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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
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, 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!!!
More Information MLS# 619615
Contract Information
Current Price: $2,800,000
Listing Date: 2026-04-23
Listing Board: Key West Association
List Price: $2,800,000
Bank Owned: No
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
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 2
Pool: Yes
Year Built: 1985
Lot Size: X
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
Status Change Info
Status: Active
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
License Info
# of City License: 1
Transient Rntl Licns: Yes
Dockage
Dock: Wood
Building Style
Above Flood: Unknown
Stilt Column Height: Tall - 10Ft & Over
Stories: 2 Stories
Vehicle Storage
Car(s): 4+
Financial Status
Bank Owned: No
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.
