Osprey, FL Homes

• 

  

  

  /13

  Est $1,234,961 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3603 N Point Rd Unit 603, Osprey, FL 34229

  3603 N Point Rd Unit 603, Osprey, FL 34229
• 

  

  

  /30

  $1,800,000

  • Land
  • 11.68 Acres
  • $154,110 per Acre

  500 Shotgun Ln, Osprey, FL 34229

  Truly a rare piece of Florida, a Natural Beauty! More than 11 acres in the heart of it all, west of I-75; Vacant land this size in Osprey’s sought-after Pine Ranch area is now very rare and seldom comes on the market.Discover an incredible opportunity to own 11.69 acres of vacant land in a highly desirable and rapidly growing area! Whether you're an investor, developer, looking to build your

  Ruediger Weiss CHARITY & WEISS INTERNATIONAL LLC

  500 Shotgun Ln, Osprey, FL 34229
• 

  

  /2

  $340,000 Sold May 08, 2025

  • 1,568 Sq Ft
  • $217/SF
  • 166 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2001

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229

  First-floor end-unit with hurricane-rated windows and lots of natural light, in the gated community of Hidden Bay that sits on the shores of Little Sarasota Bay. This unit includes a one-car garage, a screened lanai, two spacious bedrooms, two full baths, and a separate office and den. You'll find high ceilings, new luxury vinyl flooring throughout most of the unit, new air-conditioning system, a

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  294 Hidden Bay Dr Unit 103, Osprey, FL 34229
• 

  

  

  /50

  Est $821,639 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 2,680 Sq Ft

  3603 N Point Rd Unit 501, Osprey, FL 34229

  3603 N Point Rd Unit 501, Osprey, FL 34229
• 

  

  

  /7

  $6,600

  • 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
• 

  /2

  $1,600,000 Sold May 01, 2025

  • 5,987 Sq Ft
  • $267/SF
  • 1 Day On Market

  • 5 Beds
  • 7.5 Baths
  • Built 1991

  916 MacEwen Dr, Osprey, FL 34229

  Situated on a double lot behind the secure gates of The Oaks, this two story 5 bedroom home, with 7.5 bathrooms, boasts fantastic potential and excellent bones. The only thing it needs is for you to put your personal touch on it and make it your own. As you pull up to this home, using the front circular driveway, or the back driveway with access to the 4 CAR GARAGE, you will immediately be taken

  Steve Abbe COLDWELL BANKER REALTY

  916 MacEwen Dr, Osprey, FL 34229
• 

  

  /25

  Est $548,574 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,981 Sq Ft

  543 Meadow Sweet Cir, Osprey, FL 34229

  543 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /4

  $3,300

  • 1 Bed
  • 1 Bath

  124 Happy Haven Dr Unit 10, 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 10, Osprey, FL 34229
• 

  /2

  $875,000 Sold May 01, 2025

  • 2,329 Sq Ft
  • $376/SF
  • 8 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  851 E Bay St, Osprey, FL 34229

  **BEAUTIFULLY RENOVATED, PRIVATE OASIS AWAITS on this OVERSIZED 1.37 ACRE ESTATE with NO HOA** This GREEN BUILT (insulated concrete form constructed), Move-In Ready Residence offers 3-BEDS and 2-FULL BATHS, while Recent UPDATES include beautiful Flooring, Impressive Primary Bedroom Suite with walk-in closet and Stunning Primary Bath featuring dual vanities, custom-tiled shower and soaking tub, a

  Mark Lyda GENEROUS PROPERTY

  851 E Bay St, Osprey, FL 34229
• 

  /2

  Est $969,807 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,258 Sq Ft

  127 Turquoise Ln, Osprey, FL 34229

  127 Turquoise Ln, Osprey, FL 34229
• 

  

  /37

  $559,000

  • 2 Beds
  • 2 Baths
  • 1,229 Sq Ft

  455 N Shore Dr, Osprey, FL 34229

  Live the quintessential Florida lifestyle at 455 N Shore Drive in Osprey! Located West of the Trail in desirable Sorrento Shores, this beautifully updated 2-bedroom, 2-bath home is perfect for entertaining, relaxing, or as a strong rental investment.Just minutes from Nokomis Beach, Venice Beach, and Siesta Key, residents can also join the Sorrento Shores Marina Association, offering 42

  Geoff Scalera AUM FLORIDA REAL ESTATE LLC

  455 N Shore Dr, Osprey, FL 34229
• 

  /2

  $395,000 Sold Apr 30, 2025

  • 1,767 Sq Ft
  • $224/SF
  • 81 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1960

  418 Sarabay Rd, Osprey, FL 34229

  One or more photo(s) has been virtually staged. NEW PRICE IMPROVEMENT! Welcome to 418 Sarabay Rd, a lovely old-Florida home "West of Trail" in the charming community of Osprey, exuding a small-town feel, but just minutes away from all the conveniences and excitement of Sarasota and Venice! You and your guests will be drawn to spend lots of time in this fully fenced private oasis with its large

  Tracey Fiedler DALTON WADE INC

  418 Sarabay Rd, Osprey, FL 34229
• 

  

  /64

  Est $265,510 Not Listed For Sale

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

  224 Woodland Dr, Osprey, FL 34229

  224 Woodland Dr, Osprey, FL 34229
• 

  

  /51

  $6,490,000

  • 4 Beds
  • 5.5 Baths
  • 5,397 Sq Ft

  144 N Casey Key Rd, Osprey, FL 34229

  A striking coastal retreat on over half an acre along Little Sarasota Bay, this timeless residence blends architectural elegance with waterfront living. Offering private access to the Intracoastal with a 100-foot dock (built in 2019), dual 12,000-pound lifts, water, and electric, this property is an ideal destination for boating enthusiasts. Offered fully furnished upon request. The front

  Joel Schemmel DOUGLAS ELLIMAN

  144 N Casey Key Rd, Osprey, FL 34229
• 

  /2

  $318,000 Sold Apr 30, 2025

  • 1,411 Sq Ft
  • $225/SF
  • 125 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1972

  115 Villa Dr Unit 115, Osprey, FL 34229

  Welcome to your future waterfront retreat in the heart of Osprey, where coastal living meets convenience. This beautifully appointed villa offers 1,411 square feet of thoughtfully designed living space, featuring two bedrooms and two bathrooms in a flowing, open-concept layout.The primary bedroom suite provides a peaceful sanctuary with an ensuite bathroom and generous closet space. Throughout

  EJ Stukenborg KELLER WILLIAMS ON THE WATER S

  115 Villa Dr Unit 115, Osprey, FL 34229
• 

  

  /59

  Est $949,234 Not Listed For Sale

  • 3 Beds
  • 3 Baths
  • 3,811 Sq Ft

  384 S Creek Ct, Osprey, FL 34229

  384 S Creek Ct, Osprey, FL 34229
• 

  

  /43

  $620,000

  • 3 Beds
  • 2 Baths
  • 2,298 Sq Ft

  556 Crane Prairie Way, Osprey, FL 34229

  Welcome to a beautiful residence where comfort, privacy, and functionality come together seamlessly. A paver driveway, tile roof, mature landscaping, and a charming paver walkway set the tone as you arrive, leading to an inviting French door entry framed by a transom window. Inside, tile floors stretch through the main living areas, beginning with a light-filled foyer adorned with a chandelier.

  Joel Schemmel DOUGLAS ELLIMAN

  556 Crane Prairie Way, Osprey, FL 34229
• 

  /2

  $950,000 Sold Apr 29, 2025

  • 2,570 Sq Ft
  • $370/SF
  • 82 Days On Market

  • 3 Beds
  • 3.5 Baths
  • Built 1993

  32 Bayhead Ln, Osprey, FL 34229

  Divine is in the details of this lovely 3 bedroom, 3 bath professionally redesigned home in the Oaks Preserve. No need to be concerned with remodeling, as this home underwent a complete renovation in 2023. This exceptional property meets the demands of today’s discriminating buyer, with a spacious chef’s gourmet kitchen featuring top of the line stainless appliances, a large prep island, quartz

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  32 Bayhead Ln, Osprey, FL 34229
• 

  

  /99

  Est $701,706 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,330 Sq Ft

  801 Oak Briar Ln, Osprey, FL 34229

  801 Oak Briar Ln, Osprey, FL 34229
• 

  

  /49

  $574,700

  • 2 Beds
  • 2 Baths
  • 1,875 Sq Ft

  827 Placid Lake Dr, Osprey, FL 34229

  $15,000 SELLER CONTRIBUTION! With a full price offer, you can use this money for a mortgage rate reduction or your costs. Touch-ups are in process so if you hurry, you may have time to make requests that make it perfect for you!Rare opportunity to own one of the least expensive maintenance-free homes in a top-tier area and a renown, upscale community. Beautiful and quiet, yet

  Stephen Hachey FLAT FEE MLS REALTY

  827 Placid Lake Dr, Osprey, FL 34229
• 

  /2

  $165,000 Sold Apr 28, 2025

  • 1,223 Sq Ft
  • $135/SF
  • 53 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  235 Woodland Dr Unit 235, Osprey, FL 34229

  Welcome to 235 Woodland Drive in sunny Osprey, FL—located between Sarasota and Venice so you can easily enjoy the beaches, shopping, arts and entertainment of both towns. This 1,223 square-foot home is all about easy living, featuring an open floor plan and soaring ceilings that let in tons of natural light. You’ll love the sun-drenched living and dining areas, with huge sliding doors that open

  Priscilla Adams COMPASS FLORIDA LLC

  235 Woodland Dr Unit 235, Osprey, FL 34229
• 

  

  /57

  Est $655,054 Not Listed For Sale

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

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229

  6100 Jessie Harbor Dr Unit 201, Osprey, FL 34229
• 

  

  /7

  $115,000

  570 Blackburn Point Rd Unit 13, Osprey, FL 34229

  Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! This rarely available slip can fit boats up to 9 ft in height and offers hassle-free storage in one of Sarasota County's most convenient locations. Keep your boat safe from Florida's unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing

  Daniel Treiman MICHAEL SAUNDERS & COMPANY

  570 Blackburn Point Rd Unit 13, Osprey, FL 34229
• 

  /2

  $179,000 Sold Apr 28, 2025

  • 1,119 Sq Ft
  • $160/SF
  • 57 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1979

  312 Tropic Dr, Osprey, FL 34229

  Welcome to your dream home in a vibrant 55+ community! This charming residence offers 2 spacious bedrooms and 2 full bathrooms, perfect for comfortable living. Enjoy the Florida lifestyle with two screened-in porches, ideal for relaxing or entertaining. The home features a convenient laundry room and ample storage space. Equipped with hurricane windows, this home provides peace of mind. The roof

  Michelle Ward COMPASS FLORIDA LLC

  312 Tropic Dr, Osprey, FL 34229
• 

  

  /96

  Est $1,071,671 Not Listed For Sale

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

  385 N Point Rd Unit 501, Osprey, FL 34229

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

  

  /50

  $230,000

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

  216 Woodland Dr Unit 216, Osprey, FL 34229

  New price makes this a fantastic buy! Looking for an active lifestyle community close to the Intercoastal? Pine Run is the perfect location! Conveniently located between Sarasota and Venice in Osprey, this community is within close proximity of the famed Casey Key Fish House and Tiki Bar, plus many other restaurants, shopping areas, public boat launch, park and so much more! The Legacy Trail

  Pat Williams PAT WILLIAMS REALTY, LLC

  216 Woodland Dr Unit 216, Osprey, FL 34229
• 

  /2

  $744,800 Sold Apr 24, 2025

  • 3,060 Sq Ft
  • $243/SF
  • 145 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 2002

  448 Park Trace Blvd, Osprey, FL 34229

  **MOTIVATED SELLERS – WILL OFFER CREDIT TOWARD A NEW ROOF WITH ACCEPTABLE OFFER!** Experience the ideal combination of elegance, comfort, and functionality in this custom-built pool home, thoughtfully crafted with premium upgrades and meticulously maintained over the years. Set on a spacious lot, this home boasts 4 bedrooms, 3 baths, a dedicated office, and an impressive array of features

  Toni Zarghami KW COASTAL LIVING III

  448 Park Trace Blvd, Osprey, FL 34229
• 

  

  /73

  Est $440,590 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229

  291 Hidden Bay Dr Unit 201, Osprey, FL 34229
• 

  

  /61

  $325,000

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

  116 Navigation Cir Unit 106, Osprey, FL 34229

  Location, Lifestyle, and Peace of Mind — All in One!Welcome home to this beautifully appointed 3-bedroom, 2-bath end-unit condo in one of the area's most desirable pet-friendly gated communities. Built with lasting quality in mind, this home offers solid block stucco construction paired with hurricane-impact windows and doors — giving you the comfort of security and the ease of low

  Pan Steele, GRI COLDWELL BANKER REALTY

  116 Navigation Cir Unit 106, Osprey, FL 34229
• 

  /2

  $315,000 Sold Apr 24, 2025

  • 1,092 Sq Ft
  • $288/SF
  • 147 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  214 Patterson Ave, Osprey, FL 34229

  Welcome to your dream home in the enchanting village of Osprey! This inviting 3-bedroom, 2-bathroom block home is nestled on a tranquil street, surrounded by lush landscaped gardens. Designed with comfort and functionality in mind, the open-plan living and dining area provides an ideal space for gatherings, with a clear view into the fully remodeled kitchen. Whether cooking or entertaining, the

  Lisa Bouck, PA RE/MAX ALLIANCE GROUP

  214 Patterson Ave, Osprey, FL 34229
• 

  

  /33

  Est $424,579 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,599 Sq Ft

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229

  293 Hidden Bay Dr Unit 201, Osprey, FL 34229
• 

  

  /37

  $199,000

  • 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

  John Alexander FINE PROPERTIES

  238 Palm Air Dr, Osprey, FL 34229
• 

  /2

  $880,000 Sold Apr 23, 2025

  • 2,045 Sq Ft
  • $430/SF
  • 61 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1978

  1237 Flying Bridge Ln, Osprey, FL 34229

  A Southbay Yacht & Racquet Club beauty! This home has been given meticulous care and offers an abundance of updates and upgrades. Popular Southbay community features a boating marina on the Inter coastal Waterway, making this one of the most sought after locations west of the trail! This airy and open floorplan is sure to please! There are so many delightful updates and improvements, I'll try to

  Pat Williams PAT WILLIAMS REALTY, LLC

  1237 Flying Bridge Ln, Osprey, FL 34229
• 

  

  /40

  Est $1,468,360 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,567 Sq Ft

  1787 S Creek Dr, Osprey, FL 34229

  1787 S Creek Dr, Osprey, FL 34229
• 

  

  /62

  $785,500 Open House 9/28

  • 4 Beds
  • 3 Baths
  • 2,314 Sq Ft

  523 Habitat Blvd, Osprey, FL 34229

  In the Lee Wetherington-built community of Willowbend is a stunning home. This enchanting residence borders a sparkling lake with curb appeal emphasized by lush landscaping and a paver-accented driveway. This quality-built home is the desirable Ashley II floor plan, with an oversized 23-by-19-foot garage. Every detail in this home is addressed with remarkable style including double-door entry,

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  523 Habitat Blvd, Osprey, FL 34229
• 

  /2

  $807,000 Sold Apr 22, 2025

  • 2,112 Sq Ft
  • $382/SF
  • 244 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1975

  124 Tina Island Dr, Osprey, FL 34229

  ***Amazing waterfront opportunity*** One of the lowest priced canal front properties between Sarasota and Venice*** This great waterfront location is in desirable Sorrento Shores with a new dock on a wide canal sitting on a large lot with great views This 3 bedroom 2 bath split plan has a large living/dining area and a separate office space. The kitchen area has a separate seating area with a

  Glenn Davis COLDWELL BANKER SARASOTA CENT.

  124 Tina Island Dr, Osprey, FL 34229
• 

  

  /68

  Est $961,876 Not Listed For Sale

  • 3 Beds
  • 4 Baths
  • 3,028 Sq Ft

  501 Velasquez Dr, Osprey, FL 34229

  501 Velasquez Dr, Osprey, FL 34229
• 

  

  /65

  $710,000 Open Sun 1PM - 4PM

  • 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!!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 community perfectly positioned between the charm

  Merryl Koven COLDWELL BANKER REALTY

  250 Hidden Bay Dr Unit A302, Osprey, FL 34229
• 

  /2

  $245,000 Sold Apr 21, 2025

  • 1,316 Sq Ft
  • $186/SF
  • 103 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1980

  225 Woodland Dr, Osprey, FL 34229

  This completely remodeled, GROUND LEVEL, 2/2 condo is available in a charming West of Trail community (but not in a flood zone) and is the hidden gem you've been looking for! Step inside and be captivated by artistic elegance. This home has been thoughtfully updated and features a new HVAC system in 2023, a kitchen remodel in 2023 including sleek new appliances (including an induction cooktop),

  Priscilla Adams COMPASS FLORIDA LLC

  225 Woodland Dr, Osprey, FL 34229
• 

  

  /40

  Est $516,689 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,788 Sq Ft

  510 Meadow Sweet Cir, Osprey, FL 34229

  510 Meadow Sweet Cir, Osprey, FL 34229

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