OFF MARKET

Off market jul 2021 for $2.2M

$2,872,236

Est. refi paymentEst. refi $17,329/mo

•

1,904

sq ft

44 Sunset Key Dr, Key West, FL 33040

About this home

Here is your opportunity to live at one of Key West's most desirable addresses. 44 Sunset Key Drive is an absolutely handsome, bright and airy home on the private island of Sunset Key. The open floor plan with its multiple french doors opens up to the private pool and several patio areas for effortless entertaining. This home features three bedrooms and three baths that open onto private porches, one of which is on the first floor. There's even covered parking for your golf carts in this car-free oasis. Situated just steps from the private beaches, access to the tennis courts are even closer thru your private gateway. Sunset Key is the ultimate in Luxury living with its white sandy beaches, tennis, spa, waterfront dinning and Bougainvillea laced homes accented with Hibiscus trees. Access is from Historic Old Town via a 24 hour ferry next to Margaritaville that features ample parking. Sunset Key is a 27 acre island located only 3 minutes off Key West and is the ultimate paradise island in paradise.

Single-familyProperty Type

1998Year Built

4,972 sq ftLot Size

$1,509Est. Price/Sq.Ft.

Listed by Mark Grabowski • Berkshire Hathaway HomeServices Knight & Gardner Realty

Bought with Mark Grabowski • Berkshire Hathaway HomeServices Knight & Gardner Realty

Redfin checked: 2 minutes ago

•Source:FLKMLS #585074

Redfin Estimate

$2,872,236

$642K since sold in July 2021$308K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 23.4% lower than the average sale price ($3.75M) of 6 comparable homes.

SOLD JUL 20, 2026
$5,800,000
A
3 beds3 baths1,927 sq ft
293 Sunset Key Dr, Key West, FL 33040
SOLD SEP 16, 2026
$6,600,000
B
3 beds2.5 baths2,528 sq ft
5 Sunset Key Dr, Key West, FL 33040
SOLD SEP 3, 2026
$2,200,000
C
2 beds2.5 baths1,681 sq ft
68 Sunset Key Dr, Key West, FL 33040
SOLD MAY 27, 2026
$3,250,000
D
3 beds3 baths2,188 sq ft
906 Southard St, Key West, FL 33040
SOLD APR 15, 2026
$2,295,000
E
3 beds3 baths1,916 sq ft
312 Margaret St, Key West, FL 33040
SOLD APR 14, 2026
$2,362,000
F
3 beds3 baths1,608 sq ft
506 Emma St, Key West, FL 33040

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Earn from this home

Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$5,778/mo

Redfin rental estimate

List your home for rent

Market trends in 33040, FL

Last updated September 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-List Price

95.5%

0.0% MoM

Median sale price

$997K

$103K MoM

Avg. days on market

141d

11 days MoM

Recently sold homes

116

18 MoM

New listings for sale

NEW 17 HRS AGO
$1,699,000
2 beds2.5 baths1,463 sq ft
615 Amelia St, Key West, FL 33040
NEW 21 HRS AGO
$1,999,999
4 beds3 baths2,342 sq ft
220 Angela St Unit A&B, Key West, FL 33040
NEW 22 HRS AGO
$3,850,000
5 beds3.5 baths2,280 sq ft
415 & 417 Truman Ave, Key West, FL 33040
3D WALKTHROUGH
$1,195,000
3 beds2 baths1,052 sq ft
2911 Seidenberg Ave, Key West, FL 33040
$1,695,000
4 beds4.5 baths2,027 sq ft
5 Hilton Haven Dr, Key West, FL 33040
$1,169,000
2 beds2.5 baths1,124 sq ft
927 Thomas St #1, Key West, FL 33040
$20,000
2 beds2 baths1,400 sq ft
3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040
$59,000
2 beds2 baths1,120 sq ft
617 Front St Unit A52 wk32, Key West, FL 33040
$62,000
2 beds2 baths1,120 sq ft
617 Front St Unit A52 Penthouse WK 52, Key West, FL 33040
3D WALKTHROUGH
$49,900
2 beds2 baths1,120 sq ft
617 Front St Unit E-43 AB Week 46 Lockout, Key West, FL 33040
See all

Provided by Redfin

Sale history for 44 Sunset Key Dr

Date

Event

Price

FLKMLS #585074

Jul 21, 2021

Sold

$2,230,000

$1,171/sq ft

Apr 4, 2019

Listed

$2,300,000

$1,208/sq ft

FLKMLS #578884

May 15, 2020

Listing Removed

—

Feb 22, 2018

Listed

$2,500,000

$1,313/sq ft

FLKMLS #574372

May 15, 2020

Listing Removed

—

Feb 21, 2017

Listed

$2,850,000

$1,497/sq ft

FLKMLS #584425

Apr 1, 2019

Listing Removed

—

Feb 24, 2019

Listed

$2,500,000

$1,313/sq ft

MARMLS #A10229090

Feb 21, 2018

Listing Removed

—

Feb 21, 2017

Listed

$2,850,000

$1,497/sq ft

FLKMLS #117308

Dec 12, 2013

Listing Removed

—

Dec 3, 2012

Listed

$2,650,000

$1,392/sq ft

FLKMLS #115572

Nov 30, 2012

Listing Removed

—

Nov 1, 2011

Listed

$2,650,000

$1,392/sq ft

Public Records

Nov 30, 2001

Sold

$900,000

$473/sq ft

Public Records

Apr 4, 2000

Sold

$900,000

$473/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$26,186 (+10.4%)

2024

$23,710 (−0.6%)

$2,212,540 + $623,264

$2,835,804

2023

$23,854 (+10.5%)

$2,212,540 + $598,433

$2,810,973

2022

$21,582 (+5.6%)

$1,968,912 + $606,012

$2,574,924

2021

$20,430 (+4.6%)

$1,591,040 + $705,805

$2,296,845

2020

$19,534 (−0.5%)

$1,486,628 + $714,342

$2,200,970

2019

$19,628 (+7.8%)

$1,486,628 + $714,342

$2,200,970

2018

$18,207 (+8.1%)

2017

$16,835 (−7.6%)

$1,243,000 + $559,024

$1,802,024

2015

$18,230 (+3.0%)

$1,302,667 + $399,818

$1,702,485

2014

$17,707

Tax history for 44 Sunset Key Dr

Year

Property tax

Land + Additions

Assessment*

2025

$26,186 (+10.4%)

2024

$23,710 (−0.6%)

$2,212,540 + $623,264

$2,835,804

2023

$23,854 (+10.5%)

$2,212,540 + $598,433

$2,810,973

2022

$21,582 (+5.6%)

$1,968,912 + $606,012

$2,574,924

2021

$20,430 (+4.6%)

$1,591,040 + $705,805

$2,296,845

2020

$19,534 (−0.5%)

$1,486,628 + $714,342

$2,200,970

2019

$19,628 (+7.8%)

$1,486,628 + $714,342

$2,200,970

2018

$18,207 (+8.1%)

2017

$16,835 (−7.6%)

$1,243,000 + $559,024

$1,802,024

2015

$18,230 (+3.0%)

$1,302,667 + $399,818

$1,702,485

2014

$17,707

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Zoning
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

4,970 Sq. Ft.

Year renovated

2015

Sq. Ft.

1,904

Year built

1998

Style

Single Family Residential

County

Monroe County

APN

3667 24 00000200000544

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 10, 2026.

HPRD

Historic Planned Redevelopment And Development District

The historic planned redevelopment and development district HPRD is established to implement comprehensive plan policies for areas designated HPRD on the comprehensive plan future land use map. The HPRD district shall provide a management framework for directing future redevelopment in several redeveloping fringe areas within and outside the review area of the historic architectural review commission.; The HPRD district includes the Truman Annex project, including Sunset Island. The HPRD district shall provide a basis for encouraging additional development and redevelopment activities in other areas. Such new development and redevelopment shall be designed to advance the goals, objectives and policies of the comprehensive plan. For instance, the HPRD district shall promote the following: Historic preservation.; Neighborhood facility improvements.; Architectural and urban design amenities which are consistent with the traditional Old Town historic character and which further subarea design and improvement strategies.; An increased supply of affordable housing which is accessible to targeted income groups over a longterm period.; Off-site parking facilities, including parking structures at strategically located areas through contributions to a special parking fund to be established to assist in financing construction of off-site centrally located parking facilities.

Permitted uses

Include but are not limited to:

Housing-Group
Housing-Single unit
Housing-Multiple units
Office

Property details

Parking

Parking / Garage Information
Vehicle Storage: Vehicle Restrictions

Interior

Interior Features
Interior Features: Fire Sprinkler, Walk-in Closet, Window Treatments
Flooring: Marble, Wood Floor
Windows/Doors: French Doors, Single Hung Windows
Cooling/Heating: Ceiling Fans, Heat, Central A/C
Appliances: Dishwasher, Washer, Microwave, Refrigerator, Range, Oven, Dryer
Furnished: Furniture Negotiable

Bathroom Information
# of Full Baths: 3

Specialty Room Information
Specialty Rooms: Laundry Room

Exterior

Boat Slip/Dock Information
Dockage: First Come Dock, Other Dockage

Exterior Features
Exterior Features: Fencing, Shed, Storage, Sprinkler System, Landscape Lighting
Has Pool
Pool Is Heated
Pool Information: Concrete, In Ground
Porch/Balcony: Deck, Patio, Open Porch/Balcony

Security
Patrolled Area

Property Features
Waterfront Type: None
Waterview: Ocean View

Property Information
Deed Restrictions: Unknown
Pets: Pets w/Restrictions: breed, weight, #of
Rentals Allowed: With Restrictions
Min Rental Days: 30

Lot Information
Acres: 0.11
Zoning: SF - Single Family
Land Size: Less Than 1/4 Acre
Control Depth: 20
Flood Zone: 0.2 PCT ANNUAL CHANC

Building Information
Year Built: 1,998
Sq. Ft. Source: Property Data Card
Building Style: Stories: 2
Building Style: Above Flood: Unknown
Construction: Frame
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: Sunset Key (Tank) Island Unrcd (0.0)
Key West Neighborhood: Sunset Key
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $16,529.78
Tax Year: 2,017
Tax Exemptions: None

Utilities

Utility Information
Utilities: FKAA, Municipal Sewer
Has Public Sewer Hook-up

Location

Homeowners Association Information
Mandatory Home Owners Association
Association Info: 1st Right of Refusal: No
Association Info: Association Fee $: 5763.61
Association Info: Association/Maintenance Fee Per: Quarterly
Fee Includes: Common Area Maintenance, Security, Other

Location Information
Side: Bay/Gulf
Mile Marker: 0.00

Neighborhood Features
Beach, Tennis Courts, Other Area Features, Fire Hydrant, Community Dockage

Public facts

Beds: 3
Baths: 3.0
Sq. Ft.: 1,904
Stories: 2.0
Lot Size: 4,970 square feet
Style: Single Family Residential
Year Built: 1998
Year Renovated: 2015
County: Monroe County
APN: 3667 24 00000200000544

Home facts updated by county records on Jul 10, 2026

Around this home

Schools

Horace O'bryant School

Public PreK-8 • Assigned • 1.8mi

3/10

Key West High School

Public 9-12 • Assigned • 2.4mi

4/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

Heat Factor

We're working on getting current and accurate heat risk information for this home.

10/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Key West, FL • 33040

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10.1 hours in June and 7.3 hours in December, placing it above the U.S. average for solar exposure.

10.1 hrs

7.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$2.73M – $3.30M

Sell confidently with a local market expert in Key West. 3 minutes to get started.

Nearby similar homes

$62,000

2 beds2 baths1,120 sq ft

617 Front St Unit A52 Penthouse WK 52, Key West, FL 33040

$59,000

2 beds2 baths1,120 sq ft

617 Front St Unit A52 wk32, Key West, FL 33040

3D WALKTHROUGH

$59,900

2 beds2 baths1,120 sq ft

617 Front St Unit C54 Penthouse Week 36, Key West, FL 33040

3D WALKTHROUGH

$49,900

2 beds2 baths1,120 sq ft

617 Front St Unit E-43 AB Week 46 Lockout, Key West, FL 33040

$55,000

2 beds2 baths1,120 sq ft

617 Front st St Unit C31, week 3, Key West, FL 33040

$42,000

2 beds2 baths1,120 sq ft

617 Front St Unit B41 Week 1, Key West, FL 33040

New listings for sale in 33040

NEW 17 HRS AGO3D WALKTHROUGH

$1,699,000

2 beds2.5 baths1,463 sq ft

615 Amelia St, Key West, FL 33040

NEW 21 HRS AGO

$1,999,999

4 beds3 baths2,342 sq ft

220 Angela St Unit A&B, Key West, FL 33040

NEW 22 HRS AGO

$3,850,000

5 beds3.5 baths2,280 sq ft

415 & 417 Truman Ave, Key West, FL 33040

3D WALKTHROUGH

$1,195,000

3 beds2 baths1,052 sq ft

2911 Seidenberg Ave, Key West, FL 33040

$1,695,000

4 beds4.5 baths2,027 sq ft

5 Hilton Haven Dr, Key West, FL 33040

$1,169,000

2 beds2.5 baths1,124 sq ft

927 Thomas St #1, Key West, FL 33040

$20,000

2 beds2 baths1,400 sq ft

3675 S Roosevelt Blvd Unit week 42, Key West, FL 33040

$59,000

2 beds2 baths1,120 sq ft

617 Front St Unit A52 wk32, Key West, FL 33040

$62,000

2 beds2 baths1,120 sq ft

617 Front St Unit A52 Penthouse WK 52, Key West, FL 33040

Home values near 44 Sunset Key Dr

Data from public records.

Address	Redfin Estimate
13 Sunset Key Dr, Key West, FL 4 Beds \| 4.5 Baths \| 2480 Sq. Ft.	$6,619,727
14 Sunset Key Dr, Key West, FL 3 Beds \| 2.5 Baths \| 3302 Sq. Ft.	$5,319,138

Address	Redfin Estimate
47 Sunset Key Dr, Key West, FL 3 Beds \| 3 Baths \| 1984 Sq. Ft.	$4,083,657
62 Sunset Key Dr, Key West, FL 2 Beds \| 2.5 Baths \| 1681 Sq. Ft.	$2,435,574

Address	Redfin Estimate
10 Sunset Key Dr, Key West, FL 3 Beds \| 4 Baths \| 2513 Sq. Ft.	$8,597,708
411 Sunset Key Dr, Key West, FL 2 Beds \| 2.5 Baths \| 1668 Sq. Ft.	$2,509,538

Property information provided by FLKMLS when last listed in 2019. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 33040, FL

Sale history for 44 Sunset Key Dr

Tax history for 44 Sunset Key Dr

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 33040

Home values near 44 Sunset Key Dr

More real estate resources