Contact Pip

How would you like to connect?

Home / Listings / A12116383

21650 Overseas Hwy

Lower Keys, FL 33042

MLS# A12116383

Want to See All 36 Photos?

Register for free to view all property photos and get access to exclusive listings!

Register for Free Access

You've viewed 10 of 36 photos

Property Details

Bedrooms

2

Bathrooms

3

Square Feet

1,156

Year Built

2007

Property Type

Single Family Residence

Status

Active

Description

Experience the best of the Lower Keys with this rare opportunity to own a property that blends personal enjoyment with exceptional income potential. Whether you're searching for a private waterfront getaway, vacation retreat, or proven income-producing investment, this property delivers on all fronts. Successfully operated as a short-term rental since 2018, this home has consistently generated over $100,000 annually in rental income, offering a turnkey investment opportunity while enjoying the Florida Keys lifestyle. One of the property's most valuable features is its fully transferable transient rental license, valued at approximately $400,000. Unlike many Lower Keys properties with strict rental limitations, this license allows hotel-style rentals with no minimum night restrictions — a rare and highly desirable advantage. Each home includes a private dock slip, perfect for boats, jet skis, kayaks, and other water toys. This exclusive community of just 11 homes offers exceptional privacy, a shared heated pool, and a low, owner-operated HOA. Offered fully furnished and turnkey, the property includes established rental history and everything needed to continue operating immediately. Enjoy boating, fishing, diving, and the ultimate Florida Keys lifestyle from this ideally located Cudjoe Key property.

Features

Second Floor Entry
Family Room
Utility Room/Laundry

Interested in this property?

Similar Homes You May Like

27403 Antigua Ln
$990,000

27403 Antigua Ln

Lower Keys, FL 33042

Waterfront value-add opportunity in the Florida Keys with direct ocean access and no fixed bridges - perfect for serious boaters with vessels up to 60 feet. Situated on an oversize 18,000 SF lot, this property offers rare space, flexibility and future potential not commonly…

Read more

This listing is courtesy of Capital Intl Realty LLC.

3 Bed 3 Bath 1,954 sqft
View Details
Address unavailable
$985,000

Address unavailable

Lower Keys, FL 33042

ROGO EXEMPT CANALFRONT WITH GREAT SUNSETS AND OPEN WATER VIEWS READY FOR YOU TO BRING YOUR BOAT WITH STEP DOWN DOCK. DOCK NEEDS SOME TLC. ACTIVE WATER METER ON SITE, SEWER STUBBED IN AND READY FOR CONNECTION AS A PRIOR HOME WAS DEMOLISHED. BUYER TO VERIFY ALL INFORMATION. POWER…

Read more

This listing is courtesy of Xcellence.

— Bed — Bath — sqft
View Details
701 Spanish Main Dr # 536
$350,000

701 Spanish Main Dr # 536

Lower Keys, FL 33042

Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready — whether you're looking for a full-time residence, vacation getaway, or…

Read more

This listing is courtesy of EXP Realty LLC.

2 Bed 1 Bath 726 sqft
View Details
17287 Cayman Dr # 17287
$7,800

17287 Cayman Dr # 17287

Sugarloaf, FL 33042

Beautiful furnished waterfront home in Summerland Key offering 3 bedrooms and 2 bathrooms, available for seasonal or extended stays with a 28-day minimum. Located on a private canal with concrete dock and convenient access to surrounding waterways and open water. The home…

Read more

This listing is courtesy of Realty One Group Evolution.

3 Bed 2 Bath 1,488 sqft
View Details

More Homes in 33042

View all homes in 33042
00222210-000000 Florida Ave
$225,000

00222210-000000 Florida Ave

Torch Key, FL 33042

Discover a vacant land opportunity in Windward Beach Estates on Little Torch Key in the Lower Florida Keys. Offered at $225,000, this approximately 6,000-square-foot parcel measures approximately 60 by 100 feet and comprises Block 5, Lot 6. The supplied aerial depicts the lot…

Read more

This listing is courtesy of Capote Global Realty LLC.

— Bed — Bath — sqft
View Details
133 Indies Rd
$4,550

133 Indies Rd

Lower Keys, FL 33042

Look no further! This beautiful move in ready home on a huge double lot, with ocean access & no fixed bridges in Breezeswept Beach Estates. Pets allowed! Close to Military Bases like Naval Air Station Key West & USCG Sector Key West. This home is so cozy that you will never want…

Read more

This listing is courtesy of Global Luxury Realty LLC.

3 Bed 2 Bath 1,360 sqft
View Details
22925 JOHN AVERY Lane
$1,900,000

22925 JOHN AVERY Lane

, FL 33042

Spend the day on the water and catch the sunset from your wraparound balcony. This custom-built home offers 60 feet of canal frontage, a private dock, a launch ramp for kayaks and small boats, and access to the Atlantic and Gulf with no fixed bridges. Inside, 2,638 square feet…

Read more

This listing is courtesy of Your Esquire Realty.

4 Bed 4 Bath 2,638 sqft
View Details
27385 Saint Lucie Lane
$2,199,000

27385 Saint Lucie Lane

, FL 33042

Fully Furnished Tropical Keys Oasis - Waterfront Luxury Living Just unpack and start living the island life in this completely renovated, one-of-a-kind tropical oasis that rivals any luxury 5-star resort. Relax in the sparkling pool surrounded by lush, mature landscaping,…

Read more

This listing is courtesy of William Raveis Real Estate.

4 Bed 2 Bath 1,994 sqft
View Details
1041 E Buttonwood Dr
$9,970,000

1041 E Buttonwood Dr

Sugarloaf, FL 33042

THE AZURE ESTATE | Where Luxury Meets Wellness. Discover a stunning, brand-new solid concrete architectural masterpiece on the open waters of Sugarloaf Key, where striking design, coastal resilience, and wellness-inspired luxury create an extraordinary Florida Keys lifestyle.…

Read more

This listing is courtesy of Compass Florida, LLC.

6 Bed 8 Bath 4,894 sqft
View Details
17387 Dolphin Street E
$3,750,000

17387 Dolphin Street E

, FL 33042

Welcome to Morning Glory - The Dolphin House, a rare direct oceanfront retreat in the Florida Keys. Situated on an oversized oceanfront lot, this 4BR/3.5BA home offers 2,478 SqFt of coastal elegance, breathtaking Atlantic views, and the peaceful lifestyle buyers dream about.…

Read more

This listing is courtesy of Coldwell Banker Schmitt Real E.

4 Bed 3 Bath 2,409 sqft
View Details

Own a home nearby? See what it may be worth

Get a free, no-obligation valuation from a local Miami real estate expert.

Get Your Home Valuation

Get new listings in 33042

Register for updates on homes that match the area you are exploring.

Alert Me

Listing data updated