20 Avacado Street, Upper Sugarloaf Key, FL 33036 - Photo 1

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$15,950,000

For Sale
Active
Single Family
6 Beds
7 Full Baths
1 Partial Bath
6,680 Sq. Ft.
Updated 6 hours ago

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Property Description

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWS Welcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters. The residence includes 6 bedrooms, 7.5 bathrooms and was designed to blend coastal elegance with effortless waterfront living. In addition to the bedrooms, the main home provides a complete gym and office. A separate guest house includes a living room, full kitchen, laundry room, and two bedrooms with ensuite bathrooms. Located in the heart of Islamorada, the home is walkable to several restaurants. Agents Welcome

Full Property Details

Full Property Details for 20 Avacado St

General

Price: $15,950,000
Taxes: $65,124 (2025)
Status: Active
Type: Single Family
Source: 927
MLS ID: 618816
Updated: 5/13/2026
Added to Site: 77 day(s) ago

Interior

Number of Rooms: 10
Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Ice Machine, Microwave, More Appliances, Oven, Refrigerator, Washer, Wine Cooler

Rooms

Bathrooms

Total Bathrooms: 8
Full Bathrooms: 7
Half Bathrooms: 1

Bedrooms

Total Bedrooms: 6

Additional Information

Pool: Yes
Pool Description: Concrete, In Ground, Decked

Location

Area: 23 - Upper Matecumbe
County: Monroe
Subdivision: Misc Upper Matacumbe (82.0)
Driving Directions: From Miami, drive south on Overseas Highway. Turn right onto De Leon Ave (between Sandals and Tiny's Gas. Right onto Avacado Street. Go to dead end (white gate).

Community

Assoc. Fees Include: None
Pets Allowed: Yes

Heating & Cooling

Central air: Yes
Air Conditioning: Yes
Cooling Type: Central Air
Heating Type: Central, Zoned

Structural Information

Architectural Style: Above Flood
Construction: CBS, Combo Construction, Concrete
Square Feet: 6,680
Sq. Ft. Source: Seller
Year Built: 2005

Lot Features

Property View: Open Water View, Bay
Lot Size (Acres): 1.68
Lot Size (Sq. Ft.): 73,190
Lot Dimensions: x
Zoning: RE - Residential Estate

Water Features

Water Front: Yes
Water View: Yes
Water Front Desc.: Bay Front, Gulf Front, Open Water

Financial Considerations

Tax Amount: $65,124
Tax Year: 2025
Terms: Cash, Conventional, VA Loan, FHA

Disclosures and Reports

Legal Description: LTS 6 AND 20 AND PT MARKED RESERVED ADJ TO LT 20 AND PT VACATED AVACADO STREET AND ORANGE STREET TOWNSITE OF ISLAMORADA
Flood Zone: AE, AE, AE, VE, AE
APN: 00402340-000000

Listed by Beycome of Florida, LLC, Steven Koleno (804) 656-5007

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Listing agent

— 20 Avacado St —

Steven Koleno

Beycome of Florida, LLC

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Schools

Schools serving 20 Avacado St

School District:Monroe County School District, Middle Torch Key, FL

Name	Grades	Distance
Plantation Key School 100 Lake Road, Tavernier, FL 33070	PK-8	6.6 mi
Coral Shores High School 89901 Old Highway, Tavernier, FL 33070	9-12	6.9 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20 Avacado St Get Price Alerts and Save Property

Date

Details

Price

Change

Source

2/25/2026

Listed

$15,950,000

80.74%

MLS

4/17/2023

Sold

$8,825,000

—

Public Record

Get Price Alerts and Save Property

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History

Tax History for 20 Avacado St

Year

Property Taxes

Change

Tax Assessment

Change

2024

100%

$7,300,974

—

2024

-100%

$7,304,040

-5%

2023

$63,949

20%

$7,693,438

43%

2021

$53,072

-12%

$5,361,775

-28%

2022

$60,198

13%

$7,435,870

38%

2021

$53,072

9%

$5,386,721

12%

2019

$48,736

6%

$4,791,304

5%

2018

$46,134

4%

$4,549,072

—

2017

$44,269

5%

$4,571,260

15%

2016

$42,222

51%

$3,992,094

51%

2015

$27,954

7%

$2,649,277

9%

2014

$26,025

—

$2,432,199

1%

2013

$26,073

—

$2,412,254

—

View All

Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost

Estimate the Cost for 20 Avacado St

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20 Avacado Street, Upper Sugarloaf Key, FL 33036 (MLS# 618816) is a Single Family property with 6 bedrooms, 7 full bathrooms and 1 partial bathroom. 20 Avacado Street is currently listed for $15,950,000 and was received on February 25, 2026. Want to learn more about 20 Avacado Street? Do you have questions about finding other Single Family real estate for sale in Upper Sugarloaf Key? You can browse all Upper Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.

20 Avacado St Upper Sugarloaf Key, FL 33036