Cudjoe Key Homes with Unfurnished Furnished

Cudjoe Key Homes with Unfurnished Furnished

Welcome to Cudjoe Key, a hidden gem nestled in the breathtaking Florida Keys! Located in Monroe County, Cudjoe Key offers a perfect blend of serene island living and vibrant community spirit. With its idyllic setting, this charming island boasts stunning waterfront views, lush tropical landscapes, and an array of outdoor activities that make it a paradise for nature lovers and adventure seekers alike.

Cudjoe Key is known for its welcoming atmosphere and close-knit community, where neighbors become friends and every sunset feels like a celebration. The island is a haven for boating, fishing, and snorkeling enthusiasts, with easy access to the crystal-clear waters of the Atlantic Ocean and the tranquil backcountry. Whether you’re looking for a quiet day on the water or an exhilarating adventure, Cudjoe Key has it all.

When it comes to finding your dream home, Cudjoe Key offers a delightful selection of unfurnished and furnished properties to suit your lifestyle. Imagine waking up to the gentle sound of waves and enjoying your morning coffee on a spacious deck overlooking the water. Whether you prefer a cozy cottage or a modern waterfront retreat, the homes here are designed to capture the essence of island living while providing all the comforts you desire.

Discover the charm of Cudjoe Key, where every day feels like a vacation. Embrace the laid-back lifestyle of the Florida Keys and make this enchanting island your new home. Your piece of paradise awaits!

Newest Cudjoe Key Homes with Unfurnished Furnished

$819,500
3 Beds ⋅ 2 Baths ⋅ 621169 MLS
Welcome to 22968 Drake Lane -- a charming canal-front home located on the desirable Cudjoe Key, one of the Lower Keys' wonderful communities. Set on a generous 7,500 SF lot with direct canal access and a private boat lift, this property is a true dream for anglers, divers, and boaters looking to get out on the water in minutes. with quick access to the backcountry flats as well as the open water beyond. Inside, the approximately 1000SF living area feels bright and spacious thanks to high ceilings throughout the main living areas. The updated kitchen, featuring granite countertops and stainless steel appliances, perfect for entertaining or everyday island living. Glass sliders lead from the living area out to a large covered porch, where you'll enjoy a peek-a-boo open bay view -- an ideal spot for morning coffee, evening cocktails, or simply soaking in the classic Florida Keys lifestyle.Downstairs, an oversized garage which holds 2 cars and possibly more offers abundant space for vehicles, boats, kayaks, fishing gear, and all the toys that come with life on the water, plus additional storage to keep everything organized. Located on Cudjoe Key in the heart of the Lower Keys, this home offers a peaceful, laid-back setting while remaining just minutes from the vibrant restaurants, nightlife, and culture of Key West. Enjoy easy access to some of the best fishing, diving, and snorkeling grounds in the world, right from your own backyard.Whether you're searching for a full-time residence, a weekend retreat, or a smart investment in one of the most desirable stretches of the Florida Keys, this canal-front gem checks every box. Boat lift, water access, and some updated finishes at this price point are increasingly rare in the Lower Keys market -- schedule your private showing today before this one is gone! A Bonus, this one has the potential for a partial seller financing to the right Buyer and low insurances.

22968 Drake 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
$1,349,000
3 Beds ⋅ 2 Baths ⋅ 620916 MLS
Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry of the Lower Florida Keys, this is the perfect property for the fishing and diving enthusiasts and still only 20 minutes to Key West. Built by Tom Ryan Construction, this solid CBS 3-bedroom 2-bath home is almost 1,300 square feet, and has a spacious, open feel, created by the thoughtful layout and vaulted ceilings in the main living area. The kitchen features granite countertops, a convenient breakfast bar, and a dedicated dining area, making it ideal for both everyday island living and entertaining. The primary suite has a walk in closet and french doors leading out to the porch, while the second bedroom has a pocket door creating another convenient ensuite for guests. Most days you'll enjoy outdoor dining or cocktails and the relaxed island life from the covered, screened porch overlooking the canal with open water views of Kemp Channel. The views continue into the primary suite and kitchen, offering a beautiful waterfront backdrop throughout the home. The lower enclosure provides plenty of space for a vehicle, workshop, and storage. Two 500-gallon cisterns provide ample water for maintaining the lush tropical landscaping. The solid concrete step down seawall features davits each with a 5,500 lift capacity. This property is the ideal location to be able to spend a stellar day on the water, then head to Key West to one of the many fabulous restaurants for dinner, and finish the evening listening to live music or take in a show at one of our unique boutique theaters. You can have it all.

23057 Bluegill Ln, Cudjoe
$949,000
3 Beds ⋅ 2 Baths ⋅ 620535 MLS
Welcome to 342 Spanish Main Drive, a beautiful canal-front home in the heart of Cudjoe Key, offering the perfect combination of waterfront living, modern comfort, and laid-back Florida Keys charm. This two-story residence features 3 bedrooms and 2 full bathrooms, thoughtfully designed for both everyday living and relaxing island escapes. The bright, open interior is move-in ready and includes a stylish eat-in kitchen with stainless-steel appliances, comfortable living spaces, and plenty of natural light throughout. Enjoy the Florida Keys lifestyle from the spacious covered porches on both levels, where you can sip your morning coffee, unwind with an evening cocktail, or simply take in the peaceful canal views. Large sliding glass doors open to the upper porch, creating a seamless indoor-outdoor living experience that's perfect for entertaining family and friends. Boaters will appreciate the canal-front location with dockage directly behind the home, offering plenty of space for your boat and easy access to both the Gulf and Atlantic. Spend your days fishing, diving, exploring sandbars, or cruising the beautiful Lower Keys waters right from your backyard. Additional features include two garages--a rare find in the Keys--along with ample parking for vehicles, trailers, and guests. Conveniently located just 30 minutes from Key West and within walking distance of the iconic Square Grouper Bar & Grill, this property offers the ideal balance of tranquility and accessibility. 342 Spanish Main Drive is an exceptional opportunity as a full-time residence, vacation home, or waterfront investment property. Come experience the boating lifestyle and island living you've been dreaming about.

342 Spanish Main 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
$799,000
2 Beds ⋅ 2 Baths ⋅ 620174 MLS
SELLER ACCEPTING BACK-UP OFFERS: Discover your perfect boater's retreat in beautiful Cudjoe Key! This stilted 2-bedroom, 2-bathroom home is situated on a deep-water canal. Access to both the Atlantic and Gulf is easy and achievable in minutes, making it an ideal base for fishing, boating, and enjoying the Keys lifestyle. One of the home's standout features is its exceptional privacy. With no neighbors across the canal and no neighbors on one side, you'll enjoy peaceful water views and a secluded atmosphere rarely found in canal-front properties. Outside, the property features a 10,000-pound boat lift and davits, providing ample accommodations for your vessels. Downstairs, you'll find enclosed storage for all your gear along with covered parking. Mature tropical landscaping surrounds the property, creating a lush island setting. An RV hookup adds even more flexibility for guests and additional recreational vehicles. Inside, the home offers a wonderful open-concept layout. The kitchen features an abundance of hardwood cabinetry and a center island, creating an inviting space for cooking and entertaining. Off the living room, a spacious screened in deck is accessed through a fully opening sliding glass door, seamlessly blending indoor and outdoor living. High ceilings and beautiful cypress pine accents throughout the home add warmth and character, perfectly complementing the relaxed coastal lifestyle. Whether you're searching for a full-time residence, seasonal getaway, or investment opportunity, this waterfront gem combines privacy, character, boating amenities, and the relaxed island lifestyle that makes Cudjoe Key so desirable.

22822 Buccaneer Ln, Cudjoe
$895,000
3 Beds ⋅ 2 Baths ⋅ 620163 MLS
If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and Bahama shutters, this home is virtually maintenance-free and hurricane-resistant. Clean, solid, and move-in-ready, the only thing it needs is a little cosmetic updating to reflect your personal style. Come see it today and imagine making it your own.

135 Tortuga Ln, 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
$1,269,000
2 Beds ⋅ 2 Baths ⋅ 619922 MLS
Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has been thoughtfully updated to offer the ultimate waterfront lifestyle, just 21 miles from Key West's world-class dining and entertainment. The interior glows with natural light, highlighted by impact-resistant windows and elegant French doors leading to an open canal front balcony. The floor plan is designed for effortless living, featuring a sleek kitchen with a central island, 2025 updated Oven, Dishwasher, & microwave, remodeled bathrooms, a versatile bonus room, and a separate dining area that provides a front-row seat to the tranquil canal. For added convenience, the spacious walk-in closet includes an integrated washer and dryer, while a temperature-controlled thermostat and security system ensure year-round peace of mind. Perfectly situated for the avid mariner, the exterior features a concrete dock and a 10,000lb elevator boat lift. The lift currently accommodates a 2024 Boston Whaler 250 Outrage with twin 200hp Mercury Verado engines (no trailer), which is available for separate purchase. Enjoy a short, scenic canal ride from your backyard directly to the open ocean. Step outside into a secluded tropical retreat. The exterior boasts brand-new Hardie Board siding and a privacy fence encompassing an inground concrete pool finished with an elegant travertine pool deck. Beneath the home, a shaded entertaining space provides the perfect spot for lounging, complete with an outdoor shower and ample storage for kayaks, grill and water toys. Complete with a dedicated garage and plenty of parking, this property is the perfect home for family enjoyment as a primary residence or a seasonal retreat. Whether you are looking to make wonderful lifelong memories or simply wish to offset ownership expenses with a winter rental, this Cudjoe Key gem captures that sought-after ''Keys feel'' in every

116 Spanish Main Dr, Cudjoe
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 619865 MLS
Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a private island atmosphere while the standing seam galvanized roof and concrete construction provide lasting durability and peace of mind. Inside, the home radiates warmth and coastal character. Vaulted wood tongue-and-groove ceilings draw your eyes upward and create an airy, open feel throughout the living spaces. The thoughtfully designed floor plan flows seamlessly between the kitchen, dining, and living areas, making the home ideal for entertaining family and friends after a day on the water. The kitchen is both stylish and functional with updated stainless appliances, generous cabinetry, pantry and a large dining bar for casual dining. Picturesque pool and water views are enjoyed from the living areas and primary suite. Outside is where this property truly shines. The new waterfront pool creates a resort-style centerpiece from the living area and is surrounded by multiple lounging and entertaining spaces. Relax beneath the tiki hut with a morning coffee, gather around the waterfront firepit at sunset, or enjoy evenings under the stars with the gentle breeze coming off the canal. For boating enthusiasts the deep-draft canal accommodates larger boats with a new 17K boat lift and quick ocean access. The nearby full-service marina offers fuel, bait, refreshments and boat ramp access while the neighborhood waterfront restaurant adds another layer of convenience and charm. Plenty of room for of your gear and toys in the 2-car attached garage. Located 20 minutes from Key West offering the perfect balance between peaceful island living and access to world-class dining and culture.

21012 6th Ave, 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
$949,000
3 Beds ⋅ 2 Baths ⋅ 619680 MLS
Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment. Thoughtfully renovated throughout, the home showcases a clean coastal-modern design with new impact windows and doors, an elevated interior finish, and a beautifully updated kitchen featuring sleek cabinetry, premium surfaces, and an open layout ideal for entertaining. Light-filled living spaces flow seamlessly onto the newly replaced covered rear porch, where tranquil canal views create the perfect backdrop for relaxed indoor/outdoor living. The exterior stairs have also been recently replaced, complementing the home's refreshed and well-maintained feel. Boating enthusiasts will appreciate the 10,000 lb boat lift, expansive seawall/dockage, and quick access to open water via Cudjoe Bay. Downstairs, a large enclosure provides abundant storage space for tools, fishing gear, and boating equipment, an invaluable feature for Keys living. Located on a quiet street in an established neighborhood, this property offers a rare combination of modern updates and generous waterfront in the Lower Florida Keys.

22953 John Silver Ln, Cudjoe
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