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110 Ave F, Big Coppitt
$1,600,000
3 Beds ⋅ 3 Baths ⋅ 620773 MLS
Incredible and meticulously maintained waterfront oasis! Situated on an expansive 17,000+ sq. ft. lot with 100+ feet of seawall, this exceptional property offers breathtaking panoramic water views, a heated pool, and lush tropical landscaping that creates a true five-star resort experience. The bright, open-concept living and kitchen area is filled with natural light, perfectly framing the stunning waterfront setting and unforgettable sunset views. Designed for both entertaining and everyday living, the seamless indoor-outdoor flow makes the most of the home's spectacular surroundings. Privately tucked away from traffic, this peaceful retreat offers the privacy and serenity that make the Florida Keys lifestyle so special. Unlike many waterfront homes, this property provides ample space for all your boats, vehicles, and recreational toys. A spacious garage and a large detached carport offer covered storage for boats, RVs, and more, keeping them protected from the elements. Located just 10 minutes from Key West, this rare waterfront gem combines luxury, space, and functionality in one extraordinary package.

110 Ave F, Big Coppitt
2143 Yellowtail Dr, Marathon
$1,599,000
3 Beds ⋅ 2 Baths ⋅ 621615 MLS
Discover the Florida Keys lifestyle in this beautifully maintained 3-bedroom, 2-bath waterfront pool home offering 1,652 sq. ft. of living space on a wide boating canal with direct Gulf access. Designed with a unique multi-level layout, the home welcomes you with a floating staircase leading to a bright and airy Great Room featuring wood floors and impact glass doors overlooking the water. The charming Kitchen showcases soaring wood ceilings, glass-front cabinetry, stainless steel appliances and a breakfast bar opening to the Living and Dining Areas. The main level offers a guest Bedroom with wood-beamed ceilings and water views, along with a full Bath. A short staircase leads to the second Bedroom with cathedral wood ceilings and an ensuite Bath, while the uppermost level features a cozy loft-style third Bedroom. Step outside to your private waterfront retreat, where a spacious lanai surrounds the heated and chilled pool, complemented by expansive decking, new artificial turf and an outdoor shower. Boating enthusiasts will appreciate 60' of concrete dockage with a 13,000 lb. boat lift, dedicated angler's prep station and easy Gulf access for world-class fishing, diving and exploring the surrounding waters. Additional highlights include impact windows and doors, a metal roof, newer A/C, updated decking and fresh paint. A garage and generous ground-level storage provide ample space for vehicles, boating equipment and all your Keys essentials. This inviting waterfront home is ideal as a full-time residence, vacation getaway or investment opportunity in the heart of the Florida Keys.

2143 Yellowtail Dr, Marathon
97652 Overseas Highway Unit HH31, Key Largo
$1,599,000
3 Beds ⋅ 2 Baths ⋅ 621549 MLS
Exceptional open-water living in this 3-bedroom, 2-bath corner condo offering 1,685 sq. ft. of interior living space plus a 442 sq. ft. screened lanai overlooking Florida Bay. Imagine mornings on the water and Keys sunsets from this spacious outdoor living area, perfect for relaxing, dining and enjoying the tropical breezes. Inside, custom improvements include a wood-plank ceiling with decorative beam detailing and recessed lighting, leathered granite kitchen countertops, stainless appliances and a wine cooler. The redesigned primary suite features custom cabinetry and storage, a marble-look walk-in shower and a fitted dressing room/closet. Coastal-toned wood flooring adds warmth to the bedrooms, while hurricane windows and doors provide peace of mind. This furnished residence offers generous living space, privacy and elevator access. Experience Rock Harbor Club, a peaceful tropical paradise surrounded by lush landscaping. Enjoy the large sandy bayfront beach, heated and chilled pool, wooded walking trails, clubhouse, fitness facilities with saunas, tennis, pickleball, bocce and basketball. Boaters will appreciate dry-rack storage with launch and retrieval service and convenient access to the Intracoastal Waterway. It all comes together in the relaxed Florida Keys lifestyle you've been dreaming of.

97652 Overseas Highway Unit HH31, Key Largo
234 Allen Ave, Key Largo
$1,599,000
3 Beds ⋅ 2 Baths ⋅ 621197 MLS
Florida Keys living at its best! Absolutely lovely and truly a must see deepwater dockage with concrete dock and 20 thousand pound boatlift for your large boat 3 Bedroom 2 bath open living with beautiful kitchen with quartz counter tops downstairs large outdoor kitchen for all your friends & family entertainment all furniture included this area has a homeowners park with boat ramp and beach is a voluntary association with picnic area

234 Allen Ave, Key Largo
239 W Seaview Dr, Duck Key
$1,599,000
3 Beds ⋅ 4 Baths ⋅ 620472 MLS
DUCK KEY Showpiece. 2023 CBS home with high-end finishes features 3 bedrooms, 4 baths, large pool overlooking tropical island foliage in a private setting. Open floor plan, gourmet kitchen equipped with quartz countertops, custom cabinetry, and a distinctive full-wall ceramic backsplash. An additional 750+/- sqft of lower-level living includes a full bath that is perfect for a 4th bedroom, guest suite or game room. Designer touches and premium builder finishes throughout. Fenced outdoor living space, balconies, dedicated BBQ w/outdoor kitchen area, shed, privacy & more. Built for peace of mind, the property features a metal roof, full impact windows & doors ensuring low insurance costs. The current flood policy of $1,288.94+/- is assumable. Ample parking offers high-clearance carport perfect for your RV. Extensive storage available inside and out. Experience the relaxed island lifestyle that Duck Key has to offer. Easy access to world-class amenities at the Hawk's Cay Resort, nearby boat ramps, dining options, and a variety of activities. Membership to the exclusive Club Duck Key is available to further enhancing the island experience. Don't miss your chance to own a piece of paradise--schedule your showing today! Offered partially furnished; list of exclusions available. This home is a must see. B&BATVAI

239 W Seaview Dr, Duck Key
426 Calle Limon, Marathon
$1,599,000
5 Beds ⋅ 5 Baths ⋅ 618246 MLS
High-performing vacation rental located in the highly sought-after Sombrero Beach neighborhood, just a short walk to the beach. This fully furnished, turnkey property offers immediate income potential while also delivering an exceptional Keys lifestyle — truly a home that checks every box. Featuring 5 bedrooms and 5 bathrooms, the residence is thoughtfully designed for both guests and owners, including a legal bedroom and bath on the first floor. All living areas are above flood, offering peace of mind along with functionality. The home has been extremely well maintained and continues to perform strongly as a vacation rental. The main living level showcases a bright open-concept floor plan with high ceilings, modern finishes, and abundant natural light. The spacious kitchen includes sleek cabinetry, stone countertops, stainless steel appliances, and a large breakfast bar, seamlessly connecting to the dining and living areas. Sliding doors open to a balcony ideal for outdoor dining and enjoying island breezes. The primary suite serves as a private retreat with generous proportions, a walk-in closet, and a spa-inspired bathroom featuring a soaking tub and separate glass-enclosed shower. Each additional bedroom includes its own private bath, enhancing comfort and privacy for guests. A ground-level bedroom with direct access to the pool area adds flexibility for multigenerational living or guest convenience. Outdoor living is a true highlight, featuring a resort-style pool, covered entertaining areas, and a fully equipped outdoor kitchen with BBQ, perfect for hosting and relaxation. Additional features include a metal roof, ample parking, and space for two 20' boats on trailers. While boating is a major draw, this location also appeals to those who enjoy kayaking from Sombrero, beach days, and nearby parks. Whether as an investment, second home, or primary residence, this property checks all the boxes in one of Marathon's most desirable neighborhoods

426 Calle Limon, Marathon
97501 Overseas Highway Unit 114, Key Largo
$1,599,000
3 Beds ⋅ 3 Baths ⋅ 618835 MLS
Nightly Rentals permitted! Enjoy water views from the over-sized balcony and large master suite. This unit comes furnished w/ marble floors, granite counter tops, new stainless steel appliances, washer/dryer, impact doors & windows, plus new A/C. Mariner's is a gated community offering a clubhouse, fitness center, 2 pools, jacuzzis & grotto, a 43 slip marina with dry storage, indoor/outdoor pickleball courts, basketball & tennis. Mariner's Club is one of the few places in the Keys that allows nightly rentals. An incredible investment opportunity.

97501 Overseas Highway Unit 114, Key Largo
499 Sombrero Beach Rd, Marathon
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 621413 MLS
Welcome to 499 Sombrero Beach Road, a fantastic opportunity to own a piece of the Florida Keys lifestyle in Marathon! Ideally situated just off U.S. Highway 1 at approximately Mile Marker 50, this property offers a convenient location with easy access to Sombrero Beach, local restaurants, shopping, boating, fishing, and everything that makes Marathon such a sought-after Keys destination. This property provides a great balance of accessibility and the laid-back atmosphere the Middle Keys are known for. One of the few sand beaches of the Keys- Sombrero Beach is just down the bike path, a wonderful place to enjoy a day in the sun, take a swim, or catch a spectacular Keys sunset. Marathon is renowned for its world-class recreational opportunities, including boating, offshore and backcountry fishing, diving, snorkeling, and waterfront adventures. From this location, you'll be conveniently positioned to explore the surrounding islands while still being close to everyday amenities, restaurants, marinas, and local attractions. On site 56' dock was replaced in 2023 and features fish cleaning station, water and electric. The wide canal and premium 5' deep water access allows for larger boats than the average Keys property. Whether you're looking for a full-time residence, a vacation getaway, or an investment opportunity, 499 Sombrero Beach Road is a perfect opportunity. Established, professionally managed, licensed, weekly vacation rental. Come experience the relaxed pace, tropical surroundings, and endless outdoor recreation that make Marathon such a special place to call home. Updates include remodeled kitchen and baths, impact French doors, a metal roof (2021), and AC (2023). It's fully turnkey, with furnishings and future bookings included.

499 Sombrero Beach Rd, Marathon
182 Venetian Way, Sugarloaf
$1,595,000
3 Beds ⋅ 3 Baths ⋅ 620823 MLS
Experience classic Florida Keys waterfront living in this spacious canal-front retreat on Sugarloaf Key, offering boating access, expansive indoor-outdoor living, and just a short drive to Key West. 3,000 square feet of finished living space including 4 bedrooms and 3 baths. Situated on a wide canal with ample room for a future dock, offering the opportunity to create your own boating paradise. The massive chef's kitchen features copious marble countertops, abundant cabinetry, generous seating, and opens seamlessly into the impressive great room--ideal for entertaining family and friends. The open concept living spaces open onto a large canal-side deck that extends your living space outdoors. The spacious primary suite offers tranquil canal views and a spa-inspired bath with a soaking tub positioned to take in the waterfront scenery. A skylit bonus room offers endless possibilities as a fitness room, artist's studio, or sunroom. The nicely landscaped 13,000-square-foot property offers a circular drive, mature tropical plantings, and abundant parking for guests, boats, and recreational vehicles. Whether you're seeking a full-time residence, seasonal escape, or exceptional waterfront investment, this distinctive Sugarloaf Key home offers the space, setting, and Florida Keys lifestyle you've been waiting for.

182 Venetian Way, Sugarloaf
229 Coral Rd, Islamorada
$1,595,000
620208 MLS
DIRECT OCEANFRONT LOT IN ISLAMORADA WITH ACTIVE BUILDING PERMIT! A rare opportunity to own a beautifully situated direct oceanfront parcel in the heart of Islamorada, offering breathtaking panoramic views of the Atlantic Ocean. An active building permit is already in place, allowing you to begin construction of your dream waterfront estate immediately, or take advantage of the Village of Islamorada's available two-year permit extension. This spacious homesite includes a mangrove height reduction permit, allowing the mangroves to be trimmed to six feet. Upon completion, the property will enjoy unobstructed ocean views at ground level, creating an exceptional setting for luxury coastal living. Enjoy direct ocean access with convenient nearby Florida Bay access via Snake Creek, as well as close proximity to dry-dock marina facilities. Potential exists for an observation deck and/or dock, further enhancing the property's appeal and maximizing the spectacular waterfront setting. The elevation rendering is conceptual and provided for illustrative purposes. Utilize the approved plans currently in place or modify them to create a custom residence tailored to your vision. Opportunities like this are increasingly rare--build your dream home and experience the unparalleled beauty, boating, fishing, and island lifestyle that make the Florida Keys so desirable.

229 Coral Rd, Islamorada
643 Indies Rd, Ramrod
$1,595,000
3 Beds ⋅ 2 Baths ⋅ 618915 MLS
Nestled on the picturesque shores of Ramrod Key, this stunning waterfront property is the epitome of tropical luxury. With 3 bedrooms, 2 bathrooms, and 2,229 square feet of thoughtfully designed living space, this home offers an ideal blend of comfort and high-end amenities on a spacious 9,000 square foot lot. Completely remodeled in 2018, including a new roof, this property is ready for immediate enjoyment. Step into an open-concept living area featuring 10-foot ceilings, while the master bedroom boasts soaring cathedral ceilings with beautiful whitewashed cypress, adding a coastal charm to the elegant interior. The kitchen is a chef's dream, featuring quartz countertops, cherry hardwood cabinets with self-closing doors, a gas cooktop, and a convection oven. The master bathroom includes a luxurious 6-foot jetted tub with an on-demand water heater, creating the perfect place to unwind. Outdoor living is equally impressive, with a heated pool, two tiki huts featuring custom bars, and a spacious wrap-around deck offering panoramic open-water and sunset views. Boaters will appreciate the property's 14,000-pound boat lift, excellent boating access, and 50-amp shore power along with RV hookup complete with sewer connection. Relax by the gas fire pit, pick fresh fruit from the yard, and entertain with ease thanks to the exterior and interior sound systems. This fenced property, perfect for pets, also includes underground power, Wi-Fi, a 50-amp RV hookup, and plenty of storage. For the avid angler there's a fish-cleaning station and an outdoor shower. Combining privacy, luxury, and functionality, this Ramrod Key Oceanside gem is a slice of paradise waiting to be enjoyed. Easy and fun to show!!!

643 Indies Rd, Ramrod
2519 Staples Ave, Key West
$1,575,000
4 Beds ⋅ 4 Baths ⋅ 621374 MLS
Welcome to 2519 Staples Avenue, a fully reimagined residence in the heart of Midtown Key West, set on a rare 10,000 sq ft corner lot along one of the area's most bicyclable and desirable streets in Midtown. Recently completed renovations offer the opportunity to be the first to live in this thoughtfully rethought home, where modern upgrades meet relaxed island living. Spanning approximately 2,100 sq ft, the property features 4 bedrooms and 3.5 bathrooms, with a layout designed for both comfort and functionality. The primary suite serves as a private retreat, complete with direct access to the backyard, a spacious walk-in closet, and a beautifully appointed ensuite bathroom. Outdoor living is where this home truly stands out. A newly installed pool with elegant deck jets creates a serene, resort-style setting, fully enclosed for privacy. The new addition of a bright and airy pool room offers a seamless indoor-outdoor flow- perfect for entertaining or unwinding. There is a separate sitting and dining area for eating and lounging el fresco. Beautiful mature fruit trees provide shade and produce fruit annually. Additional upgrades include all impact windows and doors, providing peace of mind and energy efficiency throughout. New sewer and plumbing pipes to the road. New electrical and a new water heater. There is plenty of parking for a boat, a truck, a golf cart and a car. Properties offering this combination of lot size, location, and new construction-level renovations are exceptionally rare in Key West. Whether you're seeking a full-time residence, a family home, or a vacation retreat, this property delivers. House is being offered fully furnished minus personal items, art, and rugs. A true standout opportunity in Midtown, don't miss it!

2519 Staples Ave, Key West
3 Tiburon Cir, Shark Key
$1,575,000
621094 MLS
Prestigious Shark Key! Build your dream home in this Private, Gated, Luxury Community...This oversized Buildable, Permitted Lot encompasses 13,545 sq.ft., with breath taking open water views! The approved plans for this luxury home have 4,551 sq.ft. of living space, 1,200 plus square feet of porches, decks, and a 160 foot observation platform. Behind the private gates you will be surrounded by the crystal clear emerald waters of prestigious Shark Key. This exclusive property is just 15 minutes from Historic Key West with renowned dining, arts, culture, and vibrant nightlife. Build your dream estate in one of most sought after neighborhoods in the entire Florida Keys and enjoy the ultimate in Florida Keys Lifestyle.

3 Tiburon Cir, Shark Key
1005 Watson St Unit 1, Key West
$1,575,000
3 Beds ⋅ 2 Baths ⋅ 620577 MLS
Experience the best of Old Town Key West in this beautifully updated 3-bedroom, 2-bath home offering the ease of single-level living. Inside, you'll find hardwood floors, tall ceilings, French doors, stainless steel appliances, and an inviting open layout filled with natural light. Designed for the Key West lifestyle, the private backyard features a saltwater pool with heater and chiller, outdoor shower, lush tropical landscaping, spacious patio, and two dedicated off-street parking spaces. This property is turnkey, fully furnished and ready to enjoy from day one. Well maintained and tastefully updated, recent improvements include a new HVAC system, saltwater pool system, updated furnishings and termite tenting. Currently operating as a monthly vacation rental with an established rental history. Located in the center of Old Town just moments from Higgs Beach, Duval Street, the Historic Seaport, neighborhood cafés, restaurants and shopping. This property offers the privacy and feel of a single family home, it is part of an intimate two-unit condominium association with no shared common elements. Whether you're looking for a successful investment property, a full-time residence, or your own island getaway, this home checks every box. Schedule your private showing today to explore this Key West opportunity.

1005 Watson St Unit 1, Key West
365 Loeb Ave, Key Largo
$1,565,000
3 Beds ⋅ 2 Baths ⋅ 620142 MLS
Discover the essence of the Florida Keys lifestyle with approximately 165 feet of prime ocean-side dockage with a seawall and another 35 ft of buildable concrete/wood dockage in Key Largo. Perfectly positioned on a corner lot at the end of a quiet street, this exceptional waterfront property offers outstanding privacy and direct boating access to the open ocean in approximately 10 minutes via a single waterway. The main residence features three bedrooms and two baths, enhanced by soaring 10-foot ceilings, rich Brazilian cherry wood floors, granite kitchen countertops, and elegant marble-topped bathroom vanities. The spacious primary suite includes a large walk-in closet and a luxurious custom-built bath with a deep soaking tub. A separate in-law cottage provides the ideal space for guests, extended family, or an income-producing opportunity. A private balcony overlooks the water, while the expansive dock is designed for boating, fishing, and waterfront entertaining. Located just minutes from John Pennekamp Coral Reef State Park, you are surrounded by some of the finest diving, snorkeling, and natural beauty in the Florida Keys. With easy access via Blackwater Sound and close proximity to Jewfish Creek, you are only minutes from both the Atlantic Ocean and Florida Bay - offering the best of both worlds.

365 Loeb Ave, Key Largo
947 Gulf Dr, Summerland
$1,559,000
3 Beds ⋅ 2 Baths ⋅ 621442 MLS
Set on a deep, clean flow-through canal with no-bridge access to the Atlantic, this well-maintained Summerland Key home is designed for boating and outdoor living. The property offers approximately 60 feet of dockage, davits, and two swim ladders, making it easy to enjoy fishing, diving, and days on the water. Inside, the home offers three bedrooms, two baths, a spacious living area, dining space, and kitchen. Travertine flooring runs throughout the main living spaces, while the open layout brings in plenty of natural light. The kitchen features granite countertops, stainless steel appliances, generous cabinetry, and ample workspace. A screened veranda of approximately 280 square feet overlooks the canal and provides plenty of room for outdoor dining, relaxing, and enjoying the Keys lifestyle. The primary suite includes a private bath, generous closet space, and direct access to the outdoor living area. Two additional bedrooms provide comfortable space for family or guests. Downstairs, the elevated design creates extensive covered parking and storage with room for multiple vehicles, boats, trailers, and recreational gear. The fenced lot is surrounded by mature palms and tropical landscaping, adding privacy and a relaxed Keys feel. Located in an established Summerland Key neighborhood close to dining, shopping, and everyday conveniences, the property combines excellent boating access, generous outdoor space, and a practical three-bedroom layout for full-time or seasonal living.

947 Gulf Dr, Summerland
29424 Forrestal Ave, Big Pine
$1,550,000
3 Beds ⋅ 2 Baths ⋅ 620317 MLS
If you've been dreaming of easy waterfront living in the Keys, this beautifully furnished CBS home in friendly Pine Channel Estates is ready to welcome you. Built in 1989 with solid construction, it offers 1,392 sq. ft. of living space, poured concrete floors on pre-stressed beams, and an impressive 754 sq. ft. garage/storage area. Inside, cathedral ceilings and high transom windows bring in plenty of natural light and give the home an open, comfortable feel. Outside, enjoy 75 ft. of canal frontage with a step-down dock, two boat lifts, one of which is rated for 14,000 lbs., and very quick boat access to Pine Channel, the ocean, and the backcountry. The split-bedroom floor plan offers 3 bedrooms and 2 baths; overlooking the canal, the south-facing screened porch provides additional outdoor living. Accordion shutters and a metal roof add peace of mind. Permitted in 2007, the elevator is no longer functional and is being sold as-is. This is a solid, comfortable Keys home where boating, sunshine, and life in paradise are right outside your door.

29424 Forrestal Ave, Big Pine
169 Venetian Way, Islamorada
$1,550,000
5 Beds ⋅ 3 Baths ⋅ 619545 MLS
Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of concrete with impact windows and doors and recently painted inside and out, this home blends style, safety, and comfort. The property's coastal architectural charm is highlighted by a beautiful wrap-around porch and a curved pavered driveway leading to the air-conditioned garage. the main floor includes three bedrooms and 2 baths, featuring a master suite at the end of the home with private access to the backyard and heated pool. Upstairs two large bedrooms share a Jack-and-Jill bath, ideal for family or guests. The chef's kitchen boasts stainless steel appliances, an eat-in area, and a full walk-in pantry, flowing seamlessly into the sun-room and open living/dining area with a canal view. The outdoor living spaces are designed for entertaining and relaxation, including a heated pool with Jacuzzi, torch-lit ambiance around the pool, a fire pit and beautifully landscaped grounds. An air-conditioned shed - currently used as a potting shed - can easily serve as a playroom, art studio, or man cave. Boating enthusiasts will love the boat storage with in-and-out service less than 5 minutes away, offering reduced maintenance and added protection. Convenient access nearby to boat ramps at Founders Park, which also offers a sandy beach, pool, dog park, and sports field. Many community events held here - and you can just walk over to them. This home is set in a private, desirable neighborhood near upscale dining and amenities. Luxury, versatility, and lifestyle in one perfect package. Please schedule your private showing today to experience 169 Venetian Way!!

169 Venetian Way, Islamorada
340-350 E Ocean Dr, Key Colony
$1,550,000
5 Beds ⋅ 3 Baths ⋅ 619018 MLS
Investors! Full Duplex! Own both sides! This is rare opportunity to own a legal duplex being sold in the heart of Key Colony Beach in the beautiful Florida Keys. Located just one street off the Atlantic Ocean, 340-350 E Ocean Drive offers exceptional space, boating access, and an amazing investment opportunity with flexibility at a competitive price designed to sell. With 5 bedrooms, 3 bathrooms, and over 2,900 sq ft of living space, this property provides the rare opportunity to own a large waterfront home while still benefiting from the layout of a legal duplex. Sold together as a single property, it offers incredible versatility for full-time living, vacation use, or income-producing investment. Boaters will appreciate 50 feet of dockage with dual docks, allowing space for multiple vessels and providing a quick, easy ride to the open Atlantic for world-class fishing and boating. The 340 E Ocean Drive side features towering ceilings and dramatic floor-to-ceiling windows, filling the home with natural light while showcasing beautiful canal views from multiple areas. This side includes 3 bedrooms, 2 bathrooms, and a private balcony to enjoy the coastal breeze. The 350 E Ocean Drive side offers 2 bedrooms and 1 bathroom, along with its own private balcony overlooking the canal, the perfect spot to enjoy a morning coffee or evening sunset. Head over to the Cabana Club which is just steps away, for some fun in the sun! Enjoy both ocean and canal views from this prime location just steps from the Atlantic. With a proven rental history, this property offers outstanding flexibility. Owners have the flexibility to live in one side and rent the other or rent both for maximum income potential. Updates include; •Impact windows and doors (2021) •5V Metal Crimp Roof (2021) •AC ( 2021 & 2023) •New Dock Posts (2024) Competitively priced and offering size, dockage, and location, this is a standout opportunity to own a versatile waterfront property in Key

340-350 E Ocean Dr, Key Colony
303 Sombrero Beach Rd, Marathon
$1,549,000
4 Beds ⋅ 4 Baths ⋅ 620220 MLS
Waterfront duplex opportunity on Sombrero Beach Road in Marathon, just about 1 mile from Sombrero Beach. This stilted full duplex offers 4 bedrooms, 4 bathrooms, 2,114 square feet of interior living space, a pool, 110 feet of concrete seawall, dockage, and deep-water boating access. Each side features 2 bedrooms, 2 bathrooms, approximately 1,057 square feet, open living and dining areas, kitchen, washer and dryer, and enclosed sun porch areas with water views. The layout works well for a full-time residence, second home, investment property, or a live-on-one-side and rent-the-other setup. Outdoor features include an in-ground pool, decking, front porch, low-maintenance gravel yard, and a large circular paver driveway with plenty of parking and trailer storage. Boaters will appreciate the 110 feet of dockage with room for multiple vessels. The lower level includes two garages and substantial storage space, ideal for fishing gear, boating equipment, a cabana-style setup, or general storage. With its waterfront setting, duplex layout, pool, dockage, and close proximity to Sombrero Beach, this property offers multiple options in one of Marathon's most desirable lifestyle locations. B&BATVAI

303 Sombrero Beach Rd, Marathon
2613 Gulfview Dr, Key West
$1,549,000
3 Beds ⋅ 3 Baths ⋅ 618065 MLS
Rare WATERFRONT home on the island of Key West, an incredible value priced well below the last comparable sale. Tucked behind the gates of the exclusive Gulf View Pointe community, a rare opportunity awaits to own a waterfront townhome in Key West. This three-bedroom, three-full-bath residence offers the luxury of a private pool and includes a dedicated carport. As you step through the front door, you are welcomed into a bright, open home filled with natural light. The spacious kitchen flows seamlessly into the dining and living areas, all offering beautiful water views overlooking the backyard. The first floor also features a bedroom--currently used as a workshop--and a full bathroom. Upstairs, you'll find two bedrooms, each with its own ensuite bath and private deck. The primary suite's deck offers stunning water views. Outdoor living is a highlight of this property. The backyard features a large covered deck leading to the pool, all positioned westward to capture afternoon sun and spectacular sunset views. Plans and permits for your own private dock are already underway. Ideally located, this home offers convenient proximity to local stores and restaurants and is just a bike ride away from everything downtown Key West has to offer. Whether relaxing poolside, enjoying sunset views, or heading out to explore the island lifestyle, every day is framed by comfort, convenience, and the natural beauty of the Gulf.

2613 Gulfview Dr, Key West
1791 Grouper Dr, Marathon
$1,539,000
3 Beds ⋅ 2 Baths ⋅ 621017 MLS
Proven rental income meets the Florida Keys lifestyle in this solid CBS Marathon home featuring 60 ft. of concrete dockage with instant Gulf access. This well-established weekly rental property averages $105K in annual gross rental income and boasts 144 VRBO reviews with a 9.8 rating. (Future rentals must be honored by buyer). Enjoy a heated cocktail pool with sun shelf and waterfall spa, plus a fenced, low-maintenance yard and ample paver parking for boat trailers, RVs, and vehicles. Additional highlights include impact windows and doors, a metal roof and two storage sheds. Come see why this established, beloved neighborhood is such a special place to call home!

1791 Grouper Dr, Marathon
11401 Overseas Hwy, Marathon
$1,533,333
2 Baths ⋅ 619199 MLS
Fantastic commercial opportunity with direct highway exposure in a prime corner location! This oversized CBS building has 3,429 sq feet of air conditioned space plus a double drive-thru and an open patio upstairs. Commercial zoning allows for many office or retail uses. Very visible 15,000 sq ft corner lot with ample parking for customers and employees. Call for a private tour!

11401 Overseas Hwy, Marathon
193 Golf Club Dr, Key West
$1,500,000
4 Beds ⋅ 3 Baths ⋅ 620988 MLS
Located within the private Sanctuary enclave of the Key West Golf Club, this 4-bedroom, 3-bath residence offers rare privacy, coveted west-facing sunset exposure, and direct frontage along the 18th hole of the Rees Jones-designed course, all within the City of Key West. With approximately only 10 homes in the entire Key West Golf Club community offering 1,800 square feet or more of living space, opportunities at this size are exceptionally limited and rarely come to market. Inside, new tile flooring runs throughout, complementing a bright, open floor plan designed for effortless everyday living and relaxed entertaining. Expansive living and dining areas are filled with natural light and transition seamlessly to the outdoor space, where a private pool overlooks manicured fairways and wide-open skies. The setting is tailor-made for sunset gatherings, evening swims, or simply unwinding as the sun drops over the course. The well-appointed kitchen remains connected to the main living areas, creating a functional and social heart of the home. Generously sized bedrooms provide flexibility for guests, family, or a dedicated home office. Upstairs, a private balcony captures elevated golf course views and dramatic western skies, offering a peaceful retreat that feels distinctly removed from the everyday. The double-gated Sanctuary adds an extra layer of privacy and security, while residents enjoy access to two community pools and a fitness center. The golf clubhouse is just a short walk away. Nearby dining and daily conveniences allow you to enjoy the island lifestyle without always heading downtown, while Old Town Key West remains just minutes away. Approximately 15 minutes from the historic district, this property delivers a rare balance of tranquil gated living and easy access to beaches, boating, dining, and the vibrant energy that defines Key West. A sunset-facing golf course residence of this size, in this setting doesn't come around often!

193 Golf Club Dr, Key West
119 Peace Ave, Tavernier
$1,500,000
3 Beds ⋅ 2 Baths ⋅ 620623 MLS
Single Family Residential Key Largo property with canal view. With FEMA MAP actualized and currently active since 02/18/2005. C3 Kitchen updated, bathrooms updated. Satisfactory condition for the age and type of structure. With canal frontage with dockage and inmediate open water access. Three bedrooms and two bathrooms and covered rear deck with canal view.

119 Peace Ave, Tavernier
1821 Harris Ave, Key West
$1,500,000
9 Beds ⋅ 7 Baths ⋅ 619617 MLS
Right in the heart of Key West, this income-producing triplex is the kind of property investors are always asking for--strong numbers, solid layout, and a location that never goes out of style. The property features three spacious units, each offering 3 bedrooms and 2 bathrooms, making them highly desirable for long-term tenants. The front unit stands out with its single-level design--larger than the others and perfect for tenants who prefer the ease of one-story living. The two rear units are thoughtfully designed as two-story layouts, with living, kitchen, and entertaining space on the main level, and all bedrooms and bathrooms tucked upstairs for privacy. From an investment standpoint, the numbers speak for themselves. The units are currently rented at $4,500, $3,500, and $3,400 per month, bringing in a total annual income of $136,800 on long-term leases--steady, reliable cash flow in one of the most in-demand rental markets in the country. And then there's the location. You're just minutes from the coastline and a quick ride to downtown Key West, where all the restaurants, nightlife, and charm come together. Tenants love it here--which is exactly what you want as an owner. Whether you're looking to expand your portfolio or secure a high-performing asset in the Florida Keys, this triplex checks all the boxes.

1821 Harris Ave, Key West
Not Provided
$1,500,000
609363 MLS
10.5 Acre +/- Vacant Commercial Zoned ( C-2 ) Site on US #1 on Rockland Key , Bayside as you enter Key West. Approx. 1000 ft of Frontage on US #1 with 6.559 AC +/- of Upland filled from 5 ft to 9 ft elevation. $1,500,000 Price is Per Upland Acre. Existing billboard lease. Contact List agent for full package

Not Provided
169 Overseas Hwy, Rockland
$1,500,000
609364 MLS
10.5 Acre +/- Vacant Commercial Zoned ( C-2 ) Site on US #1 on Rockland Key , Bayside as you enter Key West. Approx. 1000 ft of Frontage on US #1 with 6.559 AC +/- of Upland filled from 5 ft to 9 ft elevation. $1,500,000.00 Price is Per Upland Acre. Existing billboard lease. Contact List agent for full package

169 Overseas Hwy, Rockland
3424 N Roosevelt Blvd, Key West
$1,500,000
3 Baths ⋅ 617342 MLS
Key West Jeep Adventures - Turnkey Tourism Business in Paradise Business Overview: Key West Jeep Adventures is a thriving, turn-key adventure rental company located in the heart of Florida's most iconic island destination. Specializing in premium Jeep Wrangler rentals, this business offers tourists the ultimate way to explore the Florida Keys in style and comfort. With a strong brand presence, high customer satisfaction, and a fleet of well-maintained, island-ready vehicles, this is a rare opportunity to own a profitable lifestyle business in paradise. Highlights: • Diverse Fleet: A mix of 2-door and 4-door Jeep Wranglers, many with convertible tops and custom island-themed wraps. • Prime Location: Centrally located in Key West with high visibility and easy access for tourists arriving by plane, cruise, or car. • Established Brand: Strong online presence, 5-star reviews, and a loyal customer base. • Proven Profitability: Consistent year-over-year revenue growth with scalable operations. • Turnkey Operation: Includes all vehicles, booking systems, website, marketing assets, and trained staff. • Partnership Ready: Relationships with local hotels, resorts, and travel agencies already in place. Growth Potential: Opportunities abound to expand services into guided tours, mapped excursions, or additional rental offerings such as scooters, e-bikes, or paddleboards. With Key West's year-round tourism and growing demand for experiential travel, the sky's the limit. Ideal Buyer: Perfect for an entrepreneur seeking a lifestyle business, an investor looking for a high-margin tourism asset, or a strategic buyer in the travel or adventure rental space. PRICE: $1,950,000 BUSINESS OP, INVENTORY: $2,700,000 SOLD SEPERATLY

3424 N Roosevelt Blvd, Key West
1504 Flagler Ave, Key West
$1,499,999
7 Beds ⋅ 5 Baths ⋅ 619911 MLS
Endless possiblities! Two units to rent for the investor or live in one and produce income from the other unit. Downstairs you have a 3/1.5 with an open floor plan and covered porch with a patio. Upstairs you have a 2/1 floor plan and a mother in law lock out. All units have W/D hook ups and central air. Low maintence yardcare. Covered and dedicated parking with street parking as well. Great location close to downtown and the beaches. Owner is a general contractor and has lived in the home since 1972 and added the second story in 1994.

1504 Flagler Ave, Key West