536 Fleming St #2, Key West, FL 33040
Property image
Property image
OFF MARKET

536 Fleming St #2
Key West, FL 33040

Old Town
  • 3 Beds
  • 2 Baths
  • 1,800 sqft
3 Beds
2 Baths
1,800 sqft

Local Information

  • Map ViewExplore the area around 536 Fleming St #2.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Apartment
Living Area
1,800 sqft

About this House

Woven throughout this 2,000+ square foot luxury penthouse is a story that can only be revealed by experience.

The Maloney encompasses the entire second story of the historic red brick building on the corner of Fleming and Simonton. Originally built in 1908 as the first pharmacy in Key West, the building now houses two penthouse units and a first-floor clothing and arts boutique.

Idyllic Key West mornings are sure to take place at the Maloney, where the soft light of sunrise meanders through the 19th century brick framed windows, offering the perfect pairing for a velvety cup of cafe con leche and a slow drip of energy to start your day. Enjoy vibrant Key West evenings where the curated collection of local paintings and carvings compete with the glow of the 100 year-old Dade county pine floors make the perfect setting to host a quiet dinner or serve cocktails to friends.

General Policies: Renters will not receive any refund or reimbursement within 60 days of arrival. Outside of 60 days renters can receive a full refund. Renters must provide a written request.

OTHER INFO:
- House is fully furnished.
- All utilities are included.
- Full payment for the entire term is required in order to rent this property, however, some rental periods may be subject to a payment plan upon request.
- We do not accept checks or cash, payments must be made with a credit card or debit card.
- There are required additional fees.
536 Fleming St #2, Key West, FL 33040 is a 3 bedroom, 2 bathroom, 1,800 sqft apartment in Old Town. More recently, it was listed as a rental in April 2026 with an asking price of $17,500 per month. That rental listing was removed on August 3, 2026. It is currently off market. The Trulia Estimate rent is $5,622/month.

Home Details for 536 Fleming St #2

Interior Features

Heating & Cooling
Heating: CentralAir ConditioningCooling System: Air Conditioner, Central AirHeating Fuel: Central
Appliances & Utilities
DishwasherRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood
Room & Shared Space
Shared space is furnished

Property Information

Property Type / Style
Property Type: Apartment

Rental Terms, Policies & Fees

Lease Term: 1 Month

Price History for 536 Fleming St #2

DatePriceEventSource
08/03/2026$17,000ListingRemovedZillow Rentals
06/08/2026$17,000PriceChange
Zillow Rentals
04/27/2026$17,500Listed For RentZillow Rentals
04/17/2026$17,500ListingRemovedZillow Rentals
03/16/2026$17,500PriceChange
Zillow Rentals
01/29/2026$18,500Listed For RentZillow Rentals
01/13/2026$18,500ListingRemovedZillow Rentals
10/10/2025$18,500PriceChange
Zillow Rentals
07/18/2025$13,500PriceChange
Zillow Rentals
02/19/2025$14,000PriceChange
Zillow Rentals
01/16/2025$18,500PriceChange
Zillow Rentals
01/06/2025$13,500Listed For RentZillow Rentals
12/06/2024$13,500ListingRemovedZillow Rentals
12/03/2024$13,500Listed For RentZillow Rentals

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Comparable Sales for 536 Fleming St #2

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
421 United St, Key West, FL
0.63
Apartment
$200,000
06/29/26
3
3
2,500
1113 Truman Ave, Key West, FL
0.62
Apartment
$1,700,000
10/21/25
2
1
700
1119 Simonton St #A1, Key West, FL
0.53
Apartment
$1,425,000
06/25/26
1
1
600
30 Hilton Haven Dr #2B, Key West, FL
1.36
Apartment
$900,000
08/13/25
2
2
1,045
1616 Bertha St #2, Key West, FL
1.45
Apartment
$1,075,000
12/19/25
2
2
898
1412 Johnson St #2, Key West, FL
1.16
Apartment
$1,247,000
09/03/25
1
1
400
3314 Northside Dr #26, Key West, FL
2.52
Apartment
$614,000
08/13/25
2
3
1,400
3312 Northside Dr #111, Key West, FL
2.52
Apartment
$430,000
04/29/26
2
2
792
3675 S Roosevelt Blvd, Key West, FL
3.16
Apartment
$15,000
04/15/26
2
2
1,066
908 Trinity Dr #5, Key West, FL
2.74
Apartment
$1,000,000
01/15/26
1
250
Home facts updated by county records

Nearby homes

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Assigned Schools

These are the assigned schools for 536 Fleming St #2.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Old Town
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Old Town

At least 1 Trulia users voted on each feature.

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say there are sidewalks

  • 100 % Say streets are well-lit

  • 100 % Say neighbors are friendly

  • 100 % Say it's quiet

  • 100 % Say it's walkable to grocery stores

  • 100 % Say it's walkable to restaurants

  • 100 % Say parking is easy

  • 100 % Say car is needed

  • 67 % Say there's holiday spirit

  • 60 % Say they plan to stay for at least 5 years

  • 50 % Say there are community events

  • 50 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
    Flag
  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
    Flag
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
    Flag
  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
    Flag
  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • Drlynmar
    "Neighborhood newsletter. Proximity to OldTown events, festivals and parades. Walk to everything. Parks, beaches, dog park. Grocery and restaurant delivery. "
    2
    Flag
  • Venomousink1970
    "the neighborhood is great I myself do not like living in Key West anymore and looking to relocate and Asheville North Carolina or the surrounding areas people are very friendly here except for the homeless vagrants that beg for money and yell at you when you don't give them any"
    0
    Flag
  • Lorettamdt
    "Old Town is historic. Our neighbors are friendly. We walk everywhere. No need for a car. Restaurants are within walking distance. Beaches are a bicycle ride away. "
    0
    Flag
  • mangiamangia
    "Lived in this neighborhood for 25 years. Walk and anywhere. Far enough of Duval to escape the noise and drunks."
    0
    Flag
  • Sajsk
    "vacationed in that area -- charming and great location and amenities, yet quiet."
    0
    Flag
  • Rjones
    "This is a great street and great neighborhood. Qiet, yet close enough to Duval and White streets to enjoy all Key West has to offer. "
    0
    Flag

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Off Market Homes Near 536 Fleming St #2

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