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Oldsmar: A Florida Charmer

Looking for that small town charm tucked between white powder beaches and the amenities provided by metropolitan living? Welcome to Oldsmar! Conveniently located between the city of Tampa and the beautiful Gulf Coast beaches, Oldsmar, with its small town feel, gets to have its cake and eat it too! Beautiful parks and a 300 acre natural preserve along with beautiful beaches and city life make Oldsmar a location that is hard to resist.


 

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549 Longwood Circle, Oldsmar image
549 Longwood Circle, Oldsmar $515,000 ▼

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...

  • 4 Beds
  • 2 Baths
  • Manors Of Forest Lakes The SubDv.
  • 34677 Zip Code
119 Brent Circle, Oldsmar image
119 Brent Circle, Oldsmar — Seaside Estates $525,000

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...

  • 3 Beds
  • 3 Baths
  • Seaside Estates SubDv.
  • 34677 Zip Code
601 Shore Drive E, Oldsmar image
601 Shore Drive E, Oldsmar $525,000

Welcome to this beautifully updated 3-bedroom, 2-bathroom home in the heart of Oldsmar, offering 1,856 square feet of thoughtfully designed living space on an oversized 0...

  • 3 Beds
  • 2 Baths
  • Tampashores Bay Sec SubDv.
  • 34677 Zip Code
158 Brent Circle, Oldsmar image
158 Brent Circle, Oldsmar — 158 $530,000

Endless sunsets create this picture perfect location in Seaside Estates, situated on Old Tampa Bay, where everyday living feels like a vacation. This townhome has 3 bedro...

  • 3 Beds
  • 3 Baths
  • Seaside Estates SubDv.
  • 34677 Zip Code
1795 Bayhill Drive, Oldsmar image
1795 Bayhill Drive, Oldsmar $539,900

This unique home exudes character and is located on a peaceful conservation lot with no rear neighbors situated within the secure, gated community of East Lake Woodlands!...

  • 2 Beds
  • 2 Baths
  • Creekside SubDv.
  • 34677 Zip Code
854 Christina Circle, Oldsmar image
854 Christina Circle, Oldsmar $548,000 ▼

Roof 2026!! Welcome to Bays End, a hidden gem community offering a peaceful setting with convenient access to everything the area has to offer. This well-maintained 3-bed...

  • 3 Beds
  • 2 Baths
  • Bays End SubDv.
  • 34677 Zip Code
438 Lafayette Boulevard, Oldsmar image
438 Lafayette Boulevard, Oldsmar $550,000 ▼

Beautiful Custom-built home is situated on ½ acre fenced-in lot (mol) No HOA, No deed restriction, Plenty of room for your Boat and RV! Featuring 4 Bedrooms plus an offic...

  • 4 Beds
  • 2 Baths
  • Oldsmar Rev Map SubDv.
  • 34677 Zip Code
392 Tavernier Circle, Oldsmar image
392 Tavernier Circle, Oldsmar $558,900 ▼

Welcome Home to this highly sought-after and well established community of The Fountains At Cypress Lakes. MOVE IN READY! Offering Privacy, serenity, and modern upgrade...

  • 3 Beds
  • 2 Baths
  • Fountains At Cypress Lakes Ii-B SubDv.
  • 34677 Zip Code
140 Brent Circle, Oldsmar image
140 Brent Circle, Oldsmar — 140 $565,000 ▼

Seller Motivated! Asking price is under last appraisal value. Come take a look at this beautiful 3 bedroom, 3 bath bay front townhome overlooking Old Tampa Bay and Safet...

  • 3 Beds
  • 3 Baths
  • Seaside Estates SubDv.
  • 34677 Zip Code
1758 Oak Pond Court, Oldsmar image
1758 Oak Pond Court, Oldsmar $575,000 ▼

One or more photo(s) has been virtually staged. WOW! Spacious, great location and something for everyone! From the moment you arrive at 1758 Oak Pond, the 6 bedroom 3 bat...

  • 6 Beds
  • 3 Baths
  • Eastlake Oaks Ph 4 SubDv.
  • 34677 Zip Code
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Simplicity: A Real Estate Brokerage Company

960 Aragon Avenue

Winter Park, FL 32789

Office: 407.378.1900

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