# 1014 Flagler Avenue, Key West, FL 33040

> **TL;DR:** 3bd/4ba single family, $4,700,000 ($1514/sqft), built 1998, 3,104 sqft.
> Pool, View, A/C. Est. $25,137/mo. Listed 266 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $4,700,000 |
| Price/sqft | $1514 |
| Bedrooms | 3 |
| Bathrooms | 3 full, 1 half |
| Square Feet | 3,104 |
| Year Built | 1998 |
| Lot Size | 11,731 sqft (0.27 acres) |
| Property Type | Single Family (Single Family Residence) |
| Status | Active |
| Days on Market | 266 |

## Why This Home Stands Out

- **Pool** - Porch, Patio
- **Views** - Water

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $23,766 |
| Estimated Insurance | $1,371 |
| **Total** | **$25,137** |

## Key Amenities

- Pool
- View
- A/C

## Property Highlights

- Built in 1998
- 0.27 acre lot
- Private pool

## Description

### Agent Description
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.

## Location

- **Address:** 1014 Flagler Avenue, Key West, FL 33040
- **County:** Monroe
- **Neighborhood:** Martello Towers (1.0)
- **Coordinates:** 24.549132, -81.788857
- **Google Maps:** https://www.google.com/maps?q=24.549132,-81.788857

## Virtual Tour & Media

- **Video Tour:** https://mls.ricoh360.com/79b63685-5668-4dff-911f-97f9f9fc7f40

## Listing Agent

- **Name:** Team Kaufelt
- **Brokerage:** Truman & Co. Real Estate Services
- **Broker Phone:** (305) 292-2244
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/1014-Flagler-Ave_Key-West_FL_33040_M93681-64671?f=listhub&s=KWARFL&m=618577&c=propsimple)

## Photos

![1014 Flagler Avenue - Photo 1](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1922837958r.jpg)

![1014 Flagler Avenue - Photo 2](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1960378366r.jpg)

![1014 Flagler Avenue - Photo 3](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1528443064r.jpg)

![1014 Flagler Avenue - Photo 4](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f266426435r.jpg)

![1014 Flagler Avenue - Photo 5](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1089659214r.jpg)

![1014 Flagler Avenue - Photo 6](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3030888615r.jpg)

![1014 Flagler Avenue - Photo 7](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3916498127r.jpg)

![1014 Flagler Avenue - Photo 8](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1597577463r.jpg)

![1014 Flagler Avenue - Photo 9](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1839143746r.jpg)

![1014 Flagler Avenue - Photo 10](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3391907718r.jpg)

![1014 Flagler Avenue - Photo 11](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2415220268r.jpg)

![1014 Flagler Avenue - Photo 12](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2446367267r.jpg)

![1014 Flagler Avenue - Photo 13](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3411316019r.jpg)

![1014 Flagler Avenue - Photo 14](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2617633392r.jpg)

![1014 Flagler Avenue - Photo 15](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1822317106r.jpg)

![1014 Flagler Avenue - Photo 16](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f973872046r.jpg)

![1014 Flagler Avenue - Photo 17](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f90427194r.jpg)

![1014 Flagler Avenue - Photo 18](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2635472536r.jpg)

![1014 Flagler Avenue - Photo 19](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3956426398r.jpg)

![1014 Flagler Avenue - Photo 20](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1131641193r.jpg)

![1014 Flagler Avenue - Photo 21](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3656575150r.jpg)

![1014 Flagler Avenue - Photo 22](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f4065354883r.jpg)

![1014 Flagler Avenue - Photo 23](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f107275691r.jpg)

![1014 Flagler Avenue - Photo 24](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1141692916r.jpg)

![1014 Flagler Avenue - Photo 25](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1079698041r.jpg)

![1014 Flagler Avenue - Photo 26](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3561696141r.jpg)

![1014 Flagler Avenue - Photo 27](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3076512655r.jpg)

![1014 Flagler Avenue - Photo 28](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3670690124r.jpg)

![1014 Flagler Avenue - Photo 29](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3243054571r.jpg)

![1014 Flagler Avenue - Photo 30](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3276380061r.jpg)

![1014 Flagler Avenue - Photo 31](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f1024863720r.jpg)

![1014 Flagler Avenue - Photo 32](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2376024813r.jpg)

![1014 Flagler Avenue - Photo 33](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3328081732r.jpg)

![1014 Flagler Avenue - Photo 34](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f503356175r.jpg)

![1014 Flagler Avenue - Photo 35](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f3103629301r.jpg)

![1014 Flagler Avenue - Photo 36](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f979568570r.jpg)

![1014 Flagler Avenue - Photo 37](http://lh.rdcpix.com/b0ebe760c22f3a39d5933c3ac269854el-f2045897201r.jpg)

---

**MLS#:** 618577 | **Updated:** 2026-10-25
**Source:** listhub

*Copyright © 2026 Key West Association of Realtors. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.*

[View on PropertySimple](https://www.propertysimple.ai/listing/1014-flagler-avenue-key-west-fl-33040-8c7302def5dc407090de5102e9167f9c)

---

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    "@id": "https://www.propertysimple.ai/listing/1014-flagler-avenue-key-west-fl-33040-8c7302def5dc407090de5102e9167f9c#agent",
    "name": "Team Kaufelt",
    "worksFor": {
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      "@id": "https://www.propertysimple.ai/listing/1014-flagler-avenue-key-west-fl-33040-8c7302def5dc407090de5102e9167f9c#brokerage",
      "name": "Truman & Co. Real Estate Services",
      "telephone": "(305) 292-2244",
      "logo": {
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        "url": "http://lh.rdcpix.com/3cb3c48183e111e19b52123138048d21k-c739538518r.png"
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}
```