10,688

Oldsmar, FL Homes

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  • /32

    $475,000

    • 3 Beds
    • 3 Baths
    • 1,834 Sq Ft

    117 Brent Cir, Oldsmar, FL 34677

    Come and tour this cozy 3 bedroom, 3 bathroom waterfront townhouse and you will quickly see how easy it is to embrace the lifestyle that makes Florida living so desirable. This 1834 sq ft, 3 level townhouse delivers comfortable maintenance free living in a space where you can be in for years to come. Soak in endless water views as you sip your morning coffee or unwind with a good book, from 2

    Jaybee Racaza-Benitez BLAKE REAL ESTATE INC

    117 Brent Cir, Oldsmar, FL 34677
  • /2

    $705,000

    Sold Apr 23, 2026

    335 Palmdale Dr, Oldsmar, FL 34677

    • 5 Beds
    • 3 Baths
    • 3,035 Sq Ft
    • Built 2001

    Last Sold Summary

    • 19% Below List Price
    • $232/SF
    • 105 Days On Market

    Current Estimated Value $734,543

    Last Listing Agent Troy Walseth KELLER WILLIAMS GULF BEACHES

    335 Palmdale Dr, Oldsmar, FL 34677
    • /2

      Est $382,362

      Not Listed For Sale

      602 Lemonwood Dr, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,572 Sq Ft
      • Built 1974
      602 Lemonwood Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 105 Days On Market

      Last Listing Agent Ginger Tatarzewski FUTURE HOME REALTY INC

  • /87

    $515,000

    $10K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft

    549 Longwood Cir, Oldsmar, FL 34677

    Welcome to your private retreat in the heart of Oldsmar. Located in the desirable Longwood community, this beautifully maintained home offers the perfect blend of comfort, charm, and Florida living. Surrounded by mature landscaping and peaceful streets, 549 Longwood Circle features spacious living areas, abundant natural light, and an inviting layout ideal for both entertaining and everyday

    Susan Kolesnikov REALTY ONE GROUP MVP

    549 Longwood Cir, Oldsmar, FL 34677
  • /2

    $572,500

    Sold Apr 15, 2026

    1703 Bayhill Dr, Oldsmar, FL 34677

    • 4 Beds
    • 2.5 Baths
    • 1,963 Sq Ft
    • Built 1994

    Last Sold Summary

    • 1% Below List Price
    • $292/SF
    • 4 Days On Market

    Current Estimated Value $571,021

    Last Listing Agent Vanessa Leonard KELLER WILLIAMS REALTY- PALM HARBOR

    1703 Bayhill Dr, Oldsmar, FL 34677
    • /13

      Est $328,243

      Not Listed For Sale

      1822 Driftwood Cir S, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,269 Sq Ft
      • Built 1973
      1822 Driftwood Cir S, Oldsmar, FL 34677

      Last Sold Summary

      • 21 Days On Market

      Last Listing Agent Carrie Helms COLDWELL BANKER REALTY

  • /65

    $1,149,900

    • 4 Beds
    • 3 Baths
    • 3,098 Sq Ft

    35 Greenhaven Trail, Oldsmar, FL 34677

    Homes like this rarely become available in the highly sought-after gated community of East Lake Woods. Completely remodeled and situated on over a quarter acre overlooking a tranquil pond, this exceptional residence offers the perfect blend of luxury, comfort, and functionality. From the moment you arrive, you'll appreciate the expansive driveway, oversized three car garage, and impressive curb

    David Ares CHARLES RUTENBERG REALTY INC

    35 Greenhaven Trail, Oldsmar, FL 34677
  • /2

    $750,000

    Sold Nov 25, 2025

    4992 Augusta Ave, Oldsmar, FL 34677

    • 3 Beds
    • 3 Baths
    • 2,292 Sq Ft
    • Built 1994

    Last Sold Summary

    • $327/SF
    • 2 Days On Market

    Current Estimated Value $766,340

    Last Listing Agent Pat Kaylor PAT KAYLOR PROPERTIES, INC.

    4992 Augusta Ave, Oldsmar, FL 34677
    • /30

      Est $376,028

      Not Listed For Sale

      1818 Driftwood Cir S, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,536 Sq Ft
      • Built 1972
      1818 Driftwood Cir S, Oldsmar, FL 34677

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent Ryan Nowlin RE/MAX ACTION FIRST OF FLORIDA

  • /99

    $3,800,000

    Pending
    • 4 Beds
    • 6 Baths
    • 5,675 Sq Ft

    732 Shore Dr E, Oldsmar, FL 34677

    Custom Waterfront Estate on Old Tampa Bay Set on 1.72 acres with 150 feet of private frontage along Old Tampa Bay, this distinctive custom-built estate offers more than 5,600 square feet of elegant living and water views from nearly every room. A newly constructed 200-foot dock with a 13,000-pound boat lift puts the bay at your doorstep, while an 18-foot elevation keeps the home high and dry with

    Michael Goldstein CHARLES RUTENBERG REALTY INC

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

    $485,000

    Sold May 29, 2026

    420 Cypress View Dr, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,870 Sq Ft
    • Built 1998

    Last Sold Summary

    • $259/SF
    • 2 Days On Market

    Current Estimated Value $497,723

    Last Listing Agent Jeffrey Borham EXP REALTY LLC

    420 Cypress View Dr, Oldsmar, FL 34677
    • /28

      Est $424,124

      Not Listed For Sale

      510 Driftwood Cir W, Oldsmar, FL 34677

      • 4 Beds
      • 2 Baths
      • 1,680 Sq Ft
      • Built 1973
      510 Driftwood Cir W, Oldsmar, FL 34677

      Last Sold Summary

      • 19 Days On Market

      Last Listing Agent Larry Arth REALTY EXECUTIVES GALLERY

  • /71

    $246,000

    $18K PRICE DROP Under Contract
    • 2 Beds
    • 2.5 Baths
    • 1,200 Sq Ft

    205 Woods Landing Trail, Oldsmar, FL 34677

    Under contract-accepting backup offers. From the welcoming entrance foyer, visitors are immediately drawn to the peaceful wooded views at the rear of the home, creating a warm and inviting first impression. Welcome to this beautifully maintained two-bedroom, two-and-a-half-bath townhome in the gated community of East Lake Woodlands, one of Pinellas County's most sought-after neighborhoods.

    Karen Sewell CHARLES RUTENBERG REALTY INC

    205 Woods Landing Trail, Oldsmar, FL 34677
  • /2

    $520,000

    Sold Sep 25, 2025

    1600 Gray Bark Dr, Oldsmar, FL 34677

    • 4 Beds
    • 2.5 Baths
    • 2,270 Sq Ft
    • Built 1996

    Last Sold Summary

    • 17% Below List Price
    • $229/SF
    • 223 Days On Market

    Current Estimated Value $563,689

    Last Listing Agent Noah Rich PINEYWOODS REALTY LLC

    1600 Gray Bark Dr, Oldsmar, FL 34677
    • /35

      Est $475,302

      Not Listed For Sale

      500 Driftwood Cir W, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,830 Sq Ft
      • Built 1972
      500 Driftwood Cir W, Oldsmar, FL 34677

      Last Sold Summary

      • 1 Day On Market

      Last Listing Agent Julie Peluso CHARLES RUTENBERG REALTY INC

  • /34

    $359,900

    $20K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1811 Driftwood Cir S Unit 2, Oldsmar, FL 34677

    Welcome to this beautifully updated 3-bedroom, 2-bath home in the heart of Oldsmar! Offering 1,248 sq ft of well-designed living space, this move-in-ready property features a functional layout, abundant natural light, and modern updates throughout. Enjoy spacious living and dining areas that flow seamlessly, perfect for both everyday living and entertaining. The kitchen offers ample cabinetry and

    Julio Vasquez CHARLES RUTENBERG REALTY INC

    1811 Driftwood Cir S Unit 2, Oldsmar, FL 34677
  • /2

    $150,000

    Sold Jun 05, 2026

    106 W Cypress Ct Unit 106, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,054 Sq Ft
    • Built 1980

    Last Sold Summary

    • 9% Below List Price
    • $142/SF
    • 8 Days On Market

    Current Estimated Value $160,886

    Last Listing Agent Stacy Kitchell ENGEL & VOELKERS UPPER TAMPA BAY

    106 W Cypress Ct Unit 106, Oldsmar, FL 34677
    • /55

      Est $388,852

      Not Listed For Sale

      1802 Buttonwood Dr, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,477 Sq Ft
      • Built 1972
      1802 Buttonwood Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Chris Arata COLDWELL BANKER REALTY

  • /30

    $397,000

    $2K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1206 Sawgrass Ct, Oldsmar, FL 34677

    Under contract-accepting backup offers. Beautifully modernly updated 3-Bedroom, 2 bath home with a 1 car garage, in the desirable Forest Lakes Community in Oldsmar! This lovely home is situated on a peaceful cul-de-sac in an ideal location. As soon as you enter the home, you will feel welcomed by the charming entry, with the open floor plan, vaulted ceilings and elegant porcelain tile throughout

    Yandy Perez DALTON WADE INC

    1206 Sawgrass Ct, Oldsmar, FL 34677
  • /2

    $340,000

    Sold Jul 09, 2026

    551 Salmon Ct, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Built 2002

    Last Sold Summary

    • 3% Below List Price
    • $253/SF
    • 42 Days On Market

    Current Estimated Value $345,046

    Last Listing Agent Cathy McCarthy RE/MAX REALTEC GROUP INC

    551 Salmon Ct, Oldsmar, FL 34677
    • /27

      Est $541,036

      Not Listed For Sale

      414 Maplewood Dr, Oldsmar, FL 34677

      • 5 Beds
      • 3 Baths
      • 2,416 Sq Ft
      • Built 1973
      414 Maplewood Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 157 Days On Market

      Last Listing Agent Taylor Cresswell SELLSTATE COASTAL REALTY

  • /34

    $247,000

    • 2 Beds
    • 2 Baths
    • 1,320 Sq Ft

    407 Dolphin Dr S, Oldsmar, FL 34677

    Experience the charm of Gull-Aire Village 55+ in this beautifully renovated home, ready for its next owners. Boasting a spacious 1,320 square feet with stylish laminate flooring throughout, this residence is perfect for entertaining and comfortable living. The split-bedroom layout ensures privacy for both you and your guests, while both bathrooms feature luxurious walk-in showers for added

    Jayne Phoenix BHHS FLORIDA PROPERTIES GROUP

    407 Dolphin Dr S, Oldsmar, FL 34677
  • /2

    $563,000

    Sold Oct 03, 2025

    632 Lake Cypress Cir, Oldsmar, FL 34677

    • 4 Beds
    • 2 Baths
    • 1,906 Sq Ft
    • Built 1998

    Last Sold Summary

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

    Current Estimated Value $576,765

    Last Listing Agent Don Moore KELLER WILLIAMS REALTY- PALM HARBOR

    632 Lake Cypress Cir, Oldsmar, FL 34677
    • /2

      Est $396,904

      Not Listed For Sale

      80 Woodridge Ct, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,725 Sq Ft
      • Built 1987
      80 Woodridge Ct, Oldsmar, FL 34677

      Last Sold Summary

      • 51 Days On Market

      Last Listing Agent Donna Miller COMPASS FLORIDA LLC

  • /5

    $158,990

    $20K PRICE DROP Pending
    • 4 Beds
    • 2.5 Baths
    • 2,155 Sq Ft

    705 Shore Dr E, Oldsmar, FL 34677

    Short Sale. Short Sale - Listed price has not been negotiated or approved by the current lender. There is a possibility the list price will not be the accepted contract price. Enter at your own risk. Mold and water damage throughout the property from hurricane flooding. The roof needs to be replaced. The pool caved in from flooding. Walls, and appliances need to be replaced. The only good thing

    Michele Martinez GREAT AMERICAN REALTY

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

    $172,500

    Sold Sep 25, 2025

    213 Mary Dr, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,094 Sq Ft
    • Built 1981

    Last Sold Summary

    • 7% Below List Price
    • $158/SF
    • 42 Days On Market

    Current Estimated Value $176,208

    Last Listing Agent Kimberly Sobecki RE/MAX REALTEC GROUP INC

    213 Mary Dr, Oldsmar, FL 34677
    • /2

      Est $377,397

      Not Listed For Sale

      245 Woodridge Cir, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 1987
      245 Woodridge Cir, Oldsmar, FL 34677

      Last Sold Summary

      • 91 Days On Market

      Last Listing Agent Sara LaRock LAROCK REALTY & PROPERTY MGMT.

  • /65

    $550,000

    $75K PRICE DROP Under Contract
    • 4 Beds
    • 2 Baths
    • 2,138 Sq Ft

    438 Lafayette Blvd, Oldsmar, FL 34677

    Under contract-accepting backup offers. Beautiful Custom-built home is situated on 1⁄2 acre fenced-in lot (mol) No HOA, No deed restriction, Plenty of room for your Boat and RV! Featuring 4 Bedrooms plus an office, 2 baths and a screened-in heated pool. Circular driveway and etched glass front door welcome you into a wide-open floor plan with vaulted ceilings and lots of windows. Interior freshly

    Luigi Kalaj RE/MAX REALTEC GROUP INC

    438 Lafayette Blvd, Oldsmar, FL 34677
  • /2

    $200,000

    Sold Nov 14, 2025

    118 Edgewood Ct, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 900 Sq Ft
    • Built 1984

    Last Sold Summary

    • 7% Below List Price
    • $222/SF
    • 4 Days On Market

    Current Estimated Value $207,025

    Last Listing Agent Jacque Wiest CHARLES RUTENBERG REALTY INC

    118 Edgewood Ct, Oldsmar, FL 34677
    • /3

      Est $394,918

      Not Listed For Sale

      255 Woodridge Cir, Oldsmar, FL 34677

      • 3 Beds
      • 2.5 Baths
      • 1,700 Sq Ft
      • Built 1987
      255 Woodridge Cir, Oldsmar, FL 34677

      Last Sold Summary

      Last Listing Agent Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  • /36

    $450,000

    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    2410 Arch Ave, Oldsmar, FL 34677

    Imagine coming home to breathtaking waterfront surroundings, resort-style amenities, and maintenance-free living in one of Tampa Bay's most desirable gated communities. Welcome to Bayside Terrace, where this beautifully upgraded 3-bedroom, 2.5-bath townhome with a 1-car garage offers the perfect blend of luxury, convenience, and coastal lifestyle.Ideally situated just steps from the community

    Joseph Richards KELLER WILLIAMS TAMPA PROPERTIES

    2410 Arch Ave, Oldsmar, FL 34677
  • /2

    $185,000

    Sold Apr 07, 2026

    148 Douglas Rd W Unit C, Oldsmar, FL 34677

    • 2 Beds
    • 1.5 Baths
    • 1,080 Sq Ft
    • Built 1985

    Last Sold Summary

    • 19% Below List Price
    • $171/SF
    • 68 Days On Market

    Current Estimated Value $196,491

    Last Listing Agent Robert VanPamelen ARCHWATER REALTY LLC

    148 Douglas Rd W Unit C, Oldsmar, FL 34677
    • /59

      Est $399,944

      Not Listed For Sale

      50 Woodridge Cir, Oldsmar, FL 34677

      • 3 Beds
      • 3 Baths
      • 1,820 Sq Ft
      • Built 1984
      50 Woodridge Cir, Oldsmar, FL 34677

      Last Sold Summary

      • 6 Days On Market

      Last Listing Agent Cathy McCarthy RE/MAX REALTEC GROUP INC

  • /80

    $419,000

    $30K PRICE DROP
    • 3 Beds
    • 2 Baths
    • 1,280 Sq Ft

    347 Country Club Dr, Oldsmar, FL 34677

    "Move-In Ready"... Freshly Painted and Beautifully completely Refurbished Single Family Pool Home, (3) Bedrooms, (2) Baths with plenty of storage space, vehicles, boat and golf cart(s) parking. Luxury vinyl flooring throughout this split plan homes interior, picturesque French Door views to the pool and lanai deck, all new kitchen appliances and home systems installed. An expansive corner lot

    Frank Fundora PEOPLE'S CHOICE REALTY SVC LLC

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

    $250,000

    Sold Nov 19, 2025

    206 Dunkirk Rd, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,116 Sq Ft
    • Built 1959

    Last Sold Summary

    • 11% Below List Price
    • $224/SF
    • 52 Days On Market

    Current Estimated Value $279,931

    Last Listing Agent Jessica Christianson EXP REALTY LLC

    206 Dunkirk Rd, Oldsmar, FL 34677
    • /2

      Est $382,757

      Not Listed For Sale

      30 Woodridge Cir, Oldsmar, FL 34677

      • 3 Beds
      • 3 Baths
      • 2,100 Sq Ft
      • Built 1984
      30 Woodridge Cir, Oldsmar, FL 34677

      Last Sold Summary

      • 49 Days On Market

      Last Listing Agent Kimberly Sobecki RE/MAX REALTEC GROUP INC

  • /74

    $599,900

    $25K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,139 Sq Ft

    450 Cypress Creek Cir, Oldsmar, FL 34677

    Welcome to 450 Cypress Creek Circle, a beautifully renovated single-story home nestled within the prestigious gated community of East Lake Woodlands. Perfectly positioned on the golf course, this exceptional residence enjoys wide-open fairway views of hole #2 on the South Course at Ardea Country club with no homes directly behind, creating a peaceful backdrop for everyday living and entertaining.

    Mark Fazzini RE/MAX REALTEC GROUP INC

    450 Cypress Creek Cir, Oldsmar, FL 34677
  • /2

    $255,500

    Sold Apr 23, 2026

    121 Dolphin Dr S, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,392 Sq Ft
    • Built 1980

    Last Sold Summary

    • 6% Below List Price
    • $184/SF
    • 337 Days On Market

    Last Listing Agent Anne Hode AH REALTY SERVICES, LLC

    121 Dolphin Dr S, Oldsmar, FL 34677
    • /2

      Est $348,587

      Not Listed For Sale

      20 Woodridge Cir, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,883 Sq Ft
      • Built 1984
      20 Woodridge Cir, Oldsmar, FL 34677

      Last Sold Summary

      • 3 Days On Market

      Last Listing Agent Kimberly Sobecki RE/MAX REALTEC GROUP INC

  • /56

    $529,500

    $10K PRICE DROP Under Contract
    • 3 Beds
    • 2 Baths
    • 1,804 Sq Ft

    650 Sweetbriar Dr, Oldsmar, FL 34677

    Under contract-accepting backup offers. Beautifully maintained and situated on a professionally landscaped corner lot, this exceptional home offers outstanding curb appeal and an impressive list of upgrades throughout. The beautifully updated kitchen features modern finishes and abundant functionality, making it the perfect gathering place for family and friends. Step outside and enjoy your own

    Shannon Oleferchik FINE PROPERTIES

    650 Sweetbriar Dr, Oldsmar, FL 34677

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