Cudjoe Key Florida homes for sale starting at Fifty Thousand Dollars

$998,000 - Cudjoe Key, FL

246 Colson Drive Cudjoe Key, FL - SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet neighborhood - But close enough to Key West for all the Entertainment & Fun. Truly a Fisherman's Dream.

$989,999 - Cudjoe Key, FL

22961 John Avery Lane Cudjoe Key, FL - Boater's Paradise in Cudjoe Key under 1 million! Priced to Sell! Bring all offers!Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle.The lower level offers a private in-law suite just steps from the water. Built only three years ago, this self-contained apartment features a full kitchen, its own A/C system, premium waterproof PVC flooring, and marine-grade insulation -- ideal for guests, rental income, or extended family.Upstairs, the main residence features a bright, open-concept living space with large impact-resistant windows and doors installed by the previous owners, offering both natural light and storm protection. The home is energy-efficient and move-in ready.Located in a quiet and highly desirable neighborhood in Cudjoe Key, this fully furnished gem is a rare opportunity to own a true Keys boater's dream home. Whether you're an avid fisherman or just looking for the ultimate waterfront lifestyle, this property is a must-see!

$985,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Panoramic Ocean Views With Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to come and relax. Perfect for the fishing enthusiasts, enjoy quick boating access to the Atlantic Ocean and Gulf of America. Boat, swim, snorkel or dive in the beautiful Florida Keys right from your 35-foot seawall, plus the added bonus of all that Venture Out gated community has to offer. Venture Out has 4 miles of paved secured streets to walk or bike. Amenities include oceanfront heated saltwater pool, jacuzzi, marina with fuel dock, boat launch, convenient store, tennis, pickleball, bocce, basketball, playground, fun activities and more! Close to restaurants, shopping, parks and local events, this property has something for everyone!

$925,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Nightly Licensed Transient Rental!!!This amazing, two bedroom / one bathroom, open water front, nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rent license. The floor plan makes the open water views as its main focus. Cook the catch of the day over looking the waters that you just caught that prized fish in. Sit back and watch your friends and family enjoy those waters with your favorite beverage in hand, and enjoy those fruits of your hard labor. This home is built with easy maintenance in mind, don't worry just enjoy. This home does come with approved engineered plans to build a second bathroom if needed.There is covered parking and a covered storage for all your needs. Just sit back and enjoy this amazing location. This one is location, location, location!Enjoy tropical breezes and island living in this amenity-rich resort-style neighborhood. Venture Out features 24-hour gated security, an oceanfront heated pool, hot tub, fuel station, marina, boat ramp, tennis and pickleball courts, a waterfront picnic pavilion, and much more.Located just 19 miles from Key West and minutes from world-class fishing, diving, and boating, Home 49 offers everything the Keys lifestyle promises--sun, sea, and serenity.Call today for a showing!

$885,000 - Cudjoe Key, FL

22739 Buccaneer Lane Cudjoe Key, FL - If you're looking for the ultimate ''Island Life'' this charming canal-front home in sought-after Cutthroat Harbor Estates is exactly what you need. This 2 Bedroom 2 Bath home is located on the ocean side with excellent boating access to the Atlantic & Gulf. This home includes a #10,000 pound boat lift, full concrete seawall, large storage area below, and a fully fenced yard, making it a perfect fit for the fishing and diving enthusiasts. Nestled in a tranquil quaint little neighborhood, this inviting Cudjoe Key home offers quiet streets lined with swaying palms and lush tropical foliage, creating the perfect setting for leisurely strolls or evening bike rides taking in the sunset. The interior is full of Keys character, and has been very well maintained. The living area is bright and spacious and well thought out with large bedrooms and a nice sized dining area right off of the kitchen. The huge covered screened back deck overlooking the canal is the perfect spot to enjoy dinner and cocktails al fresco while talking about your incredible day on the water. The Florida Keys offers world class fishing and diving, as well as the most beautiful pristine backcountry islands with reef patches, sand flats, and channels to explore. This prime location in Cudjoe Key is just a short drive to Key West, where you'll discover fabulous restaurants, world famous bars with nightly entertainment, and the rich culture of Old Town with a lively art scene including several intimate theaters. Or choose to immerse yourself in our unique ecosystem on the water or on the Florida Keys Overseas Heritage Trail, a scenic route spanning over 90 miles with paved bike paths connecting Key Largo to Key West where you will encounter a diverse array of aquatic birds in their natural habitat. This location has something for everyone.

$850,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Beautiful canal front home with open water views from your spacious open-air porch. Located in a gated community with TRANSIENT RENTALS and tons of amenities. 35' custom-tiled concrete seawall and covered carport w/storage room. Beautiful kitchen with double oven, stainless appliances, Corian countertops and lots of cabinets for all your storage needs. Open floor plan w/dedicated dining area, large living room, tile floors, recessed lighting and crown molding throughout. Spacious master-suite with both guest and master bath offering tiled shower surround, glass doors with lots of storage. Nicely appointed guest bedroom and bathroom. House comes furnished. Just bring your swimsuit, your boat and get ready to enjoy the beautiful water and activities in the Florida Keys.

$795,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - This canal-front, slice of paradise is an excellent income-generating opportunity in the gated community of Venture Out. As a successful, active vacation rental where nightly rentals are allowed, it's tastefully furnished, turnkey and ready for you or your guests to enjoy. With all the amenities this 69-acre gated community offers, you might just decide to make it your primary home in the Lower Keys! The 35 ft. concrete seawall is the perfect spot for keeping your boat when you're not on the water in the Atlantic and back-country. You'll appreciate the convenience of the community boat ramp, as well as the on-site fuel and community store. Built in 2010, the 2-bedroom, 864 sq. ft. stilt home features a metal roof, impact-resistant windows, a covered porch with water views, a welcoming great room and well-equipped kitchen, an extra-large bath with dual vanities, and a roomy walk-in closet in the primary bedroom. The ground level provides a storage room for tools and bikes, an inviting canal-side sitting area that's under cover, and covered parking for one car. For those who enjoy staying active, golf cart-friendly Venture Out offers an 81,500-gallon heated saltwater pool, a kiddy pool, and a spa/jacuzzi, as well as lighted courts for tennis, pickleball, bocce, and basketball. You won't want to miss the variety of activities happening in the recreation hall and community pavilion!

$700,000 - Cudjoe Key, FL

22882 Buccaneer Lane Cudjoe Key, FL - Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the ocean.Inside, the open-concept living area invites relaxation, with natural light pouring in and serene water views. Enjoy seamless indoor-outdoor living with two screened patios--ideal for entertaining, morning coffee, or evening sunsets. A 2-car garage provides ample storage for vehicles and gear, enhancing both convenience and security.Move-in ready and primed for your personal touch, this home is a rare gem in a prime location. Don't miss your chance to own a slice of waterfront paradise!

$699,000 - Cudjoe Key, FL

21161 Old State Rd 4A Cudjoe Key, FL - Island life awaits! Beautiful, elevated home boasts 2 spacious bedrooms and 2 recently renovated baths. Fenced yard with ample parking. Just off famous US1 this property is sited on a spacious lot with plenty of versatility! Zoning is Suburban Commercial (SC) which may allow for a Special Vacation Rental Permit. Perfect property for an owner occupier or investor. Wraparound porch offers sunrise and sunset views with a deck off kitchen/primary suite and another deck off living room along with two sets of stairs with access to yard and parking. Bonus non-confirming space is ideal for a home office or commercial use. Property offers ample off-street parking for your RV, autos, and boat. The large lot is fenced and private with room for a pool or perfect as is with the tropical landscape and low maintenance ground covering. Owner occupied and well maintained, this property is move in ready. Hurricane shutters, metal roof, secluded private lot, & custom outdoor shower make this a perfect Keys oasis. Building up or adding a rooftop deck would give you amazing water views. Property has a tankless water heater and sheds for extra storage. Great location in the Florida Keys with nearby community boat ramp, dining and beaches. Bahia Honda State Park just 17 miles and Key West 19 miles.

$699,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Beautiful Transient Rental Home in Gated Florida Keys Community with Boat Dock and Davits! Welcome to your dream home in the Florida Keys! This updated 2-bedroom, 2-bath home offers an open-concept living area with a fully stocked kitchen, living room, guest bedroom & bathroom and the primary bedroom offers an en suite bathroom all beautifully furnished. The kitchen comes equipped with a full line of stainless steel appliances, upscale hardwood cabinets and butcher block countertops and is perfect for preparing your days catch. Step outside to your furnished private covered deck that leads to your boat dock equipped with Davits, ready to accommodate your boat up to 10,000 lbs. The home features all new kitvhen appliances, new air conditioner, newer metal roof and is situated within a sought-after gated community with top-notch amenities. Enjoy access to Pickleball, tennis, and basketball courts, as well as a Marina with a fuel dock and a convenient store and boat launch. The community rec hall is equipped with ping-pong, pool table, darts and library for endless entertainment. Ideal for investment or personal use, the property boasts a transient rental license, allowing for 1 day short-term rentals. Parking for one vehicle is included and no age restrictions. This is Keys living at its finest--whether you're looking for a permanent residence, vacation home, or rental income opportunity, this property has it all!! Motivated Seller. Possible Seller Financing!

Cudjoe Key, Florida listings for sale

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