Osprey, FL Homes

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  /4

  $39,500

  $3K PRICE DROP

  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 9.5W x 6.5H. With valet boat service,

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

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

  

  /2

  $520,000

  Sold Jun 17, 2026

  1337 Copperwood Dr, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • Built 2004

  Last Sold Summary

  • 13% Below List Price
  • $239/SF
  • 199 Days On Market

  Current Estimated Value $555,365

  Last Listing Agent Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
• 

  

  /2

  Est $635,039

  Not Listed For Sale

  1109 Scherer Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,125 Sq Ft
  • Built 2002

  1109 Scherer Way, Osprey, FL 34229

  Last Sold Summary

  • 61 Days On Market
• 

  

  

  /73

  $999,000

  $51K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 2,486 Sq Ft

  204 Windward Dr, Osprey, FL 34229

  Spacious 3-bedroom, 3-bath home featuring high ceilings and a beautifully updated kitchen designed for both everyday living and entertaining. This home combines comfort and style with light-filled living spaces. Enjoy Florida living at its best with a private pool and amazing lanai area with plenty of covered patio. The oversized two car garage provides plenty of space for a golf cart. Located in

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  204 Windward Dr, Osprey, FL 34229
• 

  

  /2

  $570,000

  Sold Apr 03, 2026

  51 Webb St, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,130 Sq Ft
  • Built 1978

  Last Sold Summary

  • 5% Below List Price
  • $268/SF
  • 6 Days On Market

  Current Estimated Value $573,924

  Last Listing Agent Marina Myers FINE PROPERTIES

  51 Webb St, Osprey, FL 34229
• 

  /2

  Est $278,744

  Not Listed For Sale

  234 Patterson Ave, Osprey, FL 34229

  • 3 Beds
  • 1 Bath
  • 1,173 Sq Ft
  • Built 1979

  234 Patterson Ave, Osprey, FL 34229

  Last Sold Summary

  • 9 Days On Market
• 

  

  /34

  $595,000

  $35K PRICE DROP Pending

  • 3 Beds
  • 3 Baths
  • 1,840 Sq Ft

  408 Park Trace Blvd, Osprey, FL 34229

  Under contract-accepting backup offers. Welcome to your own private oasis in Park Trace Estates, a stunning 3-bedroom, 3-bath single-family home overlooking water with unobstructed views of the Legacy Trail and Oscar Scherer State Park. Located in a desirable community minutes from Pine View School, healthcare, and beaches, this residence is perfectly designed for indoor-outdoor living. The heart

  Jennie Lascelle PREFERRED SHORE LLC

  408 Park Trace Blvd, Osprey, FL 34229
• 

  /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 $1,789,632

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  898 MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $567,376

  Not Listed For Sale

  825 Oak Pond Dr, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,229 Sq Ft
  • Built 1996

  825 Oak Pond Dr, Osprey, FL 34229

  Last Sold Summary

  • 25 Days On Market
• 

  

  /46

  $515,000

  $30K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,293 Sq Ft

  742 Harms Dr, Osprey, FL 34229

  Beautifully renovated and move-in ready, this exceptional property offers the perfect blend of privacy, comfort, and investment potential. Situated on over half an acre along a private, tree-lined street, the home is surrounded by lush tropical landscaping, creating a peaceful oasis just minutes from everything Sarasota has to offer.Step inside to discover a spacious, thoughtfully updated

  Tiffany Stonis EXP REALTY LLC

  742 Harms Dr, Osprey, FL 34229
• 

  /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 $322,304

  Last Listing Agent Kate Kwiecinski COLDWELL BANKER REALTY

  85 Navigation Cir, Osprey, FL 34229
• 

  

  /48

  Est $574,274

  Not Listed For Sale

  522 Meadow Sweet Cir, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 2,424 Sq Ft
  • Built 1998

  522 Meadow Sweet Cir, Osprey, FL 34229

  Last Sold Summary

  • 145 Days On Market
• 

  

  /74

  $1,475,000

  Open Sun 1AM - 3PM

  • 4 Beds
  • 3 Baths
  • 3,246 Sq Ft

  1474 Landview Ln, Osprey, FL 34229

  Elevated luxury throughout this Southbay beauty! Step inside this one of a kind two story home and you will feel like you are at a top resort! You will enter the foyer overlooking the living room and dining room area, just perfect for entertaining highlighting a built-in buffet with wine cooler. Open the sliding glass doors ahead and enter the exquisite out door living area, heated salt water

  Pat Williams PAT WILLIAMS REALTY, LLC

  1474 Landview Ln, 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
• 

  /2

  Est $230,994

  Not Listed For Sale

  225 Woodland Dr, Osprey, FL 34229

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

  225 Woodland Dr, Osprey, FL 34229

  Last Sold Summary

  • 103 Days On Market
• 

  

  /61

  $345,000

  • 2 Beds
  • 2 Baths
  • 1,449 Sq Ft

  89 Navigation Cir, Osprey, FL 34229

  Virtually Staged. Hidden within the gated community of Bay Street Village, this rarely available first-floor waterfront residence blends peaceful lakefront living with the convenience of Sarasota’s vibrant Gulf Coast lifestyle. From tranquil water views and warm Florida sunsets to nearby beaches, dining, shopping, and entertainment, this beautifully positioned condo creates the perfect balance of

  Jozefina Polimirova KW COASTAL LIVING II

  89 Navigation Cir, Osprey, FL 34229
• 

  /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 $3,645,439

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

  426 N Casey Key Rd, Osprey, FL 34229
• 

  

  /38

  Est $559,608

  Not Listed For Sale

  574 Oak Bay Dr, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,325 Sq Ft
  • Built 1999

  574 Oak Bay Dr, Osprey, FL 34229

  Last Sold Summary

  • 7 Days On Market
• 

  

  /60

  $710,000

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

  730 Fordingbridge Way, Osprey, FL 34229

  There’s a quiet kind of beauty in a home that just feels right the moment you walk in, where the light pours through the windows, the spaces flow effortlessly, and every detail invites you to slow down and stay awhile.Welcome to this thoughtfully designed 3-bedroom + den, 2-bath retreat tucked inside the beloved Woodlands at Rivendell. The kind of neighborhood where tree-lined streets and

  Christina Gaskill COLDWELL BANKER REALTY

  730 Fordingbridge Way, Osprey, FL 34229
• 

  /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 $3,523,883

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  431 Yacht Harbor Dr, Osprey, FL 34229
• 

  /2

  Est $940,189

  Not Listed For Sale

  32 Bayhead Ln, Osprey, FL 34229

  • 3 Beds
  • 3.5 Baths
  • 2,570 Sq Ft
  • Built 1993

  32 Bayhead Ln, Osprey, FL 34229

  Last Sold Summary

  • 82 Days On Market
• 

  

  /96

  $2,995,000

  Open Sat 1PM - 4PM $255K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 2,665 Sq Ft

  14401 Masthead Dr, Osprey, FL 34229

  Unobstructed bayfront views and refined coastal luxury define this exceptional waterfront residence in the gated Bayside community. Custom-built in 2017 by Rob Allegra and ideally positioned on a private cul-de-sac between Sarasota and Venice, this home offers a rare opportunity to experience the best of Florida’s Gulf Coast lifestyle. Sweeping views of the Bay and Intracoastal Waterway greet you

  Mackenzie Longueuil MICHAEL SAUNDERS & COMPANY

  14401 Masthead Dr, Osprey, FL 34229
• 

  /2

  $535,000

  Sold Jun 03, 2026

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft
  • Built 1999

  Last Sold Summary

  • 9% Below List Price
  • $277/SF
  • 100 Days On Market

  Current Estimated Value $548,810

  Last Listing Agent Susan Retzke RE/MAX PALM

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
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  /48

  Est $739,479

  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

  • 22 Days On Market
• 

  

  /40

  $3,995,000

  $255K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,389 Sq Ft

  324 Bayshore Dr, Osprey, FL 34229

  Big bay views surround you from this exquisitely updated waterfront estate. Welcome to 324 Bayshore Drive, a property of nearly half an acre set on a large, open stretch of the bay with easy access to the Intracoastal Waterway. Even more spectacular is the beautiful water and natural beauty of Midnight Pass which is just to the north of this property and sandbar relaxation just a short boat ride

  Drew Russell MICHAEL SAUNDERS & COMPANY

  324 Bayshore Dr, Osprey, FL 34229
• 

  /2

  $530,000

  Sold Jun 11, 2026

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,040 Sq Ft
  • Built 2005

  Last Sold Summary

  • 3% Below List Price
  • $260/SF
  • 31 Days On Market

  Current Estimated Value $536,478

  Last Listing Agent Christine Green COLDWELL BANKER REALTY

  1116 Beachcomber Ct Unit 3, Osprey, FL 34229
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  /69

  Est $252,649

  Not Listed For Sale

  360 Pine Run Dr Unit 360, Osprey, FL 34229

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

  360 Pine Run Dr Unit 360, Osprey, FL 34229

  Last Sold Summary

  • 74 Days On Market
• 

  

  /42

  $609,900

  • 3 Beds
  • 2 Baths
  • 2,047 Sq Ft

  619 Oak River Ct, Osprey, FL 34229

  Virtually Staged. Back on the market due to buyer financing. Move-in ready Bay Oaks pool home featuring a beautifully renovated kitchen, stunning spa-inspired primary bath, updated flooring, and a huge private fenced backyard. Situated on an oversized 0.38-acre corner lot, this home offers the perfect combination of modern updates, privacy, and outdoor living. Welcome to this thoughtfully

  Ross Fishman FISHMAN GROUP REALTY LLC

  619 Oak River Ct, Osprey, FL 34229
• 

  /2

  $1,265,000

  Sold Jun 01, 2026

  1471 Shoal Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 2,798 Sq Ft
  • Built 1985

  Last Sold Summary

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

  Current Estimated Value $1,474,331

  Last Listing Agent Lauren Doyle DALTON WADE INC

  1471 Shoal Way, Osprey, FL 34229
• 

  

  /39

  Est $715,780

  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

  • 39 Days On Market
• 

  

  /65

  $6,475,000

  $625K PRICE DROP

  • 5 Beds
  • 5.5 Baths
  • 4,096 Sq Ft

  121 N Casey Key Rd, Osprey, FL 34229

  Gulf Front, private beach. This sun-drenched Florida villa captures the character of a Mexican hacienda with the ease of tropical coastal living. Smooth stucco exteriors, clay tile roofing, and vibrant bougainvillea frame a private courtyard, setting the tone for a home that is both timeless and inviting.Directly on the turquoise waters of the Gulf, this newly remodeled residence on the north

  Lisa Napolitano DOUGLAS ELLIMAN

  121 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $164,000

  Sold May 14, 2026

  200 Woodland Dr Unit 200, Osprey, FL 34229

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft
  • Built 1980

  Last Sold Summary

  • 6% Below List Price
  • $190/SF
  • 45 Days On Market

  Current Estimated Value $175,490

  Last Listing Agent Kathleen Griffin MICHAEL SAUNDERS & COMPANY

  200 Woodland Dr Unit 200, Osprey, FL 34229
• 

  /2

  Est $752,384

  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

  • 54 Days On Market
• 

  

  /62

  $1,100,000

  $100K PRICE DROP

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

  385 N Point Rd Unit 304, Osprey, FL 34229

  **MAGNIFICENTLY UPDATED, EXPANSIVE CORNER CONDO RESIDENCE OFFERING NEARLY 2,800 SQ FT OF REFINED LIVING SPACE** features 3 Bedrooms, 3 Full Baths, PLUS a Study/Den (or optional 4th bedroom with walk-in closet), all nestled behind the secure gates of the highly sought-after Oaks Preserve Country Club community. Step off your private elevator foyer into a brilliantly renovated, light-filled

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 304, Osprey, FL 34229
• 

  /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 $2,330,317

  Last Listing Agent Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
• 

  /2

  Est $633,372

  Not Listed For Sale

  519 Habitat Blvd, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,234 Sq Ft
  • Built 2003

  519 Habitat Blvd, Osprey, FL 34229

  Last Sold Summary

  • 15 Days On Market
• 

  

  /42

  $235,000

  $65K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft

  51 MacEwen Dr Unit 11, Osprey, FL 34229

  Withing the prestigious The Oaks Golf and Country Club, at the Windsor Lodge, this second-floor, maintenance-free, lakeside efficiency features a covered balcony with views of the lake, pool, and golf course. Elevator access to the second floor. Short-term rentals permitted.As an investment, as a weekend get-away or for visiting family and friends:Enjoy the country club lifestyle at The

  Sabine Spycher 342 REAL ESTATE

  51 MacEwen Dr Unit 11, Osprey, FL 34229
• 

  /2

  $285,000

  Sold May 22, 2026

  4173 Frontier Ln, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Built 2019

  Last Sold Summary

  • 1% Below List Price
  • $251/SF
  • 3 Days On Market

  Current Estimated Value $288,687

  Last Listing Agent Michael A Martino KELLER WILLIAMS ON THE WATER S

  4173 Frontier Ln, Osprey, FL 34229
• 

  

  /55

  Est $570,332

  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

  • 363 Days On Market
• 

  

  /86

  $655,000

  $30K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  57 Bishops Court Rd Unit 121, Osprey, FL 34229

  Enjoy the perfect maintenance free country club lifestyle in the charming and quaint Bishopscourt Townhomes located in The Oaks Preserve. Architecturally designed, this classic Georgian style townhouse features two bedrooms, two full ensuite baths, one half bath, a spacious great room, and a large terrace overlooking a lake. A welcoming foyer leads to the expansive great room where high ceilings,

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  57 Bishops Court Rd Unit 121, Osprey, FL 34229

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