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188 Properties
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188 Properties Available

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  • 347 BAYSHORE DR, Osprey, FL 34229
    3 Beds3 Baths2,216 SqFt
    1/71 71
    Open Fri 4PM-6PM

    $739,000

    347 BAYSHORE DR, Osprey, FL 34229

    Listed by Sharon Sprow COLDWELL BANKER REALTY

    Stellar MLS
  • 156 BISHOPS COURT RD, Osprey, FL 34229
    3 Beds4 Baths3,112 SqFt
    1/84 84
    Open Sun 1PM-3PM

    $1,289,000

    156 BISHOPS COURT RD, Osprey, FL 34229

    Listed by Joel Schemmel DOUGLAS ELLIMAN

    Stellar MLS
  • 97 SUGAR MILL DR, Osprey, FL 34229
    5 Beds6 Baths4,885 SqFt
    1/61 61
    Open Sat 1PM-4PM

    $1,950,000

    97 SUGAR MILL DR, Osprey, FL 34229

    Listed by Maria Domenech PALM PARADISE REALTY GROUP

    Stellar MLS
  • 5100 JESSIE HARBOR DR #304, Osprey, FL 34229
    2 Beds2 Baths2,143 SqFt
    1/71 71
    Open Sun 12:30PM-3PM

    $735,000

    5100 JESSIE HARBOR DR #304, Osprey, FL 34229

    Listed by Suki Scollo COLDWELL BANKER REALTY

    Stellar MLS
  • 353 S SHORE DR, Osprey, FL 34229
    3 Beds2 Baths1,840 SqFt
    1/55 55
    Open Sun 1PM-3PM

    $999,000

    353 S SHORE DR, Osprey, FL 34229

    Listed by Phyllis Coviello COLDWELL BANKER SARASOTA CENT.

    Stellar MLS
  • 403 LONGBOW TRL, Osprey, FL 34229
    4 Beds3 Baths2,770 SqFt
    1/99 99
    Open Sat 1:30PM-3PM

    $1,095,000

    403 LONGBOW TRL, Osprey, FL 34229

    Listed by Edward Bieker, PA DALTON WADE INC

    Stellar MLS
  • 360 N POINT RD, Osprey, FL 34229
    3 Beds4 Baths2,913 SqFt
    1/49 49
    New

    $1,495,000

    360 N POINT RD, Osprey, FL 34229

    Listed by Steve Abbe COLDWELL BANKER REALTY

    Stellar MLS
  • 51 MAC EWEN DR #8, Osprey, FL 34229
    1 Bed1 Bath595 SqFt
    1/14 14
    New

    $2,250

    51 MAC EWEN DR #8, Osprey, FL 34229

    Listed by Deserea Hardy ROSSI & COMPANY INC

    Stellar MLS
  • 1367 THORNAPPLE DR, Osprey, FL 34229
    3 Beds2 Baths2,182 SqFt
    1/60 60
    New

    $579,000

    1367 THORNAPPLE DR, Osprey, FL 34229

    Listed by Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    Stellar MLS
  • 409 N POINT RD #802, Osprey, FL 34229
    3 Beds3 Baths2,055 SqFt
    1/39 39
    New

    $3,900

    409 N POINT RD #802, Osprey, FL 34229

    Listed by Toyia Youtzy JENNETTE PROPERTIES, INC.

    Stellar MLS
  • 184 EXPLORER DR, Osprey, FL 34229
    2 Beds2 Baths1,135 SqFt
    1/21 21
    Active

    $2,150

    184 EXPLORER DR, Osprey, FL 34229

    Listed by Claudia Dybala DALTON WADE INC

    Stellar MLS
  • 4296 EXPEDITION WAY #104, Osprey, FL 34229
    2 Beds2 Baths1,135 SqFt
    1/49 49
    Active

    $299,990

    4296 EXPEDITION WAY #104, Osprey, FL 34229

    Listed by Pamela Kurpiewski EXP REALTY LLC

    Stellar MLS
  • 157 LOOKOUT POINT DR, Osprey, FL 34229
    3 Beds2 Baths1,859 SqFt
    1/73 73
    Active

    $875,000

    157 LOOKOUT POINT DR, Osprey, FL 34229

    Listed by Pat Williams PAT WILLIAMS REALTY, LLC

    Stellar MLS
  • 4212 EXPEDITION WAY, Osprey, FL 34229
    3 Beds2 Baths1,430 SqFt
    1/28 28
    Active

    $2,390

    4212 EXPEDITION WAY, Osprey, FL 34229

    Listed by Claudia Dybala DALTON WADE INC

    Stellar MLS
  • 101 OSPREY POINT DR, Osprey, FL 34229
    4 Beds6 Baths5,087 SqFt
    1/65 65
    Active

    $4,790,000

    101 OSPREY POINT DR, Osprey, FL 34229

    Listed by Joel Schemmel DOUGLAS ELLIMAN

    Stellar MLS
  • 292 TURQUOISE LN, Osprey, FL 34229
    3 Beds2 Baths2,255 SqFt
    1/89 89
    Active

    $1,050,000

    292 TURQUOISE LN, Osprey, FL 34229

    Listed by Steve Abbe COLDWELL BANKER REALTY

    Stellar MLS
  • 314 S SHORE DR, Osprey, FL 34229
    4 Beds3 Baths3,853 SqFt
    1/99 99
    Active

    $1,495,000

    314 S SHORE DR, Osprey, FL 34229

    Listed by Jonathan Minerick HOMECOIN.COM

    Stellar MLS
  • 103 BISHOPS COURT RD, Osprey, FL 34229
    3 Beds2 Baths2,034 SqFt
    1/55 55
    Active

    $749,000

    103 BISHOPS COURT RD, Osprey, FL 34229

    Listed by Mark Lyda GENEROUS PROPERTY

    Stellar MLS
  • 89 NAVIGATION CIR, Osprey, FL 34229
    2 Beds2 Baths1,449 SqFt
    1/61 61
    Active

    $345,000

    89 NAVIGATION CIR, Osprey, FL 34229

    Listed by Jozefina Wells KW COASTAL LIVING II

    Stellar MLS
  • 4424 CONCHFISH LN, Osprey, FL 34229
    4 Beds3 Baths2,370 SqFt
    1/54 54
    Active

    $585,000

    4424 CONCHFISH LN, Osprey, FL 34229

    Listed by Ashley Wallace COLDWELL BANKER REALTY

    Stellar MLS
  • 341 BAYSHORE DR, Osprey, FL 34229
    3 Beds2 Baths1,897 SqFt
    1/45 45
    Active

    $3,150

    341 BAYSHORE DR, Osprey, FL 34229

    Listed by Jeremy Myers COMPASS PROPERTY MANAGEMENT LLC

    Stellar MLS
  • 619 OAK RIVER CT, Osprey, FL 34229
    3 Beds2 Baths2,047 SqFt
    1/42 42
    Pending

    $609,900

    619 OAK RIVER CT, Osprey, FL 34229

    Listed by Ross Fishman FISHMAN GROUP REALTY LLC

    Stellar MLS
  • 272 FOUR KNOT LN, Osprey, FL 34229
    5 Beds3 Baths2,723 SqFt
    1/80 80
    Pending

    $1,095,000

    272 FOUR KNOT LN, Osprey, FL 34229

    Listed by Andrew Peterson KELLER WILLIAMS ISLAND LIFE REAL ESTATE

    Stellar MLS
  • 204 WINDWARD DR, Osprey, FL 34229
    3 Beds3 Baths2,486 SqFt
    1/73 73
    Active

    $1,050,000

    204 WINDWARD DR, Osprey, FL 34229

    Listed by Sharon Lewis GOLF & BAY PROPERTIES LLC

    Stellar MLS
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simpliHŌM

Nicholas Rapisardi License ID: BK3229484

+1(941) 735-0244 nicholas@simplihom.com

3859 Bee Ridge Rd | Suite 102 | Sarasota FL | 34233

Realtor: Nicholas V Rapisardi PLLC

Broker: Nicholas V Rapisardi

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      Home
      Buy
      1. All Listings
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      Sell
      1. Price Estimate
      2. Selling Vocab
      Book a Call
      About
      1. About Us
      2. Meet Nicholas
      3. The Brokerage
      4. Join Us
simpliHŌM

Nicholas Rapisardi License ID: BK3229484

+1(941) 735-0244 nicholas@simplihom.com

3859 Bee Ridge Rd | Suite 102 | Sarasota FL | 34233

Realtor: Nicholas V Rapisardi PLLC

Broker: Nicholas V Rapisardi

Get My App

Terms of Service & Privacy Policy | Cookie Policy | Cookie Preferences | Property Listings | Sitemap | Accessibility

Powered by Lofty Inc. Copyright 2026. All Rights Reserved.

IDX information is provided exclusively for consumers’ personal, non-commercial use and that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed to be accurate. Listing information updated daily.