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 115
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144  Bayview Drive  For Sale, MLS 573791
$3,395,000
Lower Matecumbe
Safety Harbor   - MM: 74.00
3 Bed, 3 Baths, 3,805 SqFt Days Listed: 1126
-12.93% ($504,000) 18 Price Changes : Last Change 68 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin113ft.

Beyond compare, this Polynesian inspired exquisite keys waterway Harum Designed custom home is 99% complete, pool is in, landscaping is underway. This spectacular home is not to be missed if you are looking for a yachtsmans location w/over 110ft of deep water dockage w/unlimited beam on deep water Hurricane Creek. Cathedral ceilings grace this masterpiece and its 3 bedroom and 3.5 baths is complimented by custom LED lighting, drop down TV. Incredible storage, 2 garages, generous and spacious covered gathering areas. The residence boasts an extraordinary creekside covered balconies overlooking Hurricane Creek with views of the Florida Bay making this a Florida Keys Treasure. The finished work detail is to much to list. Contact agent for full details and showing appointment.

110  Bayview Isle Drive  For Sale, MLS 574354
$2,850,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 3,240 SqFt Days Listed: 1093
-22.97% ($850,000) 4 Price Changes : Last Change 117 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift140ft.

ANCHORS AWEIGH - 140 of deep-water, protected, concrete/paved dockage is enjoyed at this serenely secluded property with sunset views. It is rare to find 2 adjoining lots in Venetian Shores with beautiful bay views, and convenient, direct access to Snake Creek. Remodeled in 2005 & designed to take advantage of magnificent views from every level. Downstairs rec room also used as 5th bedroom.

88547  Old Highway  For Sale, MLS 576121
$4,500,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 961
+4.65% ($200,000) 6 Price Changes : Last Change 492 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift,Davits400f

Open Oceanfront Estate with Deep Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. Brand new dock with two new boat lifts to enjoy the best boating in the Keys! Spacious 4,103 s.f. home with 4 bedrooms, 3 full baths, a large heated pool, winding private driveway, and a soaring central atrium surrounded by walls of windows to frame the ocean view. Open ocean views from the living room, Florida room, porches, master bedroom and upstairs loft. Living room with wet bar and pass-through window to the gourmet kitchen and separate dining room, all with Saturnia stone floors. Direct boating access to the best offshore fishing and diving, plus quick Florida Bay access. RE Zoning allows weekly rentals for income potential. Call today!

82994  Overseas Highway 23 For Sale, MLS 579971
$2,499,000
Upper Matecumbe Key Islamorada
Penn Key Club   - MM: 83.00
3 Bed, 3 Baths, 1,812 SqFt Days Listed: 658
-28.60% ($1,001,000) 5 Price Changes : Last Change 38 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Dock P

A classic Islamorada retreat. This private home is located in the exclusive bayfront gated community of Pen Key Club in the heart of Islamorada. The lovely one-story home offers three bedrooms and three bathrooms with panoramic views of the open water from every angle. Enjoy magnificent sunsets while relaxing in the living room or charming sitting areas on the open bay. In addition, the Pen Key Club offers a pool and boat dockage in a protected boat basin. This offering is Florida Keys living at its finest!

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: 651
+4.55% ($50,000) 1 Price Change : Last Change 258 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: 609
-4.40% ($55,000) 2 Price Changes : Last Change 223 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.

298  South Drive  For Sale, MLS 581391
$3,990,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
4 Bed, 4 Baths, 3,938 SqFt Days Listed: 560
-20.04% ($1,000,000) 4 Price Changes : Last Change 126 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift38ft.

This Islamorada Gem is located in a very private ocean front enclave. The open living/dining area over looks the ocean with 20 ceilings through floor to ceiling windows. Both master suites open to ocean view terraces. A luxurious den with 50 flat screen Apple TV is a quiet retreat. All levels are serviced by elevator. Situated on a gated 1/2 acre lushly landscaped lot with paver drive and two car garage, this home is one of only 4 in the enclave. The 38 protected dock has 20K LB lift in the HOA marina. The new marina park is newly landscaped. Concrete pool and spa has new equipment. A fully equipped poolside bar has new appliances including stainless grill, refrigerator and Ice maker. Quality construction with West Indies design. Offered furnished.

139  Gimpy Gulch Drive  For Sale, MLS 582483
$8,900,000
Plantation Key
Misc Plantation Key   - MM: 85.00
6 Bed, 6 Baths, 6,573 SqFt Days Listed: 479
-6.27% ($595,000) 1 Price Change : Last Change 106 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Basin

Opulent, alluring and meticulously detailed, this Islamorada Estate is where perfection meets the Bay ~ welcome to The Fish Ranch. Located on Plantation Key, The Fish Ranch estate features two (2) single family residences plus a media house, and cabana with outdoor kitchen. World-class designs make this one of the more distinguished estates for the most discriminating buyer. Elevator shaft, 100 swimming pool with two beach entries, hot tub, 250 of sandy beach, putting green, dockage, architectural designed landscaping with fire pit and lighting throughout. Also included with this property is an additional 19,729sf lot.

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: 462
-7.72% ($100,000) 1 Price Change : Last Change 349 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 are the bromeliads, all of the orchid collection and all staghorn ferns attached to trees.

77521  Overseas Highway BLDG 6 For Sale, MLS 583305
$1,595,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 2,736 SqFt Days Listed: 427
-5.90% ($100,000) 1 Price Change : Last Change 136 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Dock Privileges

EGRET Residence: Brand new construction! This oceanfront home is stunning! The Tarpon Point community is gated and lushly landscaped with amenities such as oceanfront pool, beach, dockage and full service all home generators. This spacious 4 bedroom 4 bath home also comes with an elevator giving access to all floors of the home. The kitchen is equipped with high end

77521  Overseas Highway BLDG 8 For Sale, MLS 583312
$1,724,000
Lower Matecumbe
Matecumbe Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 2,719 SqFt Days Listed: 426
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

The Heron House at Tarpon Point overlooks the ocean front pool and offers open water ocean views. This spacious 4 bedroom, 4 bath home is well appointed with custom cabinetry, granite counters and elevator. Chefs kitchen with stainless steel appliances and dual-fuel Wolf range. Whole house generator, California closets and impact resistant windows and & doors. Amenities include beach, dock, tropically landscaped gated community. Call for your tour today.

75900  Overseas Highway  For Sale, MLS 583768
$18,000,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
7 Bed, 7 Baths, 6,198 SqFt Days Listed: 397
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Boat Lift

Nestled in six tropical acres on the bay in Islamorada on Lower Matecumbe Key is this rare parcel boasting over 600 feet of white sand beach and deep water dockage. This spectacular private estate offers 6,198 square feet of living space with six bedrooms and six-and-a-half bathrooms. The guest home offers an additional 418 square feet with one bedroom and one bathroom. Enter down a private driveway cocooned by tropical landscaping and arrive on the doorstep of this stately island-style residence. The distinctive design and craftsmanship are evident upon entering. This one-of-a-kind estate was designed to take in the captivating bay views from every room. Offering an elegant living room, formal dining room, comfortable family room and spacious sunroom with vaulted ceilings.

257  Sunset Drive  For Sale, MLS 584078
$1,990,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
3 Bed, 3 Baths, 1,674 SqFt Days Listed: 381
-20.37% ($509,000) 2 Price Changes : Last Change 209 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

One of the best values in all of the Florida Keys in a much sought-after location. Being sold by the homes second owner. The first owner was the builder and architect. The home has been completely upgraded and is ready to enjoy. Sit on the deck and watch the fish swim by, or wade out and hook up. This is a true beach house, with endless ocean views, silky sand beach, and clear Atlantic waters to enjoy. This home has the infrastructure to add a third floor for additional space and views. Upstairs there is one bedroom and one bathroom with a large laundry closet space. Downstairs is comprised of two bedrooms and one bathroom. Both levels offer large porches overlooking the Atlantic Ocean and the propertys beautiful beach with views of the sunrise and sunset.

262  Sunset Drive  For Sale, MLS 584415
$3,600,000
Lower Matecumbe
Lower Mat Beach   - MM: 74.00
4 Bed, 4 Baths, 2,835 SqFt Days Listed: 361
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift90ft.

Mesmerizing water views from just about every room in this four-bedroom, three-and-a-half bathroom home including downstairs guest quarters. This beautiful house with beach access has a multitude of amenities such as natural coral accents, a gourmet kitchen with custom wood cabinetry, double ovens, and bar seating. The wonderful outdoor living spaces include an in-ground pool with a heater, chiller, lights and a waterfall, and terraces with open ocean views. Additional amenities include dockage for two boats, electric shutters, a multi-car garage, a workshop, and an elevator with etched glass artistry. The third floor is all master suite with elevator access, dual walk-in closets, an office, a sitting area, a spacious master bathroom, and two balconies for sunrise and sunset views.

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: 351
-8.50% ($130,000) 1 Price Change : Last Change 175 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.

77521  Overseas Highway 3 For Sale, MLS 584594
$1,995,000
Lower Matecumbe
Mat Ocean Bay   - MM: 75.00
4 Bed, 4 Baths, 2,894 SqFt Days Listed: 351
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Marlin House is a stunning brand new 4 bedroom, 4 bath home in Islamorada that features top of the line amenities and stunning ocean views from all living levels of the home. As you enter the gates of Tarpon Point you will find an exclusive enclave of 12 oceanfront residences. Designed to meet the ultra-high standards of the developer, these exceptional homes allow for the most advanced building techniques to reside in harmony with one of the worlds few remaining untouched and fully protected marine habitats. Once you enter Marlin House and make your way to the main living level you will be in awe of the ocean views that greet you upon entering the living area. Located just off the living area is the dining room and chefs kitchen. On this level you will also find the first of

80531  Old Highway  For Sale, MLS 584600
$3,200,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,044 SqFt Days Listed: 351
-17.29% ($669,000) 2 Price Changes : Last Change 58 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other DockageCo

Motivated Seller! Owner Finance Possible! One-of-a-kind 3 plus-acre estate on Upper Matecumbe Key. You will follow the classic brick driveway to one of Islamoradas most private settings. The main house, (above the flood zone), offers two bedrooms and two-and-a-half bathrooms, featuring high beamed ceilings, tile floors, and ocean views. A guest cottage offers one bedroom, one bathroom, and a large sitting room. Watch the colors of beautiful sunrises and incredible sunsets reflect off Alligator Lighthouse from all rooms. Look for tailing bonefish and wading birds, or just sit by the pool and relax--Mother Nature is your living room. A caretakers cottage as well as a guest cottage can be added to the property as of right. Two additional lots have the possibility to be rezoned

104  Gulfside Drive  For Sale, MLS 585020
$2,399,000
Plantation Key
Venetian Shores   - MM: 86.00
4 Bed, 4 Baths, 2,792 SqFt Days Listed: 322
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: Assigned Dock,Boat L

This Venetian Shores Bay Front home offers all concrete construction, metal roof, impact windows, and a third floor living plan that takes advantage of the spectacular Bay views. Open living room, quality kitchen with ice machine and wine cooler, and screened-in patio, all with views that impress. Convenient foyer entry with elevator access to all floors. Assigned boat slip in the Marina with an 8,000 lb. boat lift 1 house away, landscaped yard, garage, floating dock for your wave-runners in the backyard. Huge screened in patio with concrete swimming pool. Offered fully furnished making this truly a turn-key property. Quality, beauty, and location!

  South Drive  For Sale, MLS 585035
$6,300,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
5 Bed, 5 Baths, SqFt Days Listed: 322
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Other Dockage2

This is an incredible real estate land opportunity on the ocean side of Plantation Key known as Plantation Point South. This 9-acre, estate property boasts of approximately 750 feet of shoreline bordering a secluded, conservation parkland with a sandy beach. Build your new, custom home high atop terraced land, positioned to take full advantage of the propertys spectacular ocean views. The elevation of this building site allows for ground level construction making it the perfect setting for a family compound to pass down to future generations. Approximately 400 feet of sandy beach below offers an abundance of sky-high coconut palms with permit to add a pier leading to your very private oceanfront observation platform with a day bed.

75180  Overseas Highway  For Sale, MLS 585065
$1,595,000
Lower Matecumbe
Unplatted Lower Mate   - MM: 76.00
3 Bed, 3 Baths, 1,803 SqFt Days Listed: 320
-10.89% ($195,000) 3 Price Changes : Last Change 159 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Bay/Gulf - Dockage: n/a

Awesome, bayfront, property on Lower Matecumbe with everything a family needs to enjoy the Keys lifestyle! Deep water dockage, natural private sand beach, endless bay views, tiki hut with bar, and thats just outside. Inside enjoy travertine floors, media room, custom glass etched bar, cargo lift, separate laundry room and remolded 1/1 downstairs . Perfect for any fisherman the property is conveniently located with endless access to inshore angling and a short run to ocean with no fixed bridges. Owner financing possible and a realistic price make this a must see. More photos coming soon!

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 02-17-2020.

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Key Largo, Florida 33070

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