Homes in ZIP Code 34229

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  /100

  $3,995,000

  • 4 Beds
  • 7 Baths
  • 6,705 Sq Ft

  691 Eagle Watch Ln, Osprey, FL 34229

  Nestled within the exclusive gated community of the Oaks Club in Osprey, Florida. This singular estate represents a masterful confluence of architectural refinement and modern luxury, encompassing nearly 7000 ft.2 of conditioned living space, the residence has undergone an extraordinary transformation – reflecting an investment exceeding $1.5 million – to achieve a standard of craftsmanship

  Renee Preininger SARASOTA TRUST REALTY COMPANY

  691 Eagle Watch Ln, Osprey, FL 34229
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  /2

  $1,200,000 Sold Oct 24, 2025

  1484 Seafarer Dr, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,479 Sq Ft
  • Built 1987

  Last Sold Summary

  • 7% Below List Price
  • $345/SF
  • 82 Days On Market

  Last Listing Agent Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
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  /2

  Est $818,864 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,433 Sq Ft

  1030 Scherer Way, Osprey, FL 34229

  1030 Scherer Way, Osprey, FL 34229
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  /61

  $325,000

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  116 Navigation Cir Unit 106, Osprey, FL 34229

  Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

  Pan Steele, GRI COLDWELL BANKER REALTY

  116 Navigation Cir Unit 106, Osprey, FL 34229
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  /2

  $1,275,000 Sold Sep 30, 2025

  364 Renoir Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,241 Sq Ft
  • Built 2003

  Last Sold Summary

  • 6% Below List Price
  • $393/SF
  • 7 Days On Market

  Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229
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  /55

  Est $963,610 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,360 Sq Ft

  792 Placid Lake Dr, Osprey, FL 34229

  792 Placid Lake Dr, Osprey, FL 34229
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  /60

  $2,690,000

  • 6 Beds
  • 4 Baths
  • 4,546 Sq Ft

  225 Harbor House Dr, Osprey, FL 34229

  Considered one of the finest community owned marinas on Florida’s west coast, Southbay Yacht & Racquet Club is a premier waterfront community featuring a seven acre deep water boat basin and a lifestyle centered around the water. This exceptional 4,560 sq ft residence captures the essence of refined coastal living, blending modern updates with resort style amenities in one of Sarasota County’s

  William Kerswill PINEYWOODS REALTY LLC

  225 Harbor House Dr, Osprey, FL 34229
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  /2

  $945,000 Sold Apr 15, 2025

  128 Sea Anchor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,677 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Below List Price
  • $353/SF
  • 4 Days On Market

  Current Estimated Value $917,383

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  128 Sea Anchor Dr, Osprey, FL 34229
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  /45

  Est $656,693 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,284 Sq Ft

  573 Crane Prairie Way, Osprey, FL 34229

  573 Crane Prairie Way, Osprey, FL 34229
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  /28

  $1,150,000

  • 3 Beds
  • 2 Baths
  • 2,374 Sq Ft

  14041 Bellagio Way Unit 218, Osprey, FL 34229

  Experience exceptional waterfront living at Osprey Harbor Village. This 3-bedroom, 2-bath residence offers 2,374 sq ft of well-designed space with direct west-facing views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo is being sold turnkey furnished, and includes a deeded 40’ wet slip—providing immediate access

  Kelli Eggen COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 218, Osprey, FL 34229
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  /2

  $2,625,000 Sold Sep 16, 2025

  478 Oriskany Ct, Osprey, FL 34229

  • 4 Beds
  • 7 Baths
  • 5,778 Sq Ft
  • Built 1999

  Last Sold Summary

  • 12% Below List Price
  • $454/SF
  • 10 Days On Market

  Current Estimated Value $2,597,763

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  478 Oriskany Ct, Osprey, FL 34229
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  /40

  Est $734,952 Not Listed For Sale

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

  669 Crane Prairie Way, Osprey, FL 34229

  669 Crane Prairie Way, Osprey, FL 34229
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  /73

  $2,395,000

  • 5 Beds
  • 7 Baths
  • 6,001 Sq Ft

  340 Osprey Point Dr, Osprey, FL 34229

  Introducing The Grand Estate at The Oaks Bayside—a true masterpiece of refined living within one of Sarasota’s most prestigious gated communities. Surrounded by majestic oak trees and lush tropical landscaping, this extraordinary residence offers the perfect blend of elegance, comfort, and privacy. A brand-new roof (2024) crowns this sprawling estate, while a pavered circular driveway leads to a

  Lee Brewer RE/MAX ALLIANCE GROUP

  340 Osprey Point Dr, Osprey, FL 34229
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  /2

  $1,325,000 Sold Nov 07, 2025

  402 Walls Way, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,464 Sq Ft
  • Built 2014

  Last Sold Summary

  • 22% Below List Price
  • $383/SF
  • 187 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  402 Walls Way, Osprey, FL 34229
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  /11

  Est $320,912 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft

  217 Glenwood Ave, Osprey, FL 34229

  217 Glenwood Ave, Osprey, FL 34229
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  /60

  $11,750,000

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

  1216 N Casey Key Rd, Osprey, FL 34229

  This classically designed estate is privately positioned on north end of Casey Key, considered among the most treasured addresses in Sarasota County. The property spans from a sandy walking beach on the Gulf to a rare covered boat dock on Blackburn Bay. Designed by renowned architect Clifford A. Scholz and built by Delta Southern Construction, over 8,000 square feet designed to celebrate family

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1216 N Casey Key Rd, Osprey, FL 34229
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  /2

  $625,000 Sold Oct 10, 2025

  644 Rivendell Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,298 Sq Ft
  • Built 2001

  Last Sold Summary

  • 16% Below List Price
  • $272/SF
  • 260 Days On Market

  Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  /33

  Est $2,857,206 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 8,763 Sq Ft

  692 Oaks Creek Ct, Osprey, FL 34229

  692 Oaks Creek Ct, Osprey, FL 34229
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  /32

  $159,900

  • 2 Beds
  • 2 Baths
  • 1,031 Sq Ft

  300 Tropic Dr, Osprey, FL 34229

  Welcome to this charming, TURNKEY FURNISHED home in the desirable 55+ cooperative community of The Arbors, where you own your lot and enjoy the benefits of no monthly lot rent! Friendly neighbors and a peaceful setting make this a truly welcoming place to live! Enjoy affordable Florida living in this quaint community, where your neighbors quickly become your friends! Inside, you’ll find an open

  Heidi Lionetti WHITE SANDS REALTY GROUP FL

  300 Tropic Dr, Osprey, FL 34229
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  /2

  $1,400,000 Sold May 07, 2025

  378 MacEwen Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 3,094 Sq Ft
  • Built 1997

  Last Sold Summary

  • 7% Below List Price
  • $452/SF
  • 0 Days On Market

  Current Estimated Value $1,394,188

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  378 MacEwen Dr, Osprey, FL 34229
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  /2

  Est $588,017 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,229 Sq Ft

  825 Oak Pond Dr, Osprey, FL 34229

  825 Oak Pond Dr, Osprey, FL 34229
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  /48

  $225,000

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

  244 Woodland Dr Unit 244, Osprey, FL 34229

  Tranquil Coastal Living in Pine Run244 Woodland Dr, Osprey, FL 34229 Tucked beneath a canopy of mature oaks and palms, this beautifully updated 2-bedroom, 2-bath condo captures the easy, natural rhythm of coastal Florida living. Nestled within the sought-after Pine Run community, it offers both peace and connection just minutes from the beaches of Casey Key, charming Venice, and downtown

  Derek Edwards KELLER WILLIAMS ON THE WATER S

  244 Woodland Dr Unit 244, Osprey, FL 34229
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  /2

  $237,000 Sold Mar 31, 2025

  14 Old Venice Rd, Osprey, FL 34229

  • Land
  • 0.97 Acre
  • $244,330 per Acre

  Last Sold Summary

  • 12% Below List Price
  • 34 Days On Market

  Current Estimated Value $276,241

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  14 Old Venice Rd, Osprey, FL 34229
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  /48

  Est $618,587 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 2,424 Sq Ft

  522 Meadow Sweet Cir, Osprey, FL 34229

  522 Meadow Sweet Cir, Osprey, FL 34229
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  /92

  $1,975,000 Pre-Foreclosure

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

  75 Osprey Point Dr, Osprey, FL 34229

  **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

  Mark Lyda GENEROUS PROPERTY

  75 Osprey Point Dr, Osprey, FL 34229
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  /2

  $744,800 Sold Apr 24, 2025

  448 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,060 Sq Ft
  • Built 2002

  Last Sold Summary

  • 22% Below List Price
  • $243/SF
  • 145 Days On Market

  Current Estimated Value $771,313

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  448 Park Trace Blvd, Osprey, FL 34229
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  /38

  Est $600,632 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,325 Sq Ft

  574 Oak Bay Dr, Osprey, FL 34229

  574 Oak Bay Dr, Osprey, FL 34229
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  /78

  $800,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,134 Sq Ft

  102 Windward Dr, Osprey, FL 34229

  Located in the desirable Southbay Yacht & Racquet Club, this 3-bedroom, 2.5-bath pool home with mature landscaping offers a functional layout and excellent community amenities. The home features a double-door front entry, a spacious great room with cathedral ceiling, an oversized garage, and a large private lot. Interior highlights include double primary bedrooms, tiled walk-in showers in both

  David Cyr WILLIAM RAVEIS REAL ESTATE

  102 Windward Dr, Osprey, FL 34229
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  /2

  $3,525,000 Sold Jun 06, 2025

  275 Lookout Point Dr, Osprey, FL 34229

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

  Last Sold Summary

  • 26% Below List Price
  • $668/SF
  • 124 Days On Market

  Current Estimated Value $3,474,356

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  275 Lookout Point Dr, Osprey, FL 34229
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  /48

  Est $790,419 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,093 Sq Ft

  763 Shadow Bay Way, Osprey, FL 34229

  763 Shadow Bay Way, Osprey, FL 34229
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  /38

  $939,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,802 Sq Ft

  392 Park Trace Blvd, Osprey, FL 34229

  Under contract-accepting backup offers. Set on a premier lakefront lot in Osprey, 392 Park Trace offers serene water views, incredible privacy, and a lifestyle surrounded by nature. Backing to Oscar Scherer State Park and just 1.9 miles from the Gulf waters and waterfront tiki bars, this home embraces Florida living. The Legacy Trail trailhead is only a quarter-mile away, connecting you to miles

  Ryan Skrzypkowski COLDWELL BANKER REALTY

  392 Park Trace Blvd, Osprey, FL 34229
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  /2

  $630,000 Sold Feb 03, 2025

  480 Faith Ave, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,920 Sq Ft
  • Built 1985

  Last Sold Summary

  • 16% Below List Price
  • $328/SF
  • 0 Days On Market

  Current Estimated Value $657,603

  Last Listing Agent Robin Leonardi MICHAEL SAUNDERS & COMPANY

  480 Faith Ave, Osprey, FL 34229
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  /39

  Est $737,626 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft

  1096 Mallard Marsh Dr, Osprey, FL 34229

  1096 Mallard Marsh Dr, Osprey, FL 34229
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  /24

  $624,700

  • Land
  • 0.34 Acre
  • $1,837,353 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

  Matthew Charland LLC GULF SHORES REALTY

  458 N Shore Dr, Osprey, FL 34229
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  /2

  $2,000,000 Sold Apr 21, 2025

  1862 Island Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,598 Sq Ft
  • Built 1982

  Last Sold Summary

  • 18% Below List Price
  • $556/SF
  • 76 Days On Market

  Current Estimated Value $1,952,139

  Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1862 Island Way, Osprey, FL 34229
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  /39

  Est $650,167 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,303 Sq Ft

  680 Shadow Bay Way, Osprey, FL 34229

  680 Shadow Bay Way, Osprey, FL 34229
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  /3

  $89,000

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229

  Hurricane-protected dry storage with top-tier amenities! This slip offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 35, Osprey, FL 34229
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  /2

  $1,350,000 Sold Mar 28, 2025

  409 N Point Rd Unit 704, Osprey, FL 34229

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

  Last Sold Summary

  • 7% Below List Price
  • $486/SF
  • 11 Days On Market

  Current Estimated Value $1,302,983

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 704, Osprey, FL 34229
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  /2

  Est $745,803 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,441 Sq Ft

  1000 Scherer Way, Osprey, FL 34229

  1000 Scherer Way, Osprey, FL 34229
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  /4

  $42,500

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 10.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

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