209 E Carroll St, Islamorada, FL 33036
OFF MARKET

209 E Carroll St
Islamorada, FL 33036

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

$3,538,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $19,648/mo*
Refinance Your Home

$3,538,500

Trulia Estimate
as of May 10, 2026
Est. Refi. Payment $19,648/mo*
Refinance Your Home
8 Beds
5.5 Baths
4,931 sqft
(on 2.14 acres)

Homes for sale near 209 E Carroll St

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Apartments for Rent

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Local Information

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

Description

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
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.

Home Highlights

Parking
No Info
Outdoor
Porch, Patio, Deck
View
No Info
HOA
None
Price/Sqft
No Info
Listed
No Info

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 History for 209 E Carroll St

DatePriceEventSource
12/18/2023$3,000,000Sold
N/A
11/15/2023$5,500,000PendingFLKMLS #606330
08/15/2023$5,500,000Listed For SaleFLKMLS #606330
07/24/2023ListingRemovedFLKMLS #604880
04/09/2023$5,500,000Listed For SaleKey West AOR #604880
02/16/2022ListingRemovedFLKMLS #594692
02/15/2021$7,900,000Listed For SaleFLKMLS #594692
02/15/2021ListingRemovedFLKMLS #590112
03/04/2020$7,900,000Listed For SaleAgent Provided
08/11/2009$712,500Sold
N/A
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Property Tax and Assessment

Year2025
Tax$23,740
Assessment$2,543,254
Home facts updated by county records

Comparable Sales for 209 E Carroll St

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
105 Carroll Street Upper Matecumbe Ky #6, Islamorada, FL
0.41
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
0.41
Single-Family Home
$1,700,000
03/30/26
4
4
2,728
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
81300 Old Hwy, Islamorada, FL
1.16
Single-Family Home
$6,500,000
07/07/25
4
3
3,138
81975 Old Hwy, Islamorada, FL
0.09
Single-Family Home
$750,711
08/25/25
2
2
1,000
82207 Old Hwy, Islamorada, FL
0.10
Single-Family Home
$610,000
10/01/25
2
2
1,224

Assigned Schools

These are the assigned schools for 209 E Carroll 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.

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

  • 66 % 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 there's wildlife

  • 54 % Say neighbors are friendly

  • 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

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
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  • 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
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  • 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
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  • 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

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Homes for rent near 209 E Carroll St

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Off Market Homes Near 209 E Carroll St

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Explore by feature

209 E Carroll St, Islamorada, FL 33036 is a 8 bedroom, 6 bathroom, 4,931 sqft single-family home built in 2001. This property is not currently available for sale. 209 E Carroll St was last sold on Dec 18, 2023 for $3,000,000. The current Trulia Estimate for 209 E Carroll St is $3,538,500.