18 Hilton Haven Road, Key West, FL 33040

New Listing

$5,195,000

Rear Deck facing the Yacht Club and Garrison Bight

Second Floor Setting Area with access to Deck

Second Floor Deck with Entrance to Study/Bedroom

View from Window looking North and Water Lot.

Property Type: Residential Bedrooms: 5 Baths: 6 Square Footage: 3,597 Lot Size (sq. ft.): 8,410 Status: Active

Current Price: $5,195,000 List Date: 10/20/2026 Last Modified: 10/20/2026

Overview

Description

Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and ... (Read more)

Listing Details MLS# 621709

Location, Tax & Legal

Street #: 18
Street Name: Hilton Haven
Street Suffix: Road
Key/Island: Key West
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Hilton Haven Sec 2 A (2.0)
Area: 03 - Key West
KW Neighborhood: Midtown East
City: KEY WEST
Mile Marker: 2
Marathon Neighborhood: N/A
Side: Bay/Gulf
Flood Zone: AE
Alternate Key #: 1002283
Add'l Parcel #1: 00001900-000000
Parcel #: 00002160-000000
Zoning: SF - Single Family
Deed Restrictions: Unknown
Legal: AMENDED PLAT OF HILTON HAVEN SEC 2 A SUBDIVISION ON THE ISLAND OF KEY WEST FLA PB2-138 THE W'LY 30 FT OF TR 17 & THE EAS
Taxes: 11987.28
Tax Year: 2026
Pub Sewer HkUp: Yes

Contract Information

Listing Board: Key West Association

General Property Description

Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 3
Pool: Yes
Year Built: 1967
Lot SqFt: 8410
Acres: 0.31
Living Apx SqFt: 3597
SqFt Source: Tax Records
Total Bedrooms: 5
Full Baths: 4
Half Baths: 2
Total Baths: 6
Rentals Allowed: With Restrictions
Min Rental Days: 28
Total Units: 0

Association Info

Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0

Dockage

Dock: Other
Boat Lift: Yes

More Information

Building Style

Above Flood: Unknown
Stories: 2 Stories

Appliances

Other: Electric Cook top
Dryer: Yes
Microwave: Yes
Oven: Yes
Refrigerator: Yes
Stainless Steel Appliance(s): Yes
Washer: Yes

Pool Info

Heated: Yes
Dimensions: 15 X 20
In Ground: Yes
Concrete: Yes

Remarks & Misc

Remarks – Consumer: Double waterfront MM 2 in Key West. Presenting a rare opportunity to acquire a distinguished single-family waterfront home on highly desired Hilton Haven Drive, a truly unique private Key West Street with everything from a luxury resort and high-end properties to houseboats. This spectacular residence is a true gem facing both South and North. On the south side, enjoy sweeping decks, a waterfront pool, 15,000 lb. boat lift and convenient dock overlooking the Key West Yacht Club and Garrison Bight. On the north side, enjoy unencumbered views from the serene, covered entry porch of the Gulf of Mexico with a deeded 75' by 300' bay bottom parcel. Upon entering through the handsome oversized wooden doors, you are greeted by the living room's custom hand built beamed wood cathedral ceiling and a majestic staircase. The sunroom features French doors that open to views of the pool and harbor. The expansive backyard includes a covered dining area, a 45' waterfront deck overlooking the dock and boat lift. The chef's kitchen is designed for entertaining, equipped with ample counter space, Viking appliances, and a Fisher Paykel cooktop. The first-floor primary suite opens to a rear private deck and dock. Completing the first floor is the laundry room, half-bath, full bath, and a charming guest bedroom. The sunroom with wet bar and bathroom provides access to the one car garage, and second staircase leading to the second floor office with custom wood paneling, cabinetry, a full bath and deck with views of the Florida Bay and Garrison Bight. The second floor provides a bonus game room and hosts two additional bedrooms connected by a beautiful bathroom. Throughout this meticulously renovated residence, the present owner has incorporated vaulted ceilings on all levels, custom woodwork, and built-ins, creating a truly spectacular living space. The property must be seen to truly appreciate it. https://show.tours/e/4vNFpvG

Fee Includes

None: Yes

Tax Exemptions

Homestead: Yes

Pets

Pets Allowed: Yes

Cooling

Ceiling Fans(s): Yes
Central Air: Yes
Ductless: Yes

Waterfront

Bay Front: Yes
Gulf Front: Yes
Open Water: Yes

Waterview

Bay/Gulf View: Yes
Harbor/Marina View: Yes
Open Water View: Yes

Floor

Tile: Yes
Wood: Yes

Neighborhood Feature

Fire Hydrant: Yes

Interior Features

Built-in Cabinets: Yes
Cathedral Ceilings: Yes
Granite Counter Top: Yes
Storage: Yes
Walk-in Closet(s): Yes

Property Condition

Updated/Remodeled: Yes

Vehicle Storage

Garage: Yes
Off Street Parking: Yes

Construction

CBS: Yes
Combo Construction: Yes
Concrete: Yes
Frame: Yes

Land Size

1/4 - 1/2 Acre: Yes

Furnished

Negotiable: Yes

Utilities

FKAA: Yes
Municipal Sewer: Yes

Porch/Balcony

Deck: Yes
Open Porch/Balcony: Yes

Title

Negotiable: Yes

Roof

Metal Roof: Yes

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: Bay Front; Gulf Front; Open Water Waterview: Bay/Gulf View; Harbor/Marina View; Open Water View Dockage: Boat Lift Property Condition: Updated/Remodeled Vehicle Storage: Garage; Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air; Ductless Utilities: FKAA; Municipal Sewer Interior Features: Built-in Cabinets; Cathedral Ceilings; Granite Counter Top; Storage; Walk-in Closet(s) Appliances: Dryer; Microwave; Oven; Refrigerator; Stainless Steel Appliance(s); Washer Pool Info: In Ground; Concrete Construction: CBS; Combo Construction; Concrete; Frame Floor: Tile; Wood Roof: Metal Roof Pets: Pets Allowed Neighborhood Feature: Fire Hydrant Land Size: 1/4 - 1/2 Acre Title: Negotiable

Documents

Flood Disclosure ›

Listing Office: Keller Williams Key West Compass Realty

Last Updated: October - 20 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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