Osprey, FL Homes for Sale

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  /88

  $2,700,000

  • 6 Beds
  • 6.5 Baths
  • 6,246 Sq Ft

  236 Saint James Park, Osprey, FL 34229

  Tucked away in a quiet cul-de-sac on a sprawling double lot beneath majestic oaks, this nearly 5,000 sq ft timeless 2-story residence blends classic elegance with modern luxury. Perfectly positioned on the first hole of one of Sarasota’s most sought-after golf courses, the home showcases soaring 11-ft ceilings, gleaming marble floors, and dazzling crystal chandeliers. A Louis XVI fireplace

  Karin Watt MICHAEL SAUNDERS & COMPANY

  236 Saint James Park, Osprey, FL 34229
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  /66

  $895,000 Open Sun 1PM - 4PM

  • 3 Beds
  • 2.5 Baths
  • 2,676 Sq Ft

  238 Lookout Point Dr, Osprey, FL 34229

  This is an outstanding Southbay residence and a fantastic opportunity to live in one of the best boating communities on the Southwest coast of Florida. This home has been updated with a gourmet custom kitchen, perfect for entertaining guests and hosting company. From the granite countertops to the gas cooktop, and custom cabinetry, it is a pleasure to cook in here! The dining room is spacious

  Susanne Losso COLDWELL BANKER REALTY

  238 Lookout Point Dr, Osprey, FL 34229
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  /13

  $199,000

  • 2 Beds
  • 2 Baths
  • 1,578 Sq Ft

  106 Villa Dr Unit 106, Osprey, FL 34229

  Located West of the Trail in Sorrento Shores, Osprey, this spacious 2BR/2BA villa with a den and oversized 1-car garage offers 1,578 sq. ft. of comfortable living space. A boating community with private dock access and a heated pool just steps away, it’s perfect for boaters, kayakers, or anyone seeking the coastal lifestyle. Features include hurricane-rated windows and doors, updated kitchen and

  Dan Ivanov KONA REALTY

  106 Villa Dr Unit 106, Osprey, FL 34229
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  /48

  $749,000

  • 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
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  /91

  $500,000

  • 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
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  /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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  /7

  $3,000

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 28, Osprey, FL 34229

  Calling all Investors! Huge opportunity to make a deal on this perfect renovation project. Quick Closing, Quick Renovation and Quick Profit! This home needs significant work and is priced accordingly. Given the amount of work necessary to bring this gem up to it's fiull potential, prospective investors must be licensed and experienced renovation specialists. Call today, we are currently

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 28, Osprey, FL 34229
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  /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
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  /76

  $1,089,000

  • 3 Beds
  • 3 Baths
  • 2,323 Sq Ft

  3936 Waypoint Ave, Osprey, FL 34229

  Discover the charm of coastal living with the convenience of a mainland location in this beautifully furnished Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal lifestyle.Blending luxury, comfort, and coastal

  Angelic Tassos CORCORAN DWELLINGS REALTY

  3936 Waypoint Ave, Osprey, FL 34229
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  /76

  $455,000

  • 2 Beds
  • 2 Baths
  • 1,604 Sq Ft

  508 Meadow Sweet Cir, Osprey, FL 34229

  PRICE IMPROVEMENT!! The Cottages of Rivendell are highly desirable residences, offering an exclusive community with only 84 homes. Each home is surrounded by lush landscaping and tree-lined streets, contributing to the area's charm and appeal. This home features 2 bedrooms and 2 bathrooms, as well as a versatile den or office space. It is an ideal choice for those seeking a seasonal residence in

  Bill Cantrell FLORIDA HOME TEAM LLC

  508 Meadow Sweet Cir, Osprey, FL 34229
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  /32

  $3,350,000

  • 3 Beds
  • 4.5 Baths
  • 2,572 Sq Ft

  135 Tina Island Dr, Osprey, FL 34229

  Retreat to paradise in this stunning waterfront home, built new in 2011, in highly sought-after Sorrento Shores, Osprey. Perfectly situated on 210 feet of wide canal frontage, this residence offers deep water access with no bridges to the bay—a dream for boaters. Nearly every room provides breathtaking views of the water and swaying palms. Constructed with concrete block on both floors and

  Cliff Glansen FLATFEE.COM

  135 Tina Island Dr, Osprey, FL 34229
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  /71

  $585,000 Open Sun 1PM - 4PM

  • 4 Beds
  • 2 Baths
  • 2,186 Sq Ft

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229

  Welcome to this attractive St. Charles floor plan found in the desirable Woodlands at Rivendell community! This charming home sits on a large corner lot directly across from the heated community pool and is within easy reach of the highly ranked Pine View School for the Gifted (Grades:2-12). Built in 2001, this well-maintained home features four bedrooms, or three bedrooms plus den with closet,

  Helena Nordstrom PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1036 Oak Meadow Ln Unit 3A, Osprey, FL 34229
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  /96

  $2,595,000

  • 4 Beds
  • 3.5 Baths
  • 3,953 Sq Ft

  49 Osprey Point Dr, Osprey, FL 34229

  Nestled in the prestigious gated enclave of The Oaks Bayside in Sarasota, this Sedona-inspired retreat was recently updated from wall to wall creating a like brand new home. The estate seamlessly blends modern luxury, comfort, and serenity. With almost 4,000 SQF and boasting 4 generously sized bedrooms and 3 1/2 baths, this residence has been thoughtfully renovated with the finest finishes,

  Jonathan Abrams MICHAEL SAUNDERS & COMPANY

  49 Osprey Point Dr, Osprey, FL 34229
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  $660,000

  • 3 Beds
  • 2 Baths
  • 2,279 Sq Ft

  804 Shadow Bay Way, Osprey, FL 34229

  Located in one of Osprey’s most desirable neighborhoods, this well-maintained 3 bedroom, 2 bath home with a den offers an unbeatable location just a short walk to Pine View School and minutes to Casey Key and Siesta Key. Enjoy peaceful pond and greenbelt views from the screened lanai, which features a covered sitting area, pool, and a separate patio with hot tub. The open, split floor plan

  Andrew Foltz PREFERRED SHORE LLC

  804 Shadow Bay Way, Osprey, FL 34229
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  /99

  $1,197,000

  • 4 Beds
  • 3 Baths
  • 2,770 Sq Ft

  403 Longbow Trail, Osprey, FL 34229

  Welcome to this beautifully maintained 4 bed, 3 bath property nestled on a 2-acre lot in one of Osprey's most desirable communities Pine Ranch. Located 15 minutes from Siesta Key and Nokomis Beach and is within a short distance from the nationally top-rated Pine View School, #1 High School in Florida and the natural beauty of the Legacy Trail. This charming home offers a perfect blend of comfort,

  Edward Bieker DALTON WADE INC

  403 Longbow Trail, Osprey, FL 34229
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  /51

  $463,000

  • 2 Beds
  • 2 Baths
  • 2,148 Sq Ft

  32 Bay Ave, Osprey, FL 34229

  Located in the highly sought-after Bay Acres community, this home offers modern upgrades, spacious living, and access to one of the area’s most desirable boating lifestyles. Recent updates include a metal roof, 2018 HVAC system with all-new ductwork, 2022 whole-house re-plumb including sewer lines, underground electric and 200-amp electrical panel, new septic system, water heater, and stainless

  Julie Willett NEXTHOME BEACH TO BAY

  32 Bay Ave, Osprey, FL 34229
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  /8

  $16,995

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 5, Osprey, FL 34229

  Happy Haven, a professionally managed, well-maintained manufactured home community, currently has a 370 sq. ft. home with 1 bedrooms and 1 bathrooms for sale. Take advantage of this offer now and live in one of the state's most attractive areas. Call and schedule a viewing of this home and ask about our current promotions!

  Tori Coil Happy Haven

  124 Happy Haven Dr Unit 5, Osprey, FL 34229
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  /80

  $695,000

  • 2 Beds
  • 2.5 Baths
  • 1,890 Sq Ft

  33 Bishops Court Rd Unit 118, Osprey, FL 34229

  Come and enjoy the perfect maintenance free lifestyle in this exquisite townhouse located in one of the finest countryclubs on the gulf coast, The Oaks Golf and Country Club. Previously redesigned, this tuscan style home in the quaintand charming Bishops Court in the Oaks Preserve features 2 large en suite bedrooms on the second floor, 2 1/2 baths, a spacious kitchen, and a great room

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  33 Bishops Court Rd Unit 118, Osprey, FL 34229
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  /85

  $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
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  /47

  $269,900

  • 2 Beds
  • 2 Baths
  • 1,325 Sq Ft

  232 Woodland Dr, Osprey, FL 34229

  This condo has the 3 L's! Location Location Location! Located in the central area of Osprey making it an easy drive to area beaches, downtown Venice or Sarasota. Located about a half mile to the Inter Coastal, making for a great walking area on Casey Key. Located close to the well known Casey Key Fish House and Tiki Bar. Shopping and restaurants are all nearby! The location of this condo within

  Pat Williams PAT WILLIAMS REALTY, LLC

  232 Woodland Dr, Osprey, FL 34229
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  /53

  $395,000

  • Land
  • 0.24 Acre
  • $1,645,833 per Acre

  51 N Tamiami Trail, Osprey, FL 34229

  Excellent location! Corner lot Zoned CG (Commercial General) with 117 feet of frontage on US 41 in Osprey, just north of Bay Street. Prime area of growth in Sarasota County next to Calico Corners, Bay St., Spanish Point restaurants, Sarasota crew and Super Walmart. Perfect opportunity for your own business or investment. Great accessibility on 3 sides for ingress and egress (US 41, Shumard, and

  Betsy De Manio COLDWELL BANKER REALTY

  51 N Tamiami Trail, Osprey, FL 34229
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  /45

  $615,000

  • 3 Beds
  • 2 Baths
  • 2,007 Sq Ft

  9528 Hawksmoor Ln, Sarasota, FL 34238

  Welcome to 9528 Hawksmoor Lane, located in the highly sought-after gated community of Stoneybrook Estates on Palmer Ranch. This spacious home features over 2,000 sq. ft. of living space, a two-car garage, and a crystal-clear pool recently resurfaced. It is loaded with curb appeal, from the pavered driveway to the pavered pool deck. As you enter the home, you are greeted with a serene view of the

  Victoria Reilly BERKSHIRE HATHAWAY HOMESERVICE

  9528 Hawksmoor Ln, Sarasota, FL 34238

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