • 2,061 Sq Ft

    190 Water Oak Way, Oldsmar, FL 34677

    Experience the perfect blend of elegance, comfort, and breathtaking views in this exceptional home located in the highly desirable Woodland Estates within the gated community of East Lake Woodlands. Overlooking a serene pond and the 8th hole of the South Golf Course, this stunning residence offers the lifestyle you've always dreamed of.Step through the impressive double-door entry into a

    Leticia Dos Santos EXP Realty LLC

    190 Water Oak Way, Oldsmar, FL 34677
  • /2

    $305,000

    Sold Dec 09, 2025

    520 Canal Way, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,473 Sq Ft
    • Built 1995

    Last Sold Summary

    • 8% Below List Price
    • $207/SF
    • 149 Days On Market

    Last Listing Agent Chris Ziebell REALTY ONE GROUP BEYOND

    520 Canal Way, Oldsmar, FL 34677
    • /2

      Est $366,956

      Not Listed For Sale

      1212 Syrah Dr, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 1,773 Sq Ft
      • Built 2018
      1212 Syrah Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 31 Days On Market

  • /52

    $185,000

    • 2 Beds
    • 2 Baths
    • 875 Sq Ft

    202 Meadow Ln Unit 50, Oldsmar, FL 34677

    Welcome to this well-located, offering comfort and convenience. This residence features 2 bedrooms and 2 bathrooms, providing a functional layout suitable for a variety of living needs. Ideally positioned with easy access to major roadways, the home allows for a smooth commute to nearby areas such as Tampa and Clearwater. The surrounding area offers a wide range of shopping, dining, and

    Alexandra Muneton AXEN REALTY, LLC

    202 Meadow Ln Unit 50, Oldsmar, FL 34677

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