Upper Matecumbe Key Islamorada FL Real Estate & Homes for Sale

Homes For Sale In Upper Matecumbe Key Islamorada FL

Exquisite Oceanfront at Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada. This MAIN LODGE OCEANFRONT, CORNER, END UNIT condotel,....

Florida Cabins |

MLS #608496

$935,000 | Active Home listing
1 Beds | 1 Baths | 840 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Maison Residences #204, a 4 bedroom and 4.5 bathroom residence, featuring an open floor plan with a grand room and oversized living terraces for oceanside living. The grand room leads into casual dining, island seating and kitchen for gatherings....

Upper Matecumbe Key Islamorada Homes |

MLS #605011

$3,195,000 | Active Home listing
4 Beds | 5 Baths | 2,539 Sqft | 0 Acres Lot

80639 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Maison Residences #201, a 4 bedroom, 4.5 bathroom residence featuring the PRIME convenience of being located first floor & pool front. Residence 201 sets itself apart from other offerings by being just steps off the back patio to the resort style....

Upper Matecumbe Key Islamorada Homes |

MLS #606541

$3,500,000 | Active Home listing
4 Beds | 5 Baths | 2,539 Sqft | 0 Acres Lot

80639 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Nothing compares to life at the one and only historic Cheeca Lodge Resort and Spa. Located in the heart of beautiful Islamorada, the sportfishing capital of the world. This is your opportunity to procure an exceptional income-producing property....

Florida Cabins |

MLS #608878

$795,000 | Active Home listing
1 Beds | 1 Baths | 550 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

SERENITY CAY is an unparalleled and extraordinary estate nestled in the heart of Islamorada. This exclusive 3.37-acre compound offers utmost privacy with its gated and fenced entrance. As you enter the property, a picturesque driveway winds....

Upper Matecumbe Key Islamorada Homes |

MLS #607949

$25,000,000 | Active Home listing
7 Beds | 9 Baths | 8,288 Sqft | 3 Acres Lot

82768 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Beautiful Downtown Islamorada Cottage! This newly constructed home is located on an oversized lot with a pool, outdoor entertaining area, plenty of storage, parking, and handicap access. The home features 3 bedrooms & 3 bathrooms with two of the....

Upper Matecumbe Key Islamorada Homes |

MLS #607840

$1,400,000 | Active Home listing
3 Beds | 3 Baths | 960 Sqft | 0 Acres Lot

81216 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Florida Cabins |

MLS #607644

$649,000 | Active Home listing
1 Beds | 1 Baths | 358 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Experience true elegance in 'Southern Paradise' - casual coastal design on the Atlantic Ocean. An unsurpassed location at Mile Marker 83 with direct 'Old Road' access for walking, biking and carting!More than 200 ft of beachfront and 1.5 acres,....

Upper Matecumbe Key Islamorada Homes |

MLS #606946

$14,000,000 | Active Home listing
7 Beds | 9 Baths | 6,696 Sqft | 2 Acres Lot

83283 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Exquisite Oceanfront Historic Cheeca Lodge Resort and Spa in Islamorada! Welcome to your unparalleled opportunity to own an exceptional income-producing property in the heart of Islamorada, the Sportfishing Capital of the World. This top floor....

Florida Cabins |

MLS #608764

$575,000 | Active Home listing
1 Beds | 1 Baths | 358 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Private, exclusive, and gorgeous describes this spacious 3 bedroom/ 3 bath recently updated townhome. The unit is located on the ocean and overlooks the white sandy beach and 155-foot pier. Features include impact glass windows and doors, an open....

Upper Matecumbe Key Islamorada Townhome |

MLS #605738

$1,825,000 | Active Home listing
3 Beds | 3 Baths | 2,251 Sqft | 0 Acres Lot

80639 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

'Coconut Cottage' beckons you to the quintessence of tropical living in Islamorada. This oceanfront haven boasts a 90ft sandy beach, a private boat basin, and an inviting waterfront pool, creating an idyllic backdrop for both....

Upper Matecumbe Key Islamorada Homes |

MLS #608791

$4,975,000 | Active Home listing
5 Beds | 4 Baths | 2,358 Sqft | 0 Acres Lot

80459 Old Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Opulent and stylish island castle; the epitome of class and luxury make this home one to remember. Located on a quiet and private island with only three residences, your secret great escape tucked away in the heart of downtown Islamorada awaits.....

Upper Matecumbe Key Islamorada Homes |

MLS #608508

$6,500,000 | Active Home listing
4 Beds | 5 Baths | 5,244 Sqft | 1 Acres Lot

80908 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Luxury meets leisure in Islamorada at this ground-level home in Bay Hammock, an exclusive gated community on Upper Matecumbe Key. 3 bedrooms, 2 bathrooms, a private swimming pool, garage, and a boat slip with a lift, this residence is a haven for....

Upper Matecumbe Key Islamorada Homes |

MLS #607822

$1,699,000 | Active Home listing
3 Beds | 2 Baths | 1,774 Sqft | 0 Acres Lot

18 Flamingo Hammock Road, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Did you say the heart of 'downtown' Islamorada!?! Well, here it is! This great 2 bedroom, 2.5 bath townhouse style condo is the perfect location! The ground floor entry leads you to two full en-suites, both accompanied by individual porches. Just....

Upper Matecumbe Key Islamorada Homes |

MLS #608198

$555,000 | Active Home listing
2 Beds | 3 Baths | 1,303 Sqft | 0 Acres Lot

80450 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Who says oceanfront living in the heart of the Florida Keys is not affordable? This cute 1-bedroom studio condo, with amazing view of Alligator Reef Lighthouse is nestled within the prestigious Palms of Islamorada. It offers 409 square feet of....

Upper Matecumbe Key Islamorada Homes |

MLS #609064

$400,000 | Active Home listing
1 Beds | 1 Baths | 409 Sqft | 0 Acres Lot

79901 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

**Nightly Rental Condotel at Historic Cheeca Lodge Resort and Spa**1. **Condo Features**: - Private King bedroom with full-size soaking bathtub and private dressing area - Spacious separate living room with queen sofa-bed - Fully equipped....

Florida Cabins |

MLS #609208

$775,000 | Active Home listing
1 Beds | 1 Baths | 550 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

One of a kind property in central Islamorada! Exceptional opportunity to own this detached Condominium/Home which sits apart and on its own providing a single family home atmosphere and includes a 2 car garage/storage. Large and spacious two....

Upper Matecumbe Key Islamorada Homes |

MLS #608358

$1,100,000 | Active Home listing
5 Beds | 3 Baths | 3,264 Sqft | 0 Acres Lot

80450 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Located on Upper Matecumbe Key in Islamorada this property boasts a 1/1 frame house as well as a 2/1 CBS house on an 8,100 sq ft lot on a quiet dead-end street. The Cbs house was remodeled a few years ago and has been consistently rented on a....

Upper Matecumbe Key Islamorada Homes |

MLS #607656

$1,250,000 | Active Home listing
2 Beds | 1 Baths | 928 Sqft | 0 Acres Lot

207 Russell Street, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

Own a piece of the legendary Cheeca Lodge Resort and Spa. Located in Islamorada, the ''Sportfishing Capital of the World''. Condo Features -This spacious King Bed Suite offers a large living room area with a pull-out queen bed, a grand bathroom....

Florida Cabins |

MLS #609862

$725,000 | Active Home listing
1 Beds | 1 Baths | 550 Sqft | 0 Acres Lot

81801 Overseas Highway, Upper Matecumbe Key Islamorada, FL 33036 Monroe County

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