10,799

Oldsmar, FL Homes

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  • /38

    $195,000

    • 2 Beds
    • 2 Baths
    • 879 Sq Ft

    204 Windward Place Unit 36, Oldsmar, FL 34677

    Welcome to 204 Windward Place #36, a well-maintained and move-in-ready condo located in the desirable East Lake Woodlands community in Oldsmar, Florida. This residence offers a comfortable layout with abundant natural light and a private outdoor space ideal for relaxing or enjoying morning coffee. The interior has been thoughtfully maintained, providing a clean and inviting living environment

    Robert Dinan BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    204 Windward Place Unit 36, Oldsmar, FL 34677
  • /2

    $510,000 Sold Feb 19, 2026

    4874 Westchester Ct, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,758 Sq Ft
    • Built 1996

    Last Sold Summary

    • 20% Below List Price
    • $290/SF
    • 135 Days On Market

    Current Estimated Value $515,146

    Last Listing Agent Alecia Savas COLDWELL BANKER REALTY

    4874 Westchester Ct, Oldsmar, FL 34677
    • /30

      Est $378,432 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

      • 10% Below List Price
      • $273/SF
      • 2 Days On Market
      • Last Sold Price $419,900
      • Jun 28, 2024

      Last Listing Agent Ryan Nowlin RE/MAX

  • /41

    $379,900

    • 3 Beds
    • 2 Baths
    • 1,323 Sq Ft

    413 Country Club Dr, Oldsmar, FL 34677

    Welcome to this stunning, fully renovated 3-bedroom, 2-bathroom waterfront home located in the highly desirable Oldsmar Country Club Estates. Situated on a spacious 0.21-acre lot with no HOA, this property offers a rare opportunity to enjoy true Florida living with direct water access. Follow the scenic water trail right from your backyard all the way out to Tampa Bay, making this a dream for

    Julian Jackson LOKATION

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

    $430,000 Sold Mar 10, 2026

    505 Oakwood Blvd, Oldsmar, FL 34677

    • 4 Beds
    • 2 Baths
    • 1,993 Sq Ft
    • Built 1969

    Last Sold Summary

    • 825% Above List Price
    • $216/SF
    • 115 Days On Market

    Current Estimated Value $446,014

    Last Listing Agent Amanda Lebiszczak CHARLES RUTENBERG REALTY INC

    505 Oakwood Blvd, Oldsmar, FL 34677
    • /28

      Est $428,134 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

      • 1% Above List Price
      • $253/SF
      • 19 Days On Market
      • Last Sold Price $425,000
      • Aug 18, 2023

      Last Listing Agent Larry Arth REALTY EXECUTIVES GALLERY

  • /44

    $160,000

    • 2 Beds
    • 2 Baths
    • 915 Sq Ft

    134 Sycamore Ln Unit H, Oldsmar, FL 34677

    This beautifully maintained 2 bedroom, 2 bath condo in fantastic Gardens of Forest lakes, offers perfect blend of comfort and convenience. As you step inside, you will be greeted by an open floor plan that seamlessly connects the living and kitchen areas. Kitchen features granite countertops, wood cabinets. The dining area opens to a charming balcony overlooking trees and it is perfect for

    Tatiana Russu FUTURE HOME REALTY INC

    134 Sycamore Ln Unit H, Oldsmar, FL 34677
  • /2

    $351,000 Sold Jun 26, 2025

    204 Lake Charles Ct, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft
    • Built 1984

    Last Sold Summary

    • 2% Below List Price
    • $292/SF
    • 4 Days On Market

    Current Estimated Value $358,093

    Last Listing Agent Brittany Wilson BAYSIDE EXECUTIVE REALTY

    204 Lake Charles Ct, Oldsmar, FL 34677
    • /35

      Est $496,458 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

      • 6% Below List Price
      • $290/SF
      • 1 Day On Market
      • Last Sold Price $530,000
      • Sep 18, 2023

      Last Listing Agent Julie Peluso CHARLES RUTENBERG REALTY INC

  • /56

    $345,000

    • 3 Beds
    • 2 Baths
    • 1,667 Sq Ft

    709 Lemonwood Dr, Oldsmar, FL 34677

    Welcome to this well-maintained 3-bedroom, 2-bath home offering 1,667 square feet of comfortable living space on a spacious 60x100 lot, located on a quiet street in desirable Oldsmar. This home features newer appliances, a 2025 hot water heater, and a 2022 AC system, providing peace of mind for years to come. Inside, you’ll find new carpet in Bedrooms 2 and 3, along with a bright and functional

    Jay Hundt PA PEOPLE'S CHOICE REALTY SVC LLC

    709 Lemonwood Dr, Oldsmar, FL 34677
  • /2

    $577,000 Sold Oct 23, 2025

    422 Cypress View Dr, Oldsmar, FL 34677

    • 4 Beds
    • 2.5 Baths
    • 2,143 Sq Ft
    • Built 1997

    Last Sold Summary

    • 10% Below List Price
    • $269/SF
    • 84 Days On Market

    Current Estimated Value $573,984

    Last Listing Agent Candice Kelly IAD FLORIDA LLC

    422 Cypress View Dr, Oldsmar, FL 34677
    • /55

      Est $374,056 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

      • 11% Below List Price
      • $284/SF
      • 7 Days On Market
      • Last Sold Price $420,000
      • Apr 09, 2024

      Last Listing Agent Chris Arata COLDWELL BANKER REALTY

  • /56

    $800,000 Pending

    • 4 Beds
    • 3 Baths
    • 2,673 Sq Ft

    2159 Warwick Dr, Oldsmar, FL 34677

    Under contract-accepting backup offers. It's time to buy in Eastlake Woodlands! Settle in to your dream home in the coveted subdivision of Warwick Hills within Eastlake Woodlands. Eastlake Woodlands is a renowned golf and tennis community that offers a full range of amenities for an additional membership including the fully remodeled Ardea Country Club, championship golf courses, tennis, pickle

    Cristina Lorenzo PALERMO REAL ESTATE PROF. INC.

    2159 Warwick Dr, Oldsmar, FL 34677
  • /2

    $215,000 Sold Jun 26, 2025

    165 Lakeview Way Unit 81, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 1,148 Sq Ft
    • Built 1980

    Last Sold Summary

    • 19% Below List Price
    • $187/SF
    • 204 Days On Market

    Current Estimated Value $206,201

    Last Listing Agent Danielle Dietz COLDWELL BANKER REALTY

    165 Lakeview Way Unit 81, Oldsmar, FL 34677
    • /27

      Est $529,857 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

      • 4% Above List Price
      • $211/SF
      • 157 Days On Market
      • Last Sold Price $510,000
      • Mar 06, 2024

      Last Listing Agent Taylor Cresswell SELLSTATE LEGACY REALTY

  • /26

    $184,000

    • 2 Beds
    • 2 Baths
    • 1,056 Sq Ft

    340 Canal Way, Oldsmar, FL 34677

    Welcome to easy Florida living in the sought-after 55+ community of Gull-Aire Village in Oldsmar. This well-maintained 2BR/2BA home offers a comfortable, open layout with updated flooring, a spacious living area, and a split-bedroom floor plan that gives both you and your guests privacy. The kitchen and bathrooms are clean and functional with room to make it your own, making this a great

    Sal Degaetano ACROPOLIS REALTY GROUP LLC

    340 Canal Way, Oldsmar, FL 34677
  • /2

    $340,000 Sold Dec 08, 2025

    504 Cabernet Way, Oldsmar, FL 34677

    • 3 Beds
    • 2.5 Baths
    • 1,525 Sq Ft
    • Built 2015

    Last Sold Summary

    • 3% Below List Price
    • $223/SF
    • 48 Days On Market

    Current Estimated Value $338,266

    Last Listing Agent David Weylie ELITE TAMPA BAY REALTY LLC

    504 Cabernet Way, Oldsmar, FL 34677
    • /2

      Est $392,521 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

      • 7% Below List Price
      • $243/SF
      • 51 Days On Market
      • Last Sold Price $420,000
      • Jul 24, 2024

      Last Listing Agent Donna Miller COMPASS FLORIDA LLC

  • /70

    $485,000 Pending

    • 4 Beds
    • 2 Baths
    • 1,692 Sq Ft

    835 Christina Cir, Oldsmar, FL 34677

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to this beautifully maintained 4-bedroom, 2-bath pool home in the highly sought-after Bays End community of Oldsmar, a private neighborhood of just 53 homes where properties rarely come available. Perfectly positioned with only one neighboring home, this property offers exceptional privacy along with

    Jonathan Hernandez COLDWELL BANKER REALTY

    835 Christina Cir, Oldsmar, FL 34677
  • /2

    $152,000 Sold Apr 03, 2026

    129 Cypress Ct Unit 129, Oldsmar, FL 34677

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

    Last Sold Summary

    • 12% Below List Price
    • $144/SF
    • 112 Days On Market

    Current Estimated Value $165,608

    Last Listing Agent Thomas Byrnes EXP REALTY LLC

    129 Cypress Ct Unit 129, Oldsmar, FL 34677
    • /2

      Est $385,657 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

      • 11% Below List Price
      • $254/SF
      • 91 Days On Market
      • Last Sold Price $432,500
      • Sep 09, 2024

      Last Listing Agent Sara LaRock LAROCK REALTY & PROPERTY MGMT.

  • /14

    $220,000

    • 2 Beds
    • 2.5 Baths
    • 1,264 Sq Ft

    62 Emerald Bay Dr, Oldsmar, FL 34677

    Heart of Oldsmar convenient to restaurants, shopping and Tampa. 2 Story, 2 Bedroom / 2.5 Bathroom Townhome in Oldsmar, AC 7/23, newer luxury vinyl flooring and newer paint.

    Lin Huang CHARLES RUTENBERG REALTY INC

    62 Emerald Bay Dr, Oldsmar, FL 34677
  • /2

    $145,000 Sold Dec 15, 2025

    500 Federal St, Oldsmar, FL 34677

    • Land
    • 14,810 Sq Ft
    • $426,471 per Acre

    Last Sold Summary

    • 3% Below List Price
    • 7 Days On Market

    Current Estimated Value $146,225

    Last Listing Agent Jessica Scialletti URBAN REAL ESTATE US

    500 Federal St, Oldsmar, FL 34677
    • /3

      Est $397,234 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

      • 10% Below List Price
      • $260/SF
      • Last Sold Price $442,000
      • Jan 09, 2024

      Last Listing Agent Stellar Non-Member Agent FL_MFRMLS

  • /15

    $220,000

    • 2 Beds
    • 2.5 Baths
    • 1,110 Sq Ft

    244 Countryside Key Blvd, Oldsmar, FL 34677

    Cozy 2-Bedroom, 2.5-Bath Townhome in the heart of Oldsmar. Brand new fresh carpets. The monthly HOA fees cover a wide range of services, including water, sewer, trash, cable, wifi, community pool, lawn and landscaping, roof maintenance and replacement, exterior pest control, and exterior building maintenance. Enjoy the convenience of being just minutes from the shopping, dining, a movie theater,

    Lin Huang CHARLES RUTENBERG REALTY INC

    244 Countryside Key Blvd, Oldsmar, FL 34677
  • /2

    $432,000 Sold Sep 24, 2025

    1630 Gray Bark Dr, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,358 Sq Ft
    • Built 1997

    Last Sold Summary

    • 7% Below List Price
    • $318/SF
    • 6 Days On Market

    Current Estimated Value $440,171

    Last Listing Agent Amy Denham COASTAL PROPERTIES GROUP INTERNATIONAL

    1630 Gray Bark Dr, Oldsmar, FL 34677
    • /59

      Est $405,458 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

      • 10% Below List Price
      • $247/SF
      • 6 Days On Market
      • Last Sold Price $450,000
      • Dec 18, 2023

      Last Listing Agent Cathy McCarthy RE/MAX

  • /52

    $199,995 Pre-Foreclosure

    • 2 Beds
    • 2 Baths
    • 1,048 Sq Ft

    372 Cobia Way, Oldsmar, FL 34677

    Welcome to 372 Cobia Way — one of the best locations in Gull-Aire Village, sitting directly across from the community pool, spa, and clubhouse! This resident-owned, 55+ golf cart friendly community in the heart of Oldsmar offers the best of Florida retirement living at an unbeatable value.Step inside to a bright, open floor plan featuring dark hardwood-style flooring and bold coastal teal

    Justin Cans IMPACT REALTY TAMPA BAY

    372 Cobia Way, Oldsmar, FL 34677
  • /2

    $359,000 Sold Jun 27, 2025

    405 Pine Ave S, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,175 Sq Ft
    • Built 1973

    Last Sold Summary

    • 12% Below List Price
    • $306/SF
    • 129 Days On Market

    Current Estimated Value $347,259

    Last Listing Agent Yordanka Henson VITA LUXURY REALTY LLC

    405 Pine Ave S, Oldsmar, FL 34677
    • /2

      Est $358,565 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

      • 2% Above List Price
      • $186/SF
      • 3 Days On Market
      • Last Sold Price $349,900
      • Mar 27, 2025

      Last Listing Agent Kimberly Sobecki RE/MAX

  • /58

    $520,000 Pending

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

    120 Brent Cir, Oldsmar, FL 34677

    Under contract-accepting backup offers. Are you dreaming of your own stylish urban OASIS surrounded by nature yet minutes from everywhere you want to be? Experience effortless coastal living in this exceptional waterfront townhome, perfectly designed for those who appreciate space, light and direct access to the water. Featuring two private boat slips, this residence offers a RARE opportunity to

    Darren Booth COMPASS FLORIDA LLC

    120 Brent Cir, Oldsmar, FL 34677
  • /2

    $246,000 Sold Oct 17, 2025

    75 Emerald Bay Dr, Oldsmar, FL 34677

    • 3 Beds
    • 2.5 Baths
    • 1,339 Sq Ft
    • Built 2004

    Last Sold Summary

    • 9% Below List Price
    • $184/SF
    • 73 Days On Market

    Current Estimated Value $250,230

    Last Listing Agent Tabitha Clark EXP REALTY LLC

    75 Emerald Bay Dr, Oldsmar, FL 34677
    • /27

      Est $290,219 Not Listed For Sale

      50 Lance Ct, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,250 Sq Ft
      • Built 1981
      50 Lance Ct, Oldsmar, FL 34677

      Last Sold Summary

      • 10% Below List Price
      • $259/SF
      • 75 Days On Market
      • Last Sold Price $324,000
      • Sep 05, 2023

      Last Listing Agent Raul Rivera CHARLES RUTENBERG REALTY INC

  • /15

    $315,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,186 Sq Ft

    1204 Forestwood Dr, Oldsmar, FL 34677

    Picture yourself at 1204 Forestwood Dr, a residence recently refreshed with fresh interior paint and new appliances throughout. A cozy fireplace adds comfort, complementing the kitchen's all stainless steel appliances. The exterior features a covered patio that extends to a fully fenced in backyard. Ready to enjoy stylish updates and outdoor living. Included 100-Day Home Warranty with buyer

    Karen Albright OPENDOOR BROKERAGE LLC

    1204 Forestwood Dr, Oldsmar, FL 34677
  • /2

    $612,000 Sold Jan 13, 2026

    5163 Pinnacle Dr, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,886 Sq Ft
    • Built 1995

    Last Sold Summary

    • 7% Below List Price
    • $324/SF
    • 69 Days On Market

    Current Estimated Value $608,053

    Last Listing Agent Heather Viviano RE/MAX REALTEC GROUP INC

    5163 Pinnacle Dr, Oldsmar, FL 34677
    • /2

      Est $287,552 Not Listed For Sale

      170 Ashley Ln, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,250 Sq Ft
      • Built 1981
      170 Ashley Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 10% Below List Price
      • $256/SF
      • 7 Days On Market
      • Last Sold Price $320,000
      • Aug 06, 2024

      Last Listing Agent Terri Harrington VUE REALTY, LLC

  • /31

    $239,000

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

    117 E Cypress Ct Unit 117, Oldsmar, FL 34677

    **COME ON IN - MAKE YOURSELF AT HOME ** This 2 Bed 2 Bath GROUND FLOOR unit has been totally REMODELLED to an exceptionally high standard!! New Floors, New Bathrooms, New Windows, MOVE IN READY!! And what's more?? NOT OVERLOOKED at the rear!!! Enjoy your morning coffee or evening drink on the front enclosed patio or watch the wildlife from the rear patio .. you have a choice!! Within easy walking

    Joanne Todd RE/MAX REALTEC GROUP INC

    117 E Cypress Ct Unit 117, Oldsmar, FL 34677
  • /2

    $195,000 Sold Mar 31, 2026

    106 Camille Ct, Oldsmar, FL 34677

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

    Last Sold Summary

    • 2% Below List Price
    • $178/SF
    • 5 Days On Market

    Current Estimated Value $198,369

    Last Listing Agent Bob McCaffery BHHS FLORIDA PROPERTIES GROUP

    106 Camille Ct, Oldsmar, FL 34677
    • /2

      Est $375,025 Not Listed For Sale

      60 Ashley Ln, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,850 Sq Ft
      • Built 1981
      60 Ashley Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 7% Below List Price
      • $217/SF
      • 71 Days On Market
      • Last Sold Price $402,000
      • Feb 25, 2025

      Last Listing Agent Yanya McReynolds PEOPLE'S TRUST REALTY

  • /46

    $389,000

    • 4 Beds
    • 2 Baths
    • 1,288 Sq Ft

    324 Country Club Dr, Oldsmar, FL 34677

    Home Renovated to Perfection!**Welcome to your new home - a stunning, newly renovated home offering comfort and style. Located in a quiet and cozy area, this property is perfect for families looking for space and modernity.- **4 spacious rooms**: Ideal for the comfort of the whole family.- **2 completely renovated bathrooms**: With modern and elegant finishes.- **Large kitchen**:

    Aime Alfonso VITA LUXURY REALTY LLC

    324 Country Club Dr, Oldsmar, FL 34677

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