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Search All Islamorada Real Estate

Islamorada spans five islands in the Upper Florida Keys — Plantation Key, Windley Key, Upper Matecumbe, Lower Matecumbe, and Tea Table Key — running from roughly Mile Marker 90 down to MM 74. Known as the Sport Fishing Capital of the World, it draws buyers looking for oceanfront estates, canalfront homes with Atlantic and Florida Bay access, and a village character unlike anywhere else in the Keys.islamorada-real-estate

Current Islamorada Market Stats

Islamorada Single Family Statistics July 2026
Islamorada Condo Townhouse Statistics July 2026

Read my most recent Florida Keys Real Estate Market Report for 2026

Browse listings by neighborhood below. Data pulls directly from the Florida Keys MLS and updates every 5 minutes.

Curious what's selling nearby? Create a free custom market report to see active listings, pending sales, and recent closings in any Islamorada neighborhood.

  • Anglers Reef
  • Bay Hammock
  • Bay Harbour Condo
  • Bay Ridge
  • Beacon Reef Condo
  • Boatmans Colony
  • Coral Harbour Condo
  • Coral Shores
  • Davis Shores
  • Edenaire
  • Executive Bay Club Condo
  • Futura Yacht Club
  • Fontaine Lake Estates
  • Green Turtle Beach
  • Grove Park
  • High Point
  • Indian Harbor
  • Indian Waterways
  • Islamorada South Condo
  • Kahiki Harbor
  • Key Heights
  • Lake Harbor
  • Lower Matecumbe Beach
  • Maison Matecumbe Condo
  • Mar Celeste
  • Mate Lido Beach
  • Matecumbe Ocean Bay
  • Matecumbe Ocean Beach
  • Matecumbe Ocean View
  • Matecumbe Sandy Beach
  • Ocean Harbour Condo
  • Palms of Islamorada Condo
  • Pen Key Club
  • Plantation Beach
  • Plantation by the Sea Condo
  • Plantation Key Colony
  • Plantation Ridge
  • Plantation Shores
  • Plantation Tropical Park
  • Plantation Villas Condo
  • Plantation Lake Estates
  • Port Antigua Townhouse
  • Port Antigua
  • Port of Call Townhouse
  • Randall Adams
  • Safety Harbor
  • Sea Gulls Condo
  • Stillbeach
  • Strattons
  • Summer Sea Condo
  • Sunshine Estates
  • Tarpon Flats
  • Tavernaero
  • Toll Gate Shores
  • Treasure Harbor
  • Tropical Atlantic Shores
  • Tropical Coral Reef
  • Vacation Village
  • Venetian Shores
  • White Marlin Beach

Contact Jim Signor to get help narrowing your search or to talk through what's moving in a specific neighborhood or price range.

For sale in Islamorada

75433 Overseas Hwy, Islamorada image
75433 Overseas Hwy, Islamorada $3,999,000

Wake up to the sunrise over the Atlantic from this private oceanfront retreat offering two separate residences, a sandy beach, and direct access from Highway to Ocean. T...

  • 4 Beds
  • 4 Baths
  • 621270 MLS
88540 Overseas Highway Unit 716, Tavernier image
88540 Overseas Highway Unit 716, Tavernier $1,800,000

RARELY AVAILABLE AT FUTURA YACHT CLUB! This beautifully remodeled end-unit townhome offers an exceptional Florida Keys lifestyle, complete with two side-by-side deeded bo...

  • 2 Beds
  • 3 Baths
  • 621264 MLS
124 Orchid St, Tavernier image
124 Orchid St, Tavernier $2,849,000

Exceptional Brand New Waterfront Home in a prime Plantation Key location. This striking three-level contemporary residence offers 60 feet of protected deep-water dockage...

  • 4 Beds
  • 4 Baths
  • 621261 MLS
160 Ridge St, Tavernier image
160 Ridge St, Tavernier $810,000

This home is special and just waiting for the next family to make memories here. Tucked among lush tropical landscaping, this inviting Islamorada home offers the perfect...

  • 4 Beds
  • 2 Baths
  • 621221 MLS
88500 Overseas Highway Unit 407, Tavernier image
88500 Overseas Highway Unit 407, Tavernier $487,500

Welcome to your Florida Keys retreat at Summer Sea! Enjoy bay views from your private open deck area. This 2-bedroom, 1.5-bath condo offers updates throughout and coastal...

  • 2 Beds
  • 2 Baths
  • 621201 MLS
124 Coral Ave, Tavernier image
124 Coral Ave, Tavernier $739,000

CBS home on a large lot in Islamorada's desirable Edenaire! This concrete 2 bedroom, 2 bath house has a metal roof, impact windows and doors, and is in an X flood zone. H...

  • 2 Beds
  • 2 Baths
  • 621182 MLS
313 North Dr, Islamorada image
313 North Dr, Islamorada $3,700,000

Private. Luxurious. Waterfront. Boater-focused. This is more than a home it is an opportunity to experience the Florida Keys exactly as they were meant to be enjoyed. T...

  • 3 Beds
  • 3 Baths
  • 621153 MLS
130 Palm Ln, Islamorada image
130 Palm Ln, Islamorada $2,250,000

Welcome to your private island home retreat, The Belle House. Highlighted on the Netflix series Bloodline as the home of Kevin & Belle Rayburn. Set on an expansive half-a...

  • 3 Beds
  • 3 Baths
  • 621121 MLS
114 Spoonbill Rd, Tavernier image
114 Spoonbill Rd, Tavernier $2,100,000

Newly renovated 3-bedroom, 2-bath canal-front CBS home with direct bay access. The interior has been fully updated with tasteful coastal finishes, along with new impact w...

  • 3 Beds
  • 2 Baths
  • 621120 MLS
107 Valencia Dr, Islamorada image
107 Valencia Dr, Islamorada $2,500,000 ▼

OCEAN ACCESS WATERFRONT OPPORTUNITY IN VENETIAN SHORES! Immaculate 2-story CBS concrete home offering the ultimate Florida Keys lifestyle! Situated on a 100' wide deep-wa...

  • 3 Beds
  • 3 Baths
  • 621119 MLS
148 Giardino Dr, Islamorada image
148 Giardino Dr, Islamorada $3,952,000

THIS UPDATED BEAUTY LOCATED IN RENOWNED VENETIAN SHORES IS A TRUE MUST SEE!! LOCATED IN ONE OF VENETIAN SHORES MOST EXCLUSIVE LOCATIONS GIARDINO DRIVE. UPSTAIRS: THREE ...

  • 5 Beds
  • 3 Baths
  • 621117 MLS
200 Wrenn St Unit PH 701, Islamorada image
200 Wrenn St Unit PH 701, Islamorada $999,988

OCEANFRONT PENTHOUSE -- STRONG RENTAL INCOME. Welcome to PH701 at Sea Gulls, a rare and incredibly unique 3-bed, 2-bath oceanfront penthouse. With over 2,100 sq ft of liv...

  • 3 Beds
  • 2 Baths
  • 621110 MLS
100 Iroquois Dr Unit Unit 5, Islamorada image
100 Iroquois Dr Unit Unit 5, Islamorada $999,999

This waterfront home offers 36 feet of dockage and a beautifully renovated interior designed for effortless Keys living. Thoughtfully updated and tastefully decorated, th...

  • 3 Beds
  • 3 Baths
  • 621101 MLS
350 Buttonwood Bight Ln, Tavernier image
350 Buttonwood Bight Ln, Tavernier $14,000,000

The most sought-after bay in all the Florida Keys, and one of the largest properties on it. This true double lot spans 1.3 acres with more than 250' of bayfront facing du...

  • 5 Beds
  • 4 Baths
  • 621096 MLS
87200 Overseas Hwy Unit J 6, Islamorada image
87200 Overseas Hwy Unit J 6, Islamorada $999,000

Discover easy bayfront living in this beautifully updated townhome at Executive Bay Club, where breathtaking views of Florida Bay take center stage. The open living area ...

  • 3 Beds
  • 2 Baths
  • 621074 MLS
316 North Dr, Islamorada image
316 North Dr, Islamorada $2,400,000

Simply the best location, exclusive & extremely private. This is a rare find and a single-family home that's rarely available. It's tucked away in the prestigious ''Plant...

  • 3 Beds
  • 4 Baths
  • 621073 MLS
87851 Old Hwy Unit APT M5, Islamorada image
87851 Old Hwy Unit APT M5, Islamorada $1,300,000

A New Standard of Paradise - Live with views of the Atlantic Ocean everyday. This home has been updated and beautified from top to bottom. Marble flooring throughout livi...

  • 2 Beds
  • 2 Baths
  • 621009 MLS
87455 Old Hwy Unit 248, Islamorada image
87455 Old Hwy Unit 248, Islamorada $427,000

BEAUTIFUL CONDO WITH OCEAN VIEWS FOR LESS THAN $430,000! LIVE THE DREAM IN THIS OCEANFRONT RESORT STYLE PROPERTY IN THE HIGHLY DESIRABLE PLANTATION BY THE SEA ON THE OCE...

  • 2 Beds
  • 2 Baths
  • 620997 MLS
144 N Rolling Hill Rd, Islamorada image
144 N Rolling Hill Rd, Islamorada $6,195,000

Experience the ultimate Islamorada waterfront lifestyle in an exceptional contemporary custom bayfront residence, designed by its current owners, with sophisticated archi...

  • 4 Beds
  • 5 Baths
  • 620986 MLS
155 Plantation Ave, Islamorada image
155 Plantation Ave, Islamorada $2,000,000

Canal front living, right where you want it. Set along one of Islamorada's most popular canals, this turnkey 3-bedroom, 3-bath home offers a waterfront setup that makes l...

  • 3 Beds
  • 3 Baths
  • 620970 MLS
75751 Overseas Hwy, Islamorada image
75751 Overseas Hwy, Islamorada $11,000,000

Extraordinary opportunity to own one of the Florida Keys' most spectacular oceanfront residences. Set along a breathtaking stretch of pristine shoreline, this remarkable ...

  • 5 Beds
  • 5 Baths
  • 620965 MLS
207 Hibiscus St, Tavernier image
207 Hibiscus St, Tavernier $749,000

BEAUTIFUL PLANTATION KEY COLONY 2BR-2BA CBS Block Construction with a Brand New Metal Roof, featuring a PRIVATE COMMUNITY BOAT RAMP with a Low Voluntary $250 Yearly Fee a...

  • 2 Beds
  • 2 Baths
  • 620947 MLS
136 Aregood Ln, Islamorada image
136 Aregood Ln, Islamorada $795,000 ▼

Island Opportunity is knocking! Enjoy your own Islamorada vacation home...with the option to generate excellent rental income when you're not using it. Set in a private, ...

  • 2 Beds
  • 3 Baths
  • 620945 MLS
82779 Old Hwy Unit 1, Islamorada image
82779 Old Hwy Unit 1, Islamorada $4,750,000

Villa 1 offers one of the most coveted locations within the exclusive 22-villa community at The Islands of Islamorada. Ideally positioned as the closest oceanfront villa ...

  • 4 Beds
  • 5 Baths
  • 620933 MLS
121 Severino Dr, Islamorada image
121 Severino Dr, Islamorada $3,000,000

Welcome to your Venetian Shores retreat, where relaxed coastal living meets effortless waterfront luxury. This completely updated pool home is designed for easy living an...

  • 3 Beds
  • 3 Baths
  • 620907 MLS
74049 Overseas Hwy, Islamorada image
74049 Overseas Hwy, Islamorada $3,850,000

Rare opportunity to own an ocean side single family home in the heart of Islamorada. Situated on a private corner half acre lot with your own private beach, this property...

  • 4 Beds
  • 4 Baths
  • 620893 MLS
115 Fontaine Dr, Tavernier image
115 Fontaine Dr, Tavernier $650,000 ▼

ONE OF THE LOWEST PRICED HOMES IN THE VILLAGE OF ISLAMORADA! Charming Home in a desirable Plantation Key Subdivision! This well-maintained Sheffield Steel home offers e...

  • 2 Beds
  • 2 Baths
  • 620881 MLS
84961 Old Hwy Unit A1, Islamorada image
84961 Old Hwy Unit A1, Islamorada $439,000

Charming concrete bungalow in the heart of Islamorada! Move right into this beautifully updated 1BR/1BA retreat featuring fabulous ocean views from your private rooftop d...

  • 1 Beds
  • 1 Baths
  • 620845 MLS
88500 Overseas Highway Unit 208, Tavernier image
88500 Overseas Highway Unit 208, Tavernier $499,900

Welcome to Summer Seas, a desirable waterfront community in the heart of the Florida Keys! This beautifully maintained 2-bedroom, 1.5-bath condominium offers the perfect ...

  • 2 Beds
  • 2 Baths
  • 620763 MLS
168 Indian Mound Trl, Tavernier image
168 Indian Mound Trl, Tavernier $3,450,000 ▼

This exceptional waterfront estate situated on two lots and on a deep water canal with a 50ft dock is situated in the heart of Plantation Key. The property features a gra...

  • 4 Beds
  • 3 Baths
  • 620762 MLS
109 Valencia Dr, Islamorada image
109 Valencia Dr, Islamorada $4,650,000

Experience the best of the Florida Keys in this exceptional pool home, ideally situated in Venetian Shores--one of Islamorada's most coveted waterfront communities. Offer...

  • 5 Beds
  • 6 Baths
  • 620757 MLS
101 Madeira Ct, Islamorada image
101 Madeira Ct, Islamorada $2,890,000

Welcome to your coastal retreat in the highly sought-after Port Antigua neighborhood--where relaxed Keys living meets exceptional boating access and resort-style amenitie...

  • 3 Beds
  • 3 Baths
  • 620743 MLS
149 Pueblo St, Tavernier image
149 Pueblo St, Tavernier $799,000 ▼

More Space Than the Tax Records Reflect! This charming Tavernier home offers much more than meets the eye. While the tax records reflect a 2-bedroom home, the enclosed...

  • 4 Beds
  • 2 Baths
  • 620736 MLS
202 Plantation Shores Dr, Tavernier image
202 Plantation Shores Dr, Tavernier $6,000,000

Coastal Luxury. Endless Lifestyle. A rare opportunity to own an extraordinary Plantation Key waterfront estate where captivating ocean views, 140 feet of protected docka...

  • 4 Beds
  • 6 Baths
  • 620708 MLS
81250 Overseas Highway Unit 2, Islamorada image
81250 Overseas Highway Unit 2, Islamorada $2,485,000

Refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across f...

  • 3 Beds
  • 3 Baths
  • 620704 MLS
77350 Overseas Hwy, Islamorada image
77350 Overseas Hwy, Islamorada $11,700,000

Sunset Sanctuary. Natural beauty and captivating sunsets of the Florida Keys define this newly completed gated waterfront estate on Lower Matecumbe Key. Surrounded by a s...

  • 6 Beds
  • 8 Baths
  • 620680 MLS
81801 Old Hwy Unit 754, Islamorada image
81801 Old Hwy Unit 754, Islamorada $649,000

Crystal-clear turquoise waters, swaying palms, and gentle ocean breezes create the perfect Florida Keys escape. The historic Cheeca Lodge is located in the heart of Islam...

  • 1 Beds
  • 1 Baths
  • 620677 MLS
40 High Point Rd Unit 703, Islamorada image
40 High Point Rd Unit 703, Islamorada $374,000

Turn key furnished condo in Islamorada! This beautifully appointed 2 bedroom, 2 bath condo features an open floor plan, abundant natural light and a rare balcony. Remodel...

  • 2 Beds
  • 2 Baths
  • 620635 MLS
87851 Old Hwy Unit P3, Islamorada image
87851 Old Hwy Unit P3, Islamorada $1,950,000

Welcome to Ocean Harbour, one of Islamorada's premier communities! This unique 4 Bedroom, 3 Bathroom expansive 2668sqft condominium offers a desirable split floor plan wi...

  • 4 Beds
  • 3 Baths
  • 620649 MLS
81801 Overseas Highway Unit 715, Islamorada image
81801 Overseas Highway Unit 715, Islamorada $549,500

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the h...

  • 1 Beds
  • 1 Baths
  • 620633 MLS
81801 Overseas Highway Unit 716, Islamorada image
81801 Overseas Highway Unit 716, Islamorada $549,500

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the h...

  • 1 Beds
  • 1 Baths
  • 620629 MLS
157 Navajo St, Tavernier image
157 Navajo St, Tavernier $1,049,500

Gorgeous 3 bedroom 2 bathroom home on a spacious corner lot, with plenty of room for boats and RVs. Updated and remodeled bathrooms, open concept kitchen, laundry room an...

  • 3 Beds
  • 2 Baths
  • 620610 MLS
135 Tequesta St, Tavernier image
135 Tequesta St, Tavernier $1,549,000

Waterfront 3/3 Canal Home located in the Best Islamorada Plantation key Location. Great Vacation Rental is being sold furnished . Turnkey with 5 star reviews ! Large bedr...

  • 3 Beds
  • 3 Baths
  • 620538 MLS
117 El Capitan Dr, Islamorada image
117 El Capitan Dr, Islamorada $3,100,000

Newly remodeled waterfront home located in the highly desirable Port Antigua subdivision of Lower Matecumbe. This expansive residence offers five bedrooms and three bathr...

  • 5 Beds
  • 3 Baths
  • 620602 MLS
19 Avacado St, Islamorada image
19 Avacado St, Islamorada $13,750,000

Situated on one of Islamorada's premier and most sought-after bayfront streets, in the heart of Islamorada, this custom-designed poured concrete waterfront estate by reno...

  • 5 Beds
  • 7 Baths
  • 620590 MLS
88540 Overseas Hwy Unit APT 304, Islamorada image
88540 Overseas Hwy Unit APT 304, Islamorada $619,995 ▼

Welcome to Futura Yacht Club! Your island getaway awaits in this highly desirable Plantation Key community. Unit 304 is a 2 bed, 2 bath, beautifully maintained con...

  • 2 Beds
  • 2 Baths
  • 620555 MLS
157 Valencia Dr, Islamorada image
157 Valencia Dr, Islamorada $4,600,000

Located in sought-after Venetian Shores subdivision in Islamorada, this canal-front home was renovated in 2022. Sought after location - just one lot in from Snake Creek...

  • 5 Beds
  • 6 Baths
  • 620549 MLS
154 Redwing Rd, Tavernier image
154 Redwing Rd, Tavernier $3,750,000

Experience the ultimate Florida Keys waterfront lifestyle in this exceptional BayFront retreat located in the prestigious Sunshine Estates community on Plantation Key. Si...

  • 4 Beds
  • 5 Baths
  • 620543 MLS
74450 Overseas Hwy, Islamorada image
74450 Overseas Hwy, Islamorada $1,680,000

Rare Mixed-Use Opportunity with Spectacular Ocean Views in Islamorada MM 74.5. Endless possibilities await at this highly visible, commercially zoned property located ...

  • 3 Beds
  • 2 Baths
  • 620533 MLS
239 Plantation Ave, Tavernier image
239 Plantation Ave, Tavernier $2,350,000 ▼

Welcome to your slice of paradise in the village of Islamorada! This solid concrete waterfront home was completely updated in 2007 including seawall, all plumbing and ele...

  • 3 Beds
  • 3 Baths
  • 620442 MLS
195 Ojibway Ave, Tavernier image
195 Ojibway Ave, Tavernier $5,950,000

Introducing an extraordinary, newly constructed waterfront estate that must be experienced in person. Perfectly positioned on a generous 13,200 sq ft double lot with 120 ...

  • 4 Beds
  • 4 Baths
  • 620455 MLS
155 Palo De Oro Dr, Islamorada image
155 Palo De Oro Dr, Islamorada $4,500,000 ▼

An Unfinished Masterpiece Awaits in the prestigious **Venetian Shores**, one of Islamorada's most desirable waterfront communities, known for its deep-water canals and qu...

  • 3 Beds
  • 5 Baths
  • 620441 MLS
87445 Old Hwy, Islamorada image
87445 Old Hwy, Islamorada $3,995,000

Discover a rare opportunity to own an exceptional oceanfront estate in the heart of Islamorada that seamlessly combines luxury living with an established, successful vaca...

  • 5 Beds
  • 4 Baths
  • 620430 MLS
109 Giardino Dr, Islamorada image
109 Giardino Dr, Islamorada $3,875,000

Coastal elegance meets the ultimate boating lifestyle in this beautifully updated Venetian Shores home. Designed for effortless Keys living, the open floor plan is filled...

  • 4 Beds
  • 3 Baths
  • 620412 MLS
111 Spoonbill Rd, Tavernier image
111 Spoonbill Rd, Tavernier $2,999,000

Updated canal front pool home located in a desirable neighborhood with quick and easy access to the bay or ocean via Tavernier Creek, a boaters dream. It features a 3 be...

  • 3 Beds
  • 4 Baths
  • 620411 MLS
182 Airstream Ln, Tavernier image
182 Airstream Ln, Tavernier $1,250,000

Welcome to stunning Florida Bay views and breathtaking sunsets in the heart of Plantation Key! This beautifully remodeled and fully furnished modular home offers the perf...

  • 2 Beds
  • 2 Baths
  • 620396 MLS
75090 Overseas Hwy, Islamorada image
75090 Overseas Hwy, Islamorada $29,000,000

Villa Lago is an Italian-inspired waterfront estate positioned along 220 feet of pristine Florida Bay frontage in Islamorada. Offering 8,194 SF of living space on 1 acre ...

  • 4 Beds
  • 6 Baths
  • 620394 MLS
87200 Overseas Hwy Unit D3, Islamorada image
87200 Overseas Hwy Unit D3, Islamorada $599,000

Welcome to coastal living in the heart of Islamorada! This beautifully appointed townhouse in the desirable Executive Bay Club offers comfort and resort-style amenities. ...

  • 2 Beds
  • 2 Baths
  • 620393 MLS
127 & 121 Monroe Dr Unit 1-3, Tavernier image
127 & 121 Monroe Dr Unit 1-3, Tavernier $2,899,000 ▲

Exceptional investment and lifestyle opportunity in the heart of Plantation Key. This offering includes a triplex income property together with the adjacent multifamily l...

  • 4 Beds
  • 4 Baths
  • 620278 MLS
74980 Overseas Highway Unit 3, Islamorada image
74980 Overseas Highway Unit 3, Islamorada $1,890,000

Experience the ultimate Florida Keys lifestyle in this stunning split-level waterfront loft and take advantage of the vacation rental revenue. Ideally located in highly s...

  • 5 Beds
  • 3 Baths
  • 620271 MLS
87200 Overseas Hwy Unit APT A 7, Islamorada image
87200 Overseas Hwy Unit APT A 7, Islamorada $609,900 ▼

Experience the ultimate Florida Keys lifestyle in this bright and spacious townhouse-style condo located in sought-after Executive Bay Club in Islamorada. Ideally situate...

  • 2 Beds
  • 2 Baths
  • 620243 MLS
194 Buttonwood Ln, Islamorada image
194 Buttonwood Ln, Islamorada $6,150,000

Welcome to 194 Buttonwood Lane, a rare waterfront sanctuary nestled in the prestigious Safety Harbor enclave. This meticulously designed 6-bedroom, 7-bathroom residence s...

  • 6 Beds
  • 7 Baths
  • 620190 MLS
88540 Overseas Hwy Unit 101 & Boat Slip 22, Islamorada image
88540 Overseas Hwy Unit 101 & Boat Slip 22, Islamorada $1,100,000

Futura Yacht Club Rare 3 Bed/2 Bath Condo with 39 ft. Deeded Boat Slip AND 24,000 lb. Boat Lift in desirable Futura Yacht Club! Located in the heart of Plantation Key in ...

  • 3 Beds
  • 2 Baths
  • 620148 MLS
113 Villa Bella Dr, Islamorada image
113 Villa Bella Dr, Islamorada $2,550,000 ▼

Welcome to one of Islamorada's finest homes! Located in Venetian Shores the premier boating community of Islamorada. One of only two streets in the neighborhood with curb...

  • 5 Beds
  • 3 Baths
  • 620127 MLS
84961 Old Hwy Unit 41, Islamorada image
84961 Old Hwy Unit 41, Islamorada $450,000

ISLAMORADA RETREAT! Whether you're looking for a full-time residence, vacation getaway, or investment opportunity, this charming home is perfectly situated in the heart o...

  • 1 Beds
  • 1 Baths
  • 620105 MLS
139 Gimpy Gulch Dr, Islamorada image
139 Gimpy Gulch Dr, Islamorada $13,900,000 ▼

Yes, you can have it all! This one-of-a-kind 3.2 acre Islamorada bayfront estate offers a new boat dock, more than 250 feet of sandy wade-in bayfront shoreline, two full ...

  • 6 Beds
  • 9 Baths
  • 620077 MLS
89401 Old Hwy, Tavernier image
89401 Old Hwy, Tavernier $13,500,000 ▼

Private Helicopter Estate in the Florida Keys. Behind private gates on prestigious Million Air Row, this exceptional oceanfront estate spans nearly 2.5 acres and offer...

  • 8 Beds
  • 8 Baths
  • 620067 MLS
84961 Old Hwy Unit LOT 27, Islamorada image
84961 Old Hwy Unit LOT 27, Islamorada $899,000

Memories begin here. Tucked along the ocean's edge and offering the kind of lifestyle buyers spend years searching for, this one-of-a-kind oceanfront retreat delivers the...

  • 1 Beds
  • 1 Baths
  • 620039 MLS
89505 Old Hwy, Tavernier image
89505 Old Hwy, Tavernier $26,400,000

Escape to Palm Paradise, a breathtaking oceanfront estate on 7.64 private acres in Islamorada, offering 369 feet of shoreline and sweeping Atlantic views. Tucked behind g...

  • 7 Beds
  • 10 Baths
  • 620022 MLS
87455 Old Hwy Unit 244, Islamorada image
87455 Old Hwy Unit 244, Islamorada $369,000

Located in Plantation by the Sea, this Islamorada townhouse offers 2 bedrooms, 1.5 bathrooms, covered parking, and a storage unit in a gated oceanfront complex. Inside, ...

  • 2 Beds
  • 2 Baths
  • 620020 MLS
156 Monroe Dr, Tavernier image
156 Monroe Dr, Tavernier $949,000 ▼

Rare opportunity to own a half-acre corner parcel in the heart of Plantation Key. With an existing structure already in place, the property offers the flexibility for an ...

  • 3 Beds
  • 2 Baths
  • 620010 MLS
316 Woods Ave, Islamorada image
316 Woods Ave, Islamorada $2,375,000 ▼

Welcome to your own private slice of Islamorada paradise! This canal-front home offers easy access to Florida Bay along with stunning lake views and unforgettable sunsets...

  • 4 Beds
  • 4 Baths
  • 620004 MLS
154 Milano Dr, Islamorada image
154 Milano Dr, Islamorada $2,900,000 ▼

What does everyone want? The smallest house in a great neighborhood! THIS IS THE ONE! Tucked away in the sought-after Venetian Shores neighborhood of Islamorada, this ...

  • 2 Beds
  • 2 Baths
  • 619931 MLS
88500 Overseas Hwy Unit APT 424, Tavernier image
88500 Overseas Hwy Unit APT 424, Tavernier $645,000 ▼

Welcome to Summer Sea Condominium Apt 424, a beautifully remodeled and fully furnished bayfront residence in the heart of Islamorada. This turnkey, 2-bedroom, 2-full bath...

  • 2 Beds
  • 2 Baths
  • 619878 MLS
75071 Overseas Hwy, Islamorada image
75071 Overseas Hwy, Islamorada $3,199,000

Beautifully renovated oceanfront home in Islamorada offering 100 feet of direct ocean frontage, a sandy beach, breathtaking open water views, and mature tropical landscap...

  • 3 Beds
  • 2 Baths
  • 619869 MLS
143 N Hammock Rd, Islamorada image
143 N Hammock Rd, Islamorada $1,199,000

Experience all that Islamorada has to offer from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms...

  • 3 Beds
  • 3 Baths
  • 619848 MLS
88835 & 88845 Old Hwy, Tavernier image
88835 & 88845 Old Hwy, Tavernier $40,000,000

A rare dual-offering on coveted Millionaire's Row in Tavernier, this extraordinary oceanfront compound spans over multiple acres across two parcels-delivering an unmatche...

  • 8 Beds
  • 11 Baths
  • 619826 MLS
88845 Old Hwy, Tavernier image
88845 Old Hwy, Tavernier $27,000,000

Set on over 2 acres along prestigious Millionaire's Row in Tavernier, this newly constructed oceanfront estate represents a rare convergence of scale, design, and functio...

  • 5 Beds
  • 8 Baths
  • 619825 MLS
88835 Old Hwy, Tavernier image
88835 Old Hwy, Tavernier $15,000,000

An exceptional opportunity on coveted Millionaire's Row in Tavernier, 88835 Old Highway offers over 3 acres of oceanfront property paired with a rare additional acre feat...

  • 3 Beds
  • 3 Baths
  • 619824 MLS
148 Iroquois St, Tavernier image
148 Iroquois St, Tavernier $999,000 ▼

Spacious 4 bed, 3 bath home in the desirable Indian Mound neighborhood on Plantation Key. Sitting on two lots totaling about 11,000 sq ft, there's plenty of privacy and e...

  • 4 Beds
  • 3 Baths
  • 619796 MLS
81801 Overseas Highway Unit 637, Islamorada image
81801 Overseas Highway Unit 637, Islamorada $715,000 ▼

Welcome to your island King suite overlooking the beautiful lagoon at the historic Cheeca Lodge & Spa. Income producing property allowing 28 fabulous owner days! Cheeca h...

  • 1 Beds
  • 1 Baths
  • 619786 MLS
75840 Overseas Hwy, Islamorada image
75840 Overseas Hwy, Islamorada $12,950,000 ▼

LUXURY BEACHFRONT ESTATE HOME! Come embrace this brand-new magnificent property where you will encounter a relaxing ambiance gracefully set on over 2 private acres of pri...

  • 7 Beds
  • 7 Baths
  • 619776 MLS
44 W Plaza Del Lago, Islamorada image
44 W Plaza Del Lago, Islamorada $4,750,000

Double Lot! Unparalleled Waterfront Command in Port Antigua. Boasting one of the largest water frontages in Islamorada's exclusive Port Antigua, this striking 3 story ...

  • 4 Beds
  • 5 Baths
  • 619714 MLS
80450 Overseas Highway Unit 204, Islamorada image
80450 Overseas Highway Unit 204, Islamorada $550,000 ▼

Welcome to Sand Pebbles -- Islamorada's Hidden Gem. Located in the heart of the Village of Islamorada, this spacious 2-bedroom, 2-bathroom condo at the boutique community...

  • 2 Beds
  • 2 Baths
  • 619711 MLS
1101 Mastic St, Islamorada image
1101 Mastic St, Islamorada $6,999,000 ▼

Spectacular Bayfront Estate with Guesthouse in the Heart of Islamorada. & 7 Day Rental Potential, Seller Financing Available. Experience luxury coastal living at its f...

  • 8 Beds
  • 6 Baths
  • 619673 MLS
81801 Overseas Hwy Unit # 729, Islamorada image
81801 Overseas Hwy Unit # 729, Islamorada $699,000

Welcome to the iconic Cheeca Lodge & Spa Resort--a rare opportunity to own a premier, income-producing property in the heart of Islamorada. This beautifully appointed one...

  • 1 Beds
  • 1 Baths
  • 619668 MLS
75710 Overseas Highway Unit 1, Islamorada image
75710 Overseas Highway Unit 1, Islamorada $749,999 ▼

Fully furnished turn key townhome in Islamorada at Las Maravillas is available, one of only 10 private residences on the bayside on Lower Matecumbe in the Village. Docka...

  • 2 Beds
  • 2 Baths
  • 619594 MLS
88747 Old Hwy, Islamorada image
88747 Old Hwy, Islamorada $8,000,000

Discover your dream retreat in this beautiful oceanfront home, set on 1.5 acres of prime beachfront property with 150 feet of pristine white sandy beach, this is the ult...

  • 3 Beds
  • 3 Baths
  • 619592 MLS
33 Pen Ky, Islamorada image
33 Pen Ky, Islamorada $2,195,000

Welcome to your legacy retreat in Islamorada's premier gated waterfront community. A rare blend of privacy, prestige, and resort-style living awaits in this Key West-ins...

  • 3 Beds
  • 4 Baths
  • 619577 MLS
169 Venetian Way, Islamorada image
169 Venetian Way, Islamorada $1,550,000 ▼

Experience Coastal Luxury and privacy with this exceptional 5 bedroom, 3 bath home on two lots!! Over 2900 sq. ft. of thoughtfully designed living space. Constructed of...

  • 5 Beds
  • 3 Baths
  • 619545 MLS
88181 Old Hwy Unit B3, Islamorada image
88181 Old Hwy Unit B3, Islamorada $875,000 ▼

Islamorada luxury condo and boat slip for boats to 44' - the perfect combination for serious boaters! Located within a 14-acre, resort-style ocean front community of just...

  • 2 Beds
  • 2 Baths
  • 619533 MLS
106 Gardenia Ave, Tavernier image
106 Gardenia Ave, Tavernier $1,095,000

Live the Florida Keys Lifestyle in Your Dream Home Experience the perfect blend of elegance, functionality, and laid-back tropical living in this beautifully designed ...

  • 5 Beds
  • 3 Baths
  • 619499 MLS
154 Sebring Dr, Tavernier image
154 Sebring Dr, Tavernier $745,000 ▼

'Blue Haven' is a beautifully renovated elevated 2-story residence in the heart of Islamorada, offering the ideal blend of modern upgrades and relaxed Florida Keys living...

  • 3 Beds
  • 3 Baths
  • 619493 MLS
200 Wrenn St Unit 606, Tavernier image
200 Wrenn St Unit 606, Tavernier $700,000 ▼

TOP FLOOR oceanfront living awaits in this beautifully updated 2-bedroom, 2-bath condo located in desirable Sea Gulls development in Plantation Key. Enjoy breathtaking At...

  • 2 Beds
  • 2 Baths
  • 619480 MLS
179 Hibiscus St, Tavernier image
179 Hibiscus St, Tavernier $840,000 ▼

Welcome to your Keys get-a-away! Snuggled in the heart of Plantation Key colony, right at the entrance of the village of Islamorada: your island dreams, weekend oasis, or...

  • 2 Beds
  • 2 Baths
  • 619413 MLS
141 Canal St, Islamorada image
141 Canal St, Islamorada $3,499,000 ▼

Stunning Plantation Key canal front pool home! This exceptional all-concrete residence boasts a rare layout with five bedrooms, five full baths, and one-half bathroom, pe...

  • 5 Beds
  • 6 Baths
  • 619367 MLS
81801 Overseas Highway Unit 727, Islamorada image
81801 Overseas Highway Unit 727, Islamorada $585,000

Attention Investors! Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. This spacious Two Queen b...

  • 1 Beds
  • 1 Baths
  • 619365 MLS
87200 Overseas Hwy Unit S3, Islamorada image
87200 Overseas Hwy Unit S3, Islamorada $635,000 ▼

Welcome to effortless coastal living in the desirable Executive Bay Club community--where comfort, style, and resort-style amenities come together in a relaxed Keys setti...

  • 3 Beds
  • 3 Baths
  • 619364 MLS
118 Cortez Dr Unit B2, Islamorada image
118 Cortez Dr Unit B2, Islamorada $649,000 ▼

This island resort style unit offers stations for dockage up to 25-foot boats, trailer storage and boat ramp. There is a pool for the development, pickle ball and tenn...

  • 2 Beds
  • 2 Baths
  • 619328 MLS
200 Wrenn St Unit APT 510, Tavernier image
200 Wrenn St Unit APT 510, Tavernier $625,000 ▼

Elevated direct oceanfront living from a 5th-floor 2 bedroom 2 bath residence in Sea Gulls on Plantation Key in Islamorada. This all concrete building offers peace of min...

  • 2 Beds
  • 2 Baths
  • 619284 MLS

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