720D Simonton St Key West, FL 33040
Old Town NeighborhoodEstimated payment $28,626/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: 01/12/2026
Map
Home Details
Home Type
Single Family
Year Built
2008
Lot Details
0
Listing Details
- Property Type: Residential
- Style: Single Family
- Additional Assessor Parcel Number 1: 00015880-000000
- First Right of Refusal: No
- Mandatory HOA: No
- Fee Includes: None
- Financial Status Bank Owned: No
- Financial Status Potential Short Sale: 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: 1.00
- M L S Identifier: 20060123165453488875000000
- Pets: Pets Allowed
- Property Group I D: 19990816212109142258000000
- Side: Median
- State Province: FL
- Taxes: 31381.00
- Vehicle Storage: Off Street Parking
- Vehicle Storage Cars: 2
- Year Built: 2008
- Alternate Key Number: 1016268
- Cooling Heating: Central Air, Ceiling Fans(s)
- Lot Sq Ft: 5220.00
- Pool Info: In Ground, Concrete
- Pool Info Heated: Yes
- Porch Balcony: Open Porch/Balcony, Patio
- License Info Number Of City License: 2
- Tax Exemptions: None
- Building Style Above Flood: Unknown
- Building Style Stories: 2 Stories
- License Info Transient Rntl Licns: Yes
- Estimated Living Sq Ft: 2441.00
- 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: None
- Property Sub Type: Detached
- Stories: 2
Interior Features
- Interior Amenities: Drapes/Blinds Incl, Window Treatments, Walk-in Closet(s), Storage, Built-in Cabinets, Pantry
- Total Bathrooms: 4.00
- Full Bathrooms: 4
- Appliances: Washer, Wine Cooler, Freezer, Microwave, Range, Refrigerator, Dishwasher, Dryer
- Floor: Tile, Wood
- Windows/Doors: Glass Doors, Aluminum Windows, Sliding Glass Doors
- Total Bedrooms: 4
- Sq Ft Remarks: Buyer to verify square footage
Exterior Features
- Dockage: None
- Waterfront: None
- Waterfront: No
- Construction: CBS, Combo Construction, Concrete
- Exterior Features: Detached Guest Qtrs, Water Display, Storage, Privacy Wall/Fence, Outdoor Shower, Lighting
- Roof: Metal Roof
- Waterview: No Waterview
- Pool: Yes
Utilities
- Security: Electric Gate
- Utilities: FKAA, Buyer to Verify, Municipal Sewer
Lot Info
- Deed Restrictions: Unknown
- Flood Zone: X FLOOD ZONE
- Land Size: Less Than 1/4 Acre
Rental Info
- Rentals Allowed: Yes
Tax Info
- Tax Year: 2025
Multi Family
- Total Units: 2.00
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 |
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $4,700,000 | Spottswood Spottswood Spottswo | |
| Warranty Deed | $1,450,000 | -- | |
| Quit Claim Deed | $884,500 | -- | |
| Warranty Deed | $1,175,000 | -- | |
| Warranty Deed | $330,000 | -- | |
| Deed | $110,000 | -- |
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Open | $2,350,000 | New Conventional | |
| Previous Owner | $1,160,000 | Fannie Mae Freddie Mac |
Source: Key West Association of REALTORS®
MLS Number: 618363
APN: 00015880-000000
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