A Key West original. 1014 Flagler Avenue is a storied Casa Marina residence shaped by legendary Key West developer David Wolkowsky and set behind privacy walls on an exceptional 11,730-square-foot corner double lot. Some homes are built. Others are authored. At its center: 40 feet of pool, surrounded by mature tropical landscaping and hardscape by Craig Reynolds Landscape Architecture, creating the feel of a private compound hidden in plain sight. Inside, the scale shifts again with 22-foot ceilings, walls of glass, 10-foot doors and sliders, custom teak, and a dramatic floor-to-ceiling library. The main residence offers two bedrooms and two-and-a-half baths, anchored by a chef's kitchen and expansive indoor-outdoor living. Extensive updates include new systems and impact-rated windows and doors. A completely separate one-bedroom guest house adds its own kitchen, laundry and private garden. 3 bedrooms. 3.5 baths. 3,104 square feet. 11,730 square feet of land. 40 feet of pool. In a market full of beautiful houses, 1014 Flagler offers something harder to replicate: a point of view.
For sale
$4,700,000
1014 Flagler Ave, Key West, FL 33040
3beds
3,104sqft
Single Family Residence
Built in 1998
0.27 Acres Lot
$4,425,000 Zestimate®
$1,514/sqft
$-- HOA
What's special
Custom teakExpansive indoor-outdoor livingDramatic floor-to-ceiling libraryWalls of glassPrivacy wallsImpact-rated windows and doorsPrivate garden
- 42 days
- 1,039
- 74
Zillow last checked:
Listing updated:
Listed by:
Team Kaufelt 305-393-1267,
Truman & Co. (KW)
Source: FLKMLS,MLS#: 618577
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Cooling
- Central Air, Wall/Window Unit(s), Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Gas Appliances, Wine Cooler, Stainless Steel Appliance(s)
- Laundry: Laundry Room
Features
- Split Bedroom, Built-in Features, Walk-in Closet(s), Tray Ceiling(s)
- Windows: Skylight(s)
Interior area
- Total structure area: 3,104
- Total interior livable area: 3,104 sqft
Video & virtual tour
Property
Accessibility
- Accessibility features: Accessible Approach with Ramp
Features
- Patio & porch: Open Porch/Balcony, Patio
- Exterior features: Rain Gutters, Lighting, Water Display
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Privacy
Lot
- Size: 0.27 Acres
Details
- Additional structures: Guest House
- Parcel number: 00058260000000
- Zoning: SF - Single Family
- Other equipment: Irrigation Equipment
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Other
- Property subtype: Single Family Residence
Materials
- CBS
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1998
Utilities & green energy
- Utilities for property: Elect Separate Meter, Cable Available, See Remarks
Community & HOA
Community
- Features: Fire Hydrant, Beach, Bike Paths
- Security: Other
- Subdivision: Martello Towers (1.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Key West
Financial & listing details
- Price per square foot: $1,514/sqft
- Tax assessed value: $3,507,521
- Annual tax amount: $28,771
- Date on market: 10/1/2026
- Listing terms: Cash,Conventional
Estimated market value
$4,425,000
$4.20M - $4.65M
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 10/1/2026 | Listed for sale | $4,700,000-5.9%$1,514/sqft |
Source:  FLKMLS #618577 Report a problem | ||
| 7/7/2026 | Listing removed | $4,995,000$1,609/sqft |
Source:  Key West AOR #618577 Report a problem | ||
| 5/14/2026 | Price change | $4,995,000-2%$1,609/sqft |
Source: Key West AOR #618577 Report a problem | ||
| 5/1/2026 | Price change | $5,095,000-2.6%$1,641/sqft |
Source: Key West AOR #618577 Report a problem | ||
| 4/21/2026 | Price change | $5,230,000-12.8%$1,685/sqft |
Source: Key West AOR #618577 Report a problem | ||
| 3/25/2026 | Price change | $5,995,000-7.7%$1,931/sqft |
Source: Key West AOR #618577 Report a problem | ||
| 2/10/2026 | Listed for sale | $6,495,000+149.8%$2,092/sqft |
Source: Key West AOR #618577 Report a problem | ||
| 2/7/2020 | Sold | $2,600,000-5.5%$838/sqft |
Source: Public Record Report a problem | ||
| 11/13/2019 | Listed for sale | $2,750,000-6.8%$886/sqft |
Source: Truman & Co. (KW) #588525 Report a problem | ||
| 3/5/2019 | Price change | $2,950,000-7.8%$950/sqft |
Source: Truman & Co. (KW) #588525 Report a problem | ||
| 2/12/2019 | Price change | $3,200,000-7.2%$1,031/sqft |
Source: Truman & Co. (KW) #588525 Report a problem | ||
| 11/28/2018 | Listed for sale | $3,450,000$1,111/sqft |
Source: Truman & Co. (KW) #588525 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $28,772 +8% | $3,278,915 +10% |
| 2024 | $26,636 +6.5% | $2,980,832 +10% |
| 2023 | $25,003 +13.9% | $2,709,847 +10% |
| 2022 | $21,951 +9.5% | $2,463,497 +10% |
| 2021 | $20,039 +14.2% | $2,239,543 +23.8% |
| 2020 | $17,546 | $1,809,522 +3.4% |
| 2019 | $17,546 +14.9% | $1,749,771 +6.1% |
| 2018 | $15,269 +6% | $1,649,698 +21.3% |
| 2017 | $14,403 +11.8% | $1,359,523 -8.3% |
| 2016 | $12,881 -13% | $1,481,929 -6.4% |
| 2015 | $14,807 | $1,582,710 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: Casa Marina
Similar homes
- $4,650,0004 bd5 ba3.5k sqft1028 Flagler Ave, Key West, FL 33040For Sale
MLS ID #621710, Team Kaufelt, Truman & Co. (KW). FLKMLS - $4,995,0004 bd3 ba2k sqft1100 Johnson St, Key West, FL 33040For Sale
MLS ID #621521, The Spottswood Team, Truman & Co. (KW). FLKMLS - $5,650,0004 bd4 ba2.6k sqft1119 Johnson St, Key West, FL 33040New Construction
MLS ID #621891, Corinne Held, PA, Preferred Properties (KW). FLKMLS - $4,950,0004 bd4 ba2.4k sqft720D Simonton St, Key West, FL 33040For Sale
MLS ID #621632, The Spottswood Team, Truman & Co. (KW). FLKMLS
