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$1,499,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,434 Sq. Ft.
  • Updated 1 hour ago
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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.

Full Property Details for 22939 Gasparilla Ln

General

  • Price: $1,499,000
  • Taxes: $7,973 (2025)
  • Status: Active
  • Type: Single Family
  • Source: 927
  • MLS ID: 619835
  • Updated: 5/13/2026
  • Added to Site: 6 day(s) ago

Interior

  • Interior Features: Workshop, Utility Room, Smoke Alarms
  • Appliances: Dishwasher, Dryer, Range, Refrigerator, Washer

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Exterior

  • Exterior Features: Fencing
  • Deck/Patio: Roof Top Deck, Screened
  • Porch/Patio/Deck: Roof Top Deck, Screened

Parking

  • Parking Features: Open, Covered

Location

  • Area: 07 - Cudjoe Key
  • County: Monroe
  • Subdivision: Cutthroat Harbor Est (23.0)
  • Driving Directions: US - turn ocean-side on Spanish Main Drive (MM23) RIGHT on Gasparilla House is on the right.

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Central air: Yes
  • Air Conditioning: Yes
  • Cooling Type: Central Air, Ceiling Fans(s)

Structural Information

  • Architectural Style: Above Flood
  • Construction Status: Updated/Remodeled
  • Construction: CBS
  • Roof: Metal
  • Windows/Doors: Shutters
  • Square Feet: 1,434
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1999
  • Property Condition: Updated/Remodeled

Lot Features

  • Property View: Open Water View
  • Lot Size (Acres): 0.14
  • Lot Size (Sq. Ft.): 6,000
  • Lot Size Source: Property Data Card
  • Lot Dimensions: 60 x 100
  • Zoning: IS - Improved Subivision District

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Canal Front

Financial Considerations

  • Tax Amount: $7,973.04
  • Tax Year: 2025
  • Terms: Cash, Conventional, VA Loan, FHA

Disclosures and Reports

  • Legal Description: BK 28 LT 5 CUTTHROAT HARBOR ESTATES CUDJOE KEY PB4-165
  • Flood Zone: VE-Yes2
  • APN: 00182700-000000

Listed by Keller Williams Key West Compass Realty, Donna Pezzi (305) 304-2602

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Listing agent

— 22939 Gasparilla Ln —

  • Donna Pezzi

    Keller Williams Key West Compass Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 22939 Gasparilla Ln

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Sugarloaf School
255 Crane Boulevard, Summerland Key, FL 33042
PK-83.4 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1220.2 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 22939 Gasparilla Ln Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/08/2026
Listed
$1,499,000
48.93%
MLS
12/28/2023
Sold
$1,006,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 22939 Gasparilla Ln

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,660
—
$820,808
2%
2024
$7,660
20%
$807,938
-3%
2023
$6,395
26%
$834,521
75%
2021
$5,074
-7%
$477,928
-22%
2022
$5,459
8%
$609,790
31%
2021
$5,074
—
$464,952
-1%
2019
$5,070
2%
$471,318
6%
2018
$4,956
3%
$446,497
2%
2017
$4,795
6%
$437,022
11%
2016
$4,521
2%
$392,919
7%
2015
$4,430
11%
$368,458
4%
2014
$4,009
-9%
$353,995
6%
2013
$4,388
—
$334,893
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 22939 Gasparilla Ln

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Keller Williams Key West Compass Realty, Donna Pezzi (305) 304-2602

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22939 Gasparilla Lane, Cudjoe Key, FL 33042 (MLS# 619835) is a Single Family property with 3 bedrooms and 2 full bathrooms. 22939 Gasparilla Lane is currently listed for $1,499,000 and was received on May 08, 2026. Want to learn more about 22939 Gasparilla Lane? Do you have questions about finding other Single Family real estate for sale in Cudjoe Key? You can browse all Cudjoe Key real estate or contact a Coldwell Banker agent to request more information.

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