Divider
Content Divider

Florida Keys Homes For Sale on the Ocean Side of the Island. Oceanfront Homes

Total Listings 619
Order By:

$1,069,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
3 Bed, 3 Baths, 1,541 SqFt Days Listed: 313
-33.15% ($530,000) 6 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 880ft.

SPECTACULAR OCEANVIEWS!!! Just a few houses in from the Wide Open Ocean & Bay- CBS House 3 Bed/2 Bath - 80 ft. Concrete Dock on a Deep - Water -Wide - Canal. Beautifully Landscaped Yard. This home features - Cathedral Ceilings, Custom Cabinets & Island. Great Layout, & Impeccable Craftmanship on the Front Door & Tile through out. Plenty of Room for a Pool, RV, & All your toys. Quiet neighborhood - But close enough to Key West for all the Entertainment & Fun. Truly a Fishermans Dream.

$1,075,000
Marathon
Fat Deer Key   - MM: 53.00
4 Bed, 4 Baths, 1,740 SqFt Days Listed: 287
-10.34% ($124,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Assigned Dock35ft.Co

Waterfront stilted newer construction home that combines modern luxury with the serene beauty of the Florida Keys. This 4-bedroom, 3-bathroom residence is priced to sell. Inside, youll find a beautifully appointed living space, fully furnished and rental-ready. The kitchen features granite countertops, stainless steel appliances, and ample cabinet space. The open floor plan, accentuated by tile flooring throughout, makes it perfect for both relaxation and entertaining. The large master suite boasts a luxurious bath with a dual vanity, a huge walk-in closet, and an additional linen closet. Wake up to breathtaking sunrise views from the east-facing balcony that overlooks open waters. Outside, the property offers covered parking for four cars or space for trailers. The home also accommodates up to a 35 ft boat, making it ideal for boating enthusiasts. Community amenities include kayaks available for everyone to use, a resort-sized heated pool surrounded by comfortable lounge chairs and a charming thatched-roof cabana. The boat docks cater to the avid angler, while a sandy beach area invites you to unwind and soak up the tropical ambiance. Additional features include a newer A/C installed in 2020, a hot tub, a bait freezer, and window treatments throughout the home. The lush tropical landscaping enhances the vacation-like atmosphere. The homes metal roof and stilted design add to its durability and charm. With its excellent rental history and many repeat visitors, this property is a fantastic investment opportunity. The assumable flood policy under a favorable rate further adds to its appeal. Dont miss out on this exceptional property that combines luxury with the natural beauty of the Florida Keys. Contact us today to schedule a private tour and experience this tropical haven for yourself!

$1,075,000
Sugarloaf Key
Orchid Park Subdivision   - MM: 17.00
3 Bed, 3 Baths, 1,248 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Welcome to 17245 Jamaica Lane, a waterfront 3-bedroom, 2-bathroom home in the desirable Sugarloaf Shores. This elevated residence offers 1,248 square feet of comfortable living space with beautiful canalfront views and direct canal access for boating and fishing enthusiasts. This home offers distinct living, dining, and kitchen areas, creating a natural flow. The kitchen includes granite countertops, modern appliances, and ample storage, providing a functional and stylish space for cooking and entertaining. The primary bedroom offers plenty of natural light with an en suite bathroom, while two additional bedrooms provide flexibility for family, guests, or a home office. Enjoy serene canal views from the rear balcony, perfect for relaxing or unwinding after a day on the water. With direct boating access, youre just minutes from world-class fishing, sandbars, and the best of the Lower Keys. The spacious lot offers room for a pool, allowing you to create your own private backyard oasis. On the ground level, youll find a garage and covered space--ideal for storage, a workshop, or a shaded outdoor lounge. Plus, off-street parking provides plenty of room for vehicles, a boat, or even an RV. Located in a quiet neighborhood, this home is perfect as a primary residence, weekend retreat, or vacation rental opportunity. Dont miss your chance to own a slice of paradise--schedule your private showing today!

$1,089,000
Key Largo
Largo Beach   - MM: 91.00
3 Bed, 3 Baths, 1,040 SqFt Days Listed: 31
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Enjoy gentle breezes from your back porch, overlooking serene nature, your sparkling new pool, and a relaxing tiki hut. Nestled in Historic Tavernier, this charming 3-bedroom, 2-bathroom home offers the perfect blend of privacy and convenience--just a short walk from shopping, dining, and entertainment. Award-winning schools are less than two miles away.Located on a quiet street, the property has a coveted garage, plus plenty of off-street parking, providing ample space for all your toys. Inside, the open-concept living area is warm and inviting, featuring a stylish kitchen with granite countertops and stainless steel appliances. The upper-level floors showcase wood-look tile planks, and direct access to a private deck.Downstairs, youll find spacious enclosed areas--approved for storage only. Storage galore! Step outside to a large, private backyard with lush, protected mangroves as your backdrop. Kayaking and paddle boarding are at your fingertips. This home is a true Keys retreat--dont miss your chance to make it yours!

$1,090,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
3 Bed, 3 Baths, 1,764 SqFt Days Listed: 129
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.

Welcome to 66 Colson Drive in the desirable Cudjoe Gardens! This beautifully updated 3-bedroom, 2-bathroom canal-front home offers the ultimate Keys lifestyle with direct ocean access, ideal for boating enthusiasts. The bright and open floor plan seamlessly blends indoor and outdoor living spaces, perfect for entertaining or simply relaxing by the water. The kitchen features sleek finishes, stainless steel appliances, and ample storage. This home has a brand new roof and a new AC for immediate savings. Step outside to a tropical oasis, complete with a sparkling pool and a spacious patio, all overlooking the tranquil canal. With 80 feet of waterfront with a concrete dock, this property is ready for your next adventure on the water. Embrace Keys living at its finest in this move-in-ready gem in Cudjoe Key!

$1,090,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
2 Bed, 2 Baths, 768 SqFt Days Listed: 515
-19.26% ($260,000) 3 Price Changes : Last Change 35 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp

Open direct Ocean Water Views . Boat ramp and dock. Beautiful upper ocean deck with sea breeze.New metal roof in 2018 . Location is highly desirable . Priced right with Seller financing with 50% down Ocean Front Location*

$1,098,000
Cudjoe Key
Cudjoe Ocean Shores   - MM: 23.00
3 Bed, 3 Baths, 1,225 SqFt Days Listed: 121
+6.60% ($68,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Wow New Price. Best value in the area!! Discover the ultimate lifestyle with this 3-bedroom, 2-bathroom waterfront canal home on Cudjoe Key, a prime location. This unique property offers the best of both worlds; fast, convenient access to the open waters of the Atlantic Ocean and the tranquil Gulf of Mexico, allowing you to reach prime fishing spots in no time, dive, snorkel and cruise to the Keys sand bars. NUTS & BOLTS1,225 finished living space, additional lower level enclosed storage, Newer Metal Roof, 7,500 sqft Lot, 75 Canal Front, Stainless Appliances, Renovated Kitchen & Baths, Ample off Street parking The homes open floor plan is tiled throughout, providing a dream coastal retreat. Step outside onto a spacious back porch that overlooks the serene canal, perfect for morning coffee or views. The expansive, fenced-in yard offers both privacy and potential for outdoor enhancements.Additional features include ample storage space with a downstairs storage enclosure, covered parking for up to three vehicles, and a quick commute to the vibrant scene in Key West or the relaxed charm of Big Pine Key. Whether youre a fishing enthusiast or simply looking for an escape, this property promises an unbeatable Keys lifestyle with quick access to blue water and endless opportunity.

$1,099,000
Summerland Key
Snug Harbor Subdivision   - MM: 25.00
2 Bed, 2 Baths, 992 SqFt Days Listed: 53
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

Renovated Waterfront Gem! Welcome to your dream coastal retreat! This beautifully updated 2-bedroom, 2-bath home offers a 60-ft concrete dock along a 60-ft wide canal, providing the perfect setup for all your boating and water adventures. The property includes covered parking and a garage, ensuring convenience and plenty of storage for your vehicles and gear.Step inside to a bright and inviting space featuring brand-new impact windows and doors, a modern kitchen with quartz countertops, stainless steel appliances, and a stylish island--perfect for entertaining. Relax in the comfort of a durable metal roof and a new HVAC system for year-round peace of mind.Step outside to your screened patio, a tranquil spot to unwind while soaking in views of the canal and open water. Whether youre enjoying your morning coffee or an evening breeze, this serene space connects you with the beauty of waterfront living.Nestled in a boaters paradise, youre just minutes from incredible destinations like Little Palm Island, Looe Key, and Marvin Key. Dive into snorkeling, fishing, or island exploration, then treat yourself to the nearby fantastic restaurants for unforgettable dining experiences.This is more than a home; its your ticket to paradise. Dont let this one slip away!

$1,099,000
Marathon
Little Venice   - MM: 53.00
2 Bed, 2 Baths, 1,090 SqFt Days Listed: 88
-4.35% ($50,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 100ft.

Charming Waterfront Cottage in Little Venice. This beautifully updated 2-bedroom, 2-bathroom conch cottage is located in the highly desirable Little Venice neighborhood of Marathon. Perfectly situated on clear, deep, flow-through canals on two sides, the property offers approximately 100 feet of dock space, accommodating up to three boats. With easy access to Vaca Cut, the Atlantic Ocean, and the Gulf of Mexico in just five minutes, this home is a true fishermans and divers dream.The home has been tastefully updated with impact windows, a durable metal roof, sleek blinds, and stainless steel kitchen appliances. The thoughtful design includes a garage and off-street parking for added convenience. Whether youre relaxing on the water or heading out for an adventure, this home is perfectly positioned in the heart of Marathon, close to local attractions. Its just an hour away from the vibrant nightlife, fine dining, and airport in Key West, and a two-hour drive to Miami and Fort Lauderdale.Licensed as a vacation rental and with a strong rental history and future bookings available, its an excellent investment opportunity as well as a private retreat. Contact us today to learn more about this stunning waterfront gem!

$1,099,000
Ramrod Key
Breezeswept Beach Estates   - MM: 27.50
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 114
-15.40% ($200,000) 3 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 600ft.

Welcome to your dream waterfront oasis! This immaculate three-bedroom, two-bathroom home, built in 2020, offers a perfect blend of elegance and luxury. Meticulously maintained, this modern residence boasts ample privacy and quick boating access, making it an ideal retreat for water enthusiasts. As you step inside, youll be greeted by a spacious open floor plan that seamlessly connects the living, dining, and kitchen areas, perfect for entertaining family and friends. The contemporary design features high-end finishes and abundant natural light, creating a warm and inviting atmosphere. Outside, enjoy plenty of off-street parking for guests and a convenient downstairs enclosure/workshop, providing additional storage and workspace. The outdoor shower is perfect for cooling off after a day in the sun and on the water. Whether youre relaxing on the waterfront or hosting gatherings, this home is designed for both comfort and style. Dont miss the opportunity to own this stunning property that truly embodies the essence of waterfront living!

$1,099,999
Key Largo
Gulfstream Shores   - MM: 108.00
3 Bed, 3 Baths, 2,051 SqFt Days Listed: 79
Single Family - Contingent - Waterfront No
Side of Island: Ocean - Dockage: None

GREAT VALUE in this 4 car garage, screened pool and CBS home in popular Gulfstream Shores. This remarkable ground-level home spans three lots in a coveted area of north Key Largo. The spacious residence features a layout designed for both comfort and entertainment. A split floorplan offers a primary suite on the West wing of the home and secondary bedrooms on the other side with the kitchen in the center as the heart of the home. The home is characterized by its solid concrete construction, offering durability and peace of mind. Conveniently attached is a 2 car garage, with an additional detached 4 car garage providing ample storage space for vehicles or vessels. For relaxation and recreation, a screened-in pool enhances the outdoor living experience with minimal upkeep.Located just a short stroll from the oceanfront homeowners park, residents can enjoy access to a private boat ramp and exceptional boating opportunities. Gulfstream Shores is ideally situated, offering a tranquil lifestyle just a short drive from Miami and the prestigious Ocean Reef Club.Discover the perfect blend of coastal living and modern comfort.

$1,099,999
Key Largo
Key Largo Ocean Resorts   - MM: 94.50
4 Bed, 4 Baths, 1,584 SqFt Days Listed: 276
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Other Dock

Luxurious 4/3.5 in gated Key Largo Ocean Resort, a golf-cart friendly community featuring 24/7 security gate, clubhouse, fishing pier, marina, onsite boat ramp, basketball & tennis court, swimming pool, gym, kids park and so much more! And thats just the beginning! This home features an open floor plan with master suite on the main level, thick granite on all counters throughout. Kitchen is equipped with a wine cooler! Upper level has an additional master suite plus two more bedrooms. Every bedroom closet has upgraded build-in drawers and shelves. 2 AC units, metal roof, spray foam insulation, covered parking for multiple vehicles or even your boat, interior laundry, tankless hot water heater, outside shower, artificial turf, and lush landscaping. There is also a large storage room on the ground level for all your fishing & water toys. Electric box was also upgraded to include generator plug-in. It doesnt get any better than this. Dont miss this opportunity! Four bedroom homes in this community are rarely available. Picture yourself relaxing on the balcony after a long day of fishing and snorkeling in the crystal clear waters of the Florida Keys. Sit back and enjoy ocean breezes and a frozen cocktail! And bonus........Furniture is included! There are so many upgrades in this home! This is a great home for large families or even as an investment property! Additionally, owners can get on the wait list for a boat slip (additional fee for slip). However, a slip is not necessary as there is an on-site boat ramp and you can store your boat and trailer right under your stilt home! Competitively priced and will go FAST! Paradise is calling your name! Blink and it will be gone!

$1,100,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
2 Bed, 2 Baths, 772 SqFt Days Listed: 27
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Historic and charming 1936 Red Cross Home - Fully Remodeled - on 1/2 acre - in the heart of town! Step into history with this beautifully remodeled 1936 Red Cross home, originally built by the Red Cross to shelter hurricane survivors. Constructed entirely of concrete, including a solid concrete roof topped with durable metal, this home is built to last. Modern upgrades include impact windows and doors for added security and energy efficiency. Situated on over half an acre with tropical landscape in the heart of town, this 2-bedroom, 1-bathroom home offers both historic charm and modern convenience. The fully updated interior blends timeless character with contemporary comforts, making it move-in ready. Located on a road popular with walkers, joggers, and bicycle riders, this home is just moments from many shops, restaurants, and the vibrant Morada Way Arts District. Close to world famous Cheeca Lodge and the newly renovated Islander Resort which welcomes locals to its beach/pool bar and restaurants. With plenty of room for a pool or future expansion, the possibilities are endless. RV hookup. Dont miss this rare opportunity to own a true Florida treasure!

$1,100,000
Little Torch Key
Jolly Roger Estates   - MM: 28.50
3 Bed, 3 Baths, 1,576 SqFt Days Listed: 91
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.Concrete

Discover Conch Cottage, a charmingly updated 3-bedroom, 2-bathroom single-family home designed with a thoughtful split floor plan. This inviting retreat showcases bright, spacious rooms adorned with crown molding, recessed lighting, and elegant tile flooring throughout. The kitchen is a chefs delight, featuring granite and quartz countertops, stainless steel appliances, and plenty of cabinet space.Step outside to your private oasis, complete with 60 feet of dockage along a 50-foot-wide canal--perfect for boating enthusiasts with easy access to the ocean and bayside. The fenced backyard is packed with amenities, including a 312-square-foot screened patio, a tiki hut, a permitted detached gear storage/utility room, an outdoor shower, and a convenient fish cleaning station.Blending coastal charm with modern sophistication, Conch Cottage offers the ultimate in luxury and comfort. Fully furnished and turn-key, this home is ready for you to embrace the paradise lifestyle today!

$1,100,000
Plantation Key
Coral Harbour   - MM: 88.00
3 Bed, 3 Baths, 1,553 SqFt Days Listed: 304
-15.38% ($200,000) 2 Price Changes : Last Change 103 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Ramp,Boat Slip3

NOTICE TO CHC BUYERS: Coral Harbour reserves are funded to the amount required by law and passed 10 year Milestone inspection with the highest rating available. Step into luxury with this unique top-floor condo at Coral Harbour Club. The kitchen stands out with its custom design, offering modern appliances and plenty of space for culinary adventures. The master bedroom features a bespoke layout with high-end finishes, providing a serene retreat with stunning ocean views.Enjoy the convenience of partial furnishings, allowing you to easily add your personal touch to this beautiful home. The spacious living area is perfect for entertaining guests or relaxing after a day on the water. Speaking of water, the included deeded 35 slip is a rare find and a boaters dream, making this condo an ideal choice for those who love the ocean.Coral Harbour Club offers a range of amenities for residents, including a sparkling pool, a welcoming clubhouse, and private beach access. Located in a prime area, youll enjoy easy access to local shops, dining, and recreational activities, all while being steps away from the beautiful coastline.

$1,100,000
Big Pine Key
Cahill Pines & Palms   - MM: 30.00
2 Bed, 2 Baths, 1,464 SqFt Days Listed: 117
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: DavitsConcrete

This home is located on a beautiful 75 ft wide canal and has approximately 60 ft of seawall. Triton Seas Center is located on the same canal, just putt over and fill the boat up for a day of fishing and diving. Features a newer roof (2021), impact doors and windows, A/C (2022), fenced yard and appliances. This unique home plan and location make this home a must see.

$1,100,000
Summerland Key
Summerland Estates   - MM: 25.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 57
-7.95% ($95,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Rare 2/2-BR/BA Stilt Home with Airplane Hangar - A Pilots Paradise!Nestled near the airstrip and community boat ramp, discover a one-of-a-kind opportunity to own this 2-bedroom, 2-bathroom stilt home on an expansive 45,000-sqft lot. Cathedral ceilings, natural wood interior beams, storage unit downstairs, airplane hanger, Mexican Saltillo tile throughout including the large wrap-around balconies which are easy to screen. Offering 960 square feet of living space, this home is perfect for those seeking tranquility and adventure in a highly sought-after location.Key features includes a 1,400-sqft airplane hangar: Ideal for aviation enthusiasts, with easy access to the nearby runway, and the close proximity to the community boat ramp is perfect for boating, fishing, or waterfront leisure. There is ample space for outdoor activities or future expansions, and is zoned SR, Sub Urban Residential District, for more flexibility, and is listed in the transient rental zone for rentals of less than 28 days which requires a special vacation rental permit license and the buyer apply. The airport is a privately owned and operated, some dues and rules will be required to use the airstrip. Contact Summerland Key Airport for more information. This unique property seamlessly blends aviation convenience with coastal living. Whether youre a pilot, boat captain, or someone looking for a serene retreat, this home offers it all.Dont miss your chance to own this rare gem! Contact us today to schedule a private tour.

$1,100,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
4 Bed, 4 Baths, 1,459 SqFt Days Listed: 51
-18.52% ($250,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Your Slice of Paradise Awaits in Downtown IslamoradaDiscover the perfect blend of modern coastal living and convenience with this beautifully remodeled ground-level duplex in the heart of Islamorada. Located just a moment from the famous Cheeca Lodge and the vibrant Arts District, youll be surrounded by charming shops, restaurants, and galleries.Property Highlights: Two Separate Units PLUS a Guest Space: Each of the two dwellings is thoughtfully designed with a bright, airy ambiance to complement the island lifestyle. Use one unit for yourself and rent out the other, and/or welcome family and friends to visit! Durable Construction: Built with concrete and topped with a sturdy metal roof, this home is designed to withstand the elements. Impact windows and doors provide added protection and energy efficiency. Private Outdoor Oasis: The fully fenced yard features an electric gate, artificial turf for low maintenance, and lush landscaping with vibrant tropical foliage, perfect for relaxing or entertaining.Why Youll Love It:Whether youre looking for a permanent home or a vacation retreat, this property delivers the ideal Florida Keys lifestyle. The Village of Islamorada recognizes two dwelling units, adding significant value to the property.Dont miss your chance to own this coastal gem in an unbeatable location! Buyers should be able to convert this building in to one single-family home and transfer one of the building rights to another Village non-waterfront lot that is deemed appropriate by the Village. Two units are recognized by the Village. Buyers must confirm all with Village of Islamorada.

$1,100,000
Cudjoe Key
Cudjoe Gardens   - MM: 21.00
2 Bed, 2 Baths, 1,312 SqFt Days Listed: 98
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: 80ft.

Welcome to your perfect coastal retreat! This inviting 2-bedroom, 2-bath home plus office offers the ideal blend of comfort and convenience for boating enthusiasts. Nestled on the Oceanside with no bridges to navigate, it boasts a private 15,000 lb boatlift on 80 ft concrete dock a generous 4-ft draft making it a dream for those who love the water. Relax and unwind in the screened patio, perfect for enjoying the gentle sea breeze. adventures and serene waterfront living. Dont miss the chance to make this slice of paradise your own!

$1,100,000
Marathon
Grassy Key   - MM: 58.90
3 Bed, 3 Baths, 1,509 SqFt Days Listed: 57
Half Duplex - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Boat

This place has it all! Open water views can be yours at this Ocean Front A-Frame in private Lions Lair of Marathon. Outdoor Amenities include a pool, dockage for boats of 25 and under, boat ramp, tiki hut, boat trailer storage, clubhouse, and a paved path out to the jetty point. The Ocean Views greet you as you walk in this well built half duplex with impact windows and doors, 3 bedrooms, 2 baths and an office loft bonus space. Large outdoor deck that is perfect for morning coffee or an evening cocktail while enjoying the view. This is one of the premiere locations in Lions Lair offering the most privacy and convenient location to the marina and amenities. Association fees are only $1500 per year and no rentals are allowed, so you do not have to worry about being surrounded by noisy vacation rentals. Truly a unique and well built home in a hard to beat location, book your showing today!

The information being provided by the Florida Keys MLS is exclusively for consumers' personal, non-commercial use, and it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. Data last updated on 03-14-2025.
Back To TopMore Info
Terms / Privacy / Accessibility ADA