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
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