NEW 15 HRS AGO

For sale

$9,999,000

Est. $69,019/mo —

•

3,622

sq ft

21966 Raffy Rd, Cudjoe Key, FL 33042

About this home

RARE WATERFRONT ESTATE WITH TWO RESIDENCES ON CUDJOE KEY! Discover Casa Aqua, an extraordinary Spanish Mediterranean estate nestled among acres of native hardwood hammock along the Atlantic Ocean. Offering exceptional privacy, breathtaking open water views, and spectacular sunsets, this secluded island retreat includes two residences totaling 3,622 sq. ft. of living space. The 3,024 sq. ft. main residence features 5 bedrooms, 3.5 baths, including a Primary Suite, second-floor Bedroom Suite, and Loft Bedroom Suite. A separate 598 sq. ft. , 1-bedroom, 1-bath guest cottage offers a private retreat with stunning panoramic water views. Elevated bridge walkways connect the residences, creating a truly unique island setting. Outdoors, enjoy a heated saltwater pool and spa overlooking the ocean, surrounded by lush tropical landscaping and the natural beauty of the Florida Keys. Explore winding nature trails through native vegetation, launch a kayak from your own shoreline, or head out on the water from the private dock. Located along Cutthroat Harbor, with Looe Key Reef just offshore, this exceptional property offers incredible opportunities for boating, fishing, snorkeling, and exploring the surrounding waters. Whether envisioned as a private family compound, secluded coastal getaway, or investment opportunity, Casa Aqua presents a rare chance to own a truly distinctive piece of the Florida Keys paradise!

Single-familyProperty Type

2005Year Built

5.12 acresLot Size

$2,761Price/Sq.Ft.

4 spacesParking

Listed by Lisa Ferringo and Associates Ferringo • Coldwell Banker Schmitt Real Estate Co

Listed by Debra Farrell • Island Welcome Real Estate

Listing updated: Nov 5, 2026 at 02:24am

Redfin checked: 2 minutes ago

•Source:FLKMLS #621938

Payment calculator

$69,019 per month

Principal and interest$53,892

Property taxes

$1,045

HOA dues

Home insurance

$14,082

Utilities

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Open houses

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Nearby open houses (6)

OPEN TODAY, 2PM TO 5PM
$495,000
Land— sq ft
Oharas Key Street Gulf, Saddlebunch, FL 33040
Listed 350 days
OPEN FRI, 4PM TO 5:30PM
$700,000
3 beds2 baths1,316 sq ft
29160 Primrose Ln, Big Pine Key, FL 33043
0.23 acre lot • Garage • Built 1996
OPEN SAT, 10AM TO 12PM3D WALKTHROUGH
$1,399,000
4 beds3 baths2,242 sq ft
27383 Saint Martin Ln, Ramrod Key, FL 33042
0.28 acre lot • Garage • Built 1998
OPEN SAT, 11AM TO 2PM
$680,000
3 beds3 baths1,152 sq ft
74 Pelican Ln, Big Pine Key, FL 33043
6,000 sq ft lot • Built 1988 • Listed 41 days
OPEN SAT, 11AM TO 1PM
$998,000
3 beds2 baths1,225 sq ft
83 Sugarloaf Dr, Sugarloaf Key, FL 33042
0.49 acre lot • Garage • Pool
OPEN NOV 14, 11AM TO 3PM
$1,970,000
3 beds2 baths1,849 sq ft
1733 Sunrise Dr, Big Pine Key, FL 33043
0.26 acre lot • 4 parking spots • Pool
(305) 598-5488

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Around this home

Schools

K - 12
Preschool & daycare

Sugarloaf School

Public PreK-8 • Assigned • 2.4mi

6/10

Key West High School

Public 9-12 • Assigned • 19.4mi

3/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

21966 Raffy Rd · $9,999,000

DAYS ON MARKET

The average home goes pending in 145 days.

SALE-TO-LIST

Most homes are selling 6% below list price.

LIST PRICE

Median sale price in this area is $1,262,390. (87% lower than this home)

PRICE DROP

14% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Cathedral ceilings
Entrance foyer
Elevator
Storage
Walk-in closet
Bar
Built-in features
Granite countertops
Window blinds and treatments
Unfurnished

Bathrooms
4 full bathrooms
1 half bathroom

Kitchen
Dishwasher
Refrigerator
Oven
Microwave
Disposal
Freezer
Wine cooler
Ice maker
Stainless steel appliances
Pantry

Laundry & utility
Laundry room
Washer
Dryer

Flooring
Tile
Marble

Heating & cooling
Central air
Ductless cooling
Ceiling fans

Sale and tax history for 21966 Raffy Rd

Sale History
Tax History

Date

Event

Price

FLKMLS #621938

Nov 4, 2026

Listed

$9,999,000

$2,761/sq ft

FLKMLS #110953

Nov 23, 2015

Listing Removed

—

Jun 1, 2009

Listed

$900,000

$248/sq ft

FLKMLS #120924

May 29, 2015

Listing Removed

—

Jan 12, 2015

Listed

$3,998,000

$1,104/sq ft

FLKMLS #115196

Oct 10, 2011

Listing Removed

—

Aug 17, 2011

Listed

$3,900,000

$1,077/sq ft

FLKMLS #114959

Oct 10, 2011

Listing Removed

—

Jun 22, 2011

Listed

$2,999,900

$828/sq ft

FLKMLS #113935

Oct 10, 2011

Listing Removed

—

Nov 29, 2010

Listed

$4,500,000

$1,242/sq ft

FLKMLS #110955

Nov 20, 2009

Listing Removed

—

Jun 1, 2009

Listed

$4,500,000

$1,242/sq ft

Public Records

Sep 6, 1988

Sold

$55,000

$15/sq ft

Year

Property tax

Land + Additions

Assessment*

2025

$12,542 (+2.7%)

$388,714 + $995,798

$1,384,512

2024

$12,207 (+4.5%)

$381,243 + $1,002,166

$1,383,409

2023

$11,686 (+0.3%)

$343,888 + $983,250

$1,327,138

2022

$11,647 (+5.0%)

$328,947 + $990,971

$1,319,918

2021

$11,096 (−2.4%)

$299,063 + $872,254

$1,171,317

2020

$11,368 (+7.7%)

$299,063 + $890,036

$1,189,099

2019

$10,554 (−2.2%)

$299,063 + $890,036

$1,189,099

2018

$10,796 (+1.3%)

2017

$10,662 (+9.1%)

2015

$9,773 (−0.5%)

2014

$9,820

Public record

Public record
Zoning

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

2.28 Acres

Year renovated

2013

Finished Sq. Ft.

3,024

Unfinished Sq. Ft.

—

Total Sq. Ft.

3,024

Year built

2005

Style

Single Family Residential

County

Monroe County

APN

2966 28 00175370000100

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Sep 17, 2026.

Suburban Residential District

The purpose of the SR district is to establish areas of low- to medium-density residential uses characterized principally by single-family detached dwellings. This district is predominated by development; however, natural and developed open space creates an environment defined by plants, spaces and over-water views.

Zone overlays

Industrial District

Permitted uses

Include but are not limited to:

Housing-Multiple units
Infrastructure
Park & open space

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

Heat Factor

We're working on getting current and accurate heat risk information for this home.

10/10 Wind Factor

99% chance of strong winds in next 30 years

1/10 Air Factor

0 unhealthy days expected this year, 0 days in 30 years

Provided by First Street

Historical weather

Cudjoe Key, FL • 33042

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 10 hours in June and 7.3 hours in December, placing it above the U.S. average for solar exposure.

10 hrs

7.3 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 21966 Raffy Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $900,000 and $5,000,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $900K to $5.0M.

SOLD AUG 6, 2026
$1,000,000 Last sold price
4 beds3 baths2,448 sq ft
165 Cutlass Ln, Cudjoe Key, FL 33042
$2353/sq ft
smaller lot
14 years older
SOLD JUN 15, 2026
$2,500,000 Last sold price
3 beds2 baths1,714 sq ft
653 Sawyer Dr, Cudjoe Key, FL 33042
$1302/sq ft
smaller lot
10 years older
SOLD JUN 1, 2026
$2,675,000 Last sold price
4 beds3 baths2,951 sq ft
20844 W 4Th Ave, Cudjoe Key, FL 33042
$1855/sq ft
smaller lot
8 years older
SOLD SEP 1, 2026
$5,000,000 Last sold price
4 beds3.5 baths3,208 sq ft
1046 Flagship Dr, Summerland Key, FL 33042
$1202/sq ft
smaller lot
4 years older
SOLD JUL 2, 2026
$900,000 Last sold price
3 beds2 baths2,198 sq ft
21073 7th Ave, Cudjoe Key, FL 33042
$2352/sq ft
smaller lot
30 years older
SOLD JUL 28, 2026
$2,750,000 Last sold price
4 beds2 baths1,917 sq ft
1044 Lagoon Dr, Summerland Key, FL 33042
$1326/sq ft
smaller lot
26 years older