209 E Carroll St, Islamorada, FL 33036
Property image
Property image
OFF MARKET

209 E Carroll St
Islamorada, FL 33036

  • 8 Beds
  • 5.5 Baths
  • 4,931 sqft (on 2.14 acres)

$3,769,900

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $21,952/mo*
Refinance Your Home

$3,769,900

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $21,952/mo*
Refinance Your Home
8 Beds
5.5 Baths
4,931 sqft
(on 2.14 acres)

Home Value

Trulia Estimate
$3.77M
Since last month
Increased$59K (+1.6%)
Since last year
Increased$258K (+7.2%)
Since last sale
Increased$824K (+27.5%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +149% in the last 10 years
MonthEstimated value
2026
August 2026$3.82M
July 2026$3.77M
June 2026$3.66M
May 2026$3.58M
April 2026$3.54M
March 2026$3.42M
February 2026$3.47M
January 2026$3.38M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
82238 Overseas Hwy, Islamorada, FL
0.22
Single-Family Home
$8,300,000
10/17/25
6
6
6,866
82779 Old Highway 16 Upper Matecumbe Ky, Islamorada, FL
0.53
Single-Family Home
$3,800,000
07/07/26
4
4.5
2,574
105 Carroll Street Upper Matecumbe Ky #6, Islamorada, FL
0.38
Single-Family Home
$2,900,000
03/05/26
4
4.5
2,576
19 Avacado St, Upper Matecumbe Key, FL
0.64
Single-Family Home
$12,000,000
02/13/26
5
6
5,489
100 List St, Islamorada, FL
0.22
Single-Family Home
$5,400,000
05/08/26
3
2.5
3,019
82762 Overseas Hwy #3, Upper Matecumbe Key, FL
0.40
Single-Family Home
$1,700,000
03/30/26
4
4
2,728
81906 Overseas Highway Upper Matecumbe Ky #3, Islamorada, FL
0.44
Single-Family Home
$2,425,000
08/03/26
3
3.5
1,768
82260 Overseas Hwy, Upper Matecumbe Key, FL
0.30
Single-Family Home
$880,000
04/15/26
3
3
2,314
150 List St, Islamorada, FL
0.20
Single-Family Home
$3,100,000
02/12/26
1
1
946
82207 Old Hwy, Islamorada, FL
0.10
Single-Family Home
$775,000
06/18/26
2
2
1,224

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
191 Carroll St, Islamorada, FL 33036
0.02
$1,250,000
3
3
1,550
For Sale
189 Carroll St, Islamorada, FL 33036
0.03
$1,250,000
3
3
1,525
For Sale
207 & 209 Carroll St, Islamorada, FL 33036
0.05
$5,508,200
8
5.5
4,931
Off Market
81975 Old Hwy, Islamorada, FL 33036
0.09
$983,100
2
2
1,000
Off Market
82207 Old Hwy, Islamorada, FL 33036
0.10
$775,000
2
2
1,224
Recently Sold
82519 Old Hwy, Islamorada, FL 33036
0.13
$1,985,100
3
3
-
Off Market
153 List St, Islamorada, FL 33036
0.16
$593,600
1
1
525
Off Market
150 List St, Islamorada, FL 33036
0.20
$4,499,500
1
1
946
For Sale
81906-4 Overseas Other Fl Ky, Windley Key, FL 33036
0.20
$2,386,400
3
3.5
1,852
Off Market
100 List St, Islamorada, FL 33036
0.22
$5,400,000
3
2.5
3,019
Recently Sold
171 Ocean Ln, Islamorada, FL 33036
0.21
$3,873,300
4
4
3,330
Off Market
82238 Overseas Hwy, Islamorada, FL 33036
0.22
$8,289,600
6
6
6,866
Off Market

Local Information

  • Map ViewExplore the area around 209 E Carroll St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Lot Size
2.14 acres
Living Area
4,931 sqft
Price/Sqft
$765

About this House

FairWinds~A unique two acre oceanfront estate, discretely situated in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, along with many amenities. Inside the gates are enchantingly lush tropical gardens with carefully cultivated native specimens leading to the shimmering pastel blues of the Atlantic ocean, which gently caresses the 250+ feet of secluded sandy beach. This very special compound blends privacy with abundant recreational opportunities, ideally suited to create cherished memories with family and friends. FairWinds offers a grand main house, complete with a wrap-around porch, wide verandas and stunning ocean views, perfect for memorable gatherings of family and friends. Watch the sun rise beyond the historic Alligator Reef Lighthouse
209 E Carroll St, Islamorada, FL 33036 is a 8 bedroom, 6 bathroom, 4,931 sqft single-family home built in 2001. It last sold for $3,000,000 on Dec 18, 2023. It is currently off market. The Trulia Estimate is $3,769,900, with a rent estimate of $7,734/month.

Home Details for 209 E Carroll St

Interior Features

Heating & Cooling
Heating: Forced Air, GasAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In ClosetWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
ElevatorFloors: Tile

Exterior Features

Exterior Home Features
Roof: MetalDeckExterior: StuccoFoundation Type: SlabPatioPorchSprinkler System
Parking & Garage
Parking Spaces: 4

Property Information

Year Built
Year Built: 2001Year Updated: 1989
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 3

Lot Information

Lot Area: 2.14 acres

Mobile R/V

RV Parking
Rv Parking

Additional Information

On Site Laundry Available

Price and Tax history

DateEventPrice
Dec 18, 2023
Source: N/A
Sold
$3,000,000
Nov 15, 2023
Source: FLKMLS #606330
Pending
$5,500,000
Aug 15, 2023
Source: FLKMLS #606330
Listed For Sale
$5,500,000
Jul 24, 2023
Source: FLKMLS #604880
ListingRemoved
Apr 9, 2023
Source: FLKMLS #604880
Listed For Sale
$5,500,000

Market trends in Islamorada

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.09M
$8.17KMoM
Sale-to-List Price
—
Price per sq ft
$724
$14MoM
Available listings
159
2MoM

Around this home

What Locals Say about Islamorada

At least 24 Trulia users voted on each feature.

  • 88 % Say people would walk alone at night

  • 88 % Say parking is easy

  • 84 % Say it's dog friendly

  • 83 % Say yards are well-kept

  • 79 % Say car is needed

  • 72 % Say kids play outside

  • 70 % Say it's quiet

  • 67 % Say it's walkable to restaurants

  • 58 % Say they plan to stay for at least 5 years

  • 56 % Say there's holiday spirit

  • 55 % Say neighbors are friendly

  • 53 % Say there's wildlife

  • 44 % Say there are community events

  • 41 % Say it's walkable to grocery stores

  • 39 % Say streets are well-lit

  • 23 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • John Hermansen
    "Fishing tournaments and HOA lunches are nice. The marina is a great community and everyone on the airstrip are very kind. Great place for kids and dogs. "
    1
    Flag
  • Jnmarcil
    "The area is awesome. Safe, clean , everyone knows everyone and keep an eye out for our neighbors best place to live. "
    0
    Flag
  • Trulia User
    "Neighborhood feels safe and secure. I love the area. Live right near the Montessori school. Beware because there are sometimes fast drivers. "
    0
    Flag
  • Trulia User
    "Lots of grass to play in. Easy living in the Keys. Lots of places to run you dogs. Pebbles & Bambam enjoy it. "
    0
    Flag
  • Fabelomaribel
    "I've lived in this neighborhood for a while and the people are very nice I love my neighbor's the schools are closed by"
    1
    Flag
  • Cinnapep
    "Beautiful area with friendly people. Clean neighborhood and low crime rate. Very walkable with great galleries and restaurants. "
    0
    Flag
  • Jessica G.
    "I’ve lived here for almost 2 years now and i live net the boat ramp and everyone is very nice and the schools are close as they can be"
    0
    Flag
  • Jessica
    "It is near the high school and close to Winn Dixie along with close by gas stations .................."
    0
    Flag
  • Amie B.
    "we've lived her for 1 year and lovve it, beautiful ocean views and multi million dollar homes atl around. "
    0
    Flag
  • Lynne G.
    "Love it here in Safety Harbor. Everything about this home and neighborhood is wonderful. Kind neigbors, lovely views, best of Islamorada communities. Plenty to do if you are looking for it and plenty of peace & privacy at the same time. "
    0
    Flag
  • Lucytwo259
    "This is one of the best areas in Islamorada, It is a beautiful ocean-side location with easy ocean access. It is far enough away from the hustle and noise of the commercial area but not so far that it is inconvenient."
    0
    Flag
  • Kathy D.
    "Coral Harbour Club is located in the heart of Islamorada near shopping and dining."
    0
    Flag
  • Interested I. A.
    "Islamorada is a wonderful community with lots of things to do for all ages and lifestyles. Fishing, bird watching, hiking, swimming, snorkeling, kayaking, biking, running, great nightlife and restaurants. All around fun and relaxation!"
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 209 E Carroll St

  • What is 209 E Carroll St estimated to be worth?
    Trulia's estimated value for 209 E Carroll St in Islamorada, FL is $3,769,900.
  • What is the price history for 209 E Carroll St?
    209 E Carroll St in Islamorada, FL last sold for $3,000,000 in December 2023.
  • Is Islamorada a buyer's or seller's market?
    Islamorada is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Islamorada?
    The median sale price in Islamorada is $1.09M. That is up $8.17K from the prior month.
  • Does 209 E Carroll St have air conditioning?
    Yes, 209 E Carroll St in Islamorada, FL has air conditioning.
  • Does 209 E Carroll St have laundry facilities?
    Yes, 209 E Carroll St in Islamorada, FL has in-unit laundry.

Explore by feature - Pet Friendly

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Off Market Homes Near 209 E Carroll St

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