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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$5,195,000
18 Hilton Haven Road
Key West, FL 33040
MLS# 621709
5 beds  |  6 baths  |  3597 sqft


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DJI_0945crop Private pool and lounging area Rear Deck facing the Yacht Club and Garrison Bight NDP-6271 Front Entrance Front Porch Grand Staircase View out Front Doors View to Living room Living Room Living Room Living Room Living Room Living Room NDP-6703 NDP-6711 NDP-6718 NDP-6723 Dining Area NDP-6395 First Floor Half Bath Rear Deck facing the Yacht Club and Garrison Bight Rear Deck facing the Yacht Club and Garrison Bight Rear Deck facing the Yacht Club and Garrison Bight 15,000 Pound Boat Lift and Dock NDP-6513 NDP-6527 Stairs to Boat Dock and Lift First Floor Primary Bedroom First Floor Primary Bedroom Primary Bath Primary Closet Primary Shower Full Bath in Hallway First Floor Guest Bedroom First Floor Guest Bedroom Grand Staircase to Second Floor Second Floor Setting Area Guest Bedroom 2 Guest Bedroom 2 Guest Bedroom 3 Guest Bedroom 3 Full Bath Full Bath Full Bath Second Floor Setting Area with access to Deck Second Floor Deck Second Floor Deck Second Floor Deck View from Second Floor Deck Second Floor Deck with Entrance to Study/Bedroom Study/Bedroom with Custom Cabinetry. Study/Bedroom with Custom Cabinetry. View from Window looking North and Water Lot. Study/Bedroom with Custom Cabinetry. Full Bath with Shower Second set of stairs to First Floor Garage NDP-6532 NDP-6529 NDP-6535 NDP-6547 NDP-6548 NDP-6562 NDP-6567 Front Porch NDP-6767 DJI_0958_Arrow DJI_0013 DJI_0945 DJI_0949 DJI_0958 DJI_0952_Arrow DJI_0958_Arrow DJI_0961_Arrow Water Lot

Property 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

Details
Maps
Documents
Contract Information
Current Price: $5,195,000
Listing Date: 2026-10-20
Listing Board: Key West Association
Monthly Rent: $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 Size: 75 X 180
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
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock: Other
Appliances
Other: Electric Cook top
Building Style
Above Flood: Unknown
# Stories: 2 Stories
Pool Info
Heated: Yes
Dimensions: 15 X 20
Status Change Info
Status: Active
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
Listing Documents
View Document 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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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)