529 Caroline St, Key West, FL 33040
OFF MARKET

529 Caroline St
Key West, FL 33040

Historic Seaport
  • 8 Beds
  • 3 Baths
  • 3,600 sqft (on 0.34 acres)

$3,377,100

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $19,176/mo*
Refinance Your Home

$3,377,100

Trulia Estimate
as of Jul 5, 2026
Est. Refi. Payment $19,176/mo*
Refinance Your Home
8 Beds
3 Baths
3,600 sqft
(on 0.34 acres)

Local Information

  • Map ViewExplore the area around 529 Caroline St.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Description

This single-family home is located at 529 Caroline St, Key West, FL. 529 Caroline St is in the Historic Seaport neighborhood in Key West, FL and in ZIP code 33040. This property has 8 bedrooms, 3 bathrooms and approximately 3,600 sqft of floor space. This property has a lot size of 0.34 acres and was built in 1899.
529 Caroline St, Key West, FL 33040 is a 8 bedroom, 3 bathroom, 3,600 sqft single-family home in Historic Seaport, built in 1899. It last sold for $2,290,000 on Mar 18, 2019. It is currently off market. The Trulia Estimate is $3,377,100, with a rent estimate of $6,279/month.

Home Highlights

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

Home Details for 529 Caroline St

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Softwood, Concrete, Hardwood
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: MetalExterior: Wood, BrickFoundation Type: Slab

Property Information

Year Built
Year Built: 1899Year Updated: 1979
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 9

Lot Information

Lot Area: 0.34 acres

Price History for 529 Caroline St

DatePriceEventSource
03/18/2019$2,290,000Sold
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
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$21,929
Assessment$2,681,225
Home facts updated by county records

Comparable Sales for 529 Caroline St

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
101 Admirals Ln, Key West, FL
0.29
Single-Family Home
$6,300,000
10/10/25
5
4
3,173
326 Caroline St, Key West, FL
0.23
Single-Family Home
$6,350,000
01/15/26
5
5.5
4,279
215 Whitehead St, Key West, FL
0.15
Single-Family Home
$2,300,000
02/25/26
3
3
1,514
400 Aronovitz Ln, Key West, FL
0.37
Single-Family Home
$3,300,000
05/21/26
5
6
3,667
407-415 Olivia St, Key West, FL
0.52
Single-Family Home
$3,500,000
08/08/25
6
5
3,171
728 Love Ln, Key West, FL
0.27
Single-Family Home
$3,150,000
09/19/25
3
3
2,100
517 Elizabeth St, Key West, FL
0.26
Single-Family Home
$3,750,000
10/20/25
4
3
2,173
312 Margaret St, Key West, FL
0.27
Single-Family Home
$2,295,000
04/15/26
3
3
1,916
1006 & 1008 Fleming St, Key West, FL
0.44
Single-Family Home
$4,425,000
05/26/26
4
4.5
3,336
316 Southard St, Key West, FL
0.36
Single-Family Home
$3,500,000
10/20/25
3
3.5
2,532

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 529 Caroline 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

Historic Seaport
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Historic Seaport

At least 38 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 90 % Say people would walk alone at night

  • 88 % Say it's walkable to restaurants

  • 84 % Say it's walkable to grocery stores

  • 83 % Say there are sidewalks

  • 79 % Say streets are well-lit

  • 67 % Say yards are well-kept

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there's holiday spirit

  • 60 % Say there's wildlife

  • 59 % Say there are community events

  • 57 % Say it's quiet

  • 43 % Say parking is easy

  • 42 % Say neighbors are friendly

  • 35 % Say kids play outside

  • 30 % Say car is needed

Sourced by Trulia users. Learn more about our methodology.
  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Sue S.
    "We vacationed here for the month of February 2014. We did not rent a car but had bikes for a week. We are walkers and walked an average of 1-2 miles for dinner and many miles during the day touring, hiking, etc. This area is accessible to most anything."
    1
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

20 pet-friendly rentals in Key West, FL

Explore by feature - Garage

7 rentals with a garage in Key West, FL

Explore by feature - Air Conditioning

113 rentals with air conditioning in Key West, FL

Explore by feature - Pool

84 rentals with a pool in Key West, FL

Explore by feature - Washer/dryer

97 rentals with a washer/dryer in Key West, FL

Explore by feature - Outdoor Space

15 rentals with an outdoor space in Key West, FL

Homes for sale near 529 Caroline St

Skip to last item
Skip to first item

Off Market Homes Near 529 Caroline St

Skip to last item
Skip to first item