Osprey, FL Homes

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  /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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  /53

  $5,000 per month

  • 2 Beds
  • 2.5 Baths
  • 1,950 Sq Ft
  • Condo for Rent

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229

  Annual Turnkey Furnished or short term seasonal Penthouse on the Bay! If you want mesmerizing views of intracoastal waterway, Little Sarasota Bay, Casey Key, and the Gulf of Mexico in a beautiful, comfortable and roomy penthouse, then this could be your next home. This natural light filled delight is 2 bedrooms, each with en suite bathroom, separate office with large closet and glass French

  Henry Rossi RENT SARASOTA

  260 Hidden Bay Dr Unit B-504, Osprey, FL 34229
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  /2

  $2,925,000 Sold Sep 23, 2025

  • 7,842 Sq Ft
  • $373/SF
  • 63 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 2006

  550 Dove Pointe, Osprey, FL 34229

  Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside,

  Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
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  /5

  Not Listed For Sale

  0 N Point Rd Unit A11454780, Osprey, FL 34229

  0 N Point Rd Unit A11454780, Osprey, FL 34229
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  /62

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 4,241 Sq Ft

  909 MacEwen Dr, Osprey, FL 34229

  **STUNNING GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an Over Half Acre Lot overlooking the 12th Fairway of the interior, HERON GOLF COURSE. With its delightful curb appeal and manicured landscape, this splendid residence offers 3 BEDROOMS + Spacious Executive Office/Study, 3 FULL and 1 HALF BATHS, High Ceilings, Crown Moldings, Gas Fireplace,

  Mark Lyda GENEROUS PROPERTY

  909 MacEwen Dr, Osprey, FL 34229
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  /44

  $6,500 per month

  • 3 Beds
  • 3 Baths
  • 2,266 Sq Ft
  • House for Rent

  521 Habitat Blvd, Osprey, FL 34229

  REDUCED FOR THE SEASON! Stylish 3BR Pool Home w/ Office – 10 Mins to Beach ****SEASONAL RENTAL ONLY**** 60 Day minimum stay in Peak Season at $8,900/mo plus fees; Minimum 60 Day stay in Off Season at $6,500/mo plus fees. Your Gulf Coast getaway awaits at this beautifully furnished 3-bedroom, 3-bath pool home in the scenic Willowbend community of Osprey, FL. Ideal for mid-term stays, this spacious

  Dave Holt PMI SARASOTA

  521 Habitat Blvd, 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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  /2

  Est $302,701 Not Listed For Sale

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

  4219 Frontier Ln Unit 105, Osprey, FL 34229

  4219 Frontier Ln Unit 105, Osprey, FL 34229
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  /43

  $780,250 New Construction

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

  280 Hidden Bay Dr Unit 202, Osprey, FL 34229

  READY FOR IMMEDIATE OCCUPANCY!Modern Elegance at Edgewater: A Luxurious Haven Overlooking Little Sarasota BayStep into a world of contemporary sophistication with this new construction condominium nestled in the eminent enclave of Edgewater at Hidden Bay. Boasting 1937 square feet, this meticulously crafted residence offers three bedrooms, two bathrooms, and an inviting office space

  Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  280 Hidden Bay Dr Unit 202, Osprey, FL 34229
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  /39

  $4,200 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  280 Hidden Bay Dr Unit 302, Osprey, FL 34229

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  280 Hidden Bay Dr Unit 302, 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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  /24

  Est $298,944 Not Listed For Sale

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

  4224 Expedition Way Unit 105, Osprey, FL 34229

  4224 Expedition Way Unit 105, Osprey, FL 34229
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  /57

  $1,570,000 New Construction

  • 3 Beds
  • 3.5 Baths
  • 2,913 Sq Ft

  360 N Point Rd, Osprey, FL 34229

  **DON’T WAIT TO BUILD!** EXQUISITE, NEWLY-CONSTRUCTED and NEVER LIVED-IN, SPANISH MISSION STYLE home behind the Secure Gates of the COVETED, OAKS PRESERVE Country Club Neighborhood on Sarasota Bay waters offers superb attention to detail. This Custom-Built residence boasts 3 EN SUITE BEDROOMS + 3 FULL and 1 HALF BATHS and a desirable Open Floorplan concept. A well-equipped Chef’s Kitchen

  Mark Lyda GENEROUS PROPERTY

  360 N Point Rd, Osprey, FL 34229
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  /39

  $4,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,166 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR RENT – READY FOR IMMEDIATE OCCUPANCYModern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier LG appliances, solid wood

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
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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 DOUGLAS ELLIMAN

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
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  /4

  Est $54,028 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229

  570 Blackburn Point Rd Unit 1-SIES, Osprey, FL 34229
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  /68

  $949,900 Pending

  • 4 Beds
  • 3 Baths
  • 3,438 Sq Ft

  766 Shadow Bay Way, Osprey, FL 34229

  Under contract-accepting backup offers. LISTING AGENT WILL CONTINUE TO ACCOMPANY SHOWINGS. Nestled on a quiet street in the highly sought-after Rivendell community, this former Arthur Rutenberg model home features 4 bedrooms, 3 full baths, a den, and 2 versatile flex rooms, offering tranquil views of the pond and surrounding preserve. Framed by lush landscaping, the property features an oversized

  Anne Pfitzenreiter COLDWELL BANKER SARASOTA CENT.

  766 Shadow Bay Way, Osprey, FL 34229
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  /9

  $2,000 per month

  • 3 Beds
  • 1.5 Baths
  • 1,173 Sq Ft
  • House for Rent

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This amazingly located residence offers 3 bedrooms, 1 and a half bathrooms, and 1,173 square feet of comfortable living space. The open-concept layout features vaulted ceilings and a NEW modern kitchen equipped with granite countertops, soft close drawers, a center island, and new Frigidaire

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, 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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  /12

  Est $24,450 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229

  570 Blackburn Point Rd Unit 9-LIDO, Osprey, FL 34229
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  /57

  $649,995 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,298 Sq Ft

  594 Pine Ranch Rd E, Osprey, FL 34229

  Under contract-accepting backup offers. Discover this beautifully maintained 3-bedroom, 2-bathroom home nestled in a peaceful, private community just steps from the scenic Legacy Trail. Surrounded by mature trees and vibrant birdlife, this property offers the perfect blend of tranquility and convenience.Step inside to a spacious split floor plan featuring luxury vinyl plank flooring, crown

  Dan Henson DALTON WADE INC

  594 Pine Ranch Rd E, Osprey, FL 34229
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  /39

  $7,000 per month

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft
  • Condo for Rent

  Unlisted Address

  NOW AVAILABLE FOR SEASONAL RENTAL – READY FOR IMMEDIATE OCCUPANCY AND FULLY FURNISHED!Modern Elegance at Edgewater | Stunning Condo with Bay ViewsLive the luxury lifestyle in this brand-new 3-bedroom, 2-bathroom + office condominium in the exclusive Edgewater at Hidden Bay community. Offering 1,937 sq ft of modern design, this elegant residence features a gourmet kitchen with top-tier

  Jim Xarras, Jr BERKSHIRE HATHAWAY HOMESERVICE

  Unlisted Address
• 

  /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 $552,309 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  2006 Preymore St, Osprey, FL 34229

  2006 Preymore St, Osprey, FL 34229
• 

  

  /25

  $189,000

  • 2 Beds
  • 2 Baths
  • 1,120 Sq Ft

  218 Palm Air Dr, Osprey, FL 34229

  You’ll be impressed with this delightful double wide from the moment you enter featuring 2 spacious bedrooms and 2 updated bathrooms with a total of 1120 Sq Feet built in 1979 with large shed and enclosed lanai. Being sold Furnished and Turnkey. The kitchen was totally remodeled in 2020 an island was added with new appliances in and it flows into the dining area and living room creating a large

  Carlos Saramago EXIT KING REALTY

  218 Palm Air Dr, Osprey, FL 34229
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  /87

  $7,000 per month

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

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229

  Available from December 7, 2025, and Jan/Feb/Mar/Apr 2026. Beautiful 5th Floor condo located in Blackburn Harbor Residences with breathtaking panoramic water views of Little Sarasota Bay, which can be seen from the living room, kitchen, primary bedroom suite, and spacious balcony! The condo comes turnkey furnished and has 3 bedrooms (3rd bedroom was converted from a den) and 2 bathrooms. As you

  Chrissie Cummings JENNETTE PROPERTIES INC

  5100 Jessie Harbor Dr Unit 504, Osprey, FL 34229
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  /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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  /17

  Est $299,771 Not Listed For Sale

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

  4247 Expedition Way Unit 103, Osprey, FL 34229

  4247 Expedition Way Unit 103, Osprey, FL 34229
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  /67

  $1,690,000

  • 3 Beds
  • 4.5 Baths
  • 3,905 Sq Ft

  325 Osprey Point Dr, Osprey, FL 34229

  **BEAUTIFULLY UPDATED COUNTRY CLUB ESTATE with Ideal Southern Exposure and WATER VIEW** is located in the COVETED, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Enjoy the Private and Tranquil, Lake-front setting of this Meticulously Maintained, Timeless residence with Stunning Architectural Detail as designed by Famed Architect, Bo MacEwen, who also designed the breathtaking Oaks

  Mark Lyda GENEROUS PROPERTY

  325 Osprey Point Dr, Osprey, FL 34229
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  /43

  $5,000 per month

  • 3 Beds
  • 2 Baths
  • 2,374 Sq Ft
  • Condo for Rent

  14041 Bellagio Way Unit 218, Osprey, FL 34229

  Welcome to your coastal sanctuary in the gated community of Villas at Osprey Harbor Village. Located just minutes from Midnight Pass beach, Snake Island and walking distance to Casey Key fish house. This impeccably remodeled 3 bedroom, 2 bathroom residence offers an elegant, light-filled living space with breath taking harbor and sunset views from every room. Designed with both comfort and style

  Kelli Eggen COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 218, Osprey, FL 34229
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  /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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  /39

  Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,664 Sq Ft

  169 Edgewood Dr, Osprey, FL 34229

  169 Edgewood Dr, Osprey, FL 34229
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  /71

  $2,300,000

  • 4 Beds
  • 4 Baths
  • 3,235 Sq Ft

  889 MacEwen Dr, Osprey, FL 34229

  **INCREDIBLE TRANSFORMATION OF THIS MOVE-IN READY, GOLF COURSE ESTATE** From the Reimagined Entryway and through the Stunning Iron double front door, you will be captivated by the attention to detail throughout this elegantly appointed residence located on an Over Half Acre, Private lot on the Interior, Heron Golf Course in the highly-sought after, OAKS COUNTRY CLUB community. The recently

  Mark Lyda GENEROUS PROPERTY

  889 MacEwen Dr, Osprey, FL 34229
• 

  

  /25

  $1,995 per month

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft
  • Townhouse for Rent

  184 Explorer Dr, Osprey, FL 34229

  The unit is available for rent from October 1 till December 30 , 2025.The minimum rental period is 1 month. The monthly rent is $1995. The tenant is responsible for electricity and internet costs. INCLUDED IN THE LEASE : Water, sewer. If you are looking for the perfect Florida lifestyle, this is it. Conveniently located between Sarasota and Venice with #1 Siesta Key beach close by, this

  Claudia Dybala DALTON WADE INC

  184 Explorer Dr, Osprey, FL 34229
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  /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
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  /27

  Est $353,004 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  4260 Expedition Way Unit 4260, Osprey, FL 34229

  4260 Expedition Way Unit 4260, Osprey, FL 34229
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  /39

  $879,000

  • 3 Beds
  • 3 Baths
  • 2,622 Sq Ft

  903 Tranquility Cir, Osprey, FL 34229

  **IMPRESSIVE POOL/SPA HOME on a Desirable Corner Lot with Partial Water View** Custom-built by John Cannon and situated on an interior Cul De Sac in popular North Creek Estates, this 3-BED + Office/Den, 3 FULL BATH, 2-Car Garage residence affords wonderful privacy and features 2622sf of heated living area plus a spacious screened lanai with Heated Pool/Spa and ample covered seating area, for the

  Mark Lyda GENEROUS PROPERTY

  903 Tranquility Cir, Osprey, FL 34229
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  /33

  $3,695 per month

  • 2 Beds
  • 3.5 Baths
  • 1,890 Sq Ft
  • Townhouse for Rent

  60 Bishops Court Rd Unit 114, Osprey, FL 34229

  This is a rare opportunity to rent a luxury, unfurnished townhome located in the heart of the Oaks Preserve. Showcasing charming architectural details and quality finishes, this traditional-style home offers an inviting floor plan with two bedrooms, each featuring its own en-suite bath. The gracious living and dining areas flow seamlessly into a spacious and private outdoor living space that

  Heidi Thompson STRINGER MANAGEMENT INC

  60 Bishops Court Rd Unit 114, Osprey, FL 34229
• 

  /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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  /24

  Est $592,695 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  2001 Cordes St, Osprey, FL 34229

  2001 Cordes St, Osprey, FL 34229

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