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22410 Jolly Roger Dr, Cudjoe
$1,500,000
2 Beds ⋅ 2 Baths ⋅ 620456 MLS
Welcome to your oceanfront retreat on Cudjoe Key, where panoramic wide open ocean views, exceptional outdoor living, and easy boating access come together to create the quintessential Florida Keys lifestyle. Built on a lot and a half with durable CBS construction, this inviting 2-bedroom, 2-bath, 1,587 sq. ft. home is perfectly positioned to take advantage of its spectacular waterfront setting. The light-filled interior flows effortlessly into the spacious screened porch where you'll enjoy ocean breezes, morning coffee, waterfront dining and unforgettable sunrises and moonlit evenings. Just beyond, an expansive deck provides even more space for entertaining or simply relaxing while overlooking the endless blue waters. Inside, the primary suite serves as a peaceful waterfront sanctuary, featuring a private en-suite bath, walk-in closet, and sliding glass doors that open directly to the deck, allowing you to wake up to breathtaking ocean views each morning. A comfortable guest bedroom offers welcoming accommodations for family and friends. Boaters will appreciate the dock and davits, providing convenient access to the Atlantic for world-class fishing, diving, sandbar adventures and sunset cruises. The lower-level enclosure offers abundant storage for kayaks, paddleboards, fishing gear, and all of your island essentials. Whether you're entertaining guests on the spacious outdoor living areas, heading out for a day on the water, or simply soaking in the tranquil open water views, this Cudjoe Key waterfront home is your opportunity to embrace the relaxed, waterfront lifestyle the Florida Keys are known for.

22410 Jolly Roger Dr, Cudjoe
1113 De Lussan Ln, Cudjoe
$1,460,000
2 Beds ⋅ 2 Baths ⋅ 620497 MLS
Breathtaking Open Water Home in Cudjoe Key - Comes FULLY FURNISHED! Welcome to paradise! This stunning 2-bedroom, 2-bath home captures magnificent open water views and embodies the ultimate Florida Keys lifestyle. Main Living Area: Step inside to an open-concept kitchen, living room, and dining area bathed in natural light. Every detail is designed to highlight the beauty of the surrounding water and create a seamless flow between indoor comfort and outdoor serenity. A full bath on this level adds convenience for you and your guests. Private Master Retreat: Upstairs, your private master suite offers sweeping panoramic water views — the perfect place to wake up to the gentle sound of the waves and breathtaking sunrises, plenty of space for office or sitting area Outdoor Living at Its Best: A full wrap-around porch invites you to relax, unwind, and soak in the endless open water views and refreshing ocean breeze. Whether you're entertaining friends or enjoying a quiet morning coffee, this outdoor space is the heart of coastal living. Prime Waterfront Location: Situated in a highly desirable area with easy access to open water, this home is ideal for boating, fishing, or simply savoring the natural beauty of the Keys. Features include a boat ramp for effortless launching, 50AMP RV service, and room to park a Class A motorhome. Comes with six exterior security cameras, with capacity to add up to ten more for peace of mind. Don't miss your opportunity to own this true open water gem — a perfect blend of comfort, style, and the unmatched tranquility of the Florida Keys.

1113 De Lussan Ln, Cudjoe
22872 Buccaneer Ln, Cudjoe
$1,449,000
3 Beds ⋅ 3 Baths ⋅ 620481 MLS
*SWIMMING POOL BEING BUILT NOW! Construction process underway. * 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. Or stay on the screened in covered porch and enjoy the Keys breeze! The roughly 1100 sqft garage/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, you'll 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. Don't miss the opportunity to make it yours--schedule your private showing today! Seller is licensed FL real estate agent.

22872 Buccaneer Ln, Cudjoe
142 Peg Leg Ln, Cudjoe
$1,400,000
4 Beds ⋅ 3 Baths ⋅ 615839 MLS
Welcome to your dream coastal retreat! Perched on concrete stilts with sweeping views, this newer 4-bedroom, 3-bath luxury home offers the perfect blend of island elegance and modern comfort. Two spacious master suites provide privacy and flexibility, while the open-concept living space is framed by wide, breezy balconies -- ideal for soaking in the sunrise or entertaining guests in true Keys style. Canal with direct access to the open ocean -- no bridges, no hassle, just minutes to the Atlantic or Gulf. Inside, enjoy high-end finishes, plenty of natural light, and a layout designed for both relaxing and hosting. Whether you're seeking a full-time residence, vacation getaway, or income-producing investment, this waterfront gem checks every box. 15,000 LB Boat Lift Permit Application submitted and being processed.

142 Peg Leg Ln, Cudjoe
22737 Blackbeard Ln, Cudjoe
$1,080,000
3 Beds ⋅ 2 Baths ⋅ 616428 MLS
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 298 sq. ft. of enclosed storage space. Schedule your private showing today! One of the Sellers is a Licensed FL Real Estate Sales Associate.

22737 Blackbeard Ln, Cudjoe
110 Doubloon Ln, Cudjoe
$1,075,000
2 Beds ⋅ 2 Baths ⋅ 619225 MLS
Welcome to island life--this charming 2-bedroom, 2-bath waterfront cottage captures everything we love about the Florida Keys. Tucked on a desirable corner lot with canals on two sides, the property offers exceptional privacy, sea breezes, and inviting views from multiple vantage points. Inside, the home is bright, fresh, and thoughtfully updated, featuring a crisp white kitchen with quartz countertops, stainless steel appliances, and an easy flow into the main living space--perfect for relaxed coastal living or entertaining. The primary suite offers a peaceful retreat with a soaking tub and a walk-in tile shower. Step outside and the lifestyle truly comes to life. Covered porches and a poolside patio invite you to unwind in the shade, while the tiki hut and private pool create an island escape. The spacious, fenced yard offers room to spread out. Boaters will appreciate the easy ocean-side access, putting world-class fishing, diving, snorkeling, and the stunning backcountry beaches right at your fingertips. Well-maintained and move-in ready, this home is ideal as a full-time residence, vacation getaway, or investment opportunity. Located on Cudjoe Key, just 30 minutes from both Key West and Marathon, you're perfectly positioned to enjoy the best of the Lower Keys while still being close to dining, shopping, and adventure.

110 Doubloon Ln, Cudjoe
165 Cutlass Ln, Cudjoe
$1,000,000
4 Beds ⋅ 3 Baths ⋅ 620895 MLS
Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous kitchen and dining area serve as the heart of the home--ideal for hosting gatherings after a day on the water. Updated bathrooms offer a modern feel, while the spacious primary suite provides a private sanctuary to unwind. Outside, the property offers ample off-street parking and room to add a pool, creating the perfect setting for outdoor living. A versatile 299 sq. ft. downstairs enclosure adds valuable storage space for fishing gear, water toys, and more. With direct boating access to both the Gulf and the Atlantic, adventure is always within reach. Plus, local restaurants, marinas, and island bars are just a short walk away, letting you enjoy the best of the Keys lifestyle. At just $439 per square foot, this property represents the lowest price per square foot for a waterfront home currently available in the Florida Keys, making it one of the best opportunities on the market today. Bring your boat and start living the Florida Keys dream.

165 Cutlass Ln, Cudjoe
22748 Blackbeard Ln, Cudjoe
$955,000
2 Beds ⋅ 2 Baths ⋅ 620919 MLS
Motivated Seller! Welcome home to this impressively spacious 2-bedroom, 2-bath Keys retreat, offering an elevated blend of comfort, functionality, and coastal living. The outdoor space is a dream with an in-ground concrete saltwater pool (2021) with a waterfall feature, 12k lb boat lift (2021), 60' concrete seawall, & an expansive 10' deep back porch (nearly 700 sq ft of porches), all perfect for outdoor dining, lounging, & savoring tropical breezes year-round. This home is a dream for boaters with quick access to open water, favorite sandbars, and world class fishing & diving. Inside, you'll find upgraded stainless steel appliances, onyx granite waterfall counters, a cedar closet in the primary suite plus a walk-in closet plus add'l double closet & linen cabinet, with beautiful slate flooring throughout, adding modern elegance to the easy living layout. Additional features include a 30 amp RV plug, plantation shutters throughout, Miami-Dade rated accordion shutters, a hip metal roof, excellent insurance rates, plus transferable flood insurance ($570!) for added savings. The nearly 700 sq ft permitted ground level offers an extra-large storage area, workshop, or game room, with plenty of space for an outdoor kitchen & lots of covered parking, while tropical landscaping welcomes you home. With thoughtful upgrades throughout & nearly new amenities in place, this home is waiting for you to enjoy the incredible Florida Keys lifestyle.

22748 Blackbeard Ln, Cudjoe
22811 Buccaneer Ln, Cudjoe
$920,000
3 Beds ⋅ 2 Baths ⋅ 620769 MLS
Looking for a move-in-ready waterfront home with concrete block construction and quick boating access? This beautifully updated Cudjoe Key retreat checks all the boxes! Tucked away on the south side of the neighborhood, you'll be just minutes from open water while enjoying a peaceful setting away from the noise of US-1. At the same time, you'll still be close to Lower Keys favorites like Square Grouper, Morning Joint, and Kiki's Sandbar. Designed for easy & enjoyable island living, this fully furnished, turn-key home has been thoughtfully renovated from top to bottom. Hurricane impact-rated windows, doors, and metal roof provide peace of mind, while the bright, open floor plan welcomes abundant natural light and tropical surroundings. The spacious open living, dining, and kitchen areas flow seamlessly together, creating a comfortable, functional space for everyday living or entertaining. The updated kitchen and bathrooms feature quartz and butcher block countertops, while the bathrooms showcase beautifully tiled walk-in showers, and durable LVP flooring extends throughout the home. My personal favorite is the oversized screened porch just off the kitchen and dining area. With its brand-new roof and fully screened design, it's the perfect spot for morning coffee, afternoon naps, or winding down after a day on the water. Boaters will appreciate the quick access to deep water, a concrete seawall, and a new elevator boat lift. Downstairs, you'll find covered parking, a spacious storage enclosure, a concrete slab, brand-new composite decking, and plenty of room for your RV, boat trailer, and all the gear that comes with the Keys lifestyle.

22811 Buccaneer Ln, Cudjoe
22954 Buccaneer Ln, Cudjoe
$920,000
3 Beds ⋅ 2 Baths ⋅ 616110 MLS
Welcome to 22954 Buccaneer Ln, a quintessential Florida Keys waterfront escape. Perfectly positioned on a rare corner canal lot, this property offers 191 feet of concrete dockage with quick, unobstructed access to open water—ideal for serious boaters. The exterior's inviting Keys-style cedar siding blends seamlessly with lush tropical landscaping, creating a relaxed island vibe from the moment you arrive. Inside, the home offers a warm and inviting atmosphere with rich wood floors, an open-concept layout, and expansive windows that frame serene water views. The chef's kitchen is well-equipped with stainless steel appliances, generous counter space, and a cozy breakfast nook. The spacious screened porch overlooking the water is perfect for entertaining or simply unwinding with a drink in hand as the sun dips below the horizon. The primary suite is notably large, offering privacy and comfort, while two additional bedrooms provide flexibility for guests or office space. Downstairs, abundant storage accommodates all your water toys, fishing gear, and adventure essentials. Unique touches, like a fenced area for a pet tortoise and an outdoor shower, enhance the property's character. Whether as a full-time residence, seasonal getaway, or investment, this home delivers the ultimate in Keys living.

22954 Buccaneer Ln, Cudjoe
151 Cutthroat Dr, Cudjoe
$910,000
2 Beds ⋅ 3 Baths ⋅ 617765 MLS
Move-in ready waterfront 2-bedroom, 2.5-bath home located in desirable Cudjoe Key. The open floor plan features a spacious living and dining area complemented by an upgraded kitchen with new cabinetry, granite countertops, and modern stainless-steel appliances. The main level offers two bedrooms and 1.5 baths, while a permitted full second bath is conveniently located downstairs with easy access to the pool. Situated on a fenced corner lot, the property includes off-street parking, an in-ground pool with a concrete pool deck, and lush tropical landscaping. There is ample space for boat and trailer parking, plus room for an RV with 30-amp service. Enjoy oceanside boating with a concrete seawall, 6,000 lb. boat lift, and plenty of watercraft parking. Cudjoe Key offers access to fine dining and is less than 30 minutes from Key West or Big Pine Key, providing additional shopping, restaurants, beaches, and parks. Additional features to this property include but not limited to newer roof (2018), brick paver driveway, New central A/C (2025), large storage and impact windows and doors.

151 Cutthroat Dr, Cudjoe
288 Spanish Main Dr, Cudjoe
$860,000
3 Beds ⋅ 2 Baths ⋅ 619124 MLS
MAJOR PRICE IMPROVEMENT -- AN EXCEPTIONAL VALUE FOR A BEAUTIFULLY UPDATED CUDJOE KEY CANAL-FRONT HOME! This updated 3-bedroom, 2-bath canal-front home on Cudjoe Key offers approximately 60 feet of concrete dockage directly behind the property, with plenty of room for your boat and convenient access to Gulf and Atlantic waters for fishing, diving, sandbar trips, and cruising the Lower Keys. The bright, move-in-ready interior features an updated kitchen with quartz countertops, stainless-steel appliances, abundant cabinet space, and an oversized 8-foot island that opens to the main living area. Both bathrooms have been updated with attractive tile finishes, giving the home a clean and modern feel throughout. Additional features include a 2018 metal roof, newer high-efficiency windows, updated HVAC, main-level laundry, and 30-amp RV service for added flexibility. The elevated design provides covered parking and useful downstairs storage, while the covered outdoor areas offer space to relax and enjoy the Keys lifestyle. This home is well-suited for a primary residence, second home, or waterfront getaway. Insurance information and elevation documentation can be provided for buyer review. A VA loan assumption may be available to qualified buyers, subject to lender and VA approval. Seller welcomes serious offers and will consider reasonable terms with an acceptable contract. Bring your offer and your boat!

288 Spanish Main Dr, Cudjoe
131 Doubloon Ln, Cudjoe
$840,207
3 Beds ⋅ 2 Baths ⋅ 617960 MLS
3BR/2BA waterfront home on Doubloon Lane offering classic Florida Keys living and relaxation. Features include a pool, large covered patio, sun deck, and a 10,000-lb boat lift, ideal for boating and outdoor enjoyment. Upstairs living area includes impact windows and a new hot water heater (2024). The downstairs area includes two large storage rooms, one of which features a fully functioning bathroom with shower (additional bathroom not reflected in public records). The property provides ample parking for vehicles, trailers, and recreational equipment and is designed for relaxed indoor-outdoor living with convenient water access.

131 Doubloon Ln, Cudjoe
154 Cutthroat Dr, Cudjoe
$835,000
2 Beds ⋅ 2 Baths ⋅ 618809 MLS
VA Assumable Loan for qualified buyers using VA benefits! Details available at buyer's request. Beautifully updated 2 bedroom, 2 bathroom home with spacious covered, screened porch overlooking the canal with access to both the Gulf of Mexico and the Atlantic Ocean in just a few minutes. With pride of ownership, this house has been upgraded and well maintained. Many upgrades include: 2024 - New fence with double gates and an entrance gate, gutters, landscaping, tile flooring, freshly painted interior and new vanities and mirrors. 2020: - New A/C and Granite countertops. 2021 - New hot water heater. 2018 - New metal roof, impact windows and Hardie-plank concrete siding. Large primary suite with large closet, full size tub and new vanity/mirror. Spacious guest bedroom with large closet and lots of light! Guest bathroom has full tub with new vanity and mirror. Kitchen is well equipped with Whirlpool stainless appliances, granite countertops, large kitchen island and dedicated dining room. Open concept living with access to the covered, screened porch from both the dining room and family rooms. Fully fenced yard, 504sf storage downstairs, beautifully landscaped, room for RV's, boats, trailers and your outdoor toys! Walking distance to restaurants, bars, convenience stores, shopping and just 19 miles to Key West! Come take a look and make Cudjoe Key and the Florida Keys your new home. Low Insurances: $595 flood (assumable), $1004 homeowners and wind $5284

154 Cutthroat Dr, Cudjoe
153 Peg Leg Ln, Cudjoe
$830,000
3 Beds ⋅ 2 Baths ⋅ 618377 MLS
Super quick ocean access and 60' of concrete dockage from this 3 Bedroom 2 Bath canal front home located just 2 canals over from open water! Plenty of room for all your toys in the oversized 2-Car Garage with overhead doors on both sides. Inside you will find an open floor plan leading out to a full-length Porch overlooking the water for morning coffee or evening cocktails with family and friends. The spacious Kitchen offers stainless appliances and center island with seating. Porch access is enjoyed from the Primary Suite and Guest Bedroom. Plenty of room to entertain outside on the covered lanai or in the large yard where you will find lots of fruit trees including papaya, key lime, avocado and banana. Metal roof and lots of tropical landscaping complete this Florida Keys home.

153 Peg Leg Ln, Cudjoe
22948 Drake Ln, Cudjoe
$600,000
617328 MLS
Boater/Angler special: 70-foot concrete seawall features hard-to-find boat slip/basin, plus 10,000-pound boat lift . This canal front-vacant lot is ROGO exempt and ready to build on. It corners Drake Lane's dead end and is second from Cudjoe Bay's open water. Perfect location for new build. Previous house removed and lot is ready for your vision. Electric was in place, buyer to verify FKAA sewer/septic tank system. Arborist cleaned lot and cleared boat basin.

22948 Drake Ln, Cudjoe
248 Yardarm Rd, Cudjoe
$320,000
2 Beds ⋅ 2 Baths ⋅ 618882 MLS
This property is above the flood zone so it can be rebuilt, with some restrictions. It does not fall into the Monroe County 50% rule.

248 Yardarm Rd, Cudjoe
Vacant Vacant Picard Lane, Cudjoe
$175,000
615956 MLS
Waterfront vacant lot waiting for you: Build your dream home here! Located in the highly desirable Cutthroat Harbor Estates neighborhood. This is a fantastic opportunity: apply for your permits to build your dream home, and complete it with a boat dock to enjoy the Florida Keys Lifestyle. This property is situated on a quiet street with only 2 homes to pass by, and you're boat will be in the open water. It's off the beaten path yet conveniently close to local businesses and excellent restaurants. You'll have an easy drive to Big Pine, Marathon, or Key West. Make your plans—this could be the perfect spot you've been searching for!

Vacant Vacant Picard Lane, Cudjoe
Lot 13 John Silver, Cudjoe
$160,000
620658 MLS
Waterfront opportunity in desirable Cutthroat Harbor Estates. This Tier 3 canal-front lot offers quick water access and a peaceful island setting. The property may be entered into Monroe County's ROGO system, or a transferable building right may be obtained, offering the potential to bring your Florida Keys vision to life.

Lot 13 John Silver, Cudjoe