$22,000,100
SOLD MAR 17, 2026

19 Sunset Key Dr Key West, FL 33040

4 Beds
6 Baths
6,532 Sq Ft
0.68 Acres Lot

Sale Details

Date Sold: March 17, 2026

$3,368 Per Sq Ft

8% Below List Price

2 Days on Market

Highlights

  • Ocean Front
  • Beach
  • Tennis Courts
  • Dock Facilities
  • Detached Guest House
  • Heated In Ground Pool

About This Home

As of March 2026

A truly one-of-one legacy estate set on Sunset Key, one of the most coveted and private islands in the Florida Keys. Just minutes by boat from Key West, this extraordinary waterfront residence offers unmatched privacy, scale, and architectural distinction.Positioned on nearly an acre and the largest homesite on the island, this classically inspired estate was designed by a renowned Naples-based architect in a modified Bermuda style. Timeless in design and rich in detail, the home reflects exceptional craftsmanship throughout.The main residence features soaring ceilings with intricate custom moldings, marble and hardwood floors, and a magnificent great room with expansive glass doors opening to a wraparound lanai, creating seamless indoor-outdoor living with sweeping sunset and open-water views. The home offers three bedrooms, three full baths, and two half baths, complemented by a detached one-bedroom, one-bath guest house.Designed for both grand entertaining and everyday living, the estate flows effortlessly between interior and exterior spaces. Highlights include a grand entertainer's kitchen with oversized island seating and bespoke cabinetry, a custom wet bar with glass-front cabinetry and stone counters, multiple indoor sitting and lounge areas, a garage and a gated entry with circular brick drive.Outdoor living is elevated by expansive covered verandas, sun terraces, and a resort-style pool and spa adorned with custom mosaic artwork, an unforgettable setting for incredible sunsets, intimate gatherings, or live music under the stars. From nearly every vantage point, enjoy ever-changing water views with passing cruise ships, yachts, fishing boats, and frequent dolphin sightings.Sunset Key residents enjoy private beaches, a fitness center, spa, tennis courts, the acclaimed Latitudes restaurant, and a full suite of resort-style amenities.A rare opportunity to own one of the most distinctive properties ever offered in the Florida Keys.

Last Agent to Sell the Property

Pierre Bellion

Ocean Sotheby's International Realty License #3301978 Listed on: 02/03/2026

Ocean Sotheby's International Realty

Co-Listed By

Jenna Stauffer

Berkshire Hathaway HomeServices Knight & Gardner Realty

Last Buyer's Agent

Pierre Bellion

Ocean Sotheby's International Realty License #3301978 Listed on: 02/03/2026

Ocean Sotheby's International Realty

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $42,777

Year Built

  • Built in 2000

Lot Details

  • 29,490 Sq Ft Lot
  • Ocean Front
  • Privacy Fence

HOA Fees

  • $4,912 Monthly HOA Fees

Home Design

  • Metal Roof
  • Pre-Cast Concrete Construction

Interior Spaces

  • 6,532 Sq Ft Home
  • Wet Bar
  • Bar
  • Fireplace
  • Storage
  • Home Gym
  • Ocean Views

Kitchen

  • Oven
  • Range
  • Microwave
  • Freezer
  • Ice Maker
  • Dishwasher
  • Stainless Steel Appliances
  • Disposal

Flooring

  • Wood
  • Marble

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Walk-In Closet
  • Whirlpool Bathtub

Laundry

  • Laundry Room
  • Dryer
  • Washer

Parking

  • Garage
  • Electric Gate

Pool

  • Heated In Ground Pool
  • Outdoor Shower

Outdoor Features

  • Dock Facilities
  • Tennis Courts
  • Outdoor Kitchen
  • Lanai
  • Outdoor Storage

Utilities

  • Whole House Permanent Generator
  • Public Hookup Available For Sewer
  • Cable TV Available

Additional Features

  • Detached Guest House
  • Island Location

Listing and Financial Details

  • Homestead Exemption
  • Assessor Parcel Number 00000200-000519

Community Details

Overview

  • Association fees include common area mnt
  • Sunset Key Island Unrcd Subdivision
  • Rental Restrictions

Recreation

  • Beach
  • Tennis Courts
  • Community Pool
  • Community Spa

Home Details

Home Type

Single Family

Est. Annual Taxes

$42,777

Year Built

Built in 2000

Lot Details

0.68 Acres

HOA Fees

$4,912 per month

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • As Is Right To Inspect: Yes
  • First Right of Refusal: No
  • Association Fee: 14737.00
  • Mandatory HOA: Yes
  • Fee Includes: Common Area Mnt, Other
  • Key Island: Sunset Key
  • K W Neighborhood: Sunset Key
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • M L S Identifier: 20060123165453488875000000
  • Neighborhood Feature: Community Pool, Spa, Other Area Features, Beach, Tennis Courts
  • Off Shore Island: Yes
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Sale Terms: Cash
  • Side: Bay/Gulf
  • State Province: FL
  • Taxes: 42777.30
  • Vehicle Storage: Garage
  • Year Built: 2000
  • Alternate Key Number: 8885237
  • Lot Sq Ft: 29490.00
  • Pool Info: In Ground
  • Pool Info Heated: Yes
  • Association Maintenance Fee Per: Quarterly
  • Species List: No
  • Tax Exemptions: Homestead
  • Building Style Above Flood: Unknown
  • Estimated Living Sq Ft: 6532.00
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Interior Amenities: Wet Bar, Storage, Bar, Other, Whirlpool Bath Tub, Walk-in Closet(s), Pantry, Fireplace(s)
  • Total Bathrooms: 6.00
  • Full Bathrooms: 4
  • Appliances: More Appliances, Stainless Steel Appliance(s), Ice Machine, Gas Appliances, Freezer, Disposal, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer, Washer
  • Floor: Wood, Marble
  • Half Bathrooms: 2
  • Specialty Rooms: Gym, Other, Laundry Room
  • Appliances Other: YES
  • Total Bedrooms: 4

Exterior Features

  • Dockage: Dock Privileges
  • Waterfront: Oceanfront, Open Water
  • Waterfront: Yes
  • Construction: Concrete
  • Exterior Features: Bar, Storage, Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lanai, Detached Guest Qtrs
  • Roof: Metal Roof
  • Waterview: Ocean View, Open Water View
  • Pool: Yes

Utilities

  • Security: Electric Gate, Other
  • Utilities: FKAA, Whole House Generatr, Cable Available, Municipal Sewer

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: AE,AO,0.2 PCT ANNUAL
  • Parcel Number: 00000200-000519
  • Land Size: 1/2 - Less Than 1 AC
  • Acres: 0.68

Rental Info

  • Rentals Allowed: With Restrictions

Tax Info

  • Tax Year: 2025

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
Feb 3, 2026
Closed on
Mar 17, 2026
Sold by
Drettmann Henry and Henry A Drettmann Trust
Bought by
Lauralee V Howley Family Trust and Howley
Seller's Agent
Pierre Bellion
Ocean Sotheby's International Realty
Buyer's Agent
Pierre Bellion
Ocean Sotheby's International Realty
List Price
$23,900,000
Sold Price
$22,000,100
Premium/Discount to List
-$1,899,900
-7.95%
Views
643

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-100.00%

Purchase Details

Closed on
Mar 4, 2019
Sold by
Drettmann Arleen R and Drettmann Henry A
Bought by
Arleen Drettmann Living Trust

Purchase Details

Closed on
Apr 5, 2003
Sold by
Drettmann Henry A and Drettmann Mary A
Bought by
Bampartners Lp

Purchase Details

Closed on
Apr 26, 1996
Sold by
Parcel G Island Development Corp
Bought by
Drettmann Henry A and Drettmann Mary A
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
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Sold Price
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Purchase History

Date Type Sale Price Title Company
Deed $22,000,000 None Listed On Document
Warranty Deed -- None Listed On Document
Warranty Deed -- None Listed On Document
Warranty Deed -- None Listed On Document
Quit Claim Deed -- --
Deed $1,000,000 --
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
03/17/2026 03/17/26 Sold $22,000,100 -7.9% $3,368 / Sq Ft
02/05/2026 02/05/26 Pending -- -- --
02/03/2026 02/03/26 For Sale $23,900,000 -- $3,659 / Sq Ft
Source: Florida Keys Board of REALTORS®

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $41,543 $5,173,775 -- --
2024 $40,939 $5,027,965 -- --
2023 $40,939 $4,881,520 $0 $0
2022 $39,220 $4,739,340 $0 $0
2021 $40,365 $4,601,301 $0 $0
2020 $39,702 $4,537,773 $0 $0
2019 $39,162 $4,435,751 $0 $0
2018 $39,266 $4,353,044 $0 $0
2017 $39,145 $4,263,571 $0 $0
2016 $40,613 $4,178,680 $0 $0
2015 $41,395 $4,149,633 $0 $0
2014 $42,780 $4,116,699 $0 $0
Source: Public Records

Agents Affiliated with this Home

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Map

Source: Florida Keys Board of REALTORS®

MLS Number: 618455

Florida Keys Board of REALTORS®

APN: 00000200-000519

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