Homes in ZIP Code 34229

• 

  

  

  /95

  $5,495,000

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

  730 Sarabay Rd, Osprey, FL 34229

  Premier Intracoastal Estate in Osprey4 Bedrooms | 6 Bathrooms | 6,308 Sq. Ft. | 2 Waterfront AcresA rare opportunity to own two acres of private waterfront property in Sarasota, 730 Sarabay is aconvergence of residential luxury and unparalleled waterfront living. The two-story home sits atthe end of a long drive behind a gated entrance and tranquil pond. With approximately 100

  Debbie Baraona ROBERT SLACK LLC

  730 Sarabay Rd, Osprey, FL 34229
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  /2

  $35,000 Sold Feb 17, 2025

  570 Blackburn Point Rd Unit C2, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • 234 Days On Market

  Last Listing Agent David Babel BRIGHT REALTY

  570 Blackburn Point Rd Unit C2, Osprey, FL 34229
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  /57

  Est $640,992 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
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  /8

  $750,000

  • Land
  • 0.47 Acre
  • $1,595,745 per Acre

  147 Osprey Point Dr, Osprey, FL 34229

  Your dream homesite awaits! This lot is located within the Oaks Bayside, one of Southwest Florida‘s most exclusive private, gated communities. This amazing property is near the community dock and fountain and is surrounded by some of the most grand and luxurious homes in the entire gulf coast region. The Oaks Club boasts 2 Championship Golf Courses, 12 Har-Tru Tennis Courts (4 lighted), State Of

  Mick Jordan BRIGHT REALTY

  147 Osprey Point Dr, Osprey, FL 34229
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  /2

  $325,000 Sold Jan 17, 2025

  51 MacEwen Dr Unit 20, Osprey, FL 34229

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft
  • Built 1990

  Last Sold Summary

  • $522/SF
  • 0 Days On Market

  Current Estimated Value $285,560

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  51 MacEwen Dr Unit 20, Osprey, FL 34229
• 

  

  /96

  Est $1,061,622 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
• 

  

  /19

  $129,500

  • 2 Beds
  • 1 Bath
  • 600 Sq Ft

  26 Siesta Cir W, Osprey, FL 34229

  Just Move In ... Affordable Fully furnished 2-bedroom home with central air is located in an active 55 and over community Located in the heart of Osprey with nearby shopping and dining and easy access to nearby Siesta Key Beach, Casey Key and Nokomis Beach along with The Legacy Bike trail and Oscer Scherer State Park. The Arbors Mobile Home Park with Low Hoa Fees offers a heated community pool

  Gary Hoskins COLDWELL BANKER REALTY

  26 Siesta Cir W, Osprey, FL 34229
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  /2

  $395,000 Sold Jun 16, 2025

  109 Burney Rd, Osprey, FL 34229

  • 2 Beds
  • 1.5 Baths
  • 714 Sq Ft
  • Built 1959

  Last Sold Summary

  • 8% Below List Price
  • $553/SF
  • 50 Days On Market

  Current Estimated Value $381,621

  Last Listing Agent Lori Madden MANGROVE REALTY ASSOCIATES

  109 Burney Rd, Osprey, FL 34229
• 

  

  /73

  Est $429,237 Not Listed For Sale

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

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229
• 

  

  /73

  $1,800,000 Pending

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

  409 N Point Rd Unit 1003, Osprey, FL 34229

  Beautifully updated and meticulously maintained 3 bedroom, 3 bath penthouse in Meridian at The Oaks Preserve. Offering a two car garage, 8’ solid core doors & roll down shutters on the screened balcony. The views are gorgeous. The Meridian has a residents-only pool, spa and work out room. Located in the heart of south Sarasota, The Oaks offers 2 championship golf courses, a world-class tennis

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 1003, Osprey, FL 34229
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  /2

  $700,000 Sold Oct 08, 2025

  826 Oak Briar Ln, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,589 Sq Ft
  • Built 2003

  Last Sold Summary

  • 10% Below List Price
  • $270/SF
  • 160 Days On Market

  Last Listing Agent Peter LaSalle PREFERRED SHORE LLC

  826 Oak Briar Ln, Osprey, FL 34229
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  /33

  Est $406,304 Not Listed For Sale

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

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229
• 

  

  /11

  $699,000

  • 3 Beds
  • 2 Baths
  • 2,058 Sq Ft

  110 Pine Ave, Osprey, FL 34229

  Heart of Osprey, this remodeled 3-bedroom, 2-bathroom pool home with huge yard, bring your RV and all your toys. Lots of room for storage. Enjoy sunsets, steps to fishing pier, kayak launch, Spanish Pointe, Oscar Scherer State Park, and Pine View School. No restrictions. Move-in ready enjoying the Florida lifestyle! For outdoor enthusiasts, this location is unbeatable. Launch your kayak or

  Marisa Marino BRIGHT REALTY

  110 Pine Ave, Osprey, FL 34229
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  /2

  $245,000 Sold Apr 21, 2025

  225 Woodland Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 18% Below List Price
  • $186/SF
  • 103 Days On Market

  Current Estimated Value $239,154

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  225 Woodland Dr, Osprey, FL 34229
• 

  

  /40

  Est $1,544,440 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  1787 S Creek Dr, Osprey, FL 34229

  1787 S Creek Dr, Osprey, FL 34229
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  /47

  $650,000

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  104 Park Trace Blvd, Osprey, FL 34229

  Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms,

  Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

  104 Park Trace Blvd, Osprey, FL 34229
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  /2

  $832,750 Sold Apr 10, 2025

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2025

  Last Sold Summary

  • $430/SF
  • 27 Days On Market

  Current Estimated Value $815,264

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 303, Osprey, FL 34229
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  /68

  Est $967,837 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,028 Sq Ft

  501 Velasquez Dr, Osprey, FL 34229

  501 Velasquez Dr, Osprey, FL 34229
• 

  

  /100

  $2,350,000

  • 3 Beds
  • 2.5 Baths
  • 3,738 Sq Ft

  393 N Point Rd Unit 1002, Osprey, FL 34229

  Experience Unmatched Luxury in this Meridian Penthouse! Welcome to the epitome of luxury living at Meridian at The Oaks Preserve. This stunning 3 bedroom, 2.5 bath penthouse offers a private 2-car garage and is designed for the discerning buyer who values quality, elegance, and an unparalleled location. From sunrise to dramatic color-drenched sunsets over the Gulf, your days will be filled with

  Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 1002, Osprey, FL 34229
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  /2

  $2,327,000 Sold Jun 18, 2025

  654 Trenton Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,582 Sq Ft
  • Built 1990

  Last Sold Summary

  • 5% Below List Price
  • $650/SF
  • 86 Days On Market

  Current Estimated Value $2,218,451

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  654 Trenton Way, Osprey, FL 34229
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  /40

  Est $515,439 Not Listed For Sale

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

  510 Meadow Sweet Cir, Osprey, FL 34229

  510 Meadow Sweet Cir, Osprey, FL 34229
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  /43

  $674,000

  • 4 Beds
  • 2 Baths
  • 2,145 Sq Ft

  819 Shadow Bay Way, Osprey, FL 34229

  A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  819 Shadow Bay Way, Osprey, FL 34229
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  /2

  $2,925,000 Sold Sep 23, 2025

  550 Dove Pointe, Osprey, FL 34229

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft
  • Built 2006

  Last Sold Summary

  • 11% Below List Price
  • $373/SF
  • 63 Days On Market

  Current Estimated Value $2,862,689

  Last Listing Agent Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
• 

  

  /52

  Est $2,381,384 Not Listed For Sale

  • 5 Beds
  • 8 Baths
  • 5,521 Sq Ft

  134 Marys Chapel Ct, Osprey, FL 34229

  134 Marys Chapel Ct, Osprey, FL 34229
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  /34

  $699,900 Pending

  • 4 Beds
  • 2 Baths
  • 2,434 Sq Ft

  866 Oak Briar Ln, Osprey, FL 34229

  Under contract-accepting backup offers. **NEW ROOF** Welcome to the highly desirable Park Trace Estates where residents enjoy low HOA fees! This beautiful pool home is move-in ready and features a split floor plan with three bedrooms and a 4th-bedroom/office giving you lots of space and flexibility. Many upgrades include pool resurfacing and tile, solar pool heater, pool pump, pool filter, AC,

  Brian Leakeas COLDWELL BANKER REALTY

  866 Oak Briar Ln, Osprey, FL 34229
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  /2

  $640,000 Sold Jan 17, 2025

  5300 Popoli Way, Sarasota, FL 34238

  • 2 Beds
  • 2 Baths
  • 1,682 Sq Ft
  • Built 2018

  Last Sold Summary

  • 5% Below List Price
  • $380/SF
  • 5 Days On Market

  Current Estimated Value $621,929

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  5300 Popoli Way, Sarasota, FL 34238
• 

  

  /41

  Est $566,105 Not Listed For Sale

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

  506 Oak Bay Dr, Osprey, FL 34229

  506 Oak Bay Dr, Osprey, FL 34229
• 

  

  /70

  $2,299,900

  • 5 Beds
  • 3.5 Baths
  • 3,236 Sq Ft

  180 Lookout Point Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  180 Lookout Point Dr, Osprey, FL 34229
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  /2

  $2,100,000 Sold Mar 26, 2025

  703 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 4,641 Sq Ft
  • Built 2007

  Last Sold Summary

  • 16% Below List Price
  • $452/SF
  • 95 Days On Market

  Current Estimated Value $1,992,362

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  703 N MacEwen Dr, Osprey, FL 34229
• 

  

  /79

  Est $1,343,418 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,521 Sq Ft

  1236 Yacht Harbor Dr, Osprey, FL 34229

  1236 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /55

  $429,900 Open House 1/04

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

  780 Sarabay Rd Unit 16, Osprey, FL 34229

  Waterfront Villa - 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! 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. This spacious 2-bedroom, 2-bath villa features a versatile bonus

  Mark Segreto RMS ELITE PROPERTIES

  780 Sarabay Rd Unit 16, Osprey, FL 34229
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  /2

  $1,500,000 Sold Jul 08, 2025

  269 Pine Ranch Trail, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft
  • Built 1997

  Last Sold Summary

  • 16% Below List Price
  • $420/SF
  • 76 Days On Market

  Current Estimated Value $1,462,447

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
• 

  

  /45

  Est $2,729,106 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,202 Sq Ft

  349 Yacht Harbor Dr, Osprey, FL 34229

  349 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /38

  $640,000 Pending

  • 3 Beds
  • 2 Baths
  • 1,889 Sq Ft

  178 Willow Bend Way, Osprey, FL 34229

  Move-in ready and impeccably maintained, this stunning 3-bedroom, 2-bath pool home offers exceptional updates and an unbeatable location in the coveted Park Trace Estates. Nearly 2,000 sq. ft. of bright, open living space features a desirable split floor plan, abundant natural light, and a beautifully landscaped, private fenced backyard.Major upgrades deliver true peace of mind:• All-new

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  178 Willow Bend Way, Osprey, FL 34229
• 

  /2

  $579,000 Sold Jan 16, 2025

  1327 Thornapple Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft
  • Built 2003

  Last Sold Summary

  • 2% Below List Price
  • $267/SF
  • 16 Days On Market

  Current Estimated Value $572,851

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1327 Thornapple Dr, Osprey, FL 34229
• 

  

  /50

  Est $363,257 Not Listed For Sale

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

  1821 Highland Rd, Osprey, FL 34229

  1821 Highland Rd, Osprey, FL 34229
• 

  

  /92

  $900,000

  • 3 Beds
  • 2 Baths
  • 2,216 Sq Ft

  21 Bayhead Ln, Osprey, FL 34229

  Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with

  Steve Abbe COLDWELL BANKER REALTY

  21 Bayhead Ln, Osprey, FL 34229
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  /2

  $3,050,000 Sold Aug 15, 2025

  5 N Casey Key Rd, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 2,380 Sq Ft
  • Built 1969

  Last Sold Summary

  • 27% Below List Price
  • $1,282/SF
  • 278 Days On Market

  Current Estimated Value $2,358,417

  Last Listing Agent Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229
• 

  

  /86

  Est $1,626,779 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,087 Sq Ft

  435 E MacEwen Dr, Osprey, FL 34229

  435 E MacEwen Dr, Osprey, FL 34229
• 

  

  /8

  $700,000

  • Land
  • 0.24 Acre
  • $2,916,667 per Acre

  3813 Parrot Bay Ct, Osprey, FL 34229

  Nestled within the exclusive community of Osprey, Florida, 3813 Parrot Bay Ct offers a rare opportunity to build your dream home on a premium lot in a tranquil cul-de-sac. This intimate enclave features just nine custom-built home sites, ensuring a private and close-knit neighborhood atmosphere. Best of all, buyers have the freedom to choose any builder to bring their vision to life. For boating

  Dawn Merrill COMPASS FLORIDA LLC

  3813 Parrot Bay Ct, Osprey, FL 34229

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