122 Court Contessa, Matecumbe Key, FL 33036
What's special
'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.
- 343 days |
- 900 |
- 29 |
Travel times
Living Room
Kitchen
Bedroom
Zillow last checked:
Listing updated:
Lourdes Martin-Rosa 305-505-8050,
The Keyes Company
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 3
- Full bathrooms: 3
Bedroom 1
- Level: Second
Bedroom 2
- Level: Third
Bedroom 3
- Level: Third
Half bathroom
- Level: Main
Full bathroom
- Level: Second
Full bathroom
- Level: Third
Full bathroom
- Level: Third
Dining room
- Level: Second
Family room
- Level: Second
Kitchen
- Level: Second
Other
- Description: Estimated SQFT
- Level: Main
- Area: 143 Square Feet
- Dimensions: 13 x 11
Other
- Level: Second
Heating
- Has Heating (Unspecified Type)
Cooling
- Central Air, Wall/Window Unit(s), Ceiling Fans(s), Ductless
Appliances
- Included: More Appliances, Washer, Dryer, Dishwasher, Refrigerator, Range, Oven, Microwave, Disposal, Freezer, Ice Maker, Wine Cooler, Stainless Steel Appliance(s)
- Laundry: Laundry Room
Features
- Smart Thermostat, Built-in Features, Granite Counters, Storage, Walk-in Closet(s)
- Flooring: Tile, Concrete
Interior area
- Total structure area: 2,374
- Total interior livable area: 2,374 sqft
Property
Parking
- Parking features: Attached, Garage Door Opener, Open, Storage
- Has attached garage: Yes
- Has uncovered spaces: Yes
Features
- Patio & porch: Open Porch/Balcony, Deck, Patio
- Exterior features: Rain Gutters, Lighting, Outdoor Shower, Sandy Beach, Storage
- On waterfront: Yes
Lot
- Size: 5,662 Square Feet
Details
- Parcel number: 00394489009400
- Zoning: R1 - Residential Single Family
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS, Concrete
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1991
Utilities & green energy
- Utilities for property: Cable Available
Community & HOA
Community
- Features: Community Dockage, Community Boat Ramp, Manager on Premises, Fire Hydrant, Beach
- Security: Other, Security System
- Subdivision: Port Antigua (74.5)
HOA
- Has HOA: No
- Services included: Common Area Mnt
- HOA fee: $500 annually
Location
- Region: Matecumbe Key
Financial & listing details
- Price per square foot: $1,154/sqft
- Tax assessed value: $1,938,047
- Annual tax amount: $13,927
- Date on market: 9/15/2025
- Listing terms: Assumable,Cash,Conventional,FHA
Price history
| Date | Event | Price |
|---|---|---|
| 8/18/2026 | Price change | $2,740,000-0.4%$1,154/sqft |
Source:  FLKMLS #616500 Report a problem | ||
| 6/22/2026 | Price change | $2,750,000-1.6%$1,158/sqft |
Source:  MIAMI #A11857499 Report a problem | ||
| 4/22/2026 | Price change | $2,795,000-3.6%$1,177/sqft |
Source:  Key West AOR #616500 Report a problem | ||
| 1/5/2026 | Price change | $2,900,000-3.3%$1,222/sqft |
Source: Key West AOR #616500 Report a problem | ||
| 9/2/2025 | Price change | $3,000,000+0%$1,264/sqft |
Source: MIAMI #A11857499 Report a problem | ||
| 8/20/2025 | Listed for sale | $2,999,995+0%$1,264/sqft |
Source: MIAMI #A11857499 Report a problem | ||
| 7/31/2025 | Listing removed | $2,999,987$1,264/sqft |
Source: Key West AOR #614222 Report a problem | ||
| 6/14/2025 | Price change | $2,999,987-4.8%$1,264/sqft |
Source: FLKMLS #614222 Report a problem | ||
| 6/4/2025 | Price change | $3,150,000-2.5%$1,327/sqft |
Source: FLKMLS #614222 Report a problem | ||
| 5/17/2025 | Price change | $3,230,000-1.5%$1,361/sqft |
Source: Key West AOR #614222 Report a problem | ||
| 3/18/2025 | Listed for sale | $3,280,000-2.1%$1,382/sqft |
Source: Key West AOR #614222 Report a problem | ||
| 2/15/2025 | Listing removed | $3,350,800$1,411/sqft |
Source: Key West AOR #610903 Report a problem | ||
| 1/16/2025 | Price change | $3,350,800-1.4%$1,411/sqft |
Source: Key West AOR #610903 Report a problem | ||
| 1/4/2025 | Price change | $3,400,000-2%$1,432/sqft |
Source: Key West AOR #610903 Report a problem | ||
| 12/2/2024 | Price change | $3,470,000-0.7%$1,462/sqft |
Source: Key West AOR #610903 Report a problem | ||
| 7/26/2024 | Listed for sale | $3,495,000+366%$1,472/sqft |
Source: Key West AOR #610903 Report a problem | ||
| 4/11/2014 | Sold | $750,000-11.7%$316/sqft |
Source: FLKMLS #548453 Report a problem | ||
| 2/25/2014 | Pending sale | $849,000$358/sqft |
Source: CENTURY 21 Schwartz Realty #548453 Report a problem | ||
| 12/4/2013 | Price change | $849,000-2.3%$358/sqft |
Source: CENTURY 21 Schwartz Realty #548453 Report a problem | ||
| 12/3/2013 | Price change | $869,000+2.4%$366/sqft |
Source: CENTURY 21 Schwartz Realty #548453 Report a problem | ||
| 11/15/2013 | Price change | $849,000-2.3%$358/sqft |
Source: Schwartz Property Sales #548453 Report a problem | ||
| 2/24/2013 | Price change | $869,000-3.3%$366/sqft |
Source: CENTURY 21 Schwartz Realty #548453 Report a problem | ||
| 5/5/2011 | Listed for sale | $899,000-8.7%$379/sqft |
Source: Schwartz Property Sales #548453 Report a problem | ||
| 3/22/2011 | Listing removed | $985,000$415/sqft |
Source: Schwartz Property Sales #548453 Report a problem | ||
| 7/3/2010 | Listed for sale | $985,000-4.7%$415/sqft |
Source: Schwartz Property Sales, Inc. #548453 Report a problem | ||
| 9/20/2004 | Sold | $1,034,000+233.5%$436/sqft |
Source: Public Record Report a problem | ||
| 1/21/1997 | Sold | $310,000$131/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,991 +7.6% | $1,377,090 +10% |
| 2024 | $13,927 +11.2% | $1,251,900 +10% |
| 2023 | $12,522 +10.1% | $1,138,091 +10% |
| 2022 | $11,369 +13.1% | $1,034,628 +10% |
| 2021 | $10,049 +2.6% | $940,571 +3.3% |
| 2020 | $9,796 | $910,225 +9.9% |
| 2019 | $9,796 +6.8% | $828,417 +4.1% |
| 2018 | $9,169 +4.3% | $796,117 +6.2% |
| 2017 | $8,794 +7.7% | $749,635 +9.2% |
| 2016 | $8,169 +2.5% | $686,448 +6% |
| 2015 | $7,973 | $647,460 |
Find assessor info on the county website
Monthly payment
Estimated market value
$2,561,200
$2.43M - $2.69M
$6,686/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.