Welcome to your private slice of paradise in desirable Cudjoe Key. this charming well maintained 3-bedroom, 2-bath home sits on an oversized double lot, offering space, privacy, and endless Keys lifestyle potential.With 1,144 square feet of living space, the home is thoughtfully laid out and surrounded by lush tropical surroundings. The property backs up to a private wooded area, creating a peaceful, secluded setting rarely found in the Keys.Step outside and you'll find a true backyard retreat--featuring a resort-style in-ground pool and a tiki hut perfect for entertaining, relaxing, or enjoying those warm island evenings. The expansive lot also provides plenty of parking for vehicles, boats, and all your recreational toysLocated just 25 minutes from Key West, you'll enjoy the perfect balance of tranquility and convenience.Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this property captures the essence of Keys living.
Sold for $775,000
$775,000
22939 Privateer Dr, Cudjoe Key, FL 33042
3beds
1,288sqft
Single Family Residence
Built in 1988
7,405 Square Feet Lot
$776,200 Zestimate®
$602/sqft
$4,339 Estimated rent
Home value
$776,200
$675,000 - $893,000
$4,339/mo
Zestimate® history
Owner options
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$4,669/mo
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$4,669/mo
Est. payment
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List your homeWhat's special
Thoughtfully laid outResort-style in-ground poolOversized double lot
Zillow last checked:
Listing updated:
Listed by:
Michelle Howerton 305-849-8794,
Brenda Donnelly Real Estate LLC,
William Lee Howerton 240-375-6379,
Brenda Donnelly Real Estate LLC
Bought with:
Lindsay Ryan, 3419167
EXP Realty LLC
Source: FLKMLS,MLS#: 619313
Originating MLS: Key West Association
Originating MLS: Key West AssociationFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Heating
- None
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Features
- Flooring: Tile, Carpet
- Windows: Impact Rstnce Window, Accordion
Interior area
- Total interior livable area: 1,288 sqft
Property
Parking
- Total spaces: 4
- Parking features: Off Street, Covered
Accessibility
- Accessibility features: No
Features
- Patio & porch: Patio, Screened Patio
- Exterior features: Storage, Outdoor Shower
- Has private pool: Yes
- Pool features: In Ground, Salt Water
- Fencing: Privacy
- Water view: None
- Waterfront features: None, Dockage: None
Lot
- Size: 7,405 Square Feet
- Dimensions: 75 x 100
- Features: Less Than 1/4 Acre
Details
- Additional structures: Chickee Hut, Shed(s)
- Parcel number: 00187610000000
- Zoning: IS
- Zoning description: Improved Subivision District
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Frame
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 1988
Utilities & green energy
- Sewer: Public Sewer
- Utilities for property: FKAA
Community & HOA
Community
- Subdivision: Cudjoe Ocean Shores (23.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Cudjoe Key
Financial & listing details
- Price per square foot: $602/sqft
- Tax assessed value: $711,938
- Annual tax amount: $879
- Date on market: 4/1/2026
Price history
| Date | Event | Price |
|---|---|---|
| 5/1/2026 | Sold | $775,000$602/sqft |
Source:  FLKMLS #619313 Report a problem | ||
| 4/18/2026 | Contingent | $775,000$602/sqft |
Source:  Key West AOR #619313 Report a problem | ||
| 4/1/2026 | Listed for sale | $775,000+248.3%$602/sqft |
Source: Key West AOR #619313 Report a problem | ||
| 3/5/2002 | Sold | $222,500+45.4%$173/sqft |
Source: FLKMLS #509722 Report a problem | ||
| 8/6/1999 | Sold | $153,000$119/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $880 +3.4% | $316,053 +2.9% |
| 2024 | $851 +12% | $307,146 +3% |
| 2023 | $760 +1.5% | $298,200 +3% |
| 2022 | $749 | $289,515 +3% |
| 2021 | -- | $281,083 +1.4% |
| 2020 | -- | $277,203 +2.3% |
| 2019 | $710 +0.7% | $270,971 +1.9% |
| 2018 | $705 +1.1% | $265,919 +2.1% |
| 2017 | $697 +1.2% | $260,450 |
| 2016 | $689 | $260,450 0% |
| 2015 | $689 | $260,580 |
Find assessor info on the county website
Neighborhood: 33042
Nearby homes
- $767,2003 bd2 ba1.2k sqft22929 Privateer Dr, Cudjoe Key, FL 33042Off Market
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- $747,8002 bd2 ba1k sqft22940 Privateer Dr, Cudjoe Key, FL 33042Off Market
- $712,6002 bd2 ba1.9k sqft22950 Privateer Dr, Cudjoe Key, FL 33042Off Market
Nearby schools
GreatSchools rating
- 6/10Sugarloaf SchoolGrades: PK-8Distance: 3.4 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 20.3 mi
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Estimated market value
$776,200
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$776,200
- Florida
- Monroe County
- Summerland Key
- 33042
- 22939 Privateer Dr
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