Osprey, FL Homes

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  /98

  $1,150,000

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft

  1218 Yacht Harbor Dr, Osprey, FL 34229

  New listing alert in the highly sought-after community of Southbay Yacht & Racquet Club, where true resort-style living awaits. The community offers an impressive array of amenities, including a marina, a recently remodeled clubhouse, shuffleboard courts, three tennis courts, four pickleball courts, a bocce ball court, basketball courts, and kayak storage. Residents also enjoy a waterfront park

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 352-2028

  1218 Yacht Harbor Dr, Osprey, FL 34229
• Explore Osprey

• 

  

  

  /49

  $3,500 per month

  • 2 Beds
  • 2 Baths
  • 2,143 Sq Ft
  • Condo for Rent

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Enjoy luxury waterfront living in this beautifully updated 6th-floor condo at Blackburn Harbor Residences on the West side of Tamiami Trail, overlooking the Blackburn bay. This 2-bedroom, 2-bath unit includes a den/flex room and offers panoramic water views from the main rooms. The fully remodeled kitchen features quartz countertops, stainless steel appliances, and two refrigerators—perfect for

  

  Jeremy Myers

  COMPASS PROPERTY MANAGEMENT LLC

  (941) 770-3963

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
• 

  

  /2

  $1,600,000 Sold May 01, 2025

  916 MacEwen Dr, Osprey, FL 34229

  • 5 Beds
  • 7.5 Baths
  • 5,987 Sq Ft
  • Built 1991

  Last Sold Summary

  • 11% Below List Price
  • $267/SF
  • 1 Day On Market

  Current Estimated Value $1,708,589

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
• 

  

  /2

  Est $2,246,339 Not Listed For Sale

  • 5 Beds
  • 5.5 Baths
  • 5,153 Sq Ft

  425 E MacEwen Dr, Osprey, FL 34229

  425 E MacEwen Dr, Osprey, FL 34229
• 

  

  

  /55

  $629,000

  • 4 Beds
  • 2 Baths
  • 2,203 Sq Ft

  583 Pine Ranch East Rd, Osprey, FL 34229

  Beautifully updated 4BR/2BA pool home in the sought-after Bay Oaks Estates community of Osprey. This single-story residence's backyard borders the Legacy Trail and includes a private gate for direct trail access. Inside, high ceilings and natural light complement luxury vinyl plank flooring, fresh paint, new doors, baseboards, and fixtures. The kitchen features quartz countertops, marble

  

  William Fortner

  GALLERY PROPERTIES INTERNATION

  (941) 239-7527

  583 Pine Ranch East Rd, Osprey, FL 34229
• 

  

  /10

  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft
  • Condo for Rent

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229

  ***AVAILABLE NOVEMBER 2025 THRU JANUARY 2026*** Welcome to THE OAK community, it's gated 24/7. private as private can be. Drenched in value and a fantastic community located in South Sarasota. Open plan, easy to show! Close to Siesta Key, Costco restaurants very convenient to all the amenities Sarasota has to offer.

  

  Anthony DeLuca

  AUDREY RAIN RENTALS, INC

  (941) 207-5680

  51 Mac Ewen Dr Unit 1, Osprey, FL 34229
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  /69

  $265,000 Sold May 15, 2025

  360 Pine Run Dr Unit 360, Osprey, FL 34229

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

  Last Sold Summary

  • 16% Below List Price
  • $192/SF
  • 74 Days On Market

  Current Estimated Value $261,533

  Last Listing Agent Priscilla Adams COMPASS FLORIDA LLC

  360 Pine Run Dr Unit 360, Osprey, FL 34229
• 

  /2

  Est $711,555 Not Listed For Sale

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

  356 S Creek Dr, Osprey, FL 34229

  356 S Creek Dr, Osprey, FL 34229
• 

  

  /41

  $330,000

  • 2 Beds
  • 2 Baths
  • 1,165 Sq Ft

  1801 Highland Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Light and bright 2-bedroom, 2-bath townhome in the desirable Town-End Shores community of Osprey! This beautifully maintained home features an open-concept first floor with a spacious living room, dining area, and a Florida room with sliding glass doors for added natural light. The gorgeous kitchen boasts granite countertops, perfect for cooking and

  

  Kimberly Werla

  RE/MAX ALLIANCE GROUP

  (941) 757-8192

  1801 Highland Rd, Osprey, FL 34229
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  /47

  $5,000 per month

  • 2 Beds
  • 2 Baths
  • 1,568 Sq Ft
  • Condo for Rent

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229

  RENTED JANUARY TILL MARCH 2026. TURNKEY FURNISHED RENTAL! GATED, WATER VIEWS! WATERFRONT COMMUNITY IN OSPREY! 2 Bedroom 2 bath plus den. Den has French doors. Lots of light from this second-floor end unit condo. Front door has disappearing screen for fresh Air. TURNKEY FURNISHED. Completely renovated. NO CARPET. Porcelain tile thru out. Granite counters and high ceilings. Front loading washer &

  

  Alba Lange

  WAGNER REALTY

  (941) 207-9375

  293 Hidden Bay Dr Unit 203, Osprey, FL 34229
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  /2

  $452,500 Sold Aug 29, 2025

  784 Sarabay Rd, Osprey, FL 34229

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft
  • Built 1981

  Last Sold Summary

  • 38% Below List Price
  • $287/SF
  • 257 Days On Market

  Current Estimated Value $445,971

  Last Listing Agent Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
• 

  /2

  Est $273,646 Not Listed For Sale

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

  104 Woodland Place, Osprey, FL 34229

  104 Woodland Place, Osprey, FL 34229
• 

  

  /87

  $970,000

  • 3 Beds
  • 3.5 Baths
  • 3,771 Sq Ft

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Waterfront Elegance at Blackburn Harbor! Experience the comfort of a home with the convenience of condo living in this spacious 3-bedroom, 3.5-bath plus den residence offering 3,771 sq. ft. of beautifully designed space and 10-foot tray ceilings throughout and a new roof. Enjoy panoramic water views from the gourmet kitchen, featuring wood

  

  Cynthia Brock

  GULF SANDS REALTY, LLC

  (941) 698-6279

  6100 Jessie Harbor Dr Unit 202, Osprey, FL 34229
• 

  /2

  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft
  • House for Rent

  557 Crane Prairie Way, Osprey, FL 34229

  Welcome to this beautiful fully furnished 3-bed, 2-bath home in the gated community of Willowbend in Osprey. With 2,172 sq ft of bright, open living space, this seasonal rental offers comfort, style, and plenty of room to relax. Enjoy a spacious kitchen, a large primary suite, and a peaceful screened lanai perfect for morning coffee or evening sunsets.The community features a pool, fitness

  

  Craig McCoy

  PREFERRED SHORE LLC

  (941) 392-7290

  557 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  $875,585 Sold Mar 27, 2025

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229

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

  Last Sold Summary

  • 4% Above List Price
  • $452/SF
  • 13 Days On Market

  Current Estimated Value $840,977

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 403, Osprey, FL 34229
• 

  /2

  Est $718,113 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,950 Sq Ft

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229

  260 Hidden Bay Dr Unit B-402, Osprey, FL 34229
• 

  

  /65

  $1,025,000 Pending

  • 4 Beds
  • 4.5 Baths
  • 3,533 Sq Ft

  701 Eaglenook Way, Osprey, FL 34229

  Under contract-accepting backup offers. A truly rare opportunity to own a home on over 2 acres in Osprey, FL. Pine Ranch is a charming enclave of 36 properties with low HOA fees and sensible deed restrictions that offers room for your RV, boat, and space for your horses. Conveniently positioned one mile East of US 41, within a mile of the Legacy Trail and the nationally-ranked Pine View School.

  

  Michael Ballantyne

  COLDWELL BANKER SARASOTA CENT.

  (941) 883-9471

  701 Eaglenook Way, Osprey, FL 34229
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  /44

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft
  • House for Rent

  1308 Thornapple Dr, Osprey, FL 34229

  Welcome home to Willow Bend, a tropical maintenance-free community located in middle of everything southwest Florida has to offer! Gorgeous turnkey 3 bedroom& 2 Bath Furnished annual rental near Nokomis Beach. Peaceful Lake views on an oversized lot. The pretty lanai features travertine marble tile and a HEATED POOL. Many upgrades include quartz kitchen counters, wood plank oak flooring, and

  

  Rachel Tritschler

  RE/MAX ALLIANCE GROUP

  (941) 236-5116

  1308 Thornapple Dr, Osprey, FL 34229
• 

  /2

  $75,000 Sold Dec 12, 2025

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 5% Below List Price
  • 17 Days On Market

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 2, Osprey, FL 34229
• 

  

  /39

  Est $369,077 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  4234 Frontier Ln Unit 101, Osprey, FL 34229

  4234 Frontier Ln Unit 101, Osprey, FL 34229
• 

  

  /93

  $750,000

  • 3 Beds
  • 2 Baths
  • 1,799 Sq Ft

  14041 Bellagio Way Unit 414, Osprey, FL 34229

  Luxury waterfront penthouse with deep water marina access. Discover Osprey Harbor Village, an exclusive gated condo community of only 53 residences perfectly positioned along Florida’s sparkling Intracoastal Waterway. This stunning 3 bedroom, 2 bath penthouse offers nearly 2,000 square feet of thoughtfully designed living space plus a generous 290 square foot tiled terrace with expansive views of

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 297-4970

  14041 Bellagio Way Unit 414, Osprey, FL 34229
• 

  

  /40

  $6,000 per month

  • 2 Beds
  • 3 Baths
  • 1,709 Sq Ft
  • House for Rent

  716 Sarabay Rd, Osprey, FL 34229

  Experience Waterfront Luxury at 716 Sarabay Road, Osprey, FL. Welcome to your private waterfront retreat on Little Sarasota Bay. This stunning 2-bedroom, 3-bath residence offers over 100 feet of direct bay frontage and has been meticulously renovated throughout, combining modern luxury with timeless coastal charm. The open-concept living space is bright and inviting, featuring designer finishes

  

  Mitchell Roberts

  PARADISE REALTY OF VENICE INC

  (941) 241-3260

  716 Sarabay Rd, Osprey, FL 34229
• 

  /2

  $1,050,000 Sold Apr 16, 2025

  247 Keel Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,871 Sq Ft
  • Built 1979

  Last Sold Summary

  • 9% Below List Price
  • $366/SF
  • 70 Days On Market

  Current Estimated Value $1,028,806

  Last Listing Agent Pat Williams PAT WILLIAMS REALTY, LLC

  247 Keel Way, Osprey, FL 34229
• 

  

  /70

  Est $1,086,250 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,346 Sq Ft

  3961 Waypoint Ave, Osprey, FL 34229

  3961 Waypoint Ave, Osprey, FL 34229
• 

  

  /69

  $3,950,000

  • 4 Beds
  • 6 Baths
  • 9,081 Sq Ft

  854 MacEwen Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Set on a private cul-de-sac within The Oaks, this revitalized estate captures the essence of elegant Florida living. From the moment you enter, the home’s light-filled, open design and thoughtful updates make an immediate impression. The main living spaces flow effortlessly from the chef’s kitchen to expansive entertaining areas and out to the

  

  Joe Murphy

  COLDWELL BANKER REALTY

  (941) 394-8350

  854 MacEwen Dr, Osprey, FL 34229
• 

  

  /243

  $1,599 - $3,025 per month

  Alton Osprey

  1 - 3 Beds

  4000 Destination Dr, Osprey, FL 34229

  Now open for immediate move-ins, discover stunning one-, two-, and three-bedroom apartment homes in Osprey, FL. With high-end finishes outfitting each residence, offering the perfect blend of comfort and sophistication, coming home will feel like a daily retreat. Our best-in-class amenity spaces allow you the opportunity to live beyond your expectations - from our sleek business center that works

  4000 Destination Dr, Osprey, FL 34229
• 

  /2

  $925,000 Sold Apr 10, 2025

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Built 2024

  Last Sold Summary

  • $427/SF
  • 31 Days On Market

  Current Estimated Value $906,601

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229
• 

  

  /98

  Est $784,997 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,168 Sq Ft

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229

  250 Hidden Bay Dr Unit A504, Osprey, FL 34229
• 

  

  /48

  $279,000

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

  761 Pine Run Dr, Osprey, FL 34229

  As you step through the gate and into the private courtyard, you’ll immediately feel at home in this beautifully maintained 2-bedroom, 2-bathroom ground-level condominium. Located in one of Sarasota’s most desirable areas west of the trail, this residence offers a perfect blend of comfort, convenience, and timeless architectural design by renowned Frank Folsom Smith.Inside, an open and

  

  Jeffrey Gaudette

  COLDWELL BANKER SARASOTA CENT.

  (941) 759-5875

  761 Pine Run Dr, Osprey, FL 34229
• 

  

  /48

  $4,500 per month

  • 2 Beds
  • 2 Baths
  • 1,335 Sq Ft
  • Condo for Rent

  4243 Expedition Way Unit 4243, Osprey, FL 34229

  AVAILABLE THIS SEASON 2026.***No smoking,no pets permitted. Due at signing - total rent,security deposit,cleaning fee of $350,HOA fee of $150 and sales tax applicable. Heated swimming pool,small club house,gym and cabana across the street from this condo. Positioned perfectly in the highly coveted community of Bay Street Village,this second-story turnkey condo has two bedrooms (king size bed in

  Svatava Jurinova BRIGHT REALTY

  4243 Expedition Way Unit 4243, Osprey, FL 34229
• 

  /2

  $1,750,000 Sold Oct 27, 2025

  627 N MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4.5 Baths
  • 3,857 Sq Ft
  • Built 2000

  Last Sold Summary

  • 10% Below List Price
  • $454/SF
  • 1 Day On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  627 N MacEwen Dr, Osprey, FL 34229
• 

  

  /50

  Est $1,057,529 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,377 Sq Ft

  3973 Waypoint Ave, Osprey, FL 34229

  3973 Waypoint Ave, Osprey, FL 34229
• 

  

  /45

  $3,200,000

  • Land
  • 0.39 Acre
  • $8,205,128 per Acre

  141 N Casey Key Rd, Osprey, FL 34229

  CASEY KEY ISLAND OPPORTUNITY – Bring your preferred builder and create the coastal retreat of your dreams on one of Sarasota County’s most treasured barrier islands. Perfectly positioned on the coveted north end of Casey Key, this exceptional property offers over 100 feet of direct Gulf frontage and sweeping, unobstructed sunset views across shimmering turquoise waters. Your blank canvas awaits –

  

  Julie Larson

  WHITE SANDS REALTY GROUP FL

  (941) 263-0115

  141 N Casey Key Rd, Osprey, FL 34229
• 

  

  /20

  $3,450 per month

  • 2 Beds
  • 2 Baths
  • 936 Sq Ft
  • Condo for Rent

  8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229

  Relax in this stylish 2-bedroom, 2-bathroom retreat just 5 minutes from Nokomis Beach. Feel at home with a private lanai, fast Wi-Fi, a full kitchen, and a Smart TV with Netflix. Perfect for couples, families, or mid-term stays, this apartment is close to Siesta Key, Venice, and St. Armands, comfortably sleeping up to 6 people.Welcome to your Florida retreat, a centrally located 2-bedroom,

  8 Bay Acres Ave Unit ID1228251P, Osprey, FL 34229
• 

  /2

  $650,000 Sold Jul 03, 2025

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $310/SF
  • 246 Days On Market

  Current Estimated Value $661,361

  Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  /53

  Est $559,625 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,133 Sq Ft

  4421 Conchfish Ln, Osprey, FL 34229

  4421 Conchfish Ln, Osprey, FL 34229
• 

  

  /74

  $244,907

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  139 Woodland Place, Osprey, FL 34229

  Here’s a polished real estate listing you can use: --- **Stunning Fully Remodeled 1-Bed / 2-Bath Ground-Floor Condo with Designer Finishes + $15,000 Custom Golf Cart Included** Step into luxury and comfort in this beautifully remodeled ground-floor condo, professionally designed from top to bottom. Every detail has been thoughtfully crafted to create a modern, open-concept living experience

  

  Jack Gang

  GANGWAY REALTY

  (941) 389-1870

  139 Woodland Place, Osprey, FL 34229
• 

  

  /14

  $1,950 per month

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Condo for Rent

  758 Pine Run Dr Unit 758, Osprey, FL 34229

  Welcome to your beautifully updated coastal retreat! This spacious 2-story condo offers 2 bedrooms, 2.5 bathrooms, and a fresh modern design throughout. Perfectly situated in a desirable community just minutes from the beach and with easy access to Blackburn Point Road, this home combines style, comfort, and convenience. Step inside to find a newly remodeled kitchen featuring shaker-style

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  758 Pine Run Dr Unit 758, Osprey, FL 34229
• 

  /2

  $780,000 Sold May 08, 2025

  779 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $362/SF
  • 6 Days On Market

  Current Estimated Value $758,083

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  779 Fordingbridge Way, Osprey, FL 34229
• 

  

  /78

  Est $485,020 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  36 Bishops Court Rd Unit 111, Osprey, FL 34229

  36 Bishops Court Rd Unit 111, Osprey, FL 34229

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