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Upper Keys Waterfront Homes for Sale, Single Family Houses, Open Water, Ocean and Bay / Gulf Views

Total Listings 213
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$1,295,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 3
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Enter the Islamorada waterfront game with this fantastic ground level 3-bedroom home, perfectly situated between Tavernier & Snake Creek with direct bay access. Equipped with a brand new metal roof and built above flood to help with insurance costs. Canal side has 50 feet of frontage with a 30-foot concrete dock in good condition and a permit in place to extend the last 20 feet. Perfect Keys weekend retreat or for those looking to make the jump up to waterfront living. Room for a pool. Close to schools and the neighborhood boat ramp. Lock it up just in time for summer!

$1,300,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 2,568 SqFt Days Listed: 28
-6.81% ($95,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

NEW PRICE DROP! MULTI-GENERATION families, INVESTORS this is a must see! Prime waterfront location for fishing, diving, and boating enthusiasts. Featuring a concrete block home with incredible potential, it provides immediate access to both ocean and bay-side adventures via a concrete dock. Whether youre finishing your day with a sunset on the water or hosting friends, the Sound views from nearly every corner of the property create a stunning backdrop for any occasion. Unbeatable waterfront access, perfect for ocean and bay-side boating. Expansive two-story layout with 2,304 sqft of living space (1,152 sqft per floor). 3 Bedrooms, 2 Bathrooms--ideal for families or a lucrative investment. with a BONUS Building serving as as a Cozy 1 bed/1bath guest quarters for visitors. Opportunities for single family, a MULTI generational family, a peaceful vacation retreat, or a smart investment, this property offers endless possibilities. Enjoy breathtaking views, a tranquil environment, and the ultimate waterfront lifestyle. Dont let this extraordinary opportunity pass by!

$1,300,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,240 SqFt Days Listed: 34
-7.14% ($100,000) 1 Price Change : Last Change 8 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

Looking for a home to accommodate you and your guests? This concrete construction property features three bedrooms and two baths on the upper level. Lower level offers two bedrooms and one bath, plus a waterfront screen porch, open floor plan, legally permitted enclosure with a living area that includes a kitchenette, plus living room. Plenty of storage with attached workshop/garage. Located on a plugged canal in Venetian Shores, there is a marina available for lease dockage monthly depending on availability.

$1,325,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,350 SqFt Days Listed: 183
-9.68% ($142,000) 2 Price Changes : Last Change 41 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp6

Prestigious Pirates Cove - Secluded Lake/Front Basin Home - Direct Ocean & Bay access in just minutes - 3Bed/2 Baths - The Upper Level is a 2 Bedroom/ 1 Bathroom & Lower Unit is a **Grandfathered in designated 1Bedroom/1 Bathroom with a Full Kitchen. Solid Concrete Dock equipped with a 15000 LB boat lift & Separate Jet Ski lift -Also property is Secured by an Electric Gate & Fenced in Yard complete with Shaded Patio area with Pavers and Tropical Landscaping - fish cleaning station & storage. Centrally located near Shopping, Schools & Restaurants.

$1,369,000
Plantation Key
Indian Waterways   - MM: 89.00
2 Bed, 2 Baths, 1,148 SqFt Days Listed: 2
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Dock Privileges,Boat

Waterfront Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedrooms with King Beds. Metal Roof , Smart TVs, Quartz countertops , open kitchen , Modern bathrooms, Great living room with open kitchen, Washer & Dryer, Screened in wrap around porch overlooking the water. 60 of Canal Frontage. HUGE enclosed Garage area underneath that can be extra living space New AC, New appliances, large yard area plenty of parking , 60 Private Dock , Beautifully remodeled. Large enclosed garage under home , Close to Founders Park with access to pickleball. swimming Pool , Beach, tennis and more. Own your own slice of paradise

$1,390,000
Key Largo
Key Largo Beach Addition   - MM: 100.00
5 Bed, 5 Baths, 2,157 SqFt Days Listed: 29
-2.46% ($35,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 36ft.

Experience waterfront living at its finest in beautiful Key Largo! As you step inside, youre greeted by stunning high vaulted ceilings that set the tone for this spacious home, offering five bedrooms and three bathrooms across 2,157 square feet of thoughtfully designed living space with convenient laundry access on both floors. Enjoy breathtaking ocean views from your living room, bedroom, or while relaxing on your pool deck. The upstairs features three bedrooms and two bathrooms, while the downstairs offers two additional bedrooms and a full bath, plus a versatile recreational space.The heart of this property is its exceptional outdoor area. A large, saltwater pool up to 8ft deep, invites you to bask in the Florida sun, surrounded by a generous pool deck perfect for entertaining or unwinding. Situated on an oversized corner lot with over 42 feet of canal frontage, the lush greenery and ample parking provide plenty of space for your vehicles, toys, and guests. Featuring a single-car garage, metal roof, modern impact windows, doors, and skylight. The modern kitchen, complete with stainless steel appliances, a wine cooler, granite countertops, and a sleek bar top, is perfect for any occasion. Located near Key Largo Park, youll be close to Key Largo Fisheries, schools, shopping, and just an hour to Miami. This is the ultimate Key Largo retreat!

$1,399,000
Plantation Key
Port Of Call   - MM: 88.50
2 Bed, 2 Baths, 1,248 SqFt Days Listed: 543
-18.90% ($326,000) 4 Price Changes : Last Change 2 Days Ago
Townhouse - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Slip

Ocean View Completely Remodeled Townhouse in Beautiful Islamorada!This beautifully updated town home offers 2 bedrooms, 2 bathrooms and a powder room including an ocean view Master Suite, with private porch and roof top deck, an amazing kitchen, with sunroom dining, open living space with ocean views and a screened porch. Located in Private Port of Call allowing weekly rentals with only 10 units featuring an ocean front pool, boat slip, sandy beach, carport, storage, laundry room in the unit with a pantry. This is a great investment opportunity with excellent rental income. Call for an appointment today!

$1,449,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,360 SqFt Days Listed: 12
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift50ft

Welcome to the Keys Life Getaway! Located in the desirable Tavernier neighborhood of Plantation Key Colony, this fully furnished 3 bedroom, 3 bathroom concrete canal home is awaiting your arrival. Situated on a deepwater canal, youll enjoy quick access to Florida Bay or the ocean via Tavernier Creek. The property features low maintenance landscaping, a 15,000lb boat lift, jet ski davit and a storage shed. The neighborhood features a wonderful bayfront homeowners park where you can launch your boat or relax and watch the sunset! The boat ramp was recently renovated and features a new concrete ramp and dock. Optional membership to the homeowners park is $200/year. The home is conveniently located near Coral Shores High School, Plantation Key Elementary School, shopping, grocery, bars & restaurants. This home will make a great full-time residence, or 2nd home with the ability to generate vacation rental income.

$1,475,000
Key Largo
Cross Key Waterways   - MM: 103.00
5 Bed, 5 Baths, 2,027 SqFt Days Listed: 29
-4.84% ($75,000) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat LiftConcrete

Amazing Three-Story Waterfront Haven in Cross Key Waterways, KEY LARGO! Embrace the allure of coastal living in this impressive 5-bedroom, 4-bathroom Key Largo retreat. This waterfront charm provides abundant living space for you and your loved ones with large open balconies off each floor. This property have a 40-foot dock, and a 15,000-pound lift that effortlessly hoists your vessel. The loft space awaits--a canvas of possibilities for a home office, entertainment area, or even a tranquil retreat with captivating views. This property can be rented for a mininum of 28 days. Only one hour away from Miami. Call today.

$1,490,000
Key Largo
Key Largo Trailer Village   - MM: 101.50
3 Bed, 3 Baths, 1,500 SqFt Days Listed: 47
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift45ft.

Experience the ultimate Florida Keys lifestyle in this beautifully maintained waterfront home situated in Key Largo, offering sunset views over the Florida Bay. This solid concrete home features a metal roof, impact windows and doors, and a spacious open-concept living area with 3 bedrooms and 2 bathrooms, this home is designed for comfort and coastal elegance.Step outside to a low maintenance yard and enjoy 45 of deep-water concrete dockage, complete with a 10,000lb boat lift. Additional features include a spacious storage/workshop, covered parking, newer Rudd central a/c, premium tinting on all the windows and a fully fenced yard.Enjoy direct Florida Bay access with nearby Atlantic Ocean access for world-class offshore fishing. As part of the HOA, youll have access to two private boat ramp parks--one featuring a sandy beach and swimming area. Whether youre fishing, boating, or dining at nearby waterfront restaurants, this home is a perfect island retreat.This is an opportunity to embrace the Florida Keys lifestyle--boating, fishing, and sunsets right from your backyard!

$1,495,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits,Boat Lift75ft

Welcome to Two White Turtles, a beautifully renovated, turnkey waterfront coastal paradise retreat - perfect for a vacation rental, second home, or primary residence. This stunning canal-front property offers homeowner access to a rare white sandy BEACH and is designed for the ultimate Florida Keys lifestyle. The grand French door entrance leads to open-concept areawhich features soaring wood-beamed ceilings, abundant natural light, a gourmet chefs kitchen with quartz countertops, French door refrigerator, all stainless appliances, a pantry with pullout drawers, ample storage, a dining spot and living space for entertaining or lounging while watching a 55 TV. Off the lounge are two ensuite bedrooms, each with their ownbathroom, wall mounted TV, abundant closet space, and dual sinks with a walk-in shower in the primary suite. Outdoors, relax in the tiki hut by the canal, rinse off in the outdoor shower, or unwind in the private backyard overlooking the mangroves. The 75 dock with a 7k boat lift and davits makes this a boaters paradise, offering direct ocean and quick bay access via Channel 2 and 5 bridges - just minutes from Alligator Reef Lighthouse. Additional features include a one-car garage with extra storage, ample parking for trailers, multiple vehicles, and an RV. Featuring a fenced, no-maintenance turf grass yard with pavers, a newer 5V crimp roof, with impact windows and doors. Peekaboo ocean views, starry nights, and ocean breezes enhance the homes serene setting. A bonus generator, extra fridge and freezer also add convenience. An easy walk to some nearby restaurants is a plus, making this location a perfect slice of paradise. Come watch the manatees float by and experience Keys living at its finest. Schedule your private showing today!

$1,495,000
Key Largo
Winston Waterway   - MM: 102.00
3 Bed, 3 Baths, 1,224 SqFt Days Listed: 21
-3.55% ($55,000) 1 Price Change : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift60ft.

Welcome to 233 LaPaloma Dr. The seller of this fully updated ocean side keys home has left nothing for its new owner to do but to enjoy their dream keys lifestyle. All beds and baths are on one level plus it has a large enclosed garage great for storage and bonus space. The serene setting of this home enjoys privacy provided by a lush mangrove forest canal side. Plenty of room for water toys the 60 ft dock has a newer 14k boat-lift . Many many upgrades , newer roof newer AC , impact windows and doors, kitchen , baths and flooring. Upgraded lighting and ring alarm security system. Come enjoy all the keys has to offer!

$1,499,000
Key Largo
Pirates Cove   - MM: 98.50
3 Bed, 3 Baths, 1,106 SqFt Days Listed: 114
-7.75% ($126,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Ramp100ft.Concr

Just what you have been looking for! Double Lot Canal Front Home in Pirates Cove. Enjoy over 100 feet of dockage and stunning Florida Bay views from this beautifully updated ground-level concrete home. Set on two spacious lots, the property offers the flexibility to separate the lots if desired. With 3 bedrooms, 2 bathrooms, and plenty of indoor and outdoor entertaining space, this home is perfect for boating enthusiasts and those who love sunsets. The home features a bright, open interior with natural light, a welcoming family room and open concept living, kitchen & dining. Outside, the low-maintenance, resort-style yard provides exceptional privacy and includes a tiki hut for relaxing or entertaining. Theres ample parking for an RV, boats and or multiple vehicles. Located in Pirates Cove, this home offers access to a community boat ramp, a charming beach, and a private clubhouse through a voluntary HOA. Conveniently situated near schools, top-rated local restaurants, and shopping, with quick access to the mainland, this property is ideal for vacationers or full-time residents. Dont miss the chance to own a piece of paradise in this welcoming neighborhood! Call today.

$1,499,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,920 SqFt Days Listed: 196
-11.82% ($201,000) 2 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.Concrete

Incoming producing property with future bookings already in place! This two story-waterfront property in the Florida Keys within Lower Matecumbe Key (near mile marker 74) 3 bedrooms and 3 baths total (2 bed/1bath on the second floor, 1bed/1bath on first floor, and 1 full bath on exterior) on the ocean side with 1,920 sq ft of living space. Second floor has 2 bedrooms, 1 bath and first floor has 1 bedroom and 1 bath with an additional full bathroom on the exterior of the property. This unique canal front property offers a 6,600 sq ft total lot size with access to the open ocean and bay within minutes. 60 FT concrete dock offers space for your boats, jets skis and more. 2 boat lifts included in the purchase, one can hold up to 10,000 lbs and other 15,000 lbs. Plenty of parking for multiple cars within the actual property. Furniture can be included in the sale. Call us today for in-person/virtual showings.

$1,575,000
Key Largo
Anglers Park   - MM: 103.00
3 Bed, 3 Baths, 1,689 SqFt Days Listed: 40
Single Family - Kick-out - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Davi

PRICED TO SELL...11.2 ft above Flood (X Flood zone) single level family home On Adams Cut waterway. Home is Situated on 8300 SF lot. The architectural unique home is deceivingly spacious on the inside. The tall ceilings accentuate the living areas giving it an open concept. The home offers 3 generous bedrooms and 2 baths, ensuite master bedroom w/ large walk-in closet, kitchen with gas stove, separate laundry room, and separate large storage room. Brick pavers add to the outdoor patio entertainment area with a tiki expanding over the roof line. There has been approval to install an 11 x 19 pool. The serene waters stretching over Adams Cut offers excellent boating options for easy and convenient access to the Ocean and Bay on wide canal. Shrimp or fish off the dock. Close to main land, shopping, restaurants.

$1,599,000
Key Largo
Twin Lakes   - MM: 103.00
4 Bed, 4 Baths, 1,646 SqFt Days Listed: 115
Single Family - Contingent - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Paradise found in this waterfront concrete home with an excellent Key Largo location! Located just a few homes in from the open bay, and very close to the Adams Cut Waterway, allowing fast ocean and bay access. Upstairs is a wide open concept floor plan, sit up bar, kitchen with pantry, vaulted tongue and groove ceilings, tiled floors, 3 bedrooms and 2 bathrooms, and an expansive screen porch. Downstairs is a large covered entertainment area with barbeque, commercial ice machine, bar and seating area, a full garage and a 1 bedroom 1 bath apartment with separate entry. The large dock has 75 feet on the water, a new 17,000 pound boat lift, a hot tub spa, and room for a generous sized pool. The deep water canal is 60 feet wide. Adams drive is being renewed and repaved to raise the street and work is well under way! Completion should be early in the year. 1 hour to Miami International airport and yet a tropical world away!

$1,600,000
Key Largo
Stillwright Point   - MM: 105.50
4 Bed, 4 Baths, 1,116 SqFt Days Listed: 147
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

Your Island Paradise Awaits! Fully remodeled waterfront home featuring 4-bed, 2-bath + 2 guest-baths, with an outdoor shower for your convenience when enjoying the saltwater pool. Renovated with porcelain crystal floors, impact windows, new SS appliances & new AC unit. The washer/dryer machines & ample storage space in the utility room add comfort to your life. This captivating corner lot has 2 private docs that fit up to two 24 ft boats, new electric boat-lift, RV hook-up, EV charger & expansive space to park your cars, RVs & other toys! The 45ft yacht is included. Desirable location at the entrance of Key Largo/Black Water Sound, just moments away from national parks, restaurants, entertainment, grocery stores, air & water adventures, and all the best that the FL Keys have to offer! Great income-producing opportunity through short-term rentals!

$1,600,000
Key Largo
Dove Creek   - MM: 94.00
3 Bed, 3 Baths, 1,242 SqFt Days Listed: 56
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 70ft.

This concrete 3-bedroom 2-bath waterfront home offers the perfect blend of durability and coastal living. Enjoy fast ocean access from your private concrete dock, ideal for boating enthusiasts. The fully fenced property features a pavered driveway and plenty of space to build a pool. Inside, youll find solid wood doors, baseboards and cabinets, adding warmth and quality in a home. A spacious storage area on the first floor provides ample room for gear and equipment. Dont miss this opportunity to own a well-built waterfront home in the Florida Keys.

$1,625,000
Key Largo
Key Largo Ocean Shores   - MM: 100.00
3 Bed, 3 Baths, 1,999 SqFt Days Listed: 72
-4.41% ($75,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

Discover Your Private Oasis at Lorelane Place in Key Largo Ocean Shores!Welcome to this canalfront concrete home, perfectly nestled on a peninsula at the end of a quiet street. With 117 feet of clear, deep-water canal frontage, this property offers breathtaking views of lush tropical vegetation and serene water vistas.Relax in your beautifully landscaped surroundings, complete with a spacious yard ready to be enhanced with a pool and outdoor kitchen--perfect for entertaining. Unwind under the large tiki hut, overlooking the canal with excellent dockage and easy access to both the Atlantic Ocean and Florida Bay (bridge restriction applies). Enjoy the Florida lifestyle on the screened porch and private balconies, all designed to make the most of your waterfront retreat.Inside, this spacious 3-bedroom, 2-bathroom home boasts an open floor plan ideal for comfortable living and entertaining. Original well-maintained interior. The main floor includes an elevator connecting the ground and first floor, and the ground floor features a spacious workshop and enclosed storage area, offering endless possibilities.Additional features offered is an electric gated entry for added security, full-house generator and a 500-gallon propane tank and a generous amount of parking.This unique property offers privacy, tranquility, and the perfect setting to enjoy the natural beauty of the Florida Keys.

$1,649,000
Key Largo
Harborage   - MM: 97.50
3 Bed, 3 Baths, 1,290 SqFt Days Listed: 51
-1.55% ($26,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

Welcome to your dream waterfront home! This stunning new construction coastal-designed residence offers 3 bedrooms, 2 baths, and unparalleled access to the open ocean. Nestled in a sought-after community with a pool and private boat ramp, this home is built for luxury and convenience.Enjoy over 40 feet of concrete dockage with a brand-new boat lift, making it effortless to embark on your next adventure. With direct ocean access and deep water, this is a boaters paradise.Inside, youll find modern coastal finishes, high-end craftsmanship, and an open floor plan that maximizes water views and natural light. The surrounding neighborhood is flourishing with new luxury homes, making this an excellent investment in a growing, upscale community.Dont miss this opportunity to own a premier waterfront home in the Florida Keys!

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 04-01-2025.
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