Osprey, FL Homes

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  /48

  Est $763,150 Not Listed For Sale

  763 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,093 Sq Ft
  • Built 1998

  763 Shadow Bay Way, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $278/SF
  • 22 Days On Market

  Last Sold Price $860,000

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /94

  $990,000

  • 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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  /2

  $879,352 Sold Apr 15, 2025

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Built 2024

  Last Sold Summary

  • 4% Above List Price
  • $454/SF
  • 14 Days On Market

  Current Estimated Value $818,873

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 402, Osprey, FL 34229
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  /39

  Est $721,354 Not Listed For Sale

  1096 Mallard Marsh Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft
  • Built 2000

  1096 Mallard Marsh Dr, Osprey, FL 34229

  Last Sold Summary

  • 5% Below List Price
  • $305/SF
  • 39 Days On Market

  Last Sold Price $760,000

  Last Listing Agent Barbara Gahry COLDWELL BANKER SARASOTA CENT.
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  /66

  $674,900 Pending

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

  1303 Thornapple Dr, Osprey, FL 34229

  Under contract-accepting backup offers. 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 &

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, Osprey, FL 34229
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  /2

  $1,700,000 Sold Sep 18, 2025

  898 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 4,132 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $411/SF
  • 0 Days On Market

  Current Estimated Value $1,739,007

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  898 MacEwen Dr, Osprey, FL 34229
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  /2

  Est $740,211 Not Listed For Sale

  1000 Scherer Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,441 Sq Ft
  • Built 2003

  1000 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • $309/SF
  • 54 Days On Market

  Last Sold Price $755,000

  Last Listing Agent Jody Callan PREMIER SOTHEBYS INTL REALTY
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  /36

  $550,000 Open Sat 1PM - 3PM

  • 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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  /2

  $329,000 Sold Jan 14, 2026

  85 Navigation Cir, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft
  • Built 2014

  Last Sold Summary

  • 3% Below List Price
  • $230/SF
  • 8 Days On Market

  Current Estimated Value $325,661

  Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
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  /55

  Est $557,396 Not Listed For Sale

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Built 2004

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Last Sold Summary

  • 13% Below List Price
  • $298/SF
  • 363 Days On Market

  Last Sold Price $638,000

  Last Listing Agent Jeremy Myers COMPASS PROPERTY MANAGEMENT LLC
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  /56

  $599,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft

  51 Webb St, Osprey, FL 34229

  Under contract-accepting backup offers. Location, location, location. Nestled west of the Trail in the heart of Osprey, this beautifully updated three-bedroom, two-bath home with a den offers a rare opportunity just moments from Sarasota Bay. Set on a spacious, private lot framed by mature oak trees and lush tropical landscaping, the property features no HOA or CDD restrictions. Inside, the home

  Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
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  /2

  $155,000 Sold Nov 26, 2025

  170 Edgewood Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 959 Sq Ft
  • Built 1979

  Last Sold Summary

  • 6% Below List Price
  • $162/SF
  • 132 Days On Market

  Last Listing Agent Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
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  /2

  Est $542,845 Not Listed For Sale

  590 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft
  • Built 1999

  590 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 11% Below List Price
  • $322/SF
  • 53 Days On Market

  Last Sold Price $609,000

  Last Listing Agent Kathy White PREFERRED SHORE LLC
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  /55

  $510,000

  • 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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  /2

  $3,900,000 Sold Aug 27, 2025

  426 N Casey Key Rd, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,876 Sq Ft
  • Built 1992

  Last Sold Summary

  • 20% Below List Price
  • $2,079/SF
  • 657 Days On Market

  Current Estimated Value $3,584,278

  Last Listing Agent Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  426 N Casey Key Rd, Osprey, FL 34229
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  /46

  Est $613,730 Not Listed For Sale

  730 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,182 Sq Ft
  • Built 2002

  730 Fordingbridge Way, Osprey, FL 34229

  Last Sold Summary

  • 9% Below List Price
  • $309/SF
  • 128 Days On Market

  Last Sold Price $675,000

  Last Listing Agent Michelle Hupp KELLER WILLIAMS ISLAND LIFE REAL ESTATE
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  /42

  $200,000

  • 2 Beds
  • 2 Baths
  • 1,223 Sq Ft

  211 Woodland Dr Unit 211, Osprey, FL 34229

  Tucked away in the charming community of Pine Run, this uniquely designed two-story condo offers the perfect blend of privacy, comfort, and Florida lifestyle living in the heart of Osprey. This spacious 2-bedroom, 2-bath residence features a layout offering the primary suite on the first floor—ideal for ease of living and added privacy. The main level offers an inviting living and dining area

  Samantha Campbell BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE

  211 Woodland Dr Unit 211, Osprey, FL 34229
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  /2

  $3,500,000 Sold Dec 17, 2025

  431 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 3,006 Sq Ft
  • Built 1979

  Last Sold Summary

  • 19% Below List Price
  • $1,164/SF
  • 11 Days On Market

  Current Estimated Value $3,539,892

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
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  /2

  Est $758,026 Not Listed For Sale

  356 S Creek Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,369 Sq Ft
  • Built 1990

  356 S Creek Dr, Osprey, FL 34229

  Last Sold Summary

  • 4% Above List Price
  • $308/SF
  • 36 Days On Market

  Last Sold Price $730,000

  Last Listing Agent Christiana Kopetzky Michael Saunders
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  /37

  $1,499,000 Pending

  • 4 Beds
  • 3 Baths
  • 2,798 Sq Ft

  1471 Shoal Way, Osprey, FL 34229

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. This exceptional residence truly checks every box.Designed by a renowned architect for his own family, 1471 Shoal Way is a masterclass in thoughtful design, quality craftsmanship, and effortless livability. Set on one of the largest lots in Southbay (just shy of half an acre) privacy was a guiding

  Lauren Doyle DALTON WADE INC

  1471 Shoal Way, Osprey, FL 34229
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  /2

  $2,400,000 Sold Jan 09, 2026

  432 Sorrento Dr, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 3,640 Sq Ft
  • Built 2007

  Last Sold Summary

  • 6% Below List Price
  • $659/SF
  • 7 Days On Market

  Current Estimated Value $2,333,492

  Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
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  /81

  Est $1,130,970 Not Listed For Sale

  385 N Point Rd Unit 604, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  385 N Point Rd Unit 604, Osprey, FL 34229

  Last Sold Summary

  • 16% Below List Price
  • $486/SF
  • 48 Days On Market

  Last Sold Price $1,350,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  /35

  $175,000 Pending

  • 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

  $470,000 Sold Feb 10, 2026

  1363 New Forest Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,738 Sq Ft
  • Built 2002

  Last Sold Summary

  • 14% Below List Price
  • $270/SF
  • 260 Days On Market

  Current Estimated Value $473,385

  Last Listing Agent Pamela Strom RE/MAX PALM

  1363 New Forest Ln, Osprey, FL 34229
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  /21

  Est $1,265,731 Not Listed For Sale

  1108 Bayhead Ln, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,541 Sq Ft
  • Built 1997

  1108 Bayhead Ln, Osprey, FL 34229

  Last Sold Summary

  • 58% Above List Price
  • $226/SF
  • 99 Days On Market

  Last Sold Price $800,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  /45

  $599,000 Pending

  • 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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  /2

  $649,000 Sold Aug 26, 2025

  0 Four Knot Ln, Osprey, FL 34229

  • Land
  • 0.26 Acre
  • $2,496,154 per Acre

  Last Sold Summary

  • 4 Days On Market

  Last Listing Agent Gregory Wood CERUS REALTY

  0 Four Knot Ln, Osprey, FL 34229
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  /50

  Est $1,844,581 Not Listed For Sale

  280 Saratoga Ct, Osprey, FL 34229

  • 4 Beds
  • 3.5 Baths
  • 3,970 Sq Ft
  • Built 1994

  280 Saratoga Ct, Osprey, FL 34229

  Last Sold Summary

  • 3% Above List Price
  • $450/SF
  • 41 Days On Market

  Last Sold Price $1,787,500

  Last Listing Agent Mark Lyda GENEROUS PROPERTY
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  /44

  $445,000 Pending

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

  288 Woods Point Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Perfectly positioned West of the Trail near Blackburn Point and Casey Key, this turnkey furnished 3 bedroom, 2 bathroom attached single family residence offers nearly 1,800 square feet of vaulted, light-filled interiors framed by lush preserve views. Set within an exclusive enclave of just 44 homes, this residence delivers the privacy and proportions of

  Toni Zarghami KW COASTAL LIVING III

  288 Woods Point Rd, Osprey, FL 34229
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  /2

  $43,000 Sold Nov 04, 2025

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229

  Last Sold Summary

  • 2% Below List Price
  • 98 Days On Market

  Last Listing Agent Rick Bumbaca NORTHGROUP REAL ESTATE, INC

  570 Blackburn Point Rd Unit 6, Osprey, FL 34229
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  /88

  Est $550,658 Not Listed For Sale

  578 Meadow Sweet Cir, Osprey, FL 34229

  • 2 Beds
  • 2.5 Baths
  • 1,978 Sq Ft
  • Built 2000

  578 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 8% Below List Price
  • $303/SF
  • 43 Days On Market

  Last Sold Price $600,000

  Last Listing Agent Rosalie Phillips Michael Saunders
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  /2

  $489,249 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, Osprey, FL 34229

  Under Construction. UNDER CONSTRUCTION STARTING FROM THE UPPER $400,000. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 102, Osprey, FL 34229
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  /2

  $220,000 Sold Oct 23, 2025

  216 Woodland Dr Unit 216, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft
  • Built 1980

  Last Sold Summary

  • 10% Below List Price
  • $166/SF
  • 55 Days On Market

  Current Estimated Value $215,147

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  216 Woodland Dr Unit 216, Osprey, FL 34229
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  /2

  Est $250,762 Not Listed For Sale

  707 Pine Run Dr, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,379 Sq Ft
  • Built 1973

  707 Pine Run Dr, Osprey, FL 34229

  Last Sold Summary

  • 14% Below List Price
  • $210/SF
  • 134 Days On Market

  Last Sold Price $290,000

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC
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  /99

  $1,350,000 Pending

  • 4 Beds
  • 3 Baths
  • 3,679 Sq Ft

  133 Osprey Point Dr, Osprey, FL 34229

  Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Custom Home located in the exclusive gated community of The Oaks Bayside with a private pool and spa. Just across the street from Sarasota Bay. Recent improvements include updated bathrooms and a newer kitchen (with Thermador appliances) and all freshly painted. This 4 bedroom, 3 bathroom plus bonus room house

  Lisa Warren OWN SRQ LLC

  133 Osprey Point Dr, Osprey, FL 34229
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  /2

  $660,000 Sold Mar 10, 2026

  471 Park Trace Blvd, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,267 Sq Ft
  • Built 2001

  Last Sold Summary

  • 12% Below List Price
  • $291/SF
  • 197 Days On Market

  Current Estimated Value $691,170

  Last Listing Agent Bill Cantrell WILLIAM RAVEIS REAL ESTATE

  471 Park Trace Blvd, Osprey, FL 34229
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  /13

  Est $350,705 Not Listed For Sale

  316 Pennsylvania Ave, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 2002

  316 Pennsylvania Ave, Osprey, FL 34229

  Last Sold Summary

  • 7% Below List Price
  • $363/SF
  • 376 Days On Market

  Last Sold Price $377,500

  Last Listing Agent Miranda Platt, PA RELAX PROPERTY GROUP, LLC
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  /80

  $269,000

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

  135 Woodland Place, Osprey, FL 34229

  Ideally located in the heart of Osprey, this private corner, first floor condo offers effortless Florida living just minutes from pristine Gulf beaches and less than half a mile from the Intracoastal Waterway. The sought after community at the entrance to Casey Key was designed to live in harmony with nature by Frank Folsum Smith of the Sarasota School of Architecture. This unit features a garden

  Kim Azar-Calka MICHAEL SAUNDERS & COMPANY

  135 Woodland Place, Osprey, FL 34229
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  /2

  $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 $981,003

  Last Listing Agent Dena Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /22

  Est $552,287 Not Listed For Sale

  743 Anna Hope Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,150 Sq Ft
  • Built 2000

  743 Anna Hope Ln, Osprey, FL 34229

  Last Sold Summary

  • $256/SF
  • 177 Days On Market

  Last Sold Price $550,000

  Last Listing Agent Roger Pettingell COLDWELL BANKER REALTY

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