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$2,795,000

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 3 Full Baths
  • 2,374 Sq. Ft.
  • Updated 3 hours ago
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'Turnkey Deepwater Boater's Retreat with Private Beach Access in the Heart of Islamorada' Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in Islamorada, this fully renovated 3-bedroom, 3.5-bath concrete residence delivers the ultimate Florida Keys lifestyle--where luxury, durability, and world-class boating converge. Built for peace of mind and longevity, the home features solid concrete construction and a concrete roof, offering superior storm resilience and insurance advantages rarely found in the Keys. Designed for serious boaters, the property boasts 90 feet of deepwater dockage with immediate access to both the bay and the Atlantic Ocean--no bridges, no delays, just open water within minutes. Inside, the home is completely turnkey, with updated finishes and a seamless indoor-outdoor flow ideal for entertaining or extended stays. Expansive balconies and a large outdoor patio overlook the wide canal, creating a private waterfront setting perfect for sunset dining or relaxing after a day on the water. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles -- an uncommon convenience in this area. What truly sets this property apart is access to a rare, highly coveted private beach area, widely regarded by locals as one of the finest in the Florida Keys, offering a unique blend of boating and beach lifestyle that is seldom available in a single property. Whether you're seeking a primary residence, a luxury second home, or an income-producing waterfront asset, this property delivers unmatched versatility and strong potential for high-end monthly rentals.

Full Property Details for 122 Court Contessa

General

  • Price: $2,795,000
  • HOA FEE: $42/month
  • HOA FEE FREQ.: Yearly
  • Taxes: $13,927 (2024)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 616500
  • Updated: 5/13/2026
  • Added to Site: 240 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Utility Room, Entrance Foyer, Walk-in Closet(s), Built-in Cabinets, Cathedral Ceilings, Drapes/Blinds Incl, Granite Counter Top, Pantry, Security System, Smoke Alarms, Split Bedroom, Storage, Window Treatments, Smart Thermostat
  • Appliances: Stainless Steel Appliance(s), Dishwasher, Disposal, Dryer, Freezer, Ice Machine, Microwave, More Appliances, Oven, Range, Refrigerator, Washer, Wine Cooler
  • Flooring: Tile, Concrete

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 3

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Manager on Premises, Fire Hydrant, Community Dockage, Community Boat Ramp, Beach
  • Security/Safety: Other

Exterior

  • Exterior Features: Rain Gutters, Lighting, Outdoor Shower, Sandy Beach, Storage
  • Deck/Patio: Open Porch/Balcony, Deck, Patio
  • Porch/Patio/Deck: Open Porch/Balcony, Deck, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Parking Features: Open, Guest, Off Street, Covered, Attached, Garage Door Opener

Location

  • Area: 22 - Lower Matecumbe
  • County: Monroe
  • Subdivision: Port Antigua (74.5)
  • Driving Directions: US1 to Gulfview, turn right onto Ponce de Leon. Go down to Biscayne Blvd, then turn right until the end of the road. Court Contessa is located on the right-hand side at the end of the cul-de-sac

Community

  • Assoc. Fees Include: Common Area Mnt
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Wall/Window Unit(s), Ductless, Central Air, Ceiling Fans(s)
  • Heating Type: Central, Exhaust Fan

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: CBS, Concrete
  • Roof: Concrete
  • Windows/Doors: Awning Windows, Impact Rstnce Doors, Impact Rstnce Window, Sliding Glass Doors
  • Square Feet: 2,374
  • Sq. Ft. Source: Tax Records
  • Year Built: 1991
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Canal, Ocean, Bay
  • Lot Size (Acres): 0.13
  • Lot Size (Sq. Ft.): 5,788
  • Zoning: R1 - Residential Single Family

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Bay Front, Canal Front

Financial Considerations

  • Association Fee: Yes
  • Association Fee: $500
  • Assoc Fee Freq.: Yearly
  • Tax Amount: $13,927.23
  • Tax Year: 2024
  • Terms: Assumable, Cash, Conventional, VA Loan, FHA

Disclosures and Reports

  • Legal Description: LT 291 PORT ANTIGUA PLAT NO 5-6 PB6-25 OR537-302 OR563-1055 OR798-1172 OR1065-1871 OR1074-861 OR1173-271 OR1171-912 OR14
  • Flood Zone: AE
  • APN: 00394489-009400

Listed by The Keyes Company, Lourdes Martin-Rosa (305) 505-8050

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Listing agent

— 122 Court Contessa —

  • Lourdes Martin-Rosa

    The Keyes Company

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 122 Court Contessa

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-814.8 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1269.2 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 122 Court Contessa Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/22/2026
Price Reduced
$2,795,000
-3.62%
MLS
1/05/2026
Price Reduced
$2,900,000
-3.33%
MLS
9/15/2025
Listed
$3,000,000
300%
MLS
4/10/2014
Sold
$750,000
—
Public Record
Get Price Alerts and Save Property
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 for 122 Court Contessa

Year
Property Taxes
Change
Tax Assessment
Change
2024
$13,927
—
$1,938,047
3%
2024
$13,927
11%
$1,875,896
22%
2023
$12,522
25%
$1,536,920
63%
2021
$10,049
-12%
$940,571
-29%
2022
$11,369
13%
$1,320,754
45%
2021
$10,049
10%
$910,225
10%
2019
$9,169
4%
$828,417
4%
2018
$8,794
8%
$796,117
6%
2017
$8,169
2%
$749,635
9%
2016
$7,973
7%
$686,448
6%
2015
$7,442
-8%
$647,460
-8%
2014
$8,114
8%
$705,728
10%
2013
$7,494
—
$641,571
—
View All
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 for 122 Court Contessa

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NMLS#: 1598647

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Listed by The Keyes Company, Lourdes Martin-Rosa (305) 505-8050

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122 Court Contessa, Upper Sugarloaf Key, FL 33036 (MLS# 616500) is a Single Family property with 3 bedrooms and 3 full bathrooms. 122 Court Contessa is currently listed for $2,795,000 and was received on September 15, 2025. Want to learn more about 122 Court Contessa? Do you have questions about finding other Single Family real estate for sale in Upper Sugarloaf Key? You can browse all Upper Sugarloaf Key real estate or contact a Coldwell Banker agent to request more information.

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