$4,998,000
OPEN SUN 1PM - 3PM $597K PRICE DROP

Estimated payment $30,745/month

Total Views 12,485
4 Beds
5 Baths
3,336 Sq Ft
$1,498 Price per Sq Ft

About This Home

MOTIVATED SELLERS! Exceptional Old Town estate with pool, gardens, and 2 guest houses in the heart of Key West. This impeccable property blends timeless architecture with modern updates across three beautifully appointed structures. Behind a privacy wall & gate, the estate includes a grand main residence and two guest houses (both with kitchenettes), offering a total of four bedrooms and four-and-a-half baths. The main house welcomes you with an open floor plan, soaring ceilings, and a light-filled living and dining area. A dramatic wall of glass featuring new 40-foot impact-rated Nana doors and skylights opens to reveal lush tropical gardens and a resurfaced PebbleTec pool with a cascading waterfall. The heated, chilled, and saltwater-converted pool includes new tiled coping and a remote-controlled waterproof outdoor TV for movies or game nights under the stars. The gourmet kitchen features top-of-the-line appliances, Italian cabinetry, Silestone countertops, and a new espresso bar with wine cooler and beverage center. Real stone and hardwood floors run throughout, including two spacious bedrooms, each with an en-suite bath. The primary suite offers French doors and a spa-like bathroom with premium fixtures. The front guest house provides flexible living space currently a den or ''man cave'' with a bedroom, pantry kitchen, and a stunning bath clad in rare iridescent Czechoslovakian green glass from the 1950s. The rear guest cottage, tucked at the back of the property, includes its own sitting & dining areas, wet-bar, vaulted ceilings, a unique bath with outdoor shower & a private porch overlooking the pool & garden. Additional upgrades include a whole-house generator, new exterior lighting and irrigation by Blue Island, a state-of-the-art sound system, hurricane and plantation shutters, fresh exterior paint, and lush landscaping. 2 off-street parking spaces complete this remarkable Old Town retreat.

Listing Agent

Terri Spottswood

Truman & Co. (KW) Brokerage Phone: 305-587-3407 License #161619 Listed on: 10/24/2025

Co-Listing Agent

The Spottswood Team

Truman & Co. (KW) Brokerage Phone: 305-587-3407

Open House Schedule

Home Details

Home Type

  • Single Family

Year Built

  • 1938

Interior Spaces

  • Vaulted Ceiling
  • Plantation Shutters

Home Details

Home Type

Single Family

Year Built

1938

Lot Details

9,148 Sq Ft Lot

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • First Right of Refusal: No
  • Mandatory HOA: No
  • Fee Includes: None
  • Financial Status Bank Owned: No
  • Key Island: Key West
  • K W Neighborhood: Old Town-N of Truman
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 1.00
  • Min Rental Days: 28.00
  • M L S Identifier: 20060123165453488875000000
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Side: Median
  • State Province: FL
  • Taxes: 24447.08
  • Vehicle Storage: Off Street Parking
  • Vehicle Storage Cars: 2
  • Year Built: 1938
  • Alternate Key Number: 1007731
  • Cooling Heating: Central Air, Ceiling Fans(s)
  • Lot Sq Ft: 9180.00
  • Pool Info: In Ground, Concrete, Salt Water
  • Pool Info Heated: Yes
  • Porch Balcony: Deck, Patio
  • Shutters: Bahama
  • Tax Exemptions: None
  • Building Style Above Flood: Unknown
  • Building Style Stories: 1 Story
  • Estimated Living Sq Ft: 3336.00
  • Pool Info Other: Chilled
  • Pre Wired: Surround Sound
  • Specialty Rooms Guest Servant Qtrs: Legal
  • Property Condition: Updated/Remodeled
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Attribution Contact: 305-587-3407
  • Special Features: OpenHouse
  • Property Sub Type: Detached

Interior Features

  • Interior Amenities: Drapes/Blinds Incl, Window Treatments, Built-in Cabinets, Whirlpool Bath Tub, Entrance Foyer, Cathedral Ceilings, Wet Bar
  • Total Bathrooms: 5.00
  • Full Bathrooms: 4
  • Appliances: Washer, Wine Cooler, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Floor: Tile, Wood
  • Half Bathrooms: 1
  • Windows/Doors: Glass Doors, Impact Rstnce Doors, Other Windows/Doors
  • Total Bedrooms: 4
  • Sq Ft Remarks: Buyer to verify square footage

Exterior Features

  • Dockage: None
  • Waterfront: None
  • Waterfront: No
  • Construction: Frame
  • Exterior Features: Fencing, Water Display, Outdoor Shower, Lanai, Lighting, Detached Guest Qtrs
  • Roof: Metal Roof
  • Waterview: No Waterview
  • Pool: Yes

Utilities

  • Utilities: FKAA, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Heating: Central

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: AE
  • Parcel Number: 00007460-000000
  • Land Size: Less Than 1/4 Acre
  • Acres: 0.21

Rental Info

  • Rentals Allowed: With Restrictions

Tax Info

  • Tax Year: 2024

Map

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
01/30/2026 01/30/26 Price Changed $4,998,000 -6.5% $1,498 / Sq Ft
01/28/2026 01/28/26 Price Changed $5,345,000 -0.9% $1,602 / Sq Ft
12/30/2025 12/30/25 Price Changed $5,395,000 -1.8% $1,617 / Sq Ft
12/01/2025 12/01/25 Price Changed $5,495,000 -1.8% $1,647 / Sq Ft
10/24/2025 10/24/25 For Sale $5,595,000 +11.9% $1,677 / Sq Ft
02/23/2024 02/23/24 Sold $5,000,000 -13.8% $1,513 / Sq Ft View Prior Sale
02/15/2024 02/15/24 Pending -- -- --
12/27/2023 12/27/23 For Sale $5,800,000 +87.1% $1,755 / Sq Ft
02/28/2018 02/28/18 Sold $3,100,000 -13.8% $911 / Sq Ft View Prior Sale
01/17/2018 01/17/18 Pending -- -- --
10/19/2017 10/19/17 For Sale $3,595,000 +30.7% $1,056 / Sq Ft
02/13/2015 02/13/15 Sold $2,750,000 -7.6% $808 / Sq Ft View Prior Sale
01/05/2015 01/05/15 Pending -- -- --
01/06/2014 01/06/14 For Sale $2,975,000 -- $874 / Sq Ft
Source: Key West Association of REALTORS®

Source: Key West Association of REALTORS®

MLS Number: 617020

Key West Association of REALTORS®
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