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176 Properties
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176 Properties Available In 34229

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FL >34229 >
Market Insights
  • 2309 JESSIE HARBOR DR #2402, Osprey, FL 34229
    3 Beds3 Baths2,006 SqFt
    3D
    Open Fri 2PM-4PM

    $497,000

    2309 JESSIE HARBOR DR #2402, Osprey, FL 34229

    Listed by Christine Pope MICHAEL SAUNDERS & COMPANY

    Stellar MLS
  • 6100 JESSIE HARBOR DR #202, Osprey, FL 34229
    3 Beds4 Baths3,771 SqFt
    1/83 83
    Open Sun 1PM-3PM

    $850,000

    6100 JESSIE HARBOR DR #202, Osprey, FL 34229

    Listed by Angelic Tassos CORCORAN DWELLINGS REALTY

    Stellar MLS
  • 916 MACEWEN DR, Osprey, FL 34229
    5 Beds8 Baths5,986 SqFt
    1/97 97
    New

    $1,900,000

    916 MACEWEN DR, Osprey, FL 34229

    Listed by Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    Stellar MLS
  • 14041 BELLAGIO WAY #214, Osprey, FL 34229
    3 Beds2 Baths1,799 SqFt
    1/51 51
    New

    $6,000

    14041 BELLAGIO WAY #214, Osprey, FL 34229

    Listed by Veronica Lee COLDWELL BANKER REALTY

    Stellar MLS
  • 903 TRANQUILITY CIR, Osprey, FL 34229
    3 Beds3 Baths2,622 SqFt
    3D
    Active Under Contract

    $739,900

    903 TRANQUILITY CIR, Osprey, FL 34229

    Listed by Carolyn Yates COLDWELL BANKER SARASOTA CENT.

    Stellar MLS
  • 956 SCHERER WAY, Osprey, FL 34229
    4 Beds3 Baths2,290 SqFt
    1/58 58
    New

    $4,800

    956 SCHERER WAY, Osprey, FL 34229

    Listed by Benjamin Schwab KEYRENTER SARASOTA PROPERTY MANAGEMENT

    Stellar MLS
  • 4401 CONCHFISH LN, Osprey, FL 34229
    4 Beds3 Baths2,370 SqFt
    1/27 27
    New

    $3,595

    4401 CONCHFISH LN, Osprey, FL 34229

    Listed by Klara Mrcela COMPASS FLORIDA, LLC

    Stellar MLS
  • 486 YACHT HARBOR DR, Osprey, FL 34229
    3 Beds4 Baths2,939 SqFt
    1/75 75
    Pending

    $1,400,000

    486 YACHT HARBOR DR, Osprey, FL 34229

    Listed by Pat Williams PAT WILLIAMS REALTY, LLC

    Stellar MLS
  • 701 PINE RUN DR #701, Osprey, FL 34229
    1 Bed1 Bath586 SqFt
    Coming Soon

    $172,000

    701 PINE RUN DR #701, Osprey, FL 34229

    Listed by Pat Williams PAT WILLIAMS REALTY, LLC

    Stellar MLS
  • 780 SARABAY RD #16, Osprey, FL 34229
    2 Beds2 Baths1,574 SqFt
    1/54 54
    Active

    $425,000

    780 SARABAY RD #16, Osprey, FL 34229

    Listed by Mark Segreto RMS ELITE PROPERTIES

    Stellar MLS
  • 137 NAVIGATION CIR, Osprey, FL 34229
    3 Beds2 Baths1,430 SqFt
    1/26 26
    Active

    $2,000

    137 NAVIGATION CIR, Osprey, FL 34229

    Listed by Alexandra Stella PMI SOUTHWEST FLORIDA

    Stellar MLS
  • 120 WOODLAND PL #120, Osprey, FL 34229
    2 Beds2 Baths1,325 SqFt
    1/65 65
    Active Under Contract

    $299,000

    120 WOODLAND PL #120, Osprey, FL 34229

    Listed by Kim Kruysman EXP REALTY LLC

    Stellar MLS
  • 108 WOODLAND PL #108, Osprey, FL 34229
    2 Beds2 Baths1,316 SqFt
    1/50 50
    Active

    $285,000

    108 WOODLAND PL #108, Osprey, FL 34229

    Listed by Pat Williams PAT WILLIAMS REALTY, LLC

    Stellar MLS
  • 329 BAY VISTA AVE, Osprey, FL 34229
    2 Beds2 Baths1,346 SqFt
    1/30 30
    Active

    $429,000

    329 BAY VISTA AVE, Osprey, FL 34229

    Listed by Rodrigo Posada THE SHORELINE FL REALTY LLC

    Stellar MLS
  • 534 OAK BAY DR, Osprey, FL 34229
    4 Beds3 Baths2,077 SqFt
    1/41 41
    Active

    $3,800

    534 OAK BAY DR, Osprey, FL 34229

    Listed by Brian ODonnell REALTY BY DESIGN LLC

    Stellar MLS
  • Osprey, FL 34229
    4 Beds3 Baths2,607 SqFt
    1/45 45
    Active

    $799,000

    Osprey, FL 34229

    Listed by Claudia Dybala DALTON WADE INC

    Stellar MLS
  • 2251 JESSIE HARBOR DR #2101, Osprey, FL 34229
    2 Beds2 Baths1,400 SqFt
    3D
    Active Under Contract

    $359,000

    2251 JESSIE HARBOR DR #2101, Osprey, FL 34229

    Listed by Mike Martino KELLER WILLIAMS ON THE WATER S

    Stellar MLS
  • 4213 EXPEDITION WAY #107, Osprey, FL 34229
    3 Beds2 Baths1,430 SqFt
    1/39 39
    Active

    $320,000

    4213 EXPEDITION WAY #107, Osprey, FL 34229

    Listed by Yunfei Liu DALTON WADE INC

    Stellar MLS
  • 919 SCHERER WAY, Osprey, FL 34229
    4 Beds3 Baths2,290 SqFt
    1/45 45
    Active

    $4,000

    919 SCHERER WAY, Osprey, FL 34229

    Listed by Jeremy Myers COMPASS PROPERTY MANAGEMENT LLC

    Stellar MLS
  • 6100 JESSIE HARBOR DR #202, Osprey, FL 34229
    3 Beds4 Baths3,771 SqFt
    1/65 65
    Active

    $5,500

    6100 JESSIE HARBOR DR #202, Osprey, FL 34229

    Listed by Angelic Tassos CORCORAN DWELLINGS REALTY

    Stellar MLS
  • 321 LOOKOUT POINT DR, Osprey, FL 34229
    3 Beds4 Baths3,122 SqFt
    1/77 77
    Pending

    $3,100,000

    321 LOOKOUT POINT DR, Osprey, FL 34229

    Listed by Steve Abbe COLDWELL BANKER REALTY

    Stellar MLS
  • 429 PATTERSON AVE, Osprey, FL 34229
    3 Beds1 Bath1,173 SqFt
    1/46 46
    Active Under Contract

    $449,000

    429 PATTERSON AVE, Osprey, FL 34229

    Listed by Brent Martin, LLC MARCUS & COMPANY REALTY

    Stellar MLS
  • 206 FOUR KNOT LN, Osprey, FL 34229
    3 Beds2 Baths2,411 SqFt
    1/99 99
    Active

    $1,795,000

    206 FOUR KNOT LN, Osprey, FL 34229

    Listed by Leighton Allenby REALTY ONE GROUP MVP

    Stellar MLS
  • 1495 LANDVIEW LN, Osprey, FL 34229
    3 Beds2 Baths2,474 SqFt
    1/75 75
    Active

    $799,900

    1495 LANDVIEW LN, Osprey, FL 34229

    Listed by Pat Williams PAT WILLIAMS REALTY, 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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      4. Mortgage Calculator
      5. Buying Vocab
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      2. Selling Vocab
      Book a Call
      About
      1. About Us
      2. Meet Nicholas
      3. The Brokerage
      4. Join Us
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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

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.