Homes in ZIP Code 34229

• 

  

  /2

  $832,000 Sold Apr 14, 2025

  • 1,988 Sq Ft
  • $419/SF
  • 178 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2006

  14041 Bellagio Way Unit 313, Osprey, FL 34229

  Welcome to the highly desirable community of The Villas at Osprey Harbor! This light and bright end unit with a private entrance is loaded with recent, tasteful updates including a fully renovated kitchen in 2022 with high end rift cut white oak custom cabinetry and a quartz breakfast bar, induction stove, updated baths, 24-by-24 porcelain tile, lighting, fans, fresh paint throughout, a coffee

  Megan George PREMIER SOTHEBYS INTL REALTY

  14041 Bellagio Way Unit 313, Osprey, FL 34229
• 

  

  

  /31

  Est $342,833 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 874 Sq Ft

  21 Shumard St, Osprey, FL 34229

  21 Shumard St, Osprey, FL 34229
• 

  

  

  /24

  $670,000

  • Land
  • 0.34 Acre
  • $1,970,588 per Acre

  458 N Shore Dr, Osprey, FL 34229

  Discover the perfect canvas for your dream home with this exceptional vacant lot located in the desirable Sorrento Shores community of Osprey, Florida. Spanning 0.34 acres, this spacious lot offers ample room for creative design and construction. With a generous front footage of 100 feet and dimensions that allow for multiple building possibilities, this property situated "WEST of Trail," is

  Matthew Charland LLC GULF SHORES REALTY

  458 N Shore Dr, Osprey, FL 34229
• 

  

  /2

  $275,000 Sold Apr 11, 2025

  • 900 Sq Ft
  • $306/SF
  • 33 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1963

  208 Pennsylvania Ave, Osprey, FL 34229

  PRICED to SELL! Incredible Opportunity, Don\'t miss this one! Nice 3Br 2Ba single family home on large fenced corner lot in Osprey, Florida near Venice Beach. NO HOA! Large lot with plenty of space for additions, RV or Boat parking, swimming pool, etc. One of the best deals in the area! Turn-key and ready to move in, New paint

  Stephen Hachey FLAT FEE MLS REALTY

  208 Pennsylvania Ave, Osprey, FL 34229
• 

  

  

  /18

  Est $268,809 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 996 Sq Ft

  248 Washington Ave, Osprey, FL 34229

  248 Washington Ave, Osprey, FL 34229
• 

  

  /41

  $164,900

  • 2 Beds
  • 2 Baths
  • 863 Sq Ft

  170 Edgewood Dr, Osprey, FL 34229

  YOUR PERFECT FLORIDA RETREAT AWAITS.... Imagine spending your winter days in a swimming pool or in the warm waters and beautiful sands of Florida Gulf Coast beaches. This pristine 2 Bed, 2 Bath home located in the Arbors Mobile Park has been meticulously maintained and has many upgrades and extras. Open plan kitchen has dining area and built-in china cabinet. The master bedroom is ensuite and

  Roberta Burish KW SUNCOAST

  170 Edgewood Dr, Osprey, FL 34229
• 

  /2

  $925,000 Sold Apr 10, 2025

  • 2,166 Sq Ft
  • $427/SF
  • 31 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Under Construction. Under construction. The photos are a representation of multiple floor plans in the building. Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. The gated, 12-acre resort-style community is nestled on the water’s edge of Little Sarasota Bay in Osprey. The final waterfront building

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 401, Osprey, FL 34229
• 

  

  /13

  Est $1,309,936 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
• 

  

  /35

  $310,000 Open House 7/27

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

  4267 Expedition Way, Osprey, FL 34229

  Welcome to Bay Street Village, Osprey - Perfectly nestled between the vibrant cities of Sarasota and Venice - only minutes to the pristine shoreline of Nokomis Beach. This desirable gated community features a resort style heated pool, clubhouse and a fitness center designed to enhance your Florida life style. Enjoy local dining, shopping, and many arts and cultural attractions. This

  Judi Cipollina COLDWELL BANKER REALTY

  4267 Expedition Way, Osprey, FL 34229
• 

  /2

  $400,000 Sold Apr 08, 2025

  • 1,574 Sq Ft
  • $254/SF
  • 115 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 2016

  4239 Expedition Way, Osprey, FL 34229

  NEW PRICE AND PRICED TO SELL - THE ONLY AVAILABLE 2 CAR GARAGE UNIT LISTED IN THE COMMUNITY! Welcome to Bay Street Village, a highly sought-after gated condominium community in the heart of Osprey. This rarely available FIRST FLOOR, EXTENDED 2-car garage condo offers plenty of space for vehicles and gear, making it ideal for those with an active lifestyle. The beautiful home is being sold

  Joe Cleary RE/MAX ALLIANCE GROUP

  4239 Expedition Way, Osprey, FL 34229
• 

  

  /50

  Est $810,383 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
• 

  

  /32

  $380,000

  • 2 Beds
  • 2 Baths
  • 1,165 Sq Ft

  1801 Highland Rd, Osprey, FL 34229

  Enjoy this Key West-style townhome in Towns-End Shores-maintenance-free living at its best! Beautifully upgraded with porcelain wood look tile flooring, crown molding and 9-foot ceilings, this 2 bed/2 bath townhome features granite countertops, wood cabinetry, an enclosed Florida room, and a spacious 2-car garage. Enjoy a tropical private backyard oasis and community pool amenities. Original

  Beth Johnston KELLER WILLIAMS ISLAND LIFE REAL ESTATE

  1801 Highland Rd, Osprey, FL 34229
• 

  /2

  $512,500 Sold Apr 07, 2025

  • 2,147 Sq Ft
  • $239/SF
  • 34 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2005

  1152 Beachcomber Ct Unit 15, Osprey, FL 34229

  Coastal Living at its Finest! Discover this beautifully designed 3 bedroom, 2.5 bath townhouse in the desirable Blackburn Point Marina Community! Enjoy prime location just steps from the Intercoastal Waterway, the Gulf of Mexico, Blackburn State Park, the Blackburn Point Marina, and the beloved Casey Key Fish House and Tiki Bar along with the new Deep Lagoon Restaurant. Step inside to find a

  Jennifer Bright BRIGHT REALTY

  1152 Beachcomber Ct Unit 15, Osprey, FL 34229
• 

  

  /35

  Est $715,057 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 2,721 Sq Ft

  579 Oak Bay Dr, Osprey, FL 34229

  579 Oak Bay Dr, Osprey, FL 34229
• 

  

  /55

  $3,300,000

  • 4 Beds
  • 5.5 Baths
  • 7,842 Sq Ft

  550 Dove Pointe, Osprey, FL 34229

  Sited at the end of a quiet cul-de-sac behind the gates of the prestigious Oaks Clubside in Osprey, Florida, this stately traditional custom estate offers refined living in one of Sarasota County’s most exclusive communities. Perfectly positioned on over three-quarters of an acre, the residence boasts serene preserve and fairway views, capturing the essence of Florida luxury living. Inside,

  Jennifer Linehan MICHAEL SAUNDERS & COMPANY

  550 Dove Pointe, Osprey, FL 34229
• 

  /2

  $290,000 Sold Apr 07, 2025

  • 1,120 Sq Ft
  • $259/SF
  • 195 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1957

  427 Washington Ave, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Charming 3/2 Bungalow with Endless Possibilities with a freshly painted interiorStep into this delightful 3-bedroom, 2-bathroom bungalow and instantly feel at home. The large screened-in porch welcomes you with ample space for a cozy porch swing, where you can enjoy your morning coffee or evening cocktails while soaking in the serene

  Kelly Jenkins KW COASTAL LIVING II

  427 Washington Ave, Osprey, FL 34229
• 

  

  /25

  Est $555,796 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
• 

  

  /6

  $37,900

  • 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
• 

  /2

  $559,500 Sold Apr 04, 2025

  • 2,165 Sq Ft
  • $258/SF
  • 56 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2004

  1219 Chalet Ct, Osprey, FL 34229

  This stunning Lee Wetherington-built home in Osprey's Willowbend community beautifully combines Florida's natural charm with elegant living. The desirable Willow floor plan borders a wide greenbelt with tasteful landscaping that enhances its curb appeal. The enlarged lanai offers a serene private space, just a short distance to the community's heated pool and spa. Inside, the home showcases

  Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

  1219 Chalet Ct, Osprey, FL 34229
• 

  /2

  Est $949,414 Not Listed For Sale

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

  127 Turquoise Ln, Osprey, FL 34229

  127 Turquoise Ln, Osprey, FL 34229
• 

  

  /13

  $599,000 Open Sun 1PM - 3PM

  • 4 Beds
  • 2 Baths
  • 1,861 Sq Ft

  4428 Conchfish Ln, Osprey, FL 34229

  Chic Modern Escape in the Heart of Palms at Casey Key! This charming residence is located in a flood zone that is not considered a high-risk zone (Zone X) and features four spacious bedrooms and two full bathrooms, along with a two car garage and a large driveway for additional parking. Step into the kitchen, and you'll find elegant quartz countertops, upgraded 42" Timberlake latte cabinets, a

  Mariana Georgieva HORIZON REALTY INTERNATIONAL

  4428 Conchfish Ln, Osprey, FL 34229
• 

  /2

  $1,051,025 Sold Apr 04, 2025

  • 1,937 Sq Ft
  • $543/SF
  • 2 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2024

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Under Construction. Penthouse-level unit with unparalleled panoramic water views of Sarasota Bay and the Gulf of Mexico. A condominium with a view like this is seldom offered for sale and the top floor equals top views! Watch the most breathtaking sunsets from your private, extra-large, screened-in balcony on the fifth and top floor of this

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  280 Hidden Bay Dr Unit 502, Osprey, FL 34229
• 

  

  /64

  Est $279,000 Not Listed For Sale

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

  224 Woodland Dr, Osprey, FL 34229

  224 Woodland Dr, Osprey, FL 34229
• 

  

  /71

  $2,299,900

  • 5 Beds
  • 3.5 Baths
  • 3,236 Sq Ft

  180 Lookout Point Dr, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Welcome to 180 Lookout Point Drive in the sought-after Southbay Yacht & Racquet Club—an extraordinary residence taken fully down to the studs and reimagined as a like-new, luxury smart home. Set on a .4-acre lot in Flood Zone X (no lender-required flood insurance), this five-bedroom, 3.5-bath, 3,236-square-foot home blends solid block construction

  Katy McBrayer PREMIER SOTHEBY'S INTERNATIONAL REALTY

  180 Lookout Point Dr, Osprey, FL 34229
• 

  /2

  $600,000 Sold Apr 03, 2025

  • 1,975 Sq Ft
  • $304/SF
  • 86 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1996

  818 Oak Pond Dr, Osprey, FL 34229

  This is your Dream Home! Upgrades galore and ready to move-in. 4 Bedrooms 2 baths with sparkling caged pool and stunning new paver brick deck (2022), oversize covered lanai, outdoor shower, in a very private setting. NEW ROOF in 2019, NEW AC in 2019, whole house RE-PLUMBED in 2021. Enjoy the exquisite Ivory tone PORCELAIN TILE FLOORS throughout most of the home. NEW GRANITE COUNTERS in kitchen

  Jacqueline Middleton SUNSET REALTY

  818 Oak Pond Dr, Osprey, FL 34229
• 

  

  /41

  Est $524,542 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,868 Sq Ft

  541 Meadow Sweet Cir, Osprey, FL 34229

  541 Meadow Sweet Cir, Osprey, FL 34229
• 

  

  /75

  $188,000

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

  137 Woodland Place, Osprey, FL 34229

  Unbelievable!!! A 2-bedroom/2-bathroom, West of Trail condo for under $200,000! Come home to this warm, cozy and charming unit and enjoy a cup of tea on your tranquil and private outside deck, nestled in a wooded, West of Trail paradise! The condo is surrounded by a backdrop of nature and you can enjoy the outdoors on three balconies which is wonderfully unique! The unit features generous room

  Priscilla Adams COMPASS FLORIDA LLC

  137 Woodland Place, Osprey, FL 34229
• 

  /2

  $237,000 Sold Mar 31, 2025

  • Land
  • 0.97 Acre
  • $244,330 per Acre

  • 34 Days On Market

  14 Old Venice Rd, Osprey, FL 34229

  Great opportunity to purchase a 1 acre parcel close to town with many possibilities. The property has been cleared of all structures and out buildings. The approximate 1 acre parcel is ready to build in the town of Osprey. Property is close to Pine View school and minutes to the beaches. The Legacy trail and Oscar Scherer State park are near by. Shopping, restaurants, and Medical offices are also

  Glenn Davis COLDWELL BANKER SARASOTA CENT.

  14 Old Venice Rd, Osprey, FL 34229
• 

  

  /59

  Est $1,010,227 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
• 

  

  /33

  $684,900

  • 4 Beds
  • 2 Baths
  • 2,434 Sq Ft

  866 Oak Briar Ln, Osprey, FL 34229

  Welcome to the highly desirable Park Trace Estates where residents enjoy low HOA fees! This beautiful pool home is move-in ready and features a split floor plan with three bedrooms and a 4th-bedroom/office giving you lots of space and flexibility. Many upgrades include pool resurfacing and tile, solar pool heater, pool pump, pool filter, AC, tankless water heater, refrigerator and dishwasher.

  Brian Leakeas COLDWELL BANKER REALTY

  866 Oak Briar Ln, Osprey, FL 34229
• 

  /2

  $885,000 Sold Mar 31, 2025

  • 2,100 Sq Ft
  • $421/SF
  • 115 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1997

  236 Hidden Bay Dr Unit 504, Osprey, FL 34229

  One or more photo(s) has been virtually staged. Waterfront resort-style living in a gated community with breathtaking panoramic views over Little Sarasota Bay. This fifth-level end unit, with elevator access, has been tastefully remodeled. It offers three bedrooms, three full en-suite baths, a screened/glassed-in lanai for entertaining, all while watching spectacular sunsets over the Intracoastal

  Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

  236 Hidden Bay Dr Unit 504, Osprey, FL 34229
• 

  

  /99

  Est $745,132 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
• 

  

  /35

  $129,900

  • 2 Beds
  • 2 Baths
  • 1,152 Sq Ft

  310 Tropic Dr, Osprey, FL 34229

  Priced well below market. Great condition - move in ready. Being offered furnished. The roof is only 5 years old. This one is in the pet section. In addition to the 1152 sq ft of living area is an enclosed porch with windows and a mini-split A/C unit adding about 180 sq ft. There is a nice screened in porch just off the carport. There is plenty of storage in the workshop behind the carport and

  Hansel Pitts COLDWELL BANKER SARASOTA CENT.

  310 Tropic Dr, Osprey, FL 34229
• 

  /2

  $324,000 Sold Mar 28, 2025

  • 1,430 Sq Ft
  • $227/SF
  • 34 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2017

  76 Explorer Dr Unit 104, Osprey, FL 34229

  Location Location Location! Welcome home to this beautifully upgraded 3-bedroom, 2-bath end unit, perfectly positioned in a sought-after, pet-friendly gated community. Built for peace of mind, this condo features sturdy block stucco construction and hurricane-impact windows and doors, ensuring both durability and security. Step inside and feel the spaciousness of the open-concept design,

  Pan Steele, GRI COLDWELL BANKER REALTY

  76 Explorer Dr Unit 104, Osprey, FL 34229
• 

  

  /57

  Est $701,463 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
• 

  

  /60

  $1,279,000

  • 3 Beds
  • 2.5 Baths
  • 2,830 Sq Ft

  1527 Buoy Ln, Osprey, FL 34229

  Beautifully and thoroughly recently updated beach style home in Southbay Yacht and Racquet club featuring 10 foot ceilings. 2024 tile roof, 2023 driveway, cabinets, lighting, appliances, tile and carpet are just the beginning. 2023 pool and spa led lighting, Pentair controller, saltwater conversion, and owned 250 gallon propane. Dry bar with ice maker, wine fridge, and beverage fridge. Large

  Matthew Lewis BRIGHT REALTY

  1527 Buoy Ln, Osprey, FL 34229
• 

  /2

  $1,350,000 Sold Mar 28, 2025

  • 2,778 Sq Ft
  • $486/SF
  • 11 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2004

  409 N Point Rd Unit 704, Osprey, FL 34229

  Enjoy luxury condo living at its finest. A rare offering, this 3 bedroom, 3 bath residence enjoys a spacious floor plan seldom available. Besides an incredible master suite, large guest bedrooms and modern bathrooms, it has a formal dining room, an office/den and an open great room with adjoining kitchen and breakfast nook. From the moment you step off your private elevator and enter, you will

  Steve Abbe COLDWELL BANKER REALTY

  409 N Point Rd Unit 704, Osprey, FL 34229
• 

  

  /96

  Est $1,087,460 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
• 

  

  /86

  $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 country clubs on the gulf coast, The Oaks Golf and Country Club. Previously redesigned, this tuscan style home in the quaint and charming Bishops Court in the Oaks Preserve features 2 bedrooms, 2 1/2 baths, a spacious kitchen, and a great room overlooking a lovely lake view surrounded by

  Rosalie Phillips MICHAEL SAUNDERS & COMPANY

  33 Bishops Court Rd Unit 118, Osprey, FL 34229
• 

  /2

  $745,000 Sold Mar 27, 2025

  • 2,594 Sq Ft
  • $287/SF
  • 17 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 2003

  401 N Point Rd Unit 401, Osprey, FL 34229

  Can luxury living and great value go hand and hand? It can with this well priced residence in Meridian at The Oaks Preserve. Nestled above the treetops, this luxury condo is the perfect solution for those who want to live a carefree lifestyle and enjoy all the amenities of Sarasota’s premier golf and country club. With 3 bedrooms, a den and 3 bath, this unit offers room for residents and guests

  Steve Abbe COLDWELL BANKER REALTY

  401 N Point Rd Unit 401, Osprey, FL 34229

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