Osprey, FL 1-Story Homes for Sale

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  /56

  $769,000

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

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229

  Waterfront living and a true boater’s lifestyle await in this meticulously maintained end-unit residence located in the gated, amenity-rich community of Blackburn Harbor in Osprey. This beautifully upgraded condo offers sweeping Intracoastal water views with Gulf glimpses, abundant natural light, and exceptional privacy within an exclusive boutique building of only 15 residences. BEING SOLD WITH

  

  Scott Swonger

  HOMESMART

  (941) 304-4466

  6100 Jessie Harbor Dr Unit 203, Osprey, FL 34229
• Explore Osprey

• 

  

  

  /90

  $1,125,000

  • 3 Beds
  • 3 Baths
  • 3,297 Sq Ft

  1218 Yacht Harbor Dr, Osprey, FL 34229

  Attention water lovers... take a look at this home 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.

  

  Karie Backman

  KELLER WILLIAMS ON THE WATER S

  (941) 352-2028

  1218 Yacht Harbor Dr, Osprey, FL 34229
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  /91

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,208 Sq Ft

  480 Oriskany Ct, Osprey, FL 34229

  Tucked away on a quiet street within the prestigious Oaks Club, this elegant residence overlooks the fairway of the Heron 14. This is a rare opportunity to find a home on a premium golf course lot and have the additional privacy of a preserve view across the street. Designed by Toll Brothers, this meticulous 3 bedroom; plus den home offers gracious, entertaining and comfortable everyday living. A

  

  Susan Pelton

  MICHAEL SAUNDERS & COMPANY

  (941) 491-3516

  480 Oriskany Ct, Osprey, FL 34229
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  /74

  $1,695,000

  • 3 Beds
  • 3.5 Baths
  • 3,066 Sq Ft

  25 Sugar Mill Dr, Osprey, FL 34229

  METICULOUSLY MAINTAINED AND THOUGHTFULLY UPDATED, THIS EXCEPTIONAL RESIDENCE IS PRIVATELY SITUATED ON A SERENE LOT WITH BEAUTIFUL GARDEN AND PRESERVE VIEWS. Located in Flood Zone “X” (no flood insurance required), the home is tucked behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. The home offers 3 En Suite

  Mark Lyda GENEROUS PROPERTY

  25 Sugar Mill Dr, Osprey, FL 34229
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  /82

  $1,295,000

  • 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 a

  Deborah Frederick ASHTON LAKES REALTY INC

  296 Pine Ranch Trail, Osprey, FL 34229
• 

  

  /75

  $2,100,000

  • 4 Beds
  • 5.5 Baths
  • 4,346 Sq Ft

  538 Dove Pointe, Osprey, FL 34229

  **ELEGANT UPDATED RESIDENCE IN THE OAKS | MODERN COMFORT ON A .83-ACRE CORNER LOT** Welcome to 538 Dove Pointe, an exceptional residence in the secure and gated Oaks Country Club community in Osprey, Florida. Set on a generous .83-acre elevated lot, this beautifully landscaped property offers the perfect combination of privacy, sophistication, and modern comfort. Built in 2002, this newer home

  Mark Lyda GENEROUS PROPERTY

  538 Dove Pointe, Osprey, FL 34229
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  /62

  $850,000

  • 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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  /43

  $899,000

  • 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
• 

  

  /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 features

  Mark Lyda GENEROUS PROPERTY

  360 N Point Rd, Osprey, FL 34229
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  /68

  $1,995,000

  • 4 Beds
  • 4 Baths
  • 2,572 Sq Ft

  312 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 six-foot depth at mean low tide, the marina can accommodate 175 boats owned

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  312 Yacht Harbor Dr, Osprey, FL 34229
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  /99

  $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. This incredible offering has everything you need to live a luxury condominium lifestyle in comfort and ease; 3 bedrooms, 3 full baths, a formal dining room and a 2ND FLOOR PRIVATE 2 CAR GARAGE! Add to this, gorgeous views from almost every room, and you have found a well-priced gem in Meridian at The Oaks Preserve to enjoy all the Gulf Coast has to

  Steve Abbe COLDWELL BANKER REALTY

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

  

  /23

  $4,750,000

  • 4 Beds
  • 4 Baths
  • 3,462 Sq Ft

  854 N Casey Key Rd, Osprey, FL 34229

  On the quiet and coveted stretch of North Casey Key, where century-old oaks meet the shoreline, and the land unfolds uninterrupted from Gulf to bay, this extraordinary 1.5-acre estate offers a rare opportunity to steward one of the island’s most incredible homesites. With 180 feet of private Gulf frontage and exceptional depth across to the intercoastal, the property is defined by its scale,

  Charles Ruck POTTER TRINITY

  854 N Casey Key Rd, Osprey, FL 34229
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  /78

  $388,000

  • 2 Beds
  • 2 Baths
  • 1,574 Sq Ft

  124 Revolution Way, Osprey, FL 34229

  The only available home in the community with a 2 Car Garage! Welcome to Bay Street Village, a charming, beach-close, gated community in sought-after Osprey. This rarely available First-Floor residence features an oversized two-car garage with exceptional space for vehicles, bikes, kayaks, and all your Florida adventure gear. Ideally situated on a quiet cul-de-sac with peaceful pond views, this

  James Briley COLDWELL BANKER REALTY

  124 Revolution Way, Osprey, FL 34229
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  /38

  $645,000

  • 4 Beds
  • 2 Baths
  • 2,217 Sq Ft

  472 Park Trace Blvd, Osprey, FL 34229

  Located in the highly desired Park Trace Estates, this beautifully maintained 4-bedroom pool home sits on a premium corner lot and is truly move-in ready. Recent upgrades include a NEW TILE ROOF and IMPACT WINDOWS, offering peace of mind and energy efficiency. The entire house has a LEAFHOME WATER FILTRATION SYSTEM, ensuring clean, high-quality water throughout. The spacious layout is perfect for

  Damon Zuchelli SUNDANCE REAL ESTATE SERVICES

  472 Park Trace Blvd, 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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  /63

  $799,000

  • 4 Beds
  • 3.5 Baths
  • 2,854 Sq Ft

  919 Tranquility Cir, Osprey, FL 34229

  WOW! TOTAL OF 50,000 PRICE ADJUSTMENT! RARE OPPORTUNITY to own this stunning former John Cannon model home on peaceful Tranquility Circle . This pristine 4BR/3.5BA pool home is a kayaker and nature lover’s paradise on North Creek with direct access to Little Sarasota Bay via Kayak or Canoe offering abundant wildlife and serene water views. Enjoy your own "Selby Garden" like setting .So hard to

  Ann Winger TIDELINE REAL ESTATE BROKERS

  919 Tranquility Cir, Osprey, FL 34229
• 

  

  /47

  $595,000

  • 4 Beds
  • 3 Baths
  • 2,557 Sq Ft

  104 Park Trace Blvd, Osprey, FL 34229

  Welcome to this elegant and spacious luxury pool home offering over 2,500 square feet of refined living in one of the most desirable communities along the Gulf Coast. With a freshly painted exterior, stunning hardwood floors throughout, and an exceptional layout designed for both comfort and style, this residence is move-in ready and perfectly suited for modern living. Boasting four bedrooms,

  Lisa Morreale PREMIER SOTHEBY'S INTERNATIONAL REALTY

  104 Park Trace Blvd, Osprey, FL 34229
• 

  

  /70

  $897,000

  • 3 Beds
  • 3 Baths
  • 2,870 Sq Ft

  664 Crane Prairie Way, Osprey, FL 34229

  It’s always about the view and the new tile roof December 2025. This stunning waterfront home in Willowbend, bordering community greenbelt with views to Oscar Scherer State Park, is a luxurious Lee Wetherington-built Paloma floorplan designed to the highest standards, offering spectacular views and seamless indoor-outdoor living. On one of the community’s most desirable lots, it features

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  664 Crane Prairie Way, Osprey, FL 34229
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  /70

  $2,274,900

  • 5 Beds
  • 3.5 Baths
  • 3,236 Sq Ft

  180 Lookout Point Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club with deep water marina and available boat slips, the opportunity to walk to your boat in a deep water marina with your home resting safely in Flood Zone X (where flood insurance is not even required by lenders) doesn't come along often. This is an extraordinary

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  180 Lookout Point Dr, Osprey, FL 34229
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  /92

  $900,000

  • 3 Beds
  • 2 Baths
  • 2,216 Sq Ft

  21 Bayhead Ln, Osprey, FL 34229

  Looking for a home you can fall in love with? The search is over! Once you see this thoughtfully updated, impeccably maintained 3 bedroom, 2 bath home in The Oaks Preserve you will know you have found your home-sweet-home. From the moment you pull up to the pavered driveway, the care taken to maintain this property is evident. Walk past the two-car garage to the pretty, double front doors with

  Steve Abbe COLDWELL BANKER REALTY

  21 Bayhead Ln, Osprey, FL 34229
• 

  

  /58

  $399,000

  • 2 Beds
  • 2 Baths
  • 1,479 Sq Ft

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229

  In the lush and serene grounds of this private and peaceful community is a best-kept secret with a name that says it all. Within Hidden Bay, this condominium gem resides in a spot on the community lake with a stunning view and soothing sound of waterfalls from your own enclosed lanai. Fully furnished with mostly all new furniture in the owners’ suite, including a new king-size mattress, living

  Pat McMillan PREMIER SOTHEBY'S INTERNATIONAL REALTY

  291 Hidden Bay Dr Unit 102, Osprey, FL 34229
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  /95

  $1,380,000

  • 3 Beds
  • 2 Baths
  • 1,824 Sq Ft

  365 S Shore Dr, Osprey, FL 34229

  Wake up to ever-changing INTRACOASTAL VIEWS – SUNSETS dancing across the water, BOATS gliding by, and untouched wildlife. Set on an EXTRA-DEEP WATER FRONT LOT with GULF ACCESS, this exceptional residence offers a rare blend of privacy, sweeping WATERFRONT views, timeless COASTAL DESIGN, and a DOCK WITH A 10,000LB BOAT LIFT that places open water just minutes away. A BOATERS PARADISE, this refined

  Lisa Asaro EXIT KING REALTY

  365 S Shore Dr, Osprey, FL 34229
• 

  

  /25

  $119,000 Open House 3/15

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  348 Tropic Dr, Osprey, FL 34229

  Perfect Home for a SNOW BIRD OR A "YEAR-ROUNDER "!! The Arbors is the BEST of the Florida sun belt communities. THE ROOF -- New in 2022 with 15-Year Transferable Waranty. THE CARPORT -- New 2023 No leaks. This lovingly maintained manufactured home is in a PET FRIENDLY zone. Your LOW $215/month HOA provides: YOUR Water. YOUR Sewer. YOUR Lawn care. YOUR Cable service. A lucky buyer could move in

  John Alexander FINE PROPERTIES

  348 Tropic Dr, Osprey, FL 34229
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  /93

  $980,000

  • 2 Beds
  • 2 Baths
  • 2,071 Sq Ft

  227 Saint James Park, Osprey, FL 34229

  Experience the charm and wonderful location of this golf course home on Saint James Park, the leafy and quiet cul-de-sac where you can walk to tennis, golf, pickleball, croquet, heated pool and state of the art fitness center all within The Oaks Country Club, where the luxury lifestyle awaits! This 2 bedroom, 2 bath traditional home overlooks the first hole of the Eagle Golf course, and is being

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  227 Saint James Park, Osprey, FL 34229
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  /100

  $1,650,000

  • 3 Beds
  • 3.5 Baths
  • 3,872 Sq Ft

  422 Blue Garden Ln, Osprey, FL 34229

  A grand traditional residence, this 3-bedroom, 3.5-bath home is tucked into lush tropical landscaping on a quiet cul-de-sac in The Oaks Bayside. Double entry doors open to a marble foyer and wood floors that set the tone for quality throughout. Just off the entry, a cozy den with fireplace sits opposite a spacious guest suite. The heart of the home is the light-filled great room, with formal

  Steve Abbe COLDWELL BANKER REALTY

  422 Blue Garden Ln, Osprey, FL 34229
• 

  

  /96

  $990,000

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

  401 N Point Rd Unit 504, Osprey, FL 34229

  FULLY UPDATED • WATER VIEWS • PRIVATE 2-CAR GARAGE • OFFICE/4TH BEDROOM OPTION From the moment the private elevator opens into your foyer, this residence reveals itself as a home crafted with intention, artistry, and a deep appreciation for its natural surroundings. Sunlight fills the space as water and preserve views stretch out beyond the generous lanai—an ever-changing backdrop that greets you

  Mary Elizabeth Mock COLDWELL BANKER REALTY

  401 N Point Rd Unit 504, Osprey, FL 34229
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  /56

  $974,900

  • 4 Beds
  • 3.5 Baths
  • 2,980 Sq Ft

  1602 Southbay Dr, Osprey, FL 34229

  Welcome to your slice of Florida paradise!Nestled on a spacious corner lot in the highly sought-after Southbay Yacht & Racquet Club, this elegant residence captures the essence of the coastal lifestyle—enhanced by thoughtful recent updates including a new roof replaced in 2023, fresh interior paint, an updated kitchen, and a beautifully updated pool and jacuzzi. As you arrive, mature tropical

  Thomas Kiessling COMPASS FLORIDA LLC

  1602 Southbay Dr, Osprey, FL 34229
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  /36

  $580,000

  • 3 Beds
  • 2 Baths
  • 2,172 Sq Ft

  1337 Copperwood 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 with a sparkling pool and lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases meticulous attention to detail with features such as high ceilings,

  Todd Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1337 Copperwood Dr, Osprey, FL 34229
• 

  

  /55

  $515,000

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

  120 Villa Dr Unit 120, Osprey, FL 34229

  Waterfront with your own private dock with 10,000lb elevator lift. This home is being offered fully furnished from the inside out to the lanai and boat dock. The kitchen features raised wood cabinets and a large 10ft long breakfast bar. The kitchen has views of the canal and opens up to the dining room and living room. As you walk into the nicely appointed open floor plan, you immediately feel

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  120 Villa Dr Unit 120, Osprey, FL 34229
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  /39

  $1,099,000

  • 3 Beds
  • 2 Baths
  • 2,374 Sq Ft

  14041 Bellagio Way Unit 218, Osprey, FL 34229

  Elevate your expectations with this elegant waterfront home! This 3-bedroom, 2-bath FULLY FURNISHED home offers 2,374 sq ft of well-appointed living space, with water views of Little Sarasota Bay from every main room. Located in one of Osprey’s most desirable boutique waterfront communities, this condo includes a DEEDED 40' wet slip—providing immediate access to boating, fishing, and the

  Kelli Eggen COLDWELL BANKER REALTY

  14041 Bellagio Way Unit 218, Osprey, FL 34229
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  /42

  $829,000

  • 4 Beds
  • 3 Baths
  • 2,876 Sq Ft

  1211 Lost Creek Ct, Osprey, FL 34229

  **BEAUTIFULLY UPDATED AND MOVE-IN READY, THIS SPACIOUS 4-BEDROOM + OFFICE/DEN HOME OFFERS NEARLY 2,900 SQUARE FEET** of thoughtfully designed living space with potential for a private in-law or multi-generational suite. Featuring 3 full baths and a coveted 3-car garage, this reconfigured floor plan provides flexibility, privacy, and comfort for today’s lifestyle.Situated on an ideal corner

  Mark Lyda GENEROUS PROPERTY

  1211 Lost Creek Ct, Osprey, FL 34229
• 

  

  /60

  $559,000

  • 2 Beds
  • 2 Baths
  • 1,555 Sq Ft

  786 Sarabay Rd Unit 19, Osprey, FL 34229

  Secluded waterfront community on Little Sarasota Bay with access to the Intracoastal Waterway and the Gulf. Heron Bay Club has boat slips available! This small community on Little Sarasota Bay offers striking sunsets. Across from the northern section of Casey Key, the 10-acre property features 26 villas. This complex is intimate, quiet and peaceful. Part of the reason for the relaxing atmosphere

  Michael Christo PREMIER SOTHEBYS INTL REALTY

  786 Sarabay Rd Unit 19, Osprey, FL 34229
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  /92

  $1,775,000 Pre-Foreclosure

  • 4 Beds
  • 4 Baths
  • 4,001 Sq Ft

  75 Osprey Point Dr, Osprey, FL 34229

  **STUNNING ARCHITECTURAL ESTATE in the coveted OAKS BAYSIDE Country Club Neighborhood** on Sarasota Bay waters... situated on TWO LOTS totaling over 3/4 acres, the Main House on Lot #1 features 3 Beds / 3 Baths while the separate Guest House on adjacent Lot #2 boasts 1 Bed / 1 Bath, kitchenette, laundry, etc. An oversized Pool adorns the private setting with lush landscape and water view. This

  Mark Lyda GENEROUS PROPERTY

  75 Osprey Point Dr, Osprey, FL 34229
• 

  

  /59

  $585,000

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

  711 Shadow Bay Way, Osprey, FL 34229

  Condition, Condition, Condition – AND Location, Location, Location!! This house is a real gem! Immaculate and beautifully updated, it features 4 bedrooms (or 3 plus a den with a closet) in a split plan that provides privacy for owners and guests. When you sit on the front porch of this contemporary style home, you’ll enjoy an uninterrupted front yard, since the garage opens to the rear of the

  Susan Keal MICHAEL SAUNDERS & COMPANY

  711 Shadow Bay Way, Osprey, FL 34229
• 

  

  /41

  $185,000 Open House 3/15

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  238 Palm Air Dr, Osprey, FL 34229

  AN ARBORS BEAUTY in one of Florida’s most-sought-after 55+ parks. You won’t believe how BIG and BEAUTIFUL this home is !! Over 1,152 square feet of centrally-cooled comfort. Large living room. New laminate flooring. A chef’s kitchen. Comfy throughout. 2 LANAIS: (1) Front lanai with new windows and new tile flooring; (2) Side lanai is carpeted, screened and ready for relaxing. Both lanais add more

  John Alexander FINE PROPERTIES

  238 Palm Air Dr, Osprey, FL 34229
• 

  

  /45

  $649,000

  • 3 Beds
  • 2.5 Baths
  • 2,292 Sq Ft

  659 Rivendell Blvd, Osprey, FL 34229

  Located within The Woodlands at Rivendell, this meticulously maintained single-family residence offers a sophisticated balance of comfort, functionality, and tranquil natural surroundings. Backing to a serene lake and protected preserve, the home enjoys exceptional privacy and peaceful water views. Designed with an open, split-bedroom floor plan, the residence features three bedrooms, two full

  Stephanie Church COLDWELL BANKER REALTY

  659 Rivendell Blvd, Osprey, FL 34229
• 

  

  /88

  $650,000

  • 5 Beds
  • 2.5 Baths
  • 2,746 Sq Ft

  571 Pine Ranch Rd E, Osprey, FL 34229

  One of the largest homes in Bay Oaks Estates, with the second-largest floor plan in the community, this 5-bedroom, 2.5-bath single-story pool retreat delivers the best of indoor-outdoor Florida living with flexible spaces for guests, work, and play. Curb appeal pops with a brick paver circular drive, lush, well-established landscaping highlighted by a mature magnolia and fragrant gardenias, and a

  Christiana Kopetzky MICHAEL SAUNDERS & COMPANY

  571 Pine Ranch Rd E, Osprey, FL 34229
• 

  

  /43

  $639,000

  • 4 Beds
  • 2 Baths
  • 2,145 Sq Ft

  819 Shadow Bay Way, Osprey, FL 34229

  Welcome to this stunning 2,145-square-foot pool home in the premier community of Rivendell where maintenance-free living meets tropical elegance. Perfectly positioned on a beautifully landscaped corner lot, this meticulously maintained residence offers timeless style and thoughtful updates throughout. Recent improvements include a 2026 irrigation valves, 2025 roof replacement, 2024 pool pump, and

  Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

  819 Shadow Bay Way, Osprey, FL 34229
• 

  

  /48

  $724,900

  • 4 Beds
  • 2 Baths
  • 2,111 Sq Ft

  597 Oak River Ct, Osprey, FL 34229

  Stunning, fully remodeled 4-bedroom, 2-bathroom home tucked away in a quiet cul-de-sac in the heart of Osprey, showcasing over $250,000 in high-end upgrades. Every detail has been thoughtfully curated, beginning with the spectacular gourmet kitchen featuring an 11-foot quartz waterfall island with abundant storage, Bosch appliances including an induction cooktop and counter-depth refrigerator,

  Mairead Smialek COLDWELL BANKER REALTY

  597 Oak River Ct, Osprey, FL 34229
• 

  

  /40

  $350,000

  • 3 Beds
  • 2 Baths
  • 1,430 Sq Ft

  4284 Expedition Way, Osprey, FL 34229

  Welcome to Bay Street Village, a gated, maintenance-free community in Osprey between Sarasota and Venice. The tile roofs and paver driveway provide Florida charm. This move-in-ready 3-bed, 2-bath condo features an open layout, IMPACT glass, and a private screened balcony with a pond view. The kitchen offers a large granite counter with seating and a newer refrigerator. The primary suite includes

  Grace Bonaccorso PREFERRED SHORE LLC

  4284 Expedition Way, Osprey, FL 34229

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