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 100
Order By:

84961  Old Highway 23 For Sale, MLS 585719
$499,000
Windley Key
Galen Beach   - MM: 85.00
2 Bed, 2 Baths, 705 SqFt Days Listed: 92
-13.22% ($76,000) 2 Price Changes : Last Change 7 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges,Othe

Seaside 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. This rare quaint park/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: 110
+6.40% ($40,000) 1 Price Change : Last Change 18 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.

176  Iroquois Drive  For Sale, MLS 585357
$745,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
2 Bed, 2 Baths, 960 SqFt Days Listed: 115
-3.87% ($30,000) 1 Price Change : Last Change 67 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits75ft.

Boaters Dream! This is your opportunity to own a canalfront home in Islamorada located ocean side with 75 ft. of concrete dockage. The best location in Lower Matecumbe offering quick boating access to the ocean and bay side! Home offers a fresh coastal design, tons of natural light, Split floorplan with 2 bedrooms and 2 baths, garage and tiki hut. Very spacious with a master walk-in closet and storage space. Home has been fully renovated, complete with impact doors and windows, brand-new roof and is move-in ready. Homeowner has access to a rare sea turtle nesting beach and the peek-a-boo ocean views makes this home a must-have!

202  Johnny Road  For Sale, MLS 585260
$749,000
Plantation Key
Boatmans Colony   - MM: 90.50
2 Bed, 2 Baths, 1,372 SqFt Days Listed: 122
-2.60% ($20,000) 1 Price Change : Last Change 54 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Moments to the ocean or bay, this waterfront home is right off Tavernier Creek. The homes unique features include open ceilings with exposed beams, lots of natural light, wood floors, and a huge side porch. The open chefs kitchen features a commercial double oven and gas range. On a corner lot, the property offers two parking areas, plus an RV hookup with 50 amps of power. The upstairs includes a half bathroom, and a renovated master suite with a gorgeous full bathroom. Downstairs there are two bedrooms and one bathroom. Upgrades include a newer roof and air conditioning.

106  Columbus Drive  For Sale, MLS 581716
$780,000
Lower Matecumbe
Mat Ocean View   - MM: 76.50
4 Bed, 4 Baths, 2,004 SqFt Days Listed: 353
-8.13% ($69,000) 2 Price Changes : Last Change 10 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 75ft.

World class fishing in your backyard! Canal front home with concrete dock and direct Atlantic Ocean access. CBS home on Lower Matecumbe in Islamorada offers 2 bedrooms, 2 bathrooms on main living level & stainless steel kitchen appliances. Ground level 2 bedrooms, 1 bathroom. Large yard with room for a pool. Sport fishing, diving, kayaking, boating, paddle boarding all from the 75-foot concrete dock. Easy boating access to Ocean and Florida Bay.

102  Sunset Drive  For Sale, MLS 584091
$825,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,681 SqFt Days Listed: 195
-2.83% ($24,000) 1 Price Change : Last Change 25 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Dubbed The Mosaic for its mosaic tile details around the front door and an aquatic scene on the back of the house. This precious three-bedroom, three-bathroom concrete cottage with concrete roof on Lower Matecumbe boasts a new dock with slips for multiple boats, new stainless steel appliances, impact windows, and peek-a-boo ocean views. Rare community beach access right at the end of the road. The ample outdoor space provides room for a pool or water toys.

100  Venetian Drive  For Sale, MLS 586439
$890,000
Lower Matecumbe
White Marlin Beach   - MM: 74.50
2 Bed, 2 Baths, 1,080 SqFt Days Listed: 39
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Amazing views from this immaculate 2 bedroom 2 bath home on pristine canal with access to both Bay and Ocean. Panoramic views of large conservation and lake. 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. 20 ft Dock with deck area. House is build high enough to allow doubling of square footage by enclosing downstairs area. Opened unfurnished attic for added storage space. Beautiful private homeowners beach on Bayside.

122  Valencia Drive  For Sale, MLS 586765
$899,000
Plantation Key
Tavernaero   - MM: 91.00
3 Bed, 3 Baths, 1,750 SqFt Days Listed: 16
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Updated about 10 years ago.

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: 41
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.

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: 310
-2.63% ($25,000) 1 Price Change : Last Change 89 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.

114  Sunset Drive  For Sale, MLS 585675
$950,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,456 SqFt Days Listed: 95
-4.90% ($49,000) 2 Price Changes : Last Change 18 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 60ft.

Islamorada,Waterfront, Dock, Pool, Ocean View and Beach Access, this Beach House has it all! Updated with New Windows, New Flooring, New Central A/C, New Pool, New Kitchen with New Stainless Appliances,New Landscaping! Upper level has, partially furnished 2 bedrooms,2 bathrooms, lovely screened porch overlooking the ocean, Spacious & legal One bedroom, One bath, Lower Level Guest Quarters with living room and kitchenette! Beautiful in ground pool w/ Heater, Chiller & Water Display, bonus Cabana Bath, 60 ft. of Dock with easy Ocean and Bay access. Sunset Drive ISLAMORADA, is one of the most desirable streets in The Keys offering neighborhood beach access ,adjoining lots on either side are docks for homes across the street therefore allowing lots of privacy on both sides!

217  Gulfview Drive  For Sale, MLS 584432
$965,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 2,095 SqFt Days Listed: 174
-11.39% ($124,000) 2 Price Changes : Last Change 23 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Davits688ft.Concrete

WATER VIEWS DOWN MAIN CANAL. All concrete stilt home on corner lot within walking distance to beautiful community/private sandy beachfront park. 2B/1B upstairs, kitchen, dining, living room of appx 1,429 Sqft overlooking screened tiled balcony. Views down main canal, 68+ Ft of concrete dock w/davits & fish cleaning station, room for a pool, 2 carports, permitted 1 bathroom down plus bonus room shown as lower level finished floor per tax rolls. Utility room/workshop. Great location in Port Antigua on Lower Matecumbe Key in Islamorada. A must see! Can be purchased as a package with adjoining vacant lot. See MLS#584430.

169  Venetian Way  For Sale, MLS 586426
$985,000
Plantation Key
Venetian Shores   - MM: 86.00
5 Bed, 5 Baths, 2,761 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: None

Elegant two-story contemporary design home that offers open living spaces, lots of natural light throughout, and a dream gourmet kitchen with granite countertops and high-end stainless-steel appliances. A perfect family retreat with exceptional floor plan that merges indoor and outdoor spaces. This home is beyond compare featuring high ceilings, over 16,000 square feet of breathtaking grounds, a den/office, sunroom and a bedroom wing consisting of 4 large bedrooms/ 3.5 baths. Glass doors lead to a large sparkling pool and expansive patio excellent for entertaining. Centrally located on Plantation Key in Venetian Shores this home will capture your imagination.

102  Porto Vista Court  For Sale, MLS 586230
$997,000
Lower Matecumbe
Port Antigua   - MM: 74.50
3 Bed, 3 Baths, 1,914 SqFt Days Listed: 57
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Other Dockage

This affordable beauty in Port Antigua, a premier waterfront community in Islamorada, features a fabulous bay front community beach and private residents? boat ramp is being listed under $1 million dollars for quick sale. Listing price includes the existing furniture (not the fishing rods) inside the home. The home has a concrete wall and roof featuring 2 bedrooms and 2 full baths upstairs, full bathroom downstairs with air-conditioned storage, 2 boat lifts one which holds 15,000 pounds and the 2nd one holds 7,000 pounds, impact glass doors and windows (installed 4 years ago), tile throughout both floors, and travertine tile throughout the dock. The kitchen has custom cabinetry and granite countertops. The property is a corner lot and has beautiful fruit trees with a sprinkler system.

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: 31
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.

81906  Overseas Highway  4 For Sale, MLS 580099
$1,050,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
3 Bed, 3 Baths, 1,852 SqFt Days Listed: 467
+5.00% ($50,000) 1 Price Change : Last Change 74 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.

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: 11
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!

124  Palo De Oro Drive  For Sale, MLS 585966
$1,100,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,764 SqFt Days Listed: 75
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!

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: 234
-3.93% ($47,000) 2 Price Changes : Last Change 69 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!

240  Treasure Harbor Road  For Sale, MLS 584764
$1,149,000
Plantation Key
Treasure Harbor   - MM: 86.50
4 Bed, 4 Baths, 2,300 SqFt Days Listed: 157
-9.88% ($126,000) 2 Price Changes : Last Change 12 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Davits

WATERFRONT CONCRETE HOME with OCEANVIEWS in ISLAMORADA offering DIRECT OCEAN ACCESS, perfect for the avid fishermen, snorkelers and divers, situated on a large harbour with 85 of DEEP-WATER DOCKAGE! Spacious and well-maintained 4bd/3ba with interior staircase. This home is meant for outdoor entertaining with an outdoor bar and lush tropical landscaping offering a lot of privacy along with a roof-top deck to enjoy the oceanviews. This is where you will enjoy living the FL Keys Lifestyle!

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 08-17-2019.

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

1(800) 692-3605
Contact Us