Cudjoe Key Homes with Fence Exterior features

Cudjoe Key Homes with Fence Exterior features

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys! This enchanting island, part of Monroe County, offers a unique blend of tropical paradise and serene living. Just a short drive from Key West, Cudjoe Key is renowned for its stunning waterfront views, vibrant marine life, and laid-back atmosphere, making it the perfect destination for those seeking a slice of island life.

Cudjoe Key boasts an array of charming homes, many featuring desirable fenced exteriors that provide both privacy and security. Imagine enjoying your morning coffee on a sun-drenched patio, surrounded by lush landscaping and the gentle sound of waves lapping against the shore. These homes are not just structures; they are sanctuaries where you can create lasting memories with family and friends.

The community here is tight-knit and welcoming, with a variety of recreational activities at your fingertips. Whether you’re into fishing, boating, or simply soaking up the sun, Cudjoe Key offers an abundance of outdoor adventures. Explore the nearby natural parks, take a leisurely stroll along the picturesque coastline, or indulge in fresh seafood at local eateries.

With its stunning homes featuring fenced exteriors, Cudjoe Key invites you to embrace a lifestyle of tranquility and beauty. Discover the charm of this idyllic island and let it inspire your dreams of homeownership in the Florida Keys. Your slice of paradise awaits!

Newest Cudjoe Key Homes with Fence Exterior features

20731 W 2nd Ave, Cudjoe
$3,200,000
5 Beds ⋅ 4 Baths ⋅ 621433 MLS
Experience exceptional boating and effortless Florida Keys living from this meticulously maintained Cudjoe Key residence, ideally positioned on a wide canal just 2 homes from open water. Lush tropical landscaping surrounds the property, while protected wetlands across the canal create a peaceful, private backdrop. Offering 4 Bedrooms plus an Office and 4 Baths, the home features 112' of concrete seawall and dockage, a 20,000 lb. boat lift and quick access to open water. Designed to embrace indoor-outdoor living, the living room features a Euro Door Wall System with sliders that open completely to the expansive screened porch with sitting and dining areas. Remote-controlled Kevlar hurricane screens provide added protection, while the waterfront retreat features a heated and chilled saltwater pool, poolside tiki, travertine decking and outdoor shower. With the rear of the home facing west, unforgettable Florida Keys sunsets unfold over the water and protected wetlands. The kitchen features granite countertops, Wolf cooktop, Electrolux large capacity refrigerator, wine cooler and dedicated ice maker. The spacious primary suite offers a soaking tub, walk-in shower and dual vanities. One guest bedroom features an ensuite bath, while 2 additional guest bedrooms share a Jack-and-Jill bath. A dedicated office adds flexible space. Additional features include a laundry room with dog wash, 2-car garage with convenient side access to the waterfront, and impact windows and doors. A nearby full-service marina and waterfront restaurant add to the ease of this sought-after boating neighborhood. Beautifully maintained inside and out, this property captures the privacy, boating access and outdoor lifestyle that make the Florida Keys so special.

20731 W 2nd Ave, Cudjoe
1106 Thatch Ln, Cudjoe
$2,099,000
4 Beds ⋅ 4 Baths ⋅ 621161 MLS
Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

1106 Thatch Ln, Cudjoe
94 Sacarma Dr, 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
125 Colson Dr, Cudjoe
$2,195,000
5 Beds ⋅ 3 Baths ⋅ 620325 MLS
TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

125 Colson Dr, Cudjoe
20833 W 4th Ave, 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
174 Tortuga Ln, 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
21023 2nd Ave, Cudjoe
$2,499,000
4 Beds ⋅ 2 Baths ⋅ 620071 MLS
Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and effortless waterfront living, the 2,739-square-foot home features 4 bedrooms, a spacious open-concept great room, bamboo flooring, impact windows and doors, and a durable metal roof. The chef's kitchen is the heart of the home, offering a large center island, stainless steel appliances, abundant cabinetry, and a wine refrigerator and is the perfect gathering place for entertaining family and friends. Step outside to a beautifully landscaped tropical setting with expansive screened lanai overlooking the water and an 82-foot dock complete with boat lift and kayak launch. Whether you're heading offshore for a day of fishing, enjoying sunset cruises, or simply relaxing by the water, this property delivers the Keys lifestyle you've been dreaming about. The 2- car Garage offers plenty of parking and room for all or your toys while the oversized double lot provides privacy and space to enjoy the outdoors while taking advantage of the home's unique corner-like waterfront setting. Located in one of the Lower Keys' most desirable boating communities, Cudjoe Gardens offers deep-water canals capable of accommodating larger inboard vessels, plus convenient access to a full-service marina with fuel, bait, boat ramp, refreshments, and a waterfront restaurant. Just 20 minutes from Key West, you'll enjoy world-class dining, entertainment, and island living while returning home to a peaceful waterfront retreat.

21023 2nd Ave, Cudjoe
22939 Gasparilla Ln, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 619835 MLS
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.

22939 Gasparilla Ln, Cudjoe
21090 5th Ave, Cudjoe
$3,099,000
4 Beds ⋅ 3 Baths ⋅ 619589 MLS
Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 3 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

21090 5th Ave, Cudjoe
20868 W 5th Ave, Cudjoe
$1,150,000
2 Beds ⋅ 2 Baths ⋅ 619465 MLS
Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man made sandy beach, concrete seawall, and boat lift, making it a boater's dream with easy access to open water. Relax and entertain in true Keys fashion with a spacious patio, tiki hut, and outdoor shower Perfect after a day on the water. The garage provides added storage and convenience, while the cozy layout makes this home ideal as a full time residence, vacation getaway, or investment property. Located just minutes from Cudjoe Gardens Marina, local dining favorites, and world-class fishing and diving, this home offers the perfect blend of tranquility and adventure. Experience laid back coastal living at its finest your Keys escape awaits!

20868 W 5th Ave, Cudjoe
22978 Port Royal Ln, Cudjoe
$875,000
2 Beds ⋅ 1 Baths ⋅ 619325 MLS
Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully landscaped. Two large storage sheds with additional interior storage underneath the home. Here is a piece of paradise to grab and hang onto too. Only 20 minutes to Key West. Seller motivated Seller is motivated to sell this one of a kind location with private boat ramp with 90 feet of concrete seawall. Very large property* Plenty of room for all your requirements can keep R/V , boat trailer, extra vehicle and more* OCEAN SIDE* Some of the best boating opportunities in the Florida Keys* Great Opportunity for affordable canal front home *

22978 Port Royal Ln, Cudjoe
21540 21470 Overseas Hwy, 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
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