Upper Matecumbe Key, FL Homes for Sale

Nestled in the heart of Islamorada, this ground-level residence captures the essence of timeless Old Florida charm with refined modern updates. Offering 3 bedrooms and 2 bathrooms with 1,300sf of living space, the home has been updated with impact windows and doors, metal roof, renovated kitchen and updated bathrooms, and a newer A/C and water heater.The outdoor spaces are equally inviting. A

Claire Johnson Coastal Realty of the Florida Keys

This breathtaking three-story beachfront estate offers the ultimate blend of resort-style living and refined comfort. Featuring six spacious bedrooms and five luxurious bathrooms, and three inviting living rooms, home is designed to accommodate both relaxation and entertainment with ease. Set in a serene cove with a pristine natural beach, the home showcases floor-to-ceiling windows that frame

Cheri Tindall Ocean Sotheby's International Realty

Discover an extraordinary opportunity to own 34,000 square feet of prime bayfront real estate in one of Islamorada's most coveted and private enclaves. Boasting 100+ feet of pristine bay frontage, this exceptional property captures open water views, serene sunsets, and the essence of the Florida Keys lifestyle. Tucked within the property is a charming ground level 1950s cottage offering one

Bonnie Oliver Ocean Sotheby's International Realty

Set within a private gated enclave, this top-floor, corner unit captures the essence of Islamorada living. Quietly elevated, effortlessly refined, and deeply connected to the surrounding seascape. Positioned to embrace sweeping Atlantic Ocean views and the iconic Alligator Reef Lighthouse, expansive walls of glass invite natural light and open water vistas into nearly every space, including each

TEAM Walters Gloria, Rachel and Michae Ocean Sotheby's International Realty

Experience unparalleled oceanfront living at the Chateau On The Ocean, a turnkey private estate set within an exclusive enclave in Islamorada. Here elevated coastal living reflects the sophistication of what has been referred to as the Hamptons of Miami. From the moment you arrive, a striking sense of privacy, scale, and intention is evident, with architecture and surroundings that feel truly

Pamela DiMartino Coldwell Banker Realty

BAYSIDE, DEEP WATER, BREATHTAKING GULF VIEWSWelcome to one of Islamorada's premier rare bayside estate properties - a remarkable parcel that stretches from Overseas Highway all the way to the Bay. The home bestows privacy, unobstructed Gulf Views, and a deep-water basin for calm dockage cable of accommodating substantial vessels with immediate access to world class sportfishing waters.The

Steven Koleno Beycome of Florida, LLC

Set in the very center of Islamorada's vibrant island community, this 2BD/2.5BA townhouse style condo in Sand Pebbles offers privacy, comfort, and convenience. The ground level features two spacious en-suite bedrooms, each with its own private porch. Upstairs, enjoy a bright open-concept living, dining, and kitchen area plus a convenient half bath. With 1,303 sq ft and multiple outdoor living

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

Experience all that Islamorada can provide from this stunning home that was constructed in 2020. This two-story residence offers 3 spacious bedrooms and 2 full bathrooms on the ground floor. The second floor has a large great room - ideal for a home office, second living room, playroom, or media space—adding extra versatility to the layout. Additionally, there is another full bathroom upstairs.

Brent Baris COMMERCIAL PROPERTY BROKERS

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-inspired residence, set within one of Islamorada's most exclusive gated bayfront communities. Surrounded by manicured tropical landscaping and timeless architectural charm, this home offers an elevated island lifestyle defined

Eric Rizzo Ocean Sotheby's International Realty

🌊 Spectacular Direct Ocean Views! ✨ Islamorada's Best‑Kept Secret!This beautifully appointed 2-bedroom, 2-bath residence offers breathtaking, unobstructed ocean views from your private waterfront balcony. Step outside and enjoy a refreshing swim in the oceanfront pool or take a dip directly in the crystal‑clear Atlantic. Photos Coming Soon.Perfectly situated near Bud &

Tracey Petrusha Venture Realty Group

Ground-level living in the heart of Islamorada! Situated on an oversized parcel, this beautifully completely remodeled 2-bedroom, 2-bath home offers comfort and an unbeatable location. The tastefully updated interior includes porcelain tile throughout the home including showers, quartz countertops and brand new LG appliances and offers an open living area and flows seamlessly to a large screened

Lisa Frins Berkshire Hathaway HomeServices Keys Real Estate - Islamorada

Downtown Islamorada gem located on a massive 11,000+ square-foot lot on a quiet street. Vaulted exposed wood beam ceilings give the home a spacious, open vibe. New roof installed in 2022, brand new appliances, and a brand new screen-in enclosure on the front porch ready to enjoy. The first floor offers covered parking and a handy storage room. Close to all the shops, restaurants, and fun that

AJ Vetter Palm House Real Estate

Exclusive Beacon Reef Unit 504 presents a rare opportunity in the heart of downtown Islamorada. This updated top-floor residence offers higher ceilings, enhanced views, and a larger porch--creating a true penthouse feel. The property is impeccably maintained and delivers a resort-style lifestyle set against beautifully landscaped, oceanfront grounds.Located just steps from world-class fishing,

Drew Moret Palm House Real Estate

Beacon Reef is calling your name! This beautifully designed 2-bedroom, 2-bath residence spans approximately 1,275 square feet of light-filled living space. Enjoy the charming balcony with a steady breeze and lovely ocean views from the primary and balcony. With a spacious primary suite complete with an en-suite bath and charming sitting area and an oversized guest suite offering flexibility and

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

Islamorada Bayfront Estate with Dockage & Open Bay Views... all in downtown Islamorada within walking distance of your favorite spots! Custom built in 2014, this concrete fortress is storm-resilient and also offers a host of sustainability features including a whole-house solar array. Situated on a peninsula with 250+ feet of crystal-clear open waterfront, the gated estate provides unparalleled

Brett Newman Coldwell Banker Schmitt Islamorada

Ideally located in the heart of Islamorada, this charming home is perfectly updated with a harmonious blend of old and new Keys characteristics and a light and airy layout and enclosed sun room that brings the lovely landscaping inside! A serene pool and oversized backyard with plenty of privacy provide book ends to lovely days of beat the heat splashes during the day and evenings of peace and

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

Newly Remodeled 3-Bed, 3-Bath Home in the Heart of IslamoradaThis beautifully remodeled 3-bedroom, 3-bath home is located on Upper Matecumbe in the heart of Islamorada, offering the perfect combination of luxury, comfort, and island style--all on one level. The open-concept floor plan features a spacious living area ideal for entertaining, a modern kitchen with stainless steel appliances and

James Mooney Jr. Ocean Sotheby's International Realty

THIS UNIT COMES WITH COVERED PARKING. Not all units have covered parking. Covered parking is equal to 2+ parking spaces. The additional parking is a plus because you have the option to keep your boat on a trailer with you at the property, and~or space for your golf cart, bikes, etc. Enjoy Islamorada fully with this extra space. The best of everything at Beacon Reef, centrally locacted close to

Danielle Cockerham Coastal Realty of the Florida Keys

Welcome to Casa Mar Azul, a one-of-a-kind oceanfront estate located along the iconic Old Highway in Islamorada -- a rare offering with 200 feet of oceanfront shoreline, a private jetty with dockage, and breathtaking panoramic views of the Atlantic Ocean. This elegant coastal retreat blends indoor-outdoor living with an open floor plan and soaring vaulted tongue-and-groove ceilings that bring

Alina Davis Coldwell Banker Schmitt Islamorada

Welcome to Your Florida Keys retreat or income-producing rental, with 7-day rentals approved! Maison Residences presents its final developer unit, #201, offering 4 bedrooms, 4.5 bathrooms and a spacious open layout designed for true oceanside living. Step off your private elevator into a grand room with soaring 10-foot ceilings and 9-foot stacked sliders that frame endless Ocean views. The open

Jennifer Gomez LPT Realty, LLC

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

AJ Vetter Palm House Real Estate

Island Life in the Heart of Islamorada, a ground-level, 3 bed, 2 bath home with all the charm and comfort you need to enjoy life in the Keys. Solid CBS construction with Bahama shutters, central air, and an updated kitchen ready for entertaining. The yard is fully fenced plus there's a large bonus shed out back. Walking distance to Publix, restaurants, and all the best local spots. Easy,

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

Experience refined coastal living at Tarpon Flats, Islamorada's most exclusive bayfront enclave. This intimate, gated community consists of just 12 luxury residences spread across four beautifully landscaped acres. A stately paver driveway welcomes you to impeccably manicured grounds, where the charm of Old Florida meets the timeless elegance of Nantucket.This three-story home offers a thoughtful

AJ Vetter Palm House Real Estate

Welcome to Serenity Cay, an exquisite Balinese-inspired estate where tranquility and luxury meet the endless beauty on the Florida Bay. A true masterpiece of engineering and design, this sprawling waterfront residence on nearly 4 acres offers an unparalleled blend of tropical elegance, sophisticated craftsmanship, and modern luxury. An expansive infinity-edge pool blends seamlessly into the

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

Introducing Isla House. A truly exceptional waterfront estate in the heart of downtown Islamorada, which exemplifies the serene beauty and elegance of Keys living. Set on a 5.82 acre double lot, Isla House overlooks 500+ feet of pristine Florida Bay waterfront. New custom construction melds traditional Caribbean architecture with clean modern aesthetics. The over 8,800 square feet of air

Kelly Shaw Pa American Caribbean Real Estate, Christie's International Real Estate

The Villas at the Islands of Islamorada is a meticulously designed, private gated community now offering fee-simple waterfront single family residences. Every comfort considered and exuding coastal living with stunning ocean views. Four bedrooms, four and one-half bathrooms three-floor villa offers 2,574 sq ft of interior plus 1,169 sq ft patios. Contemporary island architecture with an open,

The Florida Keys Sold Sisters Ocean Sotheby's International Realty

Welcome to Coral Cove Residence 3, perfectly positioned in the heart of Islamorada. This turn-key, thoughtfully designed three-bedroom, three-and-a-half-bath residence was built in 2020 and features quality construction and well-appointed appliances throughout. A beautiful open floor plan allows natural light to flow effortlessly, creating an inviting coastal living environment.Located within

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

Stunning new custom pool home in the heart of Islamorada. This exceptional, brand-new ground-level home was thoughtfully designed and expertly crafted with meticulous attention to detail. A professional interior designer curated high-end fixtures and elegant finishes throughout, creating a polished and inviting living space.Offering a rare 4-bedroom, 3-bathroom split floorplan, the home features

AJ Vetter Palm House Real Estate