Cudjoe Key Florida homes for sale starting at Fifty Thousand Dollars

$679,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Are you dreaming of owning a piece of paradise in the Fabulous Florida Keys? Look no further than this gorgeous 2 bedroom, 2 bath waterfront home in the highly desired Venture Out Park in Cudjoe Key. This clean and updated home features a 35' concrete dock with whips, heavy duty aluminum posts, and easy access to enjoy both the gulf and ocean for world-class fishing and diving adventures. Inside, you'll find all new appliances, including an extra mini refrigerator, new A/C, a gas stove with air fryer and convection capability complete w/a 100-gallon propane tank. The home also has accordion shutters for all windows, sunshades on the patio, and stunning open water views. On the dock you can take advantage of the fish cleaning station, storage under the house with lots of space and a bait freezer. Amenities at Venture Out include a marina store, boat ramp, fuel docks, heated pool with saltwater filtration, spa, pickleball and tennis courts, and even a post office. This property is also a great investment opportunity, with options for nightly, weekly, or monthly rentals. Furniture included. Don't miss your chance to own your slice of paradise.

$659,999 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Welcome to a stunning brand-new construction in the sought-after Venture Out community on Cudjoe Key. This turnkey investment property is designed for comfort and style offering high-quality upgrades and modern features. Built on 9-foot concrete columns with hardy board siding, metal roof and concrete stairs/decking, all meeting 2023 installation standards. Features open concept floor plan with fine finishes, 9ft ceilings, crown molding and beautiful laminate flooring, stainless steel appliances, ample storage and open concept living area. Spacious bedrooms with the primary bedroom features an en-suite master bathroom, while the guest bedroom offers its own private balcony. Enjoy the many community amenities, including an oceanfront heated saltwater pool and jacuzzi for ultimate relaxation. Large marina with fuel dock, convenience store and boat launch for the boating enthusiast. Stay active and engaged with pickleball and tennis courts! And for Kids there's a kiddie pool and playground where the little ones can have fun. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Motivated seller. Possible Seller Financing. Sister property also for sale.

$649,999 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Welcome to a stunning brand-new construction in the sought-after Venture Out community on Cudjoe Key. This turnkey investment property is designed for comfort and style offering high-quality upgrades and modern features. Built on 9-foot concrete columns with hardy board siding, metal roof and concrete stairs/decking, all meeting 2023 installation standards. Features open concept floor plan with fine finishes, 9ft ceilings, crown molding and beautiful laminate flooring, stainless steel appliances, ample storage and open concept living area. Spacious bedrooms with the primary bedroom features an en-suite master bathroom, while the guest bedroom offers its own private balcony. Enjoy the many community amenities, including an oceanfront heated saltwater pool and jacuzzi for ultimate relaxation. Large marina with fuel dock, convenience store and boat launch for the boating enthusiast. Stay active and engaged with pickleball and tennis courts! And for Kids there's a kiddie pool and playground where the little ones can have fun. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Motivated Seller. Possible Seller Finance. Sister property also available.

$645,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Affordable piece of paradise! Move in ready, open concept, bright and airy, and freshly painted interior! This 2 bedroom 2 bath home is so spacious you'll be amazed. It has a very large kitchen and living area that looks out over the canal, with sliding glass doors out on to the newly painted deck. Minisplits in each room that cool, heat and dehumidify! Plus, a 5 stage reverse osmosis water purifier! There is 44 ft of concrete dockage, very generous for this community, and lots of storage underneath the house for all your boating and fishing gear. A large pool, hot tub, and tons of community activities are just a few of the amenities Venture Out has to offer its residents.

$599,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Beautifully renovated 2 bedroom, 2 bathroom canal front home in a gated community with TRANSIENT RENTALS PERMITTED! Well appointed eat-in kitchen and open concept living with family room that opens onto your spacious outdoor porch overlooking the clear boating canal. 35-foot concrete seawall with quick boating access to the Gulf of Mexico and Atlantic Ocean. Home comes fully furnished and has NEW: A/C unit, hot water heater, LVT flooring, sliding glass door, refrigerator, microwave, dishwasher, countertops, bathroom faucets, toilet and washer/dryer... this property is MOVE-IN-READY and like new! Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Venture Out community amenities: oceanfront heated saltwater pool and jacuzzi, a marina with fuel dock, convenient store and boat launch pickleball, basketball and tennis courts.

$569,000 - Cudjoe Key, FL

134 Tortuga Lane Cudjoe Key, FL - Waterfront Fixer-Upper with Endless Potential in Cudjoe Key!📍 134 Tortuga Ln, Cudjoe Key, FL 33042Embrace the opportunity to transform this waterfront gem into your Florida Keys dream retreat! Nestled in the desirable community behind the famous Square Grouper Restaurant this property offers direct boating access to the Atlantic Ocean--no bridges, no hassle, just open water in mere minutes.Situated on a spacious canal-front lot, this home is a blank canvas for creative visionaries or savvy investors. The structure offers a solid footprint with stilted concrete columns in excellent condition, ample square footage and room to reimagine the layout to suit your style. The potential here is undeniable. Renovate or start from scratch, either way you cannot lose with this gorgeous Old Keys lot and location!Property Highlights:🛏️ 3 Bedrooms | 🛁 2 Bathrooms 🌊 Deepwater canal with 3 ft draft in Bay and channel for quick ocean water access🚤 60' natural rock seawall 🛠️ Home needs renovation - ideal for buyer wanting to create their own space with all new touches and finishes🌴 Spacious yard with tropical and mature gorgeous palms and vegetation, and room for a pool🏝️ Quiet neighborhood with beautiful homes and a private, relaxed atmosphereWhether you're seeking a peaceful island getaway or a project with serious upside, 134 Tortuga Ln offers the location, waterfront access, and vision-ready structure to make your Florida Keys real estate dreams come true.📞 Call today to schedule a private tour and explore the possibilities!

$559,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Welcome to your tropical retreat! This 2-bed, 1.5-bath canal-front mobile home in Cudjoe Key offers open ocean access and the perfect blend of comfort and affordability. Located in the desirable Venture Out community, this property is also a proven income-producing vacation rental, making it a fantastic investment opportunity.Venture Out is a residential condominium community with 24-hour gated security and no age restrictions. The home includes parking for one vehicle, and the community allows transient (1-day) rentals, as well as two pets. Residents enjoy a heated saltwater oceanfront pool, jacuzzi, marina with a fuel dock, convenience store, boat launch, and recreational courts for pickleball, basketball, and tennis.This property is only 19 miles from Key West, offering proximity to shopping, dining, and entertainment while providing a serene getaway. Whether you're seeking a vacation home, a rental income property, or your own slice of paradise, this one has it all.

$549,900 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Transient 1 Day Rentals Allowed! Welcome to your tropical paradise! This charming 2 bedroom, 2 bathroom home in Cudjoe Key offers the perfect blend of comfort and island living. Enjoy the open-concept living and dining area, perfect for entertaining guests and take in all of the sunrise and sunset views from your porch! Take advantage of all the amenities that come with being located in the well known Venture Out community. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Venture Out community amenities include an oceanfront heated saltwater pool and jacuzzi, a marina with fuel dock, a convenient store and boat launch, pickle-ball, basketball, tennis courts and so much more!

$549,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - $24K+ Booked Income for 2025 | 1-Day Rental License | Waterfront & Dockage IncludedPriced at just $559,000, this canal-front 2/1 in Venture Out offers both investment performance and laid-back island living.Inside, you'll find an open-concept mobile home on a concrete slab, complete with a Florida Room, remodeled interiors, and a modern kitchen. The 35' dock is ready for your boat--with power, swim ladder, and fish-cleaning station.Fully licensed for nightly rentals, this home already has over 120 nights booked for 2025, averaging $244/night. Use it yourself and offset expenses or fully leverage it as a cash-flowing STR.Venture Out offers a 24/7 gated marina community with a heated pool, hot tub, tennis, pickleball, convenience store, and more--all just 23 miles from Key West.Your income-generating island escape is here. Showings available between bookings--ask for full rental history & disclosures.

$499,000 - Cudjoe Key, FL

701 Spanish Main Drive Cudjoe Key, FL - Transient Rental License. Beautiful updated 2bed/2bath, fully furnished, canal front home with look-down canal views! Interior is light and bright with the main living area surrounded by windows and a sliding glass door to bring the outdoors in. New air conditioner. Featuring a 35' concrete seawall equipped with dock whips, cleats, and storage box. Property is situated on a wide Y-shaped canal with direct access to Kemp Channel for quick access to the Gulf and Atlantic. Venture Out is a 24 hour gated community with tons of amenities including heated pool, spa, ship store, boat launch, fuel dock, picklball, tennis, bocce ball, basketball, picnic grounds, kids play area, pavilion and much more. If this is not enough Key West is just 19 miles away. Seller Financing Available!

Cudjoe Key, Florida listings for sale

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