Homes in ZIP Code 34229

• 

  

  /2

  $700,000

  Sold May 27, 2026

  665 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,306 Sq Ft
  • Built 2003

  Last Sold Summary

  • 3% Below List Price
  • $304/SF
  • 37 Days On Market

  Current Estimated Value $711,120

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  665 Crane Prairie Way, Osprey, FL 34229
• 

  

  

  /61

  Est $352,017

  Not Listed For Sale

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2018

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  Last Sold Summary

  • 15 Days On Market
• 

  

  

  /66

  $655,000

  • 3 Beds
  • 3 Baths
  • 2,251 Sq Ft

  816 Shadow Bay Way, Osprey, FL 34229

  Set within Rivendell's 400 acres of lakes, preserves, and open spaces, this Osprey pool home checks the boxes buyers rarely find together: a quiet, established neighborhood, a long list of owner-completed upgrades, and no CDD fees. If you're looking for a move-in-ready foundation you can personalize over time, this one deserves a look.Major upgrades include:• NEW ROOF and GARAGE DOOR

  Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  816 Shadow Bay Way, Osprey, FL 34229
• 

  

  /2

  $137,000

  Sold Apr 17, 2026

  214 Palm Air Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 2% Below List Price
  • $143/SF
  • 1 Day On Market

  Last Listing Agent Garrett Sedlacek KELLER WILLIAMS ON THE WATER S

  214 Palm Air Dr, Osprey, FL 34229
• 

  

  

  /59

  Est $349,573

  Not Listed For Sale

  99 Explorer Dr Unit 102, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 2015

  99 Explorer Dr Unit 102, Osprey, FL 34229

  Last Sold Summary

  • 37 Days On Market
• 

  

  /11

  $575,000

  • Land
  • 17,424 Sq Ft
  • $1,437,500 per Acre

  143 Osprey Point Dr, Osprey, FL 34229

  One of the last available homesites in The Oaks Bayside. Almost 1/2 acre, at 17,647-square-feet, this exceptional lot presents a rare opportunity to build a custom luxury residence in one of Sarasota's most established and prestigious gated communities.Located behind the 24-hour staffed gates of The Oaks Bayside, this desirable homesite is ready to be transformed into the home you've always

  Steve Abbe COLDWELL BANKER REALTY

  143 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  $747,850

  Sold Aug 08, 2025

  424 Cezanne Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 2,945 Sq Ft
  • Built 1975

  Last Sold Summary

  • 16% Below List Price
  • $254/SF
  • 128 Days On Market

  Current Estimated Value $764,028

  Last Listing Agent Christine Pope MICHAEL SAUNDERS & COMPANY

  424 Cezanne Dr, Osprey, FL 34229
• 

  /2

  Est $363,550

  Not Listed For Sale

  4239 Expedition Way, Osprey, FL 34229

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

  4239 Expedition Way, Osprey, FL 34229

  Last Sold Summary

  • 115 Days On Market
• 

  

  /38

  $599,000

  $46K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 2,217 Sq Ft

  472 Park Trace Blvd, Osprey, FL 34229

  Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for

  Damon Zuchelli SUNDANCE REAL ESTATE SERVICES

  472 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  $2,300,000

  Sold Nov 05, 2025

  264 Saratoga Ct, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,857 Sq Ft
  • Built 1992

  Last Sold Summary

  • $596/SF
  • 9 Days On Market

  Current Estimated Value $2,199,712

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  264 Saratoga Ct, Osprey, FL 34229
• 

  /2

  Est $858,782

  Not Listed For Sale

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 503, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market
• 

  

  /97

  $1,399,000

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft

  385 N Point Rd Unit 701, Osprey, FL 34229

  Situated on the 7th floor of The Meridian, this sophisticated three-bedroom plus den, three-bath residence with private two-car garage offers elevated waterfront living behind the gates of the prestigious The Oaks Preserve and within the exclusive Oaks Club community. Every detail has been carefully curated for refined comfort, luxury, and effortless Florida indoor-outdoor living. A private

  Judy Wright, PA MICHAEL SAUNDERS & COMPANY

  385 N Point Rd Unit 701, Osprey, FL 34229
• 

  /2

  $358,000

  Sold Nov 13, 2025

  115 Green St, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,503 Sq Ft
  • Built 1990

  Last Sold Summary

  • 4% Above List Price
  • $238/SF
  • 5 Days On Market

  Current Estimated Value $355,375

  Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

  115 Green St, Osprey, FL 34229
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  /42

  Not Listed For Sale

  36 Siesta Cir W, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft
  • Built 1971

  36 Siesta Cir W, Osprey, FL 34229

  Last Sold Summary

  • 43 Days On Market
• 

  /2

  $699,000

  • Land
  • 23,958 Sq Ft
  • $1,270,909 per Acre

  410 Blue Garden Ln, Osprey, FL 34229

  Exceptional opportunity to build your dream estate in The Oaks, one of South Sarasota’s most prestigious gated golf and country club communities. Situated on a rare cul-de-sac lot, this generous parcel offers privacy, mature landscaping, and an ideal canvas for a custom residence. Enjoy convenient access to world-class amenities including championship golf, tennis and pickleball facilities, a

  Mark Grigoli ELITE PROPERTIES LLC

  410 Blue Garden Ln, Osprey, FL 34229
• 

  /2

  $527,500

  Sold Feb 27, 2026

  315 Bayshore Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,384 Sq Ft
  • Built 1979

  Last Sold Summary

  • 20% Below List Price
  • $221/SF
  • 72 Days On Market

  Current Estimated Value $529,612

  Last Listing Agent Norma Mladineo COLDWELL BANKER REALTY

  315 Bayshore Dr, Osprey, FL 34229
• 

  

  /4

  Est $29,577

  Not Listed For Sale

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  Last Sold Summary

  • 26 Days On Market
• 

  

  /70

  $1,649,000

  Pre-Foreclosure

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

  75 Osprey Point Dr, Osprey, FL 34229

  Offered at a price approaching the value of the two buildable lots alone, this architect-designed estate represents one of the most compelling opportunities currently available in The Oaks. Nestled beneath majestic oak trees and surrounded by exceptional privacy, this architecturally significant residence was designed by and as the personal home of renowned architect Bo MacEwen. The property

  Steve Abbe COLDWELL BANKER REALTY

  75 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  $520,000

  Sold Feb 26, 2026

  566 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,559 Sq Ft
  • Built 1997

  Last Sold Summary

  • 2% Below List Price
  • $203/SF
  • 4 Days On Market

  Current Estimated Value $524,097

  Last Listing Agent Greg Walters SARABAY REAL ESTATE INC

  566 Oak Bay Dr, Osprey, FL 34229
• 

  /2

  Est $807,911

  Not Listed For Sale

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

  Last Sold Summary

  • 13 Days On Market
• 

  

  /45

  $254,900

  Open Sat 1PM - 3PM $15K PRICE DROP

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

  116 Woodland Place Unit 116, Osprey, FL 34229

  Ready to make the move to paradise? Here’s your new home! Adorable two bedroom condo refreshed and ready for a new owner to enjoy convenience living. Crisp and clean with new luxury vinyl in the living room, dining room, hallway and entry, plus just freshly painted! Enjoy a bit of character with the shiplap wood wall in the dining room. Bathrooms have been remodeled with upscale appointments such

  Pat Williams PAT WILLIAMS REALTY, LLC

  116 Woodland Place Unit 116, Osprey, FL 34229
• 

  /2

  $540,000

  Sold Nov 24, 2025

  813 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • Built 1996

  Last Sold Summary

  • 4% Below List Price
  • $273/SF
  • 121 Days On Market

  Current Estimated Value $535,068

  Last Listing Agent Jeremy Egglefield PREFERRED SHORE LLC

  813 Oak Pond Dr, Osprey, FL 34229
• 

  /2

  Est $818,391

  Not Listed For Sale

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  Last Sold Summary

  • 14 Days On Market
• 

  

  /46

  $449,000

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft

  429 Patterson Ave, Osprey, FL 34229

  Incredible opportunity with a $10,000 credit to buyers at closing for costs or a rate buy-down! This low-maintenance gem is fully updated with a NEW AC, brand-new ductwork, stylish new counters/backsplash, new dishwasher, and a beautifully refreshed bathroom. The backyard is a private oasis boasting a brand-new 2025 heated saltwater pool and spa. Location is unbeatable: just .4 miles from the

  Brent Martin MARCUS & COMPANY REALTY

  429 Patterson Ave, Osprey, FL 34229
• 

  /2

  $300,000

  Sold Jun 15, 2026

  222 Glenwood Ave, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft
  • Built 1990

  Last Sold Summary

  • 9% Above List Price
  • $315/SF
  • 3 Days On Market

  Current Estimated Value $296,471

  Last Listing Agent Zalysia Kaczmarczyk JAY ALAN REAL ESTATE

  222 Glenwood Ave, Osprey, FL 34229
• 

  

  /24

  Not Listed For Sale

  338 Tropic Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft
  • Built 1979

  338 Tropic Dr, Osprey, FL 34229

  Last Sold Summary

  • 118 Days On Market
• 

  /2

  $617,999

  New Construction

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

  791 S Tamiami Trail Unit 101, 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 101, Osprey, FL 34229
• 

  /2

  $2,035,000

  Sold Jun 18, 2026

  600 Eagle Watch Ln, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,681 Sq Ft
  • Built 1992

  Last Sold Summary

  • 7% Below List Price
  • $553/SF
  • 197 Days On Market

  Current Estimated Value $2,109,325

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  600 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /79

  Est $608,714

  Not Listed For Sale

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2017

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  Last Sold Summary

  • 236 Days On Market
• 

  /2

  $75,000

  $35K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $535,714 per Acre

  0 Glenwood Ave, Osprey, FL 34229

  A rare opportunity in Osprey, FL — two adjacent residential lots, each approximately 5,916 sq ft, available individually or together for nearly 12,000 sq ft of combined space. Purchase one lot and build your ideal Florida home, or secure both lots and create either two separate residences or one expansive estate with room for your vision to unfold. Positioned in one of Sarasota County’s most

  Lori Turkovics COLDWELL BANKER REALTY

  0 Glenwood Ave, Osprey, FL 34229
• 

  /2

  $35,000

  Sold Jul 22, 2025

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 29% Below List Price
  • 62 Days On Market

  Current Estimated Value $34,868

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 17, Osprey, FL 34229
• 

  

  /13

  Est $960,667

  Not Listed For Sale

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229

  Last Sold Summary

  • 154 Days On Market
• 

  

  /62

  $660,000

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

  385 N Point Rd Unit 402, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 402, Osprey, FL 34229
• 

  /2

  $170,000

  Sold Mar 10, 2026

  238 Woodland Dr, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $197/SF
  • 126 Days On Market

  Current Estimated Value $173,469

  Last Listing Agent Kellie MacDonell COLDWELL BANKER REALTY

  238 Woodland Dr, Osprey, FL 34229
• 

  /2

  Not Listed For Sale

  570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

  • Studio

  570 Blackburn Point Rd Unit 14-LIDO, Osprey, FL 34229

  Last Sold Summary

  • 135 Days On Market
• 

  

  /4

  $109,000

  570 Blackburn Point Rd Unit 13, Osprey, FL 34229

  The slip can hold a boat with the maximum dimensions of 32.5L x 9'W x 9'H. This high-end dry boat storage facility has been hurricane rated. The facility houses 186 boat slips of varying sizes. The marina itself provides a full-service staff to handle all of your boating needs. This includes fuel, bait, ice, deli, drinks, pump out station, work racks supplied with water and electric. There is

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 13, Osprey, FL 34229
• 

  /2

  $430,000

  Sold May 19, 2026

  328 E Bay St, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1986

  Last Sold Summary

  • $486/SF
  • 2 Days On Market

  Current Estimated Value $433,954

  Last Listing Agent Steven Koleno BEYCOME OF FLORIDA LLC

  328 E Bay St, Osprey, FL 34229
• 

  

  /25

  Est $211,308

  Not Listed For Sale

  13 Bay Ave, Osprey, FL 34229

  13 Bay Ave, Osprey, FL 34229

  Last Sold Summary

  • 44 Days On Market
• 

  

  /44

  $875,000

  $35K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,271 Sq Ft

  293 Turquoise Ln, Osprey, FL 34229

  **STUNNING, UPDATED, MAINTENANCE-FREE Home is located in EMERALD WOODS, behind the Secure Gates of the Distinguished OAKS PRESERVE Neighborhood. Offering 3-Beds (or 2-Beds plus Den), 2-Baths and 2-Car Garage, Premium finishes abound throughout this home and include a Chef’s Kitchen, Tray Ceilings, Crown Moldings, Beautiful Luxury Vinyl Wood Plank, Plantation Shutters, an Oversized, Owner’s

  Mark Lyda GENEROUS PROPERTY

  293 Turquoise Ln, Osprey, FL 34229
• 

  /2

  $800,000

  Sold Mar 17, 2026

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $381/SF
  • 110 Days On Market

  Current Estimated Value $784,688

  Last Listing Agent Bart Tracy LASBURY-TRACY REALTY INC.

  242 Hidden Bay Dr Unit 401, Osprey, FL 34229

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