Osprey, FL Homes

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  /41

  $783,000 Sold Jun 04, 2024

  • 2,320 Sq Ft
  • $338/SF
  • 37 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2003

  675 Crane Prairie Way, Osprey, FL 34229

  The intelligent design is as striking as its beauty in this four-bedroom, three-bath residence built by Lee Wetherington Homes in the maintenance-free landscape community of Willowbend. An Ashley floor plan, with double door entry and numerous upgrades add to the timeless character of this special home. Wrap yourself in luxury in a modern home with clean lines, boasting tray ceilings, beautiful

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  675 Crane Prairie Way, Osprey, FL 34229
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  /60

  Est $735,621 Not Listed For Sale

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

  401 N Point Rd Unit 502, Osprey, FL 34229

  401 N Point Rd Unit 502, Osprey, FL 34229
• 

  

  

  /77

  $1,795,000 Pending

  • 4 Beds
  • 3.5 Baths
  • 3,572 Sq Ft

  269 Pine Ranch Trail, Osprey, FL 34229

  One or more photo(s) has been virtually staged. This magnificent modern manse, with 4 bedrooms and 3.5 baths, literally has everything you could dream of to make a home complete, ALL OF IT NEW! Located in Pine Ranch, a community of single family homes with 1-5 acres of land, you will not find a more stately, spacious home, completely updated and ready for you to live out your Florida dreams.

  Steve Abbe COLDWELL BANKER REALTY

  269 Pine Ranch Trail, Osprey, FL 34229
• 

  

  

  /27

  $1,590,000 Sold May 31, 2024

  • 3,665 Sq Ft
  • $434/SF
  • 0 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 1990

  935 Blue Heron Overlook, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Located behind the gates of The Oaks, on a quiet cul-de-sac, this 4 bedroom home with 2 full and 2 half baths, is situated on a lovely lot with Southern exposure. Enter through the front door and you will be welcomed to a great floor plan that is ideal for entertaining as well as the quiet enjoyment of those residing in this spacious home. The

  Steve Abbe COLDWELL BANKER REALTY

  935 Blue Heron Overlook, Osprey, FL 34229
• 

  

  

  /25

  Est $944,218 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,027 Sq Ft

  1113 Millpond Ct, Osprey, FL 34229

  1113 Millpond Ct, Osprey, FL 34229
• 

  

  /69

  $2,495,000 Pending

  • 3 Beds
  • 3.5 Baths
  • 3,586 Sq Ft

  230 Osprey Point Dr, Osprey, FL 34229

  Under contract-accepting backup offers. **IMMACULATE ESTATE -- NEWER CONSTRUCTION (2014) -- METICULOUSLY MAINTAINED, MOVE-IN READY, CUSTOM Residence Designed by LAS CASITAS Architects** offers exceptional quality craftsmanship throughout and is located behind the Secure Gates of THE OAKS-BAYSIDE Country Club community. Situated on an Oversized 0.59 Acre Lot backing to a Tranquil, Coastal

  Mark Lyda GENEROUS PROPERTY

  230 Osprey Point Dr, Osprey, FL 34229
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  /64

  $674,000 Sold May 31, 2024

  • 1,404 Sq Ft
  • $480/SF
  • 67 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1978

  128 Villa Dr Unit 128, Osprey, FL 34229

  Canal front home with no bridges to the intercostal and Gulf of Mexico! West of the trail in Osprey Florida. 3 miles to beautiful Nokomis Beach. Home is not attached. In your private backyard you have a brand new dock and new electric boat lift to keep your boat high and dry. Dock has water, electric, ambient lighting and snook lights in the water. This 2 bed/2 bath Villa/single family home has

  Raphael Carlisi KEYS TO THE BAY REAL ESTATE

  128 Villa Dr Unit 128, Osprey, FL 34229
• 

  

  /53

  Est $1,039,915 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,183 Sq Ft

  1064 Mallard Marsh Dr, Osprey, FL 34229

  1064 Mallard Marsh Dr, Osprey, FL 34229
• 

  

  /76

  $3,900,000

  • 4 Beds
  • 5.5 Baths
  • 8,635 Sq Ft

  112 Osprey Point Dr, Osprey, FL 34229

  **MULTIPLE OFFERS - HIGHEST AND BEST DUE NO LATER THAN 5 PM ON 05/11/2025**Premier Waterfront Opportunity in The Oaks BaysideThis grand estate home, perfectly positioned on a rarely available direct waterfront lot in the exclusive, gated Oaks Bayside community, offers sweeping views of Little Sarasota Bay and exceptional potential. With its expansive floor plan across three levels, soaring

  Kara Money KARA MONEY LLC

  112 Osprey Point Dr, Osprey, FL 34229
• 

  

  /35

  $899,000 Sold May 24, 2024

  • 3,332 Sq Ft
  • $270/SF
  • 102 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2004

  1069 Scherer Way, Osprey, FL 34229

  Price Improvement! Introducing an exquisite Rivendell residence nestled beside Oscar Scherer State Park, offering stunning views of the expansive lake just steps from your front door. Indulge in the seamless blend of indoor and outdoor living, with a generous lanai and a sparkling pool/spa, creating the perfect paradise retreat. Delight in the abundant wildlife, including majestic eagles, osprey,

  Richard Hehl COASTAL PROPERTIES GROUP

  1069 Scherer Way, Osprey, FL 34229
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  /69

  Est $723,991 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,069 Sq Ft

  188 Dory Ln, Osprey, FL 34229

  188 Dory Ln, Osprey, FL 34229
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  /48

  $250,000 Sold May 24, 2024

  • 1,325 Sq Ft
  • $189/SF
  • 176 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  124 Woodland Dr, Osprey, FL 34229

  This updated, clean, and ready to move in condo has a prime property location for your full-time or seasonal enjoyment. An end upstairs unit, nestled among the trees and surrounded by a backdrop of nature with the ability to enjoy the outdoors on three balconies is wonderfully unique! The unit features generous room sizes with plenty of light throughout, soft tones, high ceilings, NEW easy care

  Susan Elkins COMPASS FLORIDA LLC

  124 Woodland Dr, Osprey, FL 34229
• 

  

  /73

  Est $1,554,591 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,201 Sq Ft

  419 E MacEwen Dr, Osprey, FL 34229

  419 E MacEwen Dr, Osprey, FL 34229
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  /9

  $170,000 Sold May 22, 2024

  • 630 Sq Ft
  • $270/SF
  • 162 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1950

  242 Washington Ave, Osprey, FL 34229

  WONDERFUL LOCATION! LOTS OF NEW HOMES IN NEIGHBORHOOD. CLOSE TO PINEVIEW; BEACHES; MALL SHOPPING; WAL-MART. 2Bedroom 1 Bath home is perfect for 1st time home buyers or investors. NEW ROOF IN 2023!!

  Dan Miller PREFERRED SHORE LLC

  242 Washington Ave, Osprey, FL 34229
• 

  

  /67

  Est $917,727 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 2,491 Sq Ft

  236 Hidden Bay Dr Unit 601, Osprey, FL 34229

  236 Hidden Bay Dr Unit 601, Osprey, FL 34229
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  /70

  $1,150,000 Sold May 21, 2024

  • 2,346 Sq Ft
  • $490/SF
  • 213 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2018

  3961 Waypoint Ave, Osprey, FL 34229

  Escape to your coastal oasis nestled within the exclusive enclave of Bayside, where luxury living meets the tranquility of Little Sarasota Bay. This newly built 3-bedroom, 3-bathroom residence, boasting an additional den/office, is a testament to perfection with upgrades at every corner. As you enter, be captivated by the breathtaking view of the southeast-facing preserve area, alive with the

  Lee Brewer RE/MAX ALLIANCE GROUP

  3961 Waypoint Ave, Osprey, FL 34229
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  /37

  Est $911,275 Not Listed For Sale

  • 4 Beds
  • 2 Baths
  • 2,917 Sq Ft

  77 Bayhead Ln, Osprey, FL 34229

  77 Bayhead Ln, Osprey, FL 34229
• 

  

  /65

  $950,000 Sold May 16, 2024

  • 2,632 Sq Ft
  • $361/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  800 Eaglenook Way, Osprey, FL 34229

  Welcome to Pine Ranch, where quiet tree lined streets of majestic laurel oaks guide you to the natural setting of this home situated on 2.4 acres. This one-of-a-kind estate offers 3 bedrooms, 2 bathrooms, and an attached 2-car garage. What sets this home apart, is a detached air-conditioned garage that has been converted into a private sanctuary. This space is ideal for creating a large game

  Ashley Wallace MAVREALTY

  800 Eaglenook Way, Osprey, FL 34229
• 

  

  /18

  Est $457,076 Not Listed For Sale

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

  121 Burney Rd, Osprey, FL 34229

  121 Burney Rd, Osprey, FL 34229
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  /2

  $2,100,000 Sold May 15, 2024

  • 4,495 Sq Ft
  • $467/SF
  • 15 Days On Market

  • 4 Beds
  • 4 Baths
  • Built 2008

  580 N MacEwen Dr, Osprey, FL 34229

  **EXCEPTIONAL and METICULOUSLY MAINTAINED, CUSTOM GOLF COURSE ESTATE built by JOHN CANNON in 2008** is situated on an Over Half Acre, Private and Serene Lot with Golf Course and Water Views in THE OAKS COUNTRY CLUB Community. NEW ROOF (2021), GENERATOR (with 1000 Gallon Propane Tank) and HURRICANE IMPACT WINDOWS & DOORS. From its Stunning Curb Appeal to its Tastefully Appointed Interior, this

  Mark Lyda GENEROUS PROPERTY

  580 N MacEwen Dr, Osprey, FL 34229
• 

  

  /71

  Est $303,001 Not Listed For Sale

  • 2 Beds
  • 2.5 Baths
  • 1,305 Sq Ft

  752 Pine Run Dr, Osprey, FL 34229

  752 Pine Run Dr, Osprey, FL 34229
• 

  

  /55

  $638,000 Sold May 15, 2024

  • 2,143 Sq Ft
  • $298/SF
  • 363 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2004

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229

  Seller financing up to $425,000 available with minor qualifications. Begin each day with panoramic water views of Blackburn Bay from the kitchen, living room and master bedroom suite. Enjoy strolling through the lush landscaped walkways throughout the community that lead you to the community pool, fitness center, clubhouse, tennis courts, pickleball, shuffle board, kayak launch, and boat dock.

  Steve Abbe COLDWELL BANKER REALTY

  5100 Jessie Harbor Dr Unit 602, Osprey, FL 34229
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  /45

  Est $606,850 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,369 Sq Ft

  540 Meadow Sweet Cir, Osprey, FL 34229

  540 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /96

  $1,200,000 Sold May 10, 2024

  • 2,594 Sq Ft
  • $463/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2000

  385 N Point Rd Unit 501, Osprey, FL 34229

  You will find UNPARALLELED LUXURY AND QUALITY IN THIS 3 BEDROOM (plus DEN), 3 BATH RESIDENCE THAT HAS BEEN UPDATED TO THE NINES! Every inch reflects the care taken selecting the best of everything for this home! The moment you step into this unit from your private elevator you will know that it is without equal. The great room has an incredible built-in bar, with a wine cooler with separate

  Steve Abbe COLDWELL BANKER REALTY

  385 N Point Rd Unit 501, Osprey, FL 34229
• 

  

  /25

  Est $361,584 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,395 Sq Ft

  111 Villa Dr, Osprey, FL 34229

  111 Villa Dr, Osprey, FL 34229
• 

  /2

  $1,400,000 Sold May 07, 2025

  • 3,094 Sq Ft
  • $452/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1997

  378 MacEwen Dr, Osprey, FL 34229

  Beautiful lakefront 3 bedroom, 3 bath home in The Oaks Clubside with view of the Eagle 3. The Oaks, Sarasota’s premier golf and country club, has two championship golf courses, an outstanding tennis program, pickle ball and croquet courts, a junior Olympic community pool, state-of-the-art fitness center and offers a wide variety of dining, recreational and social options. Membership is required

  Steve Abbe COLDWELL BANKER REALTY

  378 MacEwen Dr, Osprey, FL 34229
• 

  

  /9

  Est $1,799,641 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 3,836 Sq Ft

  621 N MacEwen Dr, Osprey, FL 34229

  621 N MacEwen Dr, Osprey, FL 34229
• 

  /2

  $1,100,000 Sold Apr 23, 2025

  • 2,388 Sq Ft
  • $461/SF
  • 1 Day On Market

  • 3 Beds
  • 3 Baths
  • Built 2013

  229 Lookout Point Dr, Osprey, FL 34229

  This meticulously cared for John Cannon home is an exceptional opportunity to enjoy the desirable Southbay lifestyle in a newer 2013 built home. With raised, 10-foot tray ceilings, crown molding, millwork, plantation shutters, wood plank style tile floors, and a whole house Sonos sound system, this well-designed split floor plan includes 3 bedrooms (2 en-suite and a separate 3rd bath) and a study

  Valerie Dall'acqua PREMIER SOTHEBY'S INTERNATIONAL REALTY

  229 Lookout Point Dr, Osprey, FL 34229
• 

  

  /50

  Est $1,140,976 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,691 Sq Ft

  214 Four Knot Ln, Osprey, FL 34229

  214 Four Knot Ln, Osprey, FL 34229
• 

  /2

  $2,000,000 Sold Apr 21, 2025

  • 3,598 Sq Ft
  • $556/SF
  • 76 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1982

  1862 Island Way, Osprey, FL 34229

  South Sarasota waterfront property surrounded by 312-ft. of water on three sides feels like living on a private island. Serene privacy on a cul de sac in the secluded South Creek community directly across from Oscar Scherer State Park and just 5 minutes to Pine View School for the Gifted. Located between Sarasota and Venice with easy access to the best amenities in both communities including

  Nancy Endara PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1862 Island Way, Osprey, FL 34229
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  /50

  Est $486,692 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,274 Sq Ft

  120 Shoreland Dr, Osprey, FL 34229

  120 Shoreland Dr, Osprey, FL 34229
• 

  /2

  $896,148 Sold Apr 07, 2025

  • 2,166 Sq Ft
  • $414/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229

  Under Construction. Photos are for demonstration purposes only and may not reflect the actual unit or floor plan. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay, a gated, 12-acre resort-style community located on the water's edge of Little Sarasota Bay in Osprey, Florida. The final waterfront building of 16 units is now under construction,

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 301, Osprey, FL 34229
• 

  

  /52

  Est $852,568 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,498 Sq Ft

  352 Park Trace Blvd, Osprey, FL 34229

  352 Park Trace Blvd, Osprey, FL 34229
• 

  /2

  $795,000 Sold Mar 21, 2025

  • 2,166 Sq Ft
  • $367/SF
  • 0 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2023

  280 Hidden Bay Dr Unit 304, Osprey, FL 34229

  Pre-Construction. To be built. This unit is sold.

  Bob Morris SVN COMMERCIAL ADVISORY GROUP

  280 Hidden Bay Dr Unit 304, Osprey, FL 34229
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  /44

  Est $445,792 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,425 Sq Ft

  4101 Jessie Harbor Dr Unit 4101, Osprey, FL 34229

  4101 Jessie Harbor Dr Unit 4101, Osprey, FL 34229
• 

  /2

  $1,855,000 Sold Feb 26, 2025

  • 3,794 Sq Ft
  • $489/SF
  • 9 Days On Market

  • 4 Beds
  • 4.5 Baths
  • Built 1999

  533 N MacEwen Dr, Osprey, FL 34229

  **IMPRESSIVE ESTATE WITH GOLF COURSE AND WATER VIEW in the Highly Sought-After OAKS COUNTRY CLUB Community** situated on an over 2/3 Acre, Serene Lot with Ideal Southwestern-Exposure and View across the 15TH Fairway of the interior, HERON GOLF COURSE. Recent UPDATES include NEW ROOF (2020), NEW HURRICANE IMPACT WINDOWS & SLIDING DOORS (2020), Etc. With its delightful curb appeal and manicured

  Mark Lyda GENEROUS PROPERTY

  533 N MacEwen Dr, Osprey, FL 34229
• 

  

  /98

  Est $1,442,707 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,933 Sq Ft

  367 Renoir Dr, Osprey, FL 34229

  367 Renoir Dr, Osprey, FL 34229
• 

  /2

  $3,915,000 Sold Feb 26, 2025

  • 5,453 Sq Ft
  • $718/SF
  • 214 Days On Market

  • 4 Beds
  • 5.5 Baths
  • Built 1986

  601 Fernwalk Ln, Osprey, FL 34229

  **EXQUISITELY DESIGNED ESTATE BOASTS MODERN & CONTEMPORARY ELEGANCE** This FULLY UPDATED Residence features a MAIN HOUSE with 3Beds/4.5Baths plus GUEST HOUSE (1Bed/1Bath, Kitchen/Laundry, Living area) and is situated on an Oversized, Private and Serene DOUBLE LOT in the SECURE, OAKS BAYSIDE Country Club Neighborhood on Little Sarasota Bay. Finishes of the highest quality abound and include

  Mark Lyda GENEROUS PROPERTY

  601 Fernwalk Ln, Osprey, FL 34229
• 

  

  /49

  Est $613,084 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,165 Sq Ft

  568 Crane Prairie Way, Osprey, FL 34229

  568 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  $630,000 Sold Feb 03, 2025

  • 1,920 Sq Ft
  • $328/SF
  • 0 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1985

  480 Faith Ave, Osprey, FL 34229

  Looking for land between Sarasota and Venice and close to the beach? This is a completely private natural paradise. Come claim your 2 acre estate of buildable open use land with an additional half acre boundary of Florida wetland. Only 14 houses on this private road just a few miles south of Central Sarasota Parkway, approximately 10 miles from both Sarasota and Venice and just 5 miles to the

  Robin Leonardi MICHAEL SAUNDERS & COMPANY

  480 Faith Ave, Osprey, FL 34229

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