Cudjoe Key Real Estate

Cudjoe Key Real Estate

Welcome to Cudjoe Key, a hidden gem nestled in the heart of the Florida Keys! Located in Monroe County, this idyllic island offers a serene escape from the hustle and bustle of everyday life. Just a short drive from Key West, Cudjoe Key is the perfect blend of tranquility and adventure, making it an ideal destination for those seeking a slice of paradise.

Cudjoe Key boasts stunning waterfront views and an abundance of natural beauty. With its lush landscapes, vibrant sunsets, and crystal-clear waters, outdoor enthusiasts will find plenty to love. Whether you're a boating aficionado, a fishing enthusiast, or simply looking to bask in the sun, Cudjoe Key provides endless opportunities for recreation. The surrounding waters are teeming with marine life, making it a prime spot for snorkeling and diving.

In addition to its natural allure, Cudjoe Key is home to a tight-knit community that embraces the laid-back island lifestyle. Here, you can enjoy local dining options that serve up fresh seafood and tropical flavors, as well as unique shops and galleries showcasing the work of local artisans. The island's friendly atmosphere is perfect for families, retirees, or anyone looking to slow down and savor life.

For those considering making Cudjoe Key their home, the real estate market offers a range of options, from charming cottages to luxurious waterfront estates. With its breathtaking views and welcoming community, Cudjoe Key is not just a destination—it’s a lifestyle waiting to be embraced. Come discover the magic of island living in Cudjoe Key, where every day feels like a vacation!

Newest Listings in Cudjoe Key

701 Spanish Main Dr Unit LOT 62, Cudjoe
$225,000
2 Beds ⋅ 1 Baths ⋅ 621584 MLS
NIGHTLY RENTALS ALLOWED! FULLY FURNISHED & MOVE-IN READY! Discover your own slice of paradise in the highly sought-after Venture Out community on Cudjoe Key, just 19 miles from Key West! This beautifully maintained 2-bedroom, 1-bath tropical retreat offers the perfect combination of comfort, coastal charm, and investment potential. Step inside and you'll immediately appreciate the inviting open floor plan, featuring beautiful travertine flooring, a thoughtfully designed kitchen overlooking the living area, and cheerful island-inspired colors that capture the relaxed Florida Keys lifestyle. Don't let the square footage fool you--this home makes excellent use of its space, creating a comfortable and welcoming atmosphere. Offered fully furnished, this property is ready for you to start enjoying immediately! Whether you're searching for a full-time residence, a weekend escape, a seasonal getaway, or an income-producing vacation rental, the possibilities are endless. With 1-day minimum rentals permitted, you have the flexibility to enjoy your Keys retreat whenever you choose and rent it out when you're away. Venture Out is a 24-hour gated waterfront community offering an impressive selection of resort-style amenities, including an oceanfront heated saltwater swimming pool and jacuzzi, marina with fuel dock, boat ramp, convenience store, pickleball, tennis and basketball courts. The community also allows two pets, has no age restrictions, and provides parking for one vehicle. Spend your days boating, fishing, exploring the crystal-clear waters of the Florida Keys, or simply relaxing poolside while soaking up the island sunshine. Your Florida Keys lifestyle starts here! Whether you're looking for your own tropical escape or a vacation rental opportunity, this turnkey property is ready for its next owner. Schedule your private showing today!

701 Spanish Main Dr Unit LOT 62, Cudjoe
701 Spanish Main Dr Unit 198, Cudjoe
$949,600
2 Beds ⋅ 2 Baths ⋅ 621567 MLS
OCEANFRONT INVESTMENT OPPORTUNITY | NIGHTLY RENTALS ALLOWED! Welcome to Oceanview Serenity, a completely renovated 2-bedroom, 2-bath waterfront retreat in the gated Venture Out community on Cudjoe Key at Mile Marker 23. Offering unobstructed open-water views, deep-water access and an established rental history, this turnkey property presents a rare opportunity to combine Florida Keys ownership with income-producing potential. Offered fully furnished and beautifully appointed, the property is move-in and rental ready. With over $105k in gross rental income ytd for 2026 and more than $33k in future bookings! An attractive option for investors seeking a property in the Florida Keys that allows nightly rentals. It is equally suited for use as a primary residence, second home or private tropical getaway. Recent improvements add significant value and peace of mind, including a brand-new 2026 roof, newly installed heavy-duty tie-down straps and refurbished and protected under-house support beams. Inside, the bright coastal interior has been thoughtfully updated throughout. Expansive windows frame panoramic turquoise-water views, while the renovated kitchen features new appliances and an oversized center island with abundant built-in storage and breakfast-bar seating. A Nest smart thermostat provides convenient climate control and energy management. The spacious primary suite includes an upgraded ensuite bath with double vanity and generous storage. Outdoors, a covered deck provides an exceptional setting for enjoying ocean breezes and spectacular Florida Keys sunrises. A massive 61ft concrete seawall and convenient deep-water access make this an outstanding choice for boating enthusiasts. Venture Out offers an impressive collection of resort-style amenities, a large oceanfront saltwater pool, marina store, fuel dock, boat ramps, lighted tennis and pickleball courts, basketball, bocce, and 24/7 gated security. Buy, Live, Rent, & Enjoy Paradise!

701 Spanish Main Dr Unit 198, Cudjoe
701 Spanish Main Dr Unit LOT 336, Cudjoe
$330,000
621560 MLS
NIGHTLY RENTALS ALLOWED! ROGO EXEMPT! DIRECT OPEN WATER ACCESS! An incredible opportunity to own a waterfront RV lot in the highly desirable Venture Out community on Cudjoe Key! Whether you're looking for an income-producing investment, your own tropical getaway, or the opportunity to build your dream Florida Keys home, Lot 336 offers exceptional flexibility. This ROGO-exempt, buildable lot is ready for your RV, featuring a concrete pad with 30/50-amp electrical service, water, and sewer hookups already in place. Enjoy ample space for RV slide-outs, outdoor seating, and additional storage. Boating enthusiasts will appreciate the 60-foot-wide, deep-draft canal, complete with a concrete 17 FT seawall and no bridges to open water! Enjoy fishing right from your seawall or head out to Kemp Channel for easy access to the Gulf, nearby sandbars, and some of the best boating and fishing the Florida Keys have to offer. Located just 25 miles from Key West, Venture Out is a gated waterfront community offering resort-style amenities, including an oceanfront heated saltwater swimming pool, jacuzzi, marina with fuel dock, convenience store, boat ramp, pickleball, tennis and basketball courts. Transient rentals with a one-night minimum are permitted, creating an exciting opportunity for investors seeking short-term rental potential. Additional community features include parking for one vehicle, no age restrictions, and allowance for up to two pets. Bring your RV, build your island retreat, or explore the rental potential -- the possibilities are endless! Schedule your private showing today and start living the Florida Keys lifestyle!

701 Spanish Main Dr Unit LOT 336, Cudjoe
701 Spanish Main Dr Unit 543, Cudjoe
$329,000
2 Beds ⋅ 2 Baths ⋅ 621559 MLS
Enjoy your own Florida Keys getaway with the flexibility of nightly rentals! Located on a spacious corner lot in the gated Venture Out community on Cudjoe Key, this 2-bedroom, 1.5-bath home is offered fully furnished and currently operates as a vacation rental. Inside, the kitchen features generous cabinet space and tiled countertops, with an open connection to the dining area that makes everyday living and entertaining easy. Tile flooring throughout, built-in bedroom and hallway storage, and a stackable washer and dryer add comfort and convenience. Updates include central air conditioning and heat installed in 2024, plus impact-resistant windows and a sliding door installed in July 2024. Vinyl siding and a metal roof complement the home's easy-care appeal. Venture Out offers 69 acres of waterfront community living with access to both Atlantic and Gulf waters. Boaters will appreciate the community boat ramp, marina store with fuel and bait, and boat washdown station. Spend your days enjoying the 80-foot heated pool, hot tub, kiddie pool, saltwater swimming lagoon, lighted tennis courts, basketball, and bocce. A convenience market, post office, and golf-cart-friendly setting make island life even more convenient. Whether you're looking for a personal retreat, an income-producing vacation property, or a combination of both, this furnished corner-lot home offers a welcoming place to make it happen with Key West just a short drive away.

701 Spanish Main Dr Unit 543, Cudjoe
165 Colson Dr, Cudjoe
$1,645,000
3 Beds ⋅ 2 Baths ⋅ 621554 MLS
Beautiful modern design meets tropical estate living in this stunning half-acre property on Cudjoe Key! Just 21 miles from Key West, with Key West International Airport offering a growing list of flights reaching all over the country, this private retreat puts island life within easy reach. Built in 2023, this 3 bed / 2 bath coastal contemporary offers 1,696 sq ft of light-filled living beneath soaring 15-ft vaulted ceilings, plus expansive covered porches that catch the ocean breeze and frame stunning open-water views. Thoughtfully upgraded by the current owners, the property now offers a complete Keys lifestyle with a new concrete pool and sun shelf, poolside tiki hut, lush grass lawn, new tropical landscaping, and custom black aluminum fencing - a rare bonus in the Keys and a dream for four-legged family members. Offered beautifully furnished and move-in ready, with like-new Restoration Hardware and Room & Board furnishings, making it easy to begin enjoying the Keys lifestyle from day one. Built to last with CGI impact windows and doors, metal roof, blown-in foam insulation, Cambria Quartz, and Sonos throughout. Wired for an exterior elevator lift, with a free-standing storage shed built to 180 mph, and ample parking for an RV, trailer, and toys. No HOA. Public utilities include FKAA water service, connection to municipal sewer, Keys Energy for electric service, and high speed digital cable. For boating, access to the Blimp Rd community boat ramp or the Cudjoe Gardens Marina are just five minutes away. Enjoy some of the Keys' best restaurants and cafes nearby, with nightly live music and outdoor dining. This is fantastic Keys living! Check out the video to see more.

165 Colson Dr, Cudjoe
701 Spanish Main Dr Unit 321, Cudjoe
$799,000
2 Beds ⋅ 2 Baths ⋅ 621504 MLS
Boating is at the heart of life at Venture Out Unit 321. This elevated, canal-front 2-bedroom, 2-bath home has a 35-foot concrete dock and seawall, with easy access from the community to both the Atlantic Ocean and the Gulf of Mexico. Enjoy canal and open-water views from the covered porch after a day on the water. Inside, 963 square feet of living space includes an open kitchen with stainless steel appliances and a breakfast bar. Below the home are covered parking, shaded outdoor space, and storage. The property also features a metal roof, impact windows, and accordion shutters and is offered furnished. Venture Out at Cudjoe Cay permits nightly rentals and offers two onsite boat ramps, an onsite boat fuel station, a marina & convenience store, oceanfront heated pool and spa, and sports courts. Plus lots of community activities! With your boat docked at home and so much close at hand, Unit 321 is ready for the Florida Keys lifestyle.

701 Spanish Main Dr Unit 321, Cudjoe
701 Spanish Main Dr Unit LOT 643, Cudjoe
$255,000
621496 MLS
Your own piece of paradise awaits! This 35' x 69' RV lot in Venture Out offers full hookups and a home base for enjoying the Florida Keys. Bring your rig, settle in, and spend your days fishing, boating, or relaxing by the pool. Enjoy a gated, golf cart-friendly community with 24-hour security, tennis, pickleball, and a marina. Local favorites like Morning Joint, Square Grouper, and 420 Lounge are just minutes away, with Key West only 19 miles down the road. Whether you're planning a winter escape, enjoying retirement, or looking for an investment opportunity, this ROGO-exempt lot puts the Keys lifestyle within reach.

701 Spanish Main Dr Unit LOT 643, Cudjoe
22960 Sharp Ln, Cudjoe
$525,000
2 Beds ⋅ 1 Baths ⋅ 621494 MLS
Canal front property with immediate 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 302, Cudjoe
$359,000
621490 MLS
Rare pull-through RV lot in Venture Out with ocean views, pool views, and exceptional resort-style amenities--an outstanding opportunity for personal use, seasonal enjoyment, or rental income. Positioned directly across from the community pool, this desirable lot offers a front-row setting near the pool, hot tub, showers, laundry facilities, barbecue area, and party space. Enjoy beautiful ocean views right from the lot while being steps from the amenities that make Venture Out such a sought-after destination. This is one of only approximately 10 pull-through RV lots among roughly 659 lots in the community--a truly uncommon feature that provides added convenience and strong appeal for RV owners and renters alike. Pull-through lots rarely become available, making this a standout opportunity in one of the Florida Keys' most popular waterfront RV communities. Venture Out permits nightly rentals, creating excellent potential for investors seeking a flexible, income-producing property in a high-demand vacation market. Whether you plan to enjoy the lot yourself, rent it when you are away, or do both, this property offers location, convenience, and strong rental appeal. Within walking distance, enjoy the marina, tennis courts, pickleball courts, bocce court, basketball courts and community store. Venture Out's gated resort lifestyle combines waterfront living, recreation, and investment potential in one exceptional package. Be ready for next season--opportunities like this do not come to market often. Do not wait; this rare pull-through lot is expected to move quickly.

701 Spanish Main Dr Unit 302, 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
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