Homes in ZIP Code 34229

• 

  

  

  /40

  $695,000

  $5K PRICE DROP Under Contract

  • 3 Beds
  • 3 Baths
  • 2,837 Sq Ft

  264 Woods Point Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Ideally located to enjoy all that Sarasota, Venice and Casey Key has to offer, this superbly remodeled maintenance-free home offers more than 2,800 square feet of thoughtfully redesigned living space and lives comfortably like a private, stand-alone residence. Nestled within an intimate enclave of just 44 homes, this property offers the ultimate

  Mina Johnson MICHAEL SAUNDERS & COMPANY

  264 Woods Point Rd, Osprey, FL 34229
• 

  

  /2

  $745,000

  Sold Jan 16, 2026

  640 Crane Prairie Way, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,534 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $294/SF
  • 23 Days On Market

  Current Estimated Value $759,692

  Last Listing Agent Jay Mitchell COLDWELL BANKER REALTY

  640 Crane Prairie Way, Osprey, FL 34229
• 

  

  /2

  Est $1,460,665

  Not Listed For Sale

  639 Eagle Watch Ln, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 3,906 Sq Ft
  • Built 1989

  639 Eagle Watch Ln, Osprey, FL 34229

  Last Sold Summary

  • 212 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  

  /54

  $425,000

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

  780 Sarabay Rd Unit 16, Osprey, FL 34229

  Waterfront Villa w/BOAT SLIPS - Large Private Courtyard & 2- Car Garage - Maintenance Free Living. Single story home-like living. Fish off the Pier or sit on the dock & enjoy the sunsets! NEW DOCK & PIER Welcome to Heron Bay Club, an exclusive enclave of just 25 uniquely designed villas situated on 11 acres along the Little Sarasota Bay across from Casey Key. Enjoy carefree coastal living with

  Mark Segreto RMS ELITE PROPERTIES

  780 Sarabay Rd Unit 16, Osprey, FL 34229
• 

  

  /2

  $533,000

  Sold Aug 04, 2026

  4424 Conchfish Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,370 Sq Ft
  • Built 2017

  Last Sold Summary

  • 13% Below List Price
  • $225/SF
  • 60 Days On Market

  Current Estimated Value $577,297

  Last Listing Agent Ashley Wallace COLDWELL BANKER REALTY

  4424 Conchfish Ln, Osprey, FL 34229
• 

  

  /25

  Est $548,368

  Not Listed For Sale

  543 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,981 Sq Ft
  • Built 2001

  543 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 52 Days On Market

  Last Listing Agent Mary Jo Violett WHITE SANDS REALTY GROUP FL
• 

  

  /37

  $185,000

  $10K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,199 Sq Ft

  320 Tropic Dr, Osprey, FL 34229

  Virtually Staged. Welcome to this Partially Furnished home in the desirable 55+ cooperative community of The Arbors!This property in The Arbors stands out primarily for its rare inclusion of a separate adjacent lot, providing significant flexibility for either added privacy or future expansion. This is a very special property as it includes a second lot with an existing beautiful gazebo and

  Susan Retzke RE/MAX PALM

  320 Tropic Dr, Osprey, FL 34229
• 

  /2

  $95,000

  Sold Apr 30, 2026

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Last Sold Summary

  • 4% Below List Price
  • 17 Days On Market

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
• 

  

  /59

  Est $1,214,520

  Not Listed For Sale

  384 S Creek Ct, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,811 Sq Ft
  • Built 1982

  384 S Creek Ct, Osprey, FL 34229

  Last Sold Summary

  • 71 Days On Market

  Last Listing Agent Brandi Furlan KW COASTAL LIVING III
• 

  

  /92

  $789,000

  $136K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,246 Sq Ft

  21 Bayhead Ln, Osprey, FL 34229

  Looking for a home you can truly fall in love with? Your search ends here. This thoughtfully updated, impeccably maintained 3 bedroom, 2 bath residence in The Oaks Preserve offers the perfect blend of comfort, style, and privacy. And you can BUY WITH CONFIDENCE — THE PROACTIVE SELLERS HAVE COMPLETED INSPECTIONS IN ADVANCE TO SHARE WITH BUYERS, GIVING YOU CLARITY FROM THE START. No guessing...what

  Steve Abbe COLDWELL BANKER REALTY

  21 Bayhead Ln, Osprey, FL 34229
• 

  /2

  $215,000

  Sold Nov 12, 2025

  158 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,480 Sq Ft
  • Built 2014

  Last Sold Summary

  • 9% Below List Price
  • $145/SF
  • 12 Days On Market

  Last Listing Agent Renee Marquiss NEXTHOME IN THE SUN

  158 Edgewood Dr, Osprey, FL 34229
• 

  

  /99

  Est $656,645

  Not Listed For Sale

  801 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,330 Sq Ft
  • Built 2004

  801 Oak Briar Ln, Osprey, FL 34229

  Last Sold Summary

  • 6 Days On Market

  Last Listing Agent Christopher Costello RE/MAX PALM
• 

  

  /57

  $319,000

  • 2 Beds
  • 2.5 Baths
  • 1,240 Sq Ft

  1819 Highland Rd, Osprey, FL 34229

  This beautifully appointed 2-bedroom, 2-bath townhome offers a wonderful blend of comfort, privacy, and Florida living in "The Osprey", a community of just 12 residences. The open-concept floor plan features high ceilings, generous living spaces, and large windows that fill the home with an abundance of natural light. The spacious owner’s retreat provides a peaceful setting for relaxation, while

  Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  1819 Highland Rd, Osprey, FL 34229
• 

  /2

  $2,470,000

  Sold Aug 27, 2026

  449 Webbs Cove, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 5,287 Sq Ft
  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • $467/SF
  • 18 Days On Market

  Current Estimated Value $2,541,549

  Last Listing Agent Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  449 Webbs Cove, Osprey, FL 34229
• 

  

  /57

  Est $660,846

  Not Listed For Sale

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft
  • Built 2005

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  Last Sold Summary

  • 222 Days On Market

  Last Listing Agent Bernadette Caswell MICHAEL SAUNDERS & COMPANY
• 

  

  /71

  $9,750,000

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

  1216 N Casey Key Rd, Osprey, FL 34229

  At the northernmost point of Casey Key, where the Gulf meets the tranquil waters of Little Sarasota and Blackburn Bay, an extraordinary private estate unfolds between two worlds of water. Beyond a secluded entrance lies a residence of remarkable distinction, an Italianate architectural masterpiece spanning more than 8,000 square feet, with a private sandy beach on the Gulf and a rare,

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $1,500,000

  Sold Aug 12, 2026

  893 MacEwen Dr, Osprey, FL 34229

  • Land
  • 28,749 Sq Ft
  • $2,272,727 per Acre

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  893 MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $726,776

  Not Listed For Sale

  401 N Point Rd Unit 401, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2003

  401 N Point Rd Unit 401, Osprey, FL 34229

  Last Sold Summary

  • 17 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /7

  $289,999

  $30K PRICE INCREASE

  • Land
  • 5,662 Sq Ft
  • $2,230,762 per Acre

  456 Washington Ave, Osprey, FL 34229

  Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and the

  Mike Vo FLOTACAL

  456 Washington Ave, Osprey, FL 34229
• 

  /2

  $730,000

  Sold May 13, 2026

  1019 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft
  • Built 2004

  Last Sold Summary

  • 1% Below List Price
  • $292/SF
  • 10 Days On Market

  Current Estimated Value $736,209

  Last Listing Agent Christine Appice CENTURY 21 SCHMIDT REAL ESTATE

  1019 Scherer Way, Osprey, FL 34229
• 

  

  /96

  Est $950,093

  Not Listed For Sale

  385 N Point Rd Unit 501, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2000

  385 N Point Rd Unit 501, Osprey, FL 34229

  Last Sold Summary

  • 0 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY
• 

  

  /34

  $109,900

  Open Sun 1PM - 3PM $29K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  348 Tropic Dr, Osprey, FL 34229

  Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

  John Alexander FINE PROPERTIES

  348 Tropic Dr, Osprey, FL 34229
• 

  /2

  $4,700,000

  Sold Jun 17, 2026

  730 Sarabay Rd, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 6,308 Sq Ft
  • Built 2011

  Last Sold Summary

  • 14% Below List Price
  • $745/SF
  • 174 Days On Market

  Current Estimated Value $4,621,992

  Last Listing Agent Debbie Baraona JASON MITCHELL REAL ESTATE FLO

  730 Sarabay Rd, Osprey, FL 34229
• 

  

  /73

  Est $409,986

  Not Listed For Sale

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft
  • Built 2000

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

  Last Sold Summary

  • 7 Days On Market

  Last Listing Agent Pan Steele, GRI COLDWELL BANKER REALTY
• 

  /2

  $1,050,000

  Pending

  • 3 Beds
  • 2 Baths
  • 2,255 Sq Ft

  292 Turquoise Ln, Osprey, FL 34229

  his stunning, updated home sits on a corner lot; the largest in Emerald Woods. Located behind the gates of The Oaks Preserve, this maintenance free residence features 3 bedrooms, 2 baths and a 2-car air conditioned garage along with premium finishes throughout. The updated kitchen, equipped with high-end stainless steel appliances, will delight any home chef. The spacious master suite includes a

  Steve Abbe COLDWELL BANKER REALTY

  292 Turquoise Ln, Osprey, FL 34229
• 

  /2

  $1,500,000

  Sold Dec 12, 2025

  325 Osprey Point Dr, Osprey, FL 34229

  • 3 Beds
  • 4.5 Baths
  • 3,905 Sq Ft
  • Built 1986

  Last Sold Summary

  • 11% Below List Price
  • $384/SF
  • 12 Days On Market

  Current Estimated Value $1,524,384

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  325 Osprey Point Dr, Osprey, FL 34229
• 

  /2

  Est $1,015,433

  Not Listed For Sale

  247 Keel Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,871 Sq Ft
  • Built 1979

  247 Keel Way, Osprey, FL 34229

  Last Sold Summary

  • 70 Days On Market

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC
• 

  

  /19

  $510,000

  $25K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  4429 Conchfish Ln, Osprey, FL 34229

  Virtually Staged. MOTIVATED SELLER- SPACIOUS 2,000+ SQ FT HOME, UPDATED BEDROOM FLOORING, PRIVATE BACKYARD, COVERED LANAI & 2-CAR GARAGE in The Palms of Casey Key, offering a comfortable layout designed for both everyday living and entertaining. The inviting interior features UPDATED FLOORING THROUGHOUT THE BEDROOMS & CLOSETS with durable tile in the main living areas for easy maintenance. A

  Jennifer Kenna EXP REALTY, LLC

  4429 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $285,000

  Sold Mar 24, 2026

  2043 Cordes St, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,186 Sq Ft
  • Built 1957

  Last Sold Summary

  • 5% Below List Price
  • $240/SF
  • 44 Days On Market

  Current Estimated Value $282,675

  Last Listing Agent Travis Matthews PREFERRED SHORE LLC

  2043 Cordes St, Osprey, FL 34229
• 

  /2

  Est $3,620,828

  Not Listed For Sale

  275 Lookout Point Dr, Osprey, FL 34229

  • 5 Beds
  • 5 Baths
  • 5,279 Sq Ft
  • Built 2007

  275 Lookout Point Dr, Osprey, FL 34229

  Last Sold Summary

  • 124 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY
• 

  

  /19

  $655,000

  • 3 Beds
  • 2.5 Baths
  • 2,792 Sq Ft

  700 Shadow Bay Way, Osprey, FL 34229

  Welcome to 700 Shadow Bay Way, an impressive 3-bedroom, 2.5-bath pool home with a den, 3-car garage and more than 2,500 square feet of living space in the highly desirable Woodlands at Rivendell. Set on an oversized corner lot, this spacious home offers a bright, open and functional floor plan with high ceilings, crown molding, a generous great room and a separate dining area ideal for both

  Kara Money KARA MONEY LLC

  700 Shadow Bay Way, Osprey, FL 34229
• 

  /2

  $113,000

  Sold Feb 17, 2026

  26 Siesta Cir W, Osprey, FL 34229

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft
  • Built 1968

  Last Sold Summary

  • 13% Below List Price
  • $188/SF
  • 55 Days On Market

  Last Listing Agent Gary Hoskins COLDWELL BANKER REALTY

  26 Siesta Cir W, Osprey, FL 34229
• 

  

  /40

  Est $490,104

  Not Listed For Sale

  510 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft
  • Built 2001

  510 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 19 Days On Market

  Last Listing Agent Mary Jo Violett WHITE SANDS REALTY GROUP FL
• 

  

  /49

  $1,750,000

  $600K PRICE DROP

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

  18 N Casey Key Rd, Osprey, FL 34229

  Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $1,700,000

  Sold Jan 15, 2026

  409 N Point Rd Unit 1003, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2004

  Last Sold Summary

  • 6% Below List Price
  • $612/SF
  • 0 Days On Market

  Current Estimated Value $1,631,956

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 1003, Osprey, FL 34229
• 

  

  /41

  Est $544,452

  Not Listed For Sale

  506 Oak Bay Dr, Osprey, FL 34229

  • 4 Beds
  • 2.5 Baths
  • 1,944 Sq Ft
  • Built 1995

  506 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 10 Days On Market

  Last Listing Agent Sharon Morea EXIT KING REALTY
• 

  

  /19

  $409,900

  $33K PRICE DROP

  • 2 Beds
  • 2 Baths
  • 1,725 Sq Ft

  1811 Highland Rd, Osprey, FL 34229

  PRIVATE NEIGHBORHOOD - Fully Furnished 2 Bedroom Townhouse in the Casey Key area, QUAINT, SPACIOUS 2-CAR Tandem GARAGE + Carport, modern, high ceilings, kitchen upgrades, screened balcony, 2 beds + den; 2 baths; living area and kitchen open plan; community poolConveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef

  Stephen Hachey REALTY OF RIVERVIEW LLC

  1811 Highland Rd, Osprey, FL 34229
• 

  /2

  $525,000

  Sold May 21, 2026

  1348 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $242/SF
  • 9 Days On Market

  Current Estimated Value $530,991

  Last Listing Agent Margot Vigar (Leonard) COLDWELL BANKER REALTY

  1348 Thornapple Dr, Osprey, FL 34229
• 

  

  /50

  Est $346,204

  Not Listed For Sale

  1821 Highland Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Built 1998

  1821 Highland Rd, Osprey, FL 34229

  Last Sold Summary

  • 53 Days On Market

  Last Listing Agent Patrick Brogley KELLER WILLIAMS ON THE WATER S
• 

  

  /61

  $1,950,000

  Open Sat 12PM - 4PM

  • 5 Beds
  • 5.5 Baths
  • 4,885 Sq Ft

  97 Sugar Mill Dr, Osprey, FL 34229

  Welcome to an exceptional estate in The Oaks Bayside, where timeless elegance meets modern luxury in one of Sarasota County’s most prestigious gated communities. Perfectly positioned on a private, lush homesite beneath a canopy of majestic oaks, this stunning 5-bedroom, 6-bath residence offers the ideal blend of space, sophistication, and serenity. Step inside to discover a thoughtfully designed

  Maria 'Indy' Domenech PALM PARADISE REALTY GROUP

  97 Sugar Mill Dr, Osprey, FL 34229

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