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Islamorada Waterfront Homes For Sale on the Ocean Side

Most of the properties in the Florida Keys peninsula are either on the ocean side or on the bay / gulf side of the island. The following Waterfront Islamorada homes for sale below are on the ocean side.

Total Listings 19
Order By:

$349,000
Plantation Key
Plantation By The Sea   - MM: 87.50
2 Bed, 2 Baths, 989 SqFt Days Listed: 73
-3.03% ($10,900) 1 Price Change : Last Change 4 Days Ago
Condo - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

NEW TO THE MARKET - Plantation by the Sea, top floor townhouse with ocean views. Take your pick from THREE outdoor porches or watch the sunrise from the ocean-front dock. On the first floor you have the kitchen, large living room, half bath and a porch with gorgeous views of the Atlantic Ocean and swaying palms. The second floor features two large bedrooms, 1 full bathroom and more views of the water. Unit has a brand new AC and hot water heater. The complex offers a heated pool, large fishing pier, club house/game room, sauna and gym...all with fabulous views of the ocean! Covered parking space and large, ground level storage room is also included in purchase.

$800,000
Lower Matecumbe
Mate Lido Beach   - MM: 76.00
4 Bed, 4 Baths, 1,677 SqFt Days Listed: 220
-3.03% ($25,000) 1 Price Change : Last Change 72 Days Ago
Single Family - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: 75ft.

CHARMING WATERFRONT concrete home in desirable Lower Matecumbe with immediate Atlantic Ocean access and easy Bay access to enjoy all the offshore and backcountry fishing and great waterfront dining. Spacious 4bd/3ba home offers an open living area, new kitchen and new roof. Substantial 75 of concrete dockage. You will appreciate all the character this Keys style home offers. You will enjoy living the peaceful FL Keys Lifestyle!

$1,299,999
Windley Key
Anglers Reef   - MM: 85.00
2 Bed, 2 Baths, 1,620 SqFt Days Listed: 77
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Other Dockage

Anglers Reef 2 bedroom 2.5 bath home with a large side lot. The lot has a hurricane proof storage shed for storing your fishing gear & water toys & plenty of room for entertaining guests. The home feature include 3 porches, impact windows & doors, a metal roof, a gorgeous kitchen with viking appliances, wood cabinets, granite counter tops, wood floors in the bedrooms & tile floors in the living area. Anglers Reef is a private gated community with 52 homes. Amenities include gated entryway, a marina, community pool on the Ocean, 2 sandy beaches & quaint streets to take walks. The home qualifies for Transient Rentals which allows the owner to basically own the home with a positive cash flow depending on owner usage.

$1,795,000
Plantation Key
Plantation Beach   - MM: 87.50
4 Bed, 4 Baths, 3,000 SqFt Days Listed: 80
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 225ft.

Looking for serenity with ocean views and privacy? Look no further! Custom built Cedar Home with Ocean Views on 3/4 of an acre with a pool. Surrounded by 225 ft of water frontage and ocean breezes - pure tranquility. Perfect for entertaining or for a large family. High ceilings, large rooms, great entertainment areas, teak cabinets, bar overlooking the water - this home is the perfect Keys home.

$2,000,000
Plantation Key
Plantation Lake Estates   - MM: 87.00
3 Bed, 3 Baths, 2,309 SqFt Days Listed: 10
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Gated. This is a highly sought after community. Simply the best location, exclusive & extremely private. This is the most Beautiful, Beach Home. A rare find & rarely available in the Prestigious, Plantation Lake Estates. Prime location at Mile Marker 87 across from Founders Park with an on site boat ramp and park. A stunning great room w/ a gorgeous coral fireplace and souring wood beam ceilings; all overlooking the glistening Atlantic Ocean. Priceless views & sunrises. Three inviting bedrooms including a third floor master en-suite with a private porch to gaze at the moon and stars. Large eat in working kitchen for all your entertaining needs & a downstairs, large rec room with a cabana kitchen for indoor-outdoor entertaining as well. Please confirm all info on MLS.

$2,399,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
4 Bed, 4 Baths, 1,562 SqFt Days Listed: 90
-7.73% ($201,000) 1 Price Change : Last Change 25 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Dock Privilege

This stunning home located In Coral Cove, a gated community in Downtown Islamorada, overlooks a private lagoon and the ocean. The property features 4 bedrooms, 3 baths, custom cabinetry, marble floors and countertops, a jacuzzi tub on the large porch, many outdoor entertaining spaces and fishing off the private, backyard dock. This small enclave of homes offers private, protected boat dockage in its ocean-front basin, a large pool with a view of Alligator Lighthouse and gorgeous, lush landscaping. There is boat dockage for a skiff or bay boat on the lagoon side of the house and dockage for up to 35 in the private boat basin (first-come basis). Coral Cove is a quick drive or walk to many of Islamoradas best restaurants and shops.

$2,750,000
Plantation Key
Plantation Beach   - MM: 87.50
4 Bed, 4 Baths, 2,499 SqFt Days Listed: 40
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Concrete

This is a very secluded ocean access poured concrete 3 level 4 bedroom 3 1/2 bath home on private island with 11 elevation. (NO STORM DAMAGE) deep water lagoon (22). almost an acre surrounded by water. plenty of parking and an air-conditioned single garage with laundry area. remodeled kitchen with granite counter tops, stainless steel appliances, Gas 5 burner stainless stove and convection oven. 58 bottle wine cooler. Double sink on one side and a larger deep sink on the other! Over and under lighting and a great island with bar area perfect for entertaining! Very large living area 32 X 16 All windows recently (last year) replaced, several impact. Solid wood hand carved doors, all different! 2 large 17 x 13 bedrooms on main level plus full bath and powder room.

$3,250,000
Lower Matecumbe
Mat Ocean View   - MM: 76.50
3 Bed, 3 Baths, 2,408 SqFt Days Listed: 67
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: NoneRip Rap

Expand your horizons with ocean vistas from every room in this totally renovated gated 1/2-acre mini-estate offering 80 of ocean frontage. In true Florida Keys lifestyle, bask by the beautiful brand new pool with heater and chiller, surrounded by travertine decking and native landscaping. The welcoming entrance features an elevator which services all three levels of this 2408 sf, 3 bedroom, 3 1/2 bath custom home. The first level offers a sensible floor plan and showcases the generous wrap-around porch, the perfect spot to entertain and enjoy sparkling ocean views. The well-appointed kitchen boasts Bosch and Kitchen-Aid appliances, with Cambria countertops ...

$4,250,000
Upper Matecumbe Key Islamorada
Unplatted Upper Mate   - MM: 82.00
3 Bed, 3 Baths, 2,749 SqFt Days Listed: 44
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None,Other Dockage

Gecko Estate, boasts 2.9 luscious acres, of some of the most beautiful land the Florida Keys has to offer, with mature vegetation. Situated on the Ocean, in Islamorada, this lovely estate offers 178 of ocean-frontage, with protected seawall, an elegant pool with screened enclosure, its own private island, beach and protected dockage (destroyed in Hurricane Irma - Buyer to rebuild). A private gated entry, with long winding driveway, invites one to meander through 3 very pristine parcels of land, including bay-bottom where one can collect treasures washed ashore. Enjoy gorgeous sunrises year-round, a quick jaunt to Alligator Lighthouse for sunsets, Cheeca Rocks, live reefs and more to snorkel, dive, fish or just enjoy a leisurely boat ride from this supreme location.

$4,450,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 3,866 SqFt Days Listed: 28
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

BEAUTIFUL GATED OCEANFRONT ESTATE! Located on 1.8 acres in Islamorada featuring amazing ocean views, 5 bedrooms, 4 full bathrooms, winding interior staircase, expansive ocean view porches, over 3,800 sf of living space, pool, beach area ,observation dock, storage, gated entrance, and beautiful soaring palm trees. Enjoy the ocean breezes and spectacular sunrises. Excellent rental property with a weekly rental license.

$4,450,000
Lower Matecumbe
Mat Ocean Beach   - MM: 75.00
4 Bed, 4 Baths, 3,011 SqFt Days Listed: 28
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

Paradise Beach House! Endless open water Views surround this lovely Key West style ocean front estate, enjoy your natural walk-in sandy beach, spectacular sunrises, private saltwater pool and spa with lush tropical landscaping for your privacy! Beautiful Custom Built Home with great attention to detail, cherry hardwood flooring throughout, open floor plan with breakfast nook, dining, bar living area, perfect for entertaining, great chef kitchen with granite/stainless appliances and gas stove. Master bedroom with luxurious bath, jetted tub and private balcony overlooking pool and beach! Excellent weekly rental investment home offering 4 bedrooms and 4 full baths, with a cozy loft, this private, gated home is certainly a must see treasure.

$4,750,000
Windley Key
Unplatted Windley Key   - MM: 88.00
3 Bed, 3 Baths, 1,839 SqFt Days Listed: 84
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin

Fabulous Fishermans Lair! This spectacular ocean front property is located in Islamorada on over 2 acres of prime ocean front property with a 50 x 223 ft. irreplaceable boat basin. The property features 200 ft. of ocean front offering direct bay & ocean access. This property is located just 3 miles from the Gulf Stream and offers direct bay access via channels without direct ocean exposure. Larger boats have direct access to Snake Creek. The concrete ground level home has 3 bedrooms & 2 bathrooms with a large deck & chickee hut overlooking the tropical crystal clear island waters. There is ample storage with a/c and a private office. This is Truly a one of a kind Private Island Oasis!

$5,950,000
Upper Matecumbe Key Islamorada
Caribee Beach   - MM: 80.00
6 Bed, 6 Baths, 2,635 SqFt Days Listed: 294
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift100ft.

CARIBEE BEACH HOUSE is the perfect mix of old school Islamorada charm combined with present-day, stylish luxuries. One of the few oceanfront estates with a deep water basin and its own channel allowing access for larger vessels. 200 of shoreline with a sandy beach and fabulous views of Alligator Lighthouse. The 100 dock features a 24k lb boatlift and the irreplaceable concrete jetty has a boathouse and 4,500 lb lift for your skiff. The main house is 3 bedrooms / 3 bathrooms and is fully renovated. The new guesthouse is 3 bedrooms / 2 bathrooms and has a 3 bay garage on the first floor. Fully fenced-in and gated, a custom putting green, heated and chilled pool, zipline, and biking distance to everything Islamorada has to offer, makes for a perfect package! The property has the space and

$6,000,000
Plantation Key
Key Heights   - MM: 88.50
4 Bed, 4 Baths, 4,103 SqFt Days Listed: 303
+20.00% ($1,000,000) 1 Price Change : Last Change 34 Days Ago
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Boat Lift400ft.Concr

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires Row... Islamoradas premier address. New dock with two new boat lifts (16,000 lb. and 10,000 lb.) to enjoy one of the best boating locations in the Keys, plus a 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 great income potential.

$7,900,000
Plantation Key
Key Heights   - MM: 88.50
5 Bed, 5 Baths, 5,457 SqFt Days Listed: 523
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: 100ft.Concrete

Expansive oceanfront family estate compound never before offered for sale! Known as Plantation House, this unique property was once the star of the Islamorada Tour of Homes and was featured for its 2.5+ acres of tropical gardens complete with numerous manicured foot paths lined with coral stones. As one of Islamoradas exclusive Millionaires Row properties, the homes entrance is privately gated and offers a winding paved driveway meandering through the trees and opening to reveal the 5,457 sf home with oceanfront pool, elevator, deep dockage, sandy beach, private boat ramp and endless ocean views. The permit has been approved to replace the damaged dock in its previous footprint, including the gazebo at the end. This one-of-a-kind property is ready to refresh and make your own!

$7,900,000
Upper Matecumbe Key Islamorada
Strattons   - MM: 82.50
8 Bed, 8 Baths, 4,931 SqFt Days Listed: 119
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: None

FairWinds~A unique two acre walk in the water oceanfront estate, located in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, along with many amenities. Inside the gates are enchantingly lush tropical gardens with carefully cultivated native specimens leading to the shimmering pastel blues of the Atlantic ocean, which gently caresses the 250+ feet of secluded sandy beach. This very special compound blends privacy with abundant recreational opportunities, ideally suited to create cherished memories with family and friends. Complete with a grand main house with a wrap-around porch, wide verandas and stunning ocean views, perfect for memorable gatherings of family and friends. Watch the sun rise beyond the historic Alligator Reef Lighthouse just a few

$8,300,000
Plantation Key
Lake Harbor   - MM: 89.00
5 Bed, 5 Baths, 6,269 SqFt Days Listed: 643
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: Basin,Boat Lift,Davi

Welcome to Mima Grada... your Florida Keys oceanfront dream estate with everything you desire to live the ultimate island life. Enjoy your own private boat basin with boat lift and jet ski davits, sprawling sandy beach, lagoon-style pool/spa with poolside tiki bar, private lighted tennis court, and of course expansive ocean views. This spacious beach mansion stands out as one of the most elegant on Islamoradas Millionaires Row, which is an eclectic collection of unique open water estates all with distinctive entry gates, winding driveways and lush tropical foliage. Enjoy the serenity and privacy of Mima Grada with your immediate family or feel free to invite all your friends with plenty of room for entertaining both inside and out including two private guest suites. Must see!

$11,900,000
Plantation Key
Plantation Beach   - MM: 87.50
5 Bed, 5 Baths, 7,813 SqFt Days Listed: 299
Single Family - Active - Waterfront Yes
Side of Island: Ocean - Dockage: n/a

Built in 2006 and situated on over 10 acres off of the Old Highway on Plantation Key, this estate is luxury at its finest with a private and gated entrance. The property is nestled right on the Atlantic Ocean with 450 ft. of beach frontage and features some of the most beautiful tropical landscaping consisting of Sea Grape trees, and yellow and red Royal Poinciana trees, to name a few. Nestled between the main house and the guest house is a heated pool and hot tub designed with Keystone deck to complete the island feel of the exterior of the property. The aesthetic of the main and guest house resembles a Southern manor combined with regal Caribbean touches and attention to detail. The main house offers 6,652 sq. feet, where the third story is home to a grand master suite and an additional

$13,000,000
Upper Matecumbe Key Islamorada
Tea Table   - MM: 79.50
5 Bed, 5 Baths, 3,104 SqFt Days Listed: 752
-13.33% ($2,000,000) 4 Price Changes : Last Change 119 Days Ago
Off Shore Isl - Contingent - Waterfront Yes
Side of Island: Ocean - Dockage: Davits40ft.

An extremely rare and stunning private island, accessible by car, Terras Key is a gated Caribbean Island located at Mile Marker 79.7 in Islamorada. Jutting into the blue-green waters of the Atlantic Ocean, Terras Key features a 2,000+- driveway enabling you to reach restaurants and shopping easily.Enjoy the conveniences of the modern world, including all utilities, while surrounded with the privacy of your own +15.5 Acre Island with miles of open water views and views of Alligator Reef Light. The compound includes 5 bedrooms and 4 baths, pool, cabana, dockage, and a tennis court. This extraordinary private island is a landmark in Islamorada and the Florida Keys and has not been offered for sale for over 27 years.

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 06-13-2021.

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92300 Overseas Hwy Suite 303
Key Largo, Florida 33070

1(800) 692-3605
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