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$2,199,000 Contingent
Property Description
MOTIVATED SELLERS! The sea writes the script at this 3 bed, 3 bath oceanfront retreat on the most highly sought after neighborhoods on Summerland Key, and it stands in a class of its own. Western exposure delivers nightly golden-hour performances over the Atlantic, while deep-draft boating--among the best this side of the 7-Mile Bridge--begins right from your backyard. You'll love deep channel access to the Atlantic AND the Gulf of America! Inside, a wide-open floor plan crowned by cathedral ceilings, terracotta floors warming space throughout, and wall-to-wall sliders framing the Atlantic like a moving piece of art. A custom infinity-edge pool with in-water seating and sun shelf creates the perfect transition between home and horizon. Heated or chilled for year round comfort. The chef's kitchen impresses with elevated appliances including a 36' Wolf gas range, wine chiller, and twin beer taps. Relish the Keys breeze from the lanai and enjoy your morning coffee watching Summerland Cove wake up. End your day with alfresco dinning and famous Keys sunsets. A pre-FIRM lower level offers convenient guest quarters, an important Keys commodity. There's also flexible options for a pool house, tackle room, or storage - your choice. Plus a deep 1-car garage! A well maintained 10,000-lb boat lift--easily modified for larger vessels--completes the ideal waterfront lifestyle. Fuel your boat at Venture Out Marina less than two miles away from your seawall. With Niles Channel providing a 40-foot vertical bridge clearance, the highest in the Lower Keys, your Ocean or Gulf boating options are limitless. With just under 2,200 sq ft of living space- and backed by the security of a whole-house generator and whole-house water filter - this property embodies the rarest blend of comfort, craftsmanship, and blue-water possibility. Discover why Summerland Key remains the unsung hero of the Lower Keys--before opportunities like this are simply untouchable.
Full Property Details
Full Property Details for 556 E Caribbean Dr
General
- Price: $2,199,000
- HOA FEE: $2/month
- HOA FEE FREQ.: Yearly
- Taxes: $14,533 (2024)
- Status: Contingent
- Type: Single Family
- Source: 927
- MLS ID: 617652
- Updated: 5/13/2026
- Added to Site: 155 day(s) ago
Interior
- Interior Features: Workshop, Utility Room, Built-in Cabinets, Cathedral Ceilings, Granite Counter Top, Wired for Sound
- Appliances: Stainless Steel Appliance(s), Dishwasher, Dryer, Freezer, Gas Appliances, Microwave, Oven, Range, Refrigerator, Washer, Wine Cooler
- Flooring: Tile, Laminate
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
Other Rooms
- Laundry: Laundry Room
Additional Information
- Shared Amenities: Airport/Runway
- Pool: Yes
- Pool Description: Concrete, In Ground
Exterior
- Exterior Features: Rain Gutters, Outdoor Shower, Storage
- Deck/Patio: Open Porch/Balcony, Screened
- Porch/Patio/Deck: Open Porch/Balcony, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Parking Features: Off Street, Attached
Location
- Area: 08 - Summerland Key
- County: Monroe
- Subdivision: Summerland Key Cove (25.0)
Community
- Assoc. Fees Include: None
- Pets Allowed: Yes
Heating & Cooling
- Central air: Yes
- Air Conditioning: Yes
- Cooling Type: Wall/Window Unit(s), Heat Pump, Central Air, Ceiling Fans(s)
Structural Information
- Architectural Style: Above Flood
- Construction: CBS, Combo Construction, Frame
- Roof: Metal
- Windows/Doors: Double Hung Windows, Shutters
- Square Feet: 2,167
- Sq. Ft. Source: Property Data Card
- Year Built: 1974
Lot Features
- Property View: Open Water View, Ocean
- Lot Size (Acres): 0.15
- Lot Size (Sq. Ft.): 6,600
- Zoning: IS - Improved Subivision District
Water Features
- Water Front: Yes
- Water View: Yes
- Water Front Desc.: Oceanfront, Open Water
Financial Considerations
- Association Fee: Yes
- Association Fee: $25
- Assoc Fee Freq.: Yearly
- Tax Amount: $14,533.02
- Tax Year: 2024
Disclosures and Reports
- Legal Description: Bk 1 Lt 11 And Portion Of Land Lying Swly Summerland Key Cove Addition No 6 Pb5-41 Summerland Key
- Flood Zone: AE, VE, AE
- APN: 00192780-000000
Listed by Berkshire Hathaway HomeServices Knight & Gardner Realty, Angelina Will (305) 489-1984
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Schools
Schools serving 556 E Caribbean Dr
School District:Monroe County School District, Middle Torch Key, FL
| Name | Grades | Distance |
|---|---|---|
Sugarloaf School 255 Crane Boulevard, Summerland Key, FL 33042 | PK-8 | 5.3 mi |
Key West High School 2100 Flagler Avenue, Key West, FL 33040 | 9-12 | 22 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 556 E Caribbean Dr
Date
Details
Price
Change
Source
12/09/2025
Listed
$2,199,000
103.61%
MLS
8/21/2019
Sold
$1,080,000
—
Public Record
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Tax History
Tax History for 556 E Caribbean Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,533
—
$1,713,312
3%
2024
$14,533
-6%
$1,665,027
-4%
2023
$15,429
78%
$1,733,716
90%
2021
$8,667
3%
$912,786
-3%
2022
$8,377
-3%
$940,169
7%
2021
$8,667
122%
$876,466
127%
2019
$3,896
—
$385,612
2%
2018
$3,914
3%
$378,422
2%
2017
$3,807
-1%
$370,639
2%
2016
$3,829
-3%
$363,016
1%
2015
$3,933
-3%
$360,493
1%
2014
$4,048
-1%
$357,632
1%
2013
$4,097
—
$352,347
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 556 E Caribbean Dr
556 E Caribbean Drive, Summerland Key, FL 33042 (MLS# 617652) is a Single Family property with 3 bedrooms and 3 full bathrooms. 556 E Caribbean Drive is currently listed for $2,199,000 and was received on December 09, 2025. Want to learn more about 556 E Caribbean Drive? Do you have questions about finding other Single Family real estate for sale in Summerland Key? You can browse all Summerland Key real estate or contact a Coldwell Banker agent to request more information.
