Gulf to Bay Vacation Living! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Building "F" 4540 Gulf of Mexico - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Steps to Gulf & Steps to Bay! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Florida Room & Great Room Sarasota Bay Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Gulf View From Entry Way & Kitchen - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Bay View When You Enter! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Turn Around and Gulf View from Entry & Kitchen! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Bay Views from Both Florida Room and Great Room! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Newly Remodeled Open Kitchen with Gulf Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Kitchen Gulf Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Newly Remodeled Open Kitchen with Gulf Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Gaze at the Gulf From New Kitchen Island Seating! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Great Room & Kitchen! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Great Room with Sarasota Bay Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Great Room with Sarasota Bay Views! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Great Room to Florida Room/Lanai - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Florida Room - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Bay View from Florida Room & Great Room - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Primary Bedroom with "En Suite" New Bathroom - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
New Primary "En Suite" Bathroom - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
New Primary "En Suite" Bathroom - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Guest Bedroom - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Guest Bedroom - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Brand New Guest Bathroom! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Laundry Closet - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Entrance to Penthouse 2! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Evening Gulf Sunset from Catwalk! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Evening Gulf Sunset from Catwalk! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Evening Gulf Sunset from Catwalk! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Building "F" Rear View! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Steps to Bay & Steps to Beach! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Aerial of Gulf/Bay & "F" Building - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Entry - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
"F" Building Beach Access - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
"A" to "E" Building Beach Access! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
"A" to "E" Building Beach Access! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Private Deeded Beach Path at Northend of Property. - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Uncrowded Beaches of Longboat Key! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Gulf Beach Bliss! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Amazing Colors of the Gulf! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
North Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
North Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
North Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
South Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
South Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
South Marina - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Manatees at South Marina! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Kayak Storage at Both South & North Marinas! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Kayak Launches at Both South & North Marinas! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Kayak Fun between "F" & "E" Buildings! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Clubhouse and Management Office! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Clubhouse - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Clubhouse - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
2 Saunas! Men & Women! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Library - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fitness Room! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fitness Room! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fitness Room! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Shuffleboard - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Shuffleboard - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Bike Racks Throughout the Property - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Resort Style Amenities! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Tennis/Pickleball Courts - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
North Main Clubhouse Pool - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
North Main Clubhouse Pool - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
South Pool - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
South Pool - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fire Pits Throughout the Property! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fire Pits Throughout the Property! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Fire Pits Throughout the Property! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
1/2 Mile of Nature Trails! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
1/2 Mile of Nature Trails! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Tranquility Bench! Southern-Most Point! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Entry at Night! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Entry at Night! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Sunrise Birds! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Windward Bay Sunrise! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
Welcome Home to Windward Bay! - 4540 GULF OF MEXICO DR #PH2, LONGBOAT KEY
78 photos

$9,000

4540 GULF OF MEXICO DR #PH2
LONGBOAT KEY, FL 34228
Listed by Debby McCaig · COLDWELL BANKER REALTY
Bedrooms
2
Bathrooms
2
Living area
1,325 sqft
Year built
1975

About this home

RARE LATE-FALL OPPORTUNITY: NOVEMBER & DECEMBER 2026 AVAILABLE FOR A TWO-MONTH MINIMUM STAY AT $10,000, OFFERING A $8,000 SAVINGS. START EVERY DAY ON VACATION WITH A SUNRISE AND END IT WITH A SUNSET. From the first light of sunrise dancing across Sarasota Bay to the breathtaking sunsets over the Gulf of Mexico, this penthouse offers the best of both worlds, and the very essence of Longboat Key living. Bay views grace the eastern side of the residence, while the large kitchen window and entry door offer views west toward the Gulf. Gather each evening along the Gulf-view catwalk to watch spectacular sunsets paint the sky over the water. It's a daily tradition cherished by owners, neighbors, and guests alike, often enjoyed from a beach chair with a favorite beverage in hand. Designed for comfort and relaxation, this two bedrooms and two bath coastal retreat features a newly remodeled open kitchen with island seating, two newly renovated bathrooms, and an inviting open living and dining area. The bright Florida Room is filled with natural light, creating the perfect spot for morning coffee, reading, or simply taking in the peaceful surroundings. Arrive with ease and park directly in your private under-building garage parking space, complete with a dedicated storage closet for all your beach gear. Perched on the top floor, this penthouse residence offers an added sense of tranquility with no unit above. The beautifully updated kitchen is fully equipped for everything from casual breakfasts to gourmet dinners. Pick up fresh ingredients from local farmer's markets or explore the many outstanding dining destinations located just minutes away. Nestled within the 26-acre waterfront community of Windward Bay, guests enjoy access to an impressive collection of resort-style amenities. Highlights include two heated swimming pools, tennis and pickleball courts, two marinas, kayak storage, shuffleboard, a clubhouse with kitchen, library, fitness center, saunas, multiple fire pits, and barbecue areas throughout the grounds. Nature lovers will appreciate the abundance of wildlife, scenic walking paths, and more than a half mile of waterfront trails. Whether your days are spent boating, fishing, kayaking, beachcombing, or simply relaxing in the Florida sunshine, the location places you close to everything. Downtown Sarasota, St. Armands Circle, Bridge Street, Historic Cortez Fishing Village, championship golf courses, shopping, dining, and renowned arts and cultural attractions are all nearby. Guests return year after year for the exceptional combination of comfort, location, and coastal charm. In fact, one couple has made this their January through March home away from home for many seasons. More than just a place to stay, this is the kind of vacation retreat where cherished memories are made and lasting traditions begin. Your perfect Longboat Key vacation begins here.

Highlights

Waterfront

Property details

MLS #
MFRA4706064
Property type
Condominium
Subdivision
WINDWARD BAY AMD
Status
Active
Days on market
N/A
On market date
September 15, 2026
Stories
N/A
Total bathrooms
2
Garage spaces
1
Parking spaces
N/A
Lot size
26.67 acres
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Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
BAYSHORE ELEMENTARY SCHOOL
4.16 mi away · Grades -1-5
Nearest school -- attendance-zone data not available here
4.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
677
Student:teacher ratio
14.7:1
District
MANATEE
Middle
ELECTA LEE MAGNET MIDDLE SCHOOL
4.27 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
3.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
780
Student:teacher ratio
16.6:1
District
MANATEE
HighCharter
STATE COLLEGE OF FLORIDA COLLEGIATE SCHOOL
4.38 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
1.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
504
Student:teacher ratio
25.2:1
District
MANATEE

Walkability

Blended score for LONGBOAT KEY's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

44
Somewhat walkable
out of 100
EPA National Walkability Index
11.8 / 20 -- Above average walkable
Google Places amenity density
21 / 100
Restaurants & cafes1
Grocery stores0
Parks5
Schools0
Transit stops1
Pharmacies0

Mortgage calculator

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Est. monthly payment
$204/mo
$1,800 down
$7,200 loan
Principal & interest$47
Property tax (est.)$8
Home insurance (est.)$150

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Data source: Listing information provided by Stellar MLS (mfrmls) via Trestle/CoreLogic. Last updated 24 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.