• Home
  • Property Search
    • Key West Real Estate
      • Key West Homes
      • Key West Condos
      • Key West Townhomes
      • Key West Commercial
      • Key West Land
    • Florida Keys Real Estate
      • Florida Keys Homes
      • Florida Keys Condos
      • Florida Keys Townhomes
      • Florida Keys Commercial
      • Florida Keys Land
    • MLS Search
  • Property Estimate
  • Neighborhoods
    • Casa Marina
    • Golf Club
    • Key Haven
    • Meadows
    • Midtown
    • New Town
    • Old Town
    • Sunset Key
    • Truman Annex
  • Islands
    • Big Coppitt Key
    • Big Pine Key
    • Cudjoe Key
    • Duck Key
    • Islamorada
    • Key Colony Beach
    • Key Largo
    • Lower Matecumbe Key
    • Marathon Key
    • Plantation Key
    • Sugarloaf Key
    • Summerland Key
  • Contact Us

Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

$4,500,000
128 Madeira Road
Upper Matecumbe Key Islamorada, FL 33036
MLS# 582614
Status: Closed
4 beds  |  4.1 baths  |  3389 sqft


Almost 2 Acres
  1 / 84  
Almost 2 Acres Islamorada Bayfront Welcome Home The Winston Sunset Estate Moonlit Dip Relax Your Backyard Sunset Living Room Watch Sunset in the A/C The Winston Bayfront Estate Downtown Location Bayfront Large Bayfront Parcel Bayfront Beach & Pool Blue Water Site Dimensions Endless Grounds Entry Gate Old Keys Entry Long Gravel Drive Very Private Open Space Mature Trees Shady Trees Coquina Driveway The Winston Bay View from Door Welcome Sitting Room Kitchen Kitchen Kitchen - Living Living Room View Living Room View Bayfront Porch Love Beach Cool Off Yes Basin Entry Gone Fishin All Yours Dockage Sunset Sunset Dip Outdoor shower IMG_5126 Porch Time Wow Living Room Downstairs Hall Master Master Master Let's Go Upstairs Upstairs Bed 2 Bath 2 Bed 3 Bed 3 View Full Bath 3 Down Side Door Side View Out Front Guest House Guest House Guest House Guest House Guest House Guest House Guest House Guest House Bath Guest House Bath Bonus Space Bonus Space Guest House Guest House Guest House Sunset Come Back Soon Sunset Paradise Don't Look Back Star Bright Good night moon

Property Description
Open Bayfront Estate in the very heart of downtown Islamorada with dockage, separate guest house and a bayfront pool! ''The Winston'' is currently featured by AWE TV on Episode 8 of ''Selling Private Islands'' for its amazing location and endless views. Enjoy nightly sunsets from your living room in the modern, updated 3 bed/3.5 bath main home originally built in the 1950s by one of the area's founding families. Welcome guests to stay in the comfort of their own 1/1 guest house and enjoy fishing, boating, fine dining, shopping, art festivals and Islamorada's 3 hometown breweries! This expansive parcel also offers a long winding driveway through a lush front garden on 1.68 acres of upland. The estate also includes .34 acres of baybottom which encompasses the boat basin and jetty. Must se

Details
Maps
Contract Information
Current Price: $4,500,000
Listing Date: 2018-11-02
Listing Board: Florida Keys
Leased Price Monthly: $4,500,000
As is Rght to Inspct: Yes
Potential Short Sale: No
Bank Owned: No
Species List: Yes
Location, Tax & Legal
Street #: 128
Street Name: Madeira
Street Suffix: Road
Key/Island: Upper Matecumbe Key Islamorada
State/Province: FL
Zip Code: 33036
County: Monroe
Subdivision: Strattons (82.5)
Area: 23 - Upper Matecumbe
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 1950
Total Units: 2
Lot Size: 150 x 560 approx
Lot SqFt: 73181
Acres: 1.68
Living Apx SqFt: 3389
SqFt Source: Tax Records
Total Bedrooms: 4
Full Baths: 4
Half Baths: 1
Total Baths: 4.1
Rentals Allowed: Yes
Min Rental Days: 7
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 30
Dock: Concrete
Seawall: Cut/Natural
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
Pool Info
Other Surroundings: Elevated pool
Financial Status
Bank Owned: No
Potential Short Sale: No
Status Change Info
Under Contract Date: 2019-05-28
Leased Date: 2019-07-31
Leased Price Monthly: $4,500,000
Status: Closed
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Bay Front; Gulf Front; Open Water
Waterview: Bay/Gulf View; Open Water View
Dockage: Basin
Property Condition: Updated/Remodeled
Building Style: Conch; Ground Level
Vehicle Storage: Covered Parking; Guest Parking; Off Street Parking; Open Parking; Trailer Storage
Furnished: Negotiable
Cooling: Ductless
Utilities: Buyer to Verify; Cable Available; Elect Separate Meter; FKAA; Municipal Sewer; Water Separate Meter
Interior Features: Granite Counter Top; Split Bedroom; Storage
Pre-Wired: Cable
Specialty Rooms: Laundry Room; Utility Room
Appliances: Oven; Range; Refrigerator; Washer
Exterior Features: Detached Guest Qtrs; Fruit Tree(s); Outdoor Shower; Sandy Beach; Storage
Pool Info: In Ground; Concrete; Decked
Construction: CBS; Concrete
Floor: Tile
Roof: Concrete Roof
Pets: Pets Allowed
Neighborhood Feature: Other Area Features
Security: On Premises System; Other
Land Size: 1 Less Than 2 Acres
Terms: Buyer Obtain Finance
Title: Title Ins - Buyer

Listing Office: Coldwell Banker Schmitt Islamorada

Last Updated: September - 03 - 2024

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


Search powered by FBS Products
Create A Real Estate Portal
With a portal you are able to:
  1. Save your searches
  2. Get updates on listings
  3. Track listings
  4. Add notes and messages
  5. Personalize your dashboard

Anchor Line Realty on Social Media:

Facebook
Facebook
fb-share-icon
Twitter
Visit Us
Follow Me

E-mail Us Directly

Please provide details below:

  • Home
  • Property Search
  • Property Estimate
  • Neighborhoods
  • Islands
  • Contact Us

Copyright © 2026 · AgentPress Pro on Genesis Framework · WordPress · Log in

David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)