Welcome home to this beautifully maintained 3-bedroom + den, 2-bath pool home nestled on a desirable corner lot, in a cul-de-sac, in Osprey. This home has been impeccably maintained and is an unbeatable location, this is the effortless Florida lifestyle you’ve been searching for.
Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 2½ years ago, and the hot water heater is under 3 years old… meaning the big-ticket items are already handled, so you can simply move in and enjoy. You will find vinyl plank flooring, tile and carpet throughout. The care and attention put into this home shows in every corner.
This home offers space to rest, work, entertain and relax…The flexible den offers the perfect home office, creative studio, 4th bedroom or guest retreat, whatever your lifestyle calls for? along with two spacious bathrooms. Then, step outside to your private screened pool, where the corner lot provides extra breathing room, privacy, and that open, airy feel that’s so rare to find.
Positioned in the heart of Osprey, this home is only minutes from the beloved Legacy Trail? which is ideal for cycling, jogging, and morning walks through some of Florida’s most scenic natural surroundings. Nature lovers will also enjoy the proximity to Oscar Scherer State Park, offering kayaking, wildlife watching, and over 15 miles of trails.
And when the beach calls, it’s answered quickly. Nokomis Beach is just a short drive away for a casual sunset stroll, while the world-famous Siesta Key Beach, home to some of the whitest, finest sand on the planet, is within easy reach for those perfect beach excursions.
523 Oak Bay Drive checks every box: updated systems, private pool, flexible living space, and access to the very best of Florida’s Gulf Coast. People also love the access to top-rated schools, including the nationally acclaimed Pine View School and Laurel Nokomis Elementary, making this the complete package for anyone looking to plant roots in one of Sarasota County’s most sought-after communities. Homes like this don’t last long. Schedule your private showing today.
Peace of mind comes standard here. The roof is less than 7 years old, the AC was replaced just 2½ years ago, and the hot water heater is under 3 years old… meaning the big-ticket items are already handled, so you can simply move in and enjoy. You will find vinyl plank flooring, tile and carpet throughout. The care and attention put into this home shows in every corner.
This home offers space to rest, work, entertain and relax…The flexible den offers the perfect home office, creative studio, 4th bedroom or guest retreat, whatever your lifestyle calls for? along with two spacious bathrooms. Then, step outside to your private screened pool, where the corner lot provides extra breathing room, privacy, and that open, airy feel that’s so rare to find.
Positioned in the heart of Osprey, this home is only minutes from the beloved Legacy Trail? which is ideal for cycling, jogging, and morning walks through some of Florida’s most scenic natural surroundings. Nature lovers will also enjoy the proximity to Oscar Scherer State Park, offering kayaking, wildlife watching, and over 15 miles of trails.
And when the beach calls, it’s answered quickly. Nokomis Beach is just a short drive away for a casual sunset stroll, while the world-famous Siesta Key Beach, home to some of the whitest, finest sand on the planet, is within easy reach for those perfect beach excursions.
523 Oak Bay Drive checks every box: updated systems, private pool, flexible living space, and access to the very best of Florida’s Gulf Coast. People also love the access to top-rated schools, including the nationally acclaimed Pine View School and Laurel Nokomis Elementary, making this the complete package for anyone looking to plant roots in one of Sarasota County’s most sought-after communities. Homes like this don’t last long. Schedule your private showing today.
Property Details
Price:
$540,000
MLS #:
A4696725
Status:
Active
Beds:
4
Baths:
2
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
BAY OAKS ESTATES
Neighborhood:
34229osprey
Listed Date:
Jun 12, 2026
Finished Sq Ft:
2,399
Total Sq Ft:
3,189
Lot Size:
10,287 sqft / 0.24 acres (approx)
Year Built:
1998
See this Listing
Schools
Elementary School:
Laurel Nokomis Elementary
Middle School:
Sarasota Middle
High School:
Venice Senior High
Interior
Appliances
Cooktop, Disposal, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Carpet, Tile, Vinyl
Heating
Central
Interior Features
Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s)
Laundry Features
Laundry Room
Levels
One
Exterior
Attached Garage YN
1
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
South
Exterior Features
Irrigation System, Private Mailbox, Sliding Doors
Garage Spaces
2
Patio And Porch Features
Covered, Enclosed, Patio, Screened
Roof
Shingle
Financial
HOA Fee
$300
HOA Fee Frequency
Annually
HOA Includes
Trash
HOA Name
Sunstate Association Management Group
HOA Phone
941-870-4920
Tax Year
2025
Taxes
$3,448
Map
Community
- Address523 OAK BAY DRIVE OSPREY FL
- SubdivisionBAY OAKS ESTATES
- 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 Jun 18, 2026
88
Single Family Listed
156
Avg DOM
467
Avg $ / SqFt
$1,464,602
Avg List Price
Property Summary
- Located in the BAY OAKS ESTATES subdivision, 523 OAK BAY DRIVE OSPREY FL is a Single Family for sale in OSPREY, FL, 34229. It is listed for $540,000 and features 4 beds, 2 baths, and has approximately 2,399 square feet of living space, and was originally constructed in 1998. The current price per square foot is $225. The average price per square foot for Single Family listings in OSPREY is $467. The average listing price for Single Family in OSPREY is $1,464,602. To schedule a showing of MLS#a4696725 at 523 OAK BAY DRIVE in OSPREY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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Courtesy of KELLER WILLIAMS ON THE WATER S. 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. 523 OAK BAY DRIVE
OSPREY, FL
