27 total properties
Did you mean the neighborhood Osprey?
View 6100 JESSIE HARBOR DRIVE 603 Osprey, FL MLS# A4676824
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1 of 43
OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
$899,000
3

Beds

3.0

Baths

2,630

Sq.Ft.

6100 JESSIE HARBOR DRIVE 603

Osprey, FL

Courtesy of ENGEL + VOELKERS SARASOTA
View 616 CRANE PRAIRIE WAY Osprey, FL MLS# N6142165
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1 of 56
$960,000
3

Beds

4.0

Baths

3,561

Sq.Ft.

616 CRANE PRAIRIE WAY

Osprey, FL

Courtesy of KELLER WILLIAMS ISLAND LIFE REAL ESTATE
View 678 FAITH AVENUE Osprey, FL MLS# A4674865
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1 of 51
$990,000
3

Beds

3.0

Baths

2,583

Sq.Ft.

678 FAITH AVENUE

Osprey, FL

Courtesy of GENEROUS PROPERTY
The time to sell is now! THE TIME TO SELL IS NOW!
View 3983 DESTINATION DRIVE 102 Osprey, FL MLS# TB8455523
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1 of 22
$1,050,000
2,030

Sq.Ft.

3983 DESTINATION DRIVE 102

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 172 SEA ANCHOR DRIVE Osprey, FL MLS# A4671745
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1 of 48
OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
$936,000
3

Beds

3.0

Baths

2,283

Sq.Ft.

172 SEA ANCHOR DRIVE

Osprey, FL

Courtesy of GOLF & BAY PROPERTIES LLC
View 3936 WAYPOINT AVENUE Osprey, FL MLS# A4670043
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1 of 76
$1,089,000
3

Beds

3.0

Baths

2,323

Sq.Ft.

3936 WAYPOINT AVENUE

Osprey, FL

Courtesy of CORCORAN DWELLINGS REALTY
View 1486 LANDVIEW LANE Osprey, FL MLS# D6144630
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1 of 78
$995,000
3

Beds

2.0

Baths

1,869

Sq.Ft.

1486 LANDVIEW LANE

Osprey, FL

Courtesy of EXP REALTY LLC
View 238 LOOKOUT POINT DRIVE Osprey, FL MLS# A4671468
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1 of 66
OPEN HOUSE: Sunday 1/11 1:00 PM - 4:00 PM
$895,000
3

Beds

2.1

Baths

2,676

Sq.Ft.

238 LOOKOUT POINT DRIVE

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 6100 JESSIE HARBOR DRIVE 202 Osprey, FL MLS# A4670353
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1 of 87
$970,000
3

Beds

3.1

Baths

3,771

Sq.Ft.

6100 JESSIE HARBOR DRIVE 202

Osprey, FL

Courtesy of GULF SANDS REALTY, LLC
View 327 PARK TRACE BOULEVARD Osprey, FL MLS# A4670046
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1 of 42
OPEN HOUSE: Sunday 1/11 1:00 PM - 3:00 PM
$879,000
4

Beds

3.0

Baths

2,935

Sq.Ft.

327 PARK TRACE BOULEVARD

Osprey, FL

Courtesy of MICHAEL SAUNDERS & COMPANY
View 903 TRANQUILITY CIRCLE Osprey, FL MLS# A4669102
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1 of 39
$879,000
3

Beds

3.0

Baths

2,622

Sq.Ft.

903 TRANQUILITY CIRCLE

Osprey, FL

Courtesy of GENEROUS PROPERTY
View 392 PARK TRACE BOULEVARD Osprey, FL MLS# A4668610
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1 of 38
$939,000
4

Beds

3.0

Baths

2,802

Sq.Ft.

392 PARK TRACE BOULEVARD

Osprey, FL

Courtesy of COLDWELL BANKER REALTY
View 242 HIDDEN BAY DRIVE 401 Osprey, FL MLS# D6143964
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1 of 62
$875,000
3

Beds

3.0

Baths

2,100

Sq.Ft.

242 HIDDEN BAY DRIVE 401

Osprey, FL

Courtesy of LASBURY-TRACY REALTY INC.
View 38 W BAY STREET Osprey, FL MLS# A4667010
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1 of 60
$899,000
3

Beds

2.0

Baths

2,124

Sq.Ft.

38 W BAY STREET

Osprey, FL

Courtesy of HARRY ROBBINS ASSOC INC
View 3957 WAYPOINT AVENUE Osprey, FL MLS# A4666325
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1 of 24
$925,000
3

Beds

3.0

Baths

2,328

Sq.Ft.

3957 WAYPOINT AVENUE

Osprey, FL

Courtesy of RE/MAX ALLIANCE GROUP
View 123 WINDWARD DRIVE Osprey, FL MLS# A4656319
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Save 123 WINDWARD DRIVE Osprey, FL MLS# A4656319
1 of 77
OPEN HOUSE: Sunday 1/11 1:00 PM - 4:00 PM
$820,000
3

Beds

2.0

Baths

1,894

Sq.Ft.

123 WINDWARD DRIVE

Osprey, FL

Courtesy of WILLIAM RAVEIS REAL ESTATE
View 21 BAYHEAD LANE Osprey, FL MLS# A4664085
    Save 21 BAYHEAD LANE Osprey, FL MLS# A4664085
    1 of 92
    $900,000
    3

    Beds

    2.0

    Baths

    2,216

    Sq.Ft.

    21 BAYHEAD LANE

    Osprey, FL

    Courtesy of COLDWELL BANKER REALTY
    View 701 EAGLENOOK WAY Osprey, FL MLS# A4663832
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    1 of 65
    $1,025,000
    4

    Beds

    4.1

    Baths

    3,533

    Sq.Ft.

    701 EAGLENOOK WAY

    Osprey, FL

    Courtesy of COLDWELL BANKER SARASOTA CENT.
    View 1602 SOUTHBAY DRIVE Osprey, FL MLS# A4665288
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    1 of 56
    OPEN HOUSE: Sunday 1/11 2:00 PM - 4:00 PM
    $999,995
    4

    Beds

    3.1

    Baths

    2,980

    Sq.Ft.

    1602 SOUTHBAY DRIVE

    Osprey, FL

    Courtesy of COMPASS FLORIDA LLC
    View 599 PINE RANCH EAST ROAD Osprey, FL MLS# A4660895
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    Save 599 PINE RANCH EAST ROAD Osprey, FL MLS# A4660895
    1 of 43
    $949,000
    3

    Beds

    2.0

    Baths

    2,188

    Sq.Ft.

    599 PINE RANCH EAST ROAD

    Osprey, FL

    Courtesy of GENEROUS PROPERTY

    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

    168

    Estimated median home price

    $795,000
    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 - 100K3
    $100K - 200K11
    $200K - 300K9
    $300K - 400K9
    $400K - 500K8
    $500K - 600K11
    $600K - 700K22
    $700K - 800K14
    $800K - 900K12
    $900K - 1M11
    $1M - Max58

    Homes for Sale by Type in Osprey, FL

    Property TypeCount
    Single Family99
    Townhouse3
    Condo47
    Commercial6
    Rental35
    Lots and Land7
    Condo/Town/CoOp0
    CoOp0
    Multi Family0
    Mobile Home6
    Farms0

    (Data as of 1/9/2026)

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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 1/10/2026.