Osprey, FL Homes

• 

  

  

  /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

  $1,450,000 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
• 

  

  /2

  Est $619,508 Not Listed For Sale

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

  385 N Point Rd Unit 602, Osprey, FL 34229

  385 N Point Rd Unit 602, Osprey, FL 34229
• 

  

  

  /50

  $749,000

  • 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 with

  Mark Lyda GENEROUS PROPERTY

  3603 N Point Rd Unit 202, 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
• 

  /2

  Est $501,198 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,977 Sq Ft

  515 Oak Bay Dr, Osprey, FL 34229

  515 Oak Bay Dr, Osprey, FL 34229
• 

  /2

  $800,000

  • Land
  • 0.55 Acre
  • $1,454,545 per Acre

  0 Hidden Bay Dr, Osprey, FL 34229

  The Development Site is a lakefront parcel overlooking the community’s internal lake and clubhouse. The concept plan shows 24 2-3 bedroom units in 4 stories over parking, but the parcel has unprecedented zoning and entitlements for up to 42 units. All utilities and the roads are to the development site. The utilities, roads, and parking areas, the gated entrance and the resort-style amenities are

  Bob Morris SVN COMMERCIAL ADVISORY GROUP

  0 Hidden Bay 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
• 

  

  /32

  Est $249,585 Not Listed For Sale

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

  237 Woodland Dr Unit 237, Osprey, FL 34229

  237 Woodland Dr Unit 237, Osprey, FL 34229
• 

  

  /61

  $5,500,000 New Construction

  • 3 Beds
  • 4.5 Baths
  • 4,048 Sq Ft

  614 Bayshore Dr, Osprey, FL 34229

  New Seawall / Waterside deck, New Automated Gate, Lanai Automated Screens Commanding over half an acre with 116 feet of pristine frontage on Little Sarasota Bay, this brand-new custom estate captures the essence of coastal luxury. From the moment you arrive, you are greeted by sweeping water views and spectacular Casey Key sunsets, setting the stage for an extraordinary lifestyle. Designed for

  Inbal August DOUGLAS ELLIMAN

  614 Bayshore Dr, 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
• 

  

  /34

  Est $598,804 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,163 Sq Ft

  1358 Thornapple Dr, Osprey, FL 34229

  1358 Thornapple Dr, Osprey, FL 34229
• 

  

  /6

  $145,000 Pending

  570 Blackburn Point Rd Unit 19, Osprey, FL 34229

  Highly desirable floor-level T-Top boat rack at Osprey Harbor Village with 12 ft of height! This XL rack accommodates vessels up to 30.5L x 10W x 12H and offers quick access to Midnight Pass and Venice Inlet. Marina amenities include call-ahead splash, fuel, ice, bait and tackle, fish cleaning station, adjacent restaurant, maintenance racks, and wash-down service after each use. Monthly condo

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 19, 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
• 

  

  /42

  Est $583,556 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,079 Sq Ft

  564 Crane Prairie Way, Osprey, FL 34229

  564 Crane Prairie Way, Osprey, FL 34229
• 

  

  /49

  $867,000 Pending

  • 3 Beds
  • 2 Baths
  • 2,483 Sq Ft

  678 Crane Prairie Way, Osprey, FL 34229

  It’s always about the view and the new tile roof in June 2025 plus the Tesla whole-house solar system comprising 26 roof panels harnessing 8.45-kilowatt capacity of energy. This incredible benefit includes two Power Walls and a wall-mounted charging station supporting most brands of electric vehicles. The solar system reduces house energy costs to $27 a month and zero for your electric car. When

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  678 Crane Prairie Way, 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
• 

  

  /3

  Est $663,713 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,630 Sq Ft

  6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 403, Osprey, FL 34229
• 

  

  /92

  $5,700,000 Pending

  • 6 Beds
  • 5 Baths
  • 4,893 Sq Ft

  622 Bayshore Dr, Osprey, FL 34229

  ELEVATED ABOVE FLOOD LEVEL WITH EXCEPTIONALLY LOW INSURANCE PREMIUMS ! Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle

  Debra Pitell-Hauge MICHAEL SAUNDERS & COMPANY

  622 Bayshore Dr, 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
• 

  

  /42

  Est $876,186 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,283 Sq Ft

  172 Sea Anchor Dr, Osprey, FL 34229

  172 Sea Anchor Dr, Osprey, FL 34229
• 

  

  /40

  $539,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,082 Sq Ft

  1313 Thornapple Dr, Osprey, FL 34229

  Stunning finishes welcome you to this enchanting Lee Wetherington-built residence in Willowbend. This Extended Cypress floor plan is the best use of space, remarkably accommodating three bedrooms and three full baths plus den/office with a great room design. Each bedroom is placed in separate quadrants of the home for privacy. Incredibly light and bright home has been perfected by discerning

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1313 Thornapple Dr, 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
• 

  

  /85

  Est $922,175 Not Listed For Sale

  • 5 Beds
  • 4.5 Baths
  • 3,420 Sq Ft

  184 Park Trace Blvd, Osprey, FL 34229

  184 Park Trace Blvd, Osprey, FL 34229
• 

  

  /24

  $925,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,328 Sq Ft

  3957 Waypoint Ave, Osprey, FL 34229

  A beautiful story book home of Coastal living with mainland conveniences is ready for your discovery. Come see Bayside on Little Sarasota Bay a peaceful and friendly gated Intracoastal community of 49 landscape maintenance-free residences. Bayside residents enjoy access to a private waterfront park overlooking the intracoastal waterway view of Casey Key...oh the sunsets we have for you. Under

  Leonard Giarrano RE/MAX ALLIANCE GROUP

  3957 Waypoint Ave, Osprey, FL 34229
• 

  /2

  $670,000 Sold Jan 15, 2025

  • 2,658 Sq Ft
  • $252/SF
  • 71 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2002

  193 Willow Bend Way, Osprey, FL 34229

  Adorable South Sarasota, Custom Built, 3-Bed, 3-Bath, pool home in highly desirable, centrally located Park Trace Estates. New tile roof installed July 2024 & new interior paint, new carpet, stainless refrigerator & range in 2024, Dual -Zone AC 2018. In 2007 an addition was added with option for In-Law Suite, Game Room, or large office. This home offers low HOA fees, great curb appeal and

  Bill Cantrell FLORIDA HOME TEAM LLC

  193 Willow Bend Way, Osprey, FL 34229
• 

  /2

  Est $1,200,063 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 4,071 Sq Ft

  110 N Creek Ln, Osprey, FL 34229

  110 N Creek Ln, Osprey, FL 34229
• 

  

  /84

  $2,550,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,640 Sq Ft

  432 Sorrento Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Experience the ultimate boating lifestyle from this custom-built waterfront home on a peaceful cul-de-sac.Sitting high and dry at 12 feet, the home was fully renovated for it’s current owners in 2020. Built well after the 2002 Florida Building Code changes (which required structures to be engineered for improved hurricane resistance, including impact

  Tanya Waxler UKEEPCOMMISSION REAL ESTATE

  432 Sorrento Dr, Osprey, FL 34229
• 

  /2

  $1,000,000 Sold Jan 10, 2025

  • 2,187 Sq Ft
  • $457/SF
  • 97 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 2006

  14021 Bellagio Way Unit 204, Osprey, FL 34229

  Million Dollar Water Views from Every Major Room. This is your chance to buy one of the best units in this great development. Updated to the highest standard. Located on the first floor, which gives easy access to Pool/Spa & Grille/Smoker area. Impressive views of the Bay & Marina. Elevator to your own front entry & into an impeccable Condo. Entry Foyer has Storage Closet & Powder Room. Then step

  Kym Biggar ALLISON JAMES ESTATES & HOMES

  14021 Bellagio Way Unit 204, Osprey, FL 34229
• 

  

  /25

  Est $561,745 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,126 Sq Ft

  846 Oak Pond Dr, Osprey, FL 34229

  846 Oak Pond Dr, Osprey, FL 34229
• 

  

  /57

  $674,900 Pending

  • 3 Beds
  • 2 Baths
  • 2,171 Sq Ft

  866 Placid Lake Dr, Osprey, FL 34229

  Under contract-accepting backup offers. Immerse yourself in the blissful lifestyle located in the Woodlands of Rivendell, where this beautifully appointed home awaits. Situated within a community renowned for its expansive green spaces, parks, 24 shimmering lakes, proximity to Oscar Scherer State Park, heated community pool and nearby Pine View School, this residence offers a truly exceptional

  Justin Brunswick KELLER WILLIAMS ON THE WATER S

  866 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $495,000 Sold Dec 27, 2024

  • 2,116 Sq Ft
  • $234/SF
  • 88 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1995

  502 Oak Bay Dr, Osprey, FL 34229

  INCREDIBLE NEW PRICE WITH ALL THE STORM MITIGATION UPDATES COMPLETED FOR YOU! Don't miss the opportunity own this lovely three bedroom two bath home on a private .27 acre cul de sac lot backing up to a treed preserve. Updates include NEW ROOF IN 2021, PLUMBING RE-PIPED IN 2022, WATER HEATER IN 2019, A/C IN 2016, IMPACT WINDOWS & DOORS IN 2009 ALONG WITH HURRICANE SHUTTERS TO ENCLOSE THE REAR

  Carey Beychok RE/MAX ALLIANCE GROUP

  502 Oak Bay Dr, Osprey, FL 34229
• 

  

  /79

  Est $564,671 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,217 Sq Ft

  587 Meadow Sweet Cir, Osprey, FL 34229

  587 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /30

  $1,600,000 Pending

  • Land
  • 11.68 Acres
  • $136,986 per Acre

  500 Shotgun Ln, Osprey, FL 34229

  Under contract-accepting backup offers. Truly a rare piece of Florida, a Natural Beauty! More than 11 acres in the heart of it all, west of I-75; Vacant land this size in Osprey’s sought-after Pine Ranch area is now very rare and seldom comes on the market.Discover an incredible opportunity to own 11.69 acres of vacant land in a highly desirable and rapidly growing area! Whether you're an

  Ruediger Weiss CHARITY & WEISS INTERNATIONAL LLC

  500 Shotgun Ln, Osprey, FL 34229
• 

  /2

  $750,000 Sold Dec 20, 2024

  • 1,950 Sq Ft
  • $385/SF
  • 14 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2019

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

  Fully furnished three-bedroom, 2.5-bath unit with elevator access. This fourth-floor residence offers beautiful panoramic water views. Centrally between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community on the water's edge of Little Sarasota Bay in Osprey. The building is designed in the architectural style of Key West. Enjoy

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

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

  /2

  Est $479,958 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,219 Sq Ft

  230 Burney Rd, Osprey, FL 34229

  230 Burney Rd, Osprey, FL 34229
• 

  

  /64

  $4,750,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,582 Sq Ft

  1049 N Casey Key Rd, Osprey, FL 34229

  Under contract-accepting backup offers. Seize the opportunity to own a piece of paradise on the exclusive North Casey Key. This sprawling one-plus-acre estate, with 107 feet of pristine gulf frontage, a walkable sandy beach, on a private road with security offering unparalleled privacy, is your personal slice of heaven. Surrounded by majestic live oaks, this property is a rare gem that embodies

  Courtney Green PREMIER SOTHEBYS INTL REALTY

  1049 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $295,000 Sold Dec 17, 2024

  • 1,316 Sq Ft
  • $224/SF

  • 2 Beds
  • 2 Baths
  • Built 1979

  104 Woodland Place, Osprey, FL 34229

  Serene sanctuary in a pet-friendly, resort-style community. Pine Run is known for its “Old Florida” character complimented by unique architecture. Units are designed with few if any common walls & offers a feeling of living with nature. This condo is no exception, with a large screened-in porch, bedroom privacy gardens, fenced patio, & private atrium, providing a light, bright feel to the entire

  Stellar Non-Member Agent STELLAR NON-MEMBER OFFICE

  104 Woodland Place, Osprey, FL 34229
• 

  

  /64

  Est $481,374 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,404 Sq Ft

  128 Villa Dr Unit 128, Osprey, FL 34229

  128 Villa Dr Unit 128, Osprey, FL 34229
• 

  

  /46

  $236,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,480 Sq Ft

  158 Edgewood Dr, Osprey, FL 34229

  Welcome to 158 Edgewood Drive, a furnished home in the desirable 55+ community of The Arbors in Osprey. Imagine starting your mornings in the Florida room at the front of the house, a perfect spot to sip your coffee while watching the neighborhood wake up or perhaps turning it into a peaceful home office. Inside, the easy-care laminate flooring flows through the main living areas, while the

  Renee Marquiss NEXTHOME IN THE SUN

  158 Edgewood Dr, Osprey, FL 34229

Showing Results 441 - 480, Page 12 of 18