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.
