18 Hilton Haven Road, Key West, FL 33040

$5,195,000
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: 10/16/2025 Last Modified: 2/16/2026

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. The property must be seen to truly appreciate it. https://show.tours/e/4vNFpvG

More Information MLS# 616896

Contract Information

Current Price: $5,195,000 Listing Date: 2025-10-16 Listing Board: Key West Association List Price: $5,195,000

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

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

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Dockage

Dock: Other

Building Style

Above Flood: Unknown Stories: 2 Stories

Appliances

Other: Electric Cook top

Pool Info

Heated: Yes Dimensions: 15 X 20

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: February - 16 - 2026
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