18 Hilton Haven Rd

$5,395,000
Price
5
Beds
3,597 Sq. Ft.
$1,500 / Sq. Ft.
3,597
Sq. Ft.
$1,500
per Sq. Ft.

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....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
  1. Listed by The Behmke Group • Keller Williams Key West Compass Realty
  2. Listed by Stephen M Andres • Keller Williams Key West Compass Realty

Property Details for 18 Hilton Haven Road

Waterfront
Bay Front, Open Water
Waterfront
Yes
Zoning
SF - Single Family
Subdivision
Hilton Haven Sec 2 A (2.0)
Vehicle Storage
Garage, Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 12/23/2025 10:34 AM

Property Details for 18 Hilton Haven Road

StatusActive
MLS #616896
Days on Market70
Taxes$11,965 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1967
Lot Size0.19 AC / 8,410 SF
CountyMonroe County

Location

Listing Courtesy of Keller Williams Key West Compass Realty
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Building Information for 18 Hilton Haven Road

Stories2Year Built1967Building Size-Lot Size0.19 AC / 8,410 SF

Payment Calculator

$27,656 per month

30 year fixed, 6.28% Interest

Principal and Interest

$26,659

Property Taxes

$997

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 18 Hilton Haven Road

Summary
Location and General Information
  • Waterview: Bay/Gulf View, Harbor/Marina View, Open Water View
  • Area: 03 - Key West
  • Absolute Longitude: 81.780926
  • Control Depth: 3
  • Listing Board: Key West Association
  • Side: Bay/Gulf
  • KW Neighborhood: Midtown East
  • Mile Marker: 2.0
  • Marathon Neighborhood: N/A
  • Neighborhood Feature: Fire Hydrant
  • Key/Island: Key West
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2024
  • Tax Exemptions: Homestead
Property
Lot Information
  • Acres: 0.31
  • Parcel #: 00002160-000000
  • Add'l Parcel #1: 00001900-000000
  • Land Size: 1/4 - 1/2 Acre
Property and Assessments
  • 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
  • MLS Approved: Y
  • SqFt Source: Tax Records
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 82
  • Document Count: 1
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: Dimensions: 15 X 20
  • Pool Info: In Ground, Concrete
  • Porch/Balcony: Open Porch/Balcony, Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile, Wood
  • Interior Features: Cathedral Ceilings, Walk-in Closet(s), Storage, Granite Counter Top, Built-in Cabinets
  • Appliances: Other: Electric Cook top
  • Appliances: Washer, Stainless Steel Appliance(s), Microwave, Oven, Refrigerator, Dryer
Exterior Features
  • Roof: Metal Roof
  • Dockage: Dock: Other
  • Construction: CBS, Combo Construction, Frame, Concrete
  • Dockage: Boat Lift

Property History for 18 Hilton Haven Road

DateEvent & SourcePriceAppreciation
Oct 16, 2025

Listed (Active)

FKMLS #616896

$5,395,000
Jun 18, 2025

Expired

FKMLS #611908

Oct 21, 2024

Listed (Active)

FKMLS #611908

$5,750,000
May 18, 2024

Temp Off Market

FKMLS #608513

Feb 2, 2024

Listed (Active)

FKMLS #608513

$5,750,000
Mar 28, 2002

Sold

FKMLS #90317

$1,050,000
Mar 20, 2002

Pending

FKMLS #90317

May 11, 2000

Listed (Active)

FKMLS #90317

$1,199,000
Mar 3, 2000

Sold

FKMLS #415899

$725,000
Mar 3, 2000

Pending

FKMLS #415899

Sep 4, 1999

Listed (Active)

FKMLS #415899

$750,000
DateEvent & SourcePrice
10/16/2025

Listed (Active)

FKMLS #616896

$5,395,000
06/18/2025

Expired

FKMLS #611908

10/21/2024

Listed (Active)

FKMLS #611908

$5,750,000
05/18/2024

Temp Off Market

FKMLS #608513

02/02/2024

Listed (Active)

FKMLS #608513

$5,750,000
03/28/2002

Sold

FKMLS #90317

$1,050,000
03/20/2002

Pending

FKMLS #90317

05/11/2000

Listed (Active)

FKMLS #90317

$1,199,000
03/03/2000

Sold

FKMLS #415899

$725,000
03/03/2000

Pending

FKMLS #415899

09/04/1999

Listed (Active)

FKMLS #415899

$750,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 18 Hilton Haven Road

Taxable ValueLand$52Additions-Total$52
Tax Record2024$0 ($0 / month)
Home Facts
Beds0Lot Size2,265,120 SqFtStyleMiscellaneous Vacant LandCountyMONROEAPN00001900-000000

Schools near 18 Hilton Haven Road

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 8 to 12
Public - 9 to 12
Charter - 9 to 12
Rating
School
Distance
Poinciana Elementary School
PublicPK to 5

Keys Center
Public8 to 12

Key West High School
Public9 to 12

Somerset Island Prep
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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18 Hilton Haven Road is a single family home for sale in Key West, FL 33040. This property was listed for sale on October 16, 2025 by Keller Williams Key West Compass Realty, it's currently listed at $5,395,000. It has been on the market for a total of 70 days and was last sold on March 28, 2002. This listing's school district is Monroe. Nearby schools include Poinciana Elementary School, Keys Center and Key West High School. 18 Hilton Haven Road is a 5-bed, 6-bath, 3,597 sqft single family home built in 1967.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Keller Williams Key West Compass Realty

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.