Osprey, FL Homes for Sale

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  /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
• Explore Osprey

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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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  /41

  $350,000

  • 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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  /65

  $1,075,000

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

  701 Eaglenook Way, Osprey, FL 34229

  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. Situated at the end of a

  

  Michael Ballantyne

  COLDWELL BANKER SARASOTA CENT.

  (941) 883-9471

  701 Eaglenook Way, Osprey, FL 34229
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  /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
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  /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
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  /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
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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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  /80

  $2,995,000

  • 4 Beds
  • 4 Baths
  • 4,359 Sq Ft

  662 Fernwalk Ln, Osprey, FL 34229

  **FANTASTIC, FULLY RENOVATED ESTATE with LAKE / GARDEN VIEW is situated on a SERENE, INTERIOR, CUL-DE-SAC lot with NO FLOOD concern (Zone “X”) behind the Secure Gates of the highly sought after Bayside neighborhood within The Oaks Country Club community, just steps from Little Sarasota Bay. An Expansive Floorplan entails 4-BEDs plus 4-FULL BATHS while a full list of EXCEPTIONAL FEATURES is

  Mark Lyda GENEROUS PROPERTY

  662 Fernwalk Ln, 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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  /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 for your

  Mike Aveni KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  280 Hidden Bay Dr Unit 202, 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

  $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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  /76

  $2,150,000

  • 3 Beds
  • 3 Baths
  • 4,191 Sq Ft

  85 Sugar Mill Dr, Osprey, FL 34229

  **STUNNINGLY DESIGNED and UPDATED -- ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Little Sarasota Bay waters features 3 BEDS plus DEN/OFFICE, 3 FULL BATHS and incredible detail throughout including beautiful crown moldings, volume ceilings, hardwood floors, wainscoting, plantation shutters, LED lighting accents and MORE! NEW ROOF (2020). The CHEF’s KITCHEN

  Mark Lyda GENEROUS PROPERTY

  85 Sugar Mill Dr, Osprey, FL 34229
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  /49

  $1,175,000

  • 3 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  219 Keel Way, Osprey, FL 34229

  **IMPRESSIVE, METICULOUSLY MAINTAINED, SINGLE-STORY, CUL DE SAC ESTATE in the Highly Sought-After SOUTHBAY Community** offers 3 BEDS, 2 FULL and 1 HALF BATHS plus STUDY/DEN – and is nearly 100% SOLAR-POWERED (details available)! This Custom and Updated home offers many premium features including elegant Bolivian woodwork, beautiful tile floors throughout, Expansive Kitchen with Hardwood Cabinets,

  Mark Lyda GENEROUS PROPERTY

  219 Keel Way, Osprey, FL 34229
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  /99

  $545,000

  • 4 Beds
  • 3 Baths
  • 2,688 Sq Ft

  447 Oak Point Rd, Osprey, FL 34229

  Prepare to be impressed as you enter this bright and spacious maintenance-free townhome with soaring ceilings, an abundance of natural light, and surrounded by nature in a wooded setting. Nestled near Casey Key, this coveted West of the Trail subdivision with only 44 single-family, attached homes, is walking distance to Casey Key, Blackburn Point Marina, and Blackburn Point Park, which features a

  Priscilla Adams COMPASS FLORIDA LLC

  447 Oak Point Rd, Osprey, FL 34229
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  /87

  $2,650,000

  • 5 Beds
  • 5.5 Baths
  • 4,783 Sq Ft

  370 Sugar Mill Dr, Osprey, FL 34229

  **Meticulously maintained, architectural perfection, this bright, spectacular estate featuring incredibly spacious first floor living space, with 5-Beds, 6.5 Baths, private second floor family, au pair and/or guest quarters, new pool, ideal Flood Zone X location, important updates, property wide landscape renovation and a 3-Car Garage. The expansive first level has extraordinary living space: a

  Mark Lyda GENEROUS PROPERTY

  370 Sugar Mill Dr, Osprey, FL 34229
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  /56

  $5,000,000

  • 4 Beds
  • 5.5 Baths
  • 5,087 Sq Ft

  101 Osprey Point Dr, Osprey, FL 34229

  A grand estate where timeless design meets lakefront tranquility, 101 Osprey Point Drive offers refined living within the private gates of The Oaks Bayside. Designed by architect Bo MacEwen, this one-of-a-kind home spans more than 5,000 square feet, all cleverly positioned on nearly an acre with 150 feet of lakefront. Situated on two of the community’s most desirable lots, the residence balances

  Joel Schemmel DOUGLAS ELLIMAN

  101 Osprey Point Dr, Osprey, FL 34229
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  /43

  $995,000

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft

  599 Pine Ranch Rd E, Osprey, FL 34229

  **EXQUISITELY UPDATED, TURNKEY FURNISHED, POOL HOME** in Popular BAY OAKS ESTATES. This Stunning Residence is MOVE-IN READY (just Bring Your Suitcase!) and features a LIGHT and BRIGHT, OPEN FLOORPLAN including 3 BEDS plus STUDY/DEN and 2 FULL BATHS. The Gourmet Kitchen boasts a modern, European design with premium appliance package and counter sitting area while the primary bedroom suite offers

  Mark Lyda GENEROUS PROPERTY

  599 Pine Ranch Rd E, Osprey, FL 34229
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  /60

  $925,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  385 N Point Rd Unit 404, Osprey, FL 34229

  **STUNNINGLY UPDATED CONDO with Breathtaking Water & Preserve Views that rival those of higher floors!** This LARGE, CORNER UNIT of nearly 2800sf features 3-Beds & 3 Full Baths PLUS Study/Den (or possible 4th Bedroom with Walk-In Closet) and 2 side-by-side Covered Parking Spaces near elevator, Etc. and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 404, Osprey, FL 34229
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  /73

  $2,550,000

  • 3 Beds
  • 3.5 Baths
  • 4,519 Sq Ft

  852 MacEwen Dr, Osprey, FL 34229

  **CHARMING and PRIVATE, GOLF COURSE ESTATE** is located behind the Secure Gates of the highly sought after Oaks Country Club community and offers a Lovely, Golf Course View of the 17th Fairway of the interior, Heron Golf Course. This Spacious, Light and Bright, Open Floorplan of OVER 4500sf entails 3-BEDS, 3 FULL and 1 HALF BATHS, Study/Den, Bonus Room / Entertaining area with Fireplace and

  Mark Lyda GENEROUS PROPERTY

  852 MacEwen Dr, Osprey, FL 34229
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  /62

  $1,499,500

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

  385 N Point Rd Unit 701, Osprey, FL 34229

  **INCOMPARABLE VIEW! 7th FLOOR, CORNER CONDO UNIT WITH UNOBSTRUCTED SOUTH AND WEST PANORAMA. This Spacious unit of nearly 2600sf features 3-Beds PLUS Study/Den, 3 Full Baths and includes a PRIVATE 2-CAR GARAGE. Located behind the Secure Gates of the Oaks-Preserve, Country Club neighborhood, this Light and Bright, Sought-after unit boasts a VIEW which you MUST EXPERIENCE TO BELIEVE from its

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 701, Osprey, FL 34229
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  /69

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,267 Sq Ft

  471 Park Trace Blvd, Osprey, FL 34229

  SIGNIFICANT PRICE IMPROVEMENT!! Welcome to your dream home! This stunning, custom-built 4 bedroom, 3 bathroom residence perfectly blends luxury, comfort, and location for the ideal Florida lifestyle. This home is nestled in a highly sought-after neighborhood offering peace, privacy, and a vibrant community feel with low HOA fees. It is situated on an over-sized corner lot, with exceptional

  Bill Cantrell FLORIDA HOME TEAM LLC

  471 Park Trace Blvd, Osprey, FL 34229
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  /68

  $1,970,000

  • 4 Beds
  • 4 Baths
  • 3,286 Sq Ft

  140 Sugar Mill Dr, Osprey, FL 34229

  **BRILLIANTY DESIGNED, FULLY RENOVATED, STUNNING and SERENE ESTATE with Lush Garden Landscape** is located behind the Secure Gates of The Oaks Bayside, Country Club neighborhood. Featuring 4 BEDROOMS (2 En Suite) and 4 FULL BATHS, this Open Floorplan with Soaring Ceilings, Custom Built-Ins, Crown Moldings and refined details throughout is ideal for entertaining both inside and out! The Impressive

  Mark Lyda GENEROUS PROPERTY

  140 Sugar Mill Dr, Osprey, FL 34229
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  /82

  $1,350,000

  • 5 Beds
  • 3.5 Baths
  • 3,481 Sq Ft

  296 Pine Ranch Trail, Osprey, FL 34229

  **THIS PROPERTY QUALIFIES FOR A LENDER INCENTIVE (up to $8,000) IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.** & SELLER IS OFFERING A $25,000.00 CREDIT toward rate buy down/closing cost with acceptable contract. Welcome to your private retreat nestled in one of Osprey’s most desirable enclaves. This beautifully situated home rests on a lush greenbelt lot that borders the fairways of

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
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  /38

  $795,000

  • 3 Beds
  • 2 Baths
  • 2,443 Sq Ft

  901 Reflection Way, Osprey, FL 34229

  LOCATION! LOCATION! Tucked away on a quiet cul-de-sac and resting on a corner lot, this METICULOUSLY MAINTAINED, Custom-built, JOHN CANNON home in exclusive North Creek Estates offers the perfect blend of privacy, luxury, and convenience. With a NEW ROOF (2020), low HOA fees, and 2,443 sq. ft. of thoughtfully designed living space, this 3-Bedroom + Office/Den, 2-Bath residence is MOVE-IN READY

  Mark Lyda GENEROUS PROPERTY

  901 Reflection Way, Osprey, FL 34229
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  /62

  $965,000

  • 2 Beds
  • 2 Baths
  • 2,310 Sq Ft

  13 Bayhead Ln, Osprey, FL 34229

  **IMPRESSIVE, MOVE-IN READY, POOL HOME in the Secure and Coveted OAKS PRESERVE, MAINTENANCE-FREE COMMUNITY** This residence boasts an open floor plan that is ideal for entertaining, along with a screened and spacious outdoor pool area that provides privacy and overlooks a nature preserve. Recent updates include a new kitchen, bathrooms, flooring, fans, a four-year-old roof, a newly pavered

  Mark Lyda GENEROUS PROPERTY

  13 Bayhead Ln, Osprey, FL 34229
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  /78

  $2,000,000

  • 4 Beds
  • 3.5 Baths
  • 4,191 Sq Ft

  453 E MacEwen Dr, Osprey, FL 34229

  Set an appointment to experience this thoughtfully designed Arthur Rutenberg home, where craftsmanship and details are truly on display. Upon entering through the double door entrance, the quality and attention to detail are immediately evident. Situated on a 1/2 acre + "premium" golf course lot strategically positioned on the Heron Course (hole 5). This residence blends timeless design with

  William Kelly THE REAL ESTATE STORE

  453 E MacEwen Dr, Osprey, FL 34229
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  /91

  $2,195,000

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

  600 Eagle Watch Ln, Osprey, FL 34229

  One or more photo(s) has been virtually staged. **BRILLIANTLY UPDATED, MOVE-IN READY, GOLF COURSE ESTATE in the Highly Sought-After OAKS COUNTRY CLUB Community** offers an Ideal Southern-Exposure and View across the 3rd Fairway of the Interior, HERON GOLF COURSE. Situated on an Oversized 0.71 Acre Lot with Circular Driveway and manicured landscape, this Extensively Renovated Home offers 3

  Mark Lyda GENEROUS PROPERTY

  600 Eagle Watch Ln, Osprey, FL 34229
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  /49

  $2,350,000

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

  18 N Casey Key Rd, Osprey, FL 34229

  Elegantly renovated bayfront retreat on Casey Key and tastefully remodeled in 2012, this stunning bayfront home blends timeless coastal elegance with modern functionality, all in one of the desired locations on Casey Key. Designed for relaxing and entertaining, the open-concept living room, kitchen, and family room offer inviting spaces to gather, while the split floor plan ensures privacy, ideal

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  18 N Casey Key Rd, Osprey, FL 34229
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  /100

  $1,200,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  401 N Point Rd Unit 404, Osprey, FL 34229

  Step into a residence that redefines elegance and sophistication. This stunning 2,778 sq ft condo has been completely reimagined. Every inch has been thoughtfully redesigned to create a truly exceptional living experience. Boasting 3 spacious bedrooms, 3 bathrooms and an expansive den, the open-concept layout flows effortlessly, offering both comfort and style. From the moment you exit your

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 404, Osprey, FL 34229
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  $599,000

  • 3 Beds
  • 3 Baths
  • 2,000 Sq Ft

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229

  This condominium has it all! Fantastic water views along the Intracoastal. Amazing sunsets from the large balcony. A private two-car garage. Three bedrooms, three full baths and 2,000 square feet of living area. The building has a new roof. The elevator was just replaced. Priced at $599,000. In the Hidden Bay community in Osprey with water views of Little Sarasota Bay and the Intracoastal

  Per Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  232 Hidden Bay Dr Unit 504, Osprey, FL 34229
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  /39

  $1,100,000

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft

  385 N Point Rd Unit 903, Osprey, FL 34229

  One or more photo(s) has been virtually staged. From the moment the private elevator doors open, the panorama of the view has you at ‘hello,” with a northwest-facing expanse over the preserve, the lagoon below, Sarasota Bay and the Gulf beyond. This orientation brings cooler interiors, dramatic natural light and unforgettable sunsets. Rare 10’ ceilings amplify the spaciousness and invite the

  Ryan Ackerman COLDWELL BANKER REALTY

  385 N Point Rd Unit 903, Osprey, FL 34229
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  /97

  $1,385,000

  • 3 Beds
  • 3.5 Baths
  • 3,112 Sq Ft

  156 Bishopscourt Rd, Osprey, FL 34229

  This stunning 3 bedroom, 3.5 bath home, designed by the renowned architect Frank Folsom Smith, stands out with its unique design. The charming Cape Cod style sets the stage for comfortable, graceful living. The home, with beautiful wood floor throughout the main living areas, features a Sonos stereo sound system. The backyard, overlooking the preserve, and offering a lovely sunset exposure, is a

  Steve Abbe COLDWELL BANKER REALTY

  156 Bishopscourt Rd, Osprey, FL 34229
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  /79

  $1,350,000

  • 3 Beds
  • 2 Baths
  • 2,850 Sq Ft

  17 Bayhead Ln, Osprey, FL 34229

  Welcome to an exquisitely revitalized estate set amidst a stunning landscape that is sure to impress. Located “West of Trail” in The Oaks Preserve, you will experience an unparalleled country club lifestyle on Florida’s Gulf Coast. As you step through the grand front entry, you are welcomed by a blend of contemporary sophistication and modern luxury, transforming this residence into a true

  Ashley LeRoy CORNERSTONE R.E OF SW FL

  17 Bayhead Ln, Osprey, FL 34229
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  /65

  $710,000

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

  250 Hidden Bay Dr Unit A302, Osprey, FL 34229

  WHAT A VIEW and the pictures don't do it justice!! SELLER HAS SATISFIED Q4 DUES AND ASSESSMENTS!!! FULLY FURNISHED/TURNKEY UNIT!!! Prepare to be captivated by jaw-dropping sunsets from your oversized, private, screened-in balcony, offering unobstructed vistas across Little Sarasota Bay to the peaceful barrier island of Casey Key. Welcome to Edgewater at Hidden Bay — a gated, 12-acre resort-style

  Merryl Koven COLDWELL BANKER REALTY

  250 Hidden Bay Dr Unit A302, Osprey, FL 34229
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  /47

  $725,000

  • 3 Beds
  • 3 Baths
  • 2,484 Sq Ft

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229

  Perched on the top floor of Blackburn Harbor Residences, this 3-bedroom, 3-bath end unit is just under 2500 square feet and offers stunning, unobstructed vistas of the intracoastal waterways and Gulf of Mexico. Located within a gated, amenity-rich community, this condo features an open floor plan with high ceilings, a spacious kitchen, and a living area that seamlessly blends indoor comfort with

  Robert Ruiz WILLIAM RAVEIS REAL ESTATE

  5100 Jessie Harbor Dr Unit 701, Osprey, FL 34229
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  /60

  $1,219,000

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  1527 Buoy Ln, Osprey, FL 34229

  Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large

  Matthew Lewis BRIGHT REALTY

  1527 Buoy Ln, Osprey, FL 34229
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  /37

  $625,000

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  One of Sarasota’s Best-Kept Secrets! Top-Floor Bayfront Retreat in Hidden Bay. 2 Bed | 2 Bath + Den | Enclosed Lanai | 2-Car Garage | Offered Fully Furnished. Perched on the top floor of a premier building in the exclusive Hidden Bay gated community, this spacious and light-filled condo offers breathtaking, panoramic views of Sarasota Bay. A true diamond in the rough, this home is ready for your

  Joy McGraw REAL ESTATE REFINED

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
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  /62

  $660,000

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

  385 N Point Rd Unit 402, Osprey, FL 34229

  **BEAUTIFULLY UPDATED CONDO with MARVELOUS VIEW** features 3-BEDS and 3-FULL BATH, Open Floorplan and is located behind the Secure Gates of the highly sought after Oaks-Preserve, Country Club neighborhood. As you emerge from your private elevator lobby, you will be enthralled by the Impressively Renovated interior which boasts Engineered Hardwood and designer Wood Plank Tile flooring, Plantation

  Mark Lyda GENEROUS PROPERTY

  385 N Point Rd Unit 402, Osprey, FL 34229

Showing Results 1 - 40, Page 1 of 4

Why Live in Osprey

Osprey, FL, a census-designated community on the Gulf Coast, is known for its vibrant outdoor spaces and waterfront living. Residents can start their day kayaking through mangroves, enjoy lunch at waterfront restaurants, and spend evenings at tiki bars on Casey Key. The area around Tamiami Trail offers numerous shopping and dining options, including fresh seafood. Osprey features a variety of home styles, from condos to Mediterranean-inspired properties and waterfront villas, often within gated communities with amenities like golf courses and clubhouses. The community is home to highly rated schools such as Gulf Gate Elementary, Pine View School, and Venice High. Outdoor enthusiasts can explore Oscar Scherer State Park, with its hiking trails and opportunities for canoeing and kayaking, or visit Bay Preserve for fishing and boating. Historic Spanish Point offers a glimpse into the region's past with its prehistoric mound and citrus packing house. For nightlife, The O Bar and Spanish Point Tiki Bar are popular spots. Osprey is car-dependent but has public transportation options and is conveniently located near major employers like Sarasota Memorial Hospital and PGT Innovations. Nearby beaches, including Nokomis Beach and Siesta Key Beach, are just a short drive away, and Sarasota Bradenton International Airport is 15 miles from the community.

Learn more about living in Osprey

Frequently Asked Questions

What is the average home price in Osprey, FL?

Homes for sale in Osprey, FL have an average home price of $1,196,861.

Are home prices dropping in Osprey?

Yes, home prices in Osprey are down 14% in the last 12 months.

How many homes have sold over the last 12 months in Osprey, FL?

174 homes have sold in Osprey, FL over the last 12 months.

What are the most popular zip codes in Osprey, FL?

The most popular zip codes in Osprey, FL include 34229, 34238, 34275, 34231 and 34239.

How much do you need to make to afford a house in Osprey?

The median home price in Osprey is $823,875. If you put a 20% down payment of $164,800 and had a 30-year fixed mortgage with an interest rate of 6.19%, your estimated principal and interest payment would be $4,030 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $173K a year to afford the median home price in Osprey.

How are the schools in Osprey, FL?

Osprey, FL has highly rated public and private schools. Some of the best schools in Osprey based on Niche Grades are Pine View School, Laurel Nokomis School and Riverview High School. Browse all the schools in Osprey, FL to learn more.

Home Trends in Osprey, FL

On average, homes in Osprey, FL sell after 94 days on the market compared to the national average of 53 days. The median sale price for homes in Osprey, FL over the last 12 months is $744,900, down 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$744,900

Median Single Family Sale Price

$879,500

Median Townhouse Sale Price

$489,000

Median 2 Bedroom Sale Price

$289,000

Median 1 Bedroom Sale Price

$177,000

Average Price Per Sq Ft

$396

Number of Homes for Sale

119

Last 12 months Home Sales

174

Months of Supply

8.20

Median List Price

$823,875

Median Change From 1st List Price

9%

Median Home Sale Price YoY Change

-12%