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For sale

122 Court Contessa

Islamorada, FL 33036

$2,740,000

$1,154/ft²

3Beds
3.5Baths
2,374Sq ft
2021Year built
Single-family homeType

About this home

Rarely available turnkey Deepwater Boater's retreat with a Private Bayside beach in the heart of the fishing capital of the world. Tucked away on a quiet cul-de-sac in one of the most desirable enclaves in the Florida Keys, 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 FT of deepwater dockage with immediate access to both the bay and the Atlantic Ocean - NO BRIDGES, no delays, just open water within minutes. The home is completely updated with a seamless indoor-outdoor flow ideal for entertaining or extended stays. The oversized paved driveway provides ample parking for guests, trailers, or multiple vehicles - an uncommon convenience in this area. What truly sets this home apart is access to a rare, highly coveted private bayside beach, 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.

Features

  • Waterfront

Property details

Listing

MLS #
A12073183
Status
For sale
Listed on
Aug 18, 2026
Days on market
9 days
Listing data updated
Aug 18, 2026

Interior

Beds
3
Baths
3.5
Living area
2,374 ft²
Price per ft²
$1,154/ft²

Building & community

Type
Single-family home
Year built
2021
HOA fee
$42/mo
County
Monroe

Lot & exterior

Lot size
5,788 ft²
Waterfront
Yes

Days on market, price per ft² and the monthly HOA amount are calculated by this site from the MLS data shown; the association fee is normalized to a monthly figure.

What's nearby

Transit
MILE MARKER 74 ISLAMORADA · 0.3 mi away

Straight-line distances · Sources: NCES/FL DOE, GTFS Miami-Dade and Broward, OpenStreetMap

True monthly cost

Mortgage (principal & interest)
$13,855
Property taxes (est.)
$2,512
Home insurance (est.)
$2,055
Flood insurance (est.)
HOA fee
$42

Estimated total$18,464*/mo

* Some cost lines aren't available yet for this listing; the total shown is incomplete.

Based on 20% down, a 6.5% rate and a 30-year loan, plus this home's estimated Florida carrying costs. All figures are illustrative estimates — not quotes, not financial or insurance advice.

Sources: flood zone — FEMA National Flood Hazard Layer; mortgage, taxes and insurance figures — this site's own estimates; HOA / CDD — as reported for this listing.

What will this home really cost you?

Location

Mortgage calculator

$13,855/moEstimated principal & interest. Taxes, insurance, and HOA are not included. This is an estimate, not a quote or financial advice.

Equal Housing Opportunity

This listing is courtesy of The Keyes Company.

Lourdes Martin-Rosa · 305-505-8050 · lmrosa@me.com · 954-966-0631

Data deemed reliable, but is not guaranteed accurate by MIAMI REALTORS®.

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