5,102

Homes in ZIP Code 34229

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  • /2

    $329,000 Sold Jan 14, 2026

    85 Navigation Cir, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,430 Sq Ft
    • Built 2014

    Last Sold Summary

    • 3% Below List Price
    • $230/SF
    • 8 Days On Market

    Current Estimated Value $329,550

    Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

    85 Navigation Cir, Osprey, FL 34229
    • /48

      Est $597,781 Not Listed For Sale

      522 Meadow Sweet Cir, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 2,424 Sq Ft
      • Built 1998
      522 Meadow Sweet Cir, Osprey, FL 34229

      Last Sold Summary

      • 13% Below List Price
      • $284/SF
      • 145 Days On Market

      Last Sold Price $687,500

      Last Listing Agent Sandi Tresh RE/MAX

  • /94

    $990,000

    • 3 Beds
    • 3 Baths
    • 2,778 Sq Ft

    401 N Point Rd Unit 504, Osprey, FL 34229

    FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you

    Mary Elizabeth Mock COLDWELL BANKER REALTY

    401 N Point Rd Unit 504, Osprey, FL 34229
  • /2

    $155,000 Sold Nov 26, 2025

    170 Edgewood Dr, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 959 Sq Ft
    • Built 1979

    Last Sold Summary

    • 6% Below List Price
    • $162/SF
    • 132 Days On Market

    Last Listing Agent Roberta Burish KW SUNCOAST

    170 Edgewood Dr, Osprey, FL 34229
    • /38

      Est $591,652 Not Listed For Sale

      574 Oak Bay Dr, Osprey, FL 34229

      • 3 Beds
      • 2.5 Baths
      • 2,325 Sq Ft
      • Built 1999
      574 Oak Bay Dr, Osprey, FL 34229

      Last Sold Summary

      • 5% Below List Price
      • $269/SF
      • 7 Days On Market

      Last Sold Price $625,000

      Last Listing Agent Frank Zeckel COLDWELL BANKER REALTY

  • /66

    $674,900 Pending

    • 3 Beds
    • 2 Baths
    • 1,929 Sq Ft

    1303 Thornapple Dr, Osprey, FL 34229

    Under contract-accepting backup offers. INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW $54,000 Barrel Tile ROOF (Nov 2025) in Sought After Willowbend---- A MAINTENANCE-FREE (lawn/landscaping/irrigation) Boutique Community ideally located near the Fitness Center and Community Pool, Pickleball Courts &

    Michael A Martino KELLER WILLIAMS ON THE WATER S

    1303 Thornapple Dr, Osprey, FL 34229
  • /2

    $3,900,000 Sold Aug 27, 2025

    426 N Casey Key Rd, Osprey, FL 34229

    • 3 Beds
    • 2 Baths
    • 1,876 Sq Ft
    • Built 1992

    Last Sold Summary

    • 20% Below List Price
    • $2,079/SF
    • 657 Days On Market

    Current Estimated Value $3,584,278

    Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

    426 N Casey Key Rd, Osprey, FL 34229
    • /48

      Est $745,553 Not Listed For Sale

      763 Shadow Bay Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 3,093 Sq Ft
      • Built 1998
      763 Shadow Bay Way, Osprey, FL 34229

      Last Sold Summary

      • 13% Below List Price
      • $278/SF
      • 22 Days On Market

      Last Sold Price $860,000

      Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

  • /36

    $569,000 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,172 Sq Ft

    1337 Copperwood Dr, Osprey, FL 34229

    This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

    Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

    1337 Copperwood Dr, Osprey, FL 34229
  • /2

    $3,500,000 Sold Dec 17, 2025

    431 Yacht Harbor Dr, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 3,006 Sq Ft
    • Built 1979

    Last Sold Summary

    • 19% Below List Price
    • $1,164/SF
    • 11 Days On Market

    Current Estimated Value $3,594,396

    Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

    431 Yacht Harbor Dr, Osprey, FL 34229
    • /39

      Est $688,811 Not Listed For Sale

      1096 Mallard Marsh Dr, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,492 Sq Ft
      • Built 2000
      1096 Mallard Marsh Dr, Osprey, FL 34229

      Last Sold Summary

      • 9% Below List Price
      • $305/SF
      • 39 Days On Market

      Last Sold Price $760,000

      Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.

  • /56

    $599,000 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,130 Sq Ft

    51 Webb St, Osprey, FL 34229

    Under contract-accepting backup offers. Location, location, location. Nestled west of the Trail in the heart of Osprey, this beautifully updated three-bedroom, two-bath home with a den offers a rare opportunity just moments from Sarasota Bay. Set on a spacious, private lot framed by mature oak trees and lush tropical landscaping, the property features no HOA or CDD restrictions. Inside, the home

    Marina Myers FINE PROPERTIES

    51 Webb St, Osprey, FL 34229
  • /2

    $2,400,000 Sold Jan 09, 2026

    432 Sorrento Dr, Osprey, FL 34229

    • 3 Beds
    • 3.5 Baths
    • 3,640 Sq Ft
    • Built 2007

    Last Sold Summary

    • 6% Below List Price
    • $659/SF
    • 7 Days On Market

    Current Estimated Value $2,371,739

    Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

    432 Sorrento Dr, Osprey, FL 34229
    • /2

      Est $723,628 Not Listed For Sale

      1000 Scherer Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,441 Sq Ft
      • Built 2003
      1000 Scherer Way, Osprey, FL 34229

      Last Sold Summary

      • 4% Below List Price
      • $309/SF
      • 54 Days On Market

      Last Sold Price $755,000

      Last Listing Agent Jody Callan PREMIER SOTHEBYS INTL REALTY

  • /55

    $515,000

    • 2 Beds
    • 2 Baths
    • 1,404 Sq Ft

    120 Villa Dr Unit 120, Osprey, FL 34229

    Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

    Hansel Pitts COLDWELL BANKER SARASOTA CENT.

    120 Villa Dr Unit 120, Osprey, FL 34229
  • /2

    $470,000 Sold Feb 10, 2026

    1363 New Forest Ln, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,738 Sq Ft
    • Built 2002

    Last Sold Summary

    • 14% Below List Price
    • $270/SF
    • 260 Days On Market

    Current Estimated Value $562,292

    Last Listing Agent Pamela Strom RE/MAX PALM

    1363 New Forest Ln, Osprey, FL 34229
    • /55

      Est $565,226 Not Listed For Sale

      5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

      • 2 Beds
      • 2 Baths
      • 2,143 Sq Ft
      • Built 2004
      5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

      Last Sold Summary

      • 11% Below List Price
      • $298/SF
      • 363 Days On Market

      Last Sold Price $638,000

      Last Listing Agent Jeremy Myers COMPASS PROPERTY MANAGEMENT LLC

  • /42

    $200,000

    • 2 Beds
    • 2 Baths
    • 1,223 Sq Ft

    211 Woodland Dr Unit 211, Osprey, FL 34229

    Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area

    Samantha Campbell BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

    211 Woodland Dr Unit 211, Osprey, FL 34229
  • /2

    $649,000 Sold Aug 26, 2025

    0 Four Knot Ln, Osprey, FL 34229

    • Land
    • 0.26 Acre
    • $2,496,154 per Acre

    Last Sold Summary

    • 4 Days On Market

    Last Listing Agent Gregory Wood CERUS REALTY

    0 Four Knot Ln, Osprey, FL 34229
    • /2

      Est $541,188 Not Listed For Sale

      590 Oak Bay Dr, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 1,892 Sq Ft
      • Built 1999
      590 Oak Bay Dr, Osprey, FL 34229

      Last Sold Summary

      • 11% Below List Price
      • $322/SF
      • 53 Days On Market

      Last Sold Price $609,000

      Last Listing Agent Kathy White PREFERRED SHORE LLC

  • /37

    $1,499,000 Open Sun 11AM - 1PM

    • 4 Beds
    • 3 Baths
    • 2,798 Sq Ft

    1471 Shoal Way, Osprey, FL 34229

    One or more photo(s) has been virtually staged. This exceptional residence truly checks every box.Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding principle in the home’s design. Tucked at the

    Lauren Doyle DALTON WADE INC

    1471 Shoal Way, Osprey, FL 34229
  • /2

    $43,000 Sold Nov 04, 2025

    570 Blackburn Point Rd Unit 6, Osprey, FL 34229

    Last Sold Summary

    • 2% Below List Price
    • 98 Days On Market

    Last Listing Agent Rick Bumbaca NORTHGROUP REAL ESTATE, INC

    570 Blackburn Point Rd Unit 6, Osprey, FL 34229
    • /46

      Est $599,867 Not Listed For Sale

      730 Fordingbridge Way, Osprey, FL 34229

      • 3 Beds
      • 2 Baths
      • 2,182 Sq Ft
      • Built 2002
      730 Fordingbridge Way, Osprey, FL 34229

      Last Sold Summary

      • 11% Below List Price
      • $309/SF
      • 128 Days On Market

      Last Sold Price $675,000

      Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  • /35

    $175,000 Pending

    • 1 Bed
    • 1.5 Baths
    • 865 Sq Ft

    200 Woodland Dr Unit 200, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Welcome to Pine Run in Osprey! Half-way between Sarasota and Venice, convenient to both with ample shopping and dining close by. Your 1 bedroom one and a half bath oasis is nestled on 20+ acres of lush native Florida landscape. This popular ground floor unit features large glass sliders and your own private courtyard in the front of the unit where

    Kathleen Griffin MICHAEL SAUNDERS & COMPANY

    200 Woodland Dr Unit 200, Osprey, FL 34229
  • /2

    $220,000 Sold Oct 23, 2025

    216 Woodland Dr Unit 216, Osprey, FL 34229

    • 2 Beds
    • 2 Baths
    • 1,325 Sq Ft
    • Built 1980

    Last Sold Summary

    • 10% Below List Price
    • $166/SF
    • 55 Days On Market

    Current Estimated Value $217,594

    Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

    216 Woodland Dr Unit 216, Osprey, FL 34229
    • /2

      Est $741,725 Not Listed For Sale

      356 S Creek Dr, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,369 Sq Ft
      • Built 1990
      356 S Creek Dr, Osprey, FL 34229

      Last Sold Summary

      • 2% Above List Price
      • $308/SF
      • 36 Days On Market

      Last Sold Price $730,000

      Last Listing Agent Christiana Kopetzky Michael Saunders

  • /45

    $599,000 Pending

    • 3 Beds
    • 2 Baths
    • 2,162 Sq Ft

    767 Fordingbridge Way, Osprey, FL 34229

    Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main

    Roger Pettingell COLDWELL BANKER REALTY

    767 Fordingbridge Way, Osprey, FL 34229
  • /2

    $660,000 Sold Mar 10, 2026

    471 Park Trace Blvd, Osprey, FL 34229

    • 4 Beds
    • 3 Baths
    • 2,267 Sq Ft
    • Built 2001

    Last Sold Summary

    • 12% Below List Price
    • $291/SF
    • 197 Days On Market

    Current Estimated Value $684,120

    Last Listing Agent Bill Cantrell WILLIAM RAVEIS REAL ESTATE

    471 Park Trace Blvd, Osprey, FL 34229
    • /81

      Est $1,105,709 Not Listed For Sale

      385 N Point Rd Unit 604, Osprey, FL 34229

      • 3 Beds
      • 3 Baths
      • 2,778 Sq Ft
      • Built 2000
      385 N Point Rd Unit 604, Osprey, FL 34229

      Last Sold Summary

      • 18% Below List Price
      • $486/SF
      • 48 Days On Market

      Last Sold Price $1,350,000

      Last Listing Agent Rosalie Phillips Michael Saunders

  • /44

    $445,000 Pending

    • 3 Beds
    • 2 Baths
    • 1,788 Sq Ft

    288 Woods Point Rd, Osprey, FL 34229

    Under contract-accepting backup offers. Perfectly positioned West of the Trail near Blackburn Point and Casey Key, this turnkey furnished 3 bedroom, 2 bathroom attached single family residence offers nearly 1,800 square feet of vaulted, light-filled interiors framed by lush preserve views. Set within an exclusive enclave of just 44 homes, this residence delivers the privacy and proportions of

    Toni Zarghami KW COASTAL LIVING III

    288 Woods Point Rd, Osprey, FL 34229
  • /2

    $1,015,000 Sold Aug 01, 2025

    678 Clear Creek Dr, Osprey, FL 34229

    • 5 Beds
    • 3 Baths
    • 3,912 Sq Ft
    • Built 2002

    Last Sold Summary

    • 8% Below List Price
    • $259/SF
    • 11 Days On Market

    Current Estimated Value $957,714

    Last Listing Agent Dena Dominiczak EXIT KING REALTY

    678 Clear Creek Dr, Osprey, FL 34229
    • /40

      Est $766,300 Not Listed For Sale

      672 Crane Prairie Way, Osprey, FL 34229

      • 4 Beds
      • 3 Baths
      • 2,830 Sq Ft
      • Built 2003
      672 Crane Prairie Way, Osprey, FL 34229

      Last Sold Summary

      • 19% Below List Price
      • $336/SF
      • 4 Days On Market

      Last Sold Price $950,000

      Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  • /2

    $489,249 New Construction

    • 2 Beds
    • 2 Baths
    • 952 Sq Ft

    791 S Tamiami Trail Unit 102, Osprey, FL 34229

    Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

    Laurie Eshleman PRO GROUP REALTY & PROP MGT

    791 S Tamiami Trail Unit 102, Osprey, FL 34229
  • /2

    $1,200,000 Sold Oct 24, 2025

    1484 Seafarer Dr, Osprey, FL 34229

    • 4 Beds
    • 3.5 Baths
    • 3,479 Sq Ft
    • Built 1987

    Last Sold Summary

    • 7% Below List Price
    • $345/SF
    • 82 Days On Market

    Current Estimated Value $1,173,298

    Last Listing Agent Seth Westerberg EXP REALTY LLC

    1484 Seafarer Dr, Osprey, FL 34229
    • /21

      Est $1,207,480 Not Listed For Sale

      1108 Bayhead Ln, Osprey, FL 34229

      • 4 Beds
      • 4 Baths
      • 3,541 Sq Ft
      • Built 1997
      1108 Bayhead Ln, Osprey, FL 34229

      Last Sold Summary

      • 51% Above List Price
      • $226/SF
      • 99 Days On Market

      Last Sold Price $800,000

      Last Listing Agent Rosalie Phillips Michael Saunders

  • /99

    $1,350,000 Pending

    • 4 Beds
    • 3 Baths
    • 3,679 Sq Ft

    133 Osprey Point Dr, Osprey, FL 34229

    Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer kitchen (with Thermador appliances) and all freshly painted. This 4 bedroom, 3 bathroom plus bonus room house

    Lisa Warren OWN SRQ LLC

    133 Osprey Point Dr, Osprey, FL 34229
  • /2

    $1,275,000 Sold Sep 30, 2025

    364 Renoir Dr, Osprey, FL 34229

    • 3 Beds
    • 2.5 Baths
    • 3,241 Sq Ft
    • Built 2003

    Last Sold Summary

    • 6% Below List Price
    • $393/SF
    • 7 Days On Market

    Current Estimated Value $1,260,850

    Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

    364 Renoir Dr, Osprey, FL 34229
    • /50

      Est $1,799,911 Not Listed For Sale

      280 Saratoga Ct, Osprey, FL 34229

      • 4 Beds
      • 3.5 Baths
      • 3,970 Sq Ft
      • Built 1994
      280 Saratoga Ct, Osprey, FL 34229

      Last Sold Summary

      • 1% Above List Price
      • $450/SF
      • 41 Days On Market

      Last Sold Price $1,787,500

      Last Listing Agent Mark Lyda GENEROUS PROPERTY

  • /74

    $385,000

    • 3 Beds
    • 3 Baths
    • 1,879 Sq Ft

    1795 Highland Rd, Osprey, FL 34229

    One or more photo(s) has been virtually staged. Perfectly positioned west of the Trail in the desirable coastal community of Towns-End Shores, this versatile property offers an exceptional opportunity to enjoy the Florida lifestyle while generating income. This home provides both peace of mind and outstanding value in one of Sarasota County’s most sought-after areas. Designed with flexibility in

    Rachel Tritschler RE/MAX ALLIANCE GROUP

    1795 Highland Rd, Osprey, FL 34229
  • /2

    $945,000 Sold Apr 15, 2025

    128 Sea Anchor Dr, Osprey, FL 34229

    • 3 Beds
    • 3 Baths
    • 2,677 Sq Ft
    • Built 1978

    Last Sold Summary

    • 3% Below List Price
    • $353/SF
    • 4 Days On Market

    Current Estimated Value $906,302

    Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

    128 Sea Anchor Dr, Osprey, FL 34229

Showing Results 361 - 400, Page 10 of 18

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