Homes in ZIP Code 34229

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  /44

  $679,900

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

  This meticulously maintained, waterfront residence is in an amenity-rich, gated community. Offering over 2,000 square feet of casual luxury, the well-designed living space includes two bedrooms, two baths and features a welcoming foyer, a breakfast area, and a separate room ideal for a den or home office. The upgraded appointments throughout are numerous and include top-of-the-line KitchenAid

  Cindy Migone PREMIER SOTHEBY'S INTERNATIONAL REALTY

  5100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
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  /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
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  /37

  Est $364,047 Not Listed For Sale

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

  117 Navigation Cir Unit 101, Osprey, FL 34229

  117 Navigation Cir Unit 101, Osprey, FL 34229
• 

  

  

  /95

  $625,000

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3621 N Point Rd Unit 301, Osprey, FL 34229

  Ready to live a stress-free luxury condo lifestyle? There is no place better to do it than this 3 bedroom, 3 bath residence in Meridian at The Oaks Preserve. Nestled among the treetops, this end unit has a split floor plan and absolutely breathtaking sunset views over the Preserve and out to Little Sarasota Bay. Natural light floods the interior, highlighting the beauty of the hand-rubbed walnut

  Steve Abbe COLDWELL BANKER REALTY

  3621 N Point Rd Unit 301, Osprey, FL 34229
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  /2

  $710,000 Sold May 09, 2025

  710 Shadow Bay Way, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,533 Sq Ft
  • Built 2002

  Last Sold Summary

  • 11% Below List Price
  • $280/SF
  • 117 Days On Market

  Current Estimated Value $709,472

  Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

  710 Shadow Bay Way, Osprey, FL 34229
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  /57

  Est $670,044 Not Listed For Sale

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

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229
• 

  

  /48

  $635,000

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

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
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  /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

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  325 Osprey Point Dr, Osprey, FL 34229
• 

  

  /18

  Est $263,963 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 996 Sq Ft

  248 Washington Ave, Osprey, FL 34229

  248 Washington Ave, Osprey, FL 34229
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  /68

  $2,299,000 Open Sun 11AM - 2PM

  • 4 Beds
  • 4 Baths
  • 2,572 Sq Ft

  312 Yacht Harbor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a six-foot depth at mean low tide, the marina can accommodate 175 boats owned

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  312 Yacht Harbor Dr, Osprey, FL 34229
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  /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

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

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

  

  /13

  Est $1,193,870 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3603 N Point Rd Unit 603, Osprey, FL 34229

  3603 N Point Rd Unit 603, Osprey, FL 34229
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  /53

  $647,000

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

  522 Luminary Blvd, Osprey, FL 34229

  This exquisite three-bedroom, three-bath + den, Lee Wetherington built home exemplifies intelligent design and beauty in the community of Willowbend. This Ashley floor plan is thoughtfully oriented to the south, allowing for abundant natural light and stunning lakefront views. The residence features inviting curb appeal with a paver-accented driveway and walkway, leading to an impressive custom

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  522 Luminary Blvd, Osprey, FL 34229
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  /2

  $730,000 Sold Oct 24, 2025

  1728 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,320 Sq Ft
  • Built 1989

  Last Sold Summary

  • 6% Below List Price
  • $315/SF
  • 44 Days On Market

  Current Estimated Value $736,343

  Last Listing Agent Melanie Albaric MICHAEL SAUNDERS & COMPANY

  1728 S Creek Dr, Osprey, FL 34229
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  /50

  Est $806,513 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3603 N Point Rd Unit 501, Osprey, FL 34229

  3603 N Point Rd Unit 501, Osprey, FL 34229
• 

  

  /60

  $899,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,124 Sq Ft

  38 W Bay St, Osprey, FL 34229

  Under contract-accepting backup offers. Live like you’re on vacation in this updated Key West–style home West of the Trail. Upgrades include a new standing seam metal roof, hurricane impact windows, electric tankless water heater, wraparound "Lifeproof" composite decking, and a custom heated pool. Interior features vaulted ceilings with a mix of travertine, LVP, and tile flooring, plus a kitchen

  Mitch Helmuth HARRY ROBBINS ASSOC INC

  38 W Bay St, Osprey, FL 34229
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  /2

  $120,000 Sold Aug 29, 2025

  0 Cordes St Unit MFRN6137674, Osprey, FL 34229

  • Land
  • 0.18 Acre
  • $666,667 per Acre

  Last Sold Summary

  • 18% Below List Price
  • 153 Days On Market

  Last Listing Agent Zuzanna Kacprzak CENTURY 21 SCHMIDT REAL ESTATE

  0 Cordes St Unit MFRN6137674, Osprey, FL 34229
• 

  

  /25

  Est $549,055 Not Listed For Sale

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

  543 Meadow Sweet Cir, Osprey, FL 34229

  543 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /13

  $599,000

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  4428 Conchfish Ln, Osprey, FL 34229

  Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

  Mariana Georgieva HORIZON REALTY INTERNATIONAL

  4428 Conchfish Ln, Osprey, FL 34229
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  /2

  $520,000 Sold May 14, 2025

  544 Meadow Sweet Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,700 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $306/SF
  • 7 Days On Market

  Current Estimated Value $511,058

  Last Listing Agent Zita Bowers MICHAEL SAUNDERS & COMPANY

  544 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  Est $968,599 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,258 Sq Ft

  127 Turquoise Ln, Osprey, FL 34229

  127 Turquoise Ln, Osprey, FL 34229
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  /49

  $544,700

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft

  827 Placid Lake Dr, Osprey, FL 34229

  This lot and location really stands out! Set back on a quiet street, on a beautifully landscaped oversized lot, and a huge lawn in the backyard with a preserve as the backdrop, this well maintained, light-filled residence offers a rare combination of elegance, security, privacy, efficiency, value, and Florida lifestyle. This is a rare opportunity... one of the least expensive maintenance-free

  Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $975,000 Sold Aug 08, 2025

  3904 Waypoint Ave, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,344 Sq Ft
  • Built 2016

  Last Sold Summary

  • 18% Below List Price
  • $416/SF
  • 161 Days On Market

  Current Estimated Value $977,002

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3904 Waypoint Ave, Osprey, FL 34229
• 

  

  /64

  Est $260,708 Not Listed For Sale

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

  224 Woodland Dr, Osprey, FL 34229

  224 Woodland Dr, Osprey, FL 34229
• 

  

  /39

  $499,900 Open Sun 12PM - 3PM

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft

  570 Crane Prairie Way, Osprey, FL 34229

  Enjoy Maintenance Free Living in Beautiful Willowbend - 3-Bedroom, 2-Bath, 2-Car Garage, Pool Home ! LEE WETHERINGTON Opal Model ~Featuring Open Plan Very Private Pool on the Screen Enclosed Deck and Lanai. Complete w/ Extensive Upgrades Including: Crown Molding & Tray Ceilings in the Great Room w/ Special Lighting Features, also a Tray Ceiling in a Spacious Master Bedroom w/ Sitting area &

  Mickey Schweitzer MS REALTY MICKEY SCHWEITZER & ASSOCIATES LLC

  570 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  $725,000 Sold Jun 13, 2025

  608 Crane Prairie Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,678 Sq Ft
  • Built 2005

  Last Sold Summary

  • 20% Below List Price
  • $271/SF
  • 75 Days On Market

  Current Estimated Value $732,833

  Last Listing Agent Linda Williams GULF SHORES REALTY

  608 Crane Prairie Way, Osprey, FL 34229
• 

  

  /50

  Est $1,030,608 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,411 Sq Ft

  206 Four Knot Ln, Osprey, FL 34229

  206 Four Knot Ln, Osprey, FL 34229
• 

  

  /61

  $474,900

  • 3 Beds
  • 2 Baths
  • 1,883 Sq Ft

  7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

  PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

  Toy Coxey KW COASTAL LIVING

  7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
• 

  /2

  $534,000 Sold Dec 11, 2025

  757 Placid Lake Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,845 Sq Ft
  • Built 2001

  Last Sold Summary

  • 1% Below List Price
  • $289/SF
  • 3 Days On Market

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  757 Placid Lake Dr, Osprey, FL 34229
• 

  

  /59

  Est $992,467 Not Listed For Sale

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

  384 S Creek Ct, Osprey, FL 34229

  384 S Creek Ct, Osprey, FL 34229
• 

  

  /48

  $936,000

  • 3 Beds
  • 3 Baths
  • 2,283 Sq Ft

  172 Sea Anchor Dr, Osprey, FL 34229

  Amazing home with many improvements ideally located in a sought-after marina community. This beautifully updated 3-bedroom 3 bath residence has been thoughtfully enhanced for comfort, style and easy living. It's tucked inside a lively marina community where every day feels like vacation. This home features modern updates throughout. Newly remodeled kitchen, new master bath, luxury vinyl flooring,

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  172 Sea Anchor Dr, Osprey, FL 34229
• 

  /2

  $3,915,000 Sold Feb 26, 2025

  601 Fernwalk Ln, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 5,453 Sq Ft
  • Built 1986

  Last Sold Summary

  • 2% Below List Price
  • $718/SF
  • 214 Days On Market

  Current Estimated Value $3,314,711

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  601 Fernwalk Ln, Osprey, FL 34229
• 

  

  /99

  Est $698,725 Not Listed For Sale

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

  801 Oak Briar Ln, Osprey, FL 34229

  801 Oak Briar Ln, Osprey, FL 34229
• 

  

  /77

  $820,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2 Baths
  • 1,894 Sq Ft

  123 Windward Dr, Osprey, FL 34229

  PRICE IMPROVEMENT! This immaculate and meticulously maintained 3-bedroom, 2-bath home in the sought-after Southbay Yacht & Racquet community is move-in ready and packed with beautiful updates. The open-concept kitchen has been tastefully remodeled with stainless steel appliances, center isle and lighting, and both bathrooms have also been updated. Natural light fills the home through replaced

  David Cyr WILLIAM RAVEIS REAL ESTATE

  123 Windward Dr, Osprey, FL 34229
• 

  /2

  $600,000 Sold Apr 03, 2025

  818 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 2 Baths
  • 1,975 Sq Ft
  • Built 1996

  Last Sold Summary

  • 9% Below List Price
  • $304/SF
  • 86 Days On Market

  Current Estimated Value $580,180

  Last Listing Agent Jacqueline Middleton SHOWTIME REALTY

  818 Oak Pond Dr, Osprey, FL 34229
• 

  

  /57

  Est $657,856 Not Listed For Sale

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

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229
• 

  

  /55

  $2,249,000

  • 4 Beds
  • 3.5 Baths
  • 4,117 Sq Ft

  362 MacEwen Dr, Osprey, FL 34229

  Experience luxury living in this beautifully appointed traditional home featuring 4 bedrooms, 3.5 bathrooms, and a dedicated office. The formal living room offers a fireplace and French doors, allowing separation from the kitchen and family room for more intimate gatherings. The spacious master suite includes two walk-in closets with custom built-ins, a sitting area, and a spa-inspired bath with

  Steve Abbe COLDWELL BANKER REALTY

  362 MacEwen Dr, Osprey, FL 34229
• 

  /2

  $247,000 Sold Aug 14, 2025

  121 Woodland Place Unit 121, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1979

  Last Sold Summary

  • 7% Below List Price
  • $186/SF
  • 3 Days On Market

  Current Estimated Value $248,025

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  121 Woodland Place Unit 121, Osprey, FL 34229
• 

  

  /96

  Est $1,040,817 Not Listed For Sale

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

  385 N Point Rd Unit 501, Osprey, FL 34229

  385 N Point Rd Unit 501, Osprey, FL 34229
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  /4

  $115,000

  570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

  This slip will house a boat with the maximum dimensions of 27.5'L x 11'W x 11.5'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.

  David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit LONGBOAT 43, Osprey, FL 34229

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