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Upper Florida Keys Real Estate for Sale, Homes and Condos in the Florida Keys

Total Listings 542
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$1,225,000
Lower Matecumbe
Bay Harbour   - MM: 75.00
3 Bed, 3 Baths, 2,026 SqFt Days Listed: 394
-3.92% ($50,000) 1 Price Change : Last Change 286 Days Ago
Condo - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Slip30ft.

Bay Harbour condos, located at MM 74.5 on Lower Matecumbe is a very desirable community. BAY HARBOUR ALLOWS 7-DAY RENTALS. Transient Rental License can be obtained from the Village of Islamorada that allows weekly rentals which are restricted in most communities in Islamorada and indeed all of Monroe County. This 2,000 sq. ft three-bedroom, two and a half bathrooms has a view of the sunrise on the Atlantic Ocean. A 30 boat slip is included which allows quick access to Florida Bay and a short ride will bring you to the ocean through channel 2 or channel 5. This gated community boasts a fantastic pool and hot tub along with a gym, clubhouse and tennis courts. Landscaping and maintenance of the property is professionally directed by the on-site property manager. This unit is equipped with propane gas range. Floor plan dimensions in photos are very close estimates. Buyer to verify.

$1,239,000
Plantation Key
Coral Harbour   - MM: 88.00
2 Bed, 2 Baths, 1,330 SqFt Days Listed: 92
Condo - Active - Waterfront No
Side of Island: Ocean - Dockage: Assigned Dock,Boat S

50 slip comes with this 2 bedroom / 2 bathroom condo in Coral Harbour. The units boasts 1,330sf of living space, peek-a-boo ocean views, large outdoor living area, impact windows and sliding glass doors, washer and dryer in the unit and a spacious kitchen. Primary bedroom and living area has impact sliders that lead to the outdoor living area. This complex has many great amenities - marina, fuel dock with diesel and gasoline, ice, boat ramp, pool, clubhouse, saltwater lagoon with beach, car washing station, covered parking, tennis courts, bocce ball, horseshoe, gated community and amazing landscaping.

$1,244,000
Key Largo
Paradise Point   - MM: 105.00
3 Bed, 3 Baths, 1,848 SqFt Days Listed: 57
-0.48% ($6,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Bay/Gulf - Dockage: None

Welcome to your Luxury Pool Home!Step into this stunning, brand-new concrete home, expertly crafted with quality construction and attention to detail. From the moment you arrive, youll be greeted by a beautifully designed exterior featuring durable cement lap siding, a metal roof, impact windows and doors, and a striking paver driveway composed of large concrete slabs with turf in between, adding a modern touch that enhances the aesthetic appeal of the property while promoting sustainable landscaping.As you enter the ground level, youll immediately appreciate the open-concept floor plan, filled with an abundance of natural light and accentuated by 8-foot doors that elevate the space. The inviting living room seamlessly flows into the gourmet kitchen, complete with elegant quartz countertops and stainless steel appliances. This level also includes a convenient half bathroom and an ensuite bedroom featuring a full bathroom, ensuring comfort and privacy for guests.Step outside to discover large terraces that overlook a beautifully landscaped yard, creating a serene atmosphere that feels like your own private oasis. The sparkling swimming pool invites you to relax and unwind in the tropical surroundings.Venture to the second floor, where youll find two luxurious primary suites, each boasting its own ensuite bathroom. One of the suites features a spacious terrace, perfect for enjoying morning coffee or evening sunsets. Additional highlights include built-in cabinetry, custom closets for ample storage, and a conveniently located laundry closet to make everyday living a breeze.This exceptional home offers an unparalleled blend of luxury, comfort, and style, making it the perfect haven for you and your family. Dont miss the opportunity to make this stunning property your own!

$1,249,000
Key Largo
Key Largo North Marniers Club   - MM: 97.00
4 Bed, 4 Baths, 2,688 SqFt Days Listed: 173
-7.48% ($101,000) 1 Price Change : Last Change 39 Days Ago
Townhouse - Active - Waterfront No
Side of Island: Ocean - Dockage: Basin,Other Dockage

Perfect combination of Florida Keys getaway and income producing investment property! Mariners Club is a gated resort-style ocean front community with all the amenities you could ask for: deep water dockage, two beautiful pools overlooking the Atlantic, deep water marina, tennis, indoor and outdoor pickleball, Keys beaches, clubhouse, gym, dry rack boat storage. Youll be proud to host a house full of friends and family here - and youll have plenty of space! Four bedrooms and four bathrooms - all with a flexible layout. This three-story unit has a 1/1 guest suite on the entry level with a kitchenette and living room. The middle and top floors house three more bedrooms and three baths - plus bright kitchen/living/dining areas overlooking a lovely patio. The spaces can be connect or separated just by closing a door! Perfect for when youve got guests that need a little extra privacy. Fresh new flooring and paint throughout the entire unit, updated furnishings and deck spaces. The enormous primary suite even has a rooftop deck with peekaboo ocean views. This pretty home is a must-see. Impact windows and doors mean you are always storm ready. The association cares for the grounds and keeps the lush tropical vibe going strong. This is as low maintenance as you can get. Its all fun and no honey-do list for you! Mariners Club has no min/max on owner use or rental nights. Use a local property manager or rent on your own any way you like. This is very unusual in the Upper Keys! Pets are A-OK for owners and renters of longer than 6 months. Due from buyer at closing: $45,000 equity membership refundable at closing, non refundable $10,699.20 capital contribution. Grossed more than $180K in last 12 months.

$1,250,000
Key Largo
Pirates Cove   - MM: 98.50
2 Bed, 2 Baths, 1,120 SqFt Days Listed: 132
-2.72% ($35,000) 1 Price Change : Last Change 61 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift50ft.Concre

Charming Key Largo Bungalow with Bay Views and Boating Access! Discover the essence of Florida Keys living in this meticulously maintained 2-bedroom, 2-bathroom bungalow. Situated on a wide canal with immediate bay access, this home is a boaters dream come true. Spacious open-concept living area with vaulted wood beam ceiling is perfect for entertainment and relaxation. The primary bedroom features an en suite bathroom for added privacy and convenience. Step outside to enjoy a 50-foot concrete dock with a 14,000-pound boat lift, perfectly equipped for all your water adventures. Relax in the screened lanai, offering serene canal views, or entertain with ease in the built-in outdoor kitchen, ideal for grilling and cocktails under the Florida sun. After a long day of fishing, unwind in the hot tub or refresh yourself in the convenient outdoor shower. Tasteful details throughout make this home truly a tranquil Florida Keys paradise. Located in a vibrant community with a clubhouse and boat ramp nearby, this property blends charm and convenience. Just over an hour from Miami International Airport, its your gateway to the ultimate Keys lifestyle!

$1,250,000
Key Largo
Largo Sound Park   - MM: 103.50
3 Bed, 3 Baths, 2,496 SqFt Days Listed: 246
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Spacious floorplan home with lovely natural light. Split bedrooms. Solid concrete built. The pool will need to be resurfaced. Nice location on the upper deck patio. Property is in an X flood zone. This is a home for a large family to enjoy and is located in one of the premier sought after neighborhoods. The Great waterfront park with beach and boat ramp. Located near the school and also to shopping. Easy commute to Miami. The extra lot offers plenty of parking for all your vehicles and other toys, as well as a nice privacy

$1,250,000
Key Largo
Winston Waterway   - MM: 102.00
3 Bed, 3 Baths, 2,075 SqFt Days Listed: 5
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift50ft.

Open House Saturday, May 10th from 10:30 to 2:30! Welcome to this ocean side canal front home that blends strength, style, and charm. This 3-bedroom, 3-bath concrete bunker with a concrete roof offers peace of mind and lasting quality, along with impact windows and doors. This home is all about function, durability, and waterfront living. The large kitchen boasts stainless steel appliances, ideal for preparing fresh catch or hosting friends. The living area features beautiful pecky cypress walls, wood beam ceilings and a cozy fireplace that creates warmth and character, while custom blinds throughout the home add a touch of sophistication. The spacious primary suite features cedar-lined closets and an updated bath, offering comfort and privacy with a split-bedroom layout that separates it from the guest rooms. Step outside to your waterside screened balcony to enjoy the views, have your morning coffee or evening cocktails. Downstairs, youll find a spacious storage and workshop area -- ideal for all your gear, tools, and hobbies -- along with plenty of parking for family, guests, and your boat trailer. The large backyard offers endless potential, with room for a pool, a cozy fire pit for stargazing nights, and a covered porch perfect for outdoor gatherings. Your new home is situated on a wide clean ocean side canal with a 14000 LB boat lift to enjoy the Keys waters. Located in a peaceful, sought-after neighborhood, this home is just minutes from shopping, dining, and world-class fishing and diving.

$1,250,000
Key Largo
Dove Creek   - MM: 94.00
2 Bed, 2 Baths, 1,232 SqFt Days Listed: 162
-3.85% ($49,999) 1 Price Change : Last Change 4 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

Dont miss out on this east of US 1 canal front home with amazing views. Updated kitchen with quartz counters, Impact windows and doors throughout with shutters for extra protection. Tile floors, paver driveway, screened patio with no see-um screens, Fenced area of yard for pets, custom shades, upgraded appliances, the list is long and impressive. Dont forget the tiki with custom lighting and lots of space under home for entertaining and relaxing. Did I mention furnishings are negotiable? Dont wait call today to take a look.

$1,250,000
Plantation Key
Plantation Key Colony   - MM: 90.00
3 Bed, 3 Baths, 1,376 SqFt Days Listed: 41
-3.47% ($45,000) 1 Price Change : Last Change 2 Days Ago
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!

$1,250,000
Key Largo
Anglers Park Shores   - MM: 103.00
5 Bed, 5 Baths, 1,976 SqFt Days Listed: 15
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Beautiful 2 story 5 bedroom 2 bath Key Largo Home, 2 bedroom 1 bath upstairs, 3 bedrooms 1 bath downstairs, Bathrooms updated, kitchen updated new Quartz countertops and appliances. Solid concrete home including the roof. Great water views over Largo Sound. Spacious corner lot plenty of space for your boat, RV and extra parking. Suburban Commercial zoned for short term rentals, with proper licensing, access for Kayaking, canoeing, fishing and swimming. Hideout Restaurant just around the corner for breakfast, Enjoy coffee in the morning, beverages in the evening on your wrap around balcony. Washer and dryer Downstairs has separate entry, bathroom was originally permitted on the original plans with the county, downstairs bedrooms may be non-conforming. appointment only, Owner/Agent

$1,250,000
Key Largo
Largo Sound Park   - MM: 103.50
3 Bed, 3 Baths, 1,936 SqFt Days Listed: 96
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Welcome to this stunning new construction home offering modern luxury and resort-style living! With nearly 2,000 sq. ft. of beautifully designed living space, this spacious 3-bedroom, 3 1/2-bathroom home is the perfect blend of comfort and style. Each of the three bedrooms includes its own private en suite bathroom, providing ultimate convenience and privacy for family or guests. The open-concept layout features high-end finishes, a bright and airy living area, and a gourmet kitchen ideal for entertaining. The master suite is a true retreat, boasting a large walk-in closet and a luxurious en suite bathroom.Step outside to your private oasis, complete with a sparkling swimming pool - the perfect place to unwind or host family and friends. With optional membership, residents also enjoy exclusive access to a beautiful homeowners park with a sandy beach and boat ramp, offering endless opportunities for outdoor recreation and water activities.Located in a desirable community, this home provides the perfect blend of privacy and convenience. Dont miss out on this rare opportunity to own a piece of paradise. Schedule your private tour today!

$1,270,000
Key Largo
Largo Sound Park   - MM: 103.50
4 Bed, 4 Baths, 2,092 SqFt Days Listed: 42
+5.92% ($71,000) 1 Price Change : Last Change 31 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Opportunity is Knocking...Open the Door!!! LISTED BELOW APPRAISED VALUE!!! Nearly 1/2 acre of land in coveted Largo Sound Park. Unique property is cleverly laid out. Left structure has 3 bedrooms, 2 baths, a full kitchen, a living room, and a bonus room/Florida room. The right side 1320 sf addition built in 2000 has a separate entrance, kitchenette, office, bath, recreation room and garage. The roof covers both sides with a walkway between, all with separate entrances situated on 4 lots in the X-Zone (highest elevation in the Florida Keys). This neighborhood offers a voluntary waterfront homeowners park for a minimal annual fee, you will have access to a picnic pavilion, play area, sandy beach, and boat ramp. Easy Immediate ocean access by North or South Creeks while the bay may be easily accessed via Adams Cut. Close to school, shopping, restaurants, and easy commute to Miami. Delight in all the Florida Keys has to offer: Boating, swimming, snorkeling, world class fishing, and scuba diving. See documents tab for layout of home. SALE OF PROPERTY SUBJECT TO COURT APPROVAL.

$1,275,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,620 SqFt Days Listed: 46
-3.77% ($50,000) 1 Price Change : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Dock Privileges

Welcome to your perfect getaway in the heart of the Florida Keys! This beautifully updated 2-bedroom, 2.5 bathroom townhouse is located in Islamorarda in a resort-style community with fantastic amenities. Whether youre looking for a vacation home, an investment property, or both, this tropical retreat offers everything you need.Enjoy an open-concept living space with abundant natural light, a fully equipped kitchen, and spacious bedrooms with en-suite bathrooms. Step outside to your private balcony or patio and soak in the island breeze. This townhome is the only property in association that is situated on two lotsThe community features a sparkling pool, a marina with boat dockage. With weekly rentals allowed, this property is a fantastic income opportunity in a high-demand tourist destination.Located just minutes from world-class fishing, boating, snorkeling, and dining, this townhouse offers the ultimate Florida Keys lifestyle. Dont miss out on this rare opportunity--schedule your private tour today!

$1,275,000
Key Largo
Cross Key Waterways   - MM: 103.00
3 Bed, 3 Baths, 1,296 SqFt Days Listed: 98
-1.92% ($25,000) 1 Price Change : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift40ft.Concre

Stunning Stilted 3-Bedroom Home with Bay Access & ElevatorDiscover this beautiful stilted 3-bedroom, 2-bathroom home, perfectly designed for comfort and convenience. Featuring spacious bedrooms with incredible closet space, this home also boasts a large storage room on the ground floor and an elevator for easy access.Located just two canals from the open bay, youll enjoy quick ocean access via Adams Cut--ideal for boating and water enthusiasts. The property offers a fantastic entertaining area, covered parking, and ample space to store your toys and trailer. 40 of seawall with a 20,000LB boat lift in the process of being installed.Dont miss this opportunity to own a waterfront gem in a prime location!

$1,275,000
Key Largo
Lake Surprise Properties   - MM: 106.00
3 Bed, 3 Baths, 1,248 SqFt Days Listed: 355
-3.77% ($50,000) 1 Price Change : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits,Boat Lift60ft

Location, location, location... ideally situated in North Key Largo for boating, fishing, diving, dining, shopping & more. Convenient for commuting. Whether you are seeking a primary residence, vacation getaway, or an investment property, dont miss your opportunity to own this piece of paradise. Lovely 3/2 waterfront pool home located in desirable Lake Surprise Estates. Elevated by concrete columns w/ a spacious ground floor storage room. 60 concrete dock w/ lifts & an addl concrete pad. Easy access to the bay & ocean. Spacious floorplan, vaulted ceilings & tile throughout. Kitchen w/ granite countertops, stainless appliances & an expansive island. Completely fenced, electric gate & lots of room for all your water toys. Simple to maintain salt-water pool, accordion shutters up-stairs & newer metal roof. Large, covered wrap-around patio & 2nd floor porch, perfect for gorgeous sunset views. Plenty of space to enjoy w/ your loved ones.

$1,280,000
Key Largo
Key Largo Ocean Resorts   - MM: 94.50
3 Bed, 3 Baths, 1,695 SqFt Days Listed: 140
-5.19% ($70,000) 1 Price Change : Last Change 1 Day Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp

This newly built CBS home in desirable Key Largo Ocean Resort with a very tasteful and modern look. This home was built with a boaters mind set, 10ft high columns to accommodate your boat, community boat ramp and storage. Hurricane ready, CBS, impact doors and windows, elevator, 360 degrees lookout rooftop with amazing views, of ocean, bay, sunrise, and sunset. Very nice and open, kitchen and island with seating space, stainless steel appliances, 3 beautiful bedrooms and 2 baths. This turnkey home is ready and waiting for you. Come tour with us and discover lots more. Community offers, 24-hour security, clubhouse, gym, pool, playground, basketball Tennis court visitor parking. Too much to mention all.

$1,298,000
Key Largo
Key Largo Beach   - MM: 100.00
3 Bed, 3 Baths, 1,617 SqFt Days Listed: 241
-13.18% ($197,000) 4 Price Changes : Last Change 2 Days Ago
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: Boat Ramp,None

Welcome to your future home nestled in prestigious Port Largo neighborhood. This coastal style beautiful concrete home was extremely well built in 2020 with a modern and coastal design. This residence has been meticulously maintained. The spacious home offers 3 bedroom / 2 bath, separate laundry room, a dreamy kitchen w/ quartz counter tops and large center Island, tile thoughout. Indulge in the brand new outdoor pool and heated spa surrounded by sand under your toes, and equipped with a BBQ summer kitchen, outdoor TV. The fresh landscape and PVC fence allowing for privacy. Beyond enjoying the home itself, the community has an HOA Marina, Boat Ramp, and picnic beach area just at the end of the street approx 400 yards. Walk or golfcart to Key Largo Park, brand new 9 Pickle Ball courts, tennis, restaurants, groceries. This home is a rare gem in highly sought after location with a quintessential keys life style. Dont miss the opportunity to make this home your own paradise!

$1,300,000
Upper Matecumbe Key Islamorada
Misc Upper Matacumbe   - MM: 82.00
3 Bed, 3 Baths, 960 SqFt Days Listed: 8
Single Family - Active - Waterfront No
Side of Island: Ocean - Dockage: None

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the bedrooms ensuite. The home offers a great floor plan and has been tastefully decorated with a beautiful kitchen including stainless steel appliances. This is a great investment with rental history. Dont miss the opportunity to own where you can walk and ride your bike to all the places downtown Islamorada has to offer including shopping, restaurants, bars, and all the amenities The Sports Fishing Capital of the World has to offer!

$1,300,000
Key Largo
Cross Key Waterways   - MM: 103.00
4 Bed, 4 Baths, 2,568 SqFt Days Listed: 66
-6.81% ($95,000) 1 Price Change : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits

MULTI FAMILY OPPORTUNITY! Water view from every floor! 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 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: 72
-7.14% ($100,000) 1 Price Change : Last Change 30 Days Ago
Single Family - Contingent - 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.

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 05-09-2025.
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