219 Preston Street, Upper Matecumbe Key Islamorada, FL 33036

$895,000
Property Type: Residential Bedrooms: 4 Baths: 2 Square Footage: 1,766 Lot Size (sq. ft.): 8,375 Status: Active
Current Price: $895,000 List Date: 12/10/2025 Last Modified: 2/27/2026

Description

Back on market with Huge Price Improvement! Rare Downtown Islamorada Opportunity... Just steps to the ocean, sunrises and sunsets. Walk to everything you love in Islamorada! Located just off the Old Hwy, oceanside, in the sought-after Matecumbe Beach neighborhood on Upper Matecumbe Key. This versatile property features two charming cottages on one property, just steps from festivals, the Arts District, Library Beach, Cheeca Lodge, Historical Hurricane Monument and some of the island's finest dining. The front cottage offers 2 bedrooms and 1 bath with +/-866 sq. ft., while the back cottage includes 2 bedrooms and 1 bath with +/-900 sq. ft. Enjoy the option to live in one and rent the other, or maximize income by renting both. An exceptional investment in a prime location, right in the heart of Islamorada's most vibrant and walkable district. Important Note: This property is also listed separately in the MLS under 2 different classifications intentionally: Single Family Home and Duplex/multifamily as it can be used for both.

More Information MLS# 617660

Contract Information

Current Price: $895,000 Listing Date: 2025-12-10 Listing Board: Florida Keys List Price: $895,000

Location Tax Legal

Street #: 219 Street Name: Preston Street Suffix: Street Key/Island: Upper Matecumbe Key Islamorada State/Province: FL Zip Code: 33036 County: Monroe Subdivision: Matecumbe Beach (82.0) Area: 23 - Upper Matecumbe

General Property Description

Realtor.COM Type: Multi-family Style: Duplex Waterfront: No Pool: No Year Built: 1934 Lot SqFt: 8375 Acres: 0.19 Living Apx SqFt: 1766 SqFt Source: Property Data Card Total Bedrooms: 4 Full Baths: 2 Total Baths: 2 Rentals Allowed: With Restrictions Min Rental Days: 28

Status Change Info

Status: Active

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No

Building Style

Above Flood: Unknown

Vehicle Storage

Car(s): 3

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Building Style: Conch Vehicle Storage: Off Street Parking Furnished: Negotiable Cooling: Ceiling Fans(s); Central Air Heating: Central Utilities: Buyer to Verify Appliances: Oven; Range; Refrigerator Construction: Combo Construction; Frame; Stucco Pets: Pets Allowed Land Size: Less Than 1/4 Acre
Listing Office: Coldwell Banker Schmitt Islamorada
Last Updated: February - 27 - 2026
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