Cudjoe Key Homes with Conventional Finance Terms

Cudjoe Key Homes with Conventional Finance Terms

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys, Monroe County! This enchanting island offers a perfect blend of natural beauty, vibrant community, and unparalleled access to the stunning waters of the Atlantic Ocean. Whether you're seeking a serene retreat or a lively coastal lifestyle, Cudjoe Key has something for everyone.

Cudjoe Key is renowned for its breathtaking sunsets, lush tropical landscapes, and an abundance of outdoor activities. With its proximity to world-class fishing, diving, and snorkeling spots, outdoor enthusiasts will find endless opportunities to explore the rich marine life and coral reefs that surround the island. The tranquil atmosphere and friendly community make it an ideal place for families, retirees, and anyone looking to escape the hustle and bustle of city life.

When it comes to real estate, Cudjoe Key offers a variety of homes that cater to different tastes and budgets. The market features charming single-family homes, waterfront properties, and cozy cottages, many of which are available with conventional financing options. This means that your dream home in this tropical paradise is within reach, whether you’re looking for a permanent residence or a vacation getaway.

With its convenient location just a short drive from Key West, residents can enjoy the best of both worlds – the tranquility of island living and the vibrant nightlife and cultural attractions of the mainland. Discover the magic of Cudjoe Key, where your dream lifestyle awaits amidst the sun, sea, and swaying palms!

Newest Cudjoe Key Homes with Conventional Finance Terms

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
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
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
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
23057 Bluegill Ln, 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
94 Sacarma Dr, 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
342 Spanish Main 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
125 Colson 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
174 Tortuga Ln, 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
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