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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
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
$1,999,000
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
701 Spanish Main Dr Unit 609, Cudjoe
$459,000
621103 MLS
Canal-front Paradise Awaits! Incredible view from your seawall! RV Lot 609 in Venture Out. Experience the epitome of waterfront Florida Keys living on this Canal Front RV Lot with 40' Seawall nestled within an exclusive gated community. This beautiful canal front property boasts: * Prime Canal front Location: Enjoy direct access to the water from your private 40 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 RV Lot has been very well cared for and maintained and is ready for you to bring in your RV 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 609, Cudjoe
21423 Overseas Hwy, Cudjoe
$1,247,500
1 Baths ⋅ 621081 MLS
Prime Lower Keys Commercial Real Estate for sale. Excellent visibility and easy access from Overseas Hwy. Corner location at MM 21 and Blimp Rd. Total of 3 Parcels of Land. With the Submerged Baybottom parcels total over 3 Acres with Approx. 37,748 sf. or .87 Acres of useable uplands. Uplands portion is approx. 200' of highway frontage by 190' deep. Waterfront property with limited shallow water access for kayak and canoes. Existing 1,250 sf. CBS building on site may be enlarged or demo and entirely redevelope. Property has favorable SC- Suburban Commercial Zoning with many Commercial uses allowed and possible. Great location for a local contractor, retail convenience store, or marine/boat/trailer/ RV and Auto storage.

21423 Overseas Hwy, 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 LOT 266, Cudjoe
$514,900
620843 MLS
Premier Waterfront RV Lot in Venture Out | 35' Seawall, Ocean Views & Proven Rental Income! Whether you are looking for your own personal Florida Keys getaway or a high-performing investment property, this lot offers the perfect blend of luxury, location, and lucrative returns. Boasting a consistent rental history, this turn-key property is a proven income producer with established guest demand. • Prime Waterfront & Ocean Views: Enjoy breezes and water views right from your patio. • 35-Foot Concrete Seawall: Perfect for boaters and anglers! Equipped with dock posts, cleats, swim ladder and quick, direct access to both the Atlantic Ocean (for offshore fishing/diving) and the Gulf backcountry (for calm-water cruising). • Spacious Pad & Full Hookups: Accommodates large RVs with plenty of room for outdoor lounging and dining. Equipped with 30/50 amp electric, water, and sewer connections. • Proven Cash-Flow Investment: Strong year-round and seasonal rental track record with repeat visitors. Located at Mile Marker 23, Venture Out is one of the Lower Keys' premier resort communities. Ownership includes full access to a wealth of luxury resort features: • 🏊 Heated Saltwater Swimming Pool & Hot Tub • 🚤 Private Marina, On-Site Fuel Station, Boat Ramp & Wash Station • 🎾 Tennis, Pickleball, Bocce Ball, and Basketball Courts • 🛒 On-Site Convenience Store, Fish Cleaning Stations, & Bathhouses • 🔒 24/7 Gated Security Patrol for complete peace of mind

701 Spanish Main Dr Unit LOT 266, Cudjoe
22776 Overseas, Cudjoe
$350,000
620822 MLS
Prime Cudjoe Key Commercial Opportunity! Cleared Suburban Commercial parcel offering outstanding highway frontage and excellent visibility on the Overseas Highway. Zoning SC allows for a variety of uses flood zone AE 9 tier 3 lot. For investment or owner-use. Owner financing may be available to qualified buyers. Bring your vision and capitalize on one of the Lower Keys' high-exposure commercial locations. Buyer to verify all info. No trespassing . Cameras on site.

22776 Overseas, 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
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
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