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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

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, enter ...

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.