Osprey, FL Homes

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  /62

  $409,900

  • 2 Beds
  • 2 Baths
  • 1,400 Sq Ft

  2251 Jessie Harbor Dr, Osprey, FL 34229

  **1ST FLOOR END UNIT CONDO with WATER VIEW and PRIVATE 1-CAR GARAGE, WEST OF TRAIL! BRING YOUR BOAT & KAYAK for DIRECT ACCESS TO INTRACOASTAL WATERWAY and GULF OF MEXICO (No Bridges)** Featuring 2 BEDS and 2 FULL BATHS, this LIGHT AND BRIGHT, 1ST FLOOR END UNIT dwelling features an Impressive Kitchen with Granite counters, Stainless Steel appliances and solid wood cabinets while the Spacious

  Mark Lyda GENEROUS PROPERTY

  2251 Jessie Harbor Dr, Osprey, FL 34229
• 

  

  /2

  $520,000 Sold Feb 14, 2025

  • 1,680 Sq Ft
  • $310/SF
  • 14 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1997

  555 Meadow Sweet Cir, Osprey, FL 34229

  Rivendell is a unique neighborhood. You must see it to appreciate the quaint and friendly setting. This home is in the original "Cottages of Rivendell". From the canopy tree's lining the neighborhood to the uniqueness of the individual homes you will be impressed. ; This home has an efficient layout that lets you easily decorate and enjoy every space. Also no need to worry about the many

  Jack Keller JACK KELLER INC

  555 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  

  /100

  Est $2,843,997 Not Listed For Sale

  • 4 Beds
  • 6 Baths
  • 5,493 Sq Ft

  458 E MacEwen Dr, Osprey, FL 34229

  458 E MacEwen Dr, Osprey, FL 34229
• 

  

  

  /55

  $845,000

  • 4 Beds
  • 4 Baths
  • 3,183 Sq Ft

  650 Crane Prairie Way, Osprey, FL 34229

  BEST PRICED HOME PER SQ FT in a 3-Mile Radius! Now Offered at $845,000 | Lease Option/Purchase Available!Live large in this 3,183 sq ft Lee Wetherington masterpiece with private pool and preserve OSCAR SCHERE PARK views in the coveted Willowbend community—just minutes from Casey Key Beach and the nationally ranked Pine View School for the Gifted. Offering over 3,180 sq ft, this home features

  Cheri Castro KELLER WILLIAMS ON THE WATER

  650 Crane Prairie Way, Osprey, FL 34229
• 

  

  /2

  $3,335,000 Sold Feb 12, 2025

  • 2,417 Sq Ft
  • $1,380/SF
  • 7 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1978

  419 Yacht Harbor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Considered one of the finest community-owned marinas on the west coast of Florida, Southbay Yacht & Racquet Club features a seven-acre, deep-water boat basin that will accommodate kayaks, jet skis, sailboats, powerboats, catamarans and yachts up to 55 feet in length. With a 6-foot depth at mean low tide, the marina can accommodate 175 boats owned by

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  419 Yacht Harbor Dr, Osprey, FL 34229
• 

  

  /11

  Est $331,594 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,402 Sq Ft

  217 Glenwood Ave, Osprey, FL 34229

  217 Glenwood Ave, Osprey, FL 34229
• 

  

  /46

  $675,000

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

  14041 Bellagio Way Unit 214, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Massive Price Reduction! Original Listing Price was $810,000. Reduced by $135,000 to $675,000. Seller is motivated! Step into this luxurious, meticulously maintained 3-bedroom, 2-bath condo featuring high ceilings, granite countertops, updated appliances, and a separate laundry room. Enjoy magnificent views of Little Sarasota Bay and a lively

  Veronica Lee FINE PROPERTIES

  14041 Bellagio Way Unit 214, Osprey, FL 34229
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  /2

  $317,500 Sold Feb 07, 2025

  • 1,244 Sq Ft
  • $255/SF
  • 5 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  128 Navigation Cir Unit 103, Osprey, FL 34229

  This charming Florida condo is perfect for anyone seeking a full-time residence or a seasonal getaway. The unit is being sold furnished. Lovely, 2 bedrooms, 2 baths, attached single car garage. The Heron floor plan features an open concept kitchen with dining and great room. Easy access to the resort-style heated pool, fitness room, and club room. The property is comprised of two bedrooms

  Tim Weller EXIT KING REALTY

  128 Navigation Cir Unit 103, Osprey, FL 34229
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  /33

  Est $2,932,346 Not Listed For Sale

  • 4 Beds
  • 7 Baths
  • 8,763 Sq Ft

  692 Oaks Creek Ct, Osprey, FL 34229

  692 Oaks Creek Ct, Osprey, FL 34229
• 

  

  /80

  $485,000

  • 2 Beds
  • 3 Baths
  • 2,837 Sq Ft

  264 Woods Point Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Fresh paint is done, and new carpet is coming. SELLER WILL CONSIDER LEASE PURCHASE. Try it before you buy it. Price reflects the need to update property interior. With expected ARV (after repair value) of +/- $600k, $91 per square foot under the most recent sale in the neighborhood, and less than a mile from the beach this is a great opportunity to

  Mark Midyett KELLER WILLIAMS ON THE WATER S

  264 Woods Point Rd, Osprey, FL 34229
• 

  /2

  $1,850,000 Sold Jan 31, 2025

  • 4,361 Sq Ft
  • $424/SF
  • 31 Days On Market

  • 5 Beds
  • 4 Baths
  • Built 2006

  855 MacEwen Dr, Osprey, FL 34229

  This stunning 5 bedroom, 4 bath residence, custom built by Wetherington, epitomizes refined living and sophisticated elegance. Nestled in The Oaks Clubside, it enjoys an incredible private setting, with no house or neighbors on one side. This home is large and spacious, with timeless design elements, creating an exquisite sanctuary. As you enter through the double leaded glass front doors, the

  Steve Abbe COLDWELL BANKER REALTY

  855 MacEwen Dr, Osprey, FL 34229
• 

  /2

  Est $581,007 Not Listed For Sale

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

  825 Oak Pond Dr, Osprey, FL 34229

  825 Oak Pond Dr, Osprey, FL 34229
• 

  

  /7

  $239,999

  • Land
  • 0.13 Acre
  • $1,846,146 per Acre

  456 Washington Ave, Osprey, FL 34229

  Owner Financing is Available. Prime Land at 456 Washington Ave, Osprey, FL 34229 – A Rare Gem Near Historic Spanish Point & Selby Gardens. Don’t miss out on this incredible opportunity to own a prime piece of land at 456 Washington Ave, located in the heart of Osprey, FL. Surrounded by natural beauty and rich history, this property is just moments from the renowned Historic Spanish Point and

  Mike Vo FLOTACAL

  456 Washington Ave, Osprey, FL 34229
• 

  /2

  $1,650,000 Sold Jan 31, 2025

  • 5,399 Sq Ft
  • $306/SF
  • 12 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 1992

  676 Eagle Watch Ln, Osprey, FL 34229

  Florida living at its finest! You'll find this lovely home tucked away on a cul-de-sac in the luxurious community known as The Oaks. This amazing custom-built home features 5 bedrooms, 5.5 bathrooms and 5,399 sq. ft. of fabulous living space, combining comfort with elegance! Upon entering you are greeted by the formal living room with high ceilings, crown molding, large sliding glass doors and

  Jamie Mullis COLDWELL BANKER REALTY

  676 Eagle Watch Ln, Osprey, FL 34229
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  /48

  Est $616,777 Not Listed For Sale

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

  522 Meadow Sweet Cir, Osprey, FL 34229

  522 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /48

  $685,000

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

  409 N Point Rd Unit 502, Osprey, FL 34229

  **GORGEOUS VIEW from this Move-In Ready, 5TH FLOOR, 3-BED / 3-BATH, LUXURY CONDO!! The coveted lifestyle of The Oaks Country Club with the convenience and amenities of maintenance-free condominium living come together at this Gorgeous Meridian 5th floor residence. Upon exiting the elevator into the private foyer, step inside and enjoy the breathtaking panoramic preserve, bay and Gulf of Mexico

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 502, Osprey, FL 34229
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  /2

  $1,450,000 Sold Jan 31, 2025

  • 4,614 Sq Ft
  • $314/SF
  • 193 Days On Market

  • 5 Beds
  • 5.5 Baths
  • Built 2003

  738 N MacEwen Dr, Osprey, FL 34229

  Imagine how you’d like to live the ultimate Florida lifestyle. Your vision can become a reality in this 5 bedroom, 5.5 bath two story home in The Oaks Clubside. Currently unfurnished, you just need to pack your bags, bring your own style and make it your own. Set back on a cul-de-sac lot, with gorgeous lake and golf views, the floor plan offers flexibility for the space to be used by residents

  Steve Abbe COLDWELL BANKER REALTY

  738 N MacEwen Dr, Osprey, FL 34229
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  /38

  Est $590,678 Not Listed For Sale

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

  574 Oak Bay Dr, Osprey, FL 34229

  574 Oak Bay Dr, Osprey, FL 34229
• 

  

  /61

  $251,500

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft

  758 Pine Run Dr Unit 758, Osprey, FL 34229

  This home was professionally inspected by a Contractor following Hurricanes Helene and Milton, and I’m pleased to report it sustained no damage from the storms. Welcome to this beautifully updated, spacious 2-story condo, boasting 2 bedrooms, 2.5 bathrooms, and updated modern finishes throughout. Nestled in a desirable community, you'll be just minutes from the beach, with easy access to

  Greg Vander Wel REALNET FLORIDA REAL ESTATE

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

  /2

  $900,000 Sold Jan 31, 2025

  • 2,855 Sq Ft
  • $315/SF
  • 281 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1997

  201 Saint James Park, Osprey, FL 34229

  Welcome home to your sanctuary located behind the gates of the Exclusive Oaks Country Club. This corner lot in SAINT JAMES PARK is situated close to the CLUB, TENNIS, and all the amenities the community has to offer. As you approach the home the lush landscape and stunning trees capture your attention. Enter through the double front door to a serene view of the mature landscaping and view of the

  Tina Timmons ROSEBAY INTERNATIONAL REALTY, INC

  201 Saint James Park, Osprey, FL 34229
• 

  

  /48

  Est $816,486 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,093 Sq Ft

  763 Shadow Bay Way, Osprey, FL 34229

  763 Shadow Bay Way, Osprey, FL 34229
• 

  

  /38

  $185,000 Open House 10/05

  • 2 Beds
  • 2 Baths
  • 1,376 Sq Ft

  191 Palm Air Dr, Osprey, FL 34229

  Come home to this tastefully-furnished, well-maintained spacious home in a top-of-the-line, perfectly located Co-Op park. LOTS OF UPGRADES: NEW windows 2022, NEW A/C and HVAC 2023, NEW moisture barrier underneath 2022. NEW hurricaine window covers 2023, NEW Solar tube in kitchen 2022, NEW ceiling fan in dining area 2022. Relax in the 1,376 square feet of centrally-cooled comfort. Two

  John Alexander FINE PROPERTIES

  191 Palm Air Dr, Osprey, FL 34229
• 

  /2

  $435,000 Sold Jan 30, 2025

  • 2,055 Sq Ft
  • $212/SF
  • 106 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2001

  393 N Point Rd Unit 302, Osprey, FL 34229

  Enter through the secure foyer and take one of the two private elevators to the third floor where you will find this charming 3 bedroom (one is currently being used as a den/office and has the convenience of a built-in Murphy bed!), 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and spacious. Carefully updated and

  Steve Abbe COLDWELL BANKER REALTY

  393 N Point Rd Unit 302, Osprey, FL 34229
• 

  

  /39

  Est $740,969 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,492 Sq Ft

  1096 Mallard Marsh Dr, Osprey, FL 34229

  1096 Mallard Marsh Dr, Osprey, FL 34229
• 

  

  /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. Welcome to luxury condo living in The Oaks Preserve. This 3 bedroom, 3 bath corner unit with office, offers everything you need to live the country club lifestyle with comfort and ease. Take your private elevator to the 5th floor and you will find this lovely residence in pristine condition. The kitchen has stainless steel appliances, breakfast

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 501, Osprey, FL 34229
• 

  /2

  $1,200,000 Sold Jan 27, 2025

  • 3,906 Sq Ft
  • $307/SF
  • 212 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1989

  639 Eagle Watch Ln, Osprey, FL 34229

  You won’t find a home like this elegant 4 bedroom, 5.5 bath beauty every day. Situated on a beautiful lot in The Oaks Clubside, it offers privacy and stunning views overlooking the lake out to the #7 of the Heron Course. The quiet street ends in a cul-de-sac. Inside you will find a spacious floor plan that is anything but cookie-cutter. This home has a 4th bedroom above the garage, perfect as a

  Steve Abbe COLDWELL BANKER REALTY

  639 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /39

  Est $684,383 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,303 Sq Ft

  680 Shadow Bay Way, Osprey, FL 34229

  680 Shadow Bay Way, Osprey, FL 34229
• 

  

  /91

  $399,900

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

  401 N Point Rd Unit 301, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Enter through the secure foyer and take the private elevator to the third floor where you will find this charming 3 bedroom, 3 bath residence. Situated at treetop level, overlooking the preserve and surrounding lush foliage, the interior is open and neutral, with lots of natural light. This unit is waiting for you to come and put your decorating

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 301, Osprey, FL 34229
• 

  /2

  $2,100,000 Sold Jan 24, 2025

  • 3,896 Sq Ft
  • $539/SF
  • 140 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1989

  627 Eagle Watch Ln, Osprey, FL 34229

  **EXQUISITELY DESIGNED and BRILLIANTLY RENOVATED, CUSTOM GOLF COURSE ESTATE with SPECTACULAR WATER VIEW** is situated on the Interior HERON GOLF COURSE and is located on a tranquil, cul-de-sac street behind the Secure Gates of The Oaks Country Club neighborhood. Framed by stunning Grand Oaks, your approach will only be enhanced upon entering through the grand double doors and gazing out across

  Mark Lyda GENEROUS PROPERTY

  627 Eagle Watch Ln, Osprey, FL 34229
• 

  

  /40

  Est $547,917 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  590 Oak Bay Dr, Osprey, FL 34229

  590 Oak Bay Dr, Osprey, FL 34229
• 

  

  /93

  $679,000

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

  409 N Point Rd Unit 603, Osprey, FL 34229

  BEAUTIFUL FULL WATER VIEWS OF NORTH CREEK, SARASOTA BAY, AND THE GULF! Watch the eagles and osprey fish and enjoy truly stunning sunsets from the balcony of this condo with 3 bedrooms, 3 full baths and a formal dining room/den. With this condo you have found a best-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to offer. Take the private elevator to the sixth floor

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 603, Osprey, FL 34229
• 

  /2

  $325,000 Sold Jan 17, 2025

  • 623 Sq Ft
  • $522/SF
  • 0 Days On Market

  • 1 Bed
  • 1 Bath
  • Built 1990

  51 MacEwen Dr Unit 20, Osprey, FL 34229

  **BEAUTIFUL VIEW FROM THIS 2ND STORY, RENOVATED EFFICIENCY CONDO UNIT WITH BALCONY OVERLOOKING THE OAKS CLUBHOUSE ACROSS EXPANSIVE POND WITH FOUNTAIN** THE OAKS is a distinguished, 24hr Guarded, Country Club Community which boasts many accolades including: Platinum Club of America, Emerald Club of the World, Elite Distinguished Club of the World and One of America’s Healthiest Clubs - where

  Mark Lyda GENEROUS PROPERTY

  51 MacEwen Dr Unit 20, Osprey, FL 34229
• 

  

  /49

  Est $172,770 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 586 Sq Ft

  701 Pine Run Dr, Osprey, FL 34229

  701 Pine Run Dr, Osprey, FL 34229
• 

  

  /94

  $1,549,000

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

  401 N Point Rd Unit 901, Osprey, FL 34229

  This opulent 3 bedroom plus den, 3 bath residence with a PRIVATE 2 CAR GARAGE located in Meridian at The Oaks Preserve, is a dream come true! A penthouse-level end unit situated on the north side of the building, it has been carefully updated and meticulously maintained. From the moment you step off your private elevator you will be impressed by this spacious unit. 10 foot ceilings,

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
• 

  /2

  $1,222,500 Sold Jan 17, 2025

  • 3,020 Sq Ft
  • $405/SF
  • 25 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2006

  14021 Bellagio Way Unit 201, Osprey, FL 34229

  Welcome to Unit #201 in the exclusive Bellagio Harbor Village, where luxury meets the serene beauty of Florida’s Gulf Coast! Nestled in a prime location in Osprey, this spacious 3-bedroom, 3.5-bathroom with study condo offers nearly 3,000 sq. ft. of elegant living space designed with comfort and sophistication in mind. This luxury penthouse is currently the only unit that includes a 50 ft Boat

  Brian Wood COMPASS FLORIDA LLC

  14021 Bellagio Way Unit 201, Osprey, FL 34229
• 

  

  /72

  Est $799,577 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,802 Sq Ft

  392 Park Trace Blvd, Osprey, FL 34229

  392 Park Trace Blvd, Osprey, FL 34229
• 

  

  /50

  $789,900

  • 3 Beds
  • 3 Baths
  • 3,147 Sq Ft

  3603 N Point Rd Unit 202, Osprey, FL 34229

  **ELEGANT and SPACIOUS CORNER CONDO UNIT – NEARLY 3200sf – With MULTIPLE BALCONIES** found behind the gates of the highly sought after Oaks-Preserve neighborhood. This Light and Bright Open Floorplan offers 3 En Suite Bedrooms, 3 Baths, 2 assigned Parking spaces including 1 under building, Climate-controlled storage and much more! Crown moldings, engineered hardwood floors, expansive kitchen

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 202, Osprey, FL 34229
• 

  /2

  $579,000 Sold Jan 16, 2025

  • 2,165 Sq Ft
  • $267/SF
  • 16 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  1327 Thornapple 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 borders a greenbelt and preserve setting and tasteful landscaping that enhances its curb appeal. The enlarged lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1327 Thornapple Dr, Osprey, FL 34229
• 

  

  /60

  Est $642,710 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,363 Sq Ft

  104 Shoreland Dr, Osprey, FL 34229

  104 Shoreland Dr, Osprey, FL 34229
• 

  

  /95

  $699,000

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

  401 N Point Rd Unit 603, Osprey, FL 34229

  One or more photo(s) has been virtually staged. BEAUTIFUL FULL WATER VIEW AND 2ND FLOOR PRIVATE 2 CAR GARAGE! This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths and a formal dining room. Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 603, Osprey, FL 34229

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