For sale

$15,950,000

20 Avacado St, Islamorada, FL 33036

6beds

6,680sqft

$97,468/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

172 days

552

12

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	Price change	$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