Osprey, FL Homes

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  /88

  $1,200,000

  • 4 Beds
  • 3 Baths
  • 3,379 Sq Ft

  201 Eaglenook Way, Osprey, FL 34229

  Nestled in the exclusive Pine Ranch community of Osprey, Florida, this 4-bedroom, 3-bath estate offers a rare opportunity for those seeking privacy, tranquility, and a healthier way of living. Situated on just over two acres of lush, tree-canopied land, this meticulously maintained home is designed for comfort, sustainability, and connection to nature. From the moment you enter the long private

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 757-8209

  201 Eaglenook Way, Osprey, FL 34229
• 

  Explore Osprey

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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

  $1,500,000 Sold Sep 19, 2025

  • 2,611 Sq Ft
  • $574/SF
  • 29 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1998

  462 E MacEwen Dr, Osprey, FL 34229

  This completely remodeled home in The Oaks Clubside, set on nearly an acre of mature, meticulously landscaped grounds, is pure perfection. Nestled behind the gates of The Oaks Clubside, this residence is a masterful blend of classic elegance and contemporary sophistication. Arriving at the property, you are greeted by a striking full-circle driveway—a graceful approach that not only enhances the

  Steve Abbe COLDWELL BANKER REALTY

  462 E MacEwen Dr, Osprey, FL 34229
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  /39

  Est $382,930 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
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  /83

  $1,999,000

  • 4 Beds
  • 5 Baths
  • 4,020 Sq Ft

  67 Sugar Mill Dr, Osprey, FL 34229

  This is your rare chance to claim a spectacular estate in Sarasota’s premier golf and country club community THE OAKS. This elegant home seamlessly blends timeless architecture with resort-style living. Beyond the private gates, step into over 4,000 square feet of refined interiors featuring dramatic ceilings, architectural columns, and panoramic views. The expansive layout includes 4 bedrooms, 5

  

  Paula Mapp

  MAPP REALTY & INVESTMENT CO

  (941) 294-4414

  67 Sugar Mill Dr, Osprey, FL 34229
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  /49

  $3,800 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
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  /2

  $2,625,000 Sold Sep 16, 2025

  • 5,778 Sq Ft
  • $454/SF
  • 10 Days On Market

  • 4 Beds
  • 7 Baths
  • Built 1999

  478 Oriskany Ct, Osprey, FL 34229

  Welcome to your dream home, a sanctuary of elegance and comfort nestled on an exclusive, private street with only nine residences and no neighbors across the way—just the tranquility of a natural preserve. This remarkable property in The Oaks Clubside, with 4 bedrooms, 5 full bathrooms, and 2 half baths, boasts impact windows and doors throughout, providing peace of mind and a quiet, secure

  Steve Abbe COLDWELL BANKER REALTY

  478 Oriskany Ct, Osprey, FL 34229
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  /70

  Est $1,125,056 Not Listed For Sale

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

  3961 Waypoint Ave, Osprey, FL 34229

  3961 Waypoint Ave, Osprey, FL 34229
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  /100

  $625,000

  • 3 Beds
  • 2 Baths
  • 1,736 Sq Ft

  14041 Bellagio Way Unit 315, Osprey, FL 34229

  SIGNIFICANT PRICE IMPROVEMENT! IF YOU HAVE BEEN WAITING FOR A FANTASTIC WATERFRONT PROPERTY AND PRICE.. THIS IS THE ONE! Step into waterfront luxury living at its finest in Osprey Harbor Village, a coastal gem perfectly situated between Sarasota and Venice, offering easy access to Siesta Key, Nokomis Beach, and Venice Beach. This sought-after marina community is the epitome of elegance and the

  

  Dawn Bear

  WILLIAM RAVEIS REAL ESTATE

  (941) 207-5944

  14041 Bellagio Way Unit 315, Osprey, FL 34229
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  /269

  $1,599 - $3,025 per month

  Alton Osprey

  1 - 3 Beds

  4000 Destination Dr, Osprey, FL 34229

  Arriving Spring 2025, discover stunning one-, two-, and three-bedroom apartment homes coming to 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 for

  4000 Destination Dr, Osprey, FL 34229
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  /2

  $527,500 Sold Sep 11, 2025

  • 1,952 Sq Ft
  • $270/SF
  • 60 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229

  Welcome to the exclusive Blackburn Point Marina Village – where luxury meets convenience in one of Sarasota's desirable waterfront communities! This rarely available, beautifully appointed townhome offers the best of maintenance-free, coastal living in a gated community featuring resort-style amenities including a heated pool, cabana, tiki bar, and more. Enjoy peace of mind with a new roof (2025)

  Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
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  /82

  Est $717,086 Not Listed For Sale

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

  250 Hidden Bay Dr Unit A-201, Osprey, FL 34229

  250 Hidden Bay Dr Unit A-201, Osprey, FL 34229
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  /59

  $1,150,000

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

  701 Eaglenook Way, Osprey, FL 34229

  Located in the desirable Pine Ranch community, 701 Eaglenook Way offers 4 bedrooms, 4.5 bathrooms, and 3,533 sq ft of interior space. Set on 2.2 acres in a private, deed-restricted neighborhood where horses are permitted, this property provides generous space and functionality in a peaceful setting. A barn/garage outbuilding on the lot offers added flexibility for storage or other use.A

  

  Michael Ballantyne

  COLDWELL BANKER SARASOTA CENT.

  (941) 883-9471

  701 Eaglenook Way, Osprey, FL 34229
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  /41

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,391 Sq Ft
  • Condo for Rent

  2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229

  ANNUAL UNFURNISHED VILLA AVAILABLE FOR LEASE IN BLACKBURN HARBOR IN OSPREY! This beautiful 2BR 2BA villa has a large lanai with peaceful views over Blackburn Harbor and features Brazilian Cherry hardwood floors, stainless steel appliances and a private one car garage. The entire condo has been freshly painted. Blackburn Harbor is a gated community and offers many amenities, which include a

  Alex Lane PREMIER SOTHEBY'S INTERNATIONAL REALTY

  2313 Jessie Harbor Dr Unit 2302, Osprey, FL 34229
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  /2

  $479,000 Sold Sep 10, 2025

  • 1,904 Sq Ft
  • $252/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1971

  26 Bay Acres Ave, Osprey, FL 34229

  Discover this hidden gem in the sought-after waterfront community in Bay Acres, positioned West of the Trail with direct access to the Intracoastal Waterway situated on .037 acres that is completely fenced in for privacy! This beautifully renovated home has 3 spacious bedrooms and 2 bathrooms across 1,904 sqft, offering a split bedroom floor plan for maximum privacy. The primary suite features

  Erica Giesler RE/MAX ALLIANCE GROUP

  26 Bay Acres Ave, Osprey, FL 34229
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  /98

  Est $801,404 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
• 

  

  /98

  $1,175,000

  • 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
• 

  

  /18

  $1,850 per month

  • 2 Beds
  • 1 Bath
  • 950 Sq Ft
  • House for Rent

  455 Pennsylvania Ave, Osprey, FL 34229

  Fully Furnished 2BR/1BA Turnkey Home in Osprey, FLUnique, peaceful property with native wildflower garden, beach gear, and old-Florida charm. Located in the quiet fishing village of Osprey, this FULLY FURNISHED home includes:•Upgraded kitchen with stainless steel appliances, granite counters, and all essentials•New washer/dryer•Enclosed lanai•High-speed WiFi, water, sewer,

  455 Pennsylvania Ave, Osprey, FL 34229
• 

  /2

  $452,500 Sold Aug 29, 2025

  • 1,574 Sq Ft
  • $287/SF
  • 257 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1981

  784 Sarabay Rd, Osprey, FL 34229

  Welcome to Your Waterfront Villa in Osprey, Florida!Discover the ultimate seasonal retreat in this beautifully updated 2-bedroom, 2-bathroom single-story villa, designed for stress-free living. Nestled in a private 25-unit secluded community, this waterfront gem offers not only stunning views but also a lifestyle of unparalleled ease and simplicity.Key Features:Move in ready: Move in

  Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, Osprey, FL 34229
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  /50

  Est $1,113,342 Not Listed For Sale

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

  3973 Waypoint Ave, Osprey, FL 34229

  3973 Waypoint Ave, 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
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  /36

  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 1,069 Sq Ft
  • House for Rent

  305 Bay Vista Ave, Osprey, FL 34229

  Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

  Jennifer . STOCKTON REALTY ADVISORS LLC

  305 Bay Vista Ave, Osprey, FL 34229
• 

  /2

  $3,900,000 Sold Aug 27, 2025

  • 1,876 Sq Ft
  • $2,079/SF
  • 657 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1992

  426 N Casey Key Rd, Osprey, FL 34229

  Gulf to Bay on North Casey Key – the perfect location! Panoramic views of Little Sarasota Bay to the east and a beachfront lot on the west. Original cypress tongue and groove ceilings and beautiful oak floors add warmth and nostalgia throughout the home. A nicely updated kitchen overlooks the pool and bay. The entire second floor is dedicated to an oversized primary suite with a sitting room and

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  426 N Casey Key Rd, Osprey, FL 34229
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  /53

  Est $604,899 Not Listed For Sale

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

  4421 Conchfish Ln, Osprey, FL 34229

  4421 Conchfish Ln, Osprey, FL 34229
• 

  

  /76

  $2,195,000

  • 3 Beds
  • 3 Baths
  • 3,681 Sq Ft

  600 Eagle Watch Ln, Osprey, FL 34229

  Located on one of the most desirable streets in The Oaks Clubside, this completely renovated pool home sits on a generous 0.71-acre lot with wide views of the third hole of the Heron Golf Course. Nearly every aspect of the property has been updated—new roof, impact-rated windows and doors, flooring, trim, countertops, appliances, resurfaced pool and spa, new pool cage, and a resurfaced

  

  Joe Murphy

  COLDWELL BANKER REALTY

  (941) 274-4697

  600 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /49

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

  Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
• 

  /2

  $660,000 Sold Aug 26, 2025

  • 2,153 Sq Ft
  • $307/SF
  • 63 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2002

  463 Park Trace Blvd, Osprey, FL 34229

  On an oversized lot with a breathtaking lake view, this open floor plan turnkey-furnished residence is designed for modern living. Recent upgrades include a new roof with a 15-year transferable warranty and a new water heater, ensuring peace of mind. Enter inside to high ceilings accented with crown molding, enhancing the home's spacious and refined atmosphere. At the heart of the home is a

  Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  463 Park Trace Blvd, Osprey, FL 34229
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  /78

  Est $502,483 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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  /60

  $560,000

  • 4 Beds
  • 2 Baths
  • 1,981 Sq Ft

  813 Oak Pond Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. WELCOME HOME!! THERE HAS BEEN NO FLOODING OR DAMAGE FROM RECENT STORMS!! RECENTLY APPRAISED at $560,000!! This is a Beautiful and Spacious 4 bed/2 bath Home in the Community of Bay Oaks Estates. It is just a Short Drive to 3 different Gorgeous Beaches including Nokomis Beach, Venice Beach and the World Famous Siesta Key! Easy Access to Tamiami Trail

  

  Jeremy Egglefield

  PREFERRED SHORE LLC

  (941) 394-8541

  813 Oak Pond Dr, Osprey, FL 34229
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  /44

  $3,950 per month

  • 3 Beds
  • 3 Baths
  • 1,781 Sq Ft
  • House for Rent

  451 N Shore Dr, Osprey, FL 34229

  Welcome to your new spacious home in the beautiful waterfront neighborhood of Sorrento Shores. As you approach this three bedroom, three bath POOL house you will notice the quiet charm that this highly sought-after neighborhood provides. The streets are lined with tropical fruit trees, palms, and plants that create a tranquil atmosphere. The open concept, split floor plan, and wonderfully updated

  Justin Ulrich ZACHOS REALTY & DESIGN GROUP

  451 N Shore Dr, Osprey, FL 34229
• 

  /2

  $470,000 Sold Aug 22, 2025

  • 2,166 Sq Ft
  • $217/SF
  • 80 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229

  Enjoy the best of coastal living in this spacious 2,166 sq. ft fully furnished townhouse condo, perfectly situated within walking distance of Casey Key and just steps from Casey Key Marina and Blackburn Point Park. This 15-acre waterfront park offers kayaking, fishing, a public boat ramp, and more. The thoughtfully designed first-floor master suite features a walk-in shower, a garden tub, and

  Margaret Kennedy MICHAEL SAUNDERS & COMPANY

  1110 Beachcomber Ct Unit 1, Osprey, FL 34229
• 

  

  /39

  Est $319,597 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,244 Sq Ft

  4325 Expedition Way Unit 103, Osprey, FL 34229

  4325 Expedition Way Unit 103, Osprey, FL 34229
• 

  

  /78

  $1,095,000

  • 5 Beds
  • 4 Baths
  • 3,938 Sq Ft

  820 Placid Lake Dr, Osprey, FL 34229

  Discover this expansive 5-bedroom, 4-bathroom home with an oversized bonus room and 3,938 sq. ft. of living space, perfectly situated on a 10,548 sq. ft. lakefront lot. Recent upgrades provide peace of mind and modern comfort, including a new tile roof (2024), new zoned HVAC units (2022), a new pool heater (2024), a new water heater (2025) with a 25-year whole-home water conditioner, fresh

  Ali Marks LOYD ROBBINS & CO. LLC

  820 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $2,749 per month

  • 3 Beds
  • 2 Baths
  • 1,462 Sq Ft
  • House for Rent

  413 Glenwood Ave, Osprey, FL 34229

  Coming soon - this home is currently being enjoyed by another resident but will be available soon. Pre-lease this home now with Tricon Pre-Lease Guarantee. This home is professionally managed by Tricon Residential, dedicated to creating exceptional rental experiences. Featuring 3 bedrooms, 2.0 bathrooms, and approximately 1,462 square feet, this well-maintained home offers a high standard of

  413 Glenwood Ave, Osprey, FL 34229
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  /2

  $3,050,000 Sold Aug 15, 2025

  • 2,380 Sq Ft
  • $1,282/SF
  • 278 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 1969

  5 N Casey Key Rd, Osprey, FL 34229

  HOME RUN DEAL YOU CAN'T AFFORD TO MISS! CASEY KEY GULF FRONT MOVE-IN READY FOR UNBELIEVABLE PRICE! REDUCED 900K! Iconic Gulf-front Mid-Century Modern gated residence on Casey Key embodies the true essence of casual coastal living, offering an unparalleled retreat for the soul. The moment you step through the door, a magical transformation takes place. Your senses awaken as you are immediately

  Kelley Ann Ayers AYERS AND ASSOCIATES REAL ESTATE

  5 N Casey Key Rd, Osprey, FL 34229
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  /15

  Est $780,548 Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, Osprey, FL 34229
• 

  

  /61

  $1,395,000

  • 3 Beds
  • 3 Baths
  • 2,545 Sq Ft

  3603 N Point Rd Unit 702, Osprey, FL 34229

  **MAGNIFICENT VIEW from this 7th FLOOR, PENTHOUSE CONDO** Offering 3 EN SUITE BEDROOMS, 3 FULL BATHS and a treasured PRIVATE 2-CAR GARAGE! Located behind the gates of the highly sought after Oaks-Preserve, country club neighborhood in the Newest Meridian Condo Tower (Built in 2007 and featuring Hurricane Impact rated Windows and Sliding Doors). As you emerge from your private elevator foyer

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 702, Osprey, FL 34229
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  /9

  $2,395 per month

  • 2 Beds
  • 2 Baths
  • 1,145 Sq Ft
  • Townhouse for Rent

  1817 Highland Rd, Osprey, FL 34229

  Lovely 2 bed/2 bth well maintained townhouse with a 2 car garage Set in a private enclave in the desirable West of Trail Osprey location with a Community pool. Close to beaches, restaurants and shopping.

  Steven Koleno BEYCOME OF FLORIDA LLC

  1817 Highland Rd, Osprey, FL 34229
• 

  /2

  $247,000 Sold Aug 14, 2025

  • 1,325 Sq Ft
  • $186/SF
  • 3 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  121 Woodland Place Unit 121, Osprey, FL 34229

  Fabulous location for this FULLY FURNISHED, TURNKEY, two bedroom second floor condo in the Pine Run neighborhood. If you've been thinking of becoming a snowbird, you couldn't ask for more than this! Close to the iconic Casey Key Fish House Tiki Bar, the inter coastal, shopping, restaurants, main roads, and several beaches!! Located between Venice and Sarasota, you can easily enjoy both

  Pat Williams PAT WILLIAMS REALTY, LLC

  121 Woodland Place Unit 121, Osprey, FL 34229
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  /41

  Est $1,224,163 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,416 Sq Ft

  3932 Waypoint Ave, Osprey, FL 34229

  3932 Waypoint Ave, Osprey, FL 34229

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