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
$3,662,300 Zestimate®
$608/sqft
$7,734 Estimated rent
Home value
$3,662,300
$3.15M - $4.28M
$7,734/mo
Zestimate® history
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$7,734/mo
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$7,734/mo
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$16,882/mo
Est. payment
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$16,882/mo
Est. payment
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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 & neighborhood
Community
- Community features: On Site Laundry Available
Location
- Region: Islamorada
HOA & financial
HOA
- Has HOA: Yes
- HOA fee: $2,149 monthly
Other
Other facts
- Vehicle Storage: Covered Parking, Guest Parking, Off Street Parking, Open Parking, Garage, RV Parking Open, Trailer Storage, Attached, Auto Door Opener, Detached
- Cooling/Heating: Central A/C, Ceiling Fans, Ductless A/C
- Porch/Balcony: Deck, Patio, Open Porch/Balcony
- Utilities: FKAA, Buyer to Verify, Municipal Sewer, Cable Available, Whole House Generatr, Propane
- Interior 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
- Appliances: Dishwasher, Dryer, Oven, Range, Refrigerator, Washer, Microwave, Disposal, Freezer, Wine Cooler, Ice Machine, More Appliances
- Windows/Doors: Sliding Glass Doors, Single Hung Windows, Aluminum Windows, Glass Doors, Impact Rstnce Window, Impact Rstnce Doors, Other Windows/Doors, Double Hung Windows
- Pets: Pets Allowed
- Exterior Features: Shed, Fencing, Landscape Lighting, Sprinkler System, Outdoor Shower, Chickee Hut, Fruit Tree(s), Water Display, Detached Guest Qtrs, Sandy Beach
- Shutters: Bahama, Panel, Accordion, Other
- SqFt Source: Tax Records
- Rentals Allowed: With Restrictions
- Construction: CBS
- Floor: Tile Floor, Marble
- Roof: Metal Roof
- Pub Sewer HkUp: Yes
- Furnished: Furniture Negotiable
- Pre-Wired: Cable
- Side: Ocean
- Specialty Rooms: Laundry Room, Utility Room, Workshop
- Security: Electric Gate
- Land Size: 2 Less Than 5 Acres
- Waterview: Open Water View, Ocean View
- Waterfront: Oceanfront
- Accessibility Feat: Elevator, Accessible, Grab Bars
- Key/Island: Upper Matecumbe Key Islamorada
- Zoning: R1 - Residential Single Family
- Vehicle Storage: Car(s): 4+
- Specialty Rooms: Guest/Servant Qtrs: Legal
- GF-Exterior Features: Xeriscaped
- Status: Active
- Tax Year: 2019
- Building Style: Above Flood: Unknown
- Property Condition: Updated/Remodeled
- Financial Status: Standard Sale: Yes
- Parcel #: 00400940-000000
- Add'l Parcel #1: 00400930-000000
- Add'l Parcel #2: 00096070-000000
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:  FLKMLS #606330 Report a problem | ||
| 8/15/2023 | Listed for sale | $5,500,000$1,115/sqft |
Source: FLKMLS #606330 Report a problem | ||
| 7/24/2023 | Listing removed | -- |
Source: FLKMLS #604880 Report a problem | ||
| 4/9/2023 | Listed for sale | $5,500,000-30.4%$1,115/sqft |
Source:  Key West AOR #604880 Report a problem | ||
| 2/16/2022 | Listing removed | -- |
Source: FLKMLS #594692 Report a problem | ||
| 2/15/2021 | Listed for sale | $7,900,000$1,602/sqft |
Source: FLKMLS #594692 Report a problem | ||
| 2/15/2021 | Listing removed | -- |
Source: FLKMLS #590112 Report a problem | ||
| 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 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
$3,662,300
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
$3,662,300
- Florida
- Monroe County
- Islamorada
- 33036
- 209 E Carroll St
Nearby cities
Nearby zip codes
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