Homes in ZIP Code 34229

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  /76

  $1,089,000

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

  3936 Waypoint Ave, Osprey, FL 34229

  Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey, FL. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal lifestyle.Blending luxury, comfort, and

  Angelic Tassos CORCORAN DWELLINGS REALTY

  3936 Waypoint Ave, Osprey, FL 34229
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  /2

  $295,000 Sold Nov 14, 2025

  4267 Expedition Way, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2017

  Last Sold Summary

  • 5% Below List Price
  • $260/SF
  • 87 Days On Market

  Last Listing Agent Judi Cipollina COLDWELL BANKER REALTY

  4267 Expedition Way, Osprey, FL 34229
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  /37

  Est $943,501 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,917 Sq Ft

  77 Bayhead Ln, Osprey, FL 34229

  77 Bayhead Ln, Osprey, FL 34229
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  /76

  $455,000

  • 2 Beds
  • 2 Baths
  • 1,604 Sq Ft

  508 Meadow Sweet Cir, Osprey, FL 34229

  PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in

  Bill Cantrell FLORIDA HOME TEAM LLC

  508 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  $807,000 Sold Apr 22, 2025

  124 Tina Island Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,112 Sq Ft
  • Built 1975

  Last Sold Summary

  • 31% Below List Price
  • $382/SF
  • 244 Days On Market

  Current Estimated Value $829,425

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  124 Tina Island Dr, Osprey, FL 34229
• 

  

  /18

  Est $431,517 Not Listed For Sale

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

  121 Burney Rd, Osprey, FL 34229

  121 Burney Rd, Osprey, FL 34229
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  /32

  $3,300,000

  • 3 Beds
  • 4.5 Baths
  • 2,572 Sq Ft

  135 Tina Island Dr, Osprey, FL 34229

  Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and

  Cliff Glansen FLATFEE.COM

  135 Tina Island Dr, Osprey, FL 34229
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  /2

  $275,000 Sold Apr 11, 2025

  208 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 900 Sq Ft
  • Built 1963

  Last Sold Summary

  • 8% Below List Price
  • $306/SF
  • 33 Days On Market

  Current Estimated Value $279,529

  Last Listing Agent Stephen Hachey FLAT FEE MLS REALTY

  208 Pennsylvania Ave, Osprey, FL 34229
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  /35

  Est $874,471 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,332 Sq Ft

  1069 Scherer Way, Osprey, FL 34229

  1069 Scherer Way, Osprey, FL 34229
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  /41

  $699,000

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  14041 Bellagio Way Unit 415, Osprey, FL 34229

  A boater's dream. Enjoy waterfront living in this luxury penthouse unit with breathtaking views of the Intracoastal Waterway located in the premier gated community of The Villas at Bellagio. Upon entering the home, you are greeted by the inviting foyer leading down the art gallery-like hallway to the open family room and kitchen area. This three-bedroom, two-bathroom unit has many wonderful

  Stephen Hachey FLAT FEE MLS REALTY

  14041 Bellagio Way Unit 415, Osprey, FL 34229
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  /2

  $140,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 3% Below List Price
  • 59 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229
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  /71

  Est $283,234 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,305 Sq Ft

  752 Pine Run Dr, Osprey, FL 34229

  752 Pine Run Dr, Osprey, FL 34229
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  /4

  $549,000

  • Land
  • 1.07 Acres
  • $513,084 per Acre

  34 Washington Ave, Osprey, FL 34229

  Investor / Developer / Builder ALERT. Potential awaits with this exceptional opportunity to purchase just over one acre in a central location. Lot was previously platted as 7 lots and is zoned RSF3. Location has great proximity to many amenities; Oscar Scherer State Park, Old Spanish Point, Shopping, I75 Access, beaches and Pineview School. There have been some new homes built in the immediate

  Al Grabo ARCO REALTY GROUP

  34 Washington Ave, Osprey, FL 34229
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  /2

  $875,000 Sold May 01, 2025

  851 E Bay St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,329 Sq Ft
  • Built 2002

  Last Sold Summary

  • 6% Below List Price
  • $376/SF
  • 8 Days On Market

  Current Estimated Value $867,121

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  851 E Bay St, Osprey, FL 34229
• 

  

  /25

  Est $303,029 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,395 Sq Ft

  111 Villa Dr, Osprey, FL 34229

  111 Villa Dr, Osprey, FL 34229
• 

  

  /71

  $559,000

  • 4 Beds
  • 2 Baths
  • 2,186 Sq Ft

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229

  Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet,

  Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229
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  /2

  $527,500 Sold Sep 11, 2025

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft
  • Built 2005

  Last Sold Summary

  • 4% Below List Price
  • $270/SF
  • 60 Days On Market

  Current Estimated Value $521,888

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
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  /9

  Est $1,805,701 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,836 Sq Ft

  621 N MacEwen Dr, Osprey, FL 34229

  621 N MacEwen Dr, Osprey, FL 34229
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  /96

  $2,500,000

  • 4 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  49 Osprey Point Dr, Osprey, FL 34229

  Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

  Jonathan Abrams MICHAEL SAUNDERS & COMPANY

  49 Osprey Point Dr, Osprey, FL 34229
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  /72

  $615,000 Sold Mar 10, 2025

  593 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,340 Sq Ft
  • Built 2005

  Last Sold Summary

  • 16% Below List Price
  • $263/SF
  • 194 Days On Market

  Current Estimated Value $623,488

  Last Listing Agent Cynthia Bowers COLDWELL BANKER SARASOTA CENT.

  593 Crane Prairie Way, Osprey, FL 34229
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  /2

  Est $295,176 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 987 Sq Ft

  319 Patterson Ave, Osprey, FL 34229

  319 Patterson Ave, Osprey, FL 34229
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  /45

  $305,000

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  100 Navigation Cir, Osprey, FL 34229

  Welcome to Bay Street Village in Osprey, where maintenance-free Florida living awaits in this gorgeous gatedcommunity. This immaculate end-unit condo features 2 bedrooms, 2 bathrooms, and a 1-car garage. The garageis located beneath the unit and offers a private interior stairway leading to your second-floor residence.Enjoy an open-concept living and dining area perfect for

  Zita Bowers MICHAEL SAUNDERS & COMPANY

  100 Navigation Cir, Osprey, FL 34229
• 

  /2

  $850,000 Sold Dec 17, 2025

  678 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,483 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $342/SF
  • 4 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  678 Crane Prairie Way, Osprey, FL 34229
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  /50

  Est $1,110,813 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,691 Sq Ft

  214 Four Knot Ln, Osprey, FL 34229

  214 Four Knot Ln, Osprey, FL 34229
• 

  

  /39

  $660,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,279 Sq Ft

  804 Shadow Bay Way, Osprey, FL 34229

  Located in one of Osprey’s most desirable neighborhoods, this well-maintained 3 bedroom, 2 bath home with a den offers an unbeatable location just a short walk to Pine View School and minutes to Casey Key and Siesta Key. Enjoy peaceful pond and greenbelt views from the screened lanai, which features a covered sitting area, pool, and a separate patio with hot tub. The open, split floor plan

  Andrew Foltz PREFERRED SHORE LLC

  804 Shadow Bay Way, Osprey, FL 34229
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  /2

  $645,000 Sold Aug 25, 2025

  1212 Windward Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,994 Sq Ft
  • Built 1982

  Last Sold Summary

  • 17% Below List Price
  • $323/SF
  • 174 Days On Market

  Current Estimated Value $671,515

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  1212 Windward Dr, Osprey, FL 34229
• 

  /2

  Est $675,427 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,658 Sq Ft

  193 Willow Bend Way, Osprey, FL 34229

  193 Willow Bend Way, Osprey, FL 34229
• 

  

  /93

  $749,900

  • 3 Beds
  • 2 Baths
  • 2,505 Sq Ft

  186 Windward Dr, Osprey, FL 34229

  Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2-bath residence offers a split bedroom layout, unique community amenities, NEW ROOF in 2022, and plenty of room for a private pool. As you enter the home, you will be greeted by the formal living room and dining room to the left and hallway to the family room, kitchen, and dinette straight ahead. The entire interior has been

  Brittany Coleman KELLER WILLIAMS ON THE WATER S

  186 Windward Dr, Osprey, FL 34229
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  /2

  $150,000 Sold Jul 25, 2025

  107 Woodland Place Unit 107, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1979

  Last Sold Summary

  • 11% Below List Price
  • $173/SF
  • 49 Days On Market

  Current Estimated Value $155,072

  Last Listing Agent Carla Rayman Kidd COLDWELL BANKER REALTY

  107 Woodland Place Unit 107, Osprey, FL 34229
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  /53

  Est $597,566 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 2,009 Sq Ft

  803 Placid Lake Dr, Osprey, FL 34229

  803 Placid Lake Dr, Osprey, FL 34229
• 

  

  /99

  $1,197,000

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft

  403 Longbow Trail, Osprey, FL 34229

  Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort,

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, Osprey, FL 34229
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  /2

  $200,000 Sold Dec 09, 2025

  201 Woodland Dr Unit 201, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,316 Sq Ft
  • Built 1980

  Last Sold Summary

  • 33% Below List Price
  • $152/SF
  • 346 Days On Market

  Last Listing Agent Lauren Meadows PREFERRED PROPERTIES OF VENICE INC

  201 Woodland Dr Unit 201, Osprey, FL 34229
• 

  

  /49

  Est $614,302 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft

  1367 Thornapple Dr, Osprey, FL 34229

  1367 Thornapple Dr, Osprey, FL 34229
• 

  

  /56

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,760 Sq Ft

  811 Shadow Bay Way, Osprey, FL 34229

  Immaculate and truly move-in ready! This turnkey-furnished, spacious 2-bedroom + den, 2-bath home offers an open floor plan with gorgeous wood flooring throughout the living areas and den. The kitchen features marble countertops, an oversized island, large pantry, and quality finishes, while additional highlights include crown molding, plantation shutters, a private heated pool, and automatic

  Wayne Cherry PROGRAM REALTY, LLC

  811 Shadow Bay Way, Osprey, FL 34229
• 

  /2

  $1,014,000 Sold Nov 12, 2025

  201 Eaglenook Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,379 Sq Ft
  • Built 1992

  Last Sold Summary

  • 16% Below List Price
  • $300/SF
  • 211 Days On Market

  Last Listing Agent Dawn Bear WILLIAM RAVEIS REAL ESTATE

  201 Eaglenook Way, Osprey, FL 34229
• 

  

  /20

  Est $625,972 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,336 Sq Ft

  1323 Thornapple Dr, Osprey, FL 34229

  1323 Thornapple Dr, Osprey, FL 34229
• 

  /2

  $592,249 New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 201, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION -STARTING FROM THE MID $500,000'S. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 201, Osprey, FL 34229
• 

  /2

  $200,000 Sold Oct 06, 2025

  444 Washington Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,284 Sq Ft
  • Built 1953

  Last Sold Summary

  • 20% Below List Price
  • $156/SF
  • 9 Days On Market

  Current Estimated Value $209,850

  Last Listing Agent Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  444 Washington Ave, Osprey, FL 34229
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  /38

  Est $650,827 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,203 Sq Ft

  409 N Point Rd Unit 403, Osprey, FL 34229

  409 N Point Rd Unit 403, Osprey, FL 34229
• 

  

  /51

  $455,000

  • 2 Beds
  • 2 Baths
  • 2,148 Sq Ft

  32 Bay Ave, Osprey, FL 34229

  Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless

  Jennifer Pereira LOKATION

  32 Bay Ave, Osprey, FL 34229

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