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$255,000
1 Beds ⋅ 1 Baths ⋅ 616012 MLS
Charming Studio in Desirable Summer Sea - Islamorada, the Fishing Capital of the World! Enjoy the best of the Florida Keys in this furnished studio located in the sought-after, gated Summer Sea community in Islamorada. This waterfront development offers an unbeatable combination of comfort, location, and amenities—perfect for weekend getaways, a rental investment, or full-time island living. Take in panoramic Florida Bay views and spectacular sunsets and easy access to the Atlantic Ocean just minutes away. Boaters will appreciate the dock privileges, new composite dock, boat ramp, fish cleaning station, and storage for kayaks and paddleboards. Other outstanding amenities include a large heated swimming pool, adult and kids game rooms, a party room, newly equipped gym, laundry rooms and two new elevators. Whether you're casting off for world-class fishing or simply soaking up the Keys lifestyle, Summer Sea offers the perfect blend of relaxation and recreation in the heart of Islamorada.

88500 Overseas Highway Unit 233, Islamorada
$1,650,000
3 Beds ⋅ 3 Baths ⋅ 616219 MLS
Welcome to your dream home in the heart of the Florida Keys! This exquisite two-story waterfront residence in prestigious Venetian Shores offers the perfect blend of luxury, coastal charm, and unparalleled boating access to the Atlantic Ocean and Florida Bay with a 40 ft. boat slip steps away. Offered fully furnished, with remodeled bathrooms, new floors, a brand-new metal roof (2025), and a stunning new exterior, this home delivers beauty, value, and irresistible curb appeal. Just bring your toothbrush—or your renters! A brilliant investment in the Florida Keys. With 3 bedrooms, 3 full baths, and 2 car garages, this home is move-in ready to start living the Keys lifestyle. As you step inside, you will be captivated by the bright, airy spaces adorned with designer furnishings. The open-concept living area seamlessly flows into a gourmet kitchen with all KitchenAid® stainless appliances, perfect for entertaining. Porcelain tiles add modern warmth, while expansive windows frame stunning canal, peekaboo bay, and marina views. Plus, open water vistas of Snake Creek invite natural light, the beauty of the outdoors, and magnificent sunsets in. Downstairs, enjoy a separate apartment for guests, a private office, in-law suite, or teen sanctuary. This home is also equipped with a tankless water heater, security cameras, and whole-home water purification. Step outside to your private paradise! With near-instant ocean and bay access, your 40 ft. boat slip can accommodate the perfect vessel for exploring the nearby reefs, fishing, or cruising the gorgeous waters of Islamorada, the Sport Fishing Capital of the World. Located in one of the Keys' most sought-after neighborhoods, you'll be moments from world-class dining, shopping, vibrant local culture, and Founder's Park with its beach, sports fields, amphitheater, and pool complex. Whether you are seeking the serenity of a full-time residence, a vacation getaway, or an income generator, this home is your ticket to paradise.

106 San Juan Dr Unit & Boat Slip, Islamorada
$850,000
3 Beds ⋅ 3 Baths ⋅ 616172 MLS
Islamorada Home with Homeowner's Park & 72-Hour Dockage. Enjoy Keys living in this 3 bedroom, 2.5 bathroom home featuring vaulted tongue-and-groove ceilings, a metal roof (2007), and plenty of space inside and out. The primary suite occupies the entire top floor, complete with vaulted ceilings, walk-in closet, and spacious bath. The main living level offers two guest bedrooms with a shared bath, plus a home office, large laundry room, and open kitchen/dining area with abundant cabinets and counter space. Step outside to a backyard built for entertaining—featuring a bar area, above-ground pool, koi pond, grilling space, shed, and a large garage. The homeowner's park is just minutes away, offering a boat ramp and 72-hour dockage with immediate access to Tavernier Creek—making both the ocean and bay just seconds away. Conveniently close to schools, shopping, grocery stores, and restaurants.

216 Pearl Ave, Islamorada
$1,300,000
2 Beds ⋅ 2 Baths ⋅ 617880 MLS
Desirable White Marlin Beach offers one of the best bayside beaches and swim areas in the Keys - exclusive to residents at the homeowner's park. This canal-front home is perfectly positioned on a corner lot with 100' of dockage, two boat lifts, and a private ramp ideal for launching kayaks and paddle boards. The home features 2 bedrooms, 2 baths, plus a loft, and has been thoughtfully maintained with impact windows and doors, a metal roof, central AC (2025), and a water heater (2024). Enjoy quick access to the Florida Bay, with the Channel 5 Bridge providing easy passage to the ocean side with 65' clearance. Additional highlights include an outdoor shower and the private homeowner's park with tikis and grills. A well-kept property in a truly special waterfront community.

213 Nautilus Dr, Islamorada
$1,100,000
5 Beds ⋅ 4 Baths ⋅ 616259 MLS
Welcome to 131 Indian Mound Trail - A Tranquil Coastal Retreat in the Heart of Plantation Key and the Village of Islamorada. Situated in the highly sought-after Indian Mound neighborhood, this beautiful two-story concrete home offers the ideal blend of comfort, space, and coastal charm — perfect for families or investors looking to own a slice of paradise in the Upper Keys. Step inside to a bright and airy open-concept living area, designed for relaxed island living and entertaining. The upper level features three spacious bedrooms and two bathrooms, enhanced by vaulted ceilings, wood shiplap accent walls, plantation shutters and elegant woodgrain tile flooring throughout. The stylish kitchen is appointed with quartz countertops and stainless steel appliances. The ground level features separate living quarters with two additional bedrooms and two bathrooms, offering a flexible layout ideal for guests, extended family, or rental income. Built for durability and peace of mind, the home includes a solid concrete roof and impact-rated windows and doors. Just steps away, enjoy access to the fantastic bayfront homeowners park featuring a private dock, boat ramp, and some of the best sunsets in town! The location is equally convenient, with Plantation Key Elementary and Coral Shores High School just down the street. Don't miss this opportunity to own a move-in-ready home in one of Islamorada's most desirable neighborhoods.

131 Indian Mound Trl, Islamorada
$10,600,000
3 Beds ⋅ 3 Baths ⋅ 615248 MLS
Pure magic. Every step on this property is like a step back in time. Once you pass through the gated coral rock entrance you are instantly transported back to the Old Keys as you wind down the driveway through the shady tropical hammock and meander your way to the settler's beach home circa 1934. The charming 3/3 fishing cabin was meticulously updated to add modern comforts but still maintain its relaxing Old Florida appeal. The kitchen, living room and primary bedroom all enjoy open ocean views and all three bedrooms are ensuite. Just sitting on the shady back porch, enjoying the hush of the palms, you could mistake this breathtaking oceanfront for a postcard of yesterday's Florida Keys a century ago. This one-of-a-kind oceanfront estate property includes 4.3 acres of upland plus another 2.65 acres of baybottom and approximately 400 feet along the water! There is also a deep water dock (going into permitting for repair) and a unique collection of rare mature palms. The Native Residential (NR) Zoning allows for many different options for future development and also allows for weekly rentals. This is one of the rare, truly private large parcels on Plantation Key in Islamorada. Don't miss the opportunity to make this unspoiled piece of the past part of your future in the Keys! Call today for more details and to request a private showing.

89251 Old Hwy, Islamorada
$1,700,000
4 Beds ⋅ 4 Baths ⋅ 614741 MLS
Open Bay Views, Boat Dockage, Pool 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 4/4 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 nearly 3,000 sf of spacious living space perfect for a large or extended family. The Madeira Bay gated community is a hidden treasure of only 8 homes tucked in behind one of Islamorada's most beloved local restaurants in a peaceful private neighborhood. In addition to the community dock there is also a community pool and a gradual shoreline for launching a boat, paddle board or kayak or for wading directly into the bay with your rafts and floats! Inside, the stunning great room opens to the bay view porch on the main living level where there are also three bedrooms and two full baths in a split plan. There is also an open loft bedroom with full bath upstairs just off the great room featuring beautiful bay views. The fully permitted downstairs is connected by internal spiral stairs and adds a separate ground level entrance plus a spacious second living room, wet bar area for entertaining, plus a private guest bedroom with a full bath and outdoor porch. There is also an attached garage for protected parking and/or storage. The downtown location offers immediate access to shopping, fine dining, bars, galleries, art studios and all the regular local art festivals, full moon parties and events. Madeira Bay homes rarely come on the market and this one is a must see!

82762 Overseas Hwy Unit 3, Islamorada