Osprey, FL Homes

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  /64

  Est $297,897 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,839 Sq Ft

  112 Woodland Place, Osprey, FL 34229

  112 Woodland Place, Osprey, FL 34229
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  /66

  $699,000 Open Sun 1AM - 3PM

  • 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 Barrel Tile ROOF (Nov 2025) in Sought After Willowbend----ideally located near the Community Fitness Center, Pool, Pickleball Courts & Playground.....Generous-Sized Living Spaces with Bright/Spacious Open Floor Plan affording ease of INDOOR/OUTDOOR LIVING

  Michael A Martino KELLER WILLIAMS ON THE WATER S

  1303 Thornapple Dr, 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 $385,120 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,304 Sq Ft

  308 Kensey Ln, Osprey, FL 34229

  308 Kensey Ln, Osprey, FL 34229
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  /56

  $999,995

  • 4 Beds
  • 3.5 Baths
  • 2,980 Sq Ft

  1602 Southbay Dr, Osprey, FL 34229

  Welcome to your slice of Florida paradise! Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle. As you arrive, the mature tropical landscaping and stately curb appeal immediately set the tone. Step inside, and you’ll find a generously sized home designed with both relaxation and

  Thomas Kiessling COMPASS FLORIDA LLC

  1602 Southbay Dr, 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 $3,919,749

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

  426 N Casey Key Rd, Osprey, FL 34229
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  /30

  Est $132,721 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  751 Pine Run Dr Unit 751, Osprey, FL 34229

  751 Pine Run Dr Unit 751, Osprey, FL 34229
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  /36

  $595,000

  • 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,

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, 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

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
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  /50

  Est $526,210 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,789 Sq Ft

  529 Meadow Sweet Cir, Osprey, FL 34229

  529 Meadow Sweet Cir, Osprey, FL 34229
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  /55

  $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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  /2

  $1,650,000 Sold Jan 31, 2025

  676 Eagle Watch Ln, Osprey, FL 34229

  • 5 Beds
  • 5.5 Baths
  • 5,399 Sq Ft
  • Built 1992

  Last Sold Summary

  • 8% Below List Price
  • $306/SF
  • 12 Days On Market

  Current Estimated Value $1,745,645

  Last Listing Agent Jamie Mullis COLDWELL BANKER REALTY

  676 Eagle Watch Ln, Osprey, FL 34229
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  /68

  Est $868,905 Not Listed For Sale

  • 6 Beds
  • 3 Baths
  • 3,982 Sq Ft

  1081 Scherer Way, Osprey, FL 34229

  1081 Scherer Way, Osprey, FL 34229
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  /41

  $339,000 Pending

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

  85 Navigation Cir, Osprey, FL 34229

  Under contract-accepting backup offers. The luxury Florida lifestyle you’ve been dreaming of is here! Step into carefree, maintenance-free living in this exceptional 3-bed, 2-bath walk-up condo, perfectly positioned in a highly desirable location. Originally a model home, this 2015 residence is loaded with upgrades and has been meticulously maintained by its one and only owner. Fully furnished

  Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
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  /2

  $435,000 Sold Jan 30, 2025

  393 N Point Rd Unit 302, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Built 2001

  Last Sold Summary

  • 12% Below List Price
  • $212/SF
  • 106 Days On Market

  Current Estimated Value $499,342

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 302, Osprey, FL 34229
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  /37

  Est $863,070 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,023 Sq Ft

  192 Park Trace Blvd, Osprey, FL 34229

  192 Park Trace Blvd, Osprey, FL 34229
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  /84

  $2,550,000 Pending

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

  432 Sorrento Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Experience the ultimate boating lifestyle from this custom-built waterfront home on a peaceful cul-de-sac.Sitting high and dry at 12 feet, the home was fully renovated for it’s current owners in 2020. Built well after the 2002 Florida Building Code changes (which required structures to be engineered for improved hurricane resistance, including impact

  Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
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  /2

  $520,000 Sold Feb 14, 2025

  555 Meadow Sweet Cir, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,680 Sq Ft
  • Built 1997

  Last Sold Summary

  • 5% Below List Price
  • $310/SF
  • 14 Days On Market

  Current Estimated Value $499,829

  Last Listing Agent Jack Keller JACK KELLER INC

  555 Meadow Sweet Cir, Osprey, FL 34229
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  /2

  Est $2,509,820 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 4,937 Sq Ft

  388 Bunker Hill, Osprey, FL 34229

  388 Bunker Hill, Osprey, FL 34229
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  /24

  $499,000

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

  1363 New Forest Ln, Osprey, FL 34229

  Welcome to The Woodlands At Rivendell! This beautiful home is on a large corner lot in the Patio Section of the Woodlands. It has TWO Bedrooms + a DEN, Great Room, double tray ceilings w/ crown molding. The den has double pocket doors! The kitchen is central in the house for entertaining, with plenty of storage, pull-out shelves, and 2 pantries! The Lanai has glimmering water views! Some nice

  Pamela Strom RE/MAX PALM

  1363 New Forest Ln, 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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  /2

  Est $917,572 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,932 Sq Ft

  434 N Shore Dr, Osprey, FL 34229

  434 N Shore Dr, Osprey, FL 34229
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  /63

  $599,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229

  This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof, the elevator was just replaced, and yet the condo dues were just reduced by $500 a quarter! The spacious screened-in balcony overlooks greenery and the

  Per Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  232 Hidden Bay Dr Unit 504, 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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  /29

  Est $2,179,383 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,747 Sq Ft

  162 Puesta Del Sol, Osprey, FL 34229

  162 Puesta Del Sol, Osprey, FL 34229
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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

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  216 Woodland Dr Unit 216, Osprey, FL 34229
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  /84

  Est $1,157,953 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,556 Sq Ft

  513 S Creek Dr, Osprey, FL 34229

  513 S Creek Dr, Osprey, FL 34229
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  /99

  $1,350,000 Pre-Foreclosure

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

  133 Osprey Point Dr, Osprey, FL 34229

  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 is in ideal size to maintain while

  Lisa Warren OWN SRQ LLC

  133 Osprey Point Dr, 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 $999,168

  Last Listing Agent Dena Dominiczak EXIT KING REALTY

  678 Clear Creek Dr, Osprey, FL 34229
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  /2

  Est $224,848 Not Listed For Sale

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

  120 Woodland Place Unit 120, Osprey, FL 34229

  120 Woodland Place Unit 120, Osprey, FL 34229
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  /74

  $1,300,000

  • 4 Beds
  • 3 Baths
  • 2,474 Sq Ft

  700 Faith Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Upon passing the gated pillars of the winding driveway you come upon a hidden treasure. 2.5 Acres of beauty tucked away just off Tamiami and Bay in Osprey. This property backs up to the renowned Pine View school grades 2-12. One of the finest schools in the state and country. The peace and tranquility of the outdoor space is highlighted by a resort

  steve mularky LACEY REALTY INC

  700 Faith Ave, 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 $681,492 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,695 Sq Ft

  1192 Mallard Marsh Dr, Osprey, FL 34229

  1192 Mallard Marsh Dr, Osprey, FL 34229
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  /90

  $795,000

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

  409 N Point Rd Unit 501, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Experience luxury living at The Oaks Preserve. This stunning 3 bedroom, 3 bath corner unit, COMPLETE WITH AN OFFICE, offers the ultimate country club lifestyle. Arrive in style with your private elevator to the 5th floor, where you'll find a pristine residence ready to welcome you. The modern kitchen, featuring stainless steel appliances, a

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 501, 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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  /2

  Est $607,566 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,204 Sq Ft

  685 Clear Creek Dr, Osprey, FL 34229

  685 Clear Creek Dr, Osprey, FL 34229
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  /67

  $995,000

  • 2 Beds
  • 2 Baths
  • 2,071 Sq Ft

  227 Saint James Park, Osprey, FL 34229

  **TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this

  Mark Lyda GENEROUS PROPERTY

  227 Saint James Park, 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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  /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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