21640 Overseas Highway, Cudjoe Key, FL 33042
$2,800,000
Property Type:
Residential
Bedrooms:
4
Baths:
3
Square Footage:
3,286
Lot Size (sq. ft.):
31,250
Status:
Active
Current Price:
$2,800,000
List Date:
4/23/2026
Last Modified:
4/28/2026
Overview
Description
...
(Read more)
SPECIAL DAILY TRANSIENT LICENSE!!!
Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find.
From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace.
Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard.
Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space.
For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!
Listing Details MLS# 619615
Location, Tax & Legal
- Street #
- 21640
- Street Name
- Overseas
- Street Suffix
- Highway
- Key/Island
- Cudjoe Key
- State/Province
- FL
- Zip Code
- 33042
- County
- Monroe
- Subdivision
- Sacarma (21.0)
- Area
- 07 - Cudjoe Key
- City
- Cudjoe
- Mile Marker
- 21
- Marathon Neighborhood
- N/A
- Side
- Ocean
- Alternate Key #
- 1226891
- Parcel #
- 00174830000000
- Zoning
- URM - Urban Res Mobile Home District
- Deed Restrictions
- Unknown
- Legal
- Sacarma Pb2-48 Cudjoe Key Lot 18 And Adj Btm Or7-445 Or218-356(Ii Deed 22794) Or392-164/165 Or839-2255 Or840-498C Or874-
- Taxes
- 17431.92
- Tax Year
- 2025
- Pub Sewer HkUp
- Yes
Contract Information
- Listing Board
- Key West Association
- Bank Owned
- No
General Property Description
- Realtor.COM Type
- Residential - Single Family
- Style
- Single Family
- Waterfront
- Yes
- Control Depth
- 2
- Pool
- Yes
- Year Built
- 1985
- Lot SqFt
- 31250
- Lot Sqft Source
- Property Data Card
- Acres
- 1.17
- Living Apx SqFt
- 3286
- SqFt Source
- Appraisal
- Total Bedrooms
- 4
- Full Baths
- 3
- Total Baths
- 3
- Rentals Allowed
- Yes
Association Info
- Mandatory Home Owners Asc
- No
- 1st Right of Refusal
- No
- Association Fee $
- 0
License Info
- # of City License
- Yes
- Transient Rntl Licns
- Yes
More Information
Dockage
- Dock
- Wood
Building Style
- Above Flood
- Unknown
- Stilt Column Height
- Tall - 10Ft & Over
- Stories
- 2 Stories
Vehicle Storage
- Car(s)
- 4+
- Covered Parking
- Yes
- Garage
- Yes
- Guest Parking
- Yes
- RV Parking Covered
- Yes
- Airplane Hanger
- Yes
- Assigned Parking
- Yes
Financial Status
- Bank Owned
- No
Remarks & Misc
- Remarks – Consumer
- SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!
Fee Includes
- None
- Yes
Tax Exemptions
- None
- Yes
Appliances
- Dishwasher
- Yes
- Disposal
- Yes
- Dryer
- Yes
- Freezer
- Yes
- Oven
- Yes
- Range
- Yes
- Refrigerator
- Yes
- Washer
- Yes
Pets
- Pets Allowed
- Yes
Cooling
- Attic Fan
- Yes
- Ceiling Fans(s)
- Yes
- Central Air
- Yes
- Heat Pump
- Yes
Waterfront
- Oceanfront
- Yes
- Open Water
- Yes
Waterview
- Ocean View
- Yes
- Open Water View
- Yes
Floor
- Combo
- Yes
Interior Features
- Built-in Cabinets
- Yes
- Cathedral Ceilings
- Yes
- Dade County Pine
- Yes
- Fireplace(s)
- Yes
- Granite Counter Top
- Yes
- Smoke Alarms
- Yes
- Walk-in Closet(s)
- Yes
- Whirlpool Bath Tub
- Yes
- Other
- Yes
Property Condition
- Updated/Remodeled
- Yes
Specialty Rooms
- Other
- Yes
Windows/Doors
- Aluminum Windows
- Yes
- Sliding Glass Doors
- Yes
Construction
- Hardi Board Siding
- Yes
Land Size
- 1 Less Than 2 Acres
- Yes
Furnished
- Furnished
- Yes
Utilities
- FKAA
- Yes
- Municipal Sewer
- Yes
Porch/Balcony
- Deck
- Yes
- Patio
- Yes
- Screened P/B
- Yes
- Screened Patio
- Yes
Title
- Negotiable
- Yes
Exterior Features
- Chickee Hut
- Yes
- Hot Tub
- Yes
- Privacy Wall/Fence
- Yes
- Sandy Beach
- Yes
- Storage
- Yes
Pool Info
- In Ground
- Yes
Roof
- Metal Roof
- Yes
Property Features
Fee Includes:
None
Tax Exemptions:
None
Waterfront:
Oceanfront; Open Water
Waterview:
Ocean View; Open Water View
Property Condition:
Updated/Remodeled
Vehicle Storage:
Garage; Airplane Hanger; Assigned Parking; Covered Parking; Guest Parking; RV Parking Covered
Furnished:
Furnished
Cooling:
Attic Fan; Ceiling Fans(s); Central Air; Heat Pump
Utilities:
FKAA; Municipal Sewer
Interior Features:
Built-in Cabinets; Cathedral Ceilings; Dade County Pine; Fireplace(s); Granite Counter Top; Smoke Alarms; Walk-in Closet(s); Whirlpool Bath Tub; Other
Specialty Rooms:
Other
Appliances:
Dishwasher; Disposal; Dryer; Freezer; Oven; Range; Refrigerator; Washer
Exterior Features:
Chickee Hut; Hot Tub; Privacy Wall/Fence; Sandy Beach; Storage
Pool Info:
In Ground
Construction:
Hardi Board Siding
Floor:
Combo
Roof:
Metal Roof
Pets:
Pets Allowed
Land Size:
1 Less Than 2 Acres
Title:
Negotiable
Listing Office:
Key West Luxury Real Estate Inc (KW)
Last Updated: April - 28 - 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.
