153 total properties
Did you mean the neighborhood Osprey?
View 436 S TAMIAMI TRAIL C4 Osprey, FL MLS# A4648348
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1 of 44
$350,000
1,272

Sq.Ft.

436 S TAMIAMI TRAIL C4

Osprey, FL

Courtesy of KONA REALTY
View 2251 JESSIE HARBOR DRIVE 2101 Osprey, FL MLS# A4631433
    Save 2251 JESSIE HARBOR DRIVE 2101 Osprey, FL MLS# A4631433
    1 of 62
    $349,000
    2

    Beds

    2.0

    Baths

    1,400

    Sq.Ft.

    2251 JESSIE HARBOR DRIVE 2101

    Osprey, FL

    Courtesy of GENEROUS PROPERTY
    View 89 NAVIGATION CIRCLE Osprey, FL MLS# A4694435
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    1 of 61
    $345,000
    2

    Beds

    2.0

    Baths

    1,449

    Sq.Ft.

    89 NAVIGATION CIRCLE

    Osprey, FL

    Courtesy of KW COASTAL LIVING II
    The time to sell is now! THE TIME TO SELL IS NOW!
    View 4304 EXPEDITION WAY WAY 105 Osprey, FL MLS# N6143250
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    1 of 77
    $328,000
    3

    Beds

    2.0

    Baths

    1,528

    Sq.Ft.

    4304 EXPEDITION WAY WAY 105

    Osprey, FL

    Courtesy of EXIT KING REALTY
    View 4284 EXPEDITION WAY NA Osprey, FL MLS# A4681835
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    1 of 40
    $325,000
    3

    Beds

    2.0

    Baths

    1,430

    Sq.Ft.

    4284 EXPEDITION WAY NA

    Osprey, FL

    Courtesy of PREFERRED SHORE LLC
    View 1801 HIGHLAND ROAD Osprey, FL MLS# N6140508
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      1 of 41
      $299,900
      2

      Beds

      2.0

      Baths

      1,165

      Sq.Ft.

      1801 HIGHLAND ROAD

      Osprey, FL

      Courtesy of RE/MAX ALLIANCE GROUP
      View 4226 FRONTIER LANE 103 Osprey, FL MLS# A4687965
        Save 4226 FRONTIER LANE 103 Osprey, FL MLS# A4687965
        1 of 36
        $299,000
        2

        Beds

        2.0

        Baths

        1,135

        Sq.Ft.

        4226 FRONTIER LANE 103

        Osprey, FL

        Courtesy of COLDWELL BANKER REALTY
        View 184 EXPLORER DRIVE Osprey, FL MLS# A4692249
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        1 of 30
        $294,900
        2

        Beds

        2.0

        Baths

        1,244

        Sq.Ft.

        184 EXPLORER DRIVE

        Osprey, FL

        Courtesy of DALTON WADE INC
        View 4173 FRONTIER LANE 4173 Osprey, FL MLS# A4689582
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        1 of 51
        $289,000
        2

        Beds

        2.0

        Baths

        1,135

        Sq.Ft.

        4173 FRONTIER LANE 4173

        Osprey, FL

        Courtesy of KELLER WILLIAMS ON THE WATER S
        View 51 MAC EWEN DRIVE 14 Osprey, FL MLS# A4690371
          Save 51 MAC EWEN DRIVE 14 Osprey, FL MLS# A4690371
          1 of 19
          $285,000
          1

          Beds

          1.0

          Baths

          595

          Sq.Ft.

          51 MAC EWEN DRIVE 14

          Osprey, FL

          Courtesy of COLDWELL BANKER REALTY
          View 4271 EXPEDITION WAY 103 Osprey, FL MLS# A4689541
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          1 of 35
          $280,000
          2

          Beds

          2.0

          Baths

          1,135

          Sq.Ft.

          4271 EXPEDITION WAY 103

          Osprey, FL

          Courtesy of KW COASTAL LIVING III
          View 51 MACEWEN DRIVE 12 Osprey, FL MLS# A4690540
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          1 of 71
          $275,000
          1

          Beds

          1.0

          Baths

          623

          Sq.Ft.

          51 MACEWEN DRIVE 12

          Osprey, FL

          Courtesy of COLDWELL BANKER REALTY
          View 222 GLENWOOD AVENUE Osprey, FL MLS# TB8504427
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          1 of 53
          $275,000
          2

          Beds

          2.0

          Baths

          952

          Sq.Ft.

          222 GLENWOOD AVENUE

          Osprey, FL

          Courtesy of JAY ALAN REAL ESTATE
          View 456 WASHINGTON AVENUE Osprey, FL MLS# A4623594
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          1 of 7
          $269,999
          Studio

          Beds

          0.0

          Baths

          456 WASHINGTON AVENUE

          Osprey, FL

          Courtesy of FLOTACAL
          View 754 PINE RUN DRIVE 754 Osprey, FL MLS# A4693150
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          1 of 45
          OPEN HOUSE: Saturday 5/23 1:00 PM - 4:00 PM
          $269,000
          2

          Beds

          2.0

          Baths

          1,379

          Sq.Ft.

          754 PINE RUN DRIVE 754

          Osprey, FL

          Courtesy of CALL IT CLOSED INTL REALTY
          View 232 WOODLAND DRIVE 232 Osprey, FL MLS# A4671600
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          1 of 47
          $259,900
          2

          Beds

          2.0

          Baths

          1,325

          Sq.Ft.

          232 WOODLAND DRIVE 232

          Osprey, FL

          Courtesy of PAT WILLIAMS REALTY, LLC
          View 51 MACEWEN DRIVE 11 Osprey, FL MLS# A4679180
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          1 of 42
          $235,000
          1

          Beds

          1.0

          Baths

          623

          Sq.Ft.

          51 MACEWEN DRIVE 11

          Osprey, FL

          Courtesy of 342 REAL ESTATE
          View 51 MACEWEN DRIVE 5 Osprey, FL MLS# A4689838
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          1 of 44
          $235,000
          1

          Beds

          1.0

          Baths

          595

          Sq.Ft.

          51 MACEWEN DRIVE 5

          Osprey, FL

          Courtesy of 342 REAL ESTATE
          View SARABAY ROAD Osprey, FL MLS# A4690459
            Save SARABAY ROAD Osprey, FL MLS# A4690459
            1 of 6
            $225,000
            Studio

            Beds

            0.0

            Baths

            SARABAY ROAD

            Osprey, FL

            Courtesy of MICHAEL SAUNDERS & COMPANY
            View 252 SUN AIR CIRCLE Osprey, FL MLS# A4683143
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            1 of 86
            $215,000
            2

            Beds

            2.0

            Baths

            1,152

            Sq.Ft.

            252 SUN AIR CIRCLE

            Osprey, FL

            Courtesy of COLDWELL BANKER SARASOTA CENT.

            About Osprey

            The most northern of the Venice communities is Osprey, harmonizing older neighborhoods with an elegant golf-course development.  The recreational attractions of Oscar Scherer State Park and Historic Spanish Point enable this area to preserve its natural beauty.  Whether you like shopping in the unique stores of the downtown Venice Main Street district or prefer golfing, boating, fishing, or just laying on the beach; the five community area of Osprey, Laurel, Nokomis, Venice and South Venice offers a little bit of everything.

            Listings in Osprey, FL

            175

            Estimated median home price

            $719,000
            Osprey FL Homes for Sale & Properties

            Weichert Realtors is one of the nation's leading providers of Osprey, Florida real estate for sale and home ownership services. Contact Weichert today to buy or sell real estate in Osprey, FL.

            Homes for Sale by Price in Osprey, FL

            PriceCount
            $0 - 100K5
            $100K - 200K8
            $200K - 300K15
            $300K - 400K7
            $400K - 500K12
            $500K - 600K15
            $600K - 700K25
            $700K - 800K14
            $800K - 900K10
            $900K - 1M6
            $1M - Max58

            Homes for Sale by Type in Osprey, FL

            Property TypeCount
            Single Family93
            Townhouse5
            Condo61
            Commercial4
            Rental31
            Lots and Land8
            Condo/Town/CoOp0
            CoOp0
            Multi Family0
            Mobile Home4
            Farms0

            (Data as of 5/23/2026)

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            Information deemed reliable but not guaranteed.

            Listing information courtesy of My Florida Regional MLS DBA Stellar MLS. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumer personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law.

            Copyright 2012 My Florida Regional MLS DBA Stellar MLS. All rights reserved

            Data is updated as of 5/23/2026.