808 Fleming St, Key West, FL 33040
OFF MARKET

808 Fleming St
Key West, FL 33040

Old Town
  • 4 Beds
  • 3 Baths
  • 2,003 sqft

$1,755,000

Trulia Estimate
as of Jun 20, 2026
Est. Refi. Payment $9,928/mo*
Refinance Your Home

$1,755,000

Trulia Estimate
as of Jun 20, 2026
Est. Refi. Payment $9,928/mo*
Refinance Your Home
4 Beds
3 Baths
2,003 sqft

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

This charming three-unit property at 808 Fleming Street represents an exceptional investment in one of Key West's most desirable neighborhoods. Located in the historic Old Town district, this versatile building offers multiple revenue streams and tremendous potential for savvy investors.This property is ideal for investors or multi-family living. With separate electric and water meters for each unit, management is effortless and efficient.Property Features:Downstairs Unit: A spacious 984 sq. ft. living area, perfect for an owner's residence or premium rental unit. Its open layout offers flexibility and comfort.Upstairs Units: Two additional units occupy 1,019 sq. ft. of living space, providing privacy, comfort, and excellent rental potential.Outdoor Living:Island living comes alive with this property's inviting front porch and expansive front balcony, perfect for enjoying the tropical breezes. The private backyard includes a 22' x 18' wooden deck and an additional 22' x 23'-yard area, offering endless possibilities for entertaining, relaxation, or further enhancements. An unused 11' x 6' cistern adds a touch of Key West history and utility to this unique property.Prime Location:Centrally located, this property provides easy access to Key West's vibrant dining, shopping, and world-famous nightlife. Tenants and residents will enjoy the best of island life, with the perfect balance of convenience and tranquility in a sought-after neighborhood.Endless Potential:This multi-unit property offers endless possibilities--generate strong rental income, create a multi-generational living arrangement, or craft your dream Key West retreat. With its combination of private utilities, multiple spaces, and outdoor amenities, this property is ready to fulfill your vision.Call today
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from February 14, 2025

Home Highlights

Parking
No Info
Outdoor
Porch, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 808 Fleming St

Interior Features

Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2003 Square Feet
Appliances & Utilities
Utilities: FKAAAppliances: Refrigerator, RangeRefrigerator
Heating & Cooling
Has CoolingAir Conditioning: Wall/Window Unit(s),Ceiling Fans(s)
Gas & Electric
Electric: Elect Separate Meter
Windows, Doors, Floors & Walls
Window: Jalousie Windows, Other Windows/Doors, Wood FramesFlooring: Tile, Combination, Wood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoAccessibility: NoFloors: Tile, Combination, Wood
Security
Security: No Security

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Open Porch/Balcony, DeckFencing: FencedVegetation: Fruit Tree(s)Exterior: Rain GuttersNo Private Pool
Frontage
Waterfront: None, Dockage: NoneNot on Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Property Information

Year Built
Year Built: 1928
Property Type / Style
Property Type: ResidentialProperty Subtype: Multi FamilyArchitecture: Conch
Building
Construction Materials: Frame
Property Information
Parcel Number: 00008330000000

Price & Status

Price
List Price: $1,850,000

Active Status

MLS Status: Closed

Location

Direction & Address
City: Key WestCommunity: Old Town - Unlisted (1.0)

HOA

HOA Fee Includes: NoneAssociation for this Listing: Key West AssociationNo HOA

Lot Information

Lot Area: 2613.6 sqft

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 612348Water View: None
Last check for updates: about 8 hours ago
Listed by Barbara B Crespo, (305) 797-0803
Keller Williams Key West Compass Realty
Bought with: Robin G Nilsson, (239) 221-4230, Keller Williams Key West Compass Realty
Co-Buyer's Agent: Gregg Powers, (206) 264-0600, Keller Williams Key West Compass Realty
Originating MLS: Key West Association
Source: FLKMLS, MLS#612348

Price History for 808 Fleming St

DatePriceEventSource
02/14/2025$1,800,000Sold
FLKMLS #612348
11/27/2024$1,850,000ContingentFLKMLS #612348
11/21/2024$1,850,000Listed For SaleFLKMLS #612348

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$10,538
Assessment$1,164,073
Home facts updated by county records

Homeowner tools

Estimated monthly rent$5,727/mo
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Homes for rent near 808 Fleming St

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Comparable Sales for 808 Fleming St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1030 James St, Key West, FL
0.26
Multi-Family Home
$1,800,000
05/26/26
3
3
1,700
830 Fleming St, Key West, FL
0.04
Multi-Family Home
$1,350,000
10/20/25
3
4
1,989
514 Margaret St, Key West, FL
0.05
Multi-Family Home
$1,400,000
01/14/26
5
3.5
2,068
621 Elizabeth St, Key West, FL
0.17
Multi-Family Home
$1,625,000
04/20/26
3
2
1,594
704 Caroline St, Key West, FL
0.20
Multi-Family Home
$1,750,000
08/05/25
4
5
2,080
708 William St, Key West, FL
0.24
Multi-Family Home
$1,752,000
11/17/25
4
3.5
1,967
737 Olivia St, Key West, FL
0.31
Multi-Family Home
$1,525,000
07/08/25
3
3
1,860
602 Southard St, Key West, FL
0.21
Multi-Family Home
$1,425,000
07/10/25
3
3
2,671
308 Peacon Ln, Key West, FL
0.18
Multi-Family Home
$850,000
10/31/25
3
2.5
1,296
1113 Watson St, Key West, FL
0.55
Multi-Family Home
$1,300,000
03/20/26
5
3
1,819

Nearby homes

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Assigned Schools

These are the assigned schools for 808 Fleming St.
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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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Homes for sale near 808 Fleming St

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Off Market Homes Near 808 Fleming St

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MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.
808 Fleming St, Key West, FL 33040 is a 4 bedroom, 3 bathroom, 2,003 sqft multi-family built in 1928. 808 Fleming St is located in Old Town, Key West. This property is not currently available for sale. 808 Fleming St was last sold on Feb 14, 2025 for $1,800,000 (3% lower than the asking price of $1,850,000). The current Trulia Estimate for 808 Fleming St is $1,755,000.