Osprey, FL Homes

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  $244,907 Pending

  • 1 Bed
  • 1.5 Baths
  • 865 Sq Ft

  139 Woodland Place, Osprey, FL 34229

  Under contract-accepting backup offers. Here’s a polished real estate listing you can use: --- **Stunning Fully Remodeled 1-Bed / 2-Bath Ground-Floor Condo with Designer Finishes + $15,000 Custom Golf Cart Included** Step into luxury and comfort in this beautifully remodeled ground-floor condo, professionally designed from top to bottom. Every detail has been thoughtfully crafted to create a

  

  Jack Gang

  GANGWAY REALTY

  (941) 389-1870

  139 Woodland Place, Osprey, FL 34229
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• 

  

  

  /49

  $2,995 per month

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Condo for Rent

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229

  Great location - short drive to the best Florida beaches, golf clubs, Oscar Schrer State park, Legacy trail, right between cultural and culinary wealth of downtown Sarasota and Venice. Walking distance to Pine View School, playground and dog park across the street. Gated community with heated pool, fitness center and club house, newer buildings with hurricane -withstand features. One car garage

  127 Explorer Dr Unit 127 Explorer Dr, Osprey, FL 34229
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  $650,000 Sold Jul 03, 2025

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 13% Below List Price
  • $310/SF
  • 246 Days On Market

  Current Estimated Value $661,874

  Last Listing Agent Linda Scheller COLDWELL BANKER REALTY

  236 Hidden Bay Dr Unit 301, Osprey, FL 34229
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  /53

  Est $589,246 Not Listed For Sale

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

  4421 Conchfish Ln, Osprey, FL 34229

  4421 Conchfish Ln, Osprey, FL 34229
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  /55

  $699,000

  • 4 Beds
  • 3 Baths
  • 2,540 Sq Ft

  146 Willow Bend Way, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to 146 Willow Bend Way, a custom-built residence by Vision Homes in the sought-after community of Park Trace Estates. Nestled on a large lot with a pod view, this residence combines generous living spaces with a split floor plan suited for both family and guests. Featuring four bedrooms, three full baths, a den with French doors and tree car

  

  Maria Rocha

  KELLER WILLIAMS ON THE WATER S

  (941) 206-2984

  146 Willow Bend Way, Osprey, FL 34229
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  /31

  $4,500 per month

  • 3 Beds
  • 2 Baths
  • 2,367 Sq Ft
  • House for Rent

  1355 Southbay Dr, Osprey, FL 34229

  Southbay Yacht & Racquet Club where the true Florida lifestyle is alive and well! This three-bedroom two bath pool home is located in an active community with unmatched amenities such as an active social atmosphere, heated community pool, playground, fitness room, tennis, pickleball courts, and fishing. All for you to enjoy! Walk, bike or take your golf cart to restaurants, shopping or the

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  1355 Southbay Dr, Osprey, FL 34229
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  /2

  $780,000 Sold May 08, 2025

  779 Fordingbridge Way, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,154 Sq Ft
  • Built 2002

  Last Sold Summary

  • 1% Below List Price
  • $362/SF
  • 6 Days On Market

  Current Estimated Value $758,660

  Last Listing Agent Leonard Giarrano RE/MAX ALLIANCE GROUP

  779 Fordingbridge Way, Osprey, FL 34229
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  /78

  Est $541,794 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,678 Sq Ft

  36 Bishops Court Rd Unit 111, Osprey, FL 34229

  36 Bishops Court Rd Unit 111, Osprey, FL 34229
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  $884,000

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

  6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229

  Enjoy sweeping Intercoastal water views with peek-a-boo Gulf glimpses from this beautifully upgraded top-floor, end-unit residence filled with natural light, privacy, and coastal elegance. The interior features Luxury vinyl plank flooring, plantation shutters, crown molding, and higher ceilings unique to the top floor. The chef’s kitchen offers Bosch and JennAir appliances, a Liebherr split

  

  Andrea Stultz

  ENGEL + VOELKERS SARASOTA

  (941) 883-9484

  6100 Jessie Harbor Dr Unit 603, Osprey, FL 34229
• 

  

  /31

  $2,195 per month

  • 3 Beds
  • 2 Baths
  • 1,334 Sq Ft
  • Townhouse for Rent

  1755 Highland Rd, Osprey, FL 34229

  Spacious duplex in Osprey with a bonus room! This Townhouse boasts 2 bedrooms and a bonus room downstairs that can be used as an office, playroom or even additional bedroom. The unit features a single car garage, washer and dryer hook ups, a screened in patio out front, an oversized living room. This community is located off us highway 41 south, right across the street from beautiful Oscar

  Jennifer . STOCKTON REALTY ADVISORS LLC

  1755 Highland Rd, Osprey, FL 34229
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  /2

  $3,335,000 Sold Feb 12, 2025

  419 Yacht Harbor Dr, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,417 Sq Ft
  • Built 1978

  Last Sold Summary

  • 3% Above List Price
  • $1,380/SF
  • 7 Days On Market

  Current Estimated Value $3,169,171

  Last Listing Agent Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  419 Yacht Harbor Dr, Osprey, FL 34229
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  /15

  Est $790,728 Not Listed For Sale

  148 Osprey Point Dr, Osprey, FL 34229

  148 Osprey Point Dr, Osprey, FL 34229
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  /72

  $2,250,000

  • 4 Beds
  • 3.5 Baths
  • 4,012 Sq Ft

  433 E MacEwen Dr, Osprey, FL 34229

  An exceptionally well maintained 4,012sf residence with 4 bedrooms 3 full and a half baths situated on the interior Heron golf course on a 0.61 acre lot in the private Oaks Club community. It has golf course and water views and 24 hr gated security. This custom golf course home was built by esteemed builder Arthur Rutenberg. It represents Rutenberg at his very best - stylish elegance, superior

  Mark Lyda GENEROUS PROPERTY

  433 E MacEwen Dr, Osprey, FL 34229
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  /80

  $3,950 per month

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft
  • House for Rent

  523 Habitat Blvd, Osprey, FL 34229

  PRICE REDUCED!! Ready for you to move in! Immaculate home available as an annual rental, this pristine 4-bedroom, 3-bath residence is located in Willowbend, a sought-after, Lee Wetherington–built community known for quality construction and manicured surroundings. Ideally situated with convenient access to Sarasota, Venice, and the area’s renowned beaches, the home offers tranquil lake views from

  Susan Brooks COLDWELL BANKER SUNSTAR REALTY

  523 Habitat Blvd, Osprey, FL 34229
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  /2

  $1,050,000 Sold Jul 22, 2025

  142 Dory Ln, Osprey, FL 34229

  • 3 Beds
  • 2 Baths
  • 2,531 Sq Ft
  • Built 1984

  Last Sold Summary

  • 12% Below List Price
  • $415/SF
  • 32 Days On Market

  Current Estimated Value $1,032,300

  Last Listing Agent Sharon Lewis GOLF & BAY PROPERTIES LLC

  142 Dory Ln, Osprey, FL 34229
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  Est $1,160,996 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,416 Sq Ft

  3932 Waypoint Ave, Osprey, FL 34229

  3932 Waypoint Ave, Osprey, FL 34229
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  $2,495,000

  • 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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  /27

  $1,950 per month

  • 2 Beds
  • 2 Baths
  • 1,184 Sq Ft
  • Condo for Rent

  758 Pine Run Dr Unit 758, Osprey, FL 34229

  Welcome to your beautifully updated coastal retreat! This spacious 2-story condo offers 2 bedrooms, 2.5 bathrooms, and a fresh modern design throughout. Perfectly situated in a desirable community just minutes from the beach and with easy access to Blackburn Point Road, this home combines style, comfort, and convenience. Step inside to find a newly remodeled kitchen featuring shaker-style

  Jaime Barcelo GULF COAST REALTY & MANAGEMENT

  758 Pine Run Dr Unit 758, Osprey, FL 34229
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  /2

  $2,100,000 Sold Jan 30, 2026

  889 MacEwen Dr, Osprey, FL 34229

  • 4 Beds
  • 4 Baths
  • 3,235 Sq Ft
  • Built 1994

  Last Sold Summary

  • 9% Below List Price
  • $649/SF
  • 41 Days On Market

  Last Listing Agent Mark Lyda GENEROUS PROPERTY

  889 MacEwen Dr, Osprey, FL 34229
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  /67

  Est $573,287 Not Listed For Sale

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

  52 Bishops Court Rd Unit 113, Osprey, FL 34229

  52 Bishops Court Rd Unit 113, Osprey, FL 34229
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  $1,995,000

  • 3 Beds
  • 3 Baths
  • 3,029 Sq Ft

  401 N Point Rd Unit 1001, Osprey, FL 34229

  **Rarely available 10th-floor penthouse corner residence offering 3,029 square feet with sweeping Gulf and Bay views.** Ideally situated behind the secure gates of the highly sought-after Preserve neighborhood within The Oaks Country Club, this exceptional condo features 3 Bedrooms plus Den, 3 Full Baths, Private 2-Car Garage, and climate-controlled storage. The open-concept floor plan is

  Mark Lyda GENEROUS PROPERTY

  401 N Point Rd Unit 1001, Osprey, FL 34229
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  /15

  $3,500 per month

  • 3 Beds
  • 2 Baths
  • 1,648 Sq Ft
  • House for Rent

  2068 Preymore St, Osprey, FL 34229

  Welcome home to this charming and beautifully maintained 3-bedroom, 2-bath residence located on a great community. Step inside to a spacious open floor plan featuring a generous great room, a dedicated dining area, and a large primary suite. Cathedral ceilings, pocket sliding doors, and fluid room transitions create an airy atmosphere perfect for easy living and entertaining. The bright, eat-in

  Kenia Nunez PREFERRED SHORE LLC

  2068 Preymore St, Osprey, FL 34229
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  /2

  $1,405,000 Sold Jul 11, 2025

  282 Shell Midden Ct, Osprey, FL 34229

  • 3 Beds
  • 4.5 Baths
  • 3,699 Sq Ft
  • Built 1992

  Last Sold Summary

  • 17% Below List Price
  • $380/SF
  • 128 Days On Market

  Current Estimated Value $1,470,125

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  282 Shell Midden Ct, Osprey, FL 34229
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  /2

  Est $294,440 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 623 Sq Ft

  51 MacEwen Dr Unit 20, Osprey, FL 34229

  51 MacEwen Dr Unit 20, Osprey, FL 34229
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  /73

  $2,850,000

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

  662 Fernwalk Ln, Osprey, FL 34229

  **EXCEPTIONAL, FULLY RENOVATED, COUNTRY CLUB ESTATE HOME OFFERING TRANQUIL LAKE AND GARDEN VIEWS** ideally positioned on a serene interior cul-de-sac lot in Flood Zone X (no flood insurance required). Located behind the secure gates of the highly sought-after Bayside neighborhood within The Oaks Country Club, just steps from Little Sarasota Bay. This expansive residence features 4 Bedrooms and 4

  Mark Lyda GENEROUS PROPERTY

  662 Fernwalk Ln, Osprey, FL 34229
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  $4,250 per month

  • 3 Beds
  • 2 Baths
  • 2,188 Sq Ft
  • House for Rent

  1308 Thornapple Dr, Osprey, FL 34229

  Welcome home to Willow Bend, a tropical maintenance-free community located in middle of everything southwest Florida has to offer! Gorgeous turnkey 3 bedroom& 2 Bath Furnished annual rental near Nokomis Beach. Peaceful Lake views on an oversized lot. The pretty lanai features travertine marble tile and a HEATED POOL. Many upgrades include quartz kitchen counters, wood plank oak flooring, and

  Rachel Tritschler RE/MAX ALLIANCE GROUP

  1308 Thornapple Dr, Osprey, FL 34229
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  /2

  $1,330,000 Sold Jan 07, 2026

  401 N Point Rd Unit 901, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,594 Sq Ft
  • Built 2003

  Last Sold Summary

  • 24% Below List Price
  • $513/SF
  • 764 Days On Market

  Last Listing Agent Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 901, Osprey, FL 34229
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  /2

  Est $230,577 Not Listed For Sale

  • 1 Bed
  • 1 Bath
  • 595 Sq Ft

  51 MacEwen Dr Unit 13, Osprey, FL 34229

  51 MacEwen Dr Unit 13, 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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  /39

  $2,950 per month

  • 3 Beds
  • 2 Baths
  • House for Rent

  4429 Conchfish Ln, Osprey, FL 34229

  Steps from Pine View School, Florida's #1 public school, with 2,008 sq. ft. of living space, this home features brand-new thick waterproof laminate wood flooring in all bedrooms and closets, an ocean-inspired guest bathroom, and tile throughout the main living areas for easy maintenance.Enjoy the covered lanai overlooking a private backyard, perfect for relaxing or entertaining, and take

  JIA SONG Jia Song Realty

  4429 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $962,500 Sold Aug 07, 2025

  742 Shadow Bay Way, Osprey, FL 34229

  • 4 Beds
  • 3 Baths
  • 3,321 Sq Ft
  • Built 2002

  Last Sold Summary

  • 12% Below List Price
  • $290/SF
  • 115 Days On Market

  Current Estimated Value $946,312

  Last Listing Agent Reeny Kaney RE/MAX ALLIANCE GROUP

  742 Shadow Bay Way, Osprey, FL 34229
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  /2

  Est $92,871 Not Listed For Sale

  • Studio

  570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229

  570 Blackburn Point Rd Unit Siesta 40, Osprey, FL 34229
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  /49

  $1,175,000 Pending

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

  219 Keel Way, Osprey, FL 34229

  Under contract-accepting backup offers. **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,

  Mark Lyda GENEROUS PROPERTY

  219 Keel Way, Osprey, FL 34229
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  /36

  $2,500 per month

  • 2 Beds
  • 2 Baths
  • 1,069 Sq Ft
  • House for Rent

  305 Bay Vista Ave, Osprey, FL 34229

  Welcome to this stunning two-bedroom, two-bathroom retreat, perfectly designed for relaxation and entertainment!As you step inside, you'll notice the bright and airy open-plan living area, flooded with natural light pouring in through the large windows.But the true showstopper is the incredible backyard oasis! The expansive fenced yard beckons you to unwind and enjoy the fresh

  Jennifer . STOCKTON REALTY ADVISORS LLC

  305 Bay Vista Ave, Osprey, FL 34229
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  /2

  $210,000 Sold Oct 22, 2025

  480 Blackburn Point Rd Unit 4, Osprey, FL 34229

  • Built 2006

  Last Sold Summary

  • 7% Below List Price
  • 5 Days On Market

  Current Estimated Value $210,483

  Last Listing Agent Daniel Treiman MICHAEL SAUNDERS & COMPANY

  480 Blackburn Point Rd Unit 4, Osprey, FL 34229
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  /2

  Est $287,160 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,135 Sq Ft

  153 Navigation Cir Unit 106, Osprey, FL 34229

  153 Navigation Cir Unit 106, Osprey, FL 34229
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  $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
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  /38

  $6,000 per month

  • 3 Beds
  • 3 Baths
  • 2,055 Sq Ft
  • Condo for Rent

  409 N Point Rd Unit 802, Osprey, FL 34229

  **TURNKEY FURNISHED, PENTHOUSE Condo Unit has been FULLY RENOVATED** This 8TH FLOOR, Light and Bright, 3-BEDROOM plus 3 FULL BATH dwelling with screened balcony is available beginning in September, 2025. The 2055sf floorplan is tastefully furnished and offers superb views of the Intracoastal Waterway and Gulf. This unit was fully renovated in 2023 with updated oak hardwood flooring, new kitchen

  Mark Lyda GENEROUS PROPERTY

  409 N Point Rd Unit 802, Osprey, FL 34229
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  /2

  $980,000 Sold Dec 09, 2025

  385 N Point Rd Unit 903, Osprey, FL 34229

  • 3 Beds
  • 3 Baths
  • 2,778 Sq Ft
  • Built 2000

  Last Sold Summary

  • 11% Below List Price
  • $353/SF
  • 41 Days On Market

  Last Listing Agent Ryan Ackerman COLDWELL BANKER REALTY

  385 N Point Rd Unit 903, Osprey, FL 34229
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  /2

  Est $387,091 Not Listed For Sale

  • 2 Beds

  19 Westview Dr, Osprey, FL 34229

  19 Westview Dr, Osprey, FL 34229

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