Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$23,500,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 9 Beds
  • 9 Full Baths
  • 2 Partial Baths
  • 7,372 Sq. Ft.
  • Updated 3 days ago
See This Home
Save This Home
See This Home
Save This Home
Rarely do the lines intersect between architectural excellence, positioning, thoughtfulness, and elite water access, until now. Set on a private street in downtown Islamorada, this gated bayfront property includes a main house, guest house, sunset views, and 170 feet of dockage. Built above flood, the main house offers 6 bedrooms, 6 bathrooms, 2 half baths, and an office. A pivot front door opens to living spaces overlooking the bay. The formal dining room includes a wet bar and wine cellar, while the kitchen's double islands provide room for preparing meals and gathering. A water vapor fireplace anchors the living room, and ceilings open to the second floor above both the living room and kitchen. A floating staircase and elevator connect the two levels. Two primary suites, one on each floor, offer a choice of setting. Both feature freestanding soaking tubs and bay-facing windows that turn opaque at the touch of a button. A powder room serves the main living area, and a cabana bath is located by the pool. Outside, the infinity pool's swim-up bar and submerged seating meet the outdoor kitchen counter. The gazebo is equipped with roll-down hurricane shades. Along the waterfront, a 70-foot concrete jetty shelters the basin around the beach. An additional 100-foot wood dock provides two boatlifts (30,000 lb & 10,000 lb) and space for visiting boats. Across the front courtyard, the guest house offers independent living space, including 3 bedrooms and 2 bathrooms upstairs. Three air-conditioned garage bays occupy the ground floor. Tropical landscaping chosen for the Keys climate keeps upkeep manageable. A 100 kW standby propane generator serves the entire property, and an organic mosquito misting system helps make the grounds more comfortable. Years of planning and construction come together in a property designed for life on the bay, from everyday living to time spent on the water.

Full Property Details for 16 Avacado St

General

  • Price: $23,500,000
  • Taxes: $44,526 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 621766
  • Updated: 10/23/2026
  • Added to Site: 4 day(s) ago

Interior

  • Interior Features: Walk-in Closet(s), Bar, Built-in Cabinets, Elevator, Pantry, Quartz Countertops, Security System, Smoke Alarms, Storage, Wet Bar, Whirlpool Bath Tub, Window Treatments
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Freezer, Gas Appliances, Ice Machine, Microwave, Oven, Range, Refrigerator, Washer, Water Purification, Wine Cooler
  • Flooring: Tile

Rooms

Bathrooms

  • Total Bathrooms: 11
  • Full Bathrooms: 9
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 9

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Pool: Yes
  • Pool Description: Concrete, Heated, Salt Water, In Ground
  • Security/Safety: Electric Gate

Exterior

  • Exterior Features: Lighting, Bar, Built-in Grill, Detached Guest Qtrs, Fencing, Gazebo, Hot Tub, Outdoor Kitchen, Outdoor Shower, Privacy Wall/Fence, Sandy Beach, Storage, Water Display
  • Deck/Patio: Screened Patio, Open Porch/Balcony
  • Porch/Patio/Deck: Screened Patio, Open Porch/Balcony

Parking

  • Garage: Yes
  • Parking Features: Covered, Detached

Location

  • Area: 23 - Upper Matecumbe
  • County: Monroe
  • Subdivision: Strattons (82.5)

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: New Construction
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: Drapes/Blinds Incl, Impact Rstnce Doors, Impact Rstnce Window
  • Square Feet: 7,372
  • Sq. Ft. Source: Tax Records
  • Year Built: 2023
  • Property Condition: New Construction

Lot Features

  • Property View: Bay
  • Lot Size (Acres): 0.59
  • Lot Size (Sq. Ft.): 25,771
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Bay Front

Financial Considerations

  • Tax Amount: $44,526.62
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: LT 16 ISLAMORADA PB1-48 UPPER MATECUMBE CO JUDGE GEN PET F-360-361 OR182-461 OR215-381 OR1017-1066 OR1812-536/38 OR1823-
  • APN: 00402290-000000

Listed by Palm House Real Estate, AJ Vetter (305) 304-8841

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 16 Avacado St —

  • AJ Vetter

    Palm House Real Estate

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 16 Avacado St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-86.6 mi
Coral Shores High School
89901 Old Highway, Tavernier, FL 33070
9-127 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 16 Avacado St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
10/23/2026
Listed
$23,500,000
1120.78%
MLS
8/26/2019
Sold
$1,925,000
—
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 for 16 Avacado St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$41,718
—
$5,154,494
—
2024
$41,718
72%
$5,172,037
70%
2023
$24,317
35%
$3,040,926
72%
2021
$18,002
-12%
$1,767,194
-26%
2022
$20,347
13%
$2,395,955
33%
2021
$18,002
20%
$1,806,794
28%
2019
$14,970
7%
$1,416,683
7%
2018
$14,024
5%
$1,328,330
—
2017
$13,404
3%
$1,333,221
10%
2016
$12,977
13%
$1,212,591
15%
2015
$11,494
2%
$1,051,509
3%
2014
$11,293
-2%
$1,021,551
-1%
2013
$11,473
—
$1,028,982
—
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 for 16 Avacado St

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Palm House Real Estate, AJ Vetter (305) 304-8841

Similar Properties near 16 Avacado St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

82768 Overseas Hwy, Islamorada, FL 33036 - Photo 1
$25,000,000

82768 Overseas Hwy  Islamorada, FL 33036

  • Single Family
  • Active
  • 7
    Beds
  • 10
    Total Baths
  • 8,288
    Sq. Ft.
82719 Old Hwy, Islamorada, FL 33036 - Photo 1
$24,995,000

82719 Old Hwy  Islamorada, FL 33036

  • Single Family
  • Active
  • 7
    Beds
  • 11
    Total Baths
  • 10,182
    Sq. Ft.
Listed by Pamela DiMartino (305) 807-7089
82719 Old Hwy, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1
$24,995,000

82719 Old Hwy  Upper Matecumbe Key Islamorada, FL 33036

  • Single Family
  • Active
  • Updated 3 days ago
  • 7
    Beds
  • 11
    Total Baths
  • 10,182
    Sq. Ft.
Listed by Pamela DiMartino (305) 807-7089 and Chateau International Properties, Elba Margarita Franco
81486 Overseas Hwy, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1
$22,500,000

81486 Overseas Hwy  Upper Matecumbe Key Islamorada, FL 33036

  • Single Family
  • Active
  • Updated 3 days ago
  • 7
    Beds
  • 9
    Total Baths
  • 8,878
    Sq. Ft.
Listed by American Caribbean Real Estate, Christie's International Real Estate, KELLY K SHAW PA and American Caribbean Real Estate, Christie's International Real Estate, Joy C Martin

Just Listed near 16 Avacado St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

88540 Overseas Hwy, Plantation Key, FL 33070 - Photo 1 Just Listed
$1,525,000

88540 Overseas Hwy  #719  Plantation Key, FL 33070

  • Townhouse
  • Active
  • Updated 2 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,298
    Sq. Ft.
Listed by Compass Florida LLC - Tavernier, STEVEN J CONLEY, LLC and Compass Florida LLC - Tavernier, Clayton J. Conley
0 High Point Rd, Plantation Key, FL 33070 - Photo 1 Just Listed
$400,000

0 High Point Rd  Plantation Key, FL 33070

  • Lots/Land
  • Active
  • Updated 5 days ago
  • 0.33
    Acres
Listed by Ocean Sotheby's International Realty, Annie Hagen and Ocean Sotheby's International Realty, Leslie Leopold
88540 Overseas Hwy, Plantation Key, FL 33070 - Photo 1 Just Listed
$1,525,000

88540 Overseas Hwy  #UNIT 721  Plantation Key, FL 33070

  • Townhouse
  • Active
  • Updated 2 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,298
    Sq. Ft.
Listed by Compass Florida LLC - Tavernier, STEVEN J CONLEY, LLC and Compass Florida LLC - Tavernier, Clayton J. Conley
94220 Overseas Hwy, Tavernier, FL 33070 - Photo 1 Just Listed
$1,399,000

94220 Overseas Hwy  #1D  Tavernier, FL 33070

  • Condo
  • Active
  • Updated 14 hours ago
  • 2
    Beds
  • 3
    Total Baths
  • 1,523
    Sq. Ft.

Price Reduced near 16 Avacado St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

81801 Overseas Hwy Hwy, Islamorada, FL 33036 - Photo 1 Price Reduced
-$11,000 (-1.55%)
$699,000

81801 Overseas Hwy Hwy  #714  Islamorada, FL 33036

  • Condo
  • Active
  • Updated 6 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 550
    Sq. Ft.
74560 Overseas Hwy, Islamorada, FL 33036 - Photo 1 Price Reduced
-$50,000 (-1.59%)
$3,100,000

74560 Overseas Hwy  Islamorada, FL 33036

  • Retail
  • Active
87429 Old Hwy, Islamorada, FL 33036 - Photo 1 Price Reduced
-$500,000 (-2.63%)
$18,499,000

87429 Old Hwy  Islamorada, FL 33036

  • Single Family
  • Active
  • Updated 4 days ago
  • 6
    Beds
  • 8
    Total Baths
  • 6,692
    Sq. Ft.
149 Pueblo St, Plantation Key, FL 33070 - Photo 1 Price Reduced
-$49,000 (-6.13%)
$750,000

149 Pueblo St  Plantation Key, FL 33070

  • Single Family
  • Active
  • Updated 5 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,176
    Sq. Ft.
Listed by Real Estate Sales Force, Inc., BJ Born and Real Estate Sales Force, Inc., Jamie Gunthner

Recent Sales near 16 Avacado St

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

90400 Overseas Hwy, Plantation Key, FL 33070 - Photo 1 Sold
$23,500,000

90400 Overseas Hwy  Plantation Key, FL 33070

  • Commercial
  • Closed
Listed and Sold by LoKation Real Estate, Kimberly Gray, P.A.

16 Avacado Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 621766) is a Single Family property with 9 bedrooms, 9 full bathrooms and 2 partial bathrooms. 16 Avacado Street is currently listed for $23,500,000 and was received on October 23, 2026. Want to learn more about 16 Avacado Street? Do you have questions about finding other Single Family real estate for sale in Upper Matecumbe Key Islamorada? You can browse all Upper Matecumbe Key Islamorada real estate or contact a Coldwell Banker agent to request more information.

Tour this property