Own your own slice of tropical paradise on Longboat Key with this beautiful two bedroom two and on half bath Villa in the exclusive Winding Oaks Community located behind the gates of Bay Isles Association. Sweeping views of the Longboat Key Club Harbourside Golf Course and a sparkling inland waterway from your primary bedroom and expansive living/dining room combo that both exit through sliders to a fully enclosed wrap around deck to further enhance your tropical lifestyle. Open floor plan with soaring ceilings and enclosed atrium help to maximize the natural light and make the 2,555 sq feet feel even larger.
Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances.
Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops.
Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets.
Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard.
Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association.
Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Beautifully updated eat in kitchen with striking tray ceiling, ample pantry storage, bright white cabinets, quartz countertops and stainless steel appliances.
Primary owners suite includes an designer walk in closet, updated bath with ceramic tile, walk in shower, double sinks and quartz counter tops.
Split layout offers a private guest suite, with walk in closet, updated ensuite bathroom with ceramic tile, walk in shower and quartz counter tops. Large office with desk nook could easily be converted to another bedroom. Laundry room with storage and sink adjacent to large 2 car garage with epoxy floors and storage cabinets.
Meticulously maintained, Impact Windows and sliders throughout, low maintenance mature plantings in private enclosed front courtyard.
Dog friendly community. Beautiful updated community pool with bathrooms. Beach access via Bay Isles Beach Club which offers a private pavilion with bathrooms, volleyball, picnic tables, grills and ample parking. Low maintenance community where all exteriors and court yards are maintained by the association.
Conveniently located mid key, one mile from Publix and CVS and a short drive to the restaurants and shops of St Armand’s and Downtown Sarasota.
Property Details
Price:
$1,150,000
MLS #:
A4680403
Status:
Active
Beds:
2
Baths:
2.5
Type:
Condo
Subtype:
Condominium
Subdivision:
WINDING OAKS
Neighborhood:
34228longboatkey
Listed Date:
Feb 26, 2026
Finished Sq Ft:
2,555
Total Sq Ft:
3,270
Lot Size:
602,945 sqft / 13.84 acres (approx)
Year Built:
1988
See this Listing
Schools
Elementary School:
Southside Elementary
Middle School:
Booker Middle
High School:
Booker High
Interior
Appliances
Built-In Oven, Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air, Humidity Control
Flooring
Carpet, Tile, Vinyl, Hardwood
Heating
Central, Electric
Laundry Features
Inside, Laundry Room
Exterior
Association Amenities
Pool, Vehicle Restrictions
Community Features
Gulf/Ocean Front, Association Recreation – Owned, Buyer Approval Required, Deed Restrictions, Gated Community – Guard, Pool
Construction Materials
HardiPlank Type
Exterior Features
Awning(s), Courtyard, Garden, Lighting, Private Entrance, Private Yard, Sliding Doors
Parking Features
Garage Door Opener
Roof
Tile
Security Features
Gated Community, Security Gate, Security System, Security System Leased, Smoke Detector(s)
Financial
HOA Fee 2
$922
HOA Includes
24-Hour Guard, Cable TV, Common Area Taxes, Community Pool, Escrow Reserves Fund, Fidelity Bond, Maintenance Structure, Maintenance Grounds, Pool Maintenance, Recreational Facilities, Trash
HOA Name
Neil Fleet
Tax Year
2025
Taxes
$8,565
Map
Community
- Address3435 WINDING OAKS DRIVE UNIT 18 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 Mar 20, 2026
313
Condo Listed
128
Avg DOM
785
Avg $ / SqFt
$1,501,620
Avg List Price
Property Summary
- Located in the WINDING OAKS subdivision, 3435 WINDING OAKS DRIVE UNIT 18 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $1,150,000 and features 2 beds, 3 baths, and has approximately 2,555 square feet of living space, and was originally constructed in 1988. The current price per square foot is $450. The average price per square foot for Condo listings in LONGBOAT KEY is $785. The average listing price for Condo in LONGBOAT KEY is $1,501,620. To schedule a showing of MLS#a4680403 at 3435 WINDING OAKS DRIVE UNIT 18 in LONGBOAT KEY, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
Similar Listings Nearby
Courtesy of MICHAEL SAUNDERS & COMPANY. 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. 3435 WINDING OAKS DRIVE UNIT 18
LONGBOAT KEY, FL