Tucked within Winding Oaks, one of Longboat Key’s most sought-after villa communities, this 3BR/3BA residence offers the scale and comfort of a single-family home paired with the simplicity of maintenance-free living. From the paver drive and walkway to the stepped front entry, the residence creates an inviting first impression before opening into a home defined by volume, light and connection to the outdoors. Step inside and soaring ceilings immediately create a sense of openness, while high-set windows invite natural light to move throughout the living spaces. Tile flooring and soft neutral tones create a clean backdrop that complements the peaceful setting just beyond the glass. Renovated in November 2025, the kitchen has been thoughtfully opened and redesigned into a true centerpiece for gathering and everyday living. A substantial island with seating anchors the space, along with stone countertops, white cabinetry, stainless steel appliances, a range hood, wine refrigerator and tile backsplash. An abundance of windows and an adjoining sitting area create a bright, welcoming space whether hosting guests or enjoying a quiet morning. The dining area transitions naturally into the living room, where cathedral ceilings, a corner fireplace and sliding glass doors connect the interior to the outdoors. Beyond, an expansive screened deck overlooks the community lake and fountain, creating a peaceful setting with multiple areas for dining, relaxing or entertaining. Privacy walls on either side enhance the feeling of seclusion while keeping the water views front and center. The primary suite is spacious and calming, featuring vaulted ceilings, engineered wood floors, a wall of sliding glass doors opening to the deck and a large walk-in closet with extensive built-ins. Also renovated in November 2025, the primary bath offers dual vanities, a walk-in shower, dressing area and separate water closet. Guest accommodations are equally well planned. One bedroom includes an en suite bath and walk-in closet, while another is currently configured as an office space with sliding glass doors opening to a private patio. Updated baths throughout, an in-residence laundry room and a 2-car garage add convenience. Set within the Harbourside golf course community, Winding Oaks offers a serene environment with a gated entrance, community pool and spa, and access to the full range of Bay Isles amenities, including deeded beach access through the private Bay Isles Beach Club.
Property Details
Price:
$1,150,000
MLS #:
A4695005
Status:
Active
Beds:
3
Baths:
3.5
Type:
Condo
Subtype:
Condominium
Subdivision:
WINDING OAKS
Neighborhood:
34228longboatkey
Listed Date:
Jun 2, 2026
Finished Sq Ft:
2,608
Total Sq Ft:
3,323
Year Built:
1988
See this Listing
Schools
Interior
Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Range Hood, Refrigerator, Tankless Water Heater, Washer, Wine Refrigerator
Bathrooms
3 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Tile
Heating
Central, Electric
Interior Features
Cathedral Ceiling(s), Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Thermostat, Walk-In Closet(s), Window Treatments
Laundry Features
Laundry Room
Levels
One
Exterior
Architectural Style
Other
Association Amenities
Maintenance, Pool
Attached Garage YN
1
Community Features
Buyer Approval Required, Deed Restrictions, Pool
Construction Materials
Wood Frame
Covered Spaces
2
Direction Faces
East
Exterior Features
Sidewalk, Sliding Doors
Garage Spaces
2
Parking Features
Garage Door Opener
Patio And Porch Features
Rear Porch
Roof
Tile
Spa Features
Heated, In Ground
View
Water
Waterfront Features
Lake Front
Window Features
Blinds, Window Treatments
Financial
HOA Fee 2
$1,523
HOA Fee 2 Frequency
Annually
HOA Includes
24-Hour Guard, Community Pool, Manager, Private Road
HOA Name
Advanced Management – AMI / Neil Fleet
HOA Name 2
Bay Isles Homeowners Assoc
HOA Phone
941-383-3200
HOA Phone 2
941-383-3200
Tax Year
2025
Taxes
$10,320
Map
Community
- Address3460 WINDING OAKS DRIVE UNIT 38 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 Jun 11, 2026
260
Condo Listed
153
Avg DOM
762
Avg $ / SqFt
$1,423,422
Avg List Price
Property Summary
- Located in the WINDING OAKS subdivision, 3460 WINDING OAKS DRIVE UNIT 38 LONGBOAT KEY FL is a Condo for sale in LONGBOAT KEY, FL, 34228. It is listed for $1,150,000 and features 3 beds, 4 baths, and has approximately 2,608 square feet of living space, and was originally constructed in 1988. The current price per square foot is $441. The average price per square foot for Condo listings in LONGBOAT KEY is $762. The average listing price for Condo in LONGBOAT KEY is $1,423,422. To schedule a showing of MLS#a4695005 at 3460 WINDING OAKS DRIVE UNIT 38 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. 3460 WINDING OAKS DRIVE UNIT 38
LONGBOAT KEY, FL
