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$898,000
2 Beds 2 Baths 620526 MLS
Just 0.3 miles from Sombrero Beach, this elevated 2BD/2BA Marathon home offers a prime location, strong weekly rental potential and abundant flexible space. Set on a spacious lot with room to add a pool, the home features vaulted tongue-and-groove ceilings, tile flooring, and two additional rooms downstairs ideal for an office, studio, game room or storage, plus plenty of covered space for parking and recreational gear. The tropical backyard includes mature landscaping, fruit trees, an herb garden, fire pit and custom covered bar and grilling area. A nearby comparable pool-home generated over $115K in gross weekly rental income in 2025, highlighting the rental appeal of this highly sought-after beachside location. The property also offers reasonable insurance costs, adding to its investment appeal. This property is ideal for buyers seeking a beachside home, investment opportunity or both. Enjoy easy access to the beach, boating, dining, and all that Marathon has to offer! Rental income is not guaranteed; buyers should verify regulations/requirements.

422 Calle Limon, Marathon

$295,000
3 Beds 3 Baths 620525 MLS
Experience the Florida Keys with this fractional ownership opportunity at Fisherman's Cove, a private residence club set along Blackwater Sound in Key Largo. This spacious residence offers approximately 2,300 square feet, featuring three bedrooms and three full bathrooms. The recently updated interior showcases a clean coastal-modern design with subtle island touches. A fully equipped kitchen with bar seating opens to the main living area, while a private balcony provides beautiful waterfront views. Owners enjoy access to premium amenities, including a rooftop owners' deck, resort-style pool with three private cabanas, and community boats such as a 26' Sea Fox and 24' Contender. Concierge and housekeeping services ensure a seamless stay. Conveniently located above Jimmy Johnson's Big Chill, with dining and entertainment just steps away. Ownership includes flexible use, typically 5-7 weeks per year, with additional time based on availability. This is a private ownership club and is not available for rental. All privileges are reserved for owners only. Interest 2 in Unit 1 is being conveyed as a deed to the property. Seller Financing Available!

104000 Overseas Hwy Unit 1 - 2, Key Largo

$699,000
2 Beds 2 Baths 620522 MLS
A rare two story CBS townhouse condo with both open water views and an assigned boat slip overlooking scenic Boot Key Harbor in desirable and quiet Sombrero area neighborhood. Located adjacent to Sombrero golf course. Deep water and boating access to Atlantic Ocean or Gulf. Remodeled lower level has open concept, modern kitchen with island and Corian countertops. All oak wood cabinets, ceramic tile flooring, stainless appliances, double oven, on demand water heater, new bathroom. All new plumbing and electric. Upstairs bathroom also completely remodeled, new tiled shower, Kohler fixtures, guitar extension counter, storage. Laundry area is on second level, Bosch washer/dryer. Class A rated MD shutters. Primary bedroom has a private screened balcony with harbor views. Lower level also offers a screened porch. Small 8-unit complex, shared heated pool with seating and BBQ grilling area, immaculately maintained grounds. Centrally located near restaurants, entertainment, grocery, post office, and short distance to beautiful public Sombrero Beach. Rentals allowed once per calendar year with a minimum of 30 days, maximum long term 1 year: option to renew with board approval. Quarterly condo association fee includes Building Exterior Maintenance, Common Area Maintenance, Condo Association Insurance, Exterior & Unit Interior Exterminating and Reserve Account contributions. Off street parking, 2 dedicated parking spots directly in front of the condo.

307 Sombrero Blvd Unit 2, Marathon

$2,949,000
6 Beds 4 Baths 620520 MLS
Welcome to your waterfront retreat in the heart of Key Colony Beach. Perfectly positioned on a deep-water canal with 75' of concrete dockage, this spacious 6-Bed, 4-Bath residence offers the ideal blend of island living, boating convenience, and exceptional investment potential. Designed to comfortably accommodate family and guests, the property features a unique floor plan with a 4-Bedroom, 2-Bath main residence and an attached ground level 2-Bedroom, 2-Bath guest quarters, providing flexibility for multi-generational living, entertaining, or maximizing rental income. Soaring ceilings and abundant natural light enhance the open living area, while impact-rated windows and doors provide peace or mind. A highlight of the home is the expansive screened porch overlooking the sparkling pool and tranquil canal. Outside, the resort-style backyard is built for enjoying the Florida Keys lifestyle. Relax in the heated pool and spa, soak up the sun on multiple lounge areas, or dine outdoors while watching the boats cruise by. The expansive patio offers plenty of seating for gathering with family and friends, while the 75-foot concrete seawall accommodates boats up to approximately 35 feet. From your dock, you'll enjoy quick boating access to the Atlantic Ocean in just minutes, with nearby Vaca Cut providing convenient access to the Gulf. Additional features include a garage, ample storage, low-maintenance tropical landscaping, and plenty of room for everyone to enjoy. Located in the sought-after island community of Key Colony Beach, you're just moments from waterfront dining, golf, pickleball, walking paths, Sunset Park, marinas, and Middle Keys attractions. Whether you're searching for a luxury primary residence, second home, or an established investment property, this canal-front oasis checks every box.

420 11th St, Key Colony

$1,199,000
2 Beds 4 Baths 620515 MLS
Welcome to Seaside Residences, one of Key West's most sought-after gated communities. This beautifully updated three-story townhome is one of the largest residences in the community, offering 2 bedrooms, 3.5 bathrooms, 1,824 square feet of thoughtfully designed living space, making it the second-largest property in Seaside Residences. A private elevator services all three levels, providing both comfort and convenience. Enjoy the best island living with three private balconies offering beautiful sunrise and sunset views, plus a private rooftop deck perfect for relaxing, entertaining, or soaking up the Florida sunshine. The ground level features a private garage, laundry area, half bath, and a spacious outdoor patio complete with a tranquil fountain and fire pit--an ideal space for gathering with family and friends. The second level offers a spacious primary suite with an ensuite bath featuring dual vanities and a large walk-in shower, while the guest bedroom enjoys its own private full bath. The top floor showcases an open-concept living, dining, and kitchen area filled with abundant natural light. The kitchen features rich wood cabinetry, granite countertops, stainless steel appliances, generous pantry space, and an ideal layout for both everyday living and entertaining. Recent upgrades include a new air conditioning system, new water heater, and impact-resistant windows and doors throughout, providing peace of mind, energy efficiency, and storm protection. Residents enjoy exceptional community amenities including a resort-style pool, fitness center, and the convenience of building insurance covered through the HOA. Ideally located just steps beaches, Old Town Key West, world-class dining, shopping, marinas, and local attractions, this property also allows short-term rentals, making it an outstanding opportunity as a full-time residence, luxurious vacation home, or exceptional income-producing investment.

33 Seaside S Ct, Key West

$2,250,000
3 Beds 2 Baths 620513 MLS
Welcome to Your Slice of Paradise in the Florida Keys Discover the perfect blend of island charm, waterfront living, and investment potential in this fully furnished, turnkey home in the heart of Marathon. Whether you're searching for a vacation getaway, a full-time residence, or a proven income-producing property, this exceptional home offers it all. Property Highlights 3 Bedrooms | 2 Bathrooms Bonus room/flex space perfect for guests, a home office, or additional living space Fully furnished and move-in ready Excellent vacation rental history 17,000 lb boat lift 150 feet of seawall Private tiki hut for relaxing and entertaining Short walk to Sombrero Beach Just a 3-minute idle boat ride to the open Atlantic Ocean Minutes from the iconic Sombrero Key Lighthouse Exceptional boating access with quick ocean access Beautiful outdoor living spaces designed to embrace the Florida Keys lifestyle Wake up to gentle ocean breezes, spend your days boating or relaxing on the beach, and unwind beneath the tiki hut as the sun sets. With outstanding boating access, a sought-after location, and a successful vacation rental history, this waterfront retreat is the perfect opportunity to experience the very best of island living. Live like you're on vacation every day in the beautiful Florida Keys.

64 Tingler Ln, Marathon

$899,000
3 Beds 2 Baths 620512 MLS
Bring your water toys & experience island living in this newly built waterfront home in Summerland Key. The residence offers 3 bedrooms 2 bathrooms spacious modern design & trim. A durable metal roof, Hardie-board siding, impact windows and doors. Enjoy relaxing or entertaining on the covered porch, step out on the composite dock and be on the open ocean or Gulf in minutes, perfect for boating, fishing and sunset cruses. Keys biking trail steps away. Great local restaurants, convenient local island grocery store. Private Summerland Key Airstrip. Centrally located between Marathon and Key West, this property combines modern construction, waterfront convenience, low maintenance and easy access to both Keys' amenities. Ideal for a vacation retreat or full time home. Schedule your private showing today.

23940 Overseas Hwy, Summerland

$2,350,000
3 Beds 3 Baths 620442 MLS
Welcome to your slice of paradise in the village of Islamorada! This solid concrete waterfront home was completely updated in 2007 including seawall, all plumbing and electrical and new concrete roof engineered to add another floor. The home has 3 bedrooms, 3 bathrooms and 75 feet of deep water dockage in one of the most desirable boating locations in the Florida Keys. Built with impact windows and doors, this home provides peace of mind while embracing the relaxed island lifestyle. Situated just one house in from Florida Bay, you'll enjoy breathtaking sunset views nearly every evening. Located just moments from Tavernier Creek, you'll have quick and convenient access to the Atlantic Ocean, making it the perfect location for anglers, boaters, and water enthusiasts alike. Inside the home offers comfortable living with 2/2 upstairs with walk in closets, high ceilings and crown molding and a large screen porch to watch sunsets. A spiral staircase leads to a 1/1 downstairs with kitchen and open living area. Plenty of storage and work area downstairs and a garage. Convenience is unmatched with a prime location close to schools, grocery stores, movie theaters, restaurants, shopping, and all the amenities that make island living so enjoyable. Whether you're searching for a full-time residence, a vacation home, or an investment in one of the Keys' most sought-after communities, this waterfront gem offers the perfect combination of location, boating access, quality construction, and endless potential.

239 Plantation Ave, Tavernier

$599,999
2 Beds 2 Baths 620509 MLS
Welcome to Bonefish Towers - the tallest building in the Florida Keys! This rare 1st -floor unit offers breathtaking panoramic views of both the Atlantic Ocean and the Bay, creating a front-row seat to spectacular sunsets, passing boats, and the beauty of Key Colony Beach. Inside, you'll find a spacious 2-bedroom, 2-bathroom layout featuring two screened-in porches - perfect for morning coffee or evening cocktails with a view. The open floor plan is filled with natural light and includes floor-to-ceiling sliding glass doors, two large walk-in closets, and a private en-suite in the primary bedroom. Bonefish Towers is a full-service oceanfront community with resort-style amenities including: Heated pool with tiki hut and pool house Tennis and pickleball courts, Brand-new fitness center, Billiards and recreation room with big screen TV, Sauna and beach area, Fishing pier with fish cleaning stations, BBQ grills and outdoor dining spaces, Marina and paddleboard-friendly canal, 24-hour security and on-site management. With ample parking, low HOA fees (includes insurance, cable, internet, water, parking, and exterior maintenance), and a prime location, this unit is ideal as a primary home, vacation getaway, or Investment property. Don't miss your chance to own a slice of paradise at Bonefish Towers - the only high-rise in the Keys!

2000 Coco Plum Dr Unit 106, Marathon

$1,695,000
4 Beds 5 Baths 620508 MLS
**Waterfront Key Largo Retreat with Direct Ocean Access** Experience the best of Florida Keys living in this exceptional canal-front CBS home featuring a durable concrete roof, over 3,100 sq. ft. of living space, and direct ocean access. Perfectly positioned for boating, fishing, diving, and water adventures, this property offers the ideal blend of comfort, convenience, and island lifestyle -- with easy mainland access for commuting. The spacious two-story residence is designed for both everyday living and entertaining. The second floor main level features an open-concept layout connecting the living room, dining area, and kitchen, creating a welcoming space for gatherings with family and friends. The upper level includes a beautifully appointed new primary suite with a spacious bedroom and private bath, along with a guest bedroom, guest bathroom, and a versatile office/multi-purpose room with an additional full bath. A permitted first-floor addition, completed in 2001, provides added flexibility with two bedrooms, one and a half baths, and a garage -- ideal for guests, extended family, or additional living space. Boaters will appreciate the 60-foot split-level concrete dock with step-down access, perfect for kayaks, paddle boards, and lower-profile vessels. The property also offers ample parking for boats, RVs, and trailers, making it easy to enjoy everything the Florida Keys has to offer. Wake up, step outside, and head straight to the water for a morning paddle, fishing excursion, dive adventure, or sunset cruise. This is your opportunity to own a true Key Largo waterfront retreat and embrace the lifestyle you've been waiting for.

1210 Cactus St, Key Largo

$799,000
3 Beds 1 Baths 620504 MLS
This newly remodeled 3-bedroom, 1-bathroom home is perfectly positioned on a spacious lot in the heart of Big Pine Key, offering 10,275 sq ft of land and an incredible 75 feet of waterfrontage, with a concrete seawall. With quick access to the ocean via Spanish Harbor Channel, this is a boater's dream come true. Inside, enjoy peace of mind with impact-rated windows and doors, a sturdy metal roof, and stylish modern finishes throughout. Outside, there's plenty of room to expand, entertain, or simply relax and soak in the serene Keys lifestyle. Located just minutes from shopping, dining, and Big Pine Community Park, this home combines privacy and convenience in one of the Lower Keys' most desirable neighborhoods.

550 Pine Ln, Big Pine

$1,450,000
2 Beds 3 Baths 620503 MLS
Introducing 8401 Gulf of Mexico Blvd #8401, an exceptional waterfront penthouse with Boat Slip #23, located in the prestigious Seawatch community of Marathon, Florida. Renovated in 2023 and meticulously maintained since, this top floor residence offers an impressive combination of comfort, style, boating access and one of the most captivating open water views in the community. From the moment you step inside, expansive impact windows frame breathtaking Gulf views and fill the living space with natural light. The spacious layout features two generous suites, an open living and dining area and a clean coastal feel designed for relaxed Florida Keys living. The 2023 renovation included thoughtful updates to the kitchen, bathrooms, flooring and interior finishes. The kitchen offers updated cabinetry and appliances, while the remodeled bathrooms feature updated tile and showers, creating a move in ready residence that has been carefully improved and maintained. Seawatch is known for one of the most impressive amenity packages in the Middle Keys, including a gated entrance, marina, resort style pool and spa, cabanas, fitness center, clubhouse/event room, tennis & pickleball courts, elevators, tropical landscaping, natural habitat areas, lake and generous open space rarely found in a condo community. Complete with protected dockage and a premier waterfront setting, this Seawatch penthouse is ideal as a full time residence, seasonal retreat, or low maintenance Florida Keys getaway. Enjoy boating, views, privacy and resort style amenities all in one of Marathon's most desirable waterfront communities.

8401 Gulf Of Mexico Blvd Unit #401, Marathon

$849,000
3 Beds 3 Baths 620501 MLS
Adorable 2 bed ,1.5 bath single family home in Pearlman neighborhood with separate 1-1 cottage anchored by a picturesque Royal Poinciana tree out front! Features a large (16 X 15) screen room between the main house & the cottage. You can pass from the main house thru the screened room into the cottage & still be under roof. Cottage does have its own separate entrance. Use the cottage as an extension of the main house or as separate living space, she-shed, man-cave, studio, work out room or home office. Roof replaced in 2016. Exposed beam ceilings in kitchen and dining areas. For those familiar with the 'Sunshine Homes' in KW, you know they were built with crawl spaces between the ground & the floor, taller attics w/ pull-down stairs, beautiful hard wood floors & asbestos siding. Most of main house still has original hard wood floors & the cottage has bamboo flooring. Sellers say interior of house did not flood during Wilma. 3712 Duck affords you yard space, room for pool, carport with additional off-street parking & one of KW's most desirable New Town neighborhoods. Convenient location is close to schools, shopping, theaters, medical offices, ball fields, beach, airport, golf course & hospital. Just a short ride into Old Town & world-famous Duval St.. Make your next home at 3712 Duck Ave!

3712 Duck Ave, Key West

$6,200,000
5 Beds 5 Baths 620499 MLS
Don't miss this rare and exceptional opportunity to have your dream waterfront masterpiece begin construction in 2026! Located in the prestigious, gated community of Shark Key, 36 Cannon Royal is an extraordinary west-facing lot that spans nearly 14,500 square feet and boasts approximately 130 feet of waterfront, delivering breathtaking sunset views over the Gulf waters. The sale of this property includes the completed construction of a 4,624 square-foot single family residence in accordance with the approved architectural plans and all associated permits. This thoughtfully designed 5-bedroom, 4.5-bath home features an elevator, a high-end chef's kitchen, loft, outdoor shower, fire pit, outdoor kitchen, and multiple porches/balconies that set the tone for a seamless indoor-outdoor lifestyle. The expansive fifty foot resort-style pool with sun ledge completes the vision of perfectly tailored island life. Additional conveniences include a two car garage, ample storage, and large covered patio located on the ground level. 36 Cannon Royal is a fully realized, ready-to-build waterfront estate offering luxurious coastal living, impact-rated construction, and peace of mind without compromising comfort or design. Shark Key residents enjoy exclusive amenities including a clubhouse, private beach, swimming lagoon, and pickleball/tennis courts- just minutes away from the world-class dining, arts, and entertainment of iconic Key West. Current architectural plans of 36 Cannon Royal are pending review by Shark Key ARB.

36 Cannon Royal Dr, Shark Key

$2,500,000
620498 MLS
Don't miss this rare and exceptional opportunity to build your dream home in the prestigious, gated community of Shark Key —without the wait! 36 Cannon Royal is an extraordinary west-facing lot that spans nearly 14,500 square feet and boasts approximately 130 feet of waterfront, delivering breathtaking sunset views over the Gulf waters. The sale of this vacant lot conveys the completed engineered architectural plans for a 4,624-square-foot single-family residence, along with a coveted ROGO permit and building permits already secured and in hand. The thoughtfully designed 5-bedroom, 4.5-bath residential blueprint features an elevator, a high-end chef's kitchen, loft, outdoor shower, fire pit, outdoor kitchen, and multiple porches/balconies that set the tone for a seamless indoor-outdoor lifestyle. The expansive fifty foot resort-style pool with sun ledge completes the vision of perfectly tailored island life. Additional conveniences include a two car garage, ample storage, and large covered patio on the ground level. This is far more than vacant land—it is a fully realized, ready-to-build masterpiece for luxurious coastal living. Shark Key residents enjoy exclusive amenities including a clubhouse, private beach, swimming lagoon, and pickleball/tennis courts- just minutes away from the world-class dining, arts, and entertainment of iconic Key West. Current architectural plans of 36 Cannon Royal are pending review by Shark Key ARB.

36 Cannon Royal Dr, Shark Key

$899,000
2 Beds 2 Baths 620490 MLS
Key West Lifestyle awaits at this rare waterfront opportunity in the exclusive gated community at 28 Jade Drive. One of only eight resort-style townhomes, this beautifully maintained 2-bedroom, 2-bath residence offers an exceptional waterfront setting with protected seawall and boat dockage on one side and breathtaking open bay views on the other. Enjoy spectacular sunrises, refreshing ocean breezes, and direct boating access from your private dock. Community amenities include a beautiful waterfront swimming pool and a private beach, creating the perfect island retreat. The thoughtfully designed floor plan offers comfortable living spaces, abundant natural light, and seamless indoor-outdoor living. Additional features include covered parking for two vehicles, a secure gated entrance, and a peaceful, private setting. Just a 10-minute drive to Key West, beaches, dining, shopping, and world-famous attractions. Opportunities to own in this intimate eight-unit waterfront community are exceptionally rare, making this an outstanding choice for buyers seeking the ultimate Key West waterfront lifestyle.

28 Jade Dr Unit 1, Big Coppitt

$14,995,000
11 Beds 9 Baths 620489 MLS
Welcome to Morton Manor, an exceptional gulf-side waterfront estate set on 2.82 private acres where luxury, privacy, and resort-style living come together in this extraordinary Florida Keys compound. Encompassing 8,515 sq. ft. of living space, this property features a 5-bedroom, 4.5 bath CBS main residence accompanied by two detached guest homes and a garage apartment, offering a total of 11 bedrooms and 8.5 baths designed to comfortably accommodate family and guests alike. The main home showcases an open-concept floor plan with expansive living and dining areas, two wet bars, elevator access, multiple laundry areas, and spacious guest accommodations, creating an ideal setting for both everyday living and large-scale entertaining. The detached bungalows and garage apartment provide additional flexibility for extended family, visitors, or exceptional rental opportunities while maintaining privacy throughout the estate. Impact-rated windows and doors, a durable metal roof, and quality construction provide lasting peace of mind. The outdoor amenities rival those of a private resort. Relax beside the pool, gather beneath multiple tiki huts, challenge friends to a game on the pickleball court or putting green and enjoy beautifully landscaped grounds. Boating enthusiasts will appreciate the 100' dock complete with 30-amp and 50-amp shore power, yacht dockage and 10K & 20K lb boat lifts. Positioned on the gulfside, the property offers easy access to world-class fishing, boating, snorkeling coves, sandbars, and unforgettable sunset cruises. Dining, marinas, and shopping are less than ten minutes away, and the Florida Keys Marathon International Airport is approximately 4 miles from the property for seamless private aviation access. Whether you're searching for a private family compound or an exceptional investment opportunity, Morton Manor offers a rare combination of acreage, waterfront living, luxury amenities, and versatility that is seldom found in the Florida Keys.

57733 Morton St, Marathon