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
Sold for $3,000,000
$3,000,000
209 E Carroll St, Islamorada, FL 33036
8beds
4,931sqft
SingleFamily
Built in 2001
2.14 Acres Lot
$3,769,900 Zestimate®
$608/sqft
$7,734 Estimated rent
Home value
$3,769,900
$3.20M - $4.45M
$7,734/mo
Zestimate® history
Owner options
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$7,734/mo
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$7,734/mo
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$20,233/mo
Est. payment
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$20,233/mo
Est. payment
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List your homeWhat's special
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Heating
- Forced air, Gas
Cooling
- Central
Appliances
- Included: Dishwasher, Dryer, Freezer, Microwave, Range / Oven, Refrigerator, Washer
Features
- Granite Counter Top, Split Bedroom, Window Treatments, Built-in Cabinets, Elevator, Foyer, Smoke Alarms, Storage, Walk-in Closet, Bar, Drapes/Blinds Incl, Pantry, Whirlpool Bath Tub, Wet Bar, Tray Ceilings
- Flooring: Tile
- Has fireplace: No
- Furnished: Yes
Interior area
- Total interior livable area: 4,931 sqft
Property
Parking
- Total spaces: 4
Features
- Exterior features: Stucco
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
Lot
- Size: 2.14 Acres
Details
- Parcel number: 00400930000000
- Zoning: R1 - Residential Single Family
Construction
Type & style
- Home type: SingleFamily
Materials
- Concrete Block
- Foundation: Slab
- Roof: Metal
Condition
- Updated/Remodeled
- Year built: 2001
Utilities & green energy
- Utilities for property: FKAA, Buyer to Verify, Municipal Sewer, Cable Available, Whole House Generatr, Propane
Community & HOA
Community
- Features: On Site Laundry Available
HOA
- Has HOA: Yes
- HOA fee: $2,149 monthly
Location
- Region: Islamorada
Financial & listing details
- Price per square foot: $608/sqft
- Tax assessed value: $2,543,254
- Annual tax amount: $23,740
Price history
| Date | Event | Price |
|---|---|---|
| 12/18/2023 | Sold | $3,000,000-45.5%$608/sqft |
Source: Public Record Report a problem | ||
| 11/15/2023 | Pending sale | $5,500,000$1,115/sqft |
Source: | ||
| 8/15/2023 | Listed for sale | $5,500,000$1,115/sqft |
Source: | ||
| 7/24/2023 | Listing removed | -- |
Source: | ||
| 4/9/2023 | Listed for sale | $5,500,000-30.4%$1,115/sqft |
Source: | ||
| 2/16/2022 | Listing removed | -- |
Source: | ||
| 2/15/2021 | Listed for sale | $7,900,000$1,602/sqft |
Source: | ||
| 2/15/2021 | Listing removed | -- |
Source: | ||
| 3/4/2020 | Listed for sale | $7,900,000+1008.8%$1,602/sqft |
Source: American Caribbean Real Estate - Islamorada #590112 Report a problem | ||
| 8/11/2009 | Sold | $712,500$144/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $23,740 +2.1% | $2,543,254 +1.5% |
| 2024 | $23,262 -6.2% | $2,505,567 +6.1% |
| 2023 | $24,793 +6.3% | $2,360,491 +10% |
| 2022 | $23,318 +17.8% | $2,145,901 +10% |
| 2021 | $19,799 +5.5% | $1,950,819 +10% |
| 2020 | $18,771 | $1,773,472 +10% |
| 2019 | $18,771 +15.7% | $1,611,774 +17.4% |
| 2018 | $16,229 +12.2% | $1,372,533 -7.6% |
| 2017 | $14,458 -3.9% | $1,485,240 +5.7% |
| 2016 | $15,050 +2% | $1,404,895 +17% |
| 2015 | $14,757 | $1,201,141 |
Find assessor info on the county website
Neighborhood: 33036
Nearby homes
- $4,500,0005 bd4 ba4.6k sqft209 E Carroll St, Islamorada, FL 33036Sold
- $749,8003 bd2 ba1.8k sqft193 Carroll St, Upper Matecumbe Key, FL 33036Off Market

- $1,250,0003 bd3 ba1.5k sqft191 Carroll St, Islamorada, FL 33036For Sale

- $1,250,0003 bd3 ba1.5k sqft189 Carroll St, Islamorada, FL 33036For Sale

- $1,644,7001 bd1 ba804 sqft198 Carroll St, Islamorada, FL 33036Off Market
- $5,519,0004 bd4 ba4.1k sqft199 Carroll St, Islamorada, FL 33036Off Market
- $907,3004 bd2 ba1.5k sqft181 Carroll St, Islamorada, FL 33036Off Market
- $3,182,0003 bd2 ba1.2k sqft183 Carroll St, Islamorada, FL 33036Off Market
Nearby schools
GreatSchools rating
- 10/10Plantation Key SchoolGrades: PK-8Distance: 7.3 mi
- 5/10Coral Shores High SchoolGrades: 9-12Distance: 7.5 mi
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Estimated market value
$3,769,900
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$3,769,900
- Florida
- Monroe County
- Islamorada
- 33036
- 209 E Carroll St