OFF MARKET

Off market feb 2024 for $3.5M

$3,131,180

Est. refi paymentEst. refi $25,989/mo

•

4,404

sq ft

20 Hilton Haven Rd, Key West, FL 33040

About this home

A WATERFRONT LARGE SINGLE FAMILY ESTATE OR LEGAL QUADPLEX IN KEY WEST!! Welcome to 20 Hilton Haven Rd! A neighborhood hidden and tucked away but yet close to it all! An Exceptional and Rare, large waterfront property on Garrison Bight in Key West! This unique and incomparable property contains 4 beautiful living units on a 13,750sf lot, designed by renowned Key West architect, Tom Pope, in the carefree style of Old Town Key West architecture. Delight in lush landscaping, gentle breezes and stunning views of the Gulf of Mexico on the north and Garrison Bight on the south from any of the 13 decks and porches and nearly all the windows. 97 ft concrete seawall for fishing, your boats and toys. Enjoy the large 38x10 concrete deep pool and whirlpool, or relax in the fabulous porch swing! 3 or 4 boat slips, 9 outdoor parking spaces, 2 garage spaces and beautifully landscaped grounds which are perfect for large outdoor parties or high-ground parking, Plenty of room for friends and family! Or use as a single family home offering endless space for a large family on this Spectacular Estate! 1. Main House, Updated beautiful kitchen, dining room, 2 story ceiling and gorgeous water views, large 2nd floor master bedroom and bath, 1st floor guest room, bath, half bath and bar with sink on large screened porch, outdoor shower on the spacious pool deck. All with stunning views and porches or decks outside every door! 2. Main House 3rd Floor Apartment: 1 bedroom, 1 bath, kitchen, living/dining room, two 3rd floor decks with some of the best views in Key West, outside and lockable interior entrances. 3. Main House Pool Apartment: Attached to, but not accessible from main house, 1 bedroom, 1 loft bedroom, 1 bath, 2 story living room with open kitchen, porch with views of both the bight and the gulf! 4. Caretaker's Cottage: 1 bedroom, 1 loft bedroom, full bath, kitchen, living/dining room, large porch, 2 car garage. Magical And Truly A One of a Kind Property

Single-familyProperty Type

1990Year Built

0.32 acresLot Size

$711Est. Price/Sq.Ft.

1 garage spacesParking

Listed by Stacey Pillari • Berkshire Hathaway HomeServices Knight & Gardner Realty

Bought with Vic Musmanno • Coldwell Banker Schmitt Real Estate Co. (KW)

Redfin checked: a few seconds ago

•Source:FLKMLS #607143

Redfin Estimate

$3,131,180

$369K since sold in February 2024$2,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 71.8% higher than the average sale price ($1.82M) of 6 comparable homes.

SOLD AUG 27, 2026
$1,100,000
A
4 beds3 baths2,664 sq ft
1409 4Th St, Key West, FL 33040
SOLD MAY 26, 2026
$2,680,000
B
4 beds3.5 baths3,656 sq ft
1610 Von Phister St, Key West, FL 33040
SOLD SEP 16, 2026
$1,007,000
C
7 beds4 baths2,699 sq ft
1614 Dennis St, Key West, FL 33040
SOLD JAN 29, 2026
$2,800,000
D
5 beds4 baths3,255 sq ft
1400 1st St, Key West, FL 33040
SOLD JUN 10, 2026
$1,385,000
E
3 beds3.5 baths2,236 sq ft
1230 5th St, Key West, FL 33040
SOLD SEP 10, 2026
$1,965,000
F
3 beds3 baths1,938 sq ft
1706 Seminary St, Key West, FL 33040

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Earn from this home

Refinance

Est. cash available

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Market trends in 33040, FL

Last updated October 2026

Buyer's Market

Seller's Market

Buyer's market

Sale-to-list price

94.0%

0.4% MoM

Median sale price

$1.0M

$33K MoM

Avg. days on market

136d

1 days MoM

Recently sold homes

13 MoM

New listings for sale

NEW 30 MINS AGO
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NEW 26 HRS AGO
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NEW 26 HRS AGO
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NEW 27 HRS AGO
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OPEN SAT, 11AM TO 1PM
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NEW 30 HRS AGO
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NEW 31 HRS AGO
$873,000
3 beds2 baths1,056 sq ft
157 Mars Ln, Key West, FL 33040
NEW 31 HRS AGO
$769,000
3 beds2 baths1,221 sq ft
2601 S Roosevelt Blvd Unit 223C, Key West, FL 33040
See all

Provided by Redfin

Sale history for 20 Hilton Haven Rd

Tax history for 20 Hilton Haven Rd

*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

2,439 Sq. Ft.

Year renovated

1997

Sq. Ft.

940

Year built

1993

Style

Multi-Family (2-4 Unit)

County

Monroe County

APN

3267 25 00002190000000

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Oct 9, 2026.

MDR

Medium Density Residential District

The medium density residential district MDR is established to implement comprehensive plan policies for areas designated MDR on the comprehensive plan future land use map. The MDR district shall provide sufficient land area for medium density residential development adequately supported by public services and facilities and compatible with existing and anticipated future land uses. The MDR district shall accommodate a mixture of single-family and multiple-family structure types. Supportive community facilities and accessory land uses may be located within areas designated MDR. This district shall not accommodate transient lodging and guesthomes, commercial uses or freestanding office buildings. However, accessory uses, including approved home occupations, conducted within the residential structures are permitted so long as all such accessory uses are customarily incidental to and subordinate to the residential use. Other customary accessory uses and community facilities may also be located in areas designated MDR.; Review of specific densities of developments shall be directed toward preserving stability of established residential areas. Sites for medium density residential developments should be located so that they provide a smooth transition between lower density residential areas and areas developed and/or designated for other more intense uses. Generally, medium density areas should be located between the perimeter of low density residential areas and areas of high density residential concentrations or other less restrictive uses.

Permitted uses

Include but are not limited to:

Housing-Group
Housing-Single unit
Housing-Multiple units

Property details

Parking

Parking / Garage Information
Vehicle Storage: Attached, Trailer Storage, Off Street Parking, Garage, Guest Parking, Covered Parking
Vehicle Storage: Car(s): 4+

Interior

Interior Features
Interior Features: Built-in Cabinets, Window Treatments, Quartz Countertops, Split Bedroom, Smoke Alarms, Foyer, Drapes/Blinds Incl, Cathedral Ceilings
Flooring: Carpet, Wood Floor, Tile Floor, Combo
Windows/Doors: French Doors, Sliding Glass Doors, Wood Windows, Glass Doors
Heating: Central
Cooling/Heating: Ceiling Fans, Window/Wall Unit, Central A/C
Appliances: Dishwasher, Washer, Stainless Steel Appl, Range, Refrigerator, Oven, Microwave, Dryer
Furnished: Furniture Negotiable

Bathroom Information
# of Full Baths: 5
# of Half Baths: 1

Specialty Room Information
Specialty Rooms: Loft, Other

Multi-Unit Information
# of Total Units: 4

Exterior

Boat Slip/Dock Information
Dockage: Dock Length: 97
Dockage: Seawall: Concrete
Dockage: Boat Lift, Davits
Dockage: Dock: Concrete

Exterior Features
Exterior Features: Detached Guest Qtrs, Storage, Shed, Privacy Wall/Fence, Gutters, Outdoor Shower, Fencing, Landscape Lighting, Fruit Tree(s)
Has Pool
Pool Information: Concrete, Lap, In Ground, Decked
Pool Information: Dimensions: 38 x 10
Pool Info: Other: Hot tub
Porch/Balcony: Deck, Screened Patio, Patio, Open Porch/Balcony
Shutters: Accordion, Roll Down Electric, Panel, Other

Property Features
On Waterfront
Waterfront Type: Bay Front, Open Water
Waterview: Bay/Gulf View, Harbor/Marina View, Open Water View, Ocean View

Property Information
Deed Restrictions: Unknown
Pets: Pets Allowed
Rentals Allowed: With Restrictions
Min Rental Days: 28

Lot Information
Acres: 0.37
Zoning: SF - Single Family
Land Size: 1/4 - 1/2 Acre
Control Depth: 3
Flood Zone: AE, AE

Building Information
Year Built: 1,990
Sq. Ft. Source: Appraisal
Sq. Ft. Remarks: Main house plus 3rd floor apt and pool apt 3,280 plus loft 260, total 3,540 Guest cottage 576 plus loft 288, total 864
Building Style: Other Bldg Style
Building Style: Stories: 3
Building Style: Above Flood: Yes
Construction: Frame, Hardi Board Siding
Roof: Metal Roof

Subdivision/Neighborhood
Subdivision: Hilton Haven Sec 2 A (2.0)
Key West Neighborhood: New Town
Marathon Neighborhood: N/A

Financial

Tax Information
Taxes: $11,895.70
Tax Year: 2,022
Tax Exemptions: Homestead

Financial Information
Terms: Cash, VA, Conventional

Utilities

Utility Information
Utilities: Elect Separate Meter, Water Separate Meter, Whole House Generatr, FKAA, Municipal Sewer
Pre-Wired: Cable
Has Public Sewer Hook-up

Location

Homeowners Association Information
Association Info: 1st Right of Refusal: No
Association Info: Association Fee $: 0.00
Fee Includes: None

Location Information
Side: Bay/Gulf
Mile Marker: 2.00
Directions: US 1 Overseas Hwy to Key West, N Roosevelt Blvd, Right onto Hilton Haven Rd near the Key West Yacht Club and Garrison Bight, house towards end of road of left.

Neighborhood Features
Other Area Features

Public facts

Beds: 2
Baths: 1.0
Sq. Ft.: 940
Stories: 3.0
Lot Size: 2,439 square feet
Style: Multi-Family (2-4 Unit)
Year Built: 1993
Year Renovated: 1997
County: Monroe County
APN: 3267 25 00002190000000

Home facts updated by county records on Oct 9, 2026

Around this home

Schools

K - 12
Preschool & daycare

Horace O'bryant School

Public PreK-8 • Assigned • 0.5mi

3/10

Key West High School

Public 9-12 • Assigned • 0.7mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

6/10 Flood Factor

Estimated 71-79% chance 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

$2.98M – $3.60M

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

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Home values near 20 Hilton Haven Rd

Data from public records.

Address	Redfin Estimate
30 Hilton Haven Rd Apartment 2A, Key West, FL 2 Beds \| 2 Baths \| 1136 Sq. Ft.	$784,587
30 Hilton Haven Rd Apartment 2B, Key West, FL 2 Beds \| 2 Baths \| 1045 Sq. Ft.	$924,213
19 Hilton Haven Rd, Key West, FL 2 Beds \| 1 Baths \| 1395 Sq. Ft.	$2,666,196
30 Hilton Haven Rd Apartment 2C, Key West, FL 3 Beds \| 2 Baths \| 2439 Sq. Ft.	$1,967,387
16 Hilton Haven Rd Apartment 102, Key West, FL 5 Beds \| 4.5 Baths \| 3448 Sq. Ft.	$2,397,220
30 Hilton Haven Rd Apartment 6, Key West, FL 2 Beds \| 2 Baths \| 1045 Sq. Ft.	$837,902
77 Hilton Haven Rd Apartment 11, Key West, FL 2 Beds \| 2.5 Baths \| 1275 Sq. Ft.	$918,255

Address	Redfin Estimate
30 Hilton Haven Rd Apartment 1B, Key West, FL 2 Beds \| 2 Baths \| 1045 Sq. Ft.	$811,622
22 Hilton Haven Rd, Key West, FL 5 Beds \| 6.5 Baths \| 5898 Sq. Ft.	$4,394,392
18 Hilton Haven Rd, Key West, FL 5 Beds \| 5 Baths \| 3597 Sq. Ft.	$4,865,950
30 Hilton Haven Rd Apartment 1A, Key West, FL 2 Beds \| 2 Baths \| 1136 Sq. Ft.	$866,413
24 Hilton Haven Rd, Key West, FL 5 Beds \| 3 Baths \| 2947 Sq. Ft.	$3,350,782
30 Hilton Haven Rd Apartment 5, Key West, FL 2 Beds \| 2 Baths \| 1045 Sq. Ft.	$909,078
30 Hilton Haven Rd, Key West, FL 2 Beds \| 2 Baths \| 1136 Sq. Ft.	$1,243,935

Address	Redfin Estimate
30 Hilton Haven Rd Apartment 3B, Key West, FL 2 Beds \| 2 Baths \| 1045 Sq. Ft.	$1,009,865
30 Hilton Haven Rd Apartment 3, Key West, FL 2 Beds \| 2 Baths \| 1136 Sq. Ft.	$851,830
30 Hilton Haven Rd Apartment 1C, Key West, FL 3 Beds \| 2 Baths \| 1320 Sq. Ft.	$1,039,095
25 Hilton Haven Rd, Key West, FL 2 Beds \| 2 Baths \| 2220 Sq. Ft.	$2,277,110
30 Hilton Haven Rd Apartment 1, Key West, FL 2 Beds \| 2 Baths \| 1136 Sq. Ft.	$683,275
30 Hilton Haven Rd Apartment 7, Key West, FL 3 Beds \| 3 Baths \| 3000 Sq. Ft.	$1,673,292
16 Hilton Haven Rd, Key West, FL 2 Beds \| 2 Baths \| 1043 Sq. Ft.	$834,592

Property information provided by FLKMLS when last listed in 2023. 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 20 Hilton Haven Rd

Tax history for 20 Hilton Haven Rd

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 20 Hilton Haven Rd

More real estate resources