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

22968 Drake Ln, Cudjoe
$1,799,000
3 Beds ⋅ 2 Baths ⋅ 621138 MLS
OPEN WATER VIEWS - BRAND NEW CUSTOM WATERFRONT HOME - DOUBLE LOT & MOVE IN READY. This ELEVATED 3 bedroom, 2 bathroom CBS home is a must see! Solid steel and concrete, standing seam white metal roof with impact windows and doors rated to 185 MPH. 2,050 total sq ft of living space includes a front porch, utility room on the lower level and a lanai off the back. A total of 1500 sq ft of living space under air with a spacious open floor plan. An aluminum powder coated spiral stair case will lead you to an UPPER DECK where you can capture views of the sunrise and sunset along with panoramic views of Cudjoe Bay, the Atlantic Ocean and surrounding Keys. The kitchen features an Island with quartz countertops and custom cabinetry. Black stainless steel appliances. Tray ceilings and special features set this home apart. The front entrance and rear exit entry feature a red mahogany stained cypress ceiling matched perfectly to blend with the brass door handles. No details are spared with the elegance of the home's interior finishes. Ceramic tile cut on the diagonal throughout the interior and exterior porch and lanai. This home is being sold turn key with brand new furnishings as seen in the listing photos. Excellent boating access to both Cudjoe Bay and the Atlantic Ocean with 130' of canal frontage. Take over active permit for a 10 x 30 ft dock with all fees including mitigation fees already paid in full. Plenty of room for an in-ground 12 x 30 ft pool. Also possible to build on the adjoining lot with ROGO approval. Very low insurances, less than $4000 per year for Homeowners/Wind. Schedule your private showing and discover coastal living at it's finest in the Florida Keys!

22970 Gasparilla Ln, Cudjoe
$982,600
2 Beds ⋅ 2 Baths ⋅ 621115 MLS
Welcome to Oceanview Serenity, an exceptional, open-water retreat located in the gated community of Venture Out at Cudjoe Key (Mile Marker 23). This completely renovated 2-bedroom, 2-bathroom mid-rise offers rare, unobstructed turquoise ocean views as if you are floating on the water. A true boater's paradise, the property boasts a massive concrete seawall with effortless deep-water access. Critical structural and exterior updates provide unmatched peace of mind and substantial insurance benefits, including a brand-new roof, newly installed heavy-duty tie-down straps, and freshly refurbished, protected under-house support beams. Go inside to a bright, turnkey coastal interior where every detail has been thoughtfully updated, complete with a smart Nest thermostat for effortless climate control and energy efficiency. The main living space is framed by expansive windows that showcase panoramic water views. The heart of the home is a fully upgraded kitchen outfitted w/new appliances, and an oversized central island featuring generous built-in storage and a breakfast bar. The spacious primary suite serves as a luxurious private haven, highlighted by an upgraded ensuite bathroom complete with a double vanity and abundant storage. Outside, the covered deck offers the ultimate vantage point to relax in the ocean breeze and take in breathtaking Florida Keys sunrises over the water. Offered fully furnished and tastefully appointed, this home is 100% move-in ready to enjoy as a primary residence, private tropical getaway, or income-producing investment as a nightly rental. Venture Out is one of the rare communities in the Lower Keys that permits lucrative nightly rentals. Enjoy an incredible lineup of resort-style amenities, featuring a massive oceanfront saltwater swimming pool, an on-site marina store with a fuel dock, boat ramps, lighted tennis and pickleball courts, basketball, bocce, a vibrant recreation hall, and 24/7 gated security.

701 Spanish Main Dr Unit 198, Cudjoe
$1,349,000
3 Beds ⋅ 2 Baths ⋅ 620916 MLS
Look no further--this exceptional property truly has it all. This beautifully maintained CBS home boasts open-water views and is situated on an oversized lot on an extra-wide, deep canal, great for bigger boats, and just three houses in from the end. You'll be up on plane in seconds, with unparalleled boating access to both the Atlantic and Gulf. Ideally located closest to the premier backcountry of the Lower Florida Keys, this is the perfect property for the fishing and diving enthusiasts and still only 20 minutes to Key West. Built by Tom Ryan Construction, this solid CBS 3-bedroom 2-bath home is almost 1,300 square feet, and has a spacious, open feel, created by the thoughtful layout and vaulted ceilings in the main living area. The kitchen features granite countertops, a convenient breakfast bar, and a dedicated dining area, making it ideal for both everyday island living and entertaining. The primary suite has a walk in closet and french doors leading out to the porch, while the second bedroom has a pocket door creating another convenient ensuite for guests. Most days you'll enjoy outdoor dining or cocktails and the relaxed island life from the covered, screened porch overlooking the canal with open water views of Kemp Channel. The views continue into the primary suite and kitchen, offering a beautiful waterfront backdrop throughout the home. The lower enclosure provides plenty of space for a vehicle, workshop, and storage. Two 500-gallon cisterns provide ample water for maintaining the lush tropical landscaping. The solid concrete step down seawall features davits each with a 5,500 lift capacity. This property is the ideal location to be able to spend a stellar day on the water, then head to Key West to one of the many fabulous restaurants for dinner, and finish the evening listening to live music or take in a show at one of our unique boutique theaters. You can have it all.

23057 Bluegill Ln, Cudjoe
$2,060,000
5 Beds ⋅ 3 Baths ⋅ 620686 MLS
Rare Licensed Oceanfront Short-Term Vacation Rental in the Lower Florida Keys, with SELLER FINANCING OFFERED! Welcome to Fandango, a highly successful transient (daily-weekly) vacation rental home offering an exceptional investment opportunity and a personal retreat. This stunning 5-bedroom, 3-bathroom property, built in 2011 and expanded in 2018, was thoughtfully designed as the ultimate family vacation rental retreat. Featuring an adjacent oceanfront parcel with a private beach, kayaks, and a floating dock for fishing or docking boats up to 24 feet, this property provides everything needed for fun and relaxation. Outdoors, enjoy a sparkling swimming pool, soothing hot tub, tropical landscaping with coconut palms and banana trees, and a screened-in porch for al fresco dining. Inside, the open floor plan includes four king bedrooms and a fifth bedroom with a queen and single bed, smart TVs, and updated appliances. Centrally located at MM21.5, Fandango is just 20 minutes from Key West, 10 minutes from Big Pine Key, and 15 minutes from Bahia Honda State Park, with dining options nearby, including a 5-star restaurant within a mile. This property is offered fully furnished and equipped, including bookings into 2027 and 10-years' average income of $160+k. Professional property management is in place, ensuring both secure investment returns and worry-free family vacations. This low-maintenance, turn-key home offers the rare opportunity to own one of the few legally licensed short-term rentals in the Lower Keys. Owning a vacation rental property means you're not just paying for vacations--you're building equity and unlocking financial benefits, all while eliminating the scramble for accommodations every trip. Show up, relax, and let your investment work for you.

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

342 Spanish Main Dr, Cudjoe
$2,195,000
5 Beds ⋅ 3 Baths ⋅ 620325 MLS
TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

125 Colson Dr, Cudjoe
$1,270,000
3 Beds ⋅ 2 Baths ⋅ 620186 MLS
Florida Keys Living at Its Best! Welcome to 174 Tortuga Lane, a beautifully maintained waterfront home in the heart of Cudjoe Key, where world-class fishing, boating, and island living are in your backyard. With 37 feet of dockage, you'll have quick access to the Atlantic, backcountry waters, and some of the best fishing the Florida Keys has to offer. Built in 2020 for peace of mind and low-maintenance ownership, this 3-bedroom, 2-bath home features impact windows and doors, HardiePlank siding, Trex decking, aluminum railings, and a 180-mph wind rating. Inside, you'll find a bright, coastal-inspired interior with 9-foot ceilings, luxury vinyl plank flooring, an open-concept living area, spacious eat-in kitchen, pantry, separate laundry room, and a comfortable primary suite with walk-in closet and oversized bath. The fabulous outdoor space is where this property shines. Since the home was built, a stunning concrete pool was added in 2022, creating the perfect place to cool off after a day on the water. Relax under the new tiki hut, rinse off in the outdoor shower, challenge friends and family on the putting green, or simply enjoy the constant ocean breezes and beautiful open water views across the street. The oversized fenced lot offers plenty of room to spread out, while the covered front porch and legal downstairs storage provide additional functionality. There's even 50-amp service for an RV or electric vehicle charger. Whether you're looking for a full-time residence, vacation home, or Keys getaway, 174 Tortuga Lane delivers the boating lifestyle, outdoor amenities, and island charm that make the Florida Keys so special.

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

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

135 Tortuga Ln, Cudjoe
$487,000
2 Beds ⋅ 2 Baths ⋅ 620156 MLS
Seller is Motivated! Coastal Charm Meets Modern Comfort Welcome to your island escape in the heart of the Lower Keys! This beautifully furnished two-bedroom, two-bath stilt home is located within the gated waterfront community of Venture Out on Cudjoe Key. Inside, you'll find a bright, open-concept layout featuring a spacious living area that flows seamlessly into a thoughtfully designed kitchen. Recent updates include a brand-new refrigerator, ample cabinetry, and a modern island bar with additional seating, perfect for entertaining family and friends. Built with both comfort and durability in mind, the home features a reliable metal roof and a large ground-level storage enclosure for all your island essentials. Step outside to your private backyard retreat, complete with low-maintenance artificial turf and a cozy seating area, ideal for enjoying the Florida Keys sunshine. This property is a proven income-producing vacation rental with strong rental history and future bookings already in place. In 2025, the home generated $43,257.28 in rental revenue. As of June 2, 2026, it has already produced $18,472.78 year-to-date, with 8 future reservations estimated to generate an additional $13,092.57 in rental income that will transfer to the buyer. Conveniently located near the front gate of the community, this home offers easy access for pet owners, with a quick path for walking dogs just outside the neighborhood. You're also within walking distance of Venture Out's outstanding amenities, including a heated saltwater waterfront pool, swimming lagoon, private boat ramp, tennis courts, pickleball courts, bocce courts, basketball courts, marina store, community center, and more. Whether you're seeking a personal island retreat, a seasonal getaway, or an investment property with immediate income potential, this home offers the perfect combination of comfort, convenience, and Florida Keys charm.

701 Spanish Main Dr Unit 659, Cudjoe
$2,499,000
4 Beds ⋅ 2 Baths ⋅ 620071 MLS
Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and effortless waterfront living, the 2,739-square-foot home features 4 bedrooms, a spacious open-concept great room, bamboo flooring, impact windows and doors, and a durable metal roof. The chef's kitchen is the heart of the home, offering a large center island, stainless steel appliances, abundant cabinetry, and a wine refrigerator and is the perfect gathering place for entertaining family and friends. Step outside to a beautifully landscaped tropical setting with expansive screened lanai overlooking the water and an 82-foot dock complete with boat lift and kayak launch. Whether you're heading offshore for a day of fishing, enjoying sunset cruises, or simply relaxing by the water, this property delivers the Keys lifestyle you've been dreaming about. The 2- car Garage offers plenty of parking and room for all or your toys while the oversized double lot provides privacy and space to enjoy the outdoors while taking advantage of the home's unique corner-like waterfront setting. Located in one of the Lower Keys' most desirable boating communities, Cudjoe Gardens offers deep-water canals capable of accommodating larger inboard vessels, plus convenient access to a full-service marina with fuel, bait, boat ramp, refreshments, and a waterfront restaurant. Just 20 minutes from Key West, you'll enjoy world-class dining, entertainment, and island living while returning home to a peaceful waterfront retreat.

21023 2nd Ave, Cudjoe
$1,399,000
2 Beds ⋅ 2 Baths ⋅ 619865 MLS
Island living becomes effortless at this beautifully maintained waterfront retreat in the heart of Cudjoe Gardens. Located on a deep-water canal with quick ocean access, this CBS pool home offers the rare combination of ground-level convenience while above the flood plain. From the moment you arrive the property feels inviting and relaxed. Tropical landscaping and manicured grounds create a private island atmosphere while the standing seam galvanized roof and concrete construction provide lasting durability and peace of mind. Inside, the home radiates warmth and coastal character. Vaulted wood tongue-and-groove ceilings draw your eyes upward and create an airy, open feel throughout the living spaces. The thoughtfully designed floor plan flows seamlessly between the kitchen, dining, and living areas, making the home ideal for entertaining family and friends after a day on the water. The kitchen is both stylish and functional with updated stainless appliances, generous cabinetry, pantry and a large dining bar for casual dining. Picturesque pool and water views are enjoyed from the living areas and primary suite. Outside is where this property truly shines. The new waterfront pool creates a resort-style centerpiece from the living area and is surrounded by multiple lounging and entertaining spaces. Relax beneath the tiki hut with a morning coffee, gather around the waterfront firepit at sunset, or enjoy evenings under the stars with the gentle breeze coming off the canal. For boating enthusiasts the deep-draft canal accommodates larger boats with a new 17K boat lift and quick ocean access. The nearby full-service marina offers fuel, bait, refreshments and boat ramp access while the neighborhood waterfront restaurant adds another layer of convenience and charm. Plenty of room for of your gear and toys in the 2-car attached garage. Located 20 minutes from Key West offering the perfect balance between peaceful island living and access to world-class dining and culture.

21012 6th Ave, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 619835 MLS
Welcome to your ROOFTOP RETREAT - a beautifully remodeled waterfront home at 22939 Gasparilla Lane in Cudjoe Key, where panoramic ocean views and relaxed Keys elegance come together in perfect harmony. From the spectacular rooftop deck to the light-filled interior, shimmering turquoise water creates a breathtaking backdrop throughout the home. This thoughtfully updated 3-bedroom, 2-bath concrete block residence offers 1,434 square feet of refined coastal living, enhanced by rich wooden ceilings that add warmth, character, and timeless island charm. The open living spaces flow effortlessly to the screened porch overlooking the canal -- the ideal setting for morning coffee, sunset cocktails, or unwinding after a day on the water. Designed with both comfort and functionality in mind, the property features a new metal roof, covered parking, fenced grounds, and a spacious downstairs utility/workshop area perfect for boating gear, paddleboards, fishing equipment, or hobbies. Perfectly positioned on a canal in the Lower Keys with easy boating access, Rooftop Retreat captures the essence of waterfront living with unforgettable ocean vistas and an inviting coastal atmosphere. Whether you're searching for a private island getaway, a second home, or an exceptional investment opportunity, this property delivers the very best of the Keys lifestyle.

22939 Gasparilla Ln, Cudjoe
$895,900
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
$1,150,000
2 Beds ⋅ 2 Baths ⋅ 619465 MLS
Welcome to your cozy coastal retreat in Cudjoe Gardens in the beautiful Florida Keys! This well maintained 2bedroom, 2bath CBS home offers 1,344 sq ft of comfortable island living with thoughtful upgrades throughout. Step inside to find custom cabinetry, adding both style and functionality to the home's inviting interior. Outside is where this property truly shines, featuring a private, small man made sandy beach, concrete seawall, and boat lift, making it a boater's dream with easy access to open water. Relax and entertain in true Keys fashion with a spacious patio, tiki hut, and outdoor shower Perfect after a day on the water. The garage provides added storage and convenience, while the cozy layout makes this home ideal as a full time residence, vacation getaway, or investment property. Located just minutes from Cudjoe Gardens Marina, local dining favorites, and world-class fishing and diving, this home offers the perfect blend of tranquility and adventure. Experience laid back coastal living at its finest your Keys escape awaits!

20868 W 5th Ave, Cudjoe
$875,000
2 Beds ⋅ 1 Baths ⋅ 619325 MLS
Ocean side location enjoy diving , fishing, dining from your boat come home to relax on your deck watching the sunset. Open floor plan new upgrades throughout.Several pictures added with staged furnishing for you to see what rooms could look like.Extra large property with plenty of room for your R/V, boats. Your own boat launch with plenty of dockage on your concrete seawall. Beautifully landscaped. Two large storage sheds with additional interior storage underneath the home. Here is a piece of paradise to grab and hang onto too. Only 20 minutes to Key West. Seller motivated Seller is motivated to sell this one of a kind location with private boat ramp with 90 feet of concrete seawall. Very large property* Plenty of room for all your requirements can keep R/V , boat trailer, extra vehicle and more* OCEAN SIDE* Some of the best boating opportunities in the Florida Keys* New Price to sell ASAP

22978 Port Royal Ln, Cudjoe
$3,300,000
3 Beds ⋅ 3 Baths ⋅ 619314 MLS
Experience elevated island living in this striking modern residence in Cudjoe Key, where sleek design meets the raw beauty of the Atlantic. This white contemporary home showcases a dramatic wall of glass along the oceanfront, creating a seamless connection between indoor living and the endless horizon beyond. The open-concept living space is flooded with natural light and anchored by breathtaking water views, where dolphins, rays, and vibrant marine life become part of your daily backdrop. Three luxurious en-suite bedrooms offer refined comfort and privacy, including a main-level guest suite and two upper-level retreats--one featuring a spa-inspired bath with a glass-tiled walk-in shower, the other with a soaking tub overlooking the ocean. Outdoor living is truly resort-inspired, with a private pool, expansive pool deck, and a fully appointed cabana lounge complete with bar, TV, and entertaining space. A rare private beach invites effortless paddle-outs into crystal-clear, opal-toned waters. Multiple balconies and a spectacular rooftop deck provide unforgettable sunrise and sunset views. The chef's kitchen is both functional and striking, featuring an oversized island with unique stone countertops, walk-in pantry, and direct access to a balcony with grilling area. Additional highlights include a poolside grill, ground-level laundry and storage, private dock, and boat ramp with immediate access to world-class fishing and diving. Located just 30 minutes from Key West, this exceptional waterfront retreat delivers the ultimate blend of modern luxury, privacy, and the unmatched lifestyle of the Lower Florida Keys.

1083 Labat Ln, Cudjoe
$1,799,000
3 Beds ⋅ 3 Baths ⋅ 618500 MLS
Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock, direct ocean access via a 60-ft wide canal, and proximity to the neighborhood marina. Enter through a covered entry into an airy Great Room with soaring ceilings and newly installed marble-look tile, giving the space a crisp, clean feel. The spacious kitchen features warm wood cabinetry, generous counter space, and casual bar seating—ideal for entertaining. A primary suite retreat includes his-and-hers closets and a spa-like bath, plus an adjacent den that offers flexibility as a 4th bedroom, home office, or studio. The attached 2-car Garage allows plenty of space for all your toys. The tropically landscaped yard with shady palms and pretty brick drive boasts picturesque curb appeal. Cudjoe Gardens offers a full-service marina, fueling station, and a charming canal-side restaurant—all moments from your front door. Just 20 miles to Key West, this is an exceptional opportunity to enjoy world-class boating and tropical elegance without stairs or compromise.

51 Sawyer Dr, Cudjoe
$1,575,000
3 Beds ⋅ 2 Baths ⋅ 618413 MLS
The Best Boating Access in the Lower Keys, hands down!!! The 'Island Life' awaits you in this stunning well thought out custom designed canal front property. This solid CBS home, nestled in lush tropical landscaping, features 3 bedrooms and 2 baths on an oversized 10,200 sq.ft. lot located in the tranquil setting of sought after Cudjoe Ocean Shores. This subdivision is extremely desirable due to the generous spacing between homes, as well as having the best boating access to BOTH the Atlantic and Gulf via Kemp Channel. Kemp is one of the deeper easier channels to navigate to the Gulf and has a much higher bridge clearance to get under US 1 for quick access to the Atlantic. This combined with having 85' of canal frontage on an extra wide canal with lots of room to maneuver, makes this property perfect for bigger boats. The luxurious tongue and groove western red cedar lined ceilings carry through to the exterior porch and soffit. High end red Burch cabinets, granite counters, and Italian travertine flooring compliment the cathedral ceilings perfectly. The pocket style sliders allow you to open the entire living area up to the covered porch to create an even grander feel. The gourmet kitchen offers a Sub Zero 156 bottle wine cooler with 2 temperature zones in addition to top of the line appliances such as Bosch, and kitchen Aid. The split floor plan is ideal for added privacy. All bedrooms have 9' ceilings and cedar lined closets w/custom shelving while the baths feature granite counters on solid maple vanities with Alinea True Color Cosmetic light fixtures. Throughout this home you'll find gorgeous custom tile and marble work top shelf hardware and fixtures. This home also has a 36 KW whole house generator, a 1,200 lb. cargo elevator lift, a 17,000 lb. boat lift, and a circular paver driveway. No expense was spared!! Across from government-owned land, ensuring additional privacy and a naturally tranquil setting.

22865 Redfish Ln, Cudjoe
$879,000
2 Beds ⋅ 2 Baths ⋅ 618239 MLS
This Truly Spectacular Oceanfront Property offers the ultimate waterfront lifestyle and is a one of a kind, featuring an impressive 98' seawall. Designed to capture the best of coastal living, the property combines 72' of concrete seawall along a protected canal with 26' of direct Atlantic Ocean Frontage, delivering both tranquility and open-ocean beauty. A waterfront lovers dream, the canal side is fully equipped with six heavy duty dock posts and cleats, ideal for boating, fishing, and easy water access. This beautifully maintained home features two bedrooms and two full bathrooms, with tile flooring throughout, a metal roof, central air conditioning and abundant storage. The bright, open interior is surrounded by windows galore in the living area, perfectly framing the stunning outdoor scenery and flooding the home with natural light. The primary bedroom opens directly to a large covered porch, where you can wake up to breathtaking sunrises over the Atlantic. Outside, enjoy a spacious patio perfect for evening gatherings, moonrises and watching the incredible sealife. Additional features include accordion shutters and a full line of appliances, making this home as functional as it is beautiful. Located in Venture Out on Cudjoe Key, a private and gated community. Residents enjoy 24 hr gated security and patrol, two pets allowed and transient rentals permitted. The community amenities are unmatched and include: Oceanfront heated saltwater pool, hot tub, marina with ship store, fuel dock, two boat ramps, two tennis courts, two pickleball courts, basketball, bocce ball and playground for the kids. This is a rare opportunity to find your happy place in paradise. Seller says bring offers

701 Spanish Main Dr Unit 265, Cudjoe
$350,000
2 Beds ⋅ 1 Baths ⋅ 618674 MLS
Welcome to your slice of the Florida Keys lifestyle! This charming beach-themed retreat is the perfect blend of cozy comfort and coastal style. This 2-bedroom, 1-bathroom turnkey home is move-in ready -- whether you're looking for a full-time residence, vacation getaway, or income-producing rental. FULLY FURNISHED. Step inside to a fresh, inviting living space designed for relaxed island living. The bright white kitchen pops with marble countertops and a stunning blue tile backsplash, bringing those breezy ocean vibes right into your home. It's light, cheerful, and perfect for entertaining friends and family after a day on the water. And here's the best part -- even though this property sits on a dry lot, you still enjoy beautiful open water views. Venture Out is one of the most sought-after gated communities in the Lower Keys, known for its active lifestyle and incredible amenities: Heated community pool, Marina & boat ramp with direct ocean and Gulf access, Tennis & pickleball courts, Basketball courts, Private convenience store, Children's playground & pool, Recreation hall, 24-hour gated security. Bring your boat, your golf cart, and your flip-flops -- this neighborhood was made for enjoying the water. Located just 20 miles from Key West, you're close enough for dining, nightlife, and the airport -- but far enough away to enjoy peaceful island living. If you've been dreaming of a cozy, beach-inspired Keys escape with income potential and resort-style amenities... this is the one. Ready to make your move?

701 Spanish Main Dr Unit 536, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 618382 MLS
Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you to your deeded dock equipped with water and electric, giving you effortless ocean access just steps from your door. The interior is light, open, and welcoming, with a focus on bringing the outside in. Enjoy a wraparound porch that frames panoramic views of the Atlantic, while inside you'll find an open floor plan with tile floors and island-inspired charm throughout. The entire second level is dedicated to a spacious primary suite, complete with a cozy sitting area overlooking the sea. Cudjoe Cove offers low HOA dues, a resort-style pool with waterfall, and trailer storage. Just 20 minutes from Key West and moments from restaurants, a marina, and conveniences — this home is ideal as a full-time residence, a second home, or a vacation getaway.

21250 Conch Dr, Cudjoe
$535,000
2 Beds ⋅ 2 Baths ⋅ 617289 MLS
Oceanfront Paradise Awaits! Unit 247 in Venture Out experience the epitome of Florida living in this charming, fully furnished two-bedroom, two-bathroom mobile home nestled within an exclusive gated community. Enjoy breathtaking ocean views and direct access to the water from your private 17 ft seawall. Community amenities include a boat ramp and boat washdown station after returning from a day on the water. A resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area with tiki huts and more! Cruise around the property in your golf cart to the community store or to join in on the numerous community activities. Live with peace of mind in an exclusive gated community which adds a sense of security and prestige. This home is ready for you to move in and enjoy! Don't miss this rare opportunity to own a piece of paradise! Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 247, Cudjoe
$2,795,000
4 Beds ⋅ 3 Baths ⋅ 618526 MLS
Florida Keys luxury island living at its finest. Welcome to your private slice of tropical island living in coveted Cudjoe Gardens—a true boater's dream set on an oversized double canal-front lot (approx. 15,200 sq. ft.) with an impressive close to 200 feet of concrete seawall. This beautifully designed CBS home offers 4 bedrooms, 3 baths, and nearly 3,000 sq. ft. of living space, thoughtfully arranged for relaxed living and effortless entertaining. Recent renovations elevate the home even further, with the kitchen and primary bath completely and tastefully reimagined by D'Asign Source. The stunning chef's kitchen now features Omega cabinetry, elegant quartzite stone surfaces, premium KitchenAid appliances, and a striking black walnut round dining table that anchors the space with warmth and natural beauty—perfect for gathering with family and friends. Pocket sliding doors open the living areas to a spacious screened Florida Room (approx. 494 sq. ft.), seamlessly blending indoor and outdoor living. Outside, enjoy mature tropical landscaping, extensive paved driveways and walkways, and resort-style spaces designed for relaxing and entertaining. For boating enthusiasts, this property truly shines: approx. 4' control depth, quick access to the reef and backcountry, protected canals, and proximity to a full-service marina. The seawall is fully equipped with a cut-in boat slip, 15,000 lb. boat lift, davits, swim ladder, and outdoor shower—everything you need for life on the water. Additional highlights include a barrel tile roof, an attached 2 car garage, a versatile 676 sq. ft. garage space ideal for storage, hobbies, or island toys. Whether you're hosting sunset gatherings by the pool, heading out for a day on the water, or simply unwinding in your own tropical retreat, this remarkable property offers the perfect blend of comfort, style, and true Florida Keys lifestyle. Come see this exceptional canal-front retreat, where every day feels like a getaway.

20920 5th Ave, Cudjoe
$1,399,000
3 Beds ⋅ 2 Baths ⋅ 617709 MLS
Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while embracing modern luxury. Impact doors and windows, wide-plank engineered wood flooring, and an updated chef's kitchen with gas range create interiors that are both stylish and functional—ideal for relaxed living and elegant entertaining. The serene Primary Suite is a private sanctuary, featuring expansive picture windows that frame stunning views of the home's massive, newly refurbished waterfront pool, evoking a true resort-style experience. Designed for the boating enthusiast, the property offers deep-water dockage on a flow through canal with a concrete dock and 10,000-lb boat lift, providing effortless access to open water. A whole-house generator with automatic transfer switch ensures uninterrupted comfort and peace of mind year-round. Located within one of the Keys' most desirable waterfront neighborhoods, residents enjoy access to the Cudjoe Gardens Marina a full-service marina with fuel, bait, refreshments, and boat ramp, along with a beloved Bent Prop waterfront restaurant—all just moments from home This is a rare opportunity to own a historically significant, architecturally distinctive residence that seamlessly blends mid-century design, modern upgrades, and an unparalleled waterfront lifestyle.

51 Drost Dr, Cudjoe
$399,900
2 Beds ⋅ 1 Baths ⋅ 618353 MLS
This charming and meticulously maintained property is perfect for anyone looking to start enjoying the tropical paradise of the Florida Keys. It comes fully furnished with a cozy coastal style and features 2 bedroom, 1 bathroom, and an enclosed patio area with a pull-out bed and living area. The living room is bright and spacious, while the kitchen is open and easily accessible for entertaining on the patio. The garden patio at the entrance is an ideal spot to admire the beautiful mornings and evenings outside. Conveniently located in the popular Venture Out Park, this property offers all the amenities you could want. This includes a ships store, marina with fuel docks, boat ramp, large, heated pool with a saltwater filtration system, spa, showers, kiddie pool, tennis courts, pickleball courts, and even a post office, all within a secure, guard-gated entrance. Additionally, Venture Out allows for daily, weekly, and monthly rentals, making it a true paradise!

701 Spanish Main Dr Unit 140, Cudjoe