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20844 W 4th Ave, Cudjoe
$2,675,000
4 Beds ⋅ 3 Baths ⋅ 619299 MLS
FISHERMAN'S DREAM! BIG BOATS WELCOME! DEEP WATER! LARGE WATERFRONT HOME in the prestigious neighborhood of Cudjoe Gardens. When you first walk up you will notice the beautiful landscaping, tropical fruit trees, key limes, mangoes, lemons, bananas and avocados! This stunning and elegant concrete residence on elevated lot, offers the perfect harmony of luxury and comfort. All new impact windows & doors, framed by custom plantation shutters. Every space has been meticulously curated, brand-new AC, and more! This incredible property with almost 3,000sf offers an open and spacious floor plan. The living area blends seamlessly with the screened in lanai with full bar, concrete heated, saltwater pool and overflow hot tub, offering full sun during the day. Leave the full wall of glass doors open to allow the fresh breeze of the Florida Keys as well as the gentle sound of the pool's waterfall. The Custom Chef's Kitchen has top of the line Stainless Steel Appliances, new wine cooler, Granite Countertops, huge island, and Custom Cabinetry. The home has a large master bedroom suite with its own living room/office/exercise area, sliders to back yard, 2 closets, and wonderful bathroom with spa like shower. 2 large guest bedrooms with full bath, an incredible Mother In Law/Guest Suite set up as bedroom sleeping 4-8 people with living area, with it's own driveway and private entrance and access to lanai, gorgeous bamboo flooring with inlayed Compass Rose and ceiling made of river recovered heart cypress, walk in closet designed as storm shelter, and full bath. Other features, outdoor kitchen and bar, 1 car garage with ample storage, double boat lift 20,000lb, 5 ft draft, 2 Ace 5,500lb davits, 100x10 concrete dock, Killer Dock brand fish cleaning station, commercial ice maker, and 5 min. Ride from the Ocean or Gulf, Fuel, Marina, and Tackle store, perfect for the avid fisherman. Wide canal, flow thru canal. This property is a boat lover, fisherman, and chef's Dream Home

20844 W 4th Ave, Cudjoe
653 Sawyer Dr, Cudjoe
$2,500,000
3 Beds ⋅ 2 Baths ⋅ 620288 MLS
Welcome to Cudjoe Gardens and get 2 for 1!!! Two Lots giving you the very BEST situation, offering A Beautiful home with unobstructed Stunning Open Water Views and a private beach and a 2nd lot with tiki and boat lift on a canal with deep water for bigger boats. Your lift and boat never block your views! This home is simply gorgeous and has it All!! You will feel like you landed at a private resort and never want to leave! 3 bedrooms, split floor plan, sunroom for relaxing and taking in the views, open floor plan for the amazing kitchen and living area. Downstairs you can decide if you want to watch tv in the screened in outdoor living area and enjoy the outdoor kitchen or sit under the tiki hut, or sun bath on your own beach. Whatever you chose, this property is a Dream come true and you will never want to leave home!

653 Sawyer Dr, Cudjoe
23087 Sailfish Ln, Cudjoe
$1,800,000
3 Beds ⋅ 4 Baths ⋅ 618494 MLS
Designed for those who live by the tides, this extraordinary waterfront residence captures everything that defines the Florida Keys lifestyle. Situated on a rare 15,625 sq ft double lot with 175 feet of deep-water dockage, the home enjoys a premier location one in from open water, delivering sweeping open water views while remaining protected within a wide 50-foot canal. Architecturally striking, the Keys Cottage-style home features an elevated design, metal roof, wraparound outdoor spaces, and an abundance of natural light. Inside, the expansive Great Room impresses with soaring 13'+ ceilings, generous gathering areas, and seamless flow to outdoor living spaces overlooking the water. The kitchen is both functional and welcoming, equipped with a gas range, extensive cabinetry, oversized counters, pantry, and dumbwaiter, making entertaining effortless. The upper level is a true retreat — the entire second floor is devoted to the primary suite, complete with stunning open water views and a private veranda. A second balcony offers a unique vantage point for watching nighttime rocket launches across the horizon. Outdoors, the property becomes a private tropical compound, featuring a fenced yard, hot tub, mature palms, and fruit trees including mango, guava, fig, and cherry. A brick-paved driveway leads to a two-car garage with interior access, completing this exceptional offering.

23087 Sailfish Ln, Cudjoe
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
20841 W 8th Ave, Cudjoe
$1,400,000
3 Beds ⋅ 2 Baths ⋅ 616914 MLS
Meticulously maintained and located in the desirable boating community of Cudjoe Gardens, this nearly 1,900 sq ft home includes 90 feet of dockage, a 10,000 lb boat lift, hurricane impact windows, doors, and garage door, as well as a gorgeous pool creating your own private oasis. A boater's paradise with easy access to both ocean side and gulf side! The inside boasts 3 spacious bedrooms and an open kitchen/living room floor plan. Whether you're enjoying a morning cup of coffee on the spacious front porch, catching some sun on the outdoor poolside patio, or relaxing in the screened in porch, this home truly offers endless leisure. It also comes with the convenience of being down the street from the amazing Bent Prop restaurant and Cudjoe Gardens Marina!

20841 W 8th Ave, 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
20838 W 5th Ave, Cudjoe
$1,300,000
3 Beds ⋅ 2 Baths ⋅ 617081 MLS
Discover the ultimate boating lifestyle in the Florida Keys with this beautiful Deep Draft Canal Front Pool Home in the exclusive waterfront enclave of Cudjoe Gardens. Set on an expansive 11,000 sq ft lot with 100 feet of waterfront, this ground-level, above-flood concrete ranch home offers seamless access to the Pool and water. Inside, enjoy nearly 2,000 square feet of living space with 3 Bedrooms and 2 Bathrooms, soaring pine ceilings, and a sun-filled Florida room overlooking the canal. The layout is open and bright, perfect for entertaining or quiet relaxation. Step outside to your private 60' dock with a 10,000 lb boat lift, nestled on a crystal-clear 50' wide deep-draft canal — ideal for serious boaters. After a day on the water, unwind in the expansive screened-in pool area, perfect for enjoying the Keys' tropical lifestyle year-round. Cudjoe Gardens is a true gem — a concrete home community where most properties are built above flood and have no stairs to climb. The neighborhood Cudjoe Gardens Marina offers fuel, a boat ramp, bait, and refreshments, and is adjacent to the waterfront Bent Prop restaurant, all just a short walk away. This is more than a home — it's a launchpad for your next great adventure.

20838 W 5th Ave, Cudjoe
22874 Bluegill Ln, Cudjoe
$1,100,000
3 Beds ⋅ 3 Baths ⋅ 619181 MLS
Prestigious ''Cudjoe Ocean Shores'' home with quick, deep boating access to both the Atlantic and the Gulf. 85 feet of concrete dock with heavy duty davits and a large step-down water entrance for your backyard swimming and boating pleasure. This immaculate 3 bedroom, 3 bath home comes with a 10,200 Square Foot Lot, New Kitchen with Stainless Appliances, New Full Bath, Impact Windows and Doors, Metal Roof, Lush Landscaping, Haden Mango Tree, Royal Poinciana Tree and plenty of room for a pool! The home also comes with a unique downstairs private one bedroom, one bath suite for extra family and friends. This sought after Cudjoe Ocean Shores neighborhood is conveniently located just minutes from Key West. This home is easy and fun to show! Don't miss this one!!!

22874 Bluegill 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
21855 Spain Blvd, Cudjoe
$1,075,000
3 Beds ⋅ 2 Baths ⋅ 618820 MLS
Imagine owning a pool home and 3.3 private acres in the Florida Keys - this rare opportunity is in Cudjoe Acres, an equestrian area just 20 miles from Key West, with two equestrian facilities just around the corner. The home sits on one secluded acre surrounded by a botanical garden of impressive plantings including rare palm trees, buttonwoods, orchids, dragon fruit cactus, fragrant Joe wood, a Valencia Pride Mango tree. The custom-built, 1467 sq. ft., 3-bedroom, 2-bath CBS/frame home offers island charm with pineapple railings and multiple porches. An expansive open area below the home provides options to enclose for storage, use for covered parking, sitting areas and poolside entertaining. 21855 Spain Blvd. (the home) is offered with 21865 Spain Blvd. which is comprised of two adjacent parcels (W & V) that ensure seclusion and privacy; Parcel V has two gates that open to a road on east side. The 3.3 acres offer exceptional trees, a couple of natural ponds, a chicken coop, shed, covered pole structure, two cisterns, and more. One would never guess that it's possible to be this close to excellent local restaurants, an international airport and the arts and culture of Key West.... yet feel as if you're truly away from it all.

21855 Spain Blvd, 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
21082 6th Ave, Cudjoe
$925,000
617437 MLS
An exceptional opportunity awaits in one of the Lower Keys' most desirable neighborhoods. This oversized corner lot is ROGO exempt and comes with approved building plans already on file with Monroe County, allowing you to skip the waiting line and begin building your dream home immediately. The existing structure has been demolished, clearing the way for a seamless transition from vision to reality. Set on a spacious corner canal parcel, the property boasts approximately 280 feet of water frontage, providing panoramic canal views and generous dockage potential. A brand-new 17,000 lb. boat lift is already installed, ready for your vessel. With deep-draft oceanside access just moments away, this location is ideal for boating enthusiasts who need quick and easy access to open water. Cudjoe Gardens is one of the few neighborhoods in the Lower Keys offering a full-service marina, a public boat ramp, and the locally loved Bent Prop restaurant, all within the community. Whether you're ready to build your full-time residence or a seasonal escape, this property offers a rare chance to create a custom home in a prime waterfront setting without the long ROGO wait.

21082 6th Ave, 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
21073 7th Ave, Cudjoe
$900,000
3 Beds ⋅ 2 Baths ⋅ 620492 MLS
Florida Keys Waterfront Paradise - 80' Dock & No Bridges to Open Water! Nestled in a boater's paradise, this 2,198 sq. ft. 3-bed, 2-bath home offers a split floor plan for privacy and comfort. Inside, the spacious kitchen boasts stainless steel appliances, generous cabinet space, and ample corian counter space perfect for cooking up your fresh catch. The open-concept living and dining area flows effortlessly to four sets of French doors, leading to a large screened patio ideal for seamless indoor-outdoor living. A large utility room adds extra convenience. With 80 feet of canal frontage and no bridges to open water, you're just minutes from incredible destinations like American Shoal, Looe Key, and Marvin Key. Spend your days snorkeling, fishing, or exploring pristine islands, then unwind with unforgettable dining experiences at fantastic nearby restaurants. Whether you're an angler, adventurer, or just seeking the perfect Keys retreat, this home is your gateway to paradise.

21073 7th Ave, Cudjoe
22953 John Silver Ln, Cudjoe
$900,000
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
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
22961 John Avery Ln, Cudjoe
$850,000
2 Beds ⋅ 2 Baths ⋅ 619710 MLS
Reduced over 100k for a quick sale! Boater's Paradise in Cudjoe Key under 1 million! Bring your boat, jet skis, and sense of adventure! This upgraded two-story coastal retreat is designed for water lovers, featuring over 60 feet of dock space complete with shore power, plumbing, and brand-new dual jet ski davits plus a boat lift -- perfect for launching into the Florida Keys lifestyle. The lower level offers a bonus unit, storage and covered porch. Upstairs, the main residence features a bright, open-concept living space with large impact-resistant windows and doors installed by the previous owners, offering both natural light and storm protection. The home is energy-efficient and move-in ready. Located in a quiet and highly desirable neighborhood in Cudjoe Key, this fully furnished gem is a rare opportunity to own a true Keys boater's dream home. Whether you're an avid fisherman or just looking for the ultimate waterfront lifestyle, this property is a must-see!

22961 John Avery Ln, 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
701 Spanish Main Dr Unit 512, Cudjoe
$840,000
2 Beds ⋅ 2 Baths ⋅ 617604 MLS
VACATION RENTAL OPPORTUNITY - OPEN WATER VIEWS + 43' DOCK - 2BR/2BA | 864 SQ. FT. Beautifully maintained 2-bedroom, 2-bath waterfront home offering open water views and excellent rental potential. This 864 sq. ft. property features a 43-foot dock with quick access to world-class boating, fishing, and diving in the Florida Keys. Ideal for investors or owners seeking a turn-key vacation rental property. PROPERTY FEATURES: • 864 sq. ft., efficient and well-designed floor plan • 2 Bedrooms / 2 Full Bathrooms • Open water views from the living area and outdoor spaces • 43' dock suitable for larger vessels • New hot water heater • Stainless steel appliances in updated kitchen • Protection from north winds for comfortable year-round outdoor enjoyment • Open-concept living/dining area ideal for guest appeal • Strong rental history potential in a desirable waterfront community Located minutes from top Keys attractions, marinas, and dining, this home offers excellent guest appeal and easy access to the best of island living. Perfect for buyers seeking a high-performing vacation rental or a personal getaway with income potential. Turn-key, income-ready, and perfectly positioned for the ultimate Keys lifestyle.

701 Spanish Main Dr Unit 512, Cudjoe
701 Spanish Main Dr Unit 51, Cudjoe
$837,000
2 Beds ⋅ 2 Baths ⋅ 620128 MLS
Panoramic Ocean Views W/ Transient Rental License! This beautifully updated and well-maintained stilt home offers 2 bedrooms and 2 bathrooms, large kitchen with all the necessities, panoramic ocean views, a private 35' concrete seawall for your boat and off street parking for your vehicle. This home has an open deck overlooking the crystal clear waters and a screened deck just waiting for you to come and relax. Perfect for the fishing enthusiasts, enjoy quick boating access to the Atlantic Ocean and Gulf of America. Boat, swim, snorkel or dive in the beautiful Florida Keys right from your 35-foot seawall, plus the added bonus of all that Venture Out gated community has to offer. Venture Out has 4 miles of paved secured streets to walk or bike. Amenities include oceanfront heated saltwater pool, jacuzzi, marina with fuel dock, boat launch, convenient store, tennis, pickleball, bocce, basketball, playground, fun activities and more! Close to restaurants, shopping, parks and local events, this property has something for everyone!

701 Spanish Main Dr Unit 51, 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
701 Spanish Main Dr Unit LOT 49, Cudjoe
$775,000
2 Beds ⋅ 1 Baths ⋅ 620090 MLS
********Nightly Licensed Transient Rental!!!******** This amazing, two bedroom / one bathroom, open water front views , nightly transient rental is ready for you to enjoy both the beauty of this location and the income off the nightly rental license. The floor plan makes the open water views as its main focus. Cook the catch of the day overlooking the waters that you just caught that prized fish in. Sit back and watch your friends and family enjoy those waters with your favorite beverage in hand, and enjoy those fruits of your hard labor. This home is built with easy maintenance in mind, don't worry just enjoy. This home does come with approved engineered plans to build a second bathroom if needed. There is covered parking and a covered storage for all your needs. Just sit back and enjoy this amazing location. This one is location, location, location! Enjoy tropical breezes and island living in this amenity-rich resort-style neighborhood. Venture Out features 24-hour gated security, an oceanfront heated pool, hot tub, fuel station, marina, boat ramp, tennis and pickleball courts, a waterfront picnic pavilion, and much more. Located just 19 miles from Key West and minutes from world-class fishing, diving, and boating, this home offers everything the Keys lifestyle promises - sun, sea, and serenity. Call today for a showing!

701 Spanish Main Dr Unit LOT 49, Cudjoe
22939 Privateer Dr, Cudjoe
$775,000
3 Beds ⋅ 2 Baths ⋅ 619313 MLS
Welcome to your private slice of paradise in desirable Cudjoe Key. this charming well maintained 3-bedroom, 2-bath home sits on an oversized double lot, offering space, privacy, and endless Keys lifestyle potential. With 1,144 square feet of living space, the home is thoughtfully laid out and surrounded by lush tropical surroundings. The property backs up to a private wooded area, creating a peaceful, secluded setting rarely found in the Keys. Step outside and you'll find a true backyard retreat--featuring a resort-style in-ground pool and a tiki hut perfect for entertaining, relaxing, or enjoying those warm island evenings. The expansive lot also provides plenty of parking for vehicles, boats, and all your recreational toys Located just 25 minutes from Key West, you'll enjoy the perfect balance of tranquility and convenience. Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this property captures the essence of Keys living.

22939 Privateer Dr, Cudjoe