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
Single-familyProperty Type
1950Year Built
1.68 acresLot Size
$2,451Est. Price/Sq.Ft.
Listed by Brett Newman• Coldwell Banker Schmitt Islamorada
Listed by Margo Newman• Coldwell Banker Schmitt Islamorada
Bought with Grace Langs• Coastal Realty of the Florida Keys
In the heart of Upper Matecumbe lies one of Islamorada's premier properties. Over an acre and a half located directly on the Florida Bay offering sunsets, protected dockage and pool overlooking the open water. Completely renovated 3/4.5 main house and 1/1 guest. Impact windows, sliders and entry doors. Entire home in and out has been recently painted. Large laundry room with multiple storage cabinets. The grounds are covered with fruit trees, orchids, large shade trees and your own bayfront beach. The bay frontage offers a sand filled jetty, boat basin and pristine waters for snorkeling, swimming and paddelboarding.
FLKMLS #557205
Jul 29, 2013
Sold
$2,000,000
$590/sq ft
Feb 8, 2012
Listed
$2,399,000
$708/sq ft
+21
In Heart of Upper Matecumbe lies one of Islamorada's Premier Properties. This property is located on the Fl Bay offering spectacular Sunset's, protected dockage, (up to 30ft), pool overlooking the open water. The grounds are covered with fruit trees, orchids and native trees; The 1.68 acres offers 2 homes, the Main house is a 3/3,and smaller home is a 1/1, which sits on a separate parcel The property has been home to the Legendary Dick Pope Jr, his wife Frances and their family for over 40 years. The property offers privacy, spectacular water views, and of course the convenience of being in the heart of Upper Matecumbe. The pristine waters of the Fl Bay are home to Bonefish, Permit, Tarpon, as well as dozens of other species, offering fisherman the opportunity to catch fish on some of the best waters in the world. The home has protected dockage for boats up to 30', a sand filled jetty offering wide open views of the bay, and an above ground concrete pool that sits on the edge of the Fl Bay. The property also owns 0.34 acres of bay bottom as well. The Main home is CBS construction with a solid concrete roof which allows for expansion and upgrades if desired. The home has had several upgrades over the years including new windows and sliding doors. The second home or guest cottage is just under 700 sq ft and sleeps up to 4 people. This home does sit on its own lot. The grounds are filled with orchids, air-plants, fruit trees and native vegetation, making this one of the most tropical settings on the island.
Year
Property tax
Land + Additions
Assessment*
2025
$57,654 (+6.6%)
2024
$54,079 (+6.5%)
2023
$50,760 (+10.8%)
2022
$45,824 (+16.4%)
2021
$39,369 (+3.0%)
$3,083,012 + $801,209
$3,884,221
2020
$38,212 (+60.9%)
$3,083,012 + $664,397
$3,747,409
2019
$23,753 (+13.7%)
$3,083,012 + $664,397
$3,747,409
2018
$20,900 (+1.5%)
$1,381,691 + $547,665
$1,929,356
2017
$20,596 (−3.8%)
$1,381,691 + $559,951
$1,941,642
2015
$21,420 (+11.2%)
$1,402,519 + $498,888
$1,901,407
2014
$19,260
Tax history for 128 Madeira Rd
Year
Property tax
Land + Additions
Assessment*
2025
$57,654 (+6.6%)
2024
$54,079 (+6.5%)
2023
$50,760 (+10.8%)
2022
$45,824 (+16.4%)
2021
$39,369 (+3.0%)
$3,083,012 + $801,209
$3,884,221
2020
$38,212 (+60.9%)
$3,083,012 + $664,397
$3,747,409
2019
$23,753 (+13.7%)
$3,083,012 + $664,397
$3,747,409
2018
$20,900 (+1.5%)
$1,381,691 + $547,665
$1,929,356
2017
$20,596 (−3.8%)
$1,381,691 + $559,951
$1,941,642
2015
$21,420 (+11.2%)
$1,402,519 + $498,888
$1,901,407
2014
$19,260
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Public record
Zoning
Permits
Beds
1
Baths
1
Stories
1
Lot width
—
Lot depth
—
Lot size
0.34 Acres
Year renovated
2018
Sq. Ft.
530
Year built
1950
Style
Single Family Residential
County
Monroe County
APN
2863 37 00399470000000
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 10, 2026.
RE
Residential Estate District
The purpose of the residential estate RE zoning district is to identify existing residential estates, and vacant estate properties designated for residential uses; This zoning district is established within the Residential Low RL FLUM category.
Permitted uses
Include but are not limited to:
Housing-Single unit
Nov 15, 2022 • Final
Roofing
Roofing
Jun 3, 2022 • Final
Electrical
Electrical
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking / Garage Information
Vehicle Storage: Covered Parking, Off Street Parking, Trailer Storage, Open Parking, Guest Parking
Exterior Features: Detached Guest Qtrs, Sandy Beach, Storage, Outdoor Shower, Fruit Tree(s)
Has Pool
Pool Information: Concrete, In Ground, Decked
Pool Info: Other Surroundings: Elevated pool
Porch/Balcony: Open Porch/Balcony
Security
On Premises System, Other Security
Property Features
Has Handicap Access
On Waterfront
Waterfront Type: Bay Front, Open Water, Gulf Front
Waterview: Bay/Gulf View, Open Water View
Property Information
Property Condition: Updated/Remodeled
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: Yes
Min Rental Days: 7
Lot Information
Acres: 1.68
Zoning: RE - Residential Estate
Land Size: 1 Less Than 2 Acres
Control Depth: 3
Flood Zone: AE, VE
Building Information
Year Built: 1,950
Sq. Ft. Source: Tax Records
Sq. Ft. Remarks: approx. - both houses
Building Style: Conch, Ground Level
Building Style: Above Flood: Unknown
Construction: CBS, Concrete
Roof: Concrete Roof
Subdivision/Neighborhood
Subdivision: Strattons (82.5)
Financial
Tax Information
Taxes: $18,690.83
Tax Year: 2,017
Tax Exemptions: None
Financial Information
Terms: Buyer Obtain Finance
Utilities
Utility Information
Utilities: Buyer to Verify, Water Separate Meter, Municipal Sewer, Elect Separate Meter, FKAA, Cable Available
Pre-Wired: Cable
Has Public Sewer Hook-up
Location
Multi-Unit Information
# of Total Units: 2
Homeowners Association Information
Association Info: 1st Right of Refusal: No
Fee Includes: None
Location Information
Side: Bay/Gulf
Mile Marker: 82.50
Directions: Turn on either List Street (Mangrove Mike's) or on Madeira Rd (Lorelei Restaurant) and drive toward Bay. Turn on to Madeira and property is on bayside, 128, with manatee mailbox.
Neighborhood Features
Other Area Features
Public facts
Beds: 1
Baths: 1.0
Sq. Ft.: 530
Stories: 1.0
Lot Size: 0.34 acres
Style: Single Family Residential
Year Built: 1950
Year Renovated: 2018
County: Monroe County
APN: 2863 37 00399470000000
Home facts updated by county records on Jul 10, 2026
Around this home
Schools
Plantation Key School
Public PreK-8 • Assigned • 7.3mi
10/10
Coral Shores High School
Public 9-12 • Assigned • 7.6mi
5/10
Provided by GreatSchools
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
10/10 Flood Factor
Estimated 80%+ chance of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
Heat Factor
We're working on getting current and accurate heat risk information for this home.
10/10 Wind Factor
99% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 1 days in 30 years
Provided by First Street
Historical weather
Islamorada, FL • 33036
Average low and high temperatures (°F)
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Sun exposure
In this area, properties receive around 9.5 hours in
June and 7 hours in December, placing it above the
U.S. average for solar exposure.
9.5 hrs
7 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$7.89M – $9.55M
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