Homes in ZIP Code 34229

/61
$1,050,000 Pending
- 4 Beds
- 3 Baths
- 3,321 Sq Ft
742 Shadow Bay Way, Osprey, FL 34229

Under contract-accepting backup offers. Welcome to Luxury Living in Rivendell! Nestled on a premium, private lot with serene lake and preserve views, this impeccably maintained, custom-built Arthur Rutenberg home offers elegance, comfort, and thoughtful design in every detail. Boasting 3,321 sq ft of refined living space, this residence features an open split floor plan, soaring ceilings, and

Reeny Kaney RE/MAX ALLIANCE GROUP

742 Shadow Bay Way, 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

/43
Est $408,480 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
4317 Expedition Way Unit 101, Osprey, FL 34229

4317 Expedition Way Unit 101, Osprey, FL 34229

/65
$1,099,000 Pending
- 5 Beds
- 3 Baths
- 3,912 Sq Ft
678 Clear Creek Dr, Osprey, FL 34229

Under contract-accepting backup offers. Looking for quality craftsmanship??? This exceptional home was built by US Homes, with a unique distinction — the original owner was the president of US Homes at the time of construction, personally overseeing every detail to ensure top-tier quality and craftsmanship throughout. This exquisitely remodeled 5-bedroom, 3-bath estate, nestled in one of Sarasota

Dena Olson EXIT KING REALTY

678 Clear Creek 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

/31
Not Listed For Sale
0 Webb St Unit A4546155, Osprey, FL 34229

0 Webb St Unit A4546155, Osprey, FL 34229

/48
$1,200,000 Pending
- 3 Beds
- 2 Baths
- 2,531 Sq Ft
142 Dory Ln, Osprey, FL 34229

Southbay Yacht & Racquet Club, The waterfront Community with Resort-Style Amenities. Welcome to this beautiful three-bedroom two-bathroom home featuring a private pool and spa, perfect for relaxing or entertaining year-round. Located in a highly sought-after waterfront community, this property offers access to a private marina, clubhouse, community pool and scenic park-ideal for enjoying the

Sharon Lewis GOLF & BAY PROPERTIES LLC

142 Dory Ln, 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

/25
Est $251,686 Not Listed For Sale
13 Bay Ave, Osprey, FL 34229

13 Bay Ave, Osprey, FL 34229

/6
$34,500
- 2 Beds
- 1 Bath
124 Happy Haven Dr Unit 8, Osprey, FL 34229

Make your new home in Happy Haven, a well-maintained, professionally managed manufactured home community! Own a 1966, 1bed/1bath, 564 sqft. home in a great neighborhood. This one won't be on the market for long! Take advantage of this offer now and live in one of the state's most attractive areas. Let us show you around the place! Call and schedule a viewing today! Financing information available.

Tori Coil Happy Haven

124 Happy Haven Dr Unit 8, 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

/21
Est $326,418 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,135 Sq Ft
4192 Expedition Way, Osprey, FL 34229

4192 Expedition Way, Osprey, FL 34229

/14
$234,000
- 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
$600,000 Sold Apr 18, 2025
- 2,887 Sq Ft
- $208/SF
- 24 Days On Market
- 3 Beds
- 3.5 Baths
- Built 1995
402 Pine Ranch Rd E, Osprey, FL 34229

LLocated 1-2 mile from the legacy trail off Bay St. in Osprey. Built on one acre in 1995. This is a 3-bedroom 3.5 bath home that has a lot of potential. The large office in the front of the home could be made into a 4th bedroom. The family room has a fireplace, built-in shelving and has a view of the pool. The pool bath is behind the family room with direct access to the pool. The master suite

Ronnie Caron CARON REALTY INC

402 Pine Ranch Rd E, Osprey, FL 34229

/33
Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,440 Sq Ft
155 Edgewood Dr, Osprey, FL 34229

155 Edgewood Dr, Osprey, FL 34229

/62
$785,500
- 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 is bordering 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 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
$650,000 Sold Apr 18, 2025
- 2,431 Sq Ft
- $267/SF
- 113 Days On Market
- 3 Beds
- 2 Baths
- Built 1995
610 Pine Ranch Rd E, Osprey, FL 34229

Price Reduced on this Magnificent three bedroom, two bath home with den, heated pool, fenced yard for privacy in Bay Oaks Estates in Osprey. This fantastic, well maintained home has it all including a LOW annual fee of $270. Features include an updated kitchen with large farmer sink, quartz counters, Bosch Range with stainless hood, Bosch dishwasher, Samsung Refrigerator with plenty of storage,

Kim Klee COLDWELL BANKER REALTY

610 Pine Ranch Rd E, Osprey, FL 34229

/30
Not Listed For Sale
- 2 Beds
- 2 Baths
- 952 Sq Ft
168 Edgewood Dr, Osprey, FL 34229

168 Edgewood Dr, Osprey, FL 34229

/4
$42,500
570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229

Dry boat slip for sale at Osprey Harbor Village, hurricane-protected dry storage with top-tier amenities! Keep your boat safe from Floridas unpredictable weather while enjoying all the benefits of a full-service marina. Located just before the swing bridge to Casey Key at ICW Marker 33 (north of the Blackburn Point Bridge), this slip fits boats up to 33L x 10.5W x 6.5H. With valet boat service,

Daniel Treiman MICHAEL SAUNDERS & COMPANY

570 Blackburn Point Rd Unit CASEY 11, Osprey, FL 34229
/2
$1,050,000 Sold Apr 16, 2025
- 2,871 Sq Ft
- $366/SF
- 70 Days On Market
- 3 Beds
- 2 Baths
- Built 1979
247 Keel Way, Osprey, FL 34229

No hurricane problems here! impact windows and storm curtains on the lanai helped to keep this home safe. Also located in an X flood zone! This beautiful home located in "west of the trail", Southbay Yacht and Racquet Club is a very sought after location. One of the few communities with it's own marina and very reasonable dock rental fees only available to homeowners in the community. This home

Pat Williams PAT WILLIAMS REALTY, LLC

247 Keel Way, Osprey, FL 34229

/60
Est $378,870 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,528 Sq Ft
4129 Frontier Ln Unit 104, Osprey, FL 34229

4129 Frontier Ln Unit 104, Osprey, FL 34229

/8
$44,000
570 Blackburn Point Rd Unit 6, Osprey, FL 34229

Dry Boat Slip for Sale – Osprey Harbor Village, Sarasota CountySecure your spot in one of Sarasota County’s premier boating destinations with this hurricane-protected dry boat slip at Osprey Harbor Village. Designed to offer both protection and convenience, this indoor slip ensures your boat is shielded from Florida’s unpredictable weather — potentially reducing your insurance premiums by

Rick Bumbaca AZZURRO REALTY

570 Blackburn Point Rd Unit 6, Osprey, FL 34229
/2
$385,000 Sold Apr 16, 2025
- 1,346 Sq Ft
- $286/SF
- 244 Days On Market
- 2 Beds
- 2 Baths
- Built 1963
329 Bay Vista Ave, Osprey, FL 34229

One or more photo(s) has been virtually staged. Come see this charming house in Osprey It features 2 bedrooms , 2 baths and a 2 car garage .The main bedroom has a sitting room. The kitchen has been updated with white cabinets with soft close drawers, granite countertops, stainless steel refrigerator and dishwasher. Save on electricity with the fully owned solar panel system. The entire yard is

Colette Jay HORIZON REALTY INTERNATIONAL

329 Bay Vista Ave, Osprey, FL 34229

/3
Est $230,500 Not Listed For Sale
436 Glenwood Ave, Osprey, FL 34229

436 Glenwood Ave, Osprey, FL 34229

/34
$800,000 Open Sat 8AM - 7PM
- 5 Beds
- 4 Baths
- 3,395 Sq Ft
851 Placid Lake Dr, Osprey, FL 34229

One or more photo(s) has been virtually staged. Your dream home is waiting for you! This home has Fresh Interior Paint, Fresh Exterior Paint, Partial flooring replacement in some areas. Discover a bright interior tied together with a neutral color palette. You'll love cooking in this kitchen, complete with a spacious center island and a sleek backsplash. Head to the spacious primary suite with

Karen Albright OPENDOOR BROKERAGE LLC

851 Placid Lake Dr, Osprey, FL 34229
/2
$945,000 Sold Apr 15, 2025
- 2,677 Sq Ft
- $353/SF
- 4 Days On Market
- 3 Beds
- 3 Baths
- Built 1978
128 Sea Anchor Dr, Osprey, FL 34229

New to the market, your dream home awaits in the exclusive private marina community of Southbay Yacht and Racquet Club. For boating enthusiasts, this is the opportunity you’ve been waiting for! In the sought-after Southbay Yacht and Racquet Club, this stunning residence combines spacious design with the best of Florida living, just steps from your boat. Imagine waking up and stepping out onto

Lisa Napolitano PREMIER SOTHEBYS INTL REALTY

128 Sea Anchor Dr, Osprey, FL 34229

/37
Est $408,494 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,574 Sq Ft
117 Navigation Cir Unit 101, Osprey, FL 34229

117 Navigation Cir Unit 101, Osprey, FL 34229

/49
$897,000 Open Sat 1PM - 3PM
- 3 Beds
- 2 Baths
- 2,483 Sq Ft
678 Crane Prairie Way, Osprey, FL 34229

It’s always about the view and the new tile roof in June 2025 plus the Tesla whole-house solar system comprising 26 roof panels harnessing 8.45-kilowatt capacity of energy. This incredible benefit includes two Power Walls and a wall-mounted charging station supporting most brands of electric vehicles. The solar system reduces house energy costs to $27 a month and zero for your electric car. When

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

678 Crane Prairie Way, Osprey, FL 34229
/2
$390,000 Sold Apr 15, 2025
- 1,334 Sq Ft
- $292/SF
- 21 Days On Market
- 2 Beds
- 2 Baths
- Built 1970
441 N Shore Dr, Osprey, FL 34229

Bring your BOAT or RV and store ON YOUR LOT. West of the Trail! Welcome home to Sorrento Shores, nestled perfectly between the vibrant communities of Sarasota and Venice, yet tucked away from the hustle and bustle of city life in the charming town of Osprey. This sought-after neighborhood offers spacious lots, a relaxed atmosphere, and the added bonus of low HOA fees and no CDD to worry

Dawn Barnett EXIT KING REALTY

441 N Shore Dr, Osprey, FL 34229

/57
Est $701,199 Not Listed For Sale
- 3 Beds
- 3 Baths
- 2,630 Sq Ft
6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

6100 Jessie Harbor Dr Unit 503, Osprey, FL 34229

/61
$474,900
- 3 Beds
- 2 Baths
- 1,883 Sq Ft
7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229

PENTHOUSE CONDO IN WATERFRONT COMMUNITY!Experience luxury coastal living in this spacious 3-bedroom, 2-bath penthouse condo, perfectly situated on a tranquil canal with dockage and direct, bridge-free access to the Intracoastal Waterway and the Gulf. This impressive 3rd-floor residence features an open floor plan with expansive rooms, plantation shutters, and three private balconies—ideal for

Toy Coxey KW COASTAL LIVING

7303 Jessie Harbor Dr Unit 7303, Osprey, FL 34229
/2
$1,160,000 Sold Apr 15, 2025
- 1,787 Sq Ft
- $649/SF
- 10 Days On Market
- 3 Beds
- 2 Baths
- Built 1978
131 Tina Island Dr, Osprey, FL 34229

Welcome to your dream waterfront oasis! This exquisite 3-bedroom, 2-bathroom residence offers unparalleled water views and mesmerizing sunsets from the expansive pool deck. The generous outdoor living area is perfect for hosting gatherings or enjoying peaceful moments by the canal. The thoughtfully designed split-bedroom layout ensures privacy, making it ideal for accommodating guests or family

Sarah McGuire WHITE SANDS REALTY GROUP FL

131 Tina Island Dr, Osprey, FL 34229

/37
Est $602,146 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,846 Sq Ft
514 Oak Bay Dr, Osprey, FL 34229

514 Oak Bay Dr, Osprey, FL 34229

/43
$689,000
- 4 Beds
- 2 Baths
- 2,145 Sq Ft
819 Shadow Bay Way, Osprey, FL 34229

A new 2025 roof. This stunning 2,145-square-foot pool home is in the premier community of Rivendell. Live so beautifully! This maintenance-free, tropically landscaped corner lot home has been eloquently updated and maintained. Featuring four bedrooms, formal dining room, two baths, two-car garage, fenced-in backyard, beautiful pool and lanai, and tile throughout most of the home. The inviting

Crystal Cosby, LLC PREMIER SOTHEBYS INTL REALTY

819 Shadow Bay Way, Osprey, FL 34229
/2
$700,000 Sold Apr 15, 2025
- 2,504 Sq Ft
- $280/SF
- 69 Days On Market
- 3 Beds
- 2.5 Baths
- Built 2004
521 Luminary Blvd, Osprey, FL 34229

This stunning Lee Wetherington home, in the prestigious Willowbend community of Osprey, showcases the natural beauty of Florida through its beautifully designed Stanford, rarely available floor plan. Home has a 22-kilowatt whole-house generator. Set against the backdrop of a sparkling lake, the residence features a great room, dining area, kitchen, dinette, owner’s suite all benefiting from one

Tamara Currey PREMIER SOTHEBY'S INTERNATIONAL REALTY

521 Luminary Blvd, Osprey, FL 34229

/16
Est $340,213 Not Listed For Sale
- 2 Beds
- 2 Baths
- 967 Sq Ft
340 Pennsylvania Ave, Osprey, FL 34229

340 Pennsylvania Ave, Osprey, FL 34229

/99
$6,750,000
- 6 Beds
- 5 Baths
- 4,893 Sq Ft
622 Bayshore Dr, Osprey, FL 34229

Welcome to 622 Bayshore Drive - where coastal luxury meets modern sophistication on one of the most sought-after stretches of Little Sarasota Bay. Tucked away on a rare and expansive .78-acre gated estate, this custom-built, contemporary masterpiece offers 90 feet of pristine waterfront, unmatched privacy, and a lifestyle defined by serenity, style and seamless connection to the water. Designed

Terri Derr MICHAEL SAUNDERS & COMPANY

622 Bayshore Dr, Osprey, FL 34229
/2
$879,352 Sold Apr 15, 2025
- 1,937 Sq Ft
- $454/SF
- 14 Days On Market
- 3 Beds
- 2 Baths
- Built 2024
280 Hidden Bay Dr Unit 402, Osprey, FL 34229

One or more photo(s) has been virtually staged. Under Construction. Photos are a representation of multiple floor plans in the building. Watch the most breathtaking sunsets from your private extra-large, screened-in balcony as you look out across the bay to the barrier island of Casey Key! Centrally located between historic Venice and vibrant downtown Sarasota is Edgewater at Hidden Bay. This

Thomas Netzel PREMIER SOTHEBY'S INTERNATIONAL REALTY

280 Hidden Bay Dr Unit 402, Osprey, FL 34229

/63
Est $1,169,759 Not Listed For Sale
- 4 Beds
- 3 Baths
- 3,048 Sq Ft
113 Harbor House Dr, Osprey, FL 34229

113 Harbor House Dr, Osprey, FL 34229

/43
$685,000
- 1,887 Sq Ft
6 Bay Acres Ave, Osprey, FL 34229

Exceptional Investment Opportunity – Profitable Remodeled Duplex in Prime Osprey Location! Updated in 2021 with a new roof, modern kitchens, contemporary appliances, stylish flooring, and upgraded electrical systems. This income-producing gem is currently generating $112,000 in gross annual short-term rental income, making it an unbeatable addition to your investment portfolio.Nestled on

Bogdan Osipov OSIPOV GROUP REAL ESTATE

6 Bay Acres Ave, Osprey, FL 34229

Showing Results 161 - 200, Page 5 of 18

Florida Osprey 34229

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