For sale

$15,950,000

20 Avacado St, Islamorada, FL 33036

6beds

6,680sqft

$106,036/mo

Get pre-qualified

Single Family Residence

Built in 2005

1.68 Acres Lot

$-- Zestimate^®

$2,388/sqft

$-- HOA

What's special

Coastal eleganceUnobstructed gulf viewsComplete gym

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

218 days
360
7

Facts & features

Interior

Bedrooms & bathrooms

Bedrooms: 6
Bathrooms: 8
Full bathrooms: 7
1/2 bathrooms: 1

Bedroom 1

Level: Main
Area: 306 Square Feet
Dimensions: 18 x 17

Bedroom 1

Level: Second
Area: 224 Square Feet
Dimensions: 14 x 16

Bedroom 2

Level: Main
Area: 255 Square Feet
Dimensions: 17 x 15

Bedroom 2

Level: Second
Area: 238 Square Feet
Dimensions: 17 x 14

Bedroom 3

Level: Second
Area: 483 Square Feet
Dimensions: 23 x 21

Dining room

Level: Main
Area: 255 Square Feet
Dimensions: 17 x 15

Kitchen

Level: Main
Area: 368 Square Feet
Dimensions: 23 x 16

Living room

Level: Main
Area: 324 Square Feet
Dimensions: 18 x 18

Other

Level: Second
Area: 323 Square Feet
Dimensions: 19 x 17

Other

Level: Second
Area: 280 Square Feet
Dimensions: 20 x 14

Heating

Has Heating (Unspecified Type)

Cooling

Central Air

Appliances

Included: More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Oven, Microwave, Disposal, Freezer, Gas Appliances, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)

Interior area

Total structure area: 6,680
Total interior livable area: 6,680 sqft

Property

Features

Has private pool: Yes
Pool features: In Ground, Concrete, Decked
On waterfront: Yes

Lot

Size: 1.68 Acres

Details

Parcel number: 00402340000000
Zoning: RE - Residential Estate

Construction

Type & style

Home type: SingleFamily
Property subtype: Single Family Residence

Materials

CBS, Concrete, Combo Construction

Condition

Year built: 2005

Utilities & green energy

Utilities for property: See Remarks

Community & HOA

Community

Subdivision: Misc Upper Matacumbe (82.0)

HOA

Has HOA: No
Services included: None

Location

Region: Islamorada

Financial & listing details

Price per square foot: $2,388/sqft
Tax assessed value: $7,300,974
Annual tax amount: $65,124
Date on market: 2/25/2026
Listing terms: Cash,Conventional,FHA

Estimated market value

Not available

Estimated sales range

Not available

Price history

Date	Event	Price
2/25/2026	Listed for sale	$15,950,000+80.7%$2,388/sqft
Source: Key West AOR #618816 Report a problem
4/17/2023	Sold	$8,825,000-9.5%$1,321/sqft
Source: FLKMLS #600764 Report a problem
3/10/2023	Contingent	$9,750,000$1,460/sqft
Source: Key West AOR #600764 Report a problem
1/2/2023	Listed for sale	$9,750,000-9.3%$1,460/sqft
Source: Key West AOR #600764 Report a problem
4/28/2022	Listed for sale	$10,750,000+111.3%$1,609/sqft
Source: Key West AOR #600764 Report a problem
5/1/2015	Sold	$5,087,250-14.5%$762/sqft
Source: FLKMLS #566231 Report a problem
2/16/2015	Listed for sale	$5,950,000$891/sqft
Source: Ocean Sotheby's International Realty #566231 Report a problem
1/10/2015	Listing removed	$5,950,000$891/sqft
Source: Ocean Sotheby's International Realty #566231 Report a problem
1/3/2015	Listed for sale	$5,950,000+6.3%$891/sqft
Source: Ocean Sotheby's International Realty #566231 Report a problem
12/2/2014	Listing removed	$5,595,000$838/sqft
Source: Ocean Sotheby's International Realty Report a problem
11/21/2014	Listed for sale	$5,595,000$838/sqft
Source: Ocean Sotheby's International Realty Report a problem

Public tax history

Year	Property taxes	Tax assessment
2025	$66,720 +0.6%	$7,300,974 0%
2024	$66,353 +3.8%	$7,304,040 +12.6%
2023	$63,949 +6.2%	$6,487,748 +10%
2022	$60,198 +13.4%	$5,897,953 +10%
2021	$53,072 +0.5%	$5,361,775 +1.7%
2020	$52,807	$5,270,434 +10%
2019	$52,807 +8.4%	$4,791,304 +5.3%
2018	$48,736 +5.6%	$4,549,072 -0.5%
2017	$46,134 +4.2%	$4,571,260 +14.5%
2016	$44,269 +4.8%	$3,992,094 +50.7%
2015	$42,222	$2,649,277