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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

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 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

22832 John Silver Ln, Cudjoe
$849,000
3 Beds ⋅ 3 Baths ⋅ 620998 MLS
CUDJOE KEY CANALFRONT SPECIAL - LOWEST PRICED HOME IN CUTTHROAT HARBOR ESTATES. ASSUMABLE MORTGAGE AT 2.75% MOTIVATED SELLERS SAY BRING ALL OFFERS!! Situated on over 6,000 Square Feet on a deep water canal - this recently updated property provides easy boating access to both the Gulf and the Atlantic, making it a perfect home base for world class fishing, diving, SANDBARS and enjoying the keys lifestyle. New Upgrades Include - Fully remodeled kitchen All impact doors and windows All new split AC Units New flooring New Tankless Water Heater Upstairs, you'll find the fully remodeled kitchen with island which is perfect for entertaining and walk out to a large deck space. 1 Large bedroom and recently remodeled bathroom. The lower level features two bedrooms with a living room and an office space!!! A simple door and kitchenette could provide an owners lockout dividing both floors. Ample size lot provides room for Boat/RV parking in addition to a lush tropical landscape that provides afternoon shade on the majority of the property. This deal will not last long so do not delay on owning your piece of paradise. CALL LISTING AGENT MIKE KANE DIRECTLY FOR YOUR PRIVATE SHOWING AND SAVE!!!!!

22832 John Silver 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

701 Spanish Main Dr Unit 533, Cudjoe
$239,000
1 Beds ⋅ 1 Baths ⋅ 620746 MLS
Welcome to Unit 533 in the gated waterfront community of Venture Out on Cudjoe Key! This well-maintained home features a spacious addition that provides extra living space and versatility. The addition includes a comfortable living area and a flex room currently used as additional sleeping space--ideal for guests, a home office, or hobby room. The property is currently occupied by a long-term tenant, offering an opportunity for a buyer seeking immediate rental income. The home offers a functional layout suitable for full-time living, seasonal enjoyment, or future investment use. Venture Out permits transient rentals with no minimum-night requirement, giving owners flexibility in how they choose to use the property. Community amenities include a large heated and chilled saltwater pool, hot tub, swimming lagoon, full-service marina with boat ramp and fuel dock, and convenient boating access to both the Gulf of Mexico and the Atlantic Ocean. Residents and guests also enjoy pickleball, tennis, bocce ball and basketball courts, a playground, two community centers, organized activities, and on-site church services. Looking for a fresh start? The property may also offer the potential to be converted into an RV lot or rebuilt to suit your vision, subject to current building regulations and community requirements. Schedule your private showing and explore the possibilities at Unit 533!

701 Spanish Main Dr Unit 533, Cudjoe

701 Spanish Main Dr Unit 246, Cudjoe
$444,999
1 Beds ⋅ 1 Baths ⋅ 620685 MLS
Ocean-View Waterfront Retreat in Gated Venture Out on Cudjoe Key. NIGHTLY RENTALS ALLOWED Enjoy the Florida Keys lifestyle in this well-maintained 1-bedroom, 1-bathroom waterfront home located in the highly desirable gated community of Venture Out. With ocean views, direct boating access, excellent amenities, and nightly rentals permitted, this property is ideal as a vacation home, income-producing investment, or full-time residence. The home features numerous updates, including a new roof in 2018, air-conditioning system in 2020, and hot water heater in 2025. Additional improvements include newer impact-resistant windows, Bahama shutters, powder-coated storm panels, and updated mobile home tie-downs for added peace of mind. Boaters will appreciate the 35-foot concrete seawall with dock whips and quick access to the backcountry, offshore waters, and Atlantic Ocean. A concrete slab beneath the home provides valuable storage for fishing gear, kayaks, bicycles, and other Keys essentials. Venture Out offers an impressive array of amenities, including a large oceanfront saltwater swimming pool, community marina with fuel station, boat ramp, and boat wash-down area. Residents and guests also enjoy lighted tennis and pickleball courts, basketball and bocce courts, a recreation hall, waterfront pavilion, and regular community activities. The golf-cart-friendly neighborhood makes it easy to enjoy everything the community has to offer. Whether you are searching for a relaxing island escape, strong rental opportunity, or waterfront home in the Lower Keys, this property delivers an exceptional combination of location, boating access, amenities, and investment potential. Schedule your private showing today and experience this special Cudjoe Key property for yourself.

701 Spanish Main Dr Unit 246, 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

701 Spanish Main Dr Unit 424, Cudjoe
$549,000
2 Beds ⋅ 2 Baths ⋅ 620346 MLS
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 424 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been very well cared for and updated and is ready for you to move in and enjoy. * Gated Community: 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 a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! * Excellent rental income potential!!

701 Spanish Main Dr Unit 424, 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

22822 Buccaneer 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

701 Spanish Main Dr Unit 659, 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

701 Spanish Main Dr Unit 639, Cudjoe
$425,000
2 Beds ⋅ 1 Baths ⋅ 619998 MLS
Enjoy the Salty Air from this Key Lime Gem in the Florida Keys! This furnished, 2 bedroom, 1 bathroom manufactured home has high ceilings that allow great entertaining from the kitchen, dining room, and living room area. Features a large master bedroom, full size bathroom with new vanity and new stackable washer/dryer, well stocked kitchen with a full line of appliances, metal roof, and tile floor throughout. Enjoy the tropical landscaped backyard while grilling dinner or relaxing on your private deck. Indulged in the community's amenities, including an oceanfront heated saltwater pool and jacuzzi for ultimate relaxation. A marina with a fuel dock, convenient store and boat launch for the boater enthusiasts. Stay active and engaged with pickleball and tennis courts! And for Kids' there's a playground where the little ones can have fun. Venture Out is an individual owned residential condominium community with 24 hour gated security, located only 19 miles from the vibrant city of Key West! Parking for one vehicle, no age restrictions, two pets allowed, and transient (1 day) rentals are permitted. Possible Seller Finance

701 Spanish Main Dr Unit 639, Cudjoe

116 Spanish Main Dr, Cudjoe
$1,269,000
2 Beds ⋅ 2 Baths ⋅ 619922 MLS
Discover your personal sanctuary in the heart of Cudjoe Key, where authentic Florida Keys charm meets modern coastal luxury. This stunning 2-bedroom, 2-bathroom home has been thoughtfully updated to offer the ultimate waterfront lifestyle, just 21 miles from Key West's world-class dining and entertainment. The interior glows with natural light, highlighted by impact-resistant windows and elegant French doors leading to an open canal front balcony. The floor plan is designed for effortless living, featuring a sleek kitchen with a central island, 2025 updated Oven, Dishwasher, & microwave, remodeled bathrooms, a versatile bonus room, and a separate dining area that provides a front-row seat to the tranquil canal. For added convenience, the spacious walk-in closet includes an integrated washer and dryer, while a temperature-controlled thermostat and security system ensure year-round peace of mind. Perfectly situated for the avid mariner, the exterior features a concrete dock and a 10,000lb elevator boat lift. The lift currently accommodates a 2024 Boston Whaler 250 Outrage with twin 200hp Mercury Verado engines (no trailer), which is available for separate purchase. Enjoy a short, scenic canal ride from your backyard directly to the open ocean. Step outside into a secluded tropical retreat. The exterior boasts brand-new Hardie Board siding and a privacy fence encompassing an inground concrete pool finished with an elegant travertine pool deck. Beneath the home, a shaded entertaining space provides the perfect spot for lounging, complete with an outdoor shower and ample storage for kayaks, grill and water toys. Complete with a dedicated garage and plenty of parking, this property is the perfect home for family enjoyment as a primary residence or a seasonal retreat. Whether you are looking to make wonderful lifelong memories or simply wish to offset ownership expenses with a winter rental, this Cudjoe Key gem captures that sought-after ''Keys feel'' in every

116 Spanish Main Dr, Cudjoe

21012 6th 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

22939 Gasparilla Ln, 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

22961 John Avery 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

22953 John Silver Ln, Cudjoe
$949,000
3 Beds ⋅ 2 Baths ⋅ 619680 MLS
Where boating lifestyle and modern coastal design align, this fully renovated 3-bedroom, 2-bathroom home in Cudjoe Key delivers exceptional waterfront living. This completely reimagined residence is ideally positioned on a premier corner canal lot, offering approximately 190 feet of concrete seawall and dockage along two waterways, an exceptional setting for boating and waterfront enjoyment. Thoughtfully renovated throughout, the home showcases a clean coastal-modern design with new impact windows and doors, an elevated interior finish, and a beautifully updated kitchen featuring sleek cabinetry, premium surfaces, and an open layout ideal for entertaining. Light-filled living spaces flow seamlessly onto the newly replaced covered rear porch, where tranquil canal views create the perfect backdrop for relaxed indoor/outdoor living. The exterior stairs have also been recently replaced, complementing the home's refreshed and well-maintained feel. Boating enthusiasts will appreciate the 10,000 lb boat lift, expansive seawall/dockage, and quick access to open water via Cudjoe Bay. Downstairs, a large enclosure provides abundant storage space for tools, fishing gear, and boating equipment, an invaluable feature for Keys living. Located on a quiet street in an established neighborhood, this property offers a rare combination of modern updates and generous waterfront in the Lower Florida Keys.

22953 John Silver Ln, Cudjoe

20868 W 5th Ave, 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

21025 3rd Ave, Cudjoe
$1,299,000
3 Beds ⋅ 2 Baths ⋅ 619427 MLS
Experience the best of ocean-side living with no bridges to open water--a true boater's dream! This spacious 3-bedroom, 2-bath home offers 1,741 square feet of comfortable living designed for both relaxation and entertaining. A charming paver walkway welcomes you to elegant double-door entry, opening into a bright and expansive living area with soaring high ceilings. The open layout flows effortlessly into a well-appointed kitchen featuring stainless steel appliances. A dedicated dining area adds to the home's inviting feel. The private Master Suite is a peaceful retreat, complete with French Doors leading to a screened patio where you can enjoy gentle breezes year-round. A guest bedroom also features direct patio access with French Doors offering comfort and convenience for visitors. Step outside and embrace the waterfront lifestyle with an impressive 80-foot concrete dock, just minutes from open water and nearby marina access--ideal for boating, fishing, or simply enjoying the Florida Keys lifestyle. This is more than a home--it's your gateway to effortless coastal living. Don't miss this must-see opportunity!

21025 3rd Ave, Cudjoe

22978 Port Royal Ln, 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* Great Opportunity for affordable canal front home *

22978 Port Royal Ln, Cudjoe

701 Spanish Main Dr Unit 423, Cudjoe
$267,000
1 Beds ⋅ 1 Baths ⋅ 619175 MLS
$21,000+ Gross Rental Revenue so far in 2026! Welcome to Conch Hideaway #423, a charming and income-producing tropical retreat located within the highly sought-after gated community of Venture Out in the Lower Florida Keys. This 1-bedroom, 1-bath island getaway offers the perfect blend of relaxed coastal living and strong investment potential. Currently operating as a successful vacation rental, the property has already generated over $21,000 in gross rental revenue for 2026, with approximately $17,000 in existing future reservations already secured as of June 5, 2026. Whether you're searching for a personal Florida Keys escape, a turnkey investment property, or both, this home is already producing income and ready to enjoy. Inside, you'll find a bright, coastal-inspired interior featuring an open-concept living space, Smart TV, and a pull-out sofa bed. The thoughtfully designed kitchen offers everything needed for easy vacation living, while the bedroom and full bathroom create a comfortable retreat after a day on the water. Step outside and relax in your outdoor space and enjoy the tropical breezes. A separate storage shed provides convenient space for fishing gear, bicycles, and beach essentials. Located at Mile Marker 23 on Cudjoe Key, Venture Out is a private, 24-hour gated oceanfront community known for its exceptional amenities and vibrant island atmosphere. Residents and guests enjoy access to a heated saltwater oceanfront pool and hot tub, boat ramp, fuel dock, ship store, tennis and pickleball courts, basketball and bocce courts, saltwater swimming lagoon, recreation center, market, post office, and golf cart-friendly streets throughout the community.

701 Spanish Main Dr Unit 423, Cudjoe

701 Spanish Main Dr Unit 604, Cudjoe
$595,000
2 Beds ⋅ 2 Baths ⋅ 618979 MLS
Owner says ''Bring All Offers'' Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed. Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a cozy and inviting interior, complete with all the essentials for a seamless transition. The open-concept living area flows effortlessly, providing a warm atmosphere for gatherings or quiet evenings. Outside, you'll find a concrete seawall, perfect for fishing enthusiasts and water lovers alike. The included fish cleaning station makes it easy to prepare your catch right at home. With ample outdoor storage space underneath the house, you'll have plenty of room for kayaks, fishing gear, or seasonal decorations. Located in a prime area that allows for nightly rentals, this property is not only a fantastic home but also a lucrative investment opportunity. Whether you're looking to enjoy your own slice of paradise or generate rental income, this home has it all. Don't miss your chance to own this charming coastal retreat. As part of the Venture Out community, you'll enjoy an array of amenities at your doorstep. Dip into the massive saltwater swimming pool overlooking the ocean, or take advantage of the marina store and fuel station. Sports enthusiasts will love the two lighted tennis courts, pickleball, basketball, and bocce courts. The recreation hall and community pavilion host a variety of activities and events, making it easy to connect with neighbors and make new friends. This golf cart-friendly community also features a boat ramp, giving you direct access to the stunning waters of the Florida Keys. Whether you're looking for a vacation home, rental investment, or a permanent paradise, this property has it all!

701 Spanish Main Dr Unit 604, Cudjoe

701 Spanish Main Dr Unit 182, Cudjoe
$485,000
1 Beds ⋅ 1 Baths ⋅ 613336 MLS
Oceanfront Paradise Awaits! Unit 182 in Venture Out Experience the epitome of Florida living in this charming one-bedroom, one-bathroom mobile home with Florida Room nestled within an exclusive gated community. This beautifully maintained home boasts: * Prime Canal front Location: Enjoy breathtaking ocean views and direct access to the water from your private 35 ft seawall. * Community Boat Ramp and boat washdown station. * Spacious Florida Room: Expand your living space with a delightful air-conditioned Florida room, perfect for relaxing and soaking in the coastal breeze. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been meticulously cared for and is ready for you to move in and enjoy. * Gated Community: 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 a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! Plenty of potential for rental income.

701 Spanish Main Dr Unit 182, Cudjoe

701 Spanish Main Dr Unit 453, Cudjoe
$509,000
2 Beds ⋅ 2 Baths ⋅ 618300 MLS
Canal-front Paradise Awaits! Incredible view from your back deck! Unit 453 in Venture Out. Experience the epitome of waterfront Florida Keys living in this charming two-bedroom, two-bathroom mid-rise mobile home nestled within an exclusive gated community. This beautiful canal front home boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 17 ft seawall. * Community Boat Ramp and boat washdown station. * Community Amenities: Indulge in a resort-style lifestyle with access to a huge heated pool, spa, clubhouse, pickleball courts, tennis courts, basketball courts, bocce courts, ocean swimming area and more! * Well-Maintained: This home has been very well cared for and updated and is ready for you to move in and enjoy. * Gated Community: 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 a secure and exclusive gated community. Don't miss this rare opportunity to own a piece of paradise! * Exclusivity: The gated community adds a sense of security and prestige. * Nightly Rentals Allowed! * Excellent rental income potential!!

701 Spanish Main Dr Unit 453, Cudjoe

701 Spanish Main Dr Unit 265, 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