10,688

Oldsmar, FL Homes

Section Image
  • /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 $527,243

    Last Listing Agent Alecia Savas COLDWELL BANKER REALTY

    4874 Westchester Ct, Oldsmar, FL 34677
    • /27

      Est $282,702

      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

      • 75 Days On Market

      Last Listing Agent Raul Rivera CHARLES RUTENBERG REALTY INC

  • /57

    $189,999

    $9K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,096 Sq Ft

    130 Nancy Dr Unit 37, Oldsmar, FL 34677

    "RESORT STYLE LIVING" in East Lake Woodlands! This beautifully maintained 2-bedroom,2-bath condominium offers approximately 1,151 sq ft of comfortable living space in one of Oldsmar’s most desirable gated communities. Major updates provide peace of mind, including flooring, A/C system, hot water heater, dishwasher, washer and dryer, and bedroom carpeting all approximately 3 years old, plus a

    Steve DeMatos RE/MAX ALLIANCE GROUP

    130 Nancy Dr Unit 37, 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 $445,274

    Last Listing Agent Amanda Lebiszczak CHARLES RUTENBERG REALTY INC

    505 Oakwood Blvd, Oldsmar, FL 34677
    • /2

      Est $289,702

      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

      • 7 Days On Market

      Last Listing Agent Terri Harrington VUE REALTY, LLC

  • /31

    $165,000

    $30K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,128 Sq Ft

    278 Pelican Dr N, Oldsmar, FL 34677

    Don't miss this desirable and very active community of Gull-Aire Village! This is one of the most highly sought-after 55+ communities in Pinellas County. With HOA fees at only $60/mo and the ability to rent out your home after only 1 year of ownership, the possibilities are endless. This home includes a rare LARGE GARAGE! You own your own land. The owner has just replaced the range and

    Jon Dant RE/MAX ACTION FIRST OF FLORIDA

    278 Pelican Dr N, 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 $590,778

    Last Listing Agent Candice Kelly IAD REAL ESTATE

    422 Cypress View Dr, Oldsmar, FL 34677
    • /2

      Est $365,871

      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

      • 71 Days On Market

      Last Listing Agent Yanya McReynolds PEOPLE'S TRUST REALTY

  • /43

    $325,000

    • 3 Beds
    • 1 Bath
    • 924 Sq Ft

    650 Timber Bay Cir W, Oldsmar, FL 34677

    CHARMING 3 bed, 1 bath impeccable home in downtown Oldsmar area. NEW interior doors, NEW stove, NEW baseboards, NEW bathroom vanity, lighting, mirror,, NEW remote control ceiling fans with lights, NEW carriage lights (front and back) NEW GFCI outlets, NEW paint interior, exterior, NEW paint garage, patio, NEWER windows and slider with integral blinds (2023, 2026), HWH 2025, DISHWASHER 2023,

    Ginger Tatarzewski FUTURE HOME REALTY INC

    650 Timber Bay Cir W, Oldsmar, FL 34677
  • /2

    $199,000

    Sold Nov 21, 2025

    313 Jefferson Ave S, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,271 Sq Ft
    • Built 1940

    Last Sold Summary

    • 43% Below List Price
    • $157/SF
    • 217 Days On Market

    Current Estimated Value $424,622

    Last Listing Agent Aaron Bedy RMS ELITE PROPERTIES

    313 Jefferson Ave S, Oldsmar, FL 34677
    • /56

      Est $331,704

      Not Listed For Sale

      50 Ashley Ln, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,745 Sq Ft
      • Built 1981
      50 Ashley Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 2 Days On Market

      Last Listing Agent William Lagattolla ONE PROPERTIES INTL PLLC

  • /17

    $220,000

    $5K PRICE DROP
    • 1 Bed
    • 1 Bath
    • 1,024 Sq Ft

    2034 Montego Ct, Oldsmar, FL 34677

    Welcome to this spacious 1,028 sq ft villa in the desirable Bayside Meadows community of Oldsmar. This beautifully updated home offers the comfort and privacy of villa living with a one-car garage, fenced backyard, and screened lanai—perfect for enjoying Florida’s year-round outdoor lifestyle.The thoughtfully designed interior features a kitchen overlooking the living area, a cozy

    Jerry Hills RE/MAX ELITE REALTY

    2034 Montego Ct, 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 $346,542

    Last Listing Agent David Weylie ELITE TAMPA BAY REALTY LLC

    504 Cabernet Way, Oldsmar, FL 34677
    • /39

      Est $329,722

      Not Listed For Sale

      210 Balsam Dr, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,795 Sq Ft
      • Built 1981
      210 Balsam Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 12 Days On Market

      Last Listing Agent Matt Generose THE SOMERDAY GROUP PL

  • /43

    $118,900

    $11K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 915 Sq Ft

    123 Loblolly Ct Unit B, Oldsmar, FL 34677

    Virtually Staged. GROUND FLOOR ~ NON - FLOOD ZONE. 2 Bedrooms, 2 Bathroom and move in ready in the heart of Oldsmar! Community amenities include a pool, playground, basketball court, tennis courts and beautiful lake with a dock! Bring your fishing pole. Freshly painted and move-in ready, tile floor throughout, making it an ideal canvas for a buyer looking to add personal touches and build equity.

    Christina Paolillo CHARLES RUTENBERG REALTY INC

    123 Loblolly Ct Unit B, 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 $153,990

    Last Listing Agent Thomas Byrnes EXP REALTY LLC

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

      Est $290,483

      Not Listed For Sale

      60 Balsam Dr, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,250 Sq Ft
      • Built 1981
      60 Balsam Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Jennifer Bilodeau LPT REALTY, LLC

  • /20

    $345,000

    • 3 Beds
    • 2.5 Baths
    • 1,392 Sq Ft

    103 Cutlass Way, Oldsmar, FL 34677

    Welcome to this impeccably maintained 3 bedroom, 2.5 bath residence in the highly sought-after Hayes Park Village in Oldsmar. Offering approximately 1,392 square feet of thoughtfully designed living space, this home showcases a beautifully renovated kitchen with contemporary finishes, ceramic flooring on the first floor, and carpet flooring on the second floor. The split-bedroom floor plan and

    Leyla Mohebbi FLORIDA COMMERCIAL GROUP

    103 Cutlass Way, 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 $147,042

    Last Listing Agent Jessica Scialletti URBAN REAL ESTATE US

    500 Federal St, Oldsmar, FL 34677
    • /2

      Est $328,986

      Not Listed For Sale

      50 Balsam Dr, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,450 Sq Ft
      • Built 1981
      50 Balsam Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 30 Days On Market

      Last Listing Agent David Timmons KELLER WILLIAMS REALTY- PALM HARBOR

  • /87

    $319,000

    $6K PRICE DROP Pending
    • 3 Beds
    • 2 Baths
    • 1,385 Sq Ft

    180 Ingrid Place, Oldsmar, FL 34677

    Under contract-accepting backup offers. Don’t miss this wonderful opportunity to own a maintenance free villa in the beautiful East Lake Woodlands Community. This 3 bedroom home is a corner unit that has an open floor plan, split bedrooms with an huge lanai with outstanding tranquil views. Large master bedroom has a walk in closet and bath with nicely tiled shower. New tankless hot water heater.

    Donna Green OZONA REALTY

    180 Ingrid Place, Oldsmar, FL 34677
  • /2

    $135,000

    Sold May 22, 2026

    134 Cypress Ct Unit 134, Oldsmar, FL 34677

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

    Last Sold Summary

    • 18% Below List Price
    • $128/SF
    • 58 Days On Market

    Current Estimated Value $142,109

    Last Listing Agent Vanessa Leonard KELLER WILLIAMS REALTY- PALM HARBOR

    134 Cypress Ct Unit 134, Oldsmar, FL 34677
    • /2

      Est $318,543

      Not Listed For Sale

      190 Poole Place, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft
      • Built 1979
      190 Poole Place, Oldsmar, FL 34677

      Last Sold Summary

      • 60 Days On Market

      Last Listing Agent Bill Lewis BHHS FLORIDA PROPERTIES GROUP

  • /48

    $198,500

    $51K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,080 Sq Ft

    347 Canal Way, Oldsmar, FL 34677

    Welcome to Gull-Aire Village, a 55+ PET-Friendly and Golf Cart Friendly community in the Heart of Oldsmar! Gull-Aire Village is a Land-Owned community, meaning YOU OWN THE LAND! not just the home. A Very unique property with No rear neighbors. This home comes FULLY FURNISHED! and Features A NEWER ROOF (only 3yrs Old) Newer WINDOWS and Doors, New Flooring(2025) and Vapor Barrier (2025) New Water

    Asher Walli CHARLES RUTENBERG REALTY INC

    347 Canal Way, 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 $442,481

    Last Listing Agent Amy Denham COASTAL PROPERTIES GROUP INTERNATIONAL

    1630 Gray Bark Dr, Oldsmar, FL 34677
    • /45

      Est $359,419

      Not Listed For Sale

      80 Poole Place, Oldsmar, FL 34677

      • 4 Beds
      • 2 Baths
      • 1,550 Sq Ft
      • Built 1979
      80 Poole Place, Oldsmar, FL 34677

      Last Sold Summary

      • 68 Days On Market

      Last Listing Agent Jessica Carlson CENTURY 21 BEGGINS ENTERPRISES

  • /24

    $259,900

    $70K PRICE INCREASE
    • 2 Beds
    • 2 Baths
    • 1,064 Sq Ft

    704 Lemonwood Dr, Oldsmar, FL 34677

    Investor special with exceptional upside! This concrete block 2-bedroom, 2-bath, 2-car garage home is priced to sell and offers outstanding renovation potential. Situated on a nicely sized lot with beautiful lake views and no rear neighbors, the fully fenced backyard has plenty of room for a pool. The home has an updated electrical panel. The HVAC system was updated in 2019. The roof was last

    Johnny Mead DALTON WADE INC

    704 Lemonwood Dr, Oldsmar, FL 34677
  • /2

    $369,500

    Sold Jun 16, 2026

    1820 Driftwood Cir N, Oldsmar, FL 34677

    • 3 Beds
    • 2 Baths
    • 1,528 Sq Ft
    • Built 1973

    Last Sold Summary

    • 5% Below List Price
    • $242/SF
    • 158 Days On Market

    Current Estimated Value $381,892

    Last Listing Agent Frank Acerra SELECT PROPERTIES INC

    1820 Driftwood Cir N, Oldsmar, FL 34677
    • /2

      Est $289,619

      Not Listed For Sale

      100 Sylvia Place, Oldsmar, FL 34677

      • 4 Beds
      • 2 Baths
      • 1,550 Sq Ft
      • Built 1978
      100 Sylvia Place, Oldsmar, FL 34677

      Last Sold Summary

      • 14 Days On Market

      Last Listing Agent Cathy McCarthy RE/MAX REALTEC GROUP INC

  • /42

    $279,900

    $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,755 Sq Ft

    110 Ingrid Place, Oldsmar, FL 34677

    Nature lovers! Enjoy the abundant wildlife and tranquil creek/preserve views from the patio and 2nd floor balcony of this fabulous townhome nestled in the heart of East Lake Woodlands, among the premier gated country club communities in northern Pinellas County! The primary suite—created by combining what was originally two bedrooms—feels exceptionally spacious, with plenty of room to unwind, and

    Rene Mailaender RE/MAX REALTEC GROUP INC

    110 Ingrid Place, 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 $257,741

    Last Listing Agent Tabitha Clark EXP REALTY LLC

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

      Est $269,615

      Not Listed For Sale

      460 S Woodlands Dr, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,300 Sq Ft
      • Built 1979
      460 S Woodlands Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 92 Days On Market

      Last Listing Agent Jared Rutherford KELLER WILLIAMS TAMPA PROPERTIES

  • /31

    $300,000

    Pending
    • 2 Beds
    • 2 Baths
    • 1,700 Sq Ft

    1224 Clays Trail, Oldsmar, FL 34677

    INCREDIBLE GOLF COUSE VIEW CERTIFIED PRE-OWNED HOME IN DESIREABLE COMMUNITY OF EAST LAKE WOODLANDS ! This is a Certified Pre-Owned Home -- and that changes everything. Before you ever make an offer, a licensed home inspector has already been through this home top to bottom. You get the full report at no cost it feature a 2022 water Heater, 2024 HVAC. No surprises. No guessing. Just confidence.

    Yamil Winn YOUR HOME SOLD GUARANTEED REALTY

    1224 Clays Trail, 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 $628,181

    Last Listing Agent Heather Viviano RE/MAX REALTEC GROUP INC

    5163 Pinnacle Dr, Oldsmar, FL 34677
    • /29

      Est $315,582

      Not Listed For Sale

      420 S Woodlands Dr, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,330 Sq Ft
      • Built 1979
      420 S Woodlands Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 46 Days On Market

      Last Listing Agent Chase Crawford SPARROW KEY REALTY INC

  • /34

    $437,500

    $20K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,888 Sq Ft

    1309 Sunset Wind Loop, Oldsmar, FL 34677

    Welcome to this beautifully maintained 3-bedroom, 2.5-bath townhome (NEVER FLOODED) in one of Oldsmars most desirable waterfront gated communities. This move-in-ready home offers comfort, convenience and low-maintenance resort style living. The open-concept layout is designed for both everyday comfort and effortless entertaining, featuring a spacious living and dining area filled with natural

    Anabel Ottersbach DALTON WADE INC

    1309 Sunset Wind Loop, 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 $192,831

    Last Listing Agent Bob McCaffery BHHS FLORIDA PROPERTIES GROUP

    106 Camille Ct, Oldsmar, FL 34677
    • /25

      Est $380,545

      Not Listed For Sale

      330 S Woodlands Dr, Oldsmar, FL 34677

      • 2 Beds
      • 2 Baths
      • 1,710 Sq Ft
      • Built 1979
      330 S Woodlands Dr, Oldsmar, FL 34677

      Last Sold Summary

      • 33 Days On Market

      Last Listing Agent Matthew Walker COLDWELL BANKER REALTY

  • /2

    $215,000

    Sold Aug 29, 2025

    105 Woodlake Wynde, Oldsmar, FL 34677

    • 2 Beds
    • 2 Baths
    • 924 Sq Ft
    • Built 1983

    Last Sold Summary

    • 6% Below List Price
    • $233/SF
    • 81 Days On Market

    Current Estimated Value $199,223

    Last Listing Agent Frank Acerra SELECT PROPERTIES INC

    105 Woodlake Wynde, Oldsmar, FL 34677
    • /2

      Est $327,012

      Not Listed For Sale

      340 Lisa Ln, Oldsmar, FL 34677

      • 3 Beds
      • 2 Baths
      • 1,730 Sq Ft
      • Built 1978
      340 Lisa Ln, Oldsmar, FL 34677

      Last Sold Summary

      • 158 Days On Market

      Last Listing Agent Darlene Sheets FUTURE HOME REALTY INC

Showing Results 641 - 680, Page 17 of 18

How to Buy a Home How to Finance a Home How to Sell a Home