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.
Under contract
$1,399,000
22939 Gasparilla Ln, Cudjoe Key, FL 33042
3beds
1,434sqft
Single Family Residence
Built in 1999
6,098 Square Feet Lot
$-- Zestimate®
$976/sqft
$-- HOA
What's special
New metal roofCovered parkingRich wooden ceilingsRooftop deckUnforgettable ocean vistasOpen living spacesFenced grounds
- 159 days
- 117
- 4
Zillow last checked:
Listing updated:
Listed by:
Donna Pezzi 305-304-2602,
Keller Williams Key West Compass Realty
Source: FLKMLS,MLS#: 619835
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Bedroom 1
- Description: Bedroom - canal side
- Level: Main
- Area: 105.67 Square Feet
- Dimensions: 10.75 x 9.83
Bedroom 2
- Description: Middle Bedroom
- Level: Main
- Area: 88.46 Square Feet
- Dimensions: 11.67 x 7.58
Bedroom 3
- Description: Bedroom - street side
- Level: Main
- Area: 113.78 Square Feet
- Dimensions: 11.67 x 9.75
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Dryer, Dishwasher, Refrigerator, Range
Features
- Flooring: Vinyl
Interior area
- Total structure area: 1,434
- Total interior livable area: 1,434 sqft
Property
Parking
- Parking features: Open, RV Access/Parking, Storage
- Has uncovered spaces: Yes
Features
- Patio & porch: Roof Top Deck
- Exterior features: Storage
- Fencing: Fenced
- On waterfront: Yes
Lot
- Size: 6,098 Square Feet
- Dimensions: 60 X 100
Details
- Parcel number: 00182700000000
- Zoning: IS - Improved Subivision District
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1999
Utilities & green energy
- Utilities for property: Water Separate Meter
Community & HOA
Community
- Subdivision: Cutthroat Harbor Est (23.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Cudjoe Key
Financial & listing details
- Price per square foot: $976/sqft
- Tax assessed value: $820,808
- Annual tax amount: $7,973
- Date on market: 5/9/2026
- Listing terms: Cash,Conventional,FHA
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 9/18/2026 | Contingent | $1,399,000$976/sqft |
Source: | ||
| 7/1/2026 | Price change | $1,399,000-6.7%$976/sqft |
Source: | ||
| 5/9/2026 | Listed for sale | $1,499,000+48.9%$1,045/sqft |
Source: | ||
| 12/28/2023 | Sold | $1,006,436-12.4%$702/sqft |
Source: | ||
| 11/13/2023 | Contingent | $1,149,000$801/sqft |
Source: | ||
| 10/23/2023 | Price change | $1,149,000-4.3%$801/sqft |
Source: | ||
| 6/6/2023 | Listed for sale | $1,200,000+66.9%$837/sqft |
Source: | ||
| 10/1/2020 | Listing removed | $719,000$501/sqft |
Source: Century 21 Island Life - Key West #588966 Report a problem | ||
| 2/7/2020 | Price change | $719,000-4%$501/sqft |
Source: CENTURY 21 Island Life #588966 Report a problem | ||
| 1/4/2020 | Listed for sale | $749,000+35%$522/sqft |
Source: Century 21 Island Life - Key West #588966 Report a problem | ||
| 5/31/2019 | Sold | $555,000$387/sqft |
Source: | ||
| 4/17/2019 | Price change | $555,000-5.5%$387/sqft |
Source: Coastal Collection Real Estate Inc. #584802 Report a problem | ||
| 4/12/2019 | Price change | $587,000-0.8%$409/sqft |
Source: Coastal Collection Real Estate Inc. #584802 Report a problem | ||
| 4/5/2019 | Price change | $592,000-0.8%$413/sqft |
Source: Coastal Collection Real Estate Inc. #584802 Report a problem | ||
| 3/18/2019 | Listed for sale | $597,000+70.6%$416/sqft |
Source: Coastal Collection Real Estate Inc. #584802 Report a problem | ||
| 3/18/2013 | Sold | $350,000$244/sqft |
Source: Public Record Report a problem | ||
| 1/22/2013 | Listed for sale | $350,000+27.3%$244/sqft |
Source: APA Investment Group, Inc. #A1683344 Report a problem | ||
| 9/26/2012 | Listing removed | $275,000$192/sqft |
Source: APA Investment Group, Inc. #A1683344 Report a problem | ||
| 9/1/2012 | Listed for sale | $275,000-68.7%$192/sqft |
Source: APA Investment Group, Inc. #A1683344 Report a problem | ||
| 5/19/2005 | Sold | $879,000+2219.3%$613/sqft |
Source: Public Record Report a problem | ||
| 6/12/1995 | Sold | $37,900$26/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $7,973 +4.1% | $820,808 +1.6% |
| 2024 | $7,660 +19.8% | $807,938 +39.7% |
| 2023 | $6,395 +17.1% | $578,293 +10% |
| 2022 | $5,459 +7.6% | $525,721 +10% |
| 2021 | $5,075 +1.6% | $477,928 +2.8% |
| 2020 | $4,996 | $464,952 -1.4% |
| 2019 | $4,996 -1.5% | $471,318 +5.6% |
| 2018 | $5,070 +2.3% | $446,497 +2.2% |
| 2017 | $4,956 +3.4% | $437,022 +11.2% |
| 2016 | $4,795 +6.1% | $392,919 +6.6% |
| 2015 | $4,521 | $368,458 |
Find assessor info on the county website
Monthly payment
Est. payment





