Homes in ZIP Code 34229

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  /60

  $10,750,000

  • 5 Beds
  • 8 Baths
  • 8,050 Sq Ft

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /2

  $520,000 Sold Nov 14, 2025

  708 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft
  • Built 2002

  Last Sold Summary

  • 5% Below List Price
  • $244/SF
  • 8 Days On Market

  Last Listing Agent Julien Collet AGILE GROUP REALTY

  708 Anna Hope Ln, Osprey, FL 34229
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  /2

  Est $736,246 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,323 Sq Ft

  520 Habitat Blvd, Osprey, FL 34229

  520 Habitat Blvd, Osprey, FL 34229
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  /32

  $159,900 Pending

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft

  300 Tropic Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Welcome to this charming, TURNKEY FURNISHED home in the desirable 55+ cooperative community of The Arbors, where you own your lot and enjoy the benefits of no monthly lot rent! Friendly neighbors and a peaceful setting make this a truly welcoming place to live! Enjoy affordable Florida living in this quaint community, where your neighbors quickly become

  Heidi Lionetti WHITE SANDS REALTY GROUP FL

  300 Tropic Dr, Osprey, FL 34229
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  /62

  $560,000 Sold May 29, 2025

  221 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,935 Sq Ft
  • Built 1984

  Last Sold Summary

  • 10% Below List Price
  • $289/SF
  • 68 Days On Market

  Current Estimated Value $570,335

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  221 Sorrento Dr, Osprey, FL 34229
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  /41

  Est $724,980 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,320 Sq Ft

  675 Crane Prairie Way, Osprey, FL 34229

  675 Crane Prairie Way, Osprey, FL 34229
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  /48

  $215,000

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

  244 Woodland Dr Unit 244, Osprey, FL 34229

  Tranquil Coastal Living in Pine Run244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  244 Woodland Dr Unit 244, Osprey, FL 34229
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  /2

  $640,000 Sold Jan 06, 2026

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft
  • Built 2004

  Last Sold Summary

  • 12% Below List Price
  • $258/SF
  • 130 Days On Market

  Last Listing Agent Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
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  /44

  Est $519,555 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,006 Sq Ft

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229

  1202 Jessie Harbor Dr Unit 1204, Osprey, FL 34229
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  /60

  $579,000

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  786 Sarabay Rd Unit 19, Osprey, FL 34229

  Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is intimate, quiet and peaceful. Part of the reason for the relaxing atmosphere

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  786 Sarabay Rd Unit 19, Osprey, FL 34229
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  /2

  $640,000 Sold Jun 04, 2025

  519 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $286/SF
  • 15 Days On Market

  Current Estimated Value $633,680

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  519 Habitat Blvd, Osprey, FL 34229
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  /40

  Est $1,190,035 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,827 Sq Ft

  109 Tina Island Dr, Osprey, FL 34229

  109 Tina Island Dr, Osprey, FL 34229
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  /92

  $1,775,000 Pre-Foreclosure

  • 4 Beds
  • 4 Baths
  • 4,001 Sq Ft

  75 Osprey Point Dr, Osprey, FL 34229

  **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

  Mark Lyda GENEROUS PROPERTY

  75 Osprey Point Dr, Osprey, FL 34229
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  /2

  $656,000 Sold Feb 21, 2025

  1109 Scherer Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $309/SF
  • 61 Days On Market

  Current Estimated Value $644,250

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1109 Scherer Way, Osprey, FL 34229
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  /2

  Est $498,948 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,116 Sq Ft

  502 Oak Bay Dr, Osprey, FL 34229

  502 Oak Bay Dr, Osprey, FL 34229
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  /78

  $750,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  102 Windward Dr, Osprey, FL 34229

  NEW PRICE! Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers

  David Cyr WILLIAM RAVEIS REAL ESTATE

  102 Windward Dr, Osprey, FL 34229
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  /2

  $324,000 Sold Mar 28, 2025

  76 Explorer Dr Unit 104, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2017

  Last Sold Summary

  • 7% Below List Price
  • $227/SF
  • 34 Days On Market

  Current Estimated Value $319,642

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY

  76 Explorer Dr Unit 104, Osprey, FL 34229
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  /65

  Est $983,513 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,632 Sq Ft

  800 Eaglenook Way, Osprey, FL 34229

  800 Eaglenook Way, Osprey, FL 34229
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  /24

  $600,000

  • Land
  • 0.34 Acre
  • $1,764,706 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

  Matthew Charland LLC GULF SHORES REALTY

  458 N Shore Dr, Osprey, FL 34229
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  /2

  $910,000 Sold Nov 19, 2025

  766 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft
  • Built 1998

  Last Sold Summary

  • 9% Below List Price
  • $265/SF
  • 132 Days On Market

  Last Listing Agent Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /9

  Est $191,523 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 630 Sq Ft

  242 Washington Ave, Osprey, FL 34229

  242 Washington Ave, Osprey, FL 34229
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  /3

  $89,000

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
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  /2

  $325,000 Sold Jul 24, 2025

  4236 Expedition Way Unit 106, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2016

  Last Sold Summary

  • 10% Below List Price
  • $213/SF
  • 90 Days On Market

  Current Estimated Value $323,587

  Last Listing Agent Susan Honsberger RE/MAX ALLIANCE GROUP

  4236 Expedition Way Unit 106, Osprey, FL 34229
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  /38

  Est $513,733 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,714 Sq Ft

  527 Meadow Sweet Cir, Osprey, FL 34229

  527 Meadow Sweet Cir, Osprey, FL 34229
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  /4

  $42,500

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 10.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
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  /2

  $500,000 Sold Mar 21, 2025

  629 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,867 Sq Ft
  • Built 1996

  Last Sold Summary

  • 17% Below List Price
  • $268/SF
  • 250 Days On Market

  Current Estimated Value $493,868

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  629 Oak Bay Dr, Osprey, FL 34229
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  /2

  Est $666,927 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft

  385 N Point Rd Unit 602, Osprey, FL 34229

  385 N Point Rd Unit 602, Osprey, FL 34229
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  /83

  $3,750,000

  • 4 Beds
  • 4.5 Baths
  • 4,781 Sq Ft

  1042 N Casey Key Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. If your dream is to create a place where generations can gather, relax, and make lasting memories, this Casey Key estate is ready to welcome you home. Set on 0.68 acres with 131 feet of Sarasota Bay frontage, this 4 bed 4.5 bath retreat offers room to spread out, unwind, and connect indoors and out. Each bedroom opens to the outdoors with bay

  Brandy Sheldon COLDWELL BANKER REALTY

  1042 N Casey Key Rd, Osprey, FL 34229
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  /2

  $400,000 Sold Apr 08, 2025

  4239 Expedition Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2016

  Last Sold Summary

  • 6% Below List Price
  • $254/SF
  • 115 Days On Market

  Current Estimated Value $390,757

  Last Listing Agent Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
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  /2

  Est $534,734 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  515 Oak Bay Dr, Osprey, FL 34229

  515 Oak Bay Dr, Osprey, FL 34229
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  /62

  $395,000

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2251 Jessie Harbor Dr, Osprey, FL 34229

  **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

  Mark Lyda GENEROUS PROPERTY

  2251 Jessie Harbor Dr, Osprey, FL 34229
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  /2

  $650,000 Sold Apr 18, 2025

  610 Pine Ranch Rd E, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,431 Sq Ft
  • Built 1995

  Last Sold Summary

  • 7% Below List Price
  • $267/SF
  • 113 Days On Market

  Current Estimated Value $631,669

  Last Listing Agent Kim Klee COLDWELL BANKER REALTY

  610 Pine Ranch Rd E, Osprey, FL 34229
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  /32

  Est $251,682 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft

  237 Woodland Dr Unit 237, Osprey, FL 34229

  237 Woodland Dr Unit 237, Osprey, FL 34229
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  /59

  $600,000 Open Sun 2PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,133 Sq Ft

  711 Shadow Bay Way, Osprey, FL 34229

  Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the

  Susan Keal MICHAEL SAUNDERS & COMPANY

  711 Shadow Bay Way, Osprey, FL 34229
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  /2

  $470,000 Sold Aug 22, 2025

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2005

  Last Sold Summary

  • 15% Below List Price
  • $217/SF
  • 80 Days On Market

  Current Estimated Value $484,183

  Last Listing Agent Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
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  /34

  Est $585,849 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft

  1358 Thornapple Dr, Osprey, FL 34229

  1358 Thornapple Dr, Osprey, FL 34229
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  /46

  $545,000

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Beautifully renovated home with a heated pool on just over half an acre. Nestled on a private, tree-lined street and surrounded by lush tropical landscaping, this property offers exceptional privacy and tranquility. This home has been completely renovated and is being sold turnkey. It has been successfully used as an investment property with substantial rental income. Recent updates include:

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
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  /2

  $250,000 Sold Oct 23, 2025

  207 Woodland Dr Unit 207, Osprey, FL 34229

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

  Last Sold Summary

  • 18% Below List Price
  • $189/SF
  • 491 Days On Market

  Current Estimated Value $243,295

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  207 Woodland Dr Unit 207, Osprey, FL 34229
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  /42

  Est $561,140 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,079 Sq Ft

  564 Crane Prairie Way, Osprey, FL 34229

  564 Crane Prairie Way, Osprey, FL 34229
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  /41

  $185,000 Open Sun 2PM - 4PM

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  238 Palm Air Dr, Osprey, FL 34229

  AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more

  John Alexander FINE PROPERTIES

  238 Palm Air Dr, Osprey, FL 34229

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