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$1,499,000
Cudjoe Key, FL 33042
MLS# 619835
3 beds | 2 baths | 1434 sqft
1 / 52
Property 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. 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.
Details
Maps
Contract Information
Listing Board: Marathon/Lower Keys
As is Rght to Inspct: Yes
Species List: Yes
Current Price: $1,499,000
Listing Date: 2026-05-08
List Price: $1,499,000
Location, Tax & Legal
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
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
General Property Description
Realtor.COM Type: Residential - Single Family
Waterfront: Yes
Control Depth: 3
Lot Size: 60 X 100
Lot SqFt: 6000
Pool: No
Lot Sqft Source: Property Data Card
Total Units: 0
Acres: 0.14
SqFt Source: Property Data Card
Rentals Allowed: With Restrictions
Min Rental Days: 28
Style: Single Family
Year Built: 1999
Living Apx SqFt: 1434
Total Bedrooms: 3
Full Baths: 2
Total Baths: 2
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.
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Association Fee $: 0
Fee Includes
None: 1
Dockage
Dock Length: 46
Dock: Wood
Tax Exemptions
None: 1
Appliances
Dishwasher: 1
Dryer: 1
Range: 1
Refrigerator: 1
Washer: 1
Pets
Pets Allowed: 1
Cooling
Ceiling Fans(s): 1
Central Air: 1
Waterfront
Canal Front: 1
Waterview
Open Water View: 1
Interior Features
Smoke Alarms: 1
Property Condition
Updated/Remodeled: 1
Specialty Rooms
Utility Room: 1
Workshop: 1
Building Style
Above Flood: Unknown
Vehicle Storage
Covered Parking: 1
Open Parking: 1
RV Parking Open: 1
Trailer Storage: 1
Construction
CBS: 1
Land Size
Less Than 1/4 Acre: 1
Furnished
Negotiable: 1
Terms
Cash: 1
Conventional: 1
FHA: 1
VA: 1
Utilities
FKAA: 1
Municipal Sewer: 1
Water Separate Meter: 1
Porch/Balcony
Roof Top Deck: 1
Screened P/B: 1
Title
Title Ins - Buyer: 1
Exterior Features
Fencing: 1
Roof
Metal Roof: 1
Shutters
Panel: 1
Status Change Info
Status: Active
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.