Cutthroat Harbor Est Properties for Sale in Cudjoe Key, FL

Charming fishing bungalow located on oceanside Cudjoe Key just waiting to be yours. Originally constructed in 1979, 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.

Welcome to this brand-new 3BD/2BA stilted modular home on the Gulfside of Cudjoe Key, just 20 minutes from Key West! Situated on a spacious 6,000 sq. ft. lot, this never-lived-in gem offers an inviting 1,064 sq. ft. open-concept design with soaring ceilings and sunlit interiors from large windows that bring the Florida sunshine indoors.**Enjoy the sleek tile flooring, a modern kitchen with brand-new Whirlpool stainless steel appliances, quartz countertops and the convenience of an included washer and dryer & on demand water heater. Built with durability in mind, the home is equipped with hurricane-rated impact doors and windows & Hardie board siding. The primary bedroom features an ensuite bath with walk-in tile shower and the 2 guest rooms have spacious closets. A screened-in back porch provides the perfect space for relaxing or entertaining.**This property truly shines with its ample outdoor space--plenty of room for a pool, RV, boat, or trailer parking--all surrounded by fencing for added privacy. Youll also appreciate off-street covered parking and a large enclosed storage area. **Cudjoe Key and adjacent Summerland Key offer a laid back Keys lifestyle brimming with local charm and amenities. Savor local dining at renowned spots like The Square Grouper, Broil, The Bent Prop, Galley Grill, Antonios, and Slice of Paradise Pizza. Stock up on groceries at Murrays Market & Summerland Liquors, rent a boat or book a fishing charter, or take care of essentials at the nearby ACE Hardware and post office. This home is a must-see! Dont miss the chance to own your perfect slice of paradise. Schedule a showing today! *Listing Agent is related to the Seller*

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!

Located on a spacious corner lot of a quarter acre in the heart of Cudjoe Key, this home offers both peace and potential. The large, fenced-in yard provides endless opportunities for outdoor activities, with plenty of space for water toys, gardening, or just relaxing in a private, open space. The 25K boat lift makes it an ideal spot for those who love life on the water, while the expansive lot ensures room for all your water-related gear. Upstairs, the home is bright and welcoming, with an abundance of natural light flowing through the open living areas. The kitchen features stainless steel appliances and an island for added prep space. The living room, with its charming stone fireplace, offers a cozy spot to unwind. The primary bedroom is also located upstairs, providing both convenience and privacy. Downstairs, youll find a 1-bedroom guest suite complete with a den and its own fireplace, making it a perfect retreat for guests or family. The propertys design is tailored to the relaxed Florida Keys lifestyle, whether youre hosting gatherings or enjoying the serene surroundings. With ample parking, trailer storage, and just minutes from local shops, this home is the perfect blend of charm, practicality, and potential. Its a great spot to enjoy island living and all the Florida Keys have to offer!

Idyllic Canal-Front Cudjoe Key retreat on a generous fenced-in lot in a prime location! This bright and spacious Cutthroat Harbor Estates home boasts an open concept main living space and three generous bedrooms! Coming soon, the seller is replacing the existing roof with a new metal roof. Upon entry, this turnkey home is tailor-made for entertaining. The living room flows seamlessly with a well-appointed dining room and kitchen, complete with stainless steel appliances, abundant white cabinetry and prep space, and peninsula with counter seating. For year-round indoor-outdoor entertaining, a sprawling screened-in veranda, located just off of the dining room, offers an ideal backdrop for grilling while enjoying serene Canal Views. Two well-equipped guest bedrooms offer plenty of space for a growing family or visitors, while the primary suite comes relaxation-ready with large closet and convenient en suite bathroom. Downstairs, a large covered carport allows for shaded parking and waterside entertaining. Sixty feet of concrete dockage allow for easy and frequent boating, enjoy world class diving and fishing within minutes from this ideal location! Rinse off after a long day on the water in the convenient outdoor shower, or unwind in the relaxing hot tub, your coveted Florida Keys lifestyle awaits! Plenty of open and covered parking on this oversized, fenced-in corner lot with room to spare for trailer or RV parking. Nestled within a quiet, established neighborhood but just minutes to delectable dining and shops in town!

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!

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!

Welcome to 184 Cutthroat Drive, a wonderful income producing waterfront home on the peaceful Cudjoe Key. This home offers a spacious open floor plan with lots of natural light.Main Level (Upstairs):4 bedrooms, split for plenty of privacy2 full bathroomsLarge living, dining area, and kitchen with an open layout and tons of counter space and cabinets, and stainless steel appliances.Large deck for relaxing and star gazing on clear nights.All new impact windows and doors on upper level.New AC 2020Lower Level (Legal Pre-FIRM Downstairs):2 additional bedrooms1 full bathroomSeparate living space, ideal for guests or extended familyDirect outdoor access for easy enjoyment of the waterfront. Separate set of washer and dryer for downstairs. Outdoor Features:Private canal frontage with quick access to open waterPartial fenced in front areaNew roof 2017New 10,000lb boat lift, and new composite dock.Ample storage for your water sports and fishing gearThis home is a great opportunity for those looking for a property to enjoy the natural beauty and recreational opportunities of the Florida Keys and large enough to bring all their friends and family along with them! With its prime location and in walking distance to the Square Grouper one of the best restaurant in the Keys, 184 Cutthroat Drive is a true gem!

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, 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.....

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

Welcome to Cayo Casa Cudjoe, a tropical haven where the island lifestyle seamlessly blends with world-class fishing. Nestled on a beautifully landscaped triple lot, this waterfront gem offers the ultimate escape. The heart of this anglers paradise are the 2 covered boat slips, each equipped with their own lift; your gateway to the best fishing, diving and boating in the Florida Keys. Whether youre setting out for an early morning catch or cruising the calm waters at sunset, these private boat slips make every adventure effortless. The elevated main house features 2 bedrooms and 2 baths, with soaring vaulted ceilings and warm original wood flooring that bring a natural island feel to your living space. The open-concept great room is perfect for entertaining or unwinding after a day on the water, with stunning canal views just beyond your windows. Below, the pre-firm guest quarters provide a comfortable and private retreat for visitors, or the perfect spot to relax after a day spent fishing, diving, or exploring the nearby islands. With 18,564 sq ft of land, youll have room to spread out, add a pool or just fully embrace an abundance of privacy. Whether its hosting outdoor gatherings, parking your boat trailers and RVs, or simply soaking in the lush surroundings, Cayo Casa Cudjoe is designed to maximize your enjoyment of this beautiful tropical setting. Dont miss the chance to call this island retreat your own and experience the best of Florida Keys has to offer!

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!

Breathtaking Open Water Home in Cudjoe Key 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

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.

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.

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.

A luxury waterfront estate with panoramic ocean views, this walled and gated masterpiece surrounded by gorgeous landscaping provides utmost privacy and the perfect Keys lifestyle and comes completely furnished. The unique 6-bedroom, 4-bathroom layout offers ample space for family and guests with breathtaking ocean vistas from almost every room. A secluded backyard oasis features a private beach, a sparkling heated pool and spa and a charming tiki hut for entertaining and ideally situated for breathtaking sunsets with 140 of waterfront for Keys living at its best. Across the breezeway, the master suite aka The Sanctuary provides total privacy from the main house. Wake up to ocean views provided by floor to ceiling windows from your king size bed or while soaking in the stand-alone porcelain tub in the beautiful master bathroom. A coffee & liquor bar, ice machine, & beverage cooler makes this master suite an escape for total relaxation. Enjoy effortless boating to the ocean or the gulf side for all your fishing and diving adventures. A fish cleaning table is conveniently located right on the dock. All updates and furnishings were done by DAsign Source. This house is a must see so schedule your private tour today.

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

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.