Homes in ZIP Code 34229

• 

  

  

  /27

  Est $381,850 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,581 Sq Ft

  4260 Expedition Way Unit 4260, Osprey, FL 34229

  4260 Expedition Way Unit 4260, Osprey, FL 34229
• 

  

  

  /100

  $1,295,000 Open Sat 2PM - 4PM

  • 4 Beds
  • 3.5 Baths
  • 3,479 Sq Ft

  1484 Seafarer Dr, Osprey, FL 34229

  Welcome to Southbay Yacht & Racquet Club, one of the Gulf Coast’s most coveted communities—where every day feels like a vacation! Southbay boasts a world-class private marina with 172 deep-water slips, accommodating yachts up to 55 feet, along with personal watercraft and kayaks. Slip rentals are available and offered at a highly competitive rate, making this an exceptional value for boating

  Seth Westerberg EXP REALTY LLC

  1484 Seafarer Dr, Osprey, FL 34229
• 

  

  

  /55

  $480,000 Sold May 14, 2025

  • 1,808 Sq Ft
  • $265/SF
  • 57 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2003

  564 Meadow Sweet Cir, Osprey, FL 34229

  Discover serenity and peace of mind in this idyllic property in the sought after Cottages of Rivendell. Close to breathtaking Casey Key, Siesta Key Beach, Nokomis Beach and the crystal blue waters of the Gulf of Mexico. This home offers an excellent location with convenient access to all modern amenities. Enjoy the luxury of being short distance to the nationally acclaimed Pine View School. The

  Kevin Stanley, P.A. PREMIER SOTHEBYS INTL REALTY

  564 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  

  /24

  Est $618,009 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,975 Sq Ft

  2001 Cordes St, Osprey, FL 34229

  2001 Cordes St, Osprey, FL 34229
• 

  

  

  /46

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 1,952 Sq Ft

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229

  Welcome to the exclusive Blackburn Point Marina Village – where luxury meets convenience in one of Sarasota's desirable waterfront communities! This rarely available, beautifully appointed townhome offers the best of maintenance-free, coastal living in a gated community featuring resort-style amenities including a heated pool, cabana, tiki bar, and more. Enjoy peace of mind with a new roof (2025)

  Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

  1164 Beachcomber Ct Unit 19, Osprey, FL 34229
• 

  /2

  $710,000 Sold May 09, 2025

  • 2,533 Sq Ft
  • $280/SF
  • 117 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2002

  710 Shadow Bay Way, Osprey, FL 34229

  Florida’s perfect floor plan! Built in 2002, this home features soaring ceilings, engineered hardwood maple floors that are softer and warmer underfoot than tile, and a thoughtfully designed layout for both living and entertaining. The great room, complete with a cozy wood-burning fireplace, flows seamlessly into a formal dining room, a spacious eat-in kitchen, and a versatile office. The serene

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  710 Shadow Bay Way, Osprey, FL 34229
• 

  

  /48

  Est $396,708 Not Listed For Sale

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

  123 Revolution Way Unit 101, Osprey, FL 34229

  123 Revolution Way Unit 101, Osprey, FL 34229
• 

  

  /38

  $959,000

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

  238 Lookout Point Dr, Osprey, FL 34229

  Nestled in the heart of Southbay Yacht & Racquet Club, this exquisitely renovated and impeccably maintained residence offers an enviable lifestyle for those who cherish the water. The journey begins at the inviting brick paver entry, guiding you into a gracious foyer that sets the tone for the home's elegant charm. Upon entering, you are welcomed by a spacious great room featuring new tile

  Stephanie Church COLDWELL BANKER REALTY

  238 Lookout Point Dr, Osprey, FL 34229
• 

  /2

  $780,000 Sold May 08, 2025

  • 2,154 Sq Ft
  • $362/SF
  • 6 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2002

  779 Fordingbridge Way, Osprey, FL 34229

  Discover the park like unhurried living of Rivendell, known for its tree lined streets, friendly neighbors. Residents enjoy 380 acres with 200 acres as preserves, lakes, open spaces, and trails. Fully remodeled one owner home meticulously maintained, new tile roof Jan 2025, impact glass windows all around, fully remodeled 2154 sqft in a great room design. All on a 0.46-acre private preserve view

  Leonard Giarrano RE/MAX ALLIANCE GROUP

  779 Fordingbridge Way, Osprey, FL 34229
• 

  

  /61

  Est $423,201 Not Listed For Sale

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

  4185 Frontier Ln Unit 102, Osprey, FL 34229

  4185 Frontier Ln Unit 102, Osprey, FL 34229
• 

  

  /45

  $950,000 Open Sun 1PM - 3PM

  • 3 Beds
  • 3 Baths
  • 2,283 Sq Ft

  172 Sea Anchor Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to your dream home! This 3-bedroom, 3-Bath residence offers the perfect blend of comfort, style, and outdoor living. Step inside to an open floorplan featuring a spacious living area, modern kitchen with stainless steel appliances. The separate den allows the perfect place to work from home! The highlight of this home is the inviting

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  172 Sea Anchor Dr, 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
• 

  

  /59

  Est $390,306 Not Listed For Sale

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

  99 Explorer Dr Unit 102, Osprey, FL 34229

  99 Explorer Dr Unit 102, Osprey, FL 34229
• 

  

  /37

  $625,000 Open Sun 2PM - 5PM

  • 2 Beds
  • 2 Baths
  • 1,932 Sq Ft

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229

  One of Sarasota’s Best-Kept Secrets! Top-Floor Bayfront Retreat in Hidden Bay. 2 Bed | 2 Bath + Den | Enclosed Lanai | 2-Car Garage | Offered Fully Furnished. Perched on the top floor of a premier building in the exclusive Hidden Bay gated community, this spacious and light-filled condo offers breathtaking, panoramic views of Sarasota Bay. A true diamond in the rough, this home is ready for your

  Joy McGraw REAL ESTATE REFINED

  242 Hidden Bay Dr Unit 603, Osprey, FL 34229
• 

  /2

  $140,000 Sold May 02, 2025

  • 1,173 Sq Ft
  • $119/SF
  • 9 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1979

  234 Patterson Ave, Osprey, FL 34229

  Welcome to 234 Patterson Ave, a charming single-family home nestled in the heart of Osprey, Florida. This home went through a small fire in the living room and the ceilings and some walls need drywalled back in and it needs a new electric box to go with the new wiring installed this month for $5000. This owner has updated some much on this home and with not a ton of repairs left for someone to

  Sean Seward KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  234 Patterson Ave, Osprey, FL 34229
• 

  

  /42

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 673 Sq Ft

  36 Siesta Cir W, Osprey, FL 34229

  36 Siesta Cir W, Osprey, FL 34229
• 

  

  /72

  $1,000,000

  • 4 Beds
  • 3 Baths
  • 3,011 Sq Ft

  1085 Mallard Marsh Dr, Osprey, FL 34229

  Step into this beautifully renovated Rivendell home and discover a stunning pool and lanai area, thoughtfullydesigned for relaxation and enjoyment. Offering expansive lake views, this home provides a serene retreat in one ofthe area's most sought-after communities.Spanning over 3,000 square feet, this spacious residence features four bedrooms, three baths, and an upstairs

  Veronica Manes MICHAEL SAUNDERS & COMPANY

  1085 Mallard Marsh Dr, 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
• 

  

  /4

  Est $30,152 Not Listed For Sale

  • Studio
  • 45,244 Sq Ft

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229

  570 Blackburn Point Rd Unit 28, Osprey, FL 34229
• 

  

  /80

  $1,195,000

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

  3921 Waypoint Ave, Osprey, FL 34229

  CASUAL, COASTAL ELEGANCE in this charming WATERFRONT community – BAYSIDE on LITTLE SARASOTA BAY! The Florida Lifestyle you’ve always dreamt of awaits you at Bayside on Little Sarasota Bay – a GATED ENCLAVE OF JUST 49 HOMES tucked away on the bay in Osprey Florida - one of our area’s best kept secrets ideally located between Sarasota & Venice! This delightful POOL HOME offers 3 BEDROOMS, 3 FULL

  Julie Larson WHITE SANDS REALTY GROUP FL

  3921 Waypoint Ave, 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
• 

  

  /68

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,247 Sq Ft

  273 Sun Air Cir, Osprey, FL 34229

  273 Sun Air Cir, Osprey, FL 34229
• 

  

  /67

  $1,045,000

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

  227 Saint James Park, Osprey, FL 34229

  **TURNKEY FURNISHED, ELEGANT and TRADITIONAL ESTATE by Famed Architect, Bo MacEwen, on the Single Largest 0.32 Acre Cul De Sac Lot in the Popular SAINT JAMES PARK neighborhood in The Oaks Country Club. NEW ROOF (2024), HURRICANE IMPACT WINDOWS and SLIDING DOORS, FLOOD ZONE “X500”. Overlooking the Eagle Golf Course and Ideally Located near the Clubhouse and Campus of World Class Amenities, this

  Mark Lyda GENEROUS PROPERTY

  227 Saint James Park, 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
• 

  

  /24

  Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,055 Sq Ft

  338 Tropic Dr, Osprey, FL 34229

  338 Tropic Dr, Osprey, FL 34229
• 

  

  /57

  $1,199,000

  • 4 Beds
  • 3 Baths
  • 2,925 Sq Ft

  120 Lookout Point Dr, Osprey, FL 34229

  Spacious Custom built home featuring an oversized corner yard, High Ceilings, Updated Kitchen and Bathrooms, Family Room with Wood Burning Fireplace, 3 Bedrooms, 3 Full Baths and a Bonus Room/ 4th Bedroom upstairs. Entertain in the Large Lanai with Outdoor Kitchen overlooking the Pool and wide Greenbelt view. The Stylish and Durable new Metal Roof will protect you for years to come, full

  Sharon Lewis GOLF & BAY PROPERTIES LLC

  120 Lookout Point Dr, 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
• 

  

  /79

  Est $656,640 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,937 Sq Ft

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229

  250 Hidden Bay Dr Unit A203, Osprey, FL 34229
• 

  

  /57

  $569,000

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

  784 Sarabay Rd, Osprey, FL 34229

  Welcome to Your Waterfront Villa in Osprey, Florida!Discover the ultimate seasonal retreat in this beautifully updated 2-bedroom, 2-bathroom single-story villa, designed for stress-free living. Nestled in a private 25-unit secluded community, this waterfront gem offers not only stunning views but also a lifestyle of unparalleled ease and simplicity.Key Features:Move in ready: Move in with ease

  Peggy Lewis COLDWELL BANKER SARASOTA CENT.

  784 Sarabay Rd, 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
• 

  

  /13

  Est $927,333 Not Listed For Sale

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229

  0 Cezanne Dr Unit A4556644, Osprey, FL 34229
• 

  

  /4

  $575,904 New Construction

  • 3 Beds
  • 2 Baths
  • 1,356 Sq Ft

  791 S Tamiami Trail Unit 103, Osprey, FL 34229

  Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $575,904. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOW AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 3 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (2 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 103, 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
• 

  

  /29

  Est $507,561 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  313 Sorrento Dr, Osprey, FL 34229

  313 Sorrento Dr, Osprey, FL 34229
• 

  

  /4

  $527,904 New Construction

  • 2 Beds
  • 2 Baths
  • 952 Sq Ft

  791 S Tamiami Trail Unit 102, Osprey, FL 34229

  Pre-Construction. To be built. PRE CONSTRUCTION STARTING FROM $527,904. NO FLOOD INSURANCE REQUIRED. NOW TAKING RESERVATIONS ON THIS NEW VENICE ISLAND CONDOMINIUM COMMUNITY KNOWN AS ISOLA CASA! 36 CONDOMINIUM UNITS WITHIN 4 SEPARATE BUILDINGS THAT INCLUDE ELEVATORS. THIS UNIT BOASTS 2 BEDROOMS, 2 BATHROOMS WITH A SCREENED LANAI AND HAS A 1-CAR DETACHED GARAGE. (3 BEDROOM AND 2 BATH UNITS ALSO

  Laurie Eshleman PRO GROUP REALTY & PROP MGT

  791 S Tamiami Trail Unit 102, 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
• 

  

  /35

  Est $398,082 Not Listed For Sale

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

  4242 Frontier Ln Unit 106, Osprey, FL 34229

  4242 Frontier Ln Unit 106, Osprey, FL 34229
• 

  

  /43

  $997,000 Pending

  • 3 Beds
  • 3 Baths
  • 2,344 Sq Ft

  3904 Waypoint Ave, Osprey, FL 34229

  This stunning Taylor Morrison Lazio floor plan residence offers an exceptional blend of luxury and tranquility in a desirable West of Trail gated bayfront community. With breathtaking views of the sparkling lake and direct access to the bay, residents can enjoy picturesque sunsets and serenity of daily wildlife sightings. Newer sparkling pool and spa surrounded in pavers. The home features a

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  3904 Waypoint Ave, 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
• 

  

  /31

  Est $595,352 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,004 Sq Ft

  4400 Conchfish Ln, Osprey, FL 34229

  4400 Conchfish Ln, Osprey, FL 34229

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