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Cutthroat Harbor Est Properties for Sale in Cudjoe Key, FL

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Total Listings 26
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$699,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,056 SqFt Days Listed: 115
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

Charming fishing bungalow located on oceanside Cudjoe Key just waiting to be yours. This waterfront haven features two bedrooms, two bathrooms and just under 1,100 square feet inside plus a permitted downstairs enclosure with plumbing and electric. Enjoy room for all to entertain in the open concept living area that seamlessly leads into the kitchen and dining. Waterside screened porch allows for views of the canal from above, or stroll to the open porch from the primary bedroom for an evening cocktail. With easy Ocean access through Cudjoes canal system, venture by boat to fish and dive the turquoise waters in the Florida Keys. Situated on a spacious 6,000 square foot lot, there is ample space for outdoor living, including the vast potential for lush landscape, a private pool, or expansive tiki. Be enamored by all of the gorgeous fruit trees onsite, including mango, lemon, lime, guava, coconut and even grapefruit! Downstairs, find an outdoor shower to rinse off the salt water, permitted enclosed storage space ideal for all anglers equipment, carport parking for one car, open parking for multiple vehicles and a covered space ideal for lounging after a day on the water. Conveniently located down the street from the famous Square Grouper and other local eateries.

$745,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 158
-6.76% ($54,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 62ft.

Coastal Paradise: 2-Bedroom, 2-Bath Canal-Front Home with Direct Ocean AccessThis stunning 2-bedroom, 2-bath home offers the ultimate canal-front lifestyle, minutes from open water with no bridges to navigate, perfect for boating enthusiasts. Located on the coveted Oceanside, the property features a spacious 60-foot dock ready for your vessel, offering convenient and quick access to the ocean.Inside, the open-concept living area invites relaxation, with natural light pouring in and serene water views. Enjoy seamless indoor-outdoor living with two screened patios--ideal for entertaining, morning coffee, or evening sunsets. A 2-car garage provides ample storage for vehicles and gear, enhancing both convenience and security.Move-in ready and primed for your personal touch, this home is a rare gem in a prime location. Dont miss your chance to own a slice of waterfront paradise!

$835,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 948 SqFt Days Listed: 62
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

Its Five OClock Somewhere or so say guests in this comfortable Cudjoe Key canalfront home.The new Buyer can call this delightful 2 bed 2 bath HOME or it can continue as a successful vacation rental for many years to come. With the new 60 concrete dock , all will enjoy ease of secure tie up and calm canal waters to the open water of Cudjoe Bay.

$849,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,560 SqFt Days Listed: 21
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Mariners Dream - Your Waterfront Paradise Awaits! Welcome to this elevated, stilted two-story home offering 1,560 SqFt of living space and a versatile 4th bedroom that doubles as a den. Situated on a deep, wide, and pristine canal in the desirable Cutthroat Harbor Estates of Cudjoe Key, this home provides the perfect canvas for renovation. With new windows and siding (Completed 2023), much of the heavy lifting has already been completed. Step outside your door to immediate access to the water, whether youre fishing, swimming, or simply soaking in the serene canal views. The 3 control depth provides crystal-clear water ideal for swimming, and theres plenty of space to add your own dock, with or without a boat lift. This home is perfect for those who appreciate the beauty of coastal living and are ready to invest a little elbow grease into transforming it into a dream waterfront retreat. NUTS & BOLTS: Large bonus space enclosure under the house opening up to the waterfront tiki bar; New windows (9) & Hardy-board Siding; 3-ton AC (1998) ; Lower enclosure (1991) Newer wood stilt piers, front and waterfront decks Tiki bar (needs restoration) ; Laundry room off the kitchen. Make this Mariners Dream your very own and embrace the ultimate coastal lifestyle!

$875,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,088 SqFt Days Listed: 32
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift62ft.Cut/Na

Welcome to your dream waterfront property! Nestled in tranquil and desirable Cudjoe Key, this exquisite canal-front residence offers an unparalleled fusion of luxury, convenience, and tranquility. Whether you seek a permanent residence, a vacation retreat, or an investment property, this home offers a waterfront paradise for any lifestyle. This meticulously crafted two-bedroom, two-bathroom, elevated home spans 1,088 square feet of contemporary living space. Upon entering via stairs or your private elevator, you will be captivated by the seamless integration of indoor and outdoor living. The expansive screened patio provides an ideal setting for morning coffee or evening cocktails while immersing you in the breathtaking vista. Situated along a deep-water canal with a 15,000 lb boat lift, the property provides direct access to the Atlantic Ocean. Whether you are an avid boater, kayaker, or fisherman, you will appreciate the ease of accessing the water and enjoying Floridas renowned marine life. For those seeking a permanent home, the serene neighborhood and ample living space make it an ideal place to establish roots. If you are seeking a getaway, this property offers the ultimate retreat, providing relaxation and recreational opportunities within easy reach. For investors, the desirable waterfront location and modern amenities render it an exceptionally attractive rental property with substantial income potential. The proximity to Key West ensures that you are conveniently accessible to a vibrant array of dining, shopping, and entertainment options. Schedule a showing today and immerse yourself in the enchantment of this waterfront gem.

$885,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift62ft.

If youre looking for the ultimate Island Life this charming canal-front home in sought-after Cutthroat Harbor Estates is exactly what you need. This 2 Bedroom 2 Bath home is located on the ocean side with excellent boating access to the Atlantic & Gulf. This home includes a #10,000 pound boat lift, full concrete seawall, large storage area below, and a fully fenced yard, making it a perfect fit for the fishing and diving enthusiasts. Nestled in a tranquil quaint little neighborhood, this inviting Cudjoe Key home offers quiet streets lined with swaying palms and lush tropical foliage, creating the perfect setting for leisurely strolls or evening bike rides taking in the sunset. The interior is full of Keys character, and has been very well maintained. The living area is bright and spacious and well thought out with large bedrooms and a nice sized dining area right off of the kitchen. The huge covered screened back deck overlooking the canal is the perfect spot to enjoy dinner and cocktails al fresco while talking about your incredible day on the water. The Florida Keys offers world class fishing and diving, as well as the most beautiful pristine backcountry islands with reef patches, sand flats, and channels to explore. This prime location in Cudjoe Key is just a short drive to Key West, where youll discover fabulous restaurants, world famous bars with nightly entertainment, and the rich culture of Old Town with a lively art scene including several intimate theaters. Or choose to immerse yourself in our unique ecosystem on the water or on the Florida Keys Overseas Heritage Trail, a scenic route spanning over 90 miles with paved bike paths connecting Key Largo to Key West where you will encounter a diverse array of aquatic birds in their natural habitat. This location has something for everyone.

$899,900
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 507
-5.17% ($49,100) 1 Price Change : Last Change 208 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Excellent boating at this gorgeous Cudjoe Key retreat! Enjoy no-bridge access to Cudjoe Bay for frequent boating and fishing adventures with ease. Inside this well-maintained home, the main living area boasts high ceilings and an open concept. The well-equipped kitchen features stainless steel appliances, abundant storage, and a large kitchen island ideal for entertaining. Two sets of sliding glass doors lead out to a generous open back porch complete with partial Open Water Views, a serene spot for sipping morning coffee or enjoying evening cocktails with friends. The sizeable primary suite boasts a large walk-in closet and en suite bathroom. An additional guest bedroom provides comfortable accommodation for visitors and an upstairs laundry room offers added convenience. Bonus structural features include sturdy Hardie Board Siding and Metal Roof. Downstairs, a spacious storage space houses room for storing tools and equipment out of the elements. The manicured yard features an outdoor shower and a substantial side yard with raised flower beds for gardening. A covered downstairs patio offers an ideal spot for grilling your fresh catch or dining al fresco. Enjoy an abundance of covered and open parking, as well as room for trailer or RV storage. Situated on a deep-water canal with approximately 36 feet of concrete dockage, boasting fillet station and swim ladder, this exceptional property is tailor-made for enjoying the coveted Florida Keys lifestyle! Nestled within a quiet, established neighborhood but just minutes to delectable dining options and stores in town, this fantastic property has it all!

$949,900
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,142 SqFt Days Listed: 53
-4.53% ($45,100) 1 Price Change : Last Change 9 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Dont miss this immaculate home at 22971 Hawkins Ln Cudjoe Key. This completely furnished 3 bedroom 3 bath home is in impeccable condition with recent upgrades to include all new kitchen and appliances, new baths, impact windows, AC, metal roof and paint. The third bedroom could be utilized as an office, gym, yoga or media room. The home also has a walk around deck with a covered screened porch. The property boasts an amazing yard with many mature trees and blooming ornamentals. Follow your custom paver driveway to the covered parking and take the paver walkways for your tour of the fauna and flora. Enjoy the wide 60 concrete dock with a 10,000 lb boat lift. Once youre off the boat lift you will be in one of the most clear, clean beautiful deep canals in all of the Florida Keys. The boat ride is a very short distance to the open water, with great access to the Gulf and Atlantic Ocean for your boating enjoyment and a view of the open water down the short canal. With multiple marinas just a short distance away youll have easy access for fuel, bait, snacks and drinks. It also boasts a nice storage room downstairs and a separate rod and reel tackle room or tool storage. Weve looked at the competition and feel this is a must see...you dont want to miss this Florida Keys dream house!!! Easy to show. Youre going to love this one!!!!

$950,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,344 SqFt Days Listed: 70
-4.52% ($45,000) 1 Price Change : Last Change 9 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: 30ft.

Beautiful 3 bedroom 2 bathroom elevated island retreat on Cudjoe Key. This property features a private dock so you can keep your boat on site and enjoy immediate access to world class fishing and diving the stunning waters of the Florida Keys. Located just 25 minutes to Key West and 3 hours from Miami with grocery store, restaurants and bars close by. The exterior features hard plank siding and hurricane shutters for all windows. Interior has an open great room, bright and inviting kitchen with wood cabinets and sleek granite countertops. Offered fully furnished and move in ready- includes fully outfitted kitchen, linens, towels etc! The primary en suite provides a relaxing retreat with a jetted tub-shower combo, while the hall bath is equally stylish with a granite-top vanity and a walk-in shower. Fans in all living spaces and on the screen porch and lower living area. Step outside to the covered and screened, rear porch and tropical yard, complete with an orchid house, perfect for nature lovers and gardeners. Additional highlights include 2 spacious storage areas beneath the home, ideal for your tools and gear. Enclosed outdoor shower with hot and cold water. Paver driveway and epoxy coated covered parking area/ lounging area.This home truly embodies the Florida Keys lifestyle. With its unbeatable location, tropical charm, and modern conveniences, its the perfect place to start your next adventure. Schedule your private showing today!

$1,049,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,195 SqFt Days Listed: 34
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift40ft.Concre

Welcome to Blackbeard Lane on Cudjoe Key, a stunning stilted home that perfectly combines modern elegance with the charm of the Florida Keys. Built in 2012 and thoughtfully updated, this property boasts 3 bedrooms and 2 bathrooms across 1,195 sq. ft. of beautifully designed living space.The heart of the home is the expansive open-concept living area, seamlessly connecting to a chefs kitchen adorned with high-end appliances, custom cabinetry, a pot filler, and a striking Dade County Pine hood. The primary suite features an ensuite bathroom with custom finishes and generous walk-in closets, while two additional guest rooms share a stylish guest shower.Attention to detail is evident throughout, from the contemporary flooring to the Dade County Pine accents. The home is equipped with impact-resistant windows and a newer roof (2018), ensuring low insurances and peace of mind. Set on a spacious 6,000 sq. ft. lot, this property is a true boaters paradise, featuring a 40-foot seawall and a 10,000 lb boat lift, making it easy to explore nearby destinations like the American Shoal Lighthouse and Looe Key Sanctuary. Additional amenities include an outdoor shower, ample parking, and a downstairs enclosed garage for extra storage.Experience the best of Florida Keys living in this exceptional home!Property is owned by a licensed Real Estate Agent.

$1,095,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,620 SqFt Days Listed: 83
-8.75% ($104,999) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

Welcome to your private tropical oasis in the Lower Florida Keys! This beautifully maintained waterfront home is perfectly situated on a quiet street in the desirable neighborhood of Cutthroat Harbor Estates on Cudjoe Key. Boasting 3 bedrooms, 2 bathrooms an open-concept living area, this property is designed to embrace the laid-back island lifestyle.Step inside to find a bright and airy interior with vaulted ceilings, large impact rated windows, and sliding glass impact rated doors that give the home natural light. The kitchen features a heart of the house concept, and a convenient breakfast bar, making it perfect for entertaining.Outdoors, youll discover a spacious patio overlooking a deepwater canal with direct access to the open ocean and the Gulf of Mexico. The property includes a 60-foot concrete dock, making it ideal for boating, fishing, or diving adventures.Additional features include a large lot with lush landscaping, plenty of storage for your gear, covered parking, and room for an RV or trailer. If youre looking for a full-time residence, a vacation retreat or an investment property, this home offers it all.Enjoy the beauty of the Florida Keys and the convenience of being just 20 minutes from Key Wests dining, shopping, and entertainment. Schedule your private tour today and start living the dream!*Please note 3rd bedroom is open air

$1,135,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,008 SqFt Days Listed: 267
-1.30% ($15,000) 1 Price Change : Last Change 159 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Davit Pads

Open Water Views & Sunset Skies with great boating access describes this Concrete Block Construction Home with pre-stress concrete beams holding up a poured concrete floor.... Lot to the east is available for sale at additional price. Home features open floor plan with vaulted ceilings, tile floors throughout, partial walk-around, storm shutters, 2018 A/C, impact front door and metal roof. Storage room below and ample parking too. Quick commute to Key West, shopping, restaurants and all other conveniences. Excellent Oceanside boating access to the best fishing and diving spots in the Lower Keys. Enjoy the outdoors and gorgeous sunset skies on your screened porch facing the canal & Cudjoe Bay.....Great Home and Great Location!

$1,175,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,260 SqFt Days Listed: 27
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 820ft.

Welcome home to your coastal oasis! This stunning brand-new elevated home features three bedrooms, two bathrooms, with an open concept living room and kitchen plus a covered 10x30 porch. Additional features include impact resistance windows and doors, metal roof, Azek decking, powder coated aluminum railings, custom concrete dock (8x20) with a permitted 12,000 Ibs. boat lift with your very own private beach and 298 sq. ft. of enclosed storage space. Schedule your private showing today! One of the Sellers is a Licensed FL Real Estate Sales Associate.

$1,200,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,120 SqFt Days Listed: 112
-6.61% ($85,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift

Welcome to your stunning 3-bedroom, 2-bathroom oasis, nestled at the end of a peaceful cul-de-sac on a double canal. Surrounded by lush fruit trees, this home offers the perfect blend of tranquility and luxury. Step inside to find a spacious open floor plan that creates a bright and airy atmosphere, ideal for entertaining. The chef-friendly kitchen is equipped with modern appliances, making it a culinary enthusiasts dream. The tranquil master retreat overlooks the pool and features a spacious bathroom complete with a jetted tub for ultimate relaxation. The guest bedroom offers its own access to the guest bath, along with a walk-in closet and serene water views. This home is truly a haven for outdoor lovers. With over 200 feet of waterfront, youll have ample space for all your water activities. Enjoy the convenience of a 14k boatlift and 10,000k davits, perfect for boating enthusiasts. For those who love to fish, theres a dedicated fish cleaning table and tackle storage. After a day on the water, refresh yourself in the outdoor heated shower. OFFER COMPLETELY FURNISED

$1,250,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,482 SqFt Days Listed: 12
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Waterfront Paradise in Cudjoe Key - A Boaters Dream!Welcome to your own piece of paradise on the highly sought-after island of Cudjoe Key! Just 22 miles from the vibrant energy of Key West, this stunning waterfront home offers the perfect blend of tropical tranquility and modern convenience.Boasting an impressive 120 feet of waterfront, this property provides exceptional boating opportunities with direct access to the open ocean and the serene backcountry waters. Whether youre an avid fisherman, kayaker, or sunset cruiser, this location is ideal for all your water adventures.The beautifully maintained three-bedroom, two-bathroom home features an open floor plan, creating a bright and airy living space perfect for entertaining or unwinding after a day on the water. Large windows and sliding glass doors fill the home with natural light while offering breathtaking canal views.Step outside to the expansive patio, where you can enjoy your morning coffee while taking in the gentle island breezes or host evening gatherings under the stars. With a spacious 12,000-square-foot lot, theres plenty of room to create your own backyard oasis--whether that means installing a large pool, tiki bar, or outdoor kitchen.Additional features include:2018 Metal Roof - Built for durability and peace of mind598 sq. ft. of downstairs storage - Perfect for all your gear and toolsAmple space for parking - Bring your boat, RV, or jet skisPotential for an accessory structure - Customize to fit your needsThis rare waterfront gem is your chance to experience the Florida Keys lifestyle at its finest. Dont miss out--schedule your private showing today and start living your island dream!

$1,299,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
4 Bed, 4 Baths, 2,448 SqFt Days Listed: 134
-3.71% ($50,000) 1 Price Change : Last Change 22 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 50ft.Concrete

This stunning 4 bedroom, 3 bathroom canal front home offers the perfect blend of functionality and luxury. With 2,448 Sq. Ft. of living space this home is perfect for large familys, the property features an expansive covered balcony on both floors and a large kitchen / dining room for entertaining. The updated bathrooms and spacious master suite provide a comfortable retreat, while the exterior offers plenty of space for off-street parking and room for a pool. There is a downstairs enclosure for extra storage. Great water access to the Gulf and Atlantic. Awesome restaurants and bars within walking distance. Bring your boat and come enjoy the Florida Keys!

$1,399,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 74
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift

Embrace the ultimate Keys lifestyle in this spacious 1,500 sqft home, ideally situated along a boating canal in the Lower Florida Keys, and close to Key West!Tucked away in a quiet, peaceful neighborhood.Inside, the home features generous living space, providing ample room to stretch out and make it your own. Indoor-outdoor living is at its best here, with a private swimming pool just steps from the back door--perfect for unwinding after a day on the water or enjoying sunny Florida afternoons.For boaters, the canal location offers easy water access, along with the convenience of a 10,000-pound boat lift to safely store your boat out of the water. After a day of fishing, cruising, or exploring, dock your vessel with ease and relax as you take in the beautiful waterfront views.The lower enclosure offers abundant storage space for all your tools, pool toys, and outdoor gear, keeping everything organized and clutter-free. Plus, with a newly built home designed to the latest building codes, youll benefit from low insurance rates, ensuring peace of mind and minimized risk from tropical weather.This home offers the ideal combination of comfort, convenience, and the laid-back Florida Keys lifestyle. Dont miss the opportunity to make it yours--schedule your private showing today!COMING SUMMER 2025 - photos of listing do not fully represent dwelling unit, subject to change. Photos are of model home. Construction process underway. Some build selections may be considered. Seller is licensed FL real estate agent.

$1,399,999
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,674 SqFt Days Listed: 65
-3.45% ($50,000) 1 Price Change : Last Change 12 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.Concre

A luxurious turn key, waterfront estate that is situated on an expansive double lot in Cudjoe Key, boasting over 260 feet of pristine shoreline. The property features a newly installed 14,000 pound boat lift, and 60 concrete dock. Majestic Royal palm trees, and an elegant double staircase enhance the propertys sophisticated facade. This flood-elevated, 3BR/2BA residence showcases an open-concept living space that separates the primary bedroom from the other bedrooms and bathroom. The primary suite features a renovated private bath and French doors that capture refreshing ocean breezes. This home has contemporary finishes, premium granite countertops, high-end stainless steel appliances, a newly added designer quartz island, fresh paint, hurricane-rated impact windows & doors, metal roofing, a wraparound veranda, and meticulously planned low-maintenance grounds. The generous lot size allows for numerous luxury additions including a pool, tiki huts, RV accommodation, and beyond. This home encompasses the Florida Keys lifestyle inside and out.

$1,450,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 19
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Boat

Quite Active Community! Stunning waterfront 3-bedroom, -bathroom home nestled on a serene canal with breathtaking ocean views and abundant natural light. Completely renovated in 2022, this residence showcases exceptional quality throughout. The open-concept kitchen features a spacious island, all-new premium cabinetry, and top-of-the-line appliances, perfect for entertaining. The luxurious master suite includes a large walk-in closet and an elegant ensuite bath boasting a new vanity, stylish tile, and frameless glass shower.Meticulously updated with new plumbing and electrical systems, the home also includes a newer roof, AC, and water heater (all replaced in 2018) for worry-free living. Outdoors, experience your personal resort oasis featuring a beautifully landscaped, fully fenced yard, complete with a new heated and cooled pool and spa, inviting Tiki Hut grill area, and convenient outdoor shower.Enjoy peaceful mornings or relaxing evenings on the expansive wrap-around porch offering picturesque water views. A bonus 320 sq. ft. screened-in living space below provides versatile options for storage, a workspace, or relaxation area, including a charming additional bathroom with a delightful surfer-inspired design.Ideal for boating enthusiasts, the property includes a 10,000 lb. boat lift for easy ocean access. Situated in a quiet and friendly neighborhood located conveniently behind the renowned Square Grouper, the home offers both tranquility and proximity--only 20-25 minutes to vibrant Key West.With neighbors who are rarely present and do not rent their homes, youll appreciate exceptional privacy and quiet. This property is perfect for those seeking a peaceful full-time residence, vacation home, or investment rental opportunity. Motivated sellers--dont miss your chance to own this tropical paradise in the heart of the Florida Keys!

$1,495,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 2,100 SqFt Days Listed: 97
-6.56% ($105,000) 2 Price Changes : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 75ft.Concrete

Nestled in the serene and sought-after community of Cudjoe Key, this stunning Glen Gray Build two-story home offers the perfect blend of comfort, luxury, and coastal living. With three spacious bedrooms and two beautifully appointed bathrooms, this home is designed for both relaxation and entertaining, featuring exceptional outdoor spaces, waterfront access, and breathtaking ocean views.Key Features:3 Bedrooms, 2 Bathrooms: The home boasts generously sized rooms, each designed with modern finishes and thoughtful details. The master suite provides a peaceful retreat, complete with scenic views and ample closet space.Glen Gray Build Construction: Known for its quality craftsmanship, this well-built home stands as a testament to durability and timeless design.Expansive Two-Story Layout: With its open concept living spaces, the home allows for seamless indoor-outdoor living. A large living room and dining area flow effortlessly into the kitchen, offering a bright and airy atmosphere, perfect for entertaining family and friends.Outdoor Living & Water Access:Private Pool: Step outside to your private oasis. The sparkling pool is surrounded by lush tropical landscaping, offering a tranquil setting to relax and unwind after a day on the water.Seawall & Boating: Located along the water, the home includes a 75ft seawall, providing easy access for boating, kayaking, or fishing. Whether youre an avid boater or simply enjoy waterfront views, this home is perfectly situated for outdoor adventures.Spacious Decks & Balconies: With multiple decks, including a large upper balcony, you can enjoy ocean views.. The decks offer ample space for dining, lounging, or simply taking in the beauty of the Florida Keys.

$1,599,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,127 SqFt Days Listed: 129
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp54ft.

Breathtaking Open Water Home in Cudjoe Key thats comes FULLY FURNISHED. Welcome to paradise! This stunning 2-bedroom, 2-bath home offers magnificent open water views and the ultimate Florida Keys lifestyle.Main Floor: Spanning 784 sq. ft., the first floor features an open-concept kitchen, living room, and dining area, all bathed in natural light. A full bath completes this level, providing convenience and comfort.Second Floor Master Suite: Retreat to your private sanctuary--a 343 sq. ft. master suite with panoramic water views to greet you every morning.Outdoor Living: Enjoy a full wrap-around porch, offering ample space to unwind and take in the stunning open water views and the refreshing ocean breeze. This expansive porch is ideal for outdoor living, whether relaxing or entertaining.Prime Location: Located in a highly sought-after area with easy access to open water, plus a boat ramp for added convenience+50AMP RV Service w/ room to park a class A motor home on side.This home is perfect for those who love boating, fishing, or simply savoring the beauty of the Keys. Dont miss your opportunity to own this waterfront gem!Comes with 6 exterior security cameras with room to add 10 more

$2,175,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
4 Bed, 4 Baths, 2,074 SqFt Days Listed: 126
-11.22% ($275,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 32ft.

Welcome to paradise at 22562 Jolly Roger Dr in beautiful Cudjoe Key! This custom built, 4-bedroom, 2-bath home features open water views, a designer kitchen with high-end finishes and Viking appliances. In addition, on the first floor there are two guest bedrooms, an office and bathroom. The second floor is where you will find the third bedroom as well the primary bedroom complete with private balcony, ensuite bathroom and walk in closet. Outside the property boasts double decker porches, covered hot tub, full swim spa, and new dock. In addition to the garage there is ample room for vehicles, boats and extra storage. The property is equipped with RV electrical and sewer hookups for added convenience. The property features impact windows and doors and is a stones throw from American Shoal, Lighthouse, Looe Key Reef, and Square Grouper restaurant.

$2,195,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
2 Bed, 2 Baths, 1,292 SqFt Days Listed: 71
-4.36% ($100,000) 1 Price Change : Last Change 5 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage22ft.

Experience the epitome of Florida Keys living in this stunning luxury waterfront home on Cudjoe Key. The back of the home has a South West Exposure, for endless ocean views and spectacular nightly sunsets. Constructed with poured concrete for unmatched durability and featuring a poured concrete floor, this home is a sanctuary of modern design and functionality. The property boasts impact-rated windows and doors installed in 2016, including custom 5-panel EuroWall stacking doors that create a seamless indoor-outdoor flow. Modern elegance is evident throughout, with stainless cable railings and a zero-grout tiled walk-around porch. Offered furnished with Restoration Hardware and Room & Board pieces valued at approximately $45,000 (art excluded), also includes TVs.The outdoor spaces feature a heated pool featuring a Coralina stone deck sourced from the Dominican Republic, designed to stay cool underfoot. New pool equipment, including a heater and pump installed in 2018. Boating enthusiasts will appreciate the 21.5 wood dock with a Slide-Moor Dock system, complete with water access, as well as a floating dock system perfect for kayaking and paddleboarding. The propertys tropical landscaping, accented with solar yard lighting & cozy lounge areas create wonderful, private space to enjoy serenity or entertain guests.The gourmet kitchen, updated in 2022, features quartz countertops, modern blue cabinets, and Samsung Bespoke appliances. Dont miss your chance to own this luxury retreat in the heart of Cudjoe Key. Just 22 miles to Key West and 3 hours from Miami. Fantastic bar/ restaurant/ and coffee shop within walking distance!

$2,395,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
4 Bed, 4 Baths, 2,440 SqFt Days Listed: 128
-4.01% ($100,000) 1 Price Change : Last Change 60 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

SELLER FINANCING AVAILABLE! This Beautiful Oceanfront Home in Cudjoe Key has undergone a full renovation and awaits its new owner! All new impact doors and windows, new AC, new flooring throughout and a stunning custom kitchen with granite countertops and stainless steel appliances are a few of the many updates in this amazing renovation .Offering Four generous size bedrooms with Three full bathrooms, it can easily accommodate a large family.The open floor plan of the living and dining room with massive cathedral ceilings , showcase this homes coastal character. Three sliders face the unmatched ocean view , and open to let the ocean breeze flow through the house. Step out on the 500sf covered porch to enjoy the indoor outdoor living and entertaining with breathtaking panoramic Oceanfront views.This spacious Oceanfront four bedroom home is being sold with the adjacent parcel, for a total 13,979 sf lot.and with the Best views in Cudjoe Bay, and plenty of room to add a pool, pool house, and garage, the options are truly endless. Do not miss this great opportunity, this is a one of a kind home. Call now to schedule your private tour.

$3,400,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
3 Bed, 3 Baths, 2,295 SqFt Days Listed: 313
-42.86% ($2,550,000) 18 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Davit Pads25f

Perched on the oceanfront, this extraordinary Cudjoe Key estate boasts breathtaking views from every vantage point, including the rooftop deck. The solid concrete construction, complete with impact-resistant doors and windows, concrete dock, and poolside cabana featuring a bar, sink, and ice machine, ensures a luxurious haven. Lush landscaping, meticulously maintained on a weekly basis, adds to the propertys allure. Upon entering the coded-entry home, a stunning living, dining, and kitchen area unfolds, complete with quartz countertops, stainless steel appliances, and a convenient laundry room. The kitchens center island is spacious and includes refrigerator and freezer drawers, a cooktop and barstools, making it a great entertaining area. The main levels ensuite bedroom, featuring double beds and a jack-and-jill bathroom, offers direct access to the oceanfront patio and a spiral staircase leading down to the pool. Ascend to the master suite, where a lavish bathroom awaits, complete with a jetted tub, double sinks, programmable commode, and walk-in shower, all set against the backdrop of dazzling ocean views. A third ensuite bedroom, features a walk-in shower, single sink, and expansive mirror, with the king-size bed positioned to maximize the stunning vistas. The private outdoor area, complete with a mermaid-adorned pool, large BBQ area, and cabana room, is perfect for outdoor entertaining. World-class fishing and diving opportunities are minutes away, with the Gulf and Atlantic within easy reach. This idyllic location also offers a front-row seat to the marine life of Cudjoe Bay, including porpoise, ospreys, sharks, stingrays, and manatees. Situated in a highly sought-after area of Cudjoe Key, this estate is surrounded by excellent restaurants and boasts wonderful views of the American Shoals Lighthouse.

$3,700,000
Cudjoe Key
Cutthroat Harbor Estates - MM: 23.00
4 Bed, 4 Baths, 3,228 SqFt Days Listed: 309
-0.67% ($25,000) 2 Price Changes : Last Change 17 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges,Othe

BOATERS PARADISE Room for up to 3 BOATS or up to 42ft! with unobstructed sunset views over OPEN water year round on oversized CORNER lot w/water on 2 sides at the very end of a private road offering picture perfect sunsets in a protected bay! Boasting 323 of water frontage, this property includes 175 of open water and 148 of canal frontage featuring a 90 concrete dock at mouth of channel and a private kayak launch. Main level of the home features a wrap-a-round deck, a spacious living area, including a large master bedrm and bathrm with jacuzzi tub, separate shower & his & hers vanities, 2nd bedroom, half bathroom and a chefs kitchen with Sub Zero Fridge. The third level has a private bedroom, bathroom and balcony accessible by a spiral staircase. On the opposite side of the home is a private mother-in-law/teen suite that could be separated and or rented separately with an open floor plan that includes a large living area, 2 Story tongue & groove West Indies Great room w/wet bar and its own updated kitchen with brand new SS appliances overlooking the water! Smart home panels & security cameras thruout. Being sold fully furnished w/exception of a few personal items. Outdoor living including new Giant 16ft Swim Spa w/55 jets, blue tooth ss & fiber optic lights that fits 14 people, outdoor sun TV, pool table, lounge chairs, multiple hammocks & grill. Boat Dockage is super with room for up to 42 ft boat plus a floating Jet Ski Dock that holds 2 Jet Skis! Plenty of parking underneath 12ft concrete pillars for all the guests w/an efficiency for storage as well! Easy access with channel directly in front of home, super fishing spots & reefs! 20 mins to Key West w/plenty of shopping, Nightlife & restaurants. Home was recently tented & has fresh paint, lighting, updated electrical. Home is entirely fenced & Gated w/privacy PVC fencing. The best of all is the wide open water & gorgeous sunset views! Being Sold Turn Key & Seller financing offered at 4% Rate! Owner/Agent

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Most Recent Sales - (55) - Cutthroat Harbor Est as of 2025-04-03
Sale Date Address Sale Price $/SF List Price Sq. Ft. Type Bd/Ba Days Listed
03-12-2025 22994 Anne Bonny $837,000 $706 $849,000 1,184 Single Family 3/2 63
02-28-2025 184 Cutthroat $940,000 $405 $998,000 2,320 Single Family 6/3 201
02-18-2025 22572 Jolly Roger $3,300,000 $1,023 $3,490,000 3,225 Single Family 6/4 347
01-31-2025 22727 Jolly Roger $800,000 $793 $899,000 1,008 Single Family 3/2 166
01-30-2025 191 Doubloon $775,000 $578 $799,000 1,340 Single Family 2/2 46
01-21-2025 124 Yardarm $740,000 $695 $750,000 1,064 Single Family 3/2 37
01-21-2025 22940 Gasparilla $975,000 $665 $1,025,000 1,465 Single Family 2/2 117
11-27-2024 22903 Jolly Roger $685,000 $594 $725,000 1,152 Single Family 3/1 111
11-26-2024 320 Spanish Main $910,000 $861 $949,000 1,056 Single Family 2/2 45
11-14-2024 133 Galleon $1,120,000 $629 $1,275,000 1,780 Single Family 3/2 129
11-14-2024 22532 Jolly Roger $1,600,000 $1,242 $1,775,000 1,288 Single Family 3/2 175
11-14-2024 22766 Jolly Roger $1,800,000 $955 $1,999,000 1,884 Single Family 3/2 120
10-23-2024 1106 Thatch $1,675,000 $657 $1,850,000 2,548 Single Family 4/3 70
09-03-2024 22953 John Silver $777,500 $809 $869,000 960 Single Family 2/2 153
08-12-2024 22974 Anne Bonny $1,085,000 $726 $1,199,000 1,494 Single Family 3/2 1
08-09-2024 139 Le Grand $889,000 $683 $966,000 1,300 Single Family 3/1 61
08-06-2024 1183 De Lussan $1,090,000 $732 $1,090,000 1,488 Single Family 3/2 53
08-02-2024 53 Gold Boullion $695,000 $495 $715,000 1,404 Single Family 3/2 89
07-27-2024 22988 Long Ben $850,000 $710 $899,000 1,196 Single Family 3/2 147
05-31-2024 22842 Buccaneer $890,000 $671 $899,000 1,326 Single Family 3/3 105
05-30-2024 22983 Anne Bonny $1,075,000 $814 $1,175,000 1,320 Single Family 2/2 174
05-06-2024 22464 La Fitte $575,000 $668 $635,000 860 Single Family 2/2 68
05-03-2024 22836 Port Royal $2,000,000 $1,172 $2,100,000 1,706 Single Family 3/2 70
04-30-2024 22977 Long Ben $850,000 $745 $875,000 1,140 Single Family 3/2 48
04-19-2024 1008 Calico Jack $2,150,000 $1,571 $2,699,900 1,368 Single Family 3/2 183
04-17-2024 22684 Jolly Roger $2,450,000 $1,346 $2,495,000 1,819 Single Family 3/2 41
04-12-2024 22922 Blackbeard $731,300 $611 $699,000 1,195 Single Family 3/2 47
03-26-2024 22943 Dirk $1,275,000 $797 $1,409,999 1,598 Single Family 3/2 52
03-22-2024 1172 Coates $1,340,000 $746 $1,375,000 1,794 Single Family 3/2 162
03-15-2024 22856 Jolly Roger $2,575,000 $1,318 $2,695,000 1,953 Single Family 3/2 42
03-12-2024 1077 Picard $1,060,000 $736 $1,099,000 1,440 Single Family 3/2 163
03-11-2024 22910 Privateer $846,000 $881 $870,000 960 Single Family 2/2 98
02-29-2024 53 Treasure Chest $700,000 $648 $725,000 1,080 Single Family 3/2 53
02-02-2024 1078 Picard $1,275,000 $856 $1,330,000 1,488 Single Family 3/2 155
01-19-2024 1124 De Lussan $1,200,000 $854 $1,395,000 1,404 Single Family 3/2 41
12-29-2023 221 Cutthroat $930,000 $880 $950,000 1,056 Single Family 2/2 353
12-29-2023 22656 Puerto Bello $1,375,000 $1,364 $1,375,000 1,008 Single Family 2/2 54
12-28-2023 22939 Gasparilla $1,006,436 $701 $1,149,000 1,434 Single Family 3/2 206
12-18-2023 201 Cutthroat $765,000 $724 $775,000 1,056 Single Family 2/2 102
12-14-2023 154 Cutthroat $800,000 $833 $829,000 960 Single Family 2/2 94
11-29-2023 113 Galleon $1,199,000 $587 $1,199,000 2,042 Single Family 3/3 16
10-30-2023 22808 Privateer $810,000 $557 $859,000 1,454 Single Family 3/2 156
10-02-2023 300 Spanish Main $692,500 $721 $755,000 960 Single Family 2/2 312
09-13-2023 22928 Drake $1,565,000 $735 $1,750,000 2,128 Single Family 3/2 122
08-16-2023 1273 Rogers $5,630,600 $1,876 $5,990,000 3,000 Single Family 4/4 110
08-07-2023 22532 Jolly Roger $1,675,000 $1,300 $1,975,000 1,288 Single Family 3/2 378
07-28-2023 22921 Blackbeard $1,087,000 $823 $1,125,000 1,320 Single Family 3/2 75
07-28-2023 22542 Jolly Roger $1,250,000 $512 $1,400,000 2,440 Single Family 4/3 88
06-16-2023 52 Cutthroat $885,000 $635 $899,000 1,392 Single Family 2/2 85
06-13-2023 172 Galleon $825,000 $669 $850,000 1,232 Single Family 2/2 212
06-12-2023 22973 Anne Bonny $750,000 $756 $799,000 992 Single Family 2/2 68
06-12-2023 22716 Privateer $989,000 $829 $989,000 1,192 Single Family 3/2 50
06-09-2023 340 Spanish Main $975,000 $820 $985,000 1,188 Single Family 3/2 38
04-10-2023 1060 Coxon $835,000 $817 $899,000 1,022 Single Family 2/2 89
04-03-2023 22820 Blackbeard $1,225,000 $862 $1,285,000 1,420 Single Family 3/2 190
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The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 04-03-2025.
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