ANNUAL RENTAL – Pristine Single family home in the highly sought after community of Bayside in Osprey. The beautiful heated pool home features three bedrooms and three baths as well a private office space. Master bedroom offers an en suite bathroom with dual vanities, walk in shower, oversized walk in closet with built ins. Kitchen is complete with Gas Range, Oversized Island, Quartz Countertops and walk in pantry. Guest bedrooms each have en suite bathrooms too along with one powder bath! Outdoor space is remarkable from the heated pool and spa with southern exposure plus a bonus outdoor kitchen with built in Gas fireplace. Tandem 3 car garage will allow for ample storage for bikes and kayaks. Bayside is a fabulous place to be with opportunity to kayak and paddle board everyday. Bayside also has sunset lovers in mind with a private dock and waterfront sitting area perfect for evening romance. Minutes away from shopping, Venice Beach, Siesta Key Beach, Nokomis Beach and Casey Key Beach. Lots of time to go biking with the new Legacy trail and Oscar Scherer Park. Unfurnished*No smoking* 1st, last & Security for move in!
Property Details
Price:
$4,500
MLS #:
A4686669
Status:
Active
Beds:
3
Baths:
3.5
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
BAYSIDE
Neighborhood:
34229osprey
Listed Date:
Mar 18, 2026
Finished Sq Ft:
2,115
Total Sq Ft:
3,175
Lot Size:
9,667 sqft / 0.22 acres (approx)
Year Built:
2017
See this Listing
Schools
Elementary School:
Venice Elementary
Middle School:
Laurel Nokomis Middle
High School:
Venice Senior High
Interior
Appliances
Dishwasher, Disposal, Dryer, Range, Refrigerator, Washer
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Heating
Central
Laundry Features
Inside, Laundry Room
Exterior
Community Features
Dock, Fishing, Water Access, Gated Community – No Guard, Irrigation-Reclaimed Water, Sidewalks
Financial
HOA Name
Pinnacle Community Robin Estep
Map
Community
- Address3929 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
Property Summary
- Located in the BAYSIDE subdivision, 3929 WAYPOINT AVENUE OSPREY FL is a Rental for sale in OSPREY, FL, 34229. It is listed for $4,500 To schedule a showing of MLS#a4686669 at 3929 WAYPOINT AVENUE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of RE/MAX ALLIANCE GROUP. 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. 3929 WAYPOINT AVENUE
OSPREY, FL