All Islamorada Waterfront Homes for Sale

BAYFRONT SERENITY ON PLANTATION KEY! Welcome to Redwing Road on the north end of Plantation Key in Village of Islands offering remodeled Tri-level home directly on Florid...

Gorgeous single family home now available in Indian Waterways! This turnkey waterfront homes features a 60' dock, above flood lower level, & a spacious floor plan includi...

Enjoy the unique & special enclave that is Plantation Point, one of Islamorada's most pristine & private communities. Offering the ultimate peaceful retreat with only 3 h...

This home is the definition of 'Keys' living. Situated on an oversized lot this 3 bedroom, 3 bath home offers 68 feet of dockage including a 10,000 lb. boat lift, a spaci...

Rare opportunity to own a Bayfront property on Islamorada's most prestigious street, Indian Mound Trail. This house is situated for breathtaking sunset views. The large b...

OPPORTUNITY AWAITS ~ Oceanfront Estate property package. Why have 2 acres when you can have almost 5 acres & exceptional opportunities? TWO contiguous prime OCEANFRONT P...

Privacy abounds at this immaculate, Islamorada canal front home with protective dockage, peekaboo ocean view and rare homeowner access to a white sandy beach. Located in ...

Casa Oceania is a secluded oceanfront estate on Millionaire's Row that satisfies the senses and eases the soul. With 250 ft. of private oceanfront, 360 roof terrace to wa...

Ocean's Dream ~ Absolutely sublime oceanfront pool home estate. You will be entranced from the moment you enter the property with the lushly landscaped gated entrance th...

This is a remarkable opportunity to own an updated waterfront home that is being sold furnished including the TV's! This home has approximately 35 feet of protected dock...

Immediate ocean access w/ deep water dockage! Located in gated community. LARGE boat harbor provides protective dockage & privacy in your backyard. Concrete dock on top o...

Perfect Bayside Getaway! Incredible point lot on deep water canal in the Upper Keys-Plantation Key-Tavernier. Outside the canal is a beautiful bay where people cruise, sn...

This stunning 3.14 acre property is situated in the heart of Islamorada's millionaire row. Weekly rentals are allowed which is externally hard to come by! 2 wraparound ba...

THIS IS IT! The turn-key Florida Keys canal home you have been waiting for! Bright & airy concrete home with impact windows and 59 feet on a wide, clean canal - just a fe...

BRAND-NEW custom built canal front home located in the highly desirable area of Kahiki Harbor. Very easy access to the bay and the ocean via the Tavernier Creek. Property...

Completely remodeled in 2021, no detail has been overlooked! Upstairs a stunning open kitchen featuring quartz counters, pantry, washer/dryer closet, large island for sea...

The perfect vacation or forever home! This charming 2 bedroom, 2 bath home has everything you need to live the Florida Keys lifestyle. With 2 boat lifts (15,000lb & 7,000...

Anglers Reef Direct Oceanfront home with deeded dock #11. This home features 2 huge bedrooms, 3 bathrooms, a carport & 3 porches. Located on the community pool with endle...

Bring your Tito's and your toothbrush! Nothing left to do except kick back and enjoy this Venetian Shores concrete home with 100 feet of deep water dockage including cut...

Gated Estate Residence encompassing entire peninsula with over 500feet of bayfront and protected crystal clear waters. This pristine private luxury resort style property...

Islamorada canal front on Lower Matecumbe Key. This 3 bedroom/ 2 bathroom home offers a split floor plan. Primary ensuite has a walk-in closet with custom shelving, slide...

Location, Location! In the fabulous Florida Keys in the Village of Islamorada is the most desirable neighborhood of Venetian Shores offering fantastic boating with deep ...

Location! Location! Location! Islamorada, the 'sport fishing capital of the world!' Oceanside CBS construction with concrete roof. This unique property includes a most...

Incredible opportunity to purchase a totally renovated 4-bedroom 2 1/2 bath CBS home in Islamorada's Indian Waterways with a 70' concrete dock! Ideally located on the ba...

Gorgeous-- 6Bd/4 Bath All Concrete Home on the water. 75 Ft. of Deep water canal Dockage. Beautiful Fenced -In Pool, surrounded by Wooden Deck ,Hot-tub & Tiki-Bar. In Pre...

This Fantastic Venetian Shores pool home is ready for a new family to enjoy living their best Keys life! The main living level opens to the pool deck and dock and featur...

Located in Anglers Reef on Windley Key, this two-story Old Florida style home is complete with 31' BOAT SLIP and carport plus Vacation rental history. This unit is comp...

100' CONCRETE DOCKAGE on 100' wide canal in desirable VENETIAN SHORES! SPACIOUS CONCRETE home offering an open living floor plan and 2bd/2ba upstairs along with an expan...

Welcome to the Beach House, offering forever ocean views from Lower Matecumbe Key. This 4 bedroom / 4 bath home with 3,200sf of living space plus an additional 1,600sf of...

Breathtaking Ocean Views located in Islamorada!! Rare 2 bedroom and 2 bath stilt home with multi-million-dollar views without the price tag located in Windley Key Park. N...

Imagine a luxurious island estate not only defined by its exclusive gated entrance, but also by its private dock, separate guest house and endless sunset celebrations. A ...

Located on desirable Lower Matecumbe, this sweet and simple conch cottage is ready for your next chapter. Ready to scale back and simplify? This sweet house is 'just enou...

Completely renovated gated home in the heart of Islamorada. Heated Pool. 2Bed/ 2Bath upstairs with an Ensuite Master Bath w/ dual vanity, spa tub, glass enclosed shower a...

Port Antigua Beauty, located in a premier waterfront community in Islamorada, with an outstanding bayfront community beach and boat ramp. This CBS home features 2 bedroom...

Beautiful concrete oceanfront estate in coveted Lower Matecumbe Beach. Large lot of over a 1/2 acre, plus 1/2 acre submerged lands parcel. Enjoy endless water views and b...

OPEN HOUSE 7/2 11:00-1:00, ACCEPTING BACK UP OFFERS!Located in a desirable neighborhood, this unique completely updated property has direct water access to the bay and o...

PALM HARBOR is one of the most exquisite and incomparable estates in all of the Florida Keys. Hemmingway would have been inspired beyond imagination, both on land and sea...

Welcome to paradise! Located in the most desired location on Plantation Key, millionaires row, which is positioned on the Old Highway. This property captures the best in ...

This is a one of a kind Port Antigua home on the cul-de-sac with over 220 ft. of concrete dock and 2 boat lifts. Beautiful hand carved mahogany doors open to a gracious ...

''Tranquility in Tavernier''Upon entering through the grand foyer you will experience sweeping waterfront views from each living level of this custom and newly remodeled,...

Safety Harbor pool home with 200 ft. of canalfront and a nature preserve across the canal! 2 separate 100 ft. wide lots with no unity of title, completely fenced with 3 ...

BOATERS DELIGHT! Dock your boat at this waterfront 4 bedroom home located in the highly desirable Indian Waterways neighborhood in Islamorada. Over (+/-)80' of dockage wi...

Anglers Reef Direct Oceanfront home with deeded dock for sale. This home features 3 bedrooms, 3 bathrooms with carport & 3 porches. Located on the community pool with end...

This updated Port Antigua home with 85 ft. of concrete dock is ready for a new family to enjoy. The open floor plan and vaulted ceilings make this house feel so welcomin...

FairWinds~A unique two acre walk in the water oceanfront estate, located in downtown Islamorada on Upper Matecumbe Key. FairWinds reflects elegance, beauty, seclusion, al...

Amazing home in great subdivision with direct ocean access. This home has been completely redone from top to bottom and nothing was spared. 75 feet of deep water dockage ...

First time offered for sale... the most exclusive spot in Islamorada's most exclusive gated community! This open bayfront Old Florida home rests on nearly half an acre wi...

The perfect canal front home you have been waiting for! Spacious, freshly painted, well crafted and beautifully maintained 4 bedroom 3 bath home in sought after Ventetian...

Welcome to Mima Grada... your Florida Keys open oceanfront dream estate with everything you desire to live the ultimate island life. Enjoy your own private boat basin wi...

Outstanding Oceanfront Estate!As you pass through the double gates and begin your drive on the reclaimed brick driveway you enter a park-like setting. Upon arrival at the...

Oceanside Tranquility has plentiful views and privacy abound!Built in 2006 and situated off the Old Highway, this estate is luxury at its finest. A private and gated entr...

Islamorada Bay-Front Dream Home with fabulous sunsets nightly! This fabulous home has it all. Dockage for several boats, two boat lifts, a private, grotto pool, game room...

Isla on the Bay ~ Nestled in its own sanctuary with over 500 feet on the bay and 5.82 acres, a rare jewel is under construction. Coming soon in a sought-after and rare Is...

Open Oceanfront Estate with Deep Water Dockage on 1.5 Acres on Millionaires' Row... Islamorada's premier address. New dock with two new boat lifts (16,000 lb. and 10,000 ...