Located in one of the most sought-after villa communities on Longboat Key, this well-kept 2-bedroom, 2-bath home in Winding Oaks lives more like a single-family residence—without all the upkeep. Behind the gates of Bay Isles, it offers a great opportunity to enjoy a quiet, established neighborhood known for its natural beauty and relaxed feel. A paver driveway and walkway, surrounded by mature landscaping, lead you to the front door. Inside, high ceilings and warm wood floors immediately make the space feel open and inviting. The finishes are neutral and timeless, and the natural light really does the rest. Impact glass throughout adds both comfort and peace of mind. The main living area flows easily, with a striking corner of sliding glass doors that brings the outdoors in and opens to a spacious, screened, deck. It’s the kind of space you’ll actually use—whether that’s for entertaining, relaxing, or just enjoying the greenery around you.
The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.
The kitchen is nicely laid out with stone countertops, stainless appliances, a tray ceiling, and a large window that keeps things bright. Both bedrooms are generously sized. The primary suite feels like a true retreat, with vaulted ceilings, a walk-in closet, and sliding doors that open to the deck with peaceful nature views. The bathroom is spacious, featuring dual vanities, a Jacuzzi tub, walk-in shower, and well-done tile details. Additional highlights include a two-car garage and a floor plan that offers a nice balance of openness and privacy. Winding Oaks is part of the Bay Isles Harbourside golf course community and offers a gated entrance, community pool, and access to Bay Isles amenities—including deeded beach access through the private Bay Isles Beach Club. It’s an easy, comfortable lifestyle in one of Longboat Key’s most desirable communities.
Property Details
Price:
$795,000
MLS #:
A4686581
Status:
Active
Beds:
2
Baths:
2
Type:
Condo
Subtype:
Condominium
Subdivision:
WINDING OAKS
Neighborhood:
34228longboatkey
Listed Date:
Apr 7, 2026
Finished Sq Ft:
2,039
Total Sq Ft:
2,568
Lot Size:
602,945 sqft / 13.84 acres (approx)
Year Built:
1988
See this Listing
Schools
Interior
Appliances
Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
Bathrooms
2 Full Bathrooms
Cooling
Central Air
Flooring
Tile, Hardwood
Heating
Central, Electric
Interior Features
Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Stone Counters, Thermostat, Window Treatments
Laundry Features
Laundry Room
Levels
One
Exterior
Architectural Style
Other
Association Amenities
Pool
Attached Garage YN
1
Community Features
Deed Restrictions, Pool
Construction Materials
Block, Stucco
Covered Spaces
2
Direction Faces
East
Exterior Features
Irrigation System, Lighting, Sidewalk, Sliding Doors, Storage
Garage Spaces
2
Open Parking YN
1
Parking Features
Driveway, Garage Door Opener
Patio And Porch Features
Covered, Deck, Rear Porch
Roof
Other
View
Water
Financial
HOA Fee 2
$791
HOA Fee 2 Frequency
Annually
HOA Includes
Community Pool, Escrow Reserves Fund, Insurance, Maintenance Structure, Maintenance Grounds, Pest Control, Pool Maintenance, Private Road, Sewer, Trash, Water
HOA Name
Advanced Management / AMIA
HOA Name 2
Bay Isles Homeowners Association
HOA Phone
941-383-3200
HOA Phone 2
941-383-3200
Tax Year
2025
Taxes
$4,919
Map
Community
- Address3466 WINDING OAKS DRIVE UNIT 35 LONGBOAT KEY FL
- SubdivisionWINDING OAKS
- CityLONGBOAT KEY
- CountySarasota
- Zip Code34228
Subdivisions in LONGBOAT KEY
- 360 NORTH PH II
- 7981 – LONGBOAT KEY MOORINGS
- 8177 – LONGBOAT KEY MOORINGS MARINA 2
- ACREAG0001
- AQUARIUS CLUB
- ARBOMAR APTS
- ARIA LONGBOAT KEY
- AVIGNON VILLAS
- BAILEY-DOBSON
- BAY ISLES
- BAYOU HAMMOCK
- BAYPORT BCH & TEN PH A
- BAYPORT BCH & TEN PH C
- BAYPORT BCH & TEN PH D
- BAYPORT BCH & TEN PH E
- BAYPORT BCH & TEN PH F
- BAYVIEW ESTATES
- BEACH HARBOR CLUB
- BEACHES OF LONGBOAT KEY PH-1
- BEACHPLACE I
- BEACHPLACE II
- BEACHPLACE III
- BOATHOUSE ON LONGBOAT
- BONAIRE AT LONGBOAT KEY
- BUTTONWOOD COVE
- BUTTONWOOD HARBOR
- CEDARS EAST SEC 1
- CEDARS EAST SEC 2
- CHARLIES
- CLUB LONGBOAT BEACH & TENNIS
- COLLIER WALKER
- CONDOMINIUM RESIDENCES AT LONGBOAT KEY
- COQUINA BEACH
- COREYS LANDING
- COUNTRY CLUB SHORES
- COUNTRY CLUB SHORES IV
- COUNTRY CLUB SHORES SEC 02
- COUNTRY CLUB SHORES SEC 03
- COUNTY CLUB SHORES SEC I
- DREAM ISLAND
- EMERALD HARBOR
- EMERALD HARBOR UNIT 1 REV
- EMERALD POINTE NORTH
- EN PROVENCE
- FAIRWAY BAY
- FAIRWAY BAY 1
- FAIRWAY BAY 2 PH 1
- FAIRWAY BAY 2 PH 2 & 3
- FAIRWAY BAY 3
- FRACTIONAL SUB
- GRAND BAY 1
- GRAND BAY 2
- GRAND BAY 3
- GRAND BAY 4
- GRAND BAY 6
- GULFSHORE OF LONGBOAT KEY
- HARBOR OAKS PH I & II
- HARBOUR COURT
- HARBOUR OAKS
- HARBOUR OAKS 2
- HARBOUR OAKS PH I & II
- HARBOUR VILLA CLUB AT THE BUCCANEER
- HARRIS BAYOU
- HOOTON
- INFINITY ON LONGBOAT KEY
- INN ON THE BEACH
- INN ON THE BEACH PH II
- INN ON THE BEACH PH III
- ISLANDER CLUB
- ISLANDER CLUB OF LONGBOAT
- ISLANDS WEST
- JEWFISH KEY
- L AMBIANCE
- L AMBIANCE 1
- L AMBIANCE AT LONGBOAT KEY CLUB
- L AMBIANCE AT LONGBOAT KEY CLUB PH 02
- LAGUNA YACHT VILLAGE
- LONGBEACH ON LONGBOAT KEY
- LONGBEACH REV OF R P JORDANS SUB
- LONGBOAT ARMS
- LONGBOAT HARBOUR
- LONGBOAT HARBOUR TOWERS
- LONGBOAT KEY
- LONGBOAT KEY CASA DEL MAR
- LONGBOAT KEY MOORINGS
- LONGBOAT KEY MOORINGS MARINA
- LONGBOAT KEY MOORINGS MARINA 2
- LONGBOAT KEY TOWERS
- LONGBOAT SHORES REV
- LONGBOAT TERRACE
- MARINA BAY
- MCCALLS BEACH CASTLE
- NEPTUNE
- NEPTUNE ON LONGBOAT KEY
- NEW PASS SHORES
- NORTHGATE OF LONGBOAT KEY
- PELICAN HARBOUR
- PELICAN HARBOUR & BEACH CLUB
- PIERRE
- PLAYERS CLUB 3
- PLAYERS CLUB I
- PLAYERS CLUB II
- PLAYERS CLUB III
- PORTOBELLO
- PRESERVE/LONGBEACH
- PRIVATEER NORTH
- PRIVATEER SOUTH
- PROMENADE
- QUEENS HARBOR A/K/A MANCHESTER BAY
- QUEENS HARBOUR
- RAUCH
- REGENT PLACE PH 2
- SABAL COVE
- SAGE LBK
- SALTY ACRES
- SANCTUARY I
- SANCTUARY IV
- SAND CAY
- SANDS POINT
- SARASOTA OUTRIGGER
- SEA GATE CLUB
- SEA PINES
- SEAGRAPE INN
- SEAPLACE
- SEAPLACE I
- SEAPLACE II
- SEAPLACE III
- SEAPLACE V
- SEAPLACE VI
- SHIPMANS ADD
- SLEEP LAGOON PARK
- SLEEPY LAGOON
- SLEEPY LAGOON PARK
- SLEEPY LAGOON PARK 2
- SLEEPY LAGOON PART NO 2
- SPANISH MAIN YACHT CLUB CONDO
- ST REGIS LONGBOAT KEY
- ST. REGIS
- ST. REGIS LONGBOAT KEY
- SUNSET BEACH
- SUNSET BEACH PH 2
- SUTTON PLACE
- TANGERINE BAY CLUB
- THE BANYAN BAY CLUB
- THE PRESERVE/LONGBEACH
- THE SHORE
- THE WESTCHESTER
- TIFFANY PLAZA
- TREE HOUSE
- TURTLE CRAWL SEC 36 TOWNSHIP 35S RANGE 16E
- TWIN SHORES BEACH & MARINA
- TWIN SHORES BEACH AND MARINA, INC.
- TWIN SHORES MOBILE HOME
- VEINTE
- VILLA DI LANCIA PH 1
- VILLA DOS PALMAS
- VIZCAYA AT LONGBOAT KEY PH 01
- VIZCAYA AT LONGBOAT KEY PHASE 1
- WATER CLUB 01 AT LONGBOAT KEY
- WENDY
- WESTCHESTER APTS
- WESTCHESTER CONDO APTS UN 3
- WHITNEY BEACH
- WHITNEY BEACH III
- WINDWARD BAY AMD
Market Summary
Current real estate data for Condo in LONGBOAT KEY as of May 09, 2026
292
Condo Listed
138
Avg DOM
734
Avg $ / SqFt
$1,348,537
Avg List Price
Property Summary
- Located in the WINDING OAKS subdivision, 3466 WINDING OAKS DRIVE UNIT 35 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $795,000 and features 2 beds, 2 baths, and has approximately 2,039 square feet of living space, and was originally constructed in 1988. The current price per square foot is $390. The average price per square foot for Condo listings in LONGBOAT KEY is $734. The average listing price for Condo in LONGBOAT KEY is $1,348,537. To schedule a showing of MLS#a4686581 at 3466 WINDING OAKS DRIVE UNIT 35 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of COLDWELL BANKER 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. 3466 WINDING OAKS DRIVE UNIT 35
LONGBOAT KEY, FL
