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For sale
  • Price cut: $100K (2/2)
    $5,195,000

    18 Hilton Haven Rd, Key West, FL 33040

    5beds
    3,597sqft
    : 
    Single Family Residence
    Built in 1967
    0.31 Acres Lot
    $4,686,500 Zestimate®
    $1,444/sqft
    $-- HOA

    What's special

    Waterfront poolOne car garageCharming guest bedroomHandsome oversized wooden doorsMajestic staircaseSweeping decksLaundry room
    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
    164 days
    |
    2,950
    |
    80
    |

    Zillow last checked: 7 hours ago

    Listing updated: February 09, 2026 at 03:02am

    Listed by:

    The Behmke Group 305-304-0999,

    Keller Williams Key West Compass Realty,

    Stephen M Andres 814-397-4775,

    Keller Williams Key West Compass Realty

    Source: FLKMLS,MLS#: 616896MLS LogoOriginating MLS: Key West Association

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 5
      • Bathrooms: 6
      • Full bathrooms: 4
      • 1/2 bathrooms: 2
      Cooling
      • Central Air, Ductless, Ceiling Fans(s)
      Appliances
      • Included: Washer, Stainless Steel Appliance(s), Microwave, Oven, Refrigerator, Dryer, Electric Cook top
      Features
      • Cathedral Ceiling(s), Walk-In Closet(s), Storage, Granite Counters, Built-in Cabinets
      • Flooring: Tile, Wood
      Interior area
      • Total interior livable area: 3,597 sqft

      Property

      Parking
      • Parking features: Garage, Off Street
      • Has garage: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Open Porch/Balcony, Deck
      • Has private pool: Yes
      • Pool features: Heated, In Ground, Concrete
      • Has view: Yes
      • View description: Bay/Gulf View, Harbor/Marina View, Water
      • Has water view: Yes
      • Water view: Bay/Gulf View,Harbor/Marina View,Water
      • Waterfront features: Bay Front, Open Water, Waterfront, Dock: Other, Dockage: Boat Lift
      Lot
      • Size: 0.31 Acres
      • Features: 1/4 - 1/2 Acre
      Details
      • Additional parcels included: 00001900000000
      • Parcel number: 00002160000000
      • Zoning: SF
      • Zoning description: Single Family

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • CBS, Combo Construction, Frame, Concrete
      • Roof: Metal
      Condition
      • Updated/Remodeled
      • New construction: No
      • Year built: 1967

      Utilities & green energy

      • Sewer: Municipal Sewer, Public Sewer
      • Utilities for property: FKAA

      Community & HOA

      Community
      • Features: Fire Hydrant
      • Subdivision: Hilton Haven Sec 2 A (2.0)
      HOA
      • Has HOA: No
      • Services included: None
      Location
      • Region: Key West

      Financial & listing details

      • Price per square foot: $1,444/sqft
      • Annual tax amount: $11,964
      • Date on market: 10/16/2025
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        Estimated market value

        $4,686,500

        $4.45M - $4.92M

        Not available

        Price history

        Price history
        DateEventPrice
        2/2/2026Price change$5,195,000-1.9%$1,444/sqft
        Source: FLKMLS #616896 Report a problem
        1/19/2026Price change$5,295,000-1.9%$1,472/sqft
        Source: FLKMLS #616896 Report a problem
        10/16/2025Listed for sale$5,395,000-6.2%$1,500/sqft
        Source: Key West AOR #616896 Report a problem
        6/19/2025Listing removed$5,750,000$1,599/sqft
        Source: FLKMLS #611908 Report a problem
        10/21/2024Listed for sale$5,750,000$1,599/sqft
        Source: FLKMLS #611908 Report a problem
        5/18/2024Listing removed--
        Source: FLKMLS #608513 Report a problem
        2/2/2024Listed for sale$5,750,000$1,599/sqft
        Source: Key West AOR #608513 Report a problem

        Public tax history

        Public tax history
        Tax history is unavailable.

        BuyAbility℠ payment

        Est. payment
        $30,128/mo
        Principal & interest
        $26578
        Property taxes
        $3550
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          Climate risks

          Neighborhood: New Town

          Getting around

          52 / 100
          Somewhat Walkable
          24 / 100
          Minimal Transit
          86 / 100
          Very Bikeable

          Nearby schools

          GreatSchools rating

          Local experts in 33040

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