Osprey, FL Homes

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  $1,015,000 Sold Aug 01, 2025

  678 Clear Creek Dr, Osprey, FL 34229

  • 5 Beds
  • 3 Baths
  • 3,912 Sq Ft
  • Built 2002

  Last Sold Summary

  • 8% Below List Price
  • $259/SF
  • 11 Days On Market

  Current Estimated Value $1,001,696

  Last Listing Agent Dena Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  Est $669,512 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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  $799,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,617 Sq Ft

  529 Habitat Blvd, Osprey, FL 34229

  Under contract-accepting backup offers. This stunning Monterey model, crafted by Lee Wetherington, is a rare find in the sought-after, maintenance-free community of Willowbend. With exceptional curb appeal and one of the largest lots in the area, this residence boasts panoramic lake views with nearly 140 feet of lakefront, all on a peaceful cul-de-sac. Recently upgraded with a pool, spa and

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  529 Habitat Blvd, Osprey, FL 34229
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  $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

  Current Estimated Value $1,178,761

  Last Listing Agent Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
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  Est $751,814 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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  $2,350,000

  • 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
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  $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

  Current Estimated Value $1,290,653

  Last Listing Agent Lore Miller RESULTS REALTY GROUP LLC

  364 Renoir Dr, Osprey, FL 34229
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  /11

  Est $303,889 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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  $614,900

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

  510 Latitude Ln, Osprey, FL 34229

  Stunning residence crafted by renowned builder Lee Wetherington. Nestled on a southern exposure, maintenance-free landscaped lot, this home offers the perfect blend of style, comfort, and functionality. Interior Highlights-Architectural Elegance: High tray ceilings, extensive crown molding, and built-in shelving throughout.Gourmet Kitchen: Stainless steel appliances, natural gas cooking,

  Marisa Marino BRIGHT REALTY

  510 Latitude Ln, Osprey, FL 34229
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  $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 $922,140

  Last Listing Agent Lisa Napolitano DOUGLAS ELLIMAN

  128 Sea Anchor Dr, Osprey, FL 34229
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  /2

  Est $600,632 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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  $749,900 Pending

  • 4 Beds
  • 3 Baths
  • 2,551 Sq Ft

  319 Park Trace Blvd, Osprey, FL 34229

  Under contract-accepting backup offers. Welcome to your dream home in a prime location, positioned near A-rated schools such as Pine View, world-class beaches, premier shopping and exceptional dining. This spacious four-bedroom, three-bath residence offers almost 2,600 square feet of living space, blending comfort and elegance at every turn. The home is filled with beautiful finishing touches,

  Megan George PREMIER SOTHEBYS INTL REALTY

  319 Park Trace Blvd, Osprey, FL 34229
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  $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 $2,589,890

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  478 Oriskany Ct, Osprey, FL 34229
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  /48

  Est $622,217 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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  /19

  $433,000

  • 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 pool Conveniently located between Sarasota, Siesta Key, Venice, and the Gulf Beaches.Walking distance to Casey Key Mainland (Chef Rolfs),

  Stephen Hachey REALTY OF RIVERVIEW LLC

  1811 Highland Rd, Osprey, FL 34229
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  $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

  Current Estimated Value $1,432,383

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  402 Walls Way, Osprey, FL 34229
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  Est $602,370 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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  $400,000 Pending

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

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229

  Under contract-accepting backup offers. RARELY AVAILABLE FIRST FLOOR END-UNIT in the 12-acre waterfront resort-style gated community of Hidden Bay - move-in ready and fully furnished for an easy Florida lifestyle. This open-concept 2-bedroom, 2-bath home with a flex space offers newer luxury vinyl flooring, a bright and spacious kitchen and a large pantry, and a charming breakfast nook framed by

  Stephanie Ham PARADISE EXCLUSIVE INC

  291 Hidden Bay Dr Unit 101, Osprey, FL 34229
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  $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

  Current Estimated Value $629,092

  Last Listing Agent Veronica Manes MICHAEL SAUNDERS & COMPANY

  644 Rivendell Blvd, Osprey, FL 34229
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  Est $798,763 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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  $2,450,000 Open Sun 12PM - 3PM

  • 4 Beds
  • 5.5 Baths
  • 4,858 Sq Ft

  896 MacEwen Dr, Osprey, FL 34229

  This beautiful custom designed home will captivate you from the moment you enter the front door. Located in the extremely sought after Oaks Country Club, this recently renovated home is sure to impress with picturesque views of the golf course. Privacy and entertaining are at the top of the list for this tastefully remodeled home, offering 4 bedrooms and 5 1⁄2 baths. Marble and wood floors are in

  Marisa Marino BRIGHT REALTY

  896 MacEwen Dr, Osprey, FL 34229
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  $675,000 Sold Jan 21, 2026

  409 N Point Rd Unit 501, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2004

  Last Sold Summary

  • 36% Below List Price
  • $260/SF
  • 575 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 501, Osprey, FL 34229
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  Est $726,118 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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  $1,100,000

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

  401 N Point Rd Unit 504, Osprey, FL 34229

  FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you

  Mary Elizabeth Mock COLDWELL BANKER REALTY

  401 N Point Rd Unit 504, Osprey, FL 34229
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  $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 $1,403,414

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  378 MacEwen Dr, Osprey, FL 34229
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  Est $645,586 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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  $699,000

  • 3 Beds
  • 2 Baths
  • 1,929 Sq Ft

  1303 Thornapple Dr, Osprey, FL 34229

  INCREDIBLE Pool Home in INCREDIBLE Community!...You Will Be Impressed by this Well-Appointed FURNISHED Lee Wetherington residence with NEW $54,000 Barrel Tile ROOF (Nov 2025) in Sought After Willowbend---- A MAINTENANCE-FREE (lawn/landscaping/irrigation) Boutique Community ideally located near the Fitness Center and Community Pool, Pickleball Courts & Playground.....Generous-Sized Living Spaces

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, Osprey, FL 34229
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  $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 $273,877

  Last Listing Agent Glenn Davis COLDWELL BANKER SARASOTA CENT.

  14 Old Venice Rd, Osprey, FL 34229
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  Est $743,899 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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  $580,000

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft

  1337 Copperwood Dr, Osprey, FL 34229

  This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
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  $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 $776,815

  Last Listing Agent Toni Zarghami KW COASTAL LIVING III

  448 Park Trace Blvd, Osprey, FL 34229
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  Not Listed For Sale

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

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
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  $525,000

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  120 Villa Dr Unit 120, Osprey, FL 34229

  Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  120 Villa Dr Unit 120, Osprey, FL 34229
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  $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 $3,485,999

  Last Listing Agent Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  275 Lookout Point Dr, Osprey, FL 34229
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  Est $553,112 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  590 Oak Bay Dr, Osprey, FL 34229

  590 Oak Bay Dr, Osprey, FL 34229
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  $175,000

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  200 Woodland Dr Unit 200, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to Pine Run in Osprey! Half-way between Sarasota and Venice, convenient to both with ample shopping and dining close by. Your 1 bedroom one and a half bath oasis is nestled on 20+ acres of lush native Florida landscape. This popular ground floor unit features large glass sliders and your own private courtyard in the front of the unit where

  Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  200 Woodland Dr Unit 200, Osprey, FL 34229
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  $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 $1,957,127

  Last Listing Agent Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1862 Island Way, Osprey, FL 34229
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  Est $175,173 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  701 Pine Run Dr, Osprey, FL 34229

  701 Pine Run Dr, Osprey, FL 34229
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  $625,000

  • 3 Beds
  • 2 Baths
  • 2,162 Sq Ft

  767 Fordingbridge Way, Osprey, FL 34229

  Set on a quiet cul-de-sac in The Woodlands at Rivendell, this furnished and thoughtfully maintained residence offers a peaceful setting surrounded by mature landscaping and wooded views. The extended foyer welcomes you into an open great-room layout spanning nearly 2,200 square feet, where high tray ceilings, plantation shutters, and hardwood flooring create a cohesive flow throughout the main

  Roger Pettingell COLDWELL BANKER REALTY

  767 Fordingbridge Way, Osprey, FL 34229
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  $520,000 Sold Dec 30, 2025

  447 Oak Point Rd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,688 Sq Ft
  • Built 1994

  Last Sold Summary

  • 5% Below List Price
  • $193/SF
  • 49 Days On Market

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  447 Oak Point Rd, Osprey, FL 34229

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