Under contract-accepting backup offers. 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:
Pending
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
- 7981 – LONGBOAT KEY MOORINGS
- 8177 – LONGBOAT KEY MOORINGS MARINA 2
- ARBOMAR APTS
- ARIA LONGBOAT KEY
- AVIGNON VILLAS
- BAILEY-DOBSON
- BAY HARBOUR
- BAY HARBOUR APTS
- BAY ISLES
- BAYOU HAMMOCK
- BAYPORT BCH & TEN PH A
- BAYPORT BCH & TEN PH B
- BAYPORT BCH & TEN PH C
- BAYPORT BCH & TEN PH D
- BAYPORT BCH & TEN PH E
- BAYPORT BCH & TEN PH F
- BAYPORT BEACH & TENNIS CLUB PH D
- BAYVIEW ESTATES
- BEACH HARBOR CLUB
- BEACHES OF LONGBOAT KEY
- BEACHES OF LONGBOAT KEY PH-1
- BEACHPLACE I
- BEACHPLACE II
- BEACHPLACE III
- BOATHOUSE ON LONGBOAT
- BONAIRE AT LONGBOAT KEY
- BUTTONWOOD HARBOR
- CASA DEL MAR
- CEDARS EAST SEC 1
- CEDARS EAST SEC 2
- CEDARS EAST SEC 3
- CEDARS WEST OF LONGBOAT INC
- CLUB LONGBOAT BEACH & TENNIS
- CONRAD BEACH
- CONTINENTALS SEA CLUB III
- COQUINA BEACH
- COREYS LANDING
- COUNTRY CLUB SHORES
- COUNTRY CLUB SHORES IV
- COUNTRY CLUB SHORES SEC 01
- COUNTRY CLUB SHORES SEC 02
- COUNTRY CLUB SHORES SEC 03
- COUNTRY CLUB SHORES SEC 1
- COUNTRY CLUB SHORES SEC 2
- COUNTRY CLUB SHORES, UNIT 5, SEC 3
- COUNTY CLUB SHORES SEC I
- COVERT II
- DOCK ON THE BAY SEC 1
- DREAM ISLAND
- EMERALD HARBOR
- EMERALD HARBOR UNIT 1 REV
- EMERALD POINTE SOUTH
- EN PROVENCE
- FAINE APTS
- 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 4
- GRAND BAY 5
- GRAND BAY 6
- GULFSHORE OF LONGBOAT KEY
- H & M ASSOC
- HARBOR OAKS PH I & II
- HARBOUR COURT
- HARBOUR LINKS
- HARBOUR OAKS
- HARBOUR OAKS 2
- HARBOUR VILLA CLUB AT THE BUCCANEER
- HIDEAWAY BAY SUB
- HOOTON
- INN ON THE BEACH PH I
- INN ON THE BEACH PH II
- INN ON THE BEACH PH III
- ISLANDER CLUB OF LONGBOAT
- JEWFISH KEY
- L AMBIANCE 1
- L AMBIANCE AT LONGBOAT KEY CLUB PH 02
- LA FIRENZA
- LAGUNA YACHT VILLAGE
- LAGUNA YACHT VILLAGE A CONDO
- LANDS END
- LIGHTHOUSE POINT
- LONGBEACH
- LONGBEACH ON LONGBOAT KEY
- LONGBEACH REV OF R P JORDANS SUB
- LONGBOAT ARMS
- LONGBOAT BEACH HOUSE
- LONGBOAT HARBOUR
- LONGBOAT HARBOUR TOWERS
- LONGBOAT KEY
- LONGBOAT KEY CASA DEL MAR
- LONGBOAT KEY ESTATES
- LONGBOAT KEY MOORINGS
- LONGBOAT KEY MOORINGS MARINA
- LONGBOAT KEY MOORINGS MARINA 2
- LONGBOAT KEY TOWERS
- LONGBOAT LANDING
- LONGBOAT SANDPIPERS
- LONGBOAT SHORES REV
- LONGBOAT TERRACE
- MARINA BAY
- MARY REGINA REESE
- MCCALLS BEACH CASTLE
- NEPTUNE ON LONGBOAT KEY
- NEW PASS SHORES
- NORTHGATE OF LONGBOAT KEY
- PELICAN HARBOUR & BEACH CLUB
- PIERRE
- PLAYERS CLUB I
- PLAYERS CLUB III
- PLAYERS CLUB IV
- PORTOBELLO
- POSITANO
- PRESERVE/LONGBEACH
- PRIVATEER NORTH
- PRIVATEER SOUTH
- PROMENADE
- QUEENS HARBOUR
- RAUCH
- RESUB OF LTS 2B&3B OF SLEEPY LAGOON ADD
- SABAL COVE
- SAINT JUDES APTS
- SALTY ACRES
- SANCTUARY II
- SANCTUARY III
- SANCTUARY IV
- SANCTUARY IV LONGBOAT KEY
- SAND CAY
- SANDHAMN
- SANDS POINT
- SEA GATE CLUB
- SEAGRAPE INN
- SEAPLACE
- SEAPLACE I
- SEAPLACE II
- SEAPLACE III
- SEAPLACE IV
- SEAPLACE V
- SEAPLACE VI
- SEASIDE OF LONGBOAT
- SILVER SANDS
- SLEEPY LAGOON
- SLEEPY LAGOON PARK
- SLEEPY LAGOON PARK 2
- SLEEPY LAGOON PART NO 2
- SPANISH MAIN YACHT CLUB
- SPANISH MAIN YACHT CLUB CONDO
- ST REGIS LONGBOAT KEY
- ST. REGIS
- ST. REGIS LONGBOAT KEY
- SUNSET BEACH
- SUNSET BEACH PH 2
- SUTTON PLACE
- T J OXFORD
- TANGERINE BAY CLUB
- TENCON BEACH
- THE BANYAN BAY CLUB
- THE GRANDE AT LONGBOAT KEY
- THE PRESERVE/LONGBEACH
- THE SHORE
- TIFFANY PLAZA
- TRITON COVE
- TURTLE CRAWL SEC 36 TOWNSHIP 35S RANGE 16E
- TWIN SHORES MOBILE HOME
- VEINTE
- VILLA DI LANCIA
- VILLA DI LANCIA PH 1
- VILLA DOS PALMAS
- WATER CLUB 01 AT LONGBOAT KEY
- WATER CLUB AT LONGBOAT KEY
- WATER CLUB II/LONGBOAT KEY
- WATER CLUBI/LONGBOAT KEY CONDO
- WENDY
- WESTCHESTER
- WESTCHESTER APTS
- WESTCHESTER CONDO APTS UN 3
- WHITNEY BEACH
- WHITNEY BEACH CONDO
- WHITNEY BEACH III
- WINDING OAKS
- WINDWARD BAY AMD
Market Summary
Current real estate data for Condo in LONGBOAT KEY as of May 23, 2026
282
Condo Listed
142
Avg DOM
740
Avg $ / SqFt
$1,355,435
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 $740. The average listing price for Condo in LONGBOAT KEY is $1,355,435. To schedule a showing of MLS#a4686581 at 3466 WINDING OAKS DRIVE UNIT 35 in LONGBOAT KEY, FL, contact your LPT Realty agent at 813.694.8061.
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 LPT Realty include the name of the listing broker. Neither the listing company nor LPT Realty 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
