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  • 21640 Overseas Highway, Cudjoe Key, FL 33042 (MLS# 619615)

21640 Overseas Highway, Cudjoe Key, FL 33042

New Listing
$2,800,000
Property Type: Residential Bedrooms: 4 Baths: 4 Square Footage: 3,286 Lot Size (sq. ft.): 31,250 Status: Active
Current Price: $2,800,000 List Date: 4/23/2026 Last Modified: 4/23/2026

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

Listing Board: Key West Association Bank Owned: No Current Price: $2,800,000 Listing Date: 2026-04-23 List Price: $2,800,000

Location, Tax & Legal

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 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 Waterfront: Yes Control Depth: 2 Lot Size: X Lot SqFt: 31250 Pool: Yes Lot Sqft Source: Property Data Card Acres: 1.17 SqFt Source: Appraisal Rentals Allowed: Yes Style: Single Family Year Built: 1985 Living Apx SqFt: 3286 Total Bedrooms: 4 Full Baths: 4 Total Baths: 4

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!!!

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

License Info

# of City License: 1 Transient Rntl Licns: Yes

Fee Includes

None: 1

Dockage

Dock: Wood

Tax Exemptions

None: 1

Appliances

Dishwasher: 1 Disposal: 1 Dryer: 1 Freezer: 1 Oven: 1 Range: 1 Refrigerator: 1 Washer: 1

Pets

Pets Allowed: 1

Cooling

Attic Fan: 1 Ceiling Fans(s): 1 Central Air: 1 Heat Pump: 1

Waterfront

Oceanfront: 1 Open Water: 1

Waterview

Ocean View: 1 Open Water View: 1

Floor

Combo: 1

Interior Features

Built-in Cabinets: 1 Cathedral Ceilings: 1 Dade County Pine: 1 Fireplace(s): 1 Granite Counter Top: 1 Smoke Alarms: 1 Walk-in Closet(s): 1 Whirlpool Bath Tub: 1 Other: 1

Property Condition

Updated/Remodeled: 1

Specialty Rooms

Other: 1

Building Style

Above Flood: Unknown Stilt Column Height: Tall - 10Ft & Over Stories: 2 Stories

Windows/Doors

Aluminum Windows: 1 Sliding Glass Doors: 1

Vehicle Storage

Car(s): 4+ Covered Parking: 1 Garage: 1 Guest Parking: 1 RV Parking Covered: 1 Airplane Hanger: 1 Assigned Parking: 1

Construction

Hardi Board Siding: 1

Land Size

1 Less Than 2 Acres: 1

Furnished

Furnished: 1

Utilities

FKAA: 1 Municipal Sewer: 1

Porch/Balcony

Deck: 1 Patio: 1 Screened P/B: 1 Screened Patio: 1

Title

Negotiable: 1

Exterior Features

Chickee Hut: 1 Hot Tub: 1 Privacy Wall/Fence: 1 Sandy Beach: 1 Storage: 1

Pool Info

In Ground: 1

Roof

Metal Roof: 1

Financial Status

Bank Owned: No

Status Change Info

Status: Active

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 - 23 - 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.

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