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18 Hilton Haven Road, Key West, FL 33040

$5,395,000
Property Type: Residential Bedrooms: 5 Baths: 6 Square Footage: 3,597 Lot Size (sq. ft.): 8,410 Status: Active
Current Price: $5,395,000 List Date: 10/16/2025 Last Modified: 12/16/2025

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 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. Pictures do not do it justice. The property must be seen to truly appreciate it. https://show.tours/e/4vNFpvG

More Information MLS# 616896

Contract Information

Listing Board: Key West Association Current Price: $5,395,000 Listing Date: 2025-10-16 List Price: $5,395,000

Location, Tax & Legal

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 EA Taxes: 11964.81 Tax Year: 2024 Pub Sewer HkUp: Yes 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

General Property Description

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

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. Pictures do not do it justice. The property must be seen to truly appreciate it. https://show.tours/e/4vNFpvG

Association Info

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

Fee Includes

None: 1

Dockage

Dock: Other Boat Lift: 1

Tax Exemptions

Homestead: 1

Appliances

Dryer: 1 Microwave: 1 Oven: 1 Refrigerator: 1 Stainless Steel Appliance(s): 1 Washer: 1 Other: Electric Cook top

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1 Ductless: 1

Waterfront

Bay Front: 1 Open Water: 1

Waterview

Bay/Gulf View: 1 Harbor/Marina View: 1 Open Water View: 1

Floor

Tile: 1 Wood: 1

Neighborhood Feature

Fire Hydrant: 1

Interior Features

Built-in Cabinets: 1 Cathedral Ceilings: 1 Granite Counter Top: 1 Storage: 1 Walk-in Closet(s): 1

Property Condition

Updated/Remodeled: 1

Building Style

Above Flood: Unknown Stories: 2 Stories

Vehicle Storage

Garage: 1 Off Street Parking: 1

Construction

CBS: 1 Combo Construction: 1 Concrete: 1 Frame: 1

Land Size

1/4 - 1/2 Acre: 1

Furnished

Negotiable: 1

Utilities

FKAA: 1 Municipal Sewer: 1

Porch/Balcony

Deck: 1 Open Porch/Balcony: 1

Title

Negotiable: 1

Pool Info

In Ground: 1 Heated: Yes Concrete: 1 Dimensions: 15 X 20

Roof

Metal Roof: 1

Status Change Info

Status: Active

Property Features

Fee Includes: None Tax Exemptions: Homestead Waterfront: Bay 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
Listing Office: Keller Williams Key West Compass Realty
Last Updated: December - 16 - 2025
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.