Cudjoe Key Homes with Canal Front Waterfront features

Cudjoe Key Homes with Canal Front Waterfront features

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys, within Monroe County. This idyllic island paradise offers a unique blend of tranquility, natural beauty, and vibrant marine life, making it the perfect destination for those seeking a slice of paradise. With its stunning waterfront views and lush tropical surroundings, Cudjoe Key is a haven for outdoor enthusiasts, water sports lovers, and anyone looking to escape the hustle and bustle of everyday life.

One of the most alluring features of Cudjoe Key is its charming homes with canal front waterfront access. Imagine waking up each morning to the gentle sound of waves lapping against your dock, with the sun rising over the water, casting a golden glow on your doorstep. These homes offer not only breathtaking views but also the opportunity for easy access to the open waters of the Atlantic Ocean and the Gulf of Mexico. Boating, fishing, and kayaking become part of your everyday routine, allowing you to fully embrace the island lifestyle.

The community of Cudjoe Key is tight-knit and welcoming, with a laid-back atmosphere that encourages residents to enjoy the beauty of their surroundings. Whether you're looking for a cozy retreat or a spacious family home, the canal front properties here offer a unique blend of comfort and adventure. With easy access to local amenities, dining, and entertainment options, Cudjoe Key is not just a place to live; it’s a lifestyle waiting to be embraced. Come discover the magic of Cudjoe Key and find your dream home on the water today!

Newest Cudjoe Key Homes with Canal Front Waterfront features

22960 Sharp Ln, Cudjoe
$525,000
2 Beds ⋅ 1 Baths ⋅ 621494 MLS
Canal front property with immideate exit out of canal to Cudjoe Bay only 230 ft out of the canal. Ocean side of Cudjoe Key, 40 ft wide canal. Nice view down from the from the back cap rock area. 60 ft on the canal. Deep canal with turtles. Lot is approx. 60 X 100 ft lot with 17+ ft on either side of house and 30 ft. deep yard in front and 35 ft. in the back yard. Property can be fenced and room to park your vehicles. 975 sq.ft ''1980'' 2bedroom/1bth floor plan. Poured concrete slab under home. Certificate of occupancy included, if you ever decide to build new,you could have a nice view. No home owners association. VE12 Flood zone, Improved Subdivsion Zoning, Tier 3, lot. Cash offers only with proof of funds. Being sold 'AS IS'' No tresspassing, please schedule to see property. By appointment only.

22960 Sharp Ln, Cudjoe
701 Spanish Main Dr Unit 455, Cudjoe
$399,999
1 Beds ⋅ 1 Baths ⋅ 621464 MLS
Looking for your own little piece of paradise? This waterfront home may be the one. Situated along a canal, it offers beautiful water views from the 17-foot concrete dock, complete with a covered back patio ideal for grilling or relaxing. The patio also features a mini sink, mini fridge, and mini freezer for your entertaining pleasure. The spacious primary suite includes a king-size bed, custom closets with built-in drawers, and large windows overlooking the back patio. The beautifully updated bathroom features a walk-in shower with glass doors, handrail, built-in bench, skylight, humidifier, and exhaust fan. A versatile bonus room can serve as a second bedroom, office, or additional living space. The upgraded kitchen boasts granite countertops, a glass-tile backsplash, and stainless-steel appliances, including a gas range with convection oven and air fryer, center burner includes a griddle feature, a refrigerator with bottom drawer freezer, a microwave, and disposal. Additional features include a pantry with drawers, a 70-pound propane tank, an on-demand hot water heater, four ductless AC units, and a full-size stackable washer and dryer conveniently tucked into the hallway closet. Numerous hallway closets provide ample storage. All windows are double paned. The home features a gable metal hip roof, gutters, Bahama and panel shutters, and reinforced FEMA-approved piers. The oversized concrete driveway provides parking for both a car and a golf cart. Large doors offer easy access to plenty of additional storage beneath the home. Venture Out offers an abundance of amenities, including oceanfront picnic areas and tiki huts, boat ramps, a marina with fuel dock and store, heated saltwater pool, hot tub, tennis and pickleball courts, bocce courts, basketball courts, community bathhouses, laundry facilities, and a clubhouse with ongoing activities. The community is completely walled, gated, and secured with on-site security guards.

701 Spanish Main Dr Unit 455, Cudjoe
20731 W 2nd Ave, Cudjoe
$3,200,000
5 Beds ⋅ 4 Baths ⋅ 621433 MLS
Experience exceptional boating and effortless Florida Keys living from this meticulously maintained Cudjoe Key residence, ideally positioned on a wide canal just 2 homes from open water. Lush tropical landscaping surrounds the property, while protected wetlands across the canal create a peaceful, private backdrop. Offering 4 Bedrooms plus an Office and 4 Baths, the home features 112' of concrete seawall and dockage, a 20,000 lb. boat lift and quick access to open water. Designed to embrace indoor-outdoor living, the living room features a Euro Door Wall System with sliders that open completely to the expansive screened porch with sitting and dining areas. Remote-controlled Kevlar hurricane screens provide added protection, while the waterfront retreat features a heated and chilled saltwater pool, poolside tiki, travertine decking and outdoor shower. With the rear of the home facing west, unforgettable Florida Keys sunsets unfold over the water and protected wetlands. The kitchen features granite countertops, Wolf cooktop, Electrolux large capacity refrigerator, wine cooler and dedicated ice maker. The spacious primary suite offers a soaking tub, walk-in shower and dual vanities. One guest bedroom features an ensuite bath, while 2 additional guest bedrooms share a Jack-and-Jill bath. A dedicated office adds flexible space. Additional features include a laundry room with dog wash, 2-car garage with convenient side access to the waterfront, and impact windows and doors. A nearby full-service marina and waterfront restaurant add to the ease of this sought-after boating neighborhood. Beautifully maintained inside and out, this property captures the privacy, boating access and outdoor lifestyle that make the Florida Keys so special.

20731 W 2nd Ave, Cudjoe
459 Pattison Dr, Cudjoe
$2,299,995
3 Beds ⋅ 2 Baths ⋅ 621419 MLS
Set on a large, private lot at the corner of two canals, this 3-bedroom, 2-bath, 2,020 sq. ft. waterfront home offers exceptional outdoor living, quick boating access and multiple spaces designed to enjoy the Florida Keys lifestyle. Boaters will enjoy the updated dock and 15K-lb boat lift. The outdoor space is built for entertaining, featuring a waterfront pool with paver decking, a poolside screened lanai, a main-floor screened porch, and an expansive rooftop deck with sweeping ocean views. Inside, the Great Room is filled with natural light, highlighted by an arched window framing views of the pool and canal, with easy access out to the rooftop deck and screened porch. The adjacent kitchen comes fully equipped with granite countertops, stainless steel appliances, and a pantry closet. The main level houses a dedicated guest wing with two bedrooms, one opening to a front porch balcony and the other stepping directly out to the rear screened porch, plus a full guest bathroom with a jetted soaking tub. Upstairs, the top floor serves as a completely private primary suite and second living area. This retreat features a soaking tub, walk-in closet, direct sun deck access showcasing open water views, and steps leading up to the rooftop deck. Additional features include impact-resistant windows and doors, a one-car garage, carport and plenty of storage for your island essentials. The neighborhood also offers the convenience of a full-service marina and waterfront restaurant close to home. With quick open-water access putting world-class fishing, diving and snorkeling within easy reach, this home is perfectly positioned to enjoy the best of the Florida Keys waterfront lifestyle.

459 Pattison Dr, Cudjoe
111 Doubloon Ln, Cudjoe
$850,000
2 Beds ⋅ 2 Baths ⋅ 621355 MLS
Welcome to island waterfront living on desirable Cudjoe Key! Situated on an amazing corner lot, this beautifully maintained 2-bedroom, 2-bath home offers the perfect combination of comfort, convenience, and easy access to both the Atlantic & Gulf. Inside, you'll find an updated kitchen featuring beautiful cabinetry, granite countertops, vaulted ceilings and plenty of space for entertaining. Impact-resistant windows and doors provide added protection and contribute to the home's low insurance costs. Gorgeous screened in porch and outdoor shower overlooking the canal. Generous storage throughout makes it easy to keep all your fishing, boating, and island-living essentials close at hand. Boaters will love the quick access to open water, making it easy to spend your days fishing, diving, or exploring everything the Florida Keys have to offer. The oversized corner setting provides additional space and privacy while capturing the relaxed tropical lifestyle Cudjoe Key is known for.

111 Doubloon Ln, Cudjoe
701 Spanish Main Dr Unit 283, Cudjoe
$450,000
621336 MLS
Fabulous location with a concrete pad for your RV and comes ROGO exempt if you ever decide to build a stilted home. Close to pool, marina, marina store, boat ramp, fuel docks, washdown, and all the amenities Venture Out has to offer. Including pickle ball & tennis courts, heated pool, spa, clubhouse, 24 hour security guard and more. 35' dock on a wide 60' canal with a short ride out to the Gulf or Ocean for world class fishing and diving. Complete with 50amp, 110 & 220 service with water and sewer. Venture Out allows daily, weekly, and monthly rentals all located in the desirable Cudjoe Key.

701 Spanish Main Dr Unit 283, Cudjoe
701 Spanish Main Dr Unit 123, Cudjoe
$674,999
2 Beds ⋅ 2 Baths ⋅ 621327 MLS
YOUR FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully furnished 2-bedroom, 2-bath home combines water views, exceptional boating access, comfortable island living, and resort-style amenities just seconds from open water. Situated on a wide 60' canal, boaters will love the 35' concrete dockage with dock posts, cleats, swim ladder, and fish-cleaning table--perfect for days spent fishing, diving, cruising, or exploring the Keys. Inside, the bright and inviting living space opens onto a covered porch, creating the perfect place to relax after a day on the water. The home has been extensively updated, including a new kitchen in 2026, new flooring in 2022, A/C in 2020, and a new roof, siding, windows, doors, insulation, and hot water heater in 2019. A beautiful tongue-and-groove ceiling adds to the relaxed island feel. The primary suite features a king-size bed, ample storage, and private ensuite bath, while the guest bedroom offers a queen-size bed and access to the second full bath. Venture Out offers an incredible resort lifestyle with a heated pool, hot tub, marina, fuel dock, boat ramps, tennis, pickleball, bocce, basketball, playground, recreation hall, pavilion, 24-hour gated security, and more. Nightly rentals are permitted, and the home generated approximately $84,000 in gross rental revenue, providing an attractive added benefit when you're not enjoying it yourself. Seller financing may also be considered with acceptable terms. Beautifully furnished and ready to enjoy, this is your opportunity to experience the Florida Keys lifestyle from day one.

701 Spanish Main Dr Unit 123, Cudjoe
701 Spanish Main Dr Unit 171, Cudjoe
$799,000
2 Beds ⋅ 2 Baths ⋅ 621307 MLS
YOUR OCEAN FRONT FLORIDA KEYS ESCAPE AWAITS! Welcome to your own slice of paradise in the highly sought-after gated community of Venture Out on Cudjoe Key. This beautifully maintained 2-bedroom, 2-bath elevated home combines incredible ocean views, exceptional boating access, and resort-style living in one of the Lower Keys' most desirable waterfront communities. Step inside to soaring ceilings, abundant natural light, and expansive windows that bring the beautiful ocean views into the home. Covered outdoor spaces invite you to embrace the Keys lifestyle, from morning coffee overlooking the water to evening cocktails after a day on the boat. The primary suite features a king bed and ensuite bath, while the guest bedroom offers a queen bed and its own private covered porch. Boaters will love the 35' concrete seawall with heavy-duty dock posts, cleats, swim ladder, and two fish-cleaning tables. Below the home, covered parking, generous outdoor living space, and a 12'x12' concrete storage enclosure provide plenty of room for all your boating, fishing, and island gear. Venture Out offers an incredible resort lifestyle with a heated pool, hot tub, marina, fuel dock, boat ramps, pickleball, tennis, bocce, basketball, playground, recreation hall, pavilion, 24-hour gated security, and more. Nightly rentals are permitted, and the home generated approximately $100,000 in gross rental revenue in 2025, providing an attractive added benefit when you're not enjoying it yourself. Sold turnkey and ready to enjoy, this is your opportunity to own a waterfront retreat and experience the Florida Keys lifestyle from day one. Seller financing may also be considered with acceptable terms.

701 Spanish Main Dr Unit 171, Cudjoe
701 Spanish Main Dr Unit 236, Cudjoe
$300,000
621280 MLS
LOWEST-PRICED WATERFRONT LOT IN VENTURE OUT! Discover your own slice of the Florida Keys at Lot 236 in Venture Out on Cudjoe Key. This beautifully landscaped waterfront lot offers a rare combination of privacy, tropical surroundings, and incredible potential in one of the Keys' most sought-after gated communities. Tucked along a peaceful canal, the property features a 13.25-foot concrete seawall and lush tropical landscaping that creates a private and inviting setting. A separate seating area nestled beneath the shade of mature palm trees provides the perfect place to relax and enjoy the laid-back Florida Keys lifestyle. Thinking about building in the future? This lot is ROGO exempt, offering a rare opportunity for future development. The property also offers excellent rental potential with nightly rentals allowed! As a Venture Out resident, you'll enjoy an impressive collection of amenities, including a large saltwater swimming pool overlooking the ocean, marina store and fuel station, two lighted tennis courts, pickleball, basketball, bocce, recreation hall, community pavilion, and boat ramp. The golf-cart-friendly community offers plenty of ways to relax, stay active, and enjoy the Florida Keys lifestyle. Priced as the lowest-priced waterfront lot in Venture Out, Lot 236 is a rare opportunity to own a piece of paradise with privacy, water views, and incredible investment potential.

701 Spanish Main Dr Unit 236, Cudjoe
22968 Drake Ln, Cudjoe
$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
1106 Thatch Ln, Cudjoe
$2,099,000
4 Beds ⋅ 4 Baths ⋅ 621161 MLS
Set along a peaceful canal on Cudjoe Key, this 2016 residence pairs solid CBS construction with an unmistakably elevated sense of island living. This 4 bedroom, 3.5 bath home features impact windows and doors and a standing seam metal roof, speaking to a level of craftsmanship built to endure, while 2,548 square feet of living space and roughly 1,370 square feet of balconies invite the surrounding water views and tropical air into everyday life. The main level is designed for both privacy and gathering, offering 3 guest bedrooms, 2 full baths and a laundry room alongside a second living area that opens onto a spacious covered balcony. One bedroom enjoys its own ensuite, while the remaining two share a well-appointed Jack and Jill bath. Ascend to the main living level and the home opens into a bright and airy Great room where kitchen, dining and living areas unfold together. Anchored by a substantial island and dining bar, the kitchen is finished with Silestone countertops, a sea glass tile backsplash and abundant custom cabinetry. Beyond, another expansive balcony extends the living space into the open air, ideal for evening entertaining or a quiet morning coffee. The primary suite occupies its own private wing upstairs, offering generous closets and a spa inspired ensuite with a jetted tub and separate walk-in shower. Outside, a heated and chilled concrete pool sets the stage for effortless indoor-outdoor living, while a 30-foot concrete dock with lighting and bubblers provides canal access for boating, paddling or an evening line in the water, with the open water just minutes beyond. Located just minutes from local restaurants, shopping and coffee shops, this a rare balance of quality, privacy and island sophistication, backed by a proven rental history that makes it as compelling an investment as it is a home.

1106 Thatch Ln, Cudjoe
22970 Gasparilla 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
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