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All Islamorada waterfront homes Real Estate Search

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All Islamorada Waterfront Homes for Sale

Homes for sale on Plantation Key, Windley Key, Upper Matecumbe Key and Lower Matecumbe Key.  Homes are located on canal, bayfront or oceanfront lots.

Contact me to set up a custom search to find just the type of Florida Keys property that suits your needs.

Islamorada Homes for Sale

74960 Overseas Highway Unit ##2, Islamorada image
74960 Overseas Highway Unit ##2, Islamorada $3,279,000

Sea Oats, at Seabreeze Cove, is a pre-construction residence, designed to enjoy the full ocean views offered across Sea Oats Beach and also offers a backyard, tropical sa...

  • 4 Beds
  • 5 Baths
  • 594889 MLS
74960 Overseas Highway Unit ##1, Islamorada image
74960 Overseas Highway Unit ##1, Islamorada $3,279,000

Windswept, at Seabreeze Cove, is a pre-construction residence, designed to enjoy the full ocean views offered across Sea Oats Beach and also offers a backyard, tropical s...

  • 4 Beds
  • 5 Baths
  • 594887 MLS
127 Sapodilla Drive, Islamorada image
127 Sapodilla Drive, Islamorada $4,500,000

Escape to paradise! This stunning main 3BD/6BA plus 1BD/1BA guest house offers idyllic island living in a private and relaxing residence. Gated for extra privacy, unwin...

  • 4 Beds
  • 7 Baths
  • 594881 MLS
2 Flamingo Hammock Road, Islamorada image
2 Flamingo Hammock Road, Islamorada $2,399,000

Bay Hammocks is a unique, secluded Hidden Paradise with 33 home sites in a gated boat access community. THE GREAT ESCAPE. Enjoy a modern Brand-New Coastal Design Home com...

  • 4 Beds
  • 5 Baths
  • 594832 MLS
424 Palm Drive, Islamorada image
424 Palm Drive, Islamorada $1,999,000

Perfect mix of Keys' styling with a touch of modern, this all-concrete home has undergone a full renovation with all high-end finishes and no shortcuts taken. Privacy abo...

  • 4 Beds
  • 3 Baths
  • 594795 MLS
107 Redwing Road, Tavernier image
107 Redwing Road, Tavernier $1,750,000

COME EMBRACE THIS BEAUTIFULLY REMODELED solid concrete canalfront home in Plantation Key! Spacious 4bd/3ba, legal living quarters down, open living floor plan. Quartz co...

  • 4 Beds
  • 3 Baths
  • 594763 MLS
209 E Carroll Street, Islamorada image
209 E Carroll Street, Islamorada $7,900,000

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...

  • 5 Beds
  • 3 Baths
  • 594692 MLS
83265 Old Highway, Islamorada image
83265 Old Highway, Islamorada $2,750,000

Welcome to Morada Sands, the pinnacle of beachfront living! Traditional coastal cottage styling with an ultra modern kitchen; impeccably finished with tongue in groove ce...

  • 3 Beds
  • 2 Baths
  • 594642 MLS
75900 Overseas Highway, Islamorada image
75900 Overseas Highway, Islamorada $13,900,000

Your own private escape! On nearly 4 acres in Islamorada with natural beach, this magnificent estate sets a new standard of island living. Enter your gates, past your ten...

  • 7 Beds
  • 8 Baths
  • 594632 MLS
143 Columbus Drive, Islamorada image
143 Columbus Drive, Islamorada $2,699,000

True paradise awaits with this stunning oceanfront, beach property on Lower Matecumbe Key in Islamorada. Tastefully decorated with a coastal motif, this home was complet...

  • 3 Beds
  • 2 Baths
  • 594604 MLS
106 Harbor Drive, Tavernier image
106 Harbor Drive, Tavernier $849,000

Canal Front Home with easy Ocean or Bay Access through Tavernier Creek. This 3 bedroom, 2 bathroom Stilt Home is enhanced with Unique Cypress Siding, a 58 ft Concret...

  • 3 Beds
  • 2 Baths
  • 594598 MLS
137 Sapodilla Drive, Islamorada image
137 Sapodilla Drive, Islamorada $4,300,000

Here's your chance to live on one of the most prestigious streets in Islamorada! Situated on a large, deep-water lagoon with protected dockage, this spacious home is a co...

  • 5 Beds
  • 6 Baths
  • 594593 MLS
106 Milano Drive Drive, Islamorada image
106 Milano Drive Drive, Islamorada $1,450,000

PRESTIGIOUS VENETIAN SHORES!! Move-in ready two-story modern & spacious , all concrete updated 3 bedroom 3 bath home on 70ft frontage of deep& wide open water canal, 20...

  • 3 Beds
  • 3 Baths
  • 594560 MLS
100 Gulfside Drive, Islamorada image
100 Gulfside Drive, Islamorada $2,495,000

VENETIAN SHORES BAYFRONT POOL HOME, all concrete construction, concrete roof, new impact windows and doors, boat slip directly next to home with boat lift (slip allows fo...

  • 3 Beds
  • 3 Baths
  • 594483 MLS
232 Apache Street, Tavernier image
232 Apache Street, Tavernier $1,395,000

The perfect Keys house located on a canal with direct bay access. This home has been updated and offers a pool with hot tub, outdoor kitchen, impact windows and doors, a ...

  • 3 Beds
  • 2 Baths
  • 594477 MLS
3 Flamingo Hammock Road, Islamorada image
3 Flamingo Hammock Road, Islamorada $2,479,000

Bay Hammocks is a unique, secluded Hidden Paradise with 33 home sites in a gated boat access community. Enjoy a modern Brand-New Design Home completed in 2020. This luxu...

  • 4 Beds
  • 4 Baths
  • 594476 MLS
96 W Plaza Del Sol, Islamorada image
96 W Plaza Del Sol, Islamorada $2,050,000

Be the first to Move in to this Newly constructed 3000 sq ft home located in Port Antigua just steps away from your private sandy community beach. Enjoy all the comforts ...

  • 4 Beds
  • 4 Baths
  • 594435 MLS
72 W Plaza Del Sol, Islamorada image
72 W Plaza Del Sol, Islamorada $1,499,000

Shipshape waterfront home with a 60 ft concrete dock on a wide, clear-water canal. Access to Port Antigua homeowners' boat ramp and private white sandy beach on the Flori...

  • 3 Beds
  • 2 Baths
  • 594431 MLS
429 S Coconut Palm Boulevard, Tavernier image
429 S Coconut Palm Boulevard, Tavernier $1,900,000

This home checks all the boxes! Pool, 20,000 lb. boatlift, shaded fish cleaning station, rooftop deck for sunset views, workshop/storage, interior staircase and a fenced ...

  • 4 Beds
  • 3 Baths
  • 594420 MLS
88747 Old Hwy Highway, Islamorada image
88747 Old Hwy Highway, Islamorada $2,799,000 ▼

Exceptional Property On Millionaires Row! The home is located on 1.47 acres offering 3 bedrooms & 2.1 bathrooms, screened porch, dockage with a boat lift, roof top deck,...

  • 3 Beds
  • 3 Baths
  • 594295 MLS
122 Spoonbill Road, Tavernier image
122 Spoonbill Road, Tavernier $2,590,000

Every so often a home comes on the market that lacks a weakness, and that is this home. Whether it be location, quality of construction, or functionality you are looking ...

  • 3 Beds
  • 2 Baths
  • 594280 MLS
122 Bessie Road, Tavernier image
122 Bessie Road, Tavernier $1,100,000

Relax and Revitalize in this Rare Find!!! Stylishly appointed concrete home situated on an oversized lot on a wide, clean, shimmering canal. Boating is a breeze with easy...

  • 3 Beds
  • 3 Baths
  • 594241 MLS
155 Severino Drive, Islamorada image
155 Severino Drive, Islamorada $3,950,000

PIRATE'S DEN in Venetian Shores directly on Snake Creek! Avast, look no further... This is the one-of-a-kind point property you have always admired while boating in Isla...

  • 4 Beds
  • 3 Baths
  • 594231 MLS
140 Gimpy Gulch Drive, Islamorada image
140 Gimpy Gulch Drive, Islamorada $1,895,000

Rare Opportunity! Very unique ''Tree House'' with Panoramic Bay Views, protected Dockage, and lots of Old Florida Charm! Home is located at the end of a private road, off...

  • 2 Beds
  • 2 Baths
  • 594155 MLS
101 San Remo Drive, Islamorada image
101 San Remo Drive, Islamorada $1,575,000

Venetian Shores Canalfront 4 bed/4 bath home with 70 ft. dock offering near instant boating access to both the Atlantic Ocean and Florida Bay. This spacious Islamorada ho...

  • 4 Beds
  • 4 Baths
  • 594123 MLS
179 Venetian Way, Islamorada image
179 Venetian Way, Islamorada $1,850,000 ▼

This Bayfront Key West style home located in the sought-after Plantation Key neighborhood of Venetian Shores, sits on 3/4 of an acre and offers privacy, and lush landsc...

  • 4 Beds
  • 4 Baths
  • 594049 MLS
75651 Overseas Highway, Islamorada image
75651 Overseas Highway, Islamorada $1,289,000

Oceanfront duplex on 112 linear feet of expansive natural sand beach with gorgeous ocean views. 2 Bedrooms, 1 Bath, Full Kitchen, Dining Area and Living Room in EACH of t...

  • 4 Beds
  • 2 Baths
  • 594035 MLS
41 Columbus Drive Unit #Ext., Islamorada image
41 Columbus Drive Unit #Ext., Islamorada $2,100,000

Barefoot elegance at its best. Sensual, seductive, and sublime, are but a few of the ways to describe this phenomenal Florida Keys beachfront oasis. Rare, hardpacked sand...

  • 2 Beds
  • 1 Baths
  • 593945 MLS
223 Pueblo Street, Tavernier image
223 Pueblo Street, Tavernier $789,000

This 2 bedroom, 2 bath house was updated in 2017. Sliding glass doors slide into wall area for unobstructed view of back yard and canal. Large screened in patio great for...

  • 2 Beds
  • 2 Baths
  • 593926 MLS
100 Stromboli Drive, Islamorada image
100 Stromboli Drive, Islamorada $2,850,000

Boaters Paradise awaits in this 3920 AC square foot Venetian Shores home with Bay-views, dock, pool, spa(heated or chilled) & garage! This spacious 5 bedroom 4.5 bath hom...

  • 5 Beds
  • 5 Baths
  • 593918 MLS
197 Nautilus Drive, Islamorada image
197 Nautilus Drive, Islamorada $799,000

White Marlin Beach Lower Matecumbe! Deep water dockage canal front 3 bedroom and 2 bath home with 1288 as ft of living space with an open floor plan in an excellent loca...

  • 3 Beds
  • 2 Baths
  • 593912 MLS
305 North Drive, Islamorada image
305 North Drive, Islamorada $1,295,000

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 ga...

  • 3 Beds
  • 3 Baths
  • 593899 MLS
120 Villa Bella Drive, Islamorada image
120 Villa Bella Drive, Islamorada $2,138,500

Exceptional Venetian Shores home with 100ft. dock and views of Snake Creek! Move right in to this 5 bedroom beauty with an ELEVATOR! Featuring a private master suite on t...

  • 4 Beds
  • 4 Baths
  • 593890 MLS
138 Plantation Boulevard, Islamorada image
138 Plantation Boulevard, Islamorada $4,700,000

Location, casual Keys elegance, irreplaceable boat basin and stunning Bay views. Immediately upon entry, your senses will overwhelm you as you pierce the driveway and pas...

  • 3 Beds
  • 2 Baths
  • 593849 MLS
126 Tequesta Street, Tavernier image
126 Tequesta Street, Tavernier $850,000

Canalfront 3 bedroom, 2 large bathroom, stilt home with 55 ft wooden dock in Tavernier. Screened patios off living area and primary bedroom suite. Easy Florida Bay and At...

  • 3 Beds
  • 2 Baths
  • 593720 MLS
59 W Plaza Del Sol, Islamorada image
59 W Plaza Del Sol, Islamorada $1,900,000 ▼

Port Antigua 5 bedroom 3 bath CBS home on a wide deep canal, with a full 75 Ft. dock, a 12,000 Lb. boat lift and davits. New metal roof, impact windows just recently in...

  • 5 Beds
  • 3 Baths
  • 593610 MLS
230 Mohawk Street, Tavernier image
230 Mohawk Street, Tavernier $870,000 ▼

Beautifully remodeled canal front 3 bedroom, 2.5 bath home in Islamorada. CBS Construction, metal roof, impact windows and doors and propane insta hot water heater. Circu...

  • 3 Beds
  • 3 Baths
  • 593503 MLS
121 Villa Bella Drive, Islamorada image
121 Villa Bella Drive, Islamorada $1,950,000

Located in Premier Waterfront Neighborhood, Venetian Shores! Solid concrete construction home with new metal roof, large in-ground pool and entertaining area, elevator, t...

  • 3 Beds
  • 3 Baths
  • 593500 MLS
87 Plaza Del Sol, Islamorada image
87 Plaza Del Sol, Islamorada $1,495,000

Modern and spacious 3 bedroom 2 bath with 65ft of dockage on gin clear canal in Port Antigua awaits you. 1990 construction, vaulted ceilings, tiled throughout living area...

  • 3 Beds
  • 2 Baths
  • 593365 MLS
138 Venetian Way, Islamorada image
138 Venetian Way, Islamorada $659,000

One owner home on kayaking canal-above flood level-ground level home. Priced to sell in Venetian Shores! This 4 Bedroom 2.5 Bath ground floor home will amaze you with ext...

  • 4 Beds
  • 3 Baths
  • 593356 MLS
81486 Overseas Highway, Islamorada image
81486 Overseas Highway, Islamorada $8,450,000

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...

  • 7 Beds
  • 9 Baths
  • 593287 MLS
118 Sea Lane, Islamorada image
118 Sea Lane, Islamorada $800,000 ▼

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 ...

  • 4 Beds
  • 3 Baths
  • 593283 MLS
195 Kahiki Drive, Tavernier image
195 Kahiki Drive, Tavernier $1,700,000

THIS IS A RARE FIND located directly on Tavernier Creek offering deep-water dockage making it a perfect location for the avid boater with immediate ocean access for fabul...

  • 3 Beds
  • 2 Baths
  • 593241 MLS
147 Sonny Road, Tavernier image
147 Sonny Road, Tavernier $799,000 ▼

PRICE REDUCED!!! Someone is about to get a great deal on this clean home with 75' of dockage and direct ocean and Tavernier Creek access. Separate 2/1 up and 2/1 guest qu...

  • 4 Beds
  • 2 Baths
  • 592871 MLS
81212 Old Highway, Islamorada image
81212 Old Highway, Islamorada $999,000

A magical, modern new island-style villa with very private pool patio awaits your arrival. Located on the Old Road at Mile Marker 81.2 along Morada Way. WATERFRONT boat ...

  • 2 Beds
  • 3 Baths
  • 592800 MLS
169 Indian Mound Trail, Tavernier image
169 Indian Mound Trail, Tavernier $4,950,000

CASA DEL SOL- Ultimate bayfront private luxury estate offers flawless open water views and painted sky sunsets. 75' concrete deep water dock just a stone's throw from Sna...

  • 4 Beds
  • 5 Baths
  • 592762 MLS
77521 Overseas Highway Unit #5, Islamorada image
77521 Overseas Highway Unit #5, Islamorada $1,595,000

Oceanfront home in premiere gated Islamorada community. This 4 bedroom, 4 bath home has it all. Three stories of extraordinary views accessible via formal stairwell or ta...

  • 4 Beds
  • 4 Baths
  • 592757 MLS
88561 Old Highway, Tavernier image
88561 Old Highway, Tavernier $3,200,000

Moja Draga Estate - Croatian for ''My Darling'' is a piece of paradise in the fabulous Florida Keys. Located on the Old Road (also known as Millionaire's Row) in beautifu...

  • 3 Beds
  • 3 Baths
  • 592421 MLS
80101 Overseas Highway, Islamorada image
80101 Overseas Highway, Islamorada $5,950,000

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 bas...

  • 6 Beds
  • 5 Baths
  • 592212 MLS
88011 Old Highway, Islamorada image
88011 Old Highway, Islamorada $11,900,000

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 ...

  • 5 Beds
  • 6 Baths
  • 592156 MLS
88547 Old Highway, Islamorada image
88547 Old Highway, Islamorada $5,000,000

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 ...

  • 4 Beds
  • 3 Baths
  • 592095 MLS
113 Ponce De Leon Boulevard, Islamorada image
113 Ponce De Leon Boulevard, Islamorada $1,735,000 ▼

Your island pool home awaits in Islamorada's Port Antigua! 3 bedrooms, 3 baths, high ceilings, tile & hardwood floors, state of the art kitchen w/ concrete counters & to...

  • 3 Beds
  • 3 Baths
  • 592069 MLS
264 S Coconut Palm Boulevard, Islamorada image
264 S Coconut Palm Boulevard, Islamorada $1,300,000 ▼

**NOW ACCEPTING BACK UP OFFERS!**Waterfront Updated home in Islamorada, built in 1997! Beautiful, spacious-- 2,070sf of living area-- 3 bedroom (room for a 4th!), 2 bath,...

  • 3 Beds
  • 2 Baths
  • 592027 MLS
109 Sapodilla Drive, Islamorada image
109 Sapodilla Drive, Islamorada $1,300,000

This property is situated on an oversized lot with ocean views on one of the most sought-after streets in Islamorada. Located on Sandy Cove Basin, a protected and private...

  • 3 Beds
  • 4 Baths
  • 591957 MLS
126 Bessie Road, Islamorada image
126 Bessie Road, Islamorada $1,349,000

Waterfront , CBS Ocean Side Home, NEW POOL COMING SOON! 2 complete living spaces Up and Down! 4 bedrooms and 2 baths, nearly 2,000 square feet of living space. Turn Key, ...

  • 4 Beds
  • 2 Baths
  • 591743 MLS
117 El Capitan Drive, Islamorada image
117 El Capitan Drive, Islamorada $2,150,000 ▼

BOATERS DELIGHT! Dock your boat at this waterfront 5 bedroom home located in the highly desirable Port Antigua neighborhood on Lower Matecumbe Key, Islamorada. With +/-...

  • 5 Beds
  • 3 Baths
  • 591615 MLS
112 White Marlin Boulevard, Islamorada image
112 White Marlin Boulevard, Islamorada $1,350,000

This double lot property is in the White Marlin Beach neighborhood with HOA park access. Extensive upgrades include new dock, new impact doors and windows, new roof with ...

  • 3 Beds
  • 3 Baths
  • 591613 MLS
75051 Overseas Highway, Islamorada image
75051 Overseas Highway, Islamorada $1,999,999 ▼

A unique oceanfront home situated on one of the most ideal locations on Lower Matecumbe. As you enter through the mahogany doors, you find a remodeled kitchen, timeless g...

  • 3 Beds
  • 5 Baths
  • 591165 MLS
439 Palm Drive, Islamorada image
439 Palm Drive, Islamorada $1,300,000

Delightfully Keysey POOL home in Safety Harbor with Bay Views! This home has a wonderful open floor plan and 2 large bedrooms and 2 baths upstairs. The living area opens ...

  • 4 Beds
  • 3 Baths
  • 591150 MLS
162 Harbor Drive, Islamorada image
162 Harbor Drive, Islamorada $1,295,000 ▲

Ocean side canal on Tavernier Creek, immediate Ocean & Bay access from 85' feet of concrete dock . Full concrete construction including the roof. Large open living area w...

  • 4 Beds
  • 2 Baths
  • 591054 MLS
179 Iroquois Drive, Islamorada image
179 Iroquois Drive, Islamorada $1,600,000

Have a large family? Need an In-Laws suite? Need 110' of dockage with a total of 190' of water frontage? Need a large garage? This home can meet any one of those needs! C...

  • 4 Beds
  • 4 Baths
  • 590725 MLS
75055 Overseas Highway, Islamorada image
75055 Overseas Highway, Islamorada $1,440,000

Escape to your own sandy beach, gated for secluded privacy, this 3 bedroom 2 bath home offers open ocean views from the master bedroom, spacious porch and guest bedroom, ...

  • 3 Beds
  • 2 Baths
  • 590290 MLS
201 Galleon Lane, Islamorada image
201 Galleon Lane, Islamorada $689,000

Concrete Home, Concrete Roof, Concrete Boat Dock on Treasure Harbor. There are 2 Parcels - Tract A- waterfront parcel - Concrete dock fronting on Treasure Harbor. Dock ha...

  • 3 Beds
  • 3 Baths
  • 590280 MLS
77360 Overseas Highway, Islamorada image
77360 Overseas Highway, Islamorada $2,500,000

Don't miss this unique property with deep water dockage and a pool on over an acre of land! Feel the Keys Spirit take you away as you enter the long driveway and see a l...

  • 8 Beds
  • 5 Baths
  • 590204 MLS
88663 Old Highway, Islamorada image
88663 Old Highway, Islamorada $7,900,000

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 o...

  • 5 Beds
  • 5 Baths
  • 589040 MLS
200 Atlantic Street, Islamorada image
200 Atlantic Street, Islamorada $7,900,000

Introducing Bunny Key, an extraordinary historic Islamorada oceanfront plantation. Once you enter the gate you will be entranced by the prettiest beach on the island of I...

  • 8 Beds
  • 6 Baths
  • 589035 MLS
85289 Old Highway, Islamorada image
85289 Old Highway, Islamorada $5,250,000 ▼

Build a better life at Blue Harbor. This stunning contemporary 3,035 sq. ft. retreat is nestled on 1+ acre and redefines oceanfront living. With 200 feet of deepwater doc...

  • 4 Beds
  • 3 Baths
  • 588920 MLS
88987 Old Highway, Islamorada image
88987 Old Highway, Islamorada $6,645,000 ▼

Through a long winding and manicured driveway off of the Old Highway you will enter this exquisite Seaside Villa located on Plantation Key in Islamorada, FL. Sitting on 2...

  • 7 Beds
  • 7 Baths
  • 587930 MLS
89707 Old Highway, Islamorada image
89707 Old Highway, Islamorada $8,300,000

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 bo...

  • 5 Beds
  • 6 Baths
  • 587281 MLS
75445 Overseas Highway, Islamorada image
75445 Overseas Highway, Islamorada $2,999,000 ▼

A LUXURY, OCEANFRONT ESTATE with NEW OBSERVATION PIER completed Feb. 2021! Behind the gates and concrete wall surrounding this property, greets a contemporary-remodeled (...

  • 4 Beds
  • 5 Baths
  • 586728 MLS
139 Gimpy Gulch Drive, Islamorada image
139 Gimpy Gulch Drive, Islamorada $8,490,000 ▼

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 Ra...

  • 6 Beds
  • 10 Baths
  • 582483 MLS

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Jim Signor, Broker-Associate
Coldwell Banker Schmitt Real Estate
100430 Overseas Highway
Key Largo, FL 33037

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