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22939 Gasparilla Lane, Cudjoe Key, FL 33042

New Listing
$1,499,000
Property Type: Residential Bedrooms: 3 Baths: 2 Square Footage: 1,434 Lot Size (sq. ft.): 6,000 Status: Active
Current Price: $1,499,000 List Date: 5/09/2026 Last Modified: 5/09/2026

Overview

Description

Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfec ...

Listing Details MLS# 619835

Location, Tax & Legal

Street #
22939
Street Name
Gasparilla
Street Suffix
Lane
Key/Island
Cudjoe Key
State/Province
FL
Zip Code
33042
County
Monroe
Subdivision
Cutthroat Harbor Est (23.0)
Area
07 - Cudjoe Key
City
Cudjoe
Mile Marker
23
Marathon Neighborhood
N/A
Side
Ocean
Flood Zone
VE-12
Alternate Key #
1234672
Parcel #
00182700-000000
Zoning
IS - Improved Subivision District
Deed Restrictions
Unknown
Legal
BK 28 LT 5 CUTTHROAT HARBOR ESTATES CUDJOE KEY PB4-165
Taxes
7973.04
Tax Year
2025
Pub Sewer HkUp
Yes

Contract Information

Listing Board
Marathon/Lower Keys
As is Rght to Inspct
Yes
Species List
Yes

General Property Description

Realtor.COM Type
Residential - Single Family
Style
Single Family
Waterfront
Yes
Control Depth
3
Pool
No
Year Built
1999
Lot SqFt
6000
Lot Sqft Source
Property Data Card
Acres
0.14
Living Apx SqFt
1434
SqFt Source
Property Data Card
Total Bedrooms
3
Full Baths
2
Total Baths
2
Rentals Allowed
With Restrictions
Min Rental Days
28
Total Units
0

Association Info

Mandatory Home Owners Asc
No
1st Right of Refusal
No
Association Fee $
0

Dockage

Dock Length
46
Dock
Wood

More Information

Building Style

Above Flood
Unknown

Remarks & Misc

Remarks – Consumer
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.
Directions
US - turn ocean-side on Spanish Main Drive (MM23) RIGHT on Gasparilla House is on the right.

Fee Includes

None
Yes

Tax Exemptions

None
Yes

Appliances

Dishwasher
Yes
Dryer
Yes
Range
Yes
Refrigerator
Yes
Washer
Yes

Pets

Pets Allowed
Yes

Cooling

Ceiling Fans(s)
Yes
Central Air
Yes

Waterfront

Canal Front
Yes

Waterview

Open Water View
Yes

Interior Features

Smoke Alarms
Yes

Property Condition

Updated/Remodeled
Yes

Specialty Rooms

Utility Room
Yes
Workshop
Yes

Vehicle Storage

Covered Parking
Yes
Open Parking
Yes
RV Parking Open
Yes
Trailer Storage
Yes

Construction

CBS
Yes

Land Size

Less Than 1/4 Acre
Yes

Furnished

Negotiable
Yes

Terms

Cash
Yes
Conventional
Yes
FHA
Yes
VA
Yes

Utilities

FKAA
Yes
Municipal Sewer
Yes
Water Separate Meter
Yes

Porch/Balcony

Roof Top Deck
Yes
Screened P/B
Yes

Title

Title Ins - Buyer
Yes

Exterior Features

Fencing
Yes

Roof

Metal Roof
Yes

Shutters

Panel
Yes

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: Canal Front Waterview: Open Water View Property Condition: Updated/Remodeled Vehicle Storage: Covered Parking; Open Parking; RV Parking Open; Trailer Storage Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Utilities: FKAA; Municipal Sewer; Water Separate Meter Interior Features: Smoke Alarms Specialty Rooms: Utility Room; Workshop Appliances: Dishwasher; Dryer; Range; Refrigerator; Washer Exterior Features: Fencing Construction: CBS Shutters: Panel Roof: Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre Terms: Cash; Conventional; FHA; VA Title: Title Ins - Buyer
Listing Office: Keller Williams Key West Compass Realty
Last Updated: May - 09 - 2026
The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.
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