$2,579,000 ($814.08 per sqft)

Est. Mortgage $14,426/mo *

Quick Pre-Approval

133 W BAY STREET, Osprey, FL, 34229

133 W BAY STREET, Osprey, FL, 34229

4 beds

4 Full baths



3,168 sqft

This gated bayfront compound, sitting on half an acre with 100 feet of bay frontage and a brand-new 150-foot dock with boat moorings, offers a range of possibilities. You can use it as a family compound with two duplexes featuring a total of four residences. Alternatively, it could be configured as a primary residence with two additional one-bedroom apartments in a separate building, perfect for family or generating income. Additionally, you have the option to maintain the four current income-producing apartments while creating a 4,600-square-foot bayfront primary residence, as depicted in the artist's renditions in the photos. Located in the upscale Osprey Village-Spanish Point area, this property features four charmingly updated "Old Florida" bungalows from the 1950s, blending historic charm with modern amenities. The main house offers two bedrooms and two bathrooms with stunning bay views, while the duplex includes two one-bedroom, one-bath apartments. Recent upgrades encompass four entirely new HVAC systems with new ductwork throughout and four new hot water tanks. Pristine oak flooring graces the interior, and all four kitchens are equipped with top-of-the-line Bosch appliances, marble backsplashes, quartz countertops, and beautiful marble bathrooms. From the inviting screened porches or the private grounds featuring a 150-year-old Grand Oak Tree, a private beach area, pathways, and mature natural Florida landscaping, you can enjoy picturesque bay views across to North Casey Key and breathtaking sunsets, uninterrupted by condominiums, much like a century ago. All four residences are fully furnished and equipped, including new beds, kitchen wares, linens, furniture, window coverings, and more. On-site laundry facilities are also available. The premium residence boasts full bay views and a spacious private patio, ideal for entertaining. Osprey Village is rapidly developing into one of Sarasota County's premier bayfront communities, with neighboring projects including nine multimillion-dollar homes by Parrot Cove to the north, 49 approved luxury townhomes to the south at the corner of W Bay St & Hwy 41, and proposals for 22 luxury condos a block further south. This property offers ample room for expansion, whether you envision a pool, garage, or pickleball court. Preliminary architectural drawings, included in the photos, showcase a luxury bayfront residence that can be built while retaining the two existing duplexes. These designs incorporate amenities such as a bayside pool, sauna, fitness center, covered parking, and storage on the ground floor. The current duplexes provide instant occupancy or income generation while you work on plans and permits for expansion. The property's prime West of The Trail location makes it an easy walk to Historic Spanish Point, waterfront restaurants, additional dining options, and shopping. You'll also have convenient access to Nokomis Beach, Legacy Trail, Siesta Key, medical facilities, UTC Mall, downtown Sarasota, St. Armand's Circle, The Island of Venice, and all area airports. Private air travel options available on The Island of Venice. Currently zoned RMF1, there is potential to up-zone to maximize the property's potential. This is truly a once-in-a-lifetime opportunity for a gated waterfront compound in a unique part of Little Sarasota Bay. Viewings are by appointment only, and unauthorized entry onto the property is strictly prohibited.




Single-family residential

Furnished Remarks:


Laundry Remarks:

Laundry Room




Boat, Driveway, Guest, Oversized, Parking Pad




Central Air



Lot Size:




Est. Taxes:



Concrete, Stucco


BB/HS Internet Available, Cable Connected, Electricity Connected, Public, Sewer Available, Water Connected

Lot Description:

FloodZone, In County, Near Public Transit, Oversized Lot

View Description:

Trees/Woods, Water

Elementary School:

Venice Elementary

Middle School:

Venice Area Middle

High School:

Venice Senior High

Days on Market:


Pet Policy:



Built-In Oven, Cooktop, Dishwasher, Dryer, Electric Water Heater, Microwave, Refrigerator, Washer

Min Lease Term:

No Minimum

MLS #:


Community Info

School Info

Victory Baptist Academy

Enrollment: 56

Distance: 0.76 Miles

The Study Center

Enrollment: 4

Distance: 4.56 Miles

Community Rating:

Gulf Gate Elementary School

Rating: 8/10

Enrollment: 711

Distance: 4.58 Miles

Community Rating:

Imagine School At Palmer Ranch

Rating: 6/10

Enrollment: 502

Distance: 4.69 Miles

Community Rating:

Saltmeadow School

Enrollment: 17

Distance: 5.05 Miles

Mangrove School of Sarasota

Enrollment: 71

Distance: 5.05 Miles

European Academy Of Early Education

Enrollment: 53

Distance: 5.43 Miles

Community Rating:

Sarasota Middle School

Rating: 9/10

Enrollment: 1,244

Distance: 5.66 Miles

Community Rating:

Laurel Nokomis School

Rating: 8/10

Enrollment: 1,181

Distance: 5.77 Miles

Community Rating:

NewGate School

Enrollment: 155

Distance: 5.87 Miles

Community Rating:

Ashton Elementary School

Rating: 10/10

Enrollment: 1,060

Distance: 5.88 Miles

Community Rating:

Prew Academy

Enrollment: 43

Distance: 6.1 Miles

Community Rating:

Riverview High School

Rating: 6/10

Enrollment: 2,606

Distance: 6.15 Miles

Community Rating:

Sarasota Virtual Academy (Virtual Franchise)

Enrollment: 0

Distance: 6.16 Miles

Sarasota County Technical Institute

Enrollment: 4

Distance: 6.16 Miles

Sarasota Virtual Instruction (Course Offerings)

Enrollment: 0

Distance: 6.23 Miles

Sarasota Virtual School

Enrollment: 45

Distance: 6.23 Miles

Suncoast Polytechnical High School

Rating: 8/10

Enrollment: 565

Distance: 6.24 Miles

Community Rating:

Wilkinson Elementary School

Rating: 3/10

Enrollment: 511

Distance: 6.5 Miles

Community Rating:


Enrollment: 57

Distance: 6.51 Miles

Phillippi Shores Elementary School

Rating: 9/10

Enrollment: 789

Distance: 6.52 Miles

Community Rating:

Hershorin Schiff Community Day School

Enrollment: 252

Distance: 6.64 Miles

Community Rating:

Island Village Montessori School

Rating: 7/10

Enrollment: 662

Distance: 6.69 Miles

Community Rating:

Sarasota Suncoast Academy

Rating: 7/10

Enrollment: 670

Distance: 6.72 Miles

Community Rating:

Out-Of-Door Academy

Enrollment: 742

Distance: 6.72 Miles

Community Rating:

Epiphany Cathedral School

Enrollment: 183

Distance: 7.02 Miles

Community Rating:

Incarnation Catholic School

Enrollment: 165

Distance: 7.28 Miles

Community Rating:

Lakeview Elementary School

Rating: 9/10

Enrollment: 599

Distance: 7.41 Miles

Community Rating:

Venice Elementary School

Rating: 9/10

Enrollment: 570

Distance: 7.46 Miles

Community Rating:

Brookside Middle School

Rating: 7/10

Enrollment: 754

Distance: 7.47 Miles

Community Rating:

Venice Senior High School

Rating: 6/10

Enrollment: 2,236

Distance: 7.69 Miles

Community Rating:

Brickhouse Academy

Enrollment: 31

Distance: 7.7 Miles

Community Rating:

Brentwood Elementary School

Rating: 6/10

Enrollment: 655

Distance: 7.99 Miles

Community Rating:

School Information courtesy of GreatSchools

Walk Score


Listing courtesy of AYERS AND ASSOCIATES REAL ESTATE Phone: 941-266-3193