916 Fleming St, Key West, FL 33040
Property image
Property image
OFF MARKET

916 Fleming St
Key West, FL 33040

Old Town
  • 4 Beds
  • 6 Baths
  • 2,670 sqft

$3,260,100

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $18,668/mo*
Refinance Your Home

$3,260,100

Trulia Estimate
as of Jul 10, 2026
Est. Refi. Payment $18,668/mo*
Refinance Your Home
4 Beds
6 Baths
2,670 sqft

Local Information

  • Map ViewExplore the area around 916 Fleming St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

Beautiful old town home with a guest cottage. Marble counter tops throughout, dark wood floors throughout with marble flooring in the bathrooms. Built in cabinets and walk in closets. All bedrooms have full bathrooms, .5 bath inside one in guest cottage. Sliding pocket doors to outside deck area with auto screens to come down on two sides. Guest cottage has built in cabinets, loft and a half bath that also opens out onto the pool area. Pool is heated has attached spa and waterfall. A must see. Just appraised, appraisal avaliable.
916 Fleming St, Key West, FL 33040 is a 4 bedroom, 6 bathroom, 2,670 sqft single-family home in Old Town, built in 1938. It last sold for $1,475,000 on Aug 26, 2013. It is currently off market. The Trulia Estimate is $3,260,100, with a rent estimate of $8,180/month.

Home Highlights

Parking
Garage
Outdoor
Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 916 Fleming St

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
AtticWet Bar
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: OtherDeckExterior: WoodFoundation Type: ConcreteLawnSprinkler System
Pool
Pool
Parking & Garage
GarageParking: Off Street, Garage

Property Information

Year Built
Year Built: 1938Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 3876 sqft

Price History for 916 Fleming St

DatePriceEventSource
08/26/2013$1,475,000Sold
FLKMLS #117761
07/21/2013$1,600,000PendingAgent Provided
06/27/2013$1,600,000PriceChange
Agent Provided
05/07/2013$1,650,000PriceChange
Agent Provided
04/24/2013$1,675,000PriceChange
Agent Provided
04/03/2013$1,729,000PriceChange
Agent Provided
03/08/2013$1,750,000PriceChange
Agent Provided
03/02/2013$1,500,000Listed For SaleAgent Provided
09/24/2010$1,300,000Sold
FLKMLS #112664
06/26/2010$1,500,000Listed For SaleAgent Provided
03/22/2010$800,000Sold
N/A
07/11/2009$2,500,000PriceChange
Agent Provided
01/27/2009$2,790,000PriceChange
Agent Provided
01/13/2009$1,995,000PriceChange
Agent Provided
07/19/2008$3,400,000Listed For SaleAgent Provided
05/01/2006$1,500,000Sold
N/A
12/14/2004$1,300,000Sold
N/A

Market trends in Key West

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.2M
$61.67KMoM
Sale-to-List Price
94.9%
0.4%MoM
Price per sq ft
$940
$14MoM
Available listings
304
28MoM
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Property Tax and Assessment

Year2025
Tax$14,550
Assessment$2,723,219
Home facts updated by county records

Comparable Sales for 916 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
510 Margaret St, Key West, FL
0.06
Single-Family Home
$2,850,000
04/17/26
4
4
1,968
1015 Eaton St, Key West, FL
0.13
Single-Family Home
$1,900,000
03/30/26
4
3
1,738
1020 Southard St, Key West, FL
0.14
Single-Family Home
$3,350,000
12/03/25
3
3.5
2,438
531 Frances St, Key West, FL
0.15
Single-Family Home
$1,825,000
02/20/26
3
2.5
1,681
1006 & 1008 Fleming St, Key West, FL
0.06
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
906 Southard St, Key West, FL
0.10
Single-Family Home
$3,250,000
05/27/26
3
3
2,188
517 Elizabeth St, Key West, FL
0.21
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
831 Georgia St, Key West, FL
0.41
Single-Family Home
$2,290,000
08/25/25
4
4
2,028
312 Margaret St, Key West, FL
0.16
Single-Family Home
$2,295,000
04/15/26
3
3
1,916
1217 Petronia St, Key West, FL
0.34
Single-Family Home
$1,500,000
02/03/26
3
2.5
1,667

Nearby homes

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Assigned Schools

These are the assigned schools for 916 Fleming St.
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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Apartments for Rent

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Explore by feature - Pet Friendly

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Homes for sale near 916 Fleming St

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Off Market Homes Near 916 Fleming St

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