720D Simonton St Key West, FL 33040
Old Town NeighborhoodEstimated payment $29,144/month
About This Home
KEY WEST'S UNLIKELY SANCTUARY | DUAL TRANSIENT LICENSES While most Old Town properties embrace tropical pastels and wooden shutters, this exceptional compound stands as a bold architectural departure. With its striking modern aesthetic, raw concrete elements, and serene private courtyard, this is where minimalist design meets maximum investment potential, just one block from Duval Street. | THE COMPOUND | Built in 2008 on a generous 5,220sf lot, this 2,441sf property features two distinct units, a front house and back house, connected by a heated pool oasis. Four bedrooms, four full baths, soaring two-story ceilings, and thoughtfully curated interiors showcase warm mid-century touches against clean architectural lines. Wood and tile floors, built-in cabinetry, walk-in closets, and abundant natural light through expansive glass doors create spaces that are both meditative and functional. | THE SANCTUARY | High privacy walls enclose a tranquil pool courtyard with tropical landscaping, outdoor shower, and ample off-street parking. Electric gate entry ensures complete seclusion while downtown's energy pulses just steps away. | THE OPPORTUNITY | Two active transient rental licenses with 1-day minimum stays unlock exceptional income in Key West's most sought-after location. The property's distinctive design aesthetic attracts discerning guests seeking something different, proven by outstanding reviews and strong rental performance. HNC zoning supports flexible commercial use, while X flood zone designation offers insurance advantages. | THE LOCATION | Heart of Old Town, steps from Duval's legendary dining, nightlife, galleries, and waterfront. Close enough to all the action, far enough from the noise. This is investment-grade real estate with soul, where architectural distinction drives premium rates and occupancy.
Listing Agent
The Spottswood Team
Truman & Co. (KW) Brokerage Phone: 305-587-3407 Listed on: 01/28/2026
Map
Home Details
Home Type
Single Family
Year Built
2008
Lot Details
4,792 Sq Ft Lot
Listing Details
- Property Type: Residential
- Vehicle Storage Cars: 2
- Year Built: 2008
- Building Style Above Flood: Unknown
- License Info Transient Rntl Licns: Yes
- Specialty Rooms Guest Servant Qtrs: Legal
- Property Condition: Updated/Remodeled
- Attribution Contact: 305-587-3407
- Special Features: VirtualTour
- Property Sub Type: Detached
Interior Features
- Interior Amenities: Built-in Cabinets, Storage, Walk-in Closet(s)
- Appliances: Washer, Dryer, Dishwasher, Refrigerator, Range, Microwave, Freezer, Wine Cooler
Exterior Features
- Waterfront: No
- Exterior Features: Detached Guest Qtrs, Lighting, Outdoor Shower, Privacy Wall/Fence, Storage, Water Display
Tax Info
- Tax Year: 2025
Home Values in the Area
Average Home Value in this Area
Tax History
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2025 | $32,259 | $3,815,344 | $1,597,320 | $2,218,024 |
| 2024 | $29,900 | $3,801,147 | $1,597,320 | $2,203,827 |
| 2023 | $29,900 | $3,464,110 | $1,369,271 | $2,094,839 |
| 2022 | $17,218 | $2,283,077 | $1,037,475 | $1,245,602 |
| 2021 | $15,898 | $1,842,467 | $767,340 | $1,075,127 |
| 2020 | $14,808 | $1,768,008 | $761,468 | $1,006,540 |
| 2019 | $13,175 | $1,468,228 | $565,718 | $902,510 |
| 2018 | $12,662 | $1,448,557 | $530,483 | $918,074 |
| 2017 | $12,245 | $1,459,067 | $0 | $0 |
| 2016 | $12,556 | $1,544,945 | $0 | $0 |
| 2015 | $10,792 | $1,125,169 | $0 | $0 |
| 2014 | $10,217 | $1,013,313 | $0 | $0 |
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 01/12/2026 01/12/26 | For Sale | $4,990,000 | -- | $2,044 / Sq Ft |
Source: Key West Association of REALTORS®
MLS Number: 618363
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Ask me questions while you tour the home.