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Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

31 Beds ⋅ 19 Baths ⋅ 610484 MLS

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions), over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Shared coin laundry, 2 swimming pools, 3 private driveways. 2 parcels on US 1 are zoned Sub Urban Commercial, excellent rental history. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment

21540 21470 Overseas Hwy, Cudjoe

$12,999,999

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Excellent rental history, shared coin laundry, 2 swimming pools. 2 parcels on US 1 are zoned Sub Urban Commercial, 3 private driveways. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment. Seller is licensed Realtor

31 Beds ⋅ 19 Baths ⋅ 612522 MLS

Located on Cudjoe Key, only 20 miles from Key West. Transient use property, over 3.5 acres, 15 units (15 ROGO exemptions) over 300 feet of water frontage, boat basin, 3 concrete docks, one wooden dock, boat ramp. Excellent rental history, shared coin laundry, 2 swimming pools. 2 parcels on US 1 are zoned Sub Urban Commercial, 3 private driveways. Property spans from US 1 to the Atlantic Ocean. Owner is licensed Realtor. Please do not walk on the property without an appointment. Seller is licensed Realtor

21540 21470 Overseas Hwy, Cudjoe

$5,750,000

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

13 Beds ⋅ 7 Baths ⋅ 620213 MLS

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor. 5 (2 bedroom one bath cottages) and one (3 bedroom 2 bath house), 6 water meters, 6 electric meters. Heated salt water pool. The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$5,750,000

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

13 Beds ⋅ 7 Baths ⋅ 618705 MLS

Rare income-producing open-water compound on Cudjoe Key featuring 5 cottages plus a spacious main house. This gated, turnkey waterfront property offers direct open-water views, private dockage with ample boat space, on-site boat ramp, swimming pool, and lush tropical landscaping. Ideal for vacation rental income, corporate retreat, or private family compound. Each unit is well-appointed for guest comfort and positioned to maximize privacy. Excellent boating access to world-class fishing and diving. Strong investment opportunity in the Lower Keys with established income potential. Zoned Sub Urban Residential with one Buildable Sub Urban Commercial Lot, verify with the County. Included Parcel#'s Sub Urban Residential 00174920-000200, 00174920-000300, 00174920-000400, 00174920-000000, 00174920-000100, 00174920-000500. Sub Urban Commercial 00174920-000600. Owner is licensed Realtor The property is also listed with 9 additional units MLS #612522.

21470 Overseas Hwy, Cudjoe

$3,200,000

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.

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

$3,099,000

Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 3 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

4 Beds ⋅ 3 Baths ⋅ 619589 MLS

Welcome to a refined waterfront pool home in the highly desirable Cudjoe Gardens neighborhood, where luxury meets laid-back island living. Located on a corner canal with 235' of waterfront this home is designed with life on the water in mind. Featuring two boat lifts, 15,000 lb and 12,000 lb, providing flexibility for multiple vessels along with a 2-car Garage for additional storage for all of your gear. Inside, the spacious 3 Bedroom, 3 Bath 3,056 sq. ft. home comfort and style blend with ease. The kitchen stands out with 6-burner Viking Range, Viking dishwasher, cabinet-front refrigerator, stainless appliances, pantry and generous space for entertaining, flowing seamlessly into the main living areas. Soaring ceilings fills the home, creating a bright and inviting atmosphere throughout. Upstairs a loft-style office and a dedicated theatre room offering a bar with beverage center provides the perfect setting for movie nights or game-day gatherings. The primary suite serves as a private retreat, complete with a lavish bath with bidet, separate shower and a relaxing jet tub, ideal for unwinding at the end of the day. Porches on both sides of the home overlook the canals and lead to a unique sandy point at the corner, offering a peaceful setting to take in water views and stunning sunset skies. After a day on the water relax by your waterfront heated salt pool or enjoy sipping cocktails on the screened lanai. Additional amenities include impact windows and doors, whole house generator and ice machine. Cudjoe Gardens is an upscale waterfront community known for its ground-level concrete homes thoughtfully built above the floodplain. The neighborhood is home to Cudjoe Gardens Marina, a convenient full-service stop for fuel, bait, and refreshments on your way to world-class fishing and diving. Residents also enjoy The Bent Prop, a beloved waterfront restaurant offering a true taste of the Keys lifestyle.

21090 5th Ave, Cudjoe

$2,800,000

SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

4 Beds ⋅ 3 Baths ⋅ 619615 MLS

SPECIAL DAILY TRANSIENT LICENSE!!! Experience one of the Lower Keys' rarest offerings at 21640 Overseas Highway,an extraordinary 1.2 acre open-water estate with panoramic ocean views, resort style amenities, and true investment upside. Opportunities like this almost never come to market from Key West to Summerland. With 3,286 sq ft per appraisal, this 4-bedroom waterfront residence delivers the scale, privacy, and setting luxury buyers search for but rarely find. From the moment you enter, the home is designed around the water. Expansive living areas, soaring ceilings, and oversized windows frame endless blue views while natural light fills the interior. The spacious layout offers multiple entertaining zones, generous bedroom suites, and the kind of footprint that allows a buyer to enjoy immediately or elevate into a signature Keys showplace. Outside is where this property separates itself from nearly everything else on the market. The massive parcel creates room to breathe, entertain, and enjoy waterfront living on a level almost impossible to replicate today. A private pool, sandy beach area, dockage, mature tropical grounds, and open-water backdrop combine to create a true resort atmosphere. Sunrise coffee, sunset cocktails, paddleboarding, boating, and stargazing all happen from your own backyard. Under the home, an immense garage / storage / workshop space offers rare functionality for collectors, boating gear, vehicles, trailers, hobbies, or business use. Very few waterfront homes in the Keys offer this level of usable enclosed space. For investors, this property's transient rental license potential is a major value driver. Large open-water estates with acreage and premium amenities command exceptional demand in the vacation market. With the right presentation and management plan, this is the type of asset that can serve as both a personal retreat and a high-performing income property. Lets take a look!!!

21640 Overseas Hwy, Cudjoe

$2,699,999

Welcome to one of Cudjoe Gardens' most desirable waterfront addresses Built in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and remarkably affordable insurance costs. One of the property's most impressive features is its combined flood, wind, and homeowners insurance, totaling less than $5,500 per year--an extraordinary value for a waterfront home of this caliber in the Florida Keys. Designed with boaters in mind, the property offers approximately 100 feet of concrete dockage along a wide flow-through canal with deep-water access and quick routes to both the Gulf of Mexico and Atlantic Ocean. Two boat lifts, including a 10,000-pound and 14,000-pound lift, provide ample capacity for multiple vessels, making it easy to keep your boats protected and ready for your next fishing, diving, or boating adventure.The backyard is a private tropical retreat centered around a stunning 50-foot resort-style swimming pool heated/chilled Whether you're swimming laps, entertaining guests, or simply relaxing in the Florida sunshine, this outdoor space was designed to impress. A custom tiki bar, outdoor kitchen, waterfront pergola, and expansive entertaining decks create the perfect setting for hosting family and friends while enjoying beautiful waterfront views. Inside, the open-concept floor plan is filled with natural light and designed to capture water views throughout the home. High ceilings, spacious living areas, and modern coastal finishes create an atmosphere that is both elegant and comfortable. The seamless transition between indoor and outdoor living makes this home ideal for embracing the laid-back Florida Keys lifestyle.Located within the sought-after Cudjoe Gardens community, and nearby marina

4 Beds ⋅ 3 Baths ⋅ 620277 MLS

Welcome to one of Cudjoe Gardens' most desirable waterfront addresses Built in 2018, 20833 4th Avenue West is an exceptional CBS waterfront estate offering 4 bedrooms, 3 bathrooms, and more than 2,400 square feet of thoughtfully designed living space. Perfectly positioned on an oversized waterfront lot, this home combines outstanding boating amenities, resort-style outdoor living, and remarkably affordable insurance costs. One of the property's most impressive features is its combined flood, wind, and homeowners insurance, totaling less than $5,500 per year--an extraordinary value for a waterfront home of this caliber in the Florida Keys. Designed with boaters in mind, the property offers approximately 100 feet of concrete dockage along a wide flow-through canal with deep-water access and quick routes to both the Gulf of Mexico and Atlantic Ocean. Two boat lifts, including a 10,000-pound and 14,000-pound lift, provide ample capacity for multiple vessels, making it easy to keep your boats protected and ready for your next fishing, diving, or boating adventure.The backyard is a private tropical retreat centered around a stunning 50-foot resort-style swimming pool heated/chilled Whether you're swimming laps, entertaining guests, or simply relaxing in the Florida sunshine, this outdoor space was designed to impress. A custom tiki bar, outdoor kitchen, waterfront pergola, and expansive entertaining decks create the perfect setting for hosting family and friends while enjoying beautiful waterfront views. Inside, the open-concept floor plan is filled with natural light and designed to capture water views throughout the home. High ceilings, spacious living areas, and modern coastal finishes create an atmosphere that is both elegant and comfortable. The seamless transition between indoor and outdoor living makes this home ideal for embracing the laid-back Florida Keys lifestyle.Located within the sought-after Cudjoe Gardens community, and nearby marina

20833 W 4th Ave, Cudjoe

$2,499,000

Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and effortless waterfront living, the 2,739-square-foot home features 4 bedrooms, a spacious open-concept great room, bamboo flooring, impact windows and doors, and a durable metal roof. The chef's kitchen is the heart of the home, offering a large center island, stainless steel appliances, abundant cabinetry, and a wine refrigerator and is the perfect gathering place for entertaining family and friends. Step outside to a beautifully landscaped tropical setting with expansive screened lanai overlooking the water and an 82-foot dock complete with boat lift and kayak launch. Whether you're heading offshore for a day of fishing, enjoying sunset cruises, or simply relaxing by the water, this property delivers the Keys lifestyle you've been dreaming about. The 2- car Garage offers plenty of parking and room for all or your toys while the oversized double lot provides privacy and space to enjoy the outdoors while taking advantage of the home's unique corner-like waterfront setting. Located in one of the Lower Keys' most desirable boating communities, Cudjoe Gardens offers deep-water canals capable of accommodating larger inboard vessels, plus convenient access to a full-service marina with fuel, bait, boat ramp, refreshments, and a waterfront restaurant. Just 20 minutes from Key West, you'll enjoy world-class dining, entertainment, and island living while returning home to a peaceful waterfront retreat.

4 Beds ⋅ 2 Baths ⋅ 620071 MLS

Experience the ultimate Florida Keys boating lifestyle at this exceptional waterfront residence in prestigious Cudjoe Gardens. Situated on a rare double lot encompassing 16,827 square feet, this CBS-built, ground-level home sits above the flood plain and offers approximately 225 feet of waterfront on two sides, deep-water dockage, and remarkably quick ocean access. Designed for comfort and effortless waterfront living, the 2,739-square-foot home features 4 bedrooms, a spacious open-concept great room, bamboo flooring, impact windows and doors, and a durable metal roof. The chef's kitchen is the heart of the home, offering a large center island, stainless steel appliances, abundant cabinetry, and a wine refrigerator and is the perfect gathering place for entertaining family and friends. Step outside to a beautifully landscaped tropical setting with expansive screened lanai overlooking the water and an 82-foot dock complete with boat lift and kayak launch. Whether you're heading offshore for a day of fishing, enjoying sunset cruises, or simply relaxing by the water, this property delivers the Keys lifestyle you've been dreaming about. The 2- car Garage offers plenty of parking and room for all or your toys while the oversized double lot provides privacy and space to enjoy the outdoors while taking advantage of the home's unique corner-like waterfront setting. Located in one of the Lower Keys' most desirable boating communities, Cudjoe Gardens offers deep-water canals capable of accommodating larger inboard vessels, plus convenient access to a full-service marina with fuel, bait, boat ramp, refreshments, and a waterfront restaurant. Just 20 minutes from Key West, you'll enjoy world-class dining, entertainment, and island living while returning home to a peaceful waterfront retreat.

21023 2nd Ave, Cudjoe

$2,299,995

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.

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

$2,195,000

TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

5 Beds ⋅ 3 Baths ⋅ 620325 MLS

TRANSIENT LICENSE * NIGHTLY RENTALS* PROVEN RENTAL INCOME* IDEAL 1031 EXCHANGE OPPORTUNITY Casa De Las Palmas Rarely does a Florida Keys property combine proven income, privacy, and future potential like this. Situated on nearly two acres spanning four lots, this unique compound offers a coveted transient license allowing nightly rentals and a well-established vacation rental business with a strong history of performance. Historically generating over $200,000 annually, with recent projections ranging from $250,000 to $300,000, this is an outstanding opportunity for investors, vacation rental operators, or buyers seeking a premier 1031 Exchange replacement property. More than just a rental property, this is a proven income-producing asset with an established guest base, and delivering the authentic Florida Keys experience that visitors seek. Rather than starting from scratch, a new owner can step into a property with a successful operating history and demonstrated demand. The property features a 4-bedroom, 2-bath main residence, relaxing pool, expansive outdoor living areas, and a separate concrete guest structure complete with bedroom, bath, and kitchenette. Fully fenced with two private entrances, the grounds offer exceptional privacy, abundant tropical landscaping, fruit trees, palms, and ample space for RVs, boat trailers, and recreational equipment. Over 100 Palm trees Future upside may exist through additional development opportunities, expansion of the existing compound, or further enhancement of the guest experience, subject to buyer verification and applicable regulations. Properties offering a transient license, multiple lots, substantial acreage, proven income, and future potential are increasingly rare in today's Florida Keys market. Whether you're seeking a high-performing vacation rental, a strategic 1031 Exchange acquisition, or a private Florida Keys retreat, this property is positioned to deliver value and Solid ROI from day one.

125 Colson Dr, Cudjoe

$2,099,000

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.

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

$2,060,000

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.

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

$2,000,000

Commercial or Mixed Use Development, 8 contiguous parcels with a total of 1.56 Acres with 240 feet of US1 frontage. One parcel includes a 745sf retail/service structure. Zoned SC which allows for 18 affordable units per acre, verify with the County for specifics.

583921 MLS

Commercial or Mixed Use Development, 8 contiguous parcels with a total of 1.56 Acres with 240 feet of US1 frontage. One parcel includes a 745sf retail/service structure. Zoned SC which allows for 18 affordable units per acre, verify with the County for specifics.

22732 Overseas Hwy, Cudjoe

$1,799,000

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!

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

$1,799,000

Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock, direct ocean access via a 60-ft wide canal, and proximity to the neighborhood marina. Enter through a covered entry into an airy Great Room with soaring ceilings and newly installed marble-look tile, giving the space a crisp, clean feel. The spacious kitchen features warm wood cabinetry, generous counter space, and casual bar seating—ideal for entertaining. A primary suite retreat includes his-and-hers closets and a spa-like bath, plus an adjacent den that offers flexibility as a 4th bedroom, home office, or studio. The attached 2-car Garage allows plenty of space for all your toys. The tropically landscaped yard with shady palms and pretty brick drive boasts picturesque curb appeal. Cudjoe Gardens offers a full-service marina, fueling station, and a charming canal-side restaurant—all moments from your front door. Just 20 miles to Key West, this is an exceptional opportunity to enjoy world-class boating and tropical elegance without stairs or compromise.

3 Beds ⋅ 3 Baths ⋅ 618500 MLS

Tucked into the sought-after waterfront enclave of Cudjoe Gardens, 51 Sawyer Drive offers the rarest of Florida Keys luxuries: ground-level living above base flood elevation. Built with integrity from solid concrete block and enhanced by Pella windows and a standing seam metal roof, this residence delivers peace of mind and timeless appeal. Boaters will appreciate the 80-foot concrete dock, direct ocean access via a 60-ft wide canal, and proximity to the neighborhood marina. Enter through a covered entry into an airy Great Room with soaring ceilings and newly installed marble-look tile, giving the space a crisp, clean feel. The spacious kitchen features warm wood cabinetry, generous counter space, and casual bar seating—ideal for entertaining. A primary suite retreat includes his-and-hers closets and a spa-like bath, plus an adjacent den that offers flexibility as a 4th bedroom, home office, or studio. The attached 2-car Garage allows plenty of space for all your toys. The tropically landscaped yard with shady palms and pretty brick drive boasts picturesque curb appeal. Cudjoe Gardens offers a full-service marina, fueling station, and a charming canal-side restaurant—all moments from your front door. Just 20 miles to Key West, this is an exceptional opportunity to enjoy world-class boating and tropical elegance without stairs or compromise.

51 Sawyer Dr, Cudjoe

$1,399,000

Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you to your deeded dock equipped with water and electric, giving you effortless ocean access just steps from your door. The interior is light, open, and welcoming, with a focus on bringing the outside in. Enjoy a wraparound porch that frames panoramic views of the Atlantic, while inside you'll find an open floor plan with tile floors and island-inspired charm throughout. The entire second level is dedicated to a spacious primary suite, complete with a cozy sitting area overlooking the sea. Cudjoe Cove offers low HOA dues, a resort-style pool with waterfall, and trailer storage. Just 20 minutes from Key West and moments from restaurants, a marina, and conveniences — this home is ideal as a full-time residence, a second home, or a vacation getaway.

3 Beds ⋅ 2 Baths ⋅ 618382 MLS

Discover a serene escape nestled in the heart of the Lower Florida Keys. Located in Cudjoe Cove, a boutique gated community of just nine homes, this 3-bedroom, 2-bath conch cottage offers unbeatable views and direct access to the ocean. Built of durable concrete with a standing seam metal roof and impact-rated windows, the home is designed for coastal resilience. A long tropical walkway leads you to your deeded dock equipped with water and electric, giving you effortless ocean access just steps from your door. The interior is light, open, and welcoming, with a focus on bringing the outside in. Enjoy a wraparound porch that frames panoramic views of the Atlantic, while inside you'll find an open floor plan with tile floors and island-inspired charm throughout. The entire second level is dedicated to a spacious primary suite, complete with a cozy sitting area overlooking the sea. Cudjoe Cove offers low HOA dues, a resort-style pool with waterfall, and trailer storage. Just 20 minutes from Key West and moments from restaurants, a marina, and conveniences — this home is ideal as a full-time residence, a second home, or a vacation getaway.

21250 Conch Dr, Cudjoe

$1,399,000

Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while embracing modern luxury. Impact doors and windows, wide-plank engineered wood flooring, and an updated chef's kitchen with gas range create interiors that are both stylish and functional—ideal for relaxed living and elegant entertaining. The serene Primary Suite is a private sanctuary, featuring expansive picture windows that frame stunning views of the home's massive, newly refurbished waterfront pool, evoking a true resort-style experience. Designed for the boating enthusiast, the property offers deep-water dockage on a flow through canal with a concrete dock and 10,000-lb boat lift, providing effortless access to open water. A whole-house generator with automatic transfer switch ensures uninterrupted comfort and peace of mind year-round. Located within one of the Keys' most desirable waterfront neighborhoods, residents enjoy access to the Cudjoe Gardens Marina a full-service marina with fuel, bait, refreshments, and boat ramp, along with a beloved Bent Prop waterfront restaurant—all just moments from home This is a rare opportunity to own a historically significant, architecturally distinctive residence that seamlessly blends mid-century design, modern upgrades, and an unparalleled waterfront lifestyle.

3 Beds ⋅ 2 Baths ⋅ 617709 MLS

Originally built as the developer of Cudjoe Gardens personal residence, this exceptional Mid-Century Modern waterfront Turn-Key home captures the effortless glamour of Palm Springs design blended with the laid-back sophistication of the Florida Keys. Offered fully furnished with 3 Bedrooms and 2 Baths, the residence has been beautifully remodeled with meticulous attention to detail, honoring its architectural roots while embracing modern luxury. Impact doors and windows, wide-plank engineered wood flooring, and an updated chef's kitchen with gas range create interiors that are both stylish and functional—ideal for relaxed living and elegant entertaining. The serene Primary Suite is a private sanctuary, featuring expansive picture windows that frame stunning views of the home's massive, newly refurbished waterfront pool, evoking a true resort-style experience. Designed for the boating enthusiast, the property offers deep-water dockage on a flow through canal with a concrete dock and 10,000-lb boat lift, providing effortless access to open water. A whole-house generator with automatic transfer switch ensures uninterrupted comfort and peace of mind year-round. Located within one of the Keys' most desirable waterfront neighborhoods, residents enjoy access to the Cudjoe Gardens Marina a full-service marina with fuel, bait, refreshments, and boat ramp, along with a beloved Bent Prop waterfront restaurant—all just moments from home This is a rare opportunity to own a historically significant, architecturally distinctive residence that seamlessly blends mid-century design, modern upgrades, and an unparalleled waterfront lifestyle.

51 Drost Dr, Cudjoe

$1,299,000

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!

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

$1,270,000

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.

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

$1,247,500

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.

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

$1,150,000

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!

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

$949,000

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.

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

$895,000

If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and Bahama shutters, this home is virtually maintenance-free and hurricane-resistant. Clean, solid, and move-in-ready, the only thing it needs is a little cosmetic updating to reflect your personal style. Come see it today and imagine making it your own.

3 Beds ⋅ 2 Baths ⋅ 620163 MLS

If you've been looking for the home you can live in while adding your personal touches to, you have found it. With 60' of composite dock on a 40' wide canal in a 3' control depth neighborhood, you can keep your boat right at your back door. This well-maintained home is in excellent condition and has been lovingly cared for by the original owner. With its metal roof, 240 mph vinyl siding, and Bahama shutters, this home is virtually maintenance-free and hurricane-resistant. Clean, solid, and move-in-ready, the only thing it needs is a little cosmetic updating to reflect your personal style. Come see it today and imagine making it your own.

135 Tortuga Ln, Cudjoe

$879,000

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

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

$875,000

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 *

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

$875,000

Attention Investors and business owners! Unique opportunity to purchase commercial building in Cudjoe Key with two established business incomes as well as a residential rental income. The apartment is a two bedroom, one bath space with current lease in place. The office space includes a half bath and has a month to month tenant. The owner is occupying the outdoor space as well as the downstairs storage and would like to lease back from the new owner. This rare opportunity has incredible potential in a prime location. Please do not disturb business. Call today to take a tour.

2 Beds ⋅ 2 Baths ⋅ 617266 MLS

Attention Investors and business owners! Unique opportunity to purchase commercial building in Cudjoe Key with two established business incomes as well as a residential rental income. The apartment is a two bedroom, one bath space with current lease in place. The office space includes a half bath and has a month to month tenant. The owner is occupying the outdoor space as well as the downstairs storage and would like to lease back from the new owner. This rare opportunity has incredible potential in a prime location. Please do not disturb business. Call today to take a tour.

22814 Overseas Hwy, Cudjoe

$819,500

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.

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

$799,000

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.

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

$799,000

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.

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