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

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

Location, Tax & Legal

City: ISLAMORADA Mile Marker: 82 Marathon Neighborhood: N/A Side: Ocean Flood Zone: AE Alternate Key #: 1494275 Parcel #: 00401940-000000 Zoning: SR - Settlers Residential Deed Restrictions: Unknown Legal: BK 4 LT 2 MATECUMBE BEACH PB 1-133 UPPER MATECUMBE OR598-824 OR771-19 OR820-751 OR887-2247/2248 OR962-108-AFF OR1025-49 Taxes: 7749.71 Tax Year: 2025 Pub Sewer HkUp: Yes 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 Waterfront: No Control Depth: 0 Lot SqFt: 8375 Pool: No Total Units: 0 Acres: 0.19 SqFt Source: Property Data Card Rentals Allowed: With Restrictions Min Rental Days: 28 Style: Duplex Year Built: 1934 Living Apx SqFt: 1766 Total Bedrooms: 4 Full Baths: 2 Total Baths: 2

Remarks & Misc

Remarks – Consumer: 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. Directions: If coming from the North, on Overseas Hwy, Take a left on Johnson Road, and Right on Preston.

Association Info

Mandatory Home Owners Asc: No 1st Right of Refusal: No Association Fee $: 0

Fee Includes

None: 1

Dockage

None: 1

Tax Exemptions

None: 1

Appliances

Oven: 1 Range: 1 Refrigerator: 1

Pets

Pets Allowed: 1

Cooling

Ceiling Fans(s): 1 Central Air: 1

Heating

Central: 1

Waterfront

None: 1

Waterview

No Waterview: 1

Building Style

Above Flood: Unknown Conch: 1

Vehicle Storage

Car(s): 3 Off Street Parking: 1

Construction

Combo Construction: 1 Frame: 1 Stucco: 1

Land Size

Less Than 1/4 Acre: 1

Furnished

Negotiable: 1

Utilities

Buyer to Verify: 1

Status Change Info

Status: Active

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

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.

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