Discover the charm of coastal living with the convenience of a mainland location in this beautiful Taylor Morrison home, nestled within the exclusive gated community of Bayside in Osprey, FL. The home can be sold either furnished or unfurnished. This peaceful and friendly Intracoastal enclave features just 49 landscape-maintenance-free residences, offering an intimate and effortless coastal lifestyle.
Blending luxury, comfort, and coastal elegance, this meticulously maintained residence showcases thoughtfully curated upgrades throughout. Step inside to find refined details such as elegant crown molding and custom closets in bedrooms, as well as in the pantry and laundry room, ensuring exceptional storage and organization. The split floor plan includes three bedrooms plus a spacious den with pocket doors, creating flexibility for work, relaxation and space for guests.
The designer kitchen is a standout, featuring quartz countertops, stainless steel Monogram GE appliances, a four-burner gas cooktop and handmade pendulum lighting imported from Granada, Spain. Additional upgrades include full-property gutters and a split A/C unit in the garage—ideal for a climate-controlled environment for classic or exotic car enthusiasts.
This private, outdoor oasis is designed for both relaxation and entertainment, with a built-in kitchen and fireplace offering a heated saltwater pool and spa with a brand-new pump and filter. The screened-in lanai was updated in 2025 with a stunning picture-frame view of the water, enhancing the sense of openness and tranquility.
Residents of Bayside enjoy exclusive access to a private community waterfront area complete with a cozy fire pit, a community boat slip with direct access to the Intracoastal Waterway, and a newly built kayak launch. Full restoration of the remaining waterfront amenities will begin in February 2026 and have already been paid for with no future assessment. This prime location is also bikeable to Casey Key, Nokomis Beach, and the Legacy Trail within minutes.
Offering style, comfort, and effortless coastal living in one of Sarasota’s most intimate bayfront communities, this home is ready to welcome you to the best of Florida living.
Blending luxury, comfort, and coastal elegance, this meticulously maintained residence showcases thoughtfully curated upgrades throughout. Step inside to find refined details such as elegant crown molding and custom closets in bedrooms, as well as in the pantry and laundry room, ensuring exceptional storage and organization. The split floor plan includes three bedrooms plus a spacious den with pocket doors, creating flexibility for work, relaxation and space for guests.
The designer kitchen is a standout, featuring quartz countertops, stainless steel Monogram GE appliances, a four-burner gas cooktop and handmade pendulum lighting imported from Granada, Spain. Additional upgrades include full-property gutters and a split A/C unit in the garage—ideal for a climate-controlled environment for classic or exotic car enthusiasts.
This private, outdoor oasis is designed for both relaxation and entertainment, with a built-in kitchen and fireplace offering a heated saltwater pool and spa with a brand-new pump and filter. The screened-in lanai was updated in 2025 with a stunning picture-frame view of the water, enhancing the sense of openness and tranquility.
Residents of Bayside enjoy exclusive access to a private community waterfront area complete with a cozy fire pit, a community boat slip with direct access to the Intracoastal Waterway, and a newly built kayak launch. Full restoration of the remaining waterfront amenities will begin in February 2026 and have already been paid for with no future assessment. This prime location is also bikeable to Casey Key, Nokomis Beach, and the Legacy Trail within minutes.
Offering style, comfort, and effortless coastal living in one of Sarasota’s most intimate bayfront communities, this home is ready to welcome you to the best of Florida living.
Property Details
Price:
$1,000,000
MLS #:
A4670043
Status:
Active
Beds:
3
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAYSIDE
Neighborhood:
34229osprey
Listed Date:
Nov 14, 2025
Finished Sq Ft:
2,323
Total Sq Ft:
3,248
Lot Size:
8,780 sqft / 0.20 acres (approx)
Year Built:
2016
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Bar Fridge, Built-In Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Ice Maker, Microwave, Range Hood, Refrigerator, Tankless Water Heater, Washer
Bathrooms
3 Full Bathrooms
Cooling
Central Air, Humidity Control, Mini-Split Unit(s)
Flooring
Carpet, Porcelain Tile
Heating
Central, Exhaust Fan, Natural Gas
Laundry Features
Electric Dryer Hookup, Inside, Laundry Room, Washer Hookup
Exterior
Architectural Style
Florida
Association Amenities
Cable TV, Gated
Community Features
Fishing, Lake, Community Mailbox, Gated Community – No Guard, Park
Construction Materials
Block, Stucco
Exterior Features
Hurricane Shutters, Lighting, Outdoor Grill, Outdoor Kitchen, Rain Gutters, Sidewalk, Sliding Doors
Roof
Tile
Security Features
Gated Community, Security Gate, Smoke Detector(s)
Financial
HOA Fee
$1,563
HOA Frequency
Quarterly
HOA Includes
Cable TV, Escrow Reserves Fund, Insurance, Maintenance Grounds, Manager, Private Road, Sewer, Trash
HOA Name
Patti Pressano
Tax Year
2024
Taxes
$10,336
Map
Community
- Address3936 WAYPOINT AVENUE OSPREY FL
- SubdivisionBAYSIDE
- CityOSPREY
- CountySarasota
- Zip Code34229
Subdivisions in OSPREY
- ARBORS
- BAY ACRES – RESUB
- BAY OAKS ESTATES
- BAY STREET VILLAGE
- BAYPOINTE VISTA 1
- BISHOPSCOURT TOWNHOME ONE
- BLACKBURN HARBOR RESIDENCES
- BLACKBURN HARBOR WATERFRONT VILLAS
- BLACKBURN POINT MARINA VILLAGE
- BLACKBURN POINT WOODS
- CASEY KEY
- CORDES COVE
- DRY SLIPS AT BELLAGIO VILLAGE
- EDGEWATER/HIDDEN BAY PH 1 BLDG
- EDGEWATER/HIDDEN BAY PH 3
- HERON BAY CLUB SEC I
- HERON HOUSE
- HIDDEN BAY
- HIDDEN BAY; LAKE VISTA
- LAKE VISTA
- MERIDIAN AT THE OAKS PRESERVE
- NORTH CREEK ESTATES
- OAKS
- OAKS 2 PH 1
- OAKS 2 PH 2
- OAKS 2 PHASE 2
- OAKS 3 PH 1
- OSPREY EXECUTIVE PARK
- OSPREY PARK 2
- PALMER
- PALMS/CASEY KEY
- PARK TRACE ESTATES
- PHASE 2 OF BAY STREET
- PINE RANCH
- PINE RANCH EAST
- PINE RUN I
- PINE RUN II
- PINE RUN III
- RIVENDELL
- RIVENDELL WOODLANDS
- SARABAY ACRES
- SAUNDERS V A RESUB
- SIESTA REV RESUB OF PT
- SORRENTO SHORES
- SORRENTO VILLAS 1
- SORRENTO VILLAS 2
- SOUTH CREEK
- SOUTHBAY YACHT & RACQUET CLUB
- THE OAKS
- TOWNS-END SHORES
- VILLAS AT BELLAGIO HARBOR VILLAGE
- VILLAS AT OSPREY HARBOR VILLAGE
- VILLAS AT THE OSPREY HARBOR VILLAGE
- VILLAS/HARBOR VILLAGE
- WEBBS W D ADD
- WILLOWBEND
- WILLOWBEND PH 1
- WILLOWBEND PH 2
- WILLOWBEND PH 3
- WILLOWBEND PH 4
- WINDSOR LODGE AT THE OAKS
Market Summary
Current real estate data for Single Family in OSPREY as of Mar 19, 2026
114
Single Family Listed
125
Avg DOM
452
Avg $ / SqFt
$1,404,714
Avg List Price
Property Summary
- Located in the BAYSIDE subdivision, 3936 WAYPOINT AVENUE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $1,000,000 and features 3 beds, 3 baths, and has approximately 2,323 square feet of living space, and was originally constructed in 2016. The current price per square foot is $430. The average price per square foot for Single Family listings in OSPREY is $452. The average listing price for Single Family in OSPREY is $1,404,714. To schedule a showing of MLS#a4670043 at 3936 WAYPOINT AVENUE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of CORCORAN DWELLINGS REALTY. Disclaimer: All data relating to real estate for sale on this page comes from the Broker Reciprocity (BR) of the Orlando/Tampa – FL. Detailed information about real estate listings held by brokerage firms other than CENTURY 21 Carioti include the name of the listing broker. Neither the listing company nor CENTURY 21 Carioti shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. The Broker providing this data believes it to be correct, but advises interested parties to confirm any item before relying on it in a purchase decision. Copyright 2026. Orlando/Tampa – FL. All rights reserved. 3936 WAYPOINT AVENUE
OSPREY, FL











































































