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

Waterfront real estate in Islamorada is very popular within the Florida Keys real estate market.  Homes for sale on the water in Islamorada include those that are located on the ocean, the bay, and on the many canals that lead to open water throughout the area.  Since Islamorada draws fishing enthusiasts from around the world, the bayfront and oceanfront homes for sale in Islamorada are great for real estate buyers looking to capitalize on the best features of the area.  Browse all Florida Keys MLS listings of waterfront homes for sale in Islamorada below.

Total Listings 80
Order By:

84961  Old Highway 23 For Sale, MLS 587700
$495,000
Windley Key
Galen Beach   - MM: 85.00
2 Bed, 2 Baths, 705 SqFt Days Listed: 4
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

Move right into your fully furnished Oceanside Escape....catch the beautiful Florida Keys Sunrises and Ocean Breezes! Located in Windley Key Mobile Home Park Condo. This meticulously maintained newer stilt home offers 2 bedroom and 2 full baths metal roof, impact windows, open porch, carport for two, storage, chickee hut and Chicago brick patio to entertain with tropical landscape. Comes tastefully furnished. Home is built for 180mph wind velocity and has a Transferable Structural Warranty good till 2023. This rare quaint association has 48 units which sits overlooking the Atlantic Ocean. Low Association fees. Amenities include jetty to sit and soak up some Vitamin Sea, fish cleaning station, Marina, Sm boat ramp etc..... Must see!

168  Iroquois Drive  For Sale, MLS 585437
$665,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 168
+6.40% ($40,000) 1 Price Change : Last Change 76 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp5

This 3 bedroom 2 bath home in the sought after location of Lower Matecumbe in Islamorada boasts over 50 of dockage, 4,000 lb boat lift and a private boat ramp! Immediate access to ocean or bay for all your boating needs! Downstairs storage, covered fish cleaning station and gazebo for shaded entertainment! Home took some damage from the hurricane. Installation of new metal roof has been scheduled along with new flooring to be installed. Great opportunity to own a home in the Florida Keys! Easy to show! Option to purchase with adjacent lot at 172 Iroquois Dr. for $1,050,000.

129  San Marco Drive  For Sale, MLS 586261
$729,000
Plantation Key
Venetian Shores   - MM: 86.00
3 Bed, 3 Baths, 1,400 SqFt Days Listed: 113
-8.76% ($70,000) 3 Price Changes : Last Change 1 Day Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Basin,

Turn Key waterfront 3/2 concrete home in sought after neighborhood of Venetian Shores. Included in the sale is boat slip #14 in Marina which holds upto a 40ft boat. Open floor plan, SS appliances and granite countertops in kitchen. Vaulted ceiling in Kitchen and living room make room spacious and open. Large waterfront screened porch with french doors on waterside. Downstairs has large enclosed storage area, covered seating/lounge area and bbq. Pool plans have been approved...This property has a vacation rental history as well, to help offset cost.A MIUST SEE!! Least expensive property in the neighborhood!! MOTIVATED SELLERS

179  Azalea Street  For Sale, MLS 587253
$749,000
Plantation Key
Plantation Key Colony   - MM: 90.00
4 Bed, 4 Baths, 1,761 SqFt Days Listed: 36
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 50ft.Concrete

Price reduced on this 4 bedroom 4 bathroom all concrete canal front home in Plantation Key Colony. The upstairs is a 2/2. Tiled throughout this open floor plan with all wood kitchen cabinets overlooking the canal with a 24 x 8 screened in porch. There is a spiral staircase leading to the concrete roof top and concrete walk way around a majority of the second floor. One of the few legal downstairs consisting of a 2/1 apartment , an efficiency and a large storage area with Washer and Dryer. All of the downstairs is wheelchair accessible via concrete walkways to driveways. Ceiling fans in all rooms. Aluminum windows (awning and single hung). All concrete 50 dock on a wide free flowing canal which never accumulates seagrass. Ready for immediate occupancy. Call today this one wont last.

77340  Overseas Highway  For Sale, MLS 587336
$799,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 77.00
2 Bed, 2 Baths, 928 SqFt Days Listed: 29
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Concrete

Perfect opportunity to build your dream home in the Florida Keys, Village of Islamorada. Adjacent buildable lots on either side available For Sale for a total of 102,802Sq.Ft. to build your dream family compound (lots are listed for sale altogether or each individually- see Listing #587337 - Lot 4, 5 & 6/587338 - Lot 4/587339 - Lot 6). Property is on the Bay Side next to Robbies, just minutes to Tea Table and access to ocean.

100  Venetian Drive  For Sale, MLS 586439
$875,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 97
-1.69% ($15,000) 1 Price Change : Last Change 49 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Amazing views from this immaculate 2 bedroom 2 bath waterfront home on pristine canal with access to both Bay and Ocean. Panoramic views of large conservation area and lake allow privacy as there are no rear neighbors. Open concept plan with new metal roof, kitchen has new stainless steel appliances including refrigerator, stove and microwave. 1080 sq ft living area plus large patio and dock for your boat. House is built high enough to allow doubling of square footage by enclosing downstairs area. Opened unfinished attic for added storage space or future loft. Beautiful private homeowners beach on Bayside.

132  San Marco Drive  For Sale, MLS 586416
$899,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,447 SqFt Days Listed: 99
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

This spectacular two-story home in Venetian Shores on Plantation Key is modern and spacious.Move-in ready property includes 3bedrooms/ 2baths upstairs with 2 bedroom/1 bath guest suite downstairs. Enjoy an open floor plan with an updated eat in kitchen, wood cabinetry and granite countertops. The large master en-suite includes a walk-in closet and stunning water views. Other features spotlight a spa, a separate laundry room, screened in porches, impact resistant windows and metal roof. This offering includes an assigned boat slip #20 with lift in Venetian Shores Yachting Association Marina. Relax in your private backyard with enough room to add a pool.

138  San Marco Drive  For Sale, MLS 587282
$925,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,467 SqFt Days Listed: 34
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat S

Absolutely Perfect - This is the vacation/rental home everyone is looking for! Nicely maintained 5 bed/4 bath home on a quiet cul-de-sac in Islamoradas most desirable neighborhood... Venetian Shores! Concrete stilt home with a metal roof, heated pool, and a boat slip (#23) in the nearby marina with a 10,000 lb. boat lift! Strong rental history with booked winter rentals ready to convey to the new owner! This one is set up perfectly with a 3/3 upstairs so everyone gets their own bathroom (also good for company rentals). Downstairs is an above flood 2/1 apartment for family or guests. Freshly painted in and out with a brand new paver driveway and extra-high carport for toy storage. Enjoy wrap-around water views and relax with a cocktail on your porch while soaking in the sunset.

82762  Overseas Highway 4 For Sale, MLS 582266
$925,000
Upper Matecumbe Key Islamorada
Madeira Bay   - MM: 82.50
3 Bed, 3 Baths, 1,956 SqFt Days Listed: 368
-2.63% ($25,000) 1 Price Change : Last Change 147 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Ramp,

BAY VIEWS & BOAT SLIP IN ISLAMORADA! Waterfront gated enclave of 8 single family homes in Madeira Bay centrally located in the heart of Upper Matecumbe Key. Tri-level 3B/2B residence just one home off the bay, nice water views plus dedicated boat slip w/boat lift directly on Florida Bay. Open floor plan, vaulted ceilings, tiled floors, 2 central ac units, multiple sliding glass doors to bayside patios on both living levels. Ground floor offers carport, above flood guest quarters of 304 SqFt, large sundeck, low maintenance yard with lots of native foliage. Common areas include gated entry, pool, boat ramp & dock. Enjoy this unique peaceful location/setting in the Village of Islands.

124  Palo De Oro Drive  For Sale, MLS 585966
$995,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,764 SqFt Days Listed: 133
-9.55% ($105,000) 1 Price Change : Last Change 38 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Concrete construction, lower level guest quarters, 70 ft. of deep water dockage! This home has 3 bedrooms & 2 bathrooms on the main level, and a 1 bedroom, 1 bathroom lower level guest apartment. Foyer entry with interior staircase, open floor plan, with screened waterfront porch. Lot allows plenty of room for a pool! Located in desirable Venetian Shores featuring 100 ft. wide canals, offering immediate access to ocean and bay! Lots of potential!

168  Iroquois Drive  For Sale, MLS 586540
$1,050,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,232 SqFt Days Listed: 89
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Boat Ramp1

This canal front home on highly desired Lower Matecumbe Key in Islamorada boasts over 120 of dockage, 4,000# and 5,000# boat lifts and a private boat ramp! This home sits on a double, cleared lot on a private cul-de-sac road. The location offers immediate access to ocean or bay for all your boating needs! Downstairs storage, covered fish cleaning station and gazebo for shaded entertainment! Home took some damage from the hurricane and needs interior remodel. Installation of new metal roof has been scheduled. Easy to show! Home and vacant lot offered separately as well. Home for $625,000 MLS#585437 and lot for $425,000 MLS#586534.

137  Anglers Way  For Sale, MLS 586875
$1,100,000
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,638 SqFt Days Listed: 69
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 31ft.

Anglers Reef Home with deeded boat slip. The home has beautiful water views and tons of upgrades. The home also is the only unit with 3 carports and is the largest 2 bedroom model in the community at 1636 square feet under air. The home shows like a model out of a magazine. Upgrades include Brazilian cherry hardwood floors, impact doors and windows, 3 porches with ocean views and upgraded composite decking. The brand new kitchen and bathrooms are beautiful and have state of the art fixtures and appliances. Anglers Reef reef is a private gated community with 52 homes and amenities include a community pool, a marina, and 2 beaches. Home is currently in the rental program. Own a home in the Keys and make money when you cant use it. Act fast as this one wont last!

125  Venetian Drive  For Sale, MLS 583423
$1,148,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
4 Bed, 4 Baths, 2,173 SqFt Days Listed: 292
-3.93% ($47,000) 2 Price Changes : Last Change 127 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: 70ft.

Villa Morada. Enjoy the phenomenal Islamorada lifestyle in this just completed Home! Everything New! 3 Bedrooms / 2 Baths upstairs and lovely, legal 1/1 guest suite, downstairs with separate entry. Stunning open stainless and granite kitchen, huge Living Room. Metal Roof, Rare Garage, and full Veranda overlooking the picturesque canal help make this home special. This Keys Oasis is ideal for entertaining. With 70 Feet of dockage. and super proximity to both Florida Bay/ Gulf and the Ocean, your boat can spirit you away to world class fishing and diving. Fantastic White Marlin Beach Community with its own rare sandy beach! THIS is your Bucket List Opportunity!

81906  Overseas Highway  5 For Sale, MLS 580100
$1,150,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 525
+4.55% ($50,000) 1 Price Change : Last Change 132 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

NEW CONSTRUCTION. CORAL COVE an intimate gated community of 9 site-built homes in the heart of downtown Islamorada. Bayfront with boat basin and dock, each home has its own private pool, state of the art amenities and details plus light and bright natural stone and wood finishes and just steps away from all that Islamorada has to offer.Developers are FL licensed real estate agents.

126  Bessie Road  For Sale, MLS 580681
$1,194,000
Plantation Key
Tropical Atlantic Shores   - MM: 90.00
4 Bed, 4 Baths, 1,980 SqFt Days Listed: 483
-4.40% ($55,000) 2 Price Changes : Last Change 97 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift65ft.

Calling all families and friends looking for two separate complete living spaces Up and Down! 4 bedrooms and 2 baths, nearly 2,000 square feet of living space. Turn Key, completely updated and renovated waterfront home, including all new electrical and plumbing! Ocean side with direct ocean access. Located In Plantation Key (Islamorada) next to Tavernier Creek, this concrete home including the roof, boasts all impact glass windows , neutral porcelain tiles, custom wood cabinetry, open concept living with bar, Spa style bathrooms, granite counter tops, stainless appliances, extensive brick pavers, a fully fenced yard with custom aluminum work, professional landscaping, electric retractable sunshade, new outdoor kitchen with chiseled travertine , tiki hut at waters edge, 1 Hr to MIA.

305  North Drive  For Sale, MLS 582775
$1,195,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
3 Bed, 3 Baths, 2,345 SqFt Days Listed: 336
-7.72% ($100,000) 1 Price Change : Last Change 224 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 68ft.

Tucked away in the exclusive Plantation Lake Estates private and gated community, this 3B/3B, immaculate gem is the perfect island retreat. This impressive, Islamorada garden house is situated in the most tranquil setting with expansive lake-front views from all levels, including the expansive Widows Walk. Deep-water dockage, straight shot out to the open ocean, plus easy access to the bay via Snake Creek. 2B/2B, plus loft upstairs and a full 1B/1B plus kitchenette downstairs. Storage galore inside and outside. House is set up to receive generator power. Included in the real property sale price is the bromeliad & most of the orchid collection and all attached to trees staghorn ferns. Some furniture negotiable.

193  Gulfview Drive  For Sale, MLS 585745
$1,199,000
Lower Matecumbe
Port Antigua   - MM: 74.50
4 Bed, 4 Baths, 2,545 SqFt Days Listed: 148
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift60ft.

This fabulous Port Antigua home is ready for a new family to enjoy! Vaulted tongue in groove ceilings and clerestory windows in the open living area let in the natural light. Features include travertine floors throughout, 3 Bedrooms and 2 baths on the main living level, separate laundry room/pantry and another bedroom and bath on the ground level. The downstairs is above flood and permitted, making this a large home for guests and extended family to share! The backyard is accented with pavers and leads to the 60 ft. concrete dock with a 20,000 lb. boatlift. The carport and garage give protected storage for golf carts, jet skis, etc. The Port Antigua Homeowners Park offers a beautiful sandy beach with tiki huts and BBQ grills for property owners as well as a boat ramp within the community.

138  Venetian Drive  For Sale, MLS 586483
$1,349,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
4 Bed, 4 Baths, 2,670 SqFt Days Listed: 93
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Great privacy across the waterway... Overlooking an approximately 62 acre tract of environmentally sensitive land and offering quick access to bay and ocean, this canalfront, fully concrete, two-story, pre-firm home offers lots of outdoor entertaining space...Newly thatched, huge waterfront chickee, newly surfaced dock with low maintenance composite decking, plus 12,000 lb boat lift & jet-ski lift for your convenience. Spacious interiors, tastefully finished & fully furnished... 2 bedrooms, 2 baths up with large, newly surfaced sundeck, and 2 bedrooms, 2 1/2 baths down. Voluntary homeowners association offers a lovely bayfront homeowners beach for fun in the sun!

167  Harbor Drive  For Sale, MLS 587273
$1,349,000
Plantation Key
Tropical Atlantic Shores   - MM: 90.00
3 Bed, 3 Baths, 1,686 SqFt Days Listed: 35
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat LiftConcrete

This home has it all! 85 ft. of concrete dock, with a 15,000 lb boat lift, located on a deep water canal featuring an excellent location just 3 houses in from Tavernier Creek giving you direct ocean & bay access. There are 2 bedrooms & 2 bathrooms upstairs & 1 bedroom & 1 bathroom downstairs. New Swimming Pool, new roof, new pavers, new fence, new addition on upper level, plus lower level guest quarters, fish cleaning station, outdoor shower, storage with an ice machine & refrigerator and so much more!

158  Biscayne Boulevard  For Sale, MLS 584578
$1,399,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,069 SqFt Days Listed: 225
-8.50% ($130,000) 1 Price Change : Last Change 49 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift,Boat Slip

LOCATION,LOCATION, LOCATION...Rare find, just steps away from the bay with direct access.This property is located in a very desirable location in Port Antigua. This 3 bedroom 2 bath remodeled home has a private beach and boat ramp. Custom wood cabinetry with Island, stainless steel appliances, Travertine fireplace, Vaulted Ceiling, florida room with sliding glass doors that open up to the bay views and a deep water dockage with boat lift and cleaning station. downstairs has an extra room with storage with all your fishing needs. Seller is motivated and will entertain offers.

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 10-14-2019.

Shoreline Properties
92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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