Plantation Key, FL Homes

/49
$1,195,000
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
192 E Ridge Rd, Islamorada, FL 33036

Discover your dream getaway in this charming island retreat, perfectly situated on one of Islamorada's most coveted streets. Surrounded by tropical lush vegetation, this all-concrete property offers the ideal blend of privacy and access to paradise, just steps away from Founders Park, featuring a beach, tennis and pickleball courts, and an Olympic-sized pool.This two-bedroom, one-bathroom home

Pierre Bellion

Ocean Sotheby's International Realty

(786) 840-9826

192 E Ridge Rd, Islamorada, FL 33036
/11
$1,950 per month
- 2 Beds
- 2.5 Baths
- 1,160 Sq Ft
- Townhouse for Rent
84771 Overseas Hwy, Islamorada, FL 33036

2-bedroom, 2.5-bathroom affordable rental unitavailable for annual lease.

Cliff Glansen FlatFee.com

84771 Overseas Hwy, Islamorada, FL 33036
/12
$650,000 Sold May 01, 2025
- 1,844 Sq Ft
- $352/SF
- 74 Days On Market
- 3 Beds
- 2 Baths
Unlisted Address

Rare opportunity to build on this permitted lot in the highly desirable Bay Hammock community. ***ASSIGNED BOAT SLIP INCLUDED WITH LOT.*** This exclusive gated neighborhood is located on Upper Matecumbe Key conveniently located close to everything downtown Islamorada has to offer. Totaling just over 12,000 sq ft this lot has ample space for a home of your dreams.Protected Bayfront marina with

Jessica Pinder

Unlisted Address

/2
Est $2,923,310 Not Listed For Sale
- 4 Beds
- 5 Baths
- 2,539 Sq Ft
80639 Old Hwy Unit 203, Islamorada, FL 33036

80639 Old Hwy Unit 203, Islamorada, FL 33036

/46
$665,000
- 2 Beds
- 2 Baths
- 1,343 Sq Ft
87200 Overseas Hwy Unit 9, Islamorada, FL 33036

Welcome to your new home in the heart of Islamorada! This desirable 2-bedroom, 2-bathroom townhouse offers an exceptional blend of comfort and luxury, perfect for those seeking a serene yet vibrant coastal lifestyle.Step inside to discover a spacious living area bathed in natural light, designed with an open-concept layout that flows seamlessly into the outdoor space. The modern kitchen is a

Pierre Bellion

Ocean Sotheby's International Realty

(786) 692-8536

87200 Overseas Hwy Unit 9, Islamorada, FL 33036
/19
$5,250 per month
- 5 Beds
- 3 Baths
- 2,236 Sq Ft
- House for Rent
176 E Carroll St, Islamorada, FL 33036

LONG TERM RENTAL SINGLE FAMILY HOME - UNFURNISHED. Located in the HEART of Islamorada. New CBS build in 2023 with 3BR/2BA on upper level and 2BR/1BA on ground level. Ground level has separate entrance - ideal for in-law suite, guests or home office/work area. Located off the main highway on quiet street and close to restaurants and shopping. Approximately 600' to neighborhood beach. No

Andrea (Andi) Saylor Realty One Group Engage the Keys

176 E Carroll St, Islamorada, FL 33036
/44
$2,700,000 Sold May 01, 2025
- 2,880 Sq Ft
- $938/SF
- 328 Days On Market
- 4 Beds
- 3 Baths
- Built 2024
85331 Overseas Hwy, Islamorada, FL 33036

WEEKLY RENTALS to be allowed with new Zoning Change. Potential SELLER FINANCING AVAILABLE!!! Brand new oceanfront Concrete Home. Coastal-inspired masterpiece with wood plank porcelain tile flooring.Panoramic ocean views from the spacious living areas, including the kitchen, dining room, and master suite. Elevator to all 3 floors. The gourmet kitchen with quartz countertops, high-end GE

Jocelyn Tiedemann Ocean Sotheby's International Realty

85331 Overseas Hwy, Islamorada, FL 33036

/53
Est $2,132,898 Not Listed For Sale
- 4 Beds
- 3.5 Baths
- 1,829 Sq Ft
81906 Overseas Hwy, Islamorada, FL 33036

81906 Overseas Hwy, Islamorada, FL 33036

/57
$2,695,000
- 4 Beds
- 4 Baths
- 2,728 Sq Ft
82762 Overseas Hwy Unit 3, Islamorada, FL 33036

Open Bay Views, Boat Dockage and more... all in the Heart of Downtown Islamorada! Have you been dreaming of living downtown, but can't find a home with dedicated boat dockage and open water views? If so, this custom home in Madeira Bay is your dream come true! Enjoy open water views from the porch, living room, kitchen, loft and bedroom plus soaring ceilings and lots of living space. The Madeira

Brett Newman Coldwell Banker Schmitt Islamorada

82762 Overseas Hwy Unit 3, Islamorada, FL 33036
/20
$4,000 per month
- 2 Beds
- 2 Baths
- Townhouse for Rent
87200 Overseas Hwy Unit 1, Islamorada, FL 33036

Prestigious Executive Bay Club corner townhouse in Islamorada. Offering 2BD/2Bth and loft. Spacious, updated & completely furnished. Beach front private community with 24 manned gate entrance, private beach to enjoy beautiful sunsets, pool, tennis courts, club house, first come first serve dock. Next door to Founder's Park offering many activities including the famous Nautical flee market. Assoc

Isabel Ruiz Coldwell Banker Realty

87200 Overseas Hwy Unit 1, Islamorada, FL 33036
/63
$1,200,000 Sold Apr 25, 2025
- 1,680 Sq Ft
- $714/SF
- 46 Days On Market
- 3 Beds
- 3 Baths
- Built 2023
84745 Old Hwy Unit 5, Islamorada, FL 33036

Peaceful Palms - Luxury Oceanfront Living in the Florida KeysWelcome to Peaceful Palms, a newly developed gated coastal community offering 15 exclusive high-end townhomes in the heart of the Florida Keys. This oceanfront retreat boasts breathtaking views of the renowned Sandbar and Alligator Reef Lighthouse, providing the perfect blend of luxury, relaxation, and investment potential.Each

Ernesto Portuondo American Caribbean Real Estate, Christie's International Real Estate

84745 Old Hwy Unit 5, Islamorada, FL 33036

/42
Est $2,754,589 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 3,139 Sq Ft
80639 Old Hwy Unit 403, Islamorada, FL 33036

80639 Old Hwy Unit 403, Islamorada, FL 33036

/53
$3,275,000
- 4 Beds
- 3 Baths
- 2,782 Sq Ft
109 South Dr, Islamorada, FL 33036

Located in a private, gated community in the heart of Islamorada, 109 South Drive is a rare waterfront retreat that perfectly blends luxury, comfort, and the ultimate Florida Keys lifestyle. The main home features 4 spacious bedrooms and 3.5 beautifully designed bathrooms upstairs, while a separate 1-bedroom, 1-bath apartment downstairs offers privacy for guests or rental potential. Enjoy a

Derek Rodberg Coastal Realty of the Florida Keys

109 South Dr, Islamorada, FL 33036
/67
$12,000 per month
- 4 Beds
- 4.5 Baths
- 2,800 Sq Ft
- House for Rent
105 Carroll St Unit 1, Islamorada, FL 33036

Remarkable New Construction luxury home in the heart of Islamorada. Nestled between 2 luxurious resorts (Cheeca Lodge and Caribbean) walkable area very quiet and serene away from main road. Minimum rental monthly. Available August thru December. Fully furnished and equipped. Private beach + pier. Home has private salt water heated pool, outdoor kitchen fully equipped with grill, outdoor sink,

Marisa Hawayek DK International Rlty Inc.

105 Carroll St Unit 1, Islamorada, FL 33036
/15
$675,000 Sold Apr 23, 2025
- 550 Sq Ft
- $1227/SF
- 8 Days On Market
- 1 Bed
- 1 Bath
- Built 1988
81801 Overseas Hwy Unit 612, Islamorada, FL 33036

Cheeca Lodge Resort and Spa--the very name conjures up images of swaying palms, salt-kissed air, a rich history, and the promise of an idyllic escape. Where the Sun Kisses the Sea and Dreams Come to Life.Historic Charm, Modern Luxury: Cheeca Lodge--a time capsule where history whispers. Turnkey suites, nightly rentals, and savvy investment. Feast Fit for Poseidon: Five-star dining, tiki bars,

Eric Rizzo Ocean Sotheby's International Realty

81801 Overseas Hwy Unit 612, Islamorada, FL 33036

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
81801 Overseas Hwy Unit 742 & 743, Islamorada, FL 33036

81801 Overseas Hwy Unit 742 & 743, Islamorada, FL 33036

/92
$5,990,000
- 4 Beds
- 4.5 Baths
- 2,574 Sq Ft
82779 Old Hwy Unit 3, Islamorada, FL 33036

Welcome to The Islands of Islamorada, a private gated enclave of coastal luxury. Our exquisite waterfront residences feature four bedrooms and four and one-half bathrooms, designed for your comfort. Each three-floor villa offers 3,137 square feet of interior space and 930 square feet of outdoor living, showcasing contemporary island architecture. Three king-sized bedrooms have en-suite bathrooms,

Richard Lemon Serhant Florida LLC - Delray Beach Office

82779 Old Hwy Unit 3, Islamorada, FL 33036
/20
$2,900 per month
- 2 Beds
- 2 Baths
- 981 Sq Ft
- Property for Rent
87465 Old Hwy Unit 218, Islamorada, FL 33036

Viva la experiencia unica de los Cayos en este espectacular apartamento amueblado en Plantation by The Sea!Ubicado en la prestigiosa y conveniente Islamorada, este exclusivo condominio estilo casa adosada de dos pisos es el refugio perfecto para aquellos que buscan comodidad y una autentica vida costera. Totalmente amueblado y equipado, solo traiga sus maletas y preparese para disfrutar.Este

Florentina Antigua EXP Realty LLC

87465 Old Hwy Unit 218, Islamorada, FL 33036
/56
$629,000 Sold Apr 17, 2025
- 1,359 Sq Ft
- $463/SF
- 150 Days On Market
- 2 Beds
- 2 Baths
- Built 1980
87200 Overseas Hwy Unit P8, Islamorada, FL 33036

Discover the ultimate in Florida Keys living with this fully renovated 2-bed, 2-bath villa in Islamorada's exclusive Executive Bay Club! This bright unit offers a versatile loft space, granite countertops, stainless steel appliances, and stylish zebra shades throughout. The spacious master suite includes built-in closets, while the villa's unbeatable location is just steps from the pool, private

Steven Koleno Beycome of Florida, LLC

87200 Overseas Hwy Unit P8, Islamorada, FL 33036

/38
Est $1,729,140 Not Listed For Sale
- 3 Beds
- 3.5 Baths
- 1,680 Sq Ft
84 Johnston Ave Unit 6, Islamorada, FL 33036

84 Johnston Ave Unit 6, Islamorada, FL 33036

/56
$1,195,000
- 2 Beds
- 2 Baths
- 1,536 Sq Ft
87851 Old Hwy Unit M32, Islamorada, FL 33036

THE place to live in the Upper Florida Keys! 3rd floor 2 bedroom, 2 bath condo with sensational ocean views. Waterfront clubhouse with exercise room and ample space for private parties. 50 slip marina with dockage available for rent. Prior to a dip in the pool work off a little energy on the tennis courts or a casual set of pickleball. Lounge under the tikis on the 12 tropically landscaped

Eric Johnson Century 21 Circle - Islamorada

87851 Old Hwy Unit M32, Islamorada, FL 33036
/4
$1,800 per month
- 1 Bed
- 1 Bath
- 411 Sq Ft
- Property for Rent
84961 Old Hwy Unit 36, Islamorada, FL 33036

Don't miss this opportunity to rent this cozy single wide trailer featuring 1 bedroom and 1 bath, ideal for the minimalist lifestyle. Enjoy your mornings or evenings on spacious, private, screened porch, perfect for relaxation and entertaining.This condo association property features a fantastic jetty and tiki hut that overlooks serene water views, creating a tranquil outdoor oasis. Located

Lizette Miller Coldwell Banker Schmitt Islamorada

84961 Old Hwy Unit 36, Islamorada, FL 33036
/51
$3,500,000 Sold Apr 15, 2025
- 2,304 Sq Ft
- $1519/SF
- 405 Days On Market
- 4 Beds
- 4 Baths
- Built 1983
139 Bayview Isle Dr, Islamorada, FL 33036

Timeless Waterfront Charm in Venetian Shores, Islamorada - Indulge in classic charm with this meticulously positioned waterfront residence in sought-after Venetian Shores. A dream come true for those who appreciate spectacular sunsets and unparalleled boating opportunities in the Florida Keys. Step into the gracious embrace of a bygone era in this residence poised directly on Snake Creek, the

Brett Newman Coldwell Banker Schmitt Islamorada

139 Bayview Isle Dr, Islamorada, FL 33036

/2
Est $1,372,037 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,813 Sq Ft
87851 Old Hwy Unit P45 & 50' boat slip, Islamorada, FL 33036

87851 Old Hwy Unit P45 & 50' boat slip, Islamorada, FL 33036

/79
$5,299,000
- 6 Beds
- 5 Baths
- 4,964 Sq Ft
153 Stromboli Dr, Islamorada, FL 33036

Exquisite Tri-Level Waterfront Estate in Islamorada!Step into luxury with this remarkable home in the prestigious Venetian Shores, designed for the most discerning buyer. Offering six bedrooms, five bathrooms, and a spacious 5000sqft of magnificently designed living space, this residence boasts an open-concept floor plan with soaring ceilings, a fireplace and a grand living area.Enjoy seamless

Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

153 Stromboli Dr, Islamorada, FL 33036
/12
$13,500 per month
- 3 Beds
- 2.5 Baths
- 1,350 Sq Ft
- House for Rent
Unlisted Address

This 2 story home sits on the Gulf of Mexico with expansive bay views and unparalleled sea life that will entertain you right from the backyard. It is central to numerous delicious local restaurants and is a boater's dream with many sand bars and world renowned offshore and back country fishing at your fingertips. It's on a deep water canal with open water access. Relax in the newly remodeled

Dana Pollitt Esquire R E Brokerage LLC

Unlisted Address
/33
$420,000 Sold Apr 07, 2025
- 1,036 Sq Ft
- $405/SF
- 137 Days On Market
- 2 Beds
- 2 Baths
- Built 1977
87455 Old Hwy Unit 116, Islamorada, FL 33036

Your vacation starts now! Welcome to Plantation By The Sea. This charming TURN KEY 2 bedroom and 2 bathroom end unit offers a spacious floor plan that seamlessly connects the kitchen to the dining and living areas. It has 2 porches 1 off of the living room another off of the master bedroom. While cooking you can open up the doors and enjoy the ocean breeze and 'peak a boo' views of the Ocean.

Jessica Pinder

87455 Old Hwy Unit 116, Islamorada, FL 33036

/33
Est $711,358 Not Listed For Sale
- 1 Bed
- 1 Bath
- 550 Sq Ft
81801 Overseas Hwy Unit 722, Islamorada, FL 33036

81801 Overseas Hwy Unit 722, Islamorada, FL 33036

/34
$1,200,000
- 3 Beds
- 2 Baths
- 1,536 Sq Ft
87851 Old Hwy Unit K33, Islamorada, FL 33036

Oceanfront Paradise in the Florida Keys - 2BR/2BA Condo offering Luxury Resort-Style Living.Escape to your own slice of paradise with this stunning 2-bedroom, 2-bathroom oceanfront cottage like condo, perfectly positioned on the Atlantic Ocean in the heart of the Florida Keys. Wake up to breathtaking sunrises and unwind with the sound of the swaying palm trees as you enjoy ocean views from your

Krissy Carnahan Realty ONE Group Destination (ISL)

87851 Old Hwy Unit K33, Islamorada, FL 33036
/44
$10,000 per month
- 4 Beds
- 3 Baths
- 1,470 Sq Ft
- House for Rent
109 Palo de Oro Dr, Islamorada, FL 33036

Located 90 minutes from Miami and 20 minutes to the world-famous Tiki Bar sandbar (dock to anchor) one of the best in the Keys. Enjoy easy and quick access to the bay or ocean via Snake Creek, excellent fishing/water activities, dining, and amazing sunsets. There is a marina located nearby that sells fuel, bait, ice and offers boat rentals. This is a 2 story property, 4 bedrooms and 2 bathrooms

Edelso Riveron Related Services LLC

109 Palo de Oro Dr, Islamorada, FL 33036
/8
$260,000 Sold Apr 04, 2025
- 93 Days On Market
- Built 2014
96 Madeira Rd Unit 4, Islamorada, FL 33036

Highly sought after 50 foot live aboard boat slip available at the Islamorada Yacht Basin adjacent to the Lorelei Restaurant & Cabana Bar. Dimensions are 50' long by 20' wide. Located on the West side of the marina. Amenities include showers, restrooms, laundry, pump out. Excellent location in downtown Islamorada with walking distance to many shops. Call for details.

The Jude Lindback Te Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

96 Madeira Rd Unit 4, Islamorada, FL 33036

/2
Est $3,384,000 Not Listed For Sale
- 3 Beds
- 3 Baths
- 1,680 Sq Ft
84745 Old Hwy Unit 3, Islamorada, FL 33036

84745 Old Hwy Unit 3, Islamorada, FL 33036

/61
$2,950,000
- 4 Beds
- 3 Baths
- 2,072 Sq Ft
81250 Overseas Hwy Unit 5, Islamorada, FL 33036

Only sophistication and class represented in Islamorada's most exclusive development, Tarpon Flats. This rare offering has underwent a full high-end renovation to satisfy the most distinguished buyer. The elegant paver driveway leads up to pristine grounds showing off it's manicured landscaping. One of only 12 luxury bayfront homes on a sprawling four-acre parcel. The property exudes a unique

Drew Moret Palm House Real Estate

81250 Overseas Hwy Unit 5, Islamorada, FL 33036
/30
$20,000 per month
- 5 Beds
- 5 Baths
- Property for Rent
128 Leoni Dr, Islamorada, FL 33036

SPECTACULAR VENETIAN SHORES HOME! 70' concrete dock on deep water canal which opens directly to Snake Creek for quick and easy access to bay or ocean; Furnished; 5 bedrooms/4.5 baths; private master retreat with gorgeous bath on third level; marble floors throughout; elevator; FABULOUS chef's kitchen with Wolf gas range and huge island; large terraces and fantastic entertaining spaces; Sonos

Emily Romberg Real Estate Sales Force

128 Leoni Dr, Islamorada, FL 33036
/50
$3,900,000 Sold Apr 02, 2025
- 2,358 Sq Ft
- $1654/SF
- 36 Days On Market
- 5 Beds
- 4 Baths
- Built 1960
80459 Old Hwy, Islamorada, FL 33036

Discover Coconut Cottage, Your Tropical Paradise in Islamorada! Coconut Cottage beckons you to the quintessence tropical living in Islamorada. This oceanfront haven boasts a 90ft. Sandy Beach, a boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both relaxation and adventure. The main residence, featuring 4 bedrooms and three bathrooms, exudes vintage Florida coastal

Jan Keller Coldwell Banker Schmitt Islamorada

80459 Old Hwy, Islamorada, FL 33036

/4
Not Listed For Sale
0 Palo de Oro Dr Unit 606772, Islamorada, FL 33036

0 Palo de Oro Dr Unit 606772, Islamorada, FL 33036

/59
$2,800,000
- 3 Beds
- 3.5 Baths
- 4,537 Sq Ft
33 Pen Key Dr, Upper Matecumbe Key Islamorada, FL 33036

Discover Your Private Tropical Oasis in Islamorada.Welcome to your dream retreat in the heart of the Florida Keys in the sport fishing capital of the worlda'a stunning Key West-style home nestled amidst lush greenery in an exclusive gated bayfront private club community. This residence is more than just a home; it's a lifestyle defined by serenity, elegance, and the natural beauty of

Eric Rizzo Ocean Sotheby's International Realty

33 Pen Key Dr, Upper Matecumbe Key Islamorada, FL 33036
/36
$4,250 per month
- 2 Beds
- 2 Baths
- 1,176 Sq Ft
- House for Rent
101 Gumbo Limbo Rd, Islamorada, FL 33036

Looking for a nice desirable rental? for a year or shorter, it is fully furnished and ready to move in. Come see it today.

Jose Vigo RE/MAX All Keys Real Estate

101 Gumbo Limbo Rd, Islamorada, FL 33036
/52
$1,100,000 Sold Mar 24, 2025
- 1,518 Sq Ft
- $725/SF
- 257 Days On Market
- 3 Beds
- 2 Baths
- Built 2019
125 N Hammock Rd, Islamorada, FL 33036

This beautiful 4-year-old ground-level home features 3 bedrooms and 2 bathrooms. The kitchen boasts stunning all-wood cabinets, granite countertops, and stainless steel appliances. Marble tile floors extend throughout the house, creating a luxurious and cohesive feel.The home includes a large screened porch off the back two bedrooms, perfect for enjoying the surrounding tropical tree canopy. The

James Mooney Jr. Ocean Sotheby's International Realty

125 N Hammock Rd, Islamorada, FL 33036

/2
Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,536 Sq Ft
87851 Old Hwy Unit K5 & boat slip 42, Islamorada, FL 33036

87851 Old Hwy Unit K5 & boat slip 42, Islamorada, FL 33036

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