Venture Out (23.0) Homes under $500,000

Looking for your own little piece of paradise? This waterfront home may be the one. Situated along a canal, it offers beautiful water views from the 17-foot concrete dock, complete with a covered back patio ideal for grilling or relaxing. The patio also features a mini sink, mini fridge, and mini freezer for your entertaining pleasure. The spacious primary suite includes a king-size bed, custom closets with built-in drawers, and large windows overlooking the back patio. The beautifully updated bathroom features a walk-in shower with glass doors, handrail, built-in bench, skylight, humidifier, and exhaust fan. A versatile bonus room can serve as a second bedroom, office, or additional living space. The upgraded kitchen boasts granite countertops, a glass-tile backsplash, and stainless-steel appliances, including a gas range with convection oven and air fryer, center burner includes a griddle feature, a refrigerator with bottom drawer freezer, a microwave, and disposal. Additional features include a pantry with drawers, a 70-pound propane tank, an on-demand hot water heater, four ductless AC units, and a full-size stackable washer and dryer conveniently tucked into the hallway closet. Numerous hallway closets provide ample storage. All windows are double paned. The home features a gable metal hip roof, gutters, Bahama and panel shutters, and reinforced FEMA-approved piers. The oversized concrete driveway provides parking for both a car and a golf cart. Large doors offer easy access to plenty of additional storage beneath the home. Venture Out offers an abundance of amenities, including oceanfront picnic areas and tiki huts, boat ramps, a marina with fuel dock and store, heated saltwater pool, hot tub, tennis and pickleball courts, bocce courts, basketball courts, community bathhouses, laundry facilities, and a clubhouse with ongoing activities. The community is completely walled, gated, and secured with on-site security guards.

701 Spanish Main Dr Unit 455, Cudjoe

$239,000

1 Beds ⋅ 1 Baths ⋅ 620746 MLS

Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room. The property is currently occupied by a long-term tenant, offering an opportunity for a buyer seeking immediate rental income. The home offers a functional layout suitable for full-time living, seasonal enjoyment, or future investment use. Venture Out permits transient rentals with no minimum-night requirement, giving owners flexibility in how they choose to use the property. Community amenities include a large heated and chilled saltwater pool, hot tub, swimming lagoon, full-service marina with boat ramp and fuel dock, and convenient boating access to both the Gulf of Mexico and the Atlantic Ocean. Residents and guests also enjoy pickleball, tennis, bocce ball and basketball courts, a playground, two community centers, organized activities, and on-site church services. Looking for a fresh start? The property may also offer the potential to be converted into an RV lot or rebuilt to suit your vision, subject to current building regulations and community requirements. Schedule your private showing and explore the possibilities at Unit 533!

701 Spanish Main Dr Unit 533, Cudjoe

$444,999

1 Beds ⋅ 1 Baths ⋅ 620685 MLS

Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home, income-producing investment, or full-time residence. The home features numerous updates, including a new roof in 2018, air-conditioning system in 2020, and hot water heater in 2025. Additional improvements include newer impact-resistant windows, Bahama shutters, powder-coated storm panels, and updated mobile home tie-downs for added peace of mind. Boaters will appreciate the 35-foot concrete seawall with dock whips and quick access to the backcountry, offshore waters, and Atlantic Ocean. A concrete slab beneath the home provides valuable storage for fishing gear, kayaks, bicycles, and other Keys essentials. Venture Out offers an impressive array of amenities, including a large oceanfront saltwater swimming pool, community marina with fuel station, boat ramp, and boat wash-down area. Residents and guests also enjoy lighted tennis and pickleball courts, basketball and bocce courts, a recreation hall, waterfront pavilion, and regular community activities. The golf-cart-friendly neighborhood makes it easy to enjoy everything the community has to offer. Whether you are searching for a relaxing island escape, strong rental opportunity, or waterfront home in the Lower Keys, this property delivers an exceptional combination of location, boating access, amenities, and investment potential. Schedule your private showing today and experience this special Cudjoe Key property for yourself.

701 Spanish Main Dr Unit 246, Cudjoe

$487,000

2 Beds ⋅ 2 Baths ⋅ 620156 MLS

Seller is Motivated! Coastal Charm Meets Modern Comfort Welcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key. Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed kitchen. Recent updates include a brand-new refrigerator, ample cabinetry, and a modern island bar with additional seating, perfect for entertaining family and friends. Built with both comfort and durability in mind, the home features a reliable metal roof and a large ground-level storage enclosure for all your island essentials. Step outside to your private backyard retreat, complete with low-maintenance artificial turf and a cozy seating area, ideal for enjoying the Florida Keys sunshine. This property is a proven income-producing vacation rental with strong rental history and future bookings already in place. In 2025, the home generated $43,257.28 in rental revenue. As of June 2, 2026, it has already produced $18,472.78 year-to-date, with 8 future reservations estimated to generate an additional $13,092.57 in rental income that will transfer to the buyer. Conveniently located near the front gate of the community, this home offers easy access for pet owners, with a quick path for walking dogs just outside the neighborhood. You're also within walking distance of Venture Out's outstanding amenities, including a heated saltwater waterfront pool, swimming lagoon, private boat ramp, tennis courts, pickleball courts, bocce courts, basketball courts, marina store, community center, and more. Whether you're seeking a personal island retreat, a seasonal getaway, or an investment property with immediate income potential, this home offers the perfect combination of comfort, convenience, and Florida Keys charm.

701 Spanish Main Dr Unit 659, Cudjoe

$425,000

2 Beds ⋅ 1 Baths ⋅ 619998 MLS

Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile floor throughout. Enjoy the tropical landscaped backyard while grilling dinner or relaxing on your private deck. Indulged in the community's amenities, including an oceanfront heated saltwater pool and jacuzzi for ultimate relaxation. A marina with a fuel dock, convenient store and boat launch for the boater enthusiasts. Stay active and engaged with pickleball and tennis courts! And for Kids' there's a 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. Possible Seller Finance

701 Spanish Main Dr Unit 639, Cudjoe

$267,000

1 Beds ⋅ 1 Baths ⋅ 619175 MLS

$21,000+ Gross Rental Revenue so far in 2026! Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential. Currently operating as a successful vacation rental, the property has already generated over $21,000 in gross rental revenue for 2026, with approximately $17,000 in existing future reservations already secured as of June 5, 2026. Whether you're searching for a personal Florida Keys escape, a turnkey investment property, or both, this home is already producing income and ready to enjoy. Inside, you'll find a bright, coastal-inspired interior featuring an open-concept living space, Smart TV, and a pull-out sofa bed. The thoughtfully designed kitchen offers everything needed for easy vacation living, while the bedroom and full bathroom create a comfortable retreat after a day on the water. Step outside and relax in your outdoor space and enjoy the tropical breezes. A separate storage shed provides convenient space for fishing gear, bicycles, and beach essentials. Located at Mile Marker 23 on Cudjoe Key, Venture Out is a private, 24-hour gated oceanfront community known for its exceptional amenities and vibrant island atmosphere. Residents and guests enjoy access to a heated saltwater oceanfront pool and hot tub, boat ramp, fuel dock, ship store, tennis and pickleball courts, basketball and bocce courts, saltwater swimming lagoon, recreation center, market, post office, and golf cart-friendly streets throughout the community.

701 Spanish Main Dr Unit 423, Cudjoe

$485,000

1 Beds ⋅ 1 Baths ⋅ 613336 MLS

Oceanfront Paradise Awaits! Unit 182 in Venture Out Experience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community. This beautifully maintained home boasts: * Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall. * Community Boat Ramp and boat washdown station. * Spacious Florida Room: Expand your living space with a delightful air-conditioned Florida room, perfect for relaxing and soaking in the coastal breeze. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been meticulously cared for and is ready for you to move in and enjoy. * Gated Community: Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 182, Cudjoe

$350,000

2 Beds ⋅ 1 Baths ⋅ 618674 MLS

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 income-producing rental. FULLY FURNISHED. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white kitchen pops with marble countertops and a stunning blue tile backsplash, bringing those breezy ocean vibes right into your home. It's light, cheerful, and perfect for entertaining friends and family after a day on the water. And here's the best part -- even though this property sits on a dry lot, you still enjoy beautiful open water views. Venture Out is one of the most sought-after gated communities in the Lower Keys, known for its active lifestyle and incredible amenities: Heated community pool, Marina & boat ramp with direct ocean and Gulf access, Tennis & pickleball courts, Basketball courts, Private convenience store, Children's playground & pool, Recreation hall, 24-hour gated security. Bring your boat, your golf cart, and your flip-flops -- this neighborhood was made for enjoying the water. Located just 20 miles from Key West, you're close enough for dining, nightlife, and the airport -- but far enough away to enjoy peaceful island living. If you've been dreaming of a cozy, beach-inspired Keys escape with income potential and resort-style amenities... this is the one. Ready to make your move?

701 Spanish Main Dr Unit 536, Cudjoe

$320,000

2 Beds ⋅ 1 Baths ⋅ 618228 MLS

Canal-front opportunity in Venture Out! This 1 bedroom / 1 bath property offers a 17' seawall and endless potential for future use. Whether you're envisioning a personal Keys retreat or re-imagining the space as an RV lot, this property provides flexibility in a highly desirable, gated waterfront community. Enjoy all Venture Out amenities including marina access, boat ramp, pools, recreational facilities, and 24-hour security. A great chance to create your own slice of island living.

701 Spanish Main Dr Unit 566, Cudjoe

$329,000

2 Beds ⋅ 2 Baths ⋅ 614618 MLS

Transient Rental Vacation Home. Welcome to your ultimate island getaway on Cudjoe Key! Step into this charming coastal oasis nestled on a spacious corner lot in the sought-after Venture Out community. This 2 bedroom, 1.5 bath retreat is the perfect blend of comfort and style that will transport you to a world of relaxation and tranquility. This income-producing home is an active vacation rental as nightly rentals are allowed here. Turn-key vacation rental selling fully furnished. The kitchen has lots of cabinets, a tiled countertop that opens to the dining area. Tile flooring throughout, New central AC & heat installed in 2024, all appliances, stackable washer/dryer. Lots of built in storage in bedrooms and hallway. Vinyl siding and metal roof for easy maintenance. New impact resistant sliding door and new impact resistant windows installed in July 2024. Venture Out is a gated community with sixty-nine acres of tropical paradise situated on the island of Cudjoe Key, Florida, a short 23.8 miles north from the southernmost point of the U.S. in Key West Florida. A 659 Unit private residential condominium association consisting of both RV and mobile homes, both available for short term and long-term rentals. With exceptional access to both the Atlantic Ocean and the Gulf of America, this tropical island environment is perfect for all your ocean needs. Venture Out is a golf cart friendly, private gated community that boasts a plethora of amenities to elevate your time to the next level. Indulge in lots of amenities, including a Marina store with fuel onsite, bait and convenience market, boat wash down station, community boat ramp, 80-foot heated pool, Jacuzzi, large kiddie pool, salt water swimming lagoon, convenience market, post office, 2 lighted tennis courts, basketball and bocce courts. Call today to schedule your private showing! Owner is a licensed real estate agent in Florida.

701 Spanish Main Dr Unit 543, Cudjoe

$493,000

2 Beds ⋅ 2 Baths ⋅ 618828 MLS

PRICE DROPPED AGAIN below 500k! MOTIVATED SELLER! This is THE lowest 2BR/BA priced home in Venture Out on Cudjoe Key! Turn-key 2BR/2BA waterfront fully furnished home with 35' concrete dock and patio furniture included, Front door paver patio, impact slider doors and windows, gas stove, and ample storage including outdoor dock box. Enjoy direct, deep-water access to the Ocean & Gulf, perfect for boating, fishing, and breathtaking sunrises & sunsets. Located in Venture Out, a gated, golf cart-friendly community with 24-hour security, oceanfront heated pool & hot tub, ocean swimming area, marina, boat ramp, pickleball & tennis courts, kids' pool, and playground. Join in daily community activities at rec hall or pavilion. Move-in/rent-out ready, with nightly rentals allowed -- your Keys paradise awaits! Boat and Golf cart also available. Please inquire with Realtor

701 Spanish Main Dr Unit 417, Cudjoe

$399,900

2 Beds ⋅ 1 Baths ⋅ 618353 MLS

This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 2 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining on the patio. The garden patio at the entrance is an ideal spot to admire the beautiful mornings and evenings outside. Conveniently located in the popular Venture Out Park, this property offers all the amenities you could want. This includes a ships store, marina with fuel docks, boat ramp, large, heated pool with a saltwater filtration system, spa, showers, kiddie pool, tennis courts, pickleball courts, and even a post office, all within a secure, guard-gated entrance. Additionally, Venture Out allows for daily, weekly, and monthly rentals, making it a true paradise!

701 Spanish Main Dr Unit 140, Cudjoe

Venture Out (23.0) Homes under $500,000

Newest Venture Out (23.0) Homes under $500,000