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$1,799,000
3 Beds ⋅ 2 Baths ⋅ 621138 MLS
OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living space under air with a spacious open floor plan. An aluminum powder coated spiral stair case will lead you to an UPPER DECK where you can capture views of the sunrise and sunset along with panoramic views of Cudjoe Bay, the Atlantic Ocean and surrounding Keys. The kitchen features an Island with quartz countertops and custom cabinetry. Black stainless steel appliances. Tray ceilings and special features set this home apart. The front entrance and rear exit entry feature a red mahogany stained cypress ceiling matched perfectly to blend with the brass door handles. No details are spared with the elegance of the home's interior finishes. Ceramic tile cut on the diagonal throughout the interior and exterior porch and lanai. This home is being sold turn key with brand new furnishings as seen in the listing photos. Excellent boating access to both Cudjoe Bay and the Atlantic Ocean with 130' of canal frontage. Take over active permit for a 10 x 30 ft dock with all fees including mitigation fees already paid in full. Plenty of room for an in-ground 12 x 30 ft pool. Also possible to build on the adjoining lot with ROGO approval. Very low insurances, less than $4000 per year for Homeowners/Wind. Schedule your private showing and discover coastal living at it's finest in the Florida Keys!

22970 Gasparilla Ln, Cudjoe
$982,600
2 Beds ⋅ 2 Baths ⋅ 621115 MLS
Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access. Critical structural and exterior updates provide unmatched peace of mind and substantial insurance benefits, including a brand-new roof, newly installed heavy-duty tie-down straps, and freshly refurbished, protected under-house support beams. Go inside to a bright, turnkey coastal interior where every detail has been thoughtfully updated, complete with a smart Nest thermostat for effortless climate control and energy efficiency. The main living space is framed by expansive windows that showcase panoramic water views. The heart of the home is a fully upgraded kitchen outfitted w/new appliances, and an oversized central island featuring generous built-in storage and a breakfast bar. The spacious primary suite serves as a luxurious private haven, highlighted by an upgraded ensuite bathroom complete with a double vanity and abundant storage. Outside, the covered deck offers the ultimate vantage point to relax in the ocean breeze and take in breathtaking Florida Keys sunrises over the water. Offered fully furnished and tastefully appointed, this home is 100% move-in ready to enjoy as a primary residence, private tropical getaway, or income-producing investment as a nightly rental. Venture Out is one of the rare communities in the Lower Keys that permits lucrative nightly rentals. Enjoy an incredible lineup of resort-style amenities, featuring a massive oceanfront saltwater swimming pool, an on-site marina store with a fuel dock, boat ramps, lighted tennis and pickleball courts, basketball, bocce, a vibrant recreation hall, and 24/7 gated security.

701 Spanish Main Dr Unit 198, Cudjoe
$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

94 Sacarma Dr, Cudjoe
$549,000
2 Beds ⋅ 2 Baths ⋅ 620346 MLS
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 424 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * 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 very well cared for and updated 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! * Excellent rental income potential!!

701 Spanish Main Dr Unit 424, Cudjoe
$2,699,999
4 Beds ⋅ 3 Baths ⋅ 620277 MLS
Welcome to one of Cudjoe Gardens' most desirable waterfront addresses Built in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and remarkably affordable insurance costs. One of the property's most impressive features is its combined flood, wind, and homeowners insurance, totaling less than $5,500 per year--an extraordinary value for a waterfront home of this caliber in the Florida Keys. Designed with boaters in mind, the property offers approximately 100 feet of concrete dockage along a wide flow-through canal with deep-water access and quick routes to both the Gulf of Mexico and Atlantic Ocean. Two boat lifts, including a 10,000-pound and 14,000-pound lift, provide ample capacity for multiple vessels, making it easy to keep your boats protected and ready for your next fishing, diving, or boating adventure.The backyard is a private tropical retreat centered around a stunning 50-foot resort-style swimming pool heated/chilled Whether you're swimming laps, entertaining guests, or simply relaxing in the Florida sunshine, this outdoor space was designed to impress. A custom tiki bar, outdoor kitchen, waterfront pergola, and expansive entertaining decks create the perfect setting for hosting family and friends while enjoying beautiful waterfront views. Inside, the open-concept floor plan is filled with natural light and designed to capture water views throughout the home. High ceilings, spacious living areas, and modern coastal finishes create an atmosphere that is both elegant and comfortable. The seamless transition between indoor and outdoor living makes this home ideal for embracing the laid-back Florida Keys lifestyle.Located within the sought-after Cudjoe Gardens community, and nearby marina

20833 W 4th Ave, Cudjoe
$5,995,000
13 Beds ⋅ 7 Baths ⋅ 620213 MLS
Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe
$1,270,000
3 Beds ⋅ 2 Baths ⋅ 620186 MLS
Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and low-maintenance ownership, this 3-bedroom, 2-bath home features impact windows and doors, HardiePlank siding, Trex decking, aluminum railings, and a 180-mph wind rating. Inside, you'll find a bright, coastal-inspired interior with 9-foot ceilings, luxury vinyl plank flooring, an open-concept living area, spacious eat-in kitchen, pantry, separate laundry room, and a comfortable primary suite with walk-in closet and oversized bath. The fabulous outdoor space is where this property shines. Since the home was built, a stunning concrete pool was added in 2022, creating the perfect place to cool off after a day on the water. Relax under the new tiki hut, rinse off in the outdoor shower, challenge friends and family on the putting green, or simply enjoy the constant ocean breezes and beautiful open water views across the street. The oversized fenced lot offers plenty of room to spread out, while the covered front porch and legal downstairs storage provide additional functionality. There's even 50-amp service for an RV or electric vehicle charger. Whether you're looking for a full-time residence, vacation home, or Keys getaway, 174 Tortuga Lane delivers the boating lifestyle, outdoor amenities, and island charm that make the Florida Keys so special.

174 Tortuga Ln, 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
$799,000
2 Beds ⋅ 1 Baths ⋅ 620090 MLS
********Nightly Licensed Transient Rental!!!******** This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking 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, this home offers everything the Keys lifestyle promises - sun, sea, and serenity. Call today for a showing!

701 Spanish Main Dr Unit LOT 49, 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
$895,900
2 Beds ⋅ 2 Baths ⋅ 619710 MLS
Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million! 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 bonus unit, storage and covered porch. 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!

22961 John Avery Ln, Cudjoe
$2,800,000
4 Beds ⋅ 3 Baths ⋅ 619615 MLS
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!!!

21640 Overseas Hwy, Cudjoe
$339,000
2 Beds ⋅ 1 Baths ⋅ 619246 MLS
Great opportunity to own an income-producing home in the gated community of Venture Out on Cudjoe Key. This 2-bedroom, 1-bath mobile home features a cozy layout with a true Florida Keys feel throughout. The property is ideally situated on a private lot with no neighbors on one side or behind, offering added privacy and tranquility. Whether you're looking for a full-time residence or a turnkey vacation rental, this property checks all the boxes. Venture Out is a sought-after waterfront community known for its welcoming atmosphere and exceptional amenities, including a huge, heated saltwater pool overlooking the open ocean, community boat ramp, on-site store and fuel station, as well as pickleball, tennis, basketball, and bocce courts. Enjoy the best of Keys living with investment potential. Don't miss this opportunity to own in one of the Lower Keys' most desirable communities. Brand new mini split system installed 4/10/2026.

701 Spanish Main Dr Unit 28, 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
$595,000
2 Beds ⋅ 2 Baths ⋅ 618979 MLS
Owner says ''Bring All Offers'' Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed. Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and inviting interior, complete with all the essentials for a seamless transition. The open-concept living area flows effortlessly, providing a warm atmosphere for gatherings or quiet evenings. Outside, you'll find a concrete seawall, perfect for fishing enthusiasts and water lovers alike. The included fish cleaning station makes it easy to prepare your catch right at home. With ample outdoor storage space underneath the house, you'll have plenty of room for kayaks, fishing gear, or seasonal decorations. Located in a prime area that allows for nightly rentals, this property is not only a fantastic home but also a lucrative investment opportunity. Whether you're looking to enjoy your own slice of paradise or generate rental income, this home has it all. Don't miss your chance to own this charming coastal retreat. As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the marina store and fuel station. Sports enthusiasts will love the two lighted tennis courts, pickleball, basketball, and bocce courts. The recreation hall and community pavilion host a variety of activities and events, making it easy to connect with neighbors and make new friends. This golf cart-friendly community also features a boat ramp, giving you direct access to the stunning waters of the Florida Keys. Whether you're looking for a vacation home, rental investment, or a permanent paradise, this property has it all!

701 Spanish Main Dr Unit 604, 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
$525,000
2 Beds ⋅ 2 Baths ⋅ 618300 MLS
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 453 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * 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 very well cared for and updated 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! * Excellent rental income potential!!

701 Spanish Main Dr Unit 453, Cudjoe
$879,000
2 Beds ⋅ 2 Baths ⋅ 618239 MLS
This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side is fully equipped with six heavy duty dock posts and cleats, ideal for boating, fishing, and easy water access. This beautifully maintained home features two bedrooms and two full bathrooms, with tile flooring throughout, a metal roof, central air conditioning and abundant storage. The bright, open interior is surrounded by windows galore in the living area, perfectly framing the stunning outdoor scenery and flooding the home with natural light. The primary bedroom opens directly to a large covered porch, where you can wake up to breathtaking sunrises over the Atlantic. Outside, enjoy a spacious patio perfect for evening gatherings, moonrises and watching the incredible sealife. Additional features include accordion shutters and a full line of appliances, making this home as functional as it is beautiful. Located in Venture Out on Cudjoe Key, a private and gated community. Residents enjoy 24 hr gated security and patrol, two pets allowed and transient rentals permitted. The community amenities are unmatched and include: Oceanfront heated saltwater pool, hot tub, marina with ship store, fuel dock, two boat ramps, two tennis courts, two pickleball courts, basketball, bocce ball and playground for the kids. This is a rare opportunity to find your happy place in paradise. Seller says bring offers

701 Spanish Main Dr Unit 265, 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
$535,000
2 Beds ⋅ 2 Baths ⋅ 617289 MLS
Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day on the water. A resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area with tiki huts and more! 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 an exclusive gated community which adds a sense of security and prestige. This home is ready for you to move in and enjoy! Don't miss this rare opportunity to own a piece of paradise! Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 247, Cudjoe
$12,999,999
31 Beds ⋅ 19 Baths ⋅ 610484 MLS
Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

21540 21470 Overseas Hwy, 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
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 617709 MLS
Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while embracing modern luxury. Impact doors and windows, wide-plank engineered wood flooring, and an updated chef's kitchen with gas range create interiors that are both stylish and functional—ideal for relaxed living and elegant entertaining. The serene Primary Suite is a private sanctuary, featuring expansive picture windows that frame stunning views of the home's massive, newly refurbished waterfront pool, evoking a true resort-style experience. Designed for the boating enthusiast, the property offers deep-water dockage on a flow through canal with a concrete dock and 10,000-lb boat lift, providing effortless access to open water. A whole-house generator with automatic transfer switch ensures uninterrupted comfort and peace of mind year-round. Located within one of the Keys' most desirable waterfront neighborhoods, residents enjoy access to the Cudjoe Gardens Marina a full-service marina with fuel, bait, refreshments, and boat ramp, along with a beloved Bent Prop waterfront restaurant—all just moments from home This is a rare opportunity to own a historically significant, architecturally distinctive residence that seamlessly blends mid-century design, modern upgrades, and an unparalleled waterfront lifestyle.

51 Drost Dr, 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