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$990,000

  • For Sale
  • Active
  • Duplex
  • 4 Beds
  • 2 Full Baths
  • 1,766 Sq. Ft.
  • Updated 8 days ago

Next open house:

Open House: 11:00 AM - 1:00 PM

Saturday 1/17 11:00 AM - 1:00 PM

219 Preston Street,Islamorada, FL 33036

219 Preston StreetIslamoradaFL33036

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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.

Full Property Details for 219 Preston St

General

  • Price: $990,000
  • Taxes: $7,749 (2025)
  • Status: Active
  • Type: Duplex
  • Source: 927
  • MLS ID: 617660
  • Updated: 1/7/2026
  • Added to Site: 37 day(s) ago

Interior

  • Appliances: Refrigerator, Oven, Range
  • Furnishings: Negotiable

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4

Parking

  • Garage Spaces: 3
  • Total Spaces: 3
  • Parking: Off Street Parking

Location

  • Area: 23 - Upper Matecumbe
  • County: Monroe
  • Subdivision: Matecumbe Beach (82.0)
  • Driving Directions: If coming from the North, on Overseas Hwy, Take a left on Johnson Road, and Right on Preston.

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Cooling Type: Central Air, Ceiling Fans(s)
  • Heating Type: Central

Utilities

  • Water: No Waterview
  • Utility Description: Buyer to Verify

Structural Information

  • Architectural Style: Duplex
  • Construction: Frame, Combo Construction, Stucco
  • Square Feet: 1,766
  • Sq. Ft. Source: Property Data Card
  • Year Built: 1934

Lot Features

  • Lot Size (Sq. Ft.): 8,375
  • Zoning: SR - Settlers Residential

Water Features

  • Water View: Yes
  • Water Front Type: None
  • Dock Description: None

Financial Considerations

  • Tax Amount: $7,749
  • Tax Year: 2025

Disclosures and Reports

  • Legal Description: 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
  • Flood Zone: AE
  • APN: 00401940-000000

Listed by Coldwell Banker Schmitt Islamorada, Patti Stanley (305) 393-4433

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Listing agent

— 219 Preston St —

  • Patti Stanley

    Coldwell Banker Schmitt Islamorada

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 219 Preston St

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Plantation Key School
100 Lake Road, Tavernier, FL 33070
PK-87.9 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-1275.9 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 219 Preston St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/10/2025
Listed
$990,000
105.39%
MLS
3/17/2016
Sold
$482,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 219 Preston St

Year
Property Taxes
Change
Tax Assessment
Change
2024
$7,824
—
$715,753
3%
2024
$7,824
1%
$695,582
3%
2023
$7,774
2%
$675,323
3%
2022
$7,653
19%
$655,654
38%
2021
$6,430
—
$476,635
14%
2021
$6,430
6%
$417,315
—
2019
$6,059
2%
$416,023
2%
2018
$5,913
2%
$408,724
-1%
2017
$5,824
3%
$411,609
9%
2016
$5,653
9%
$378,909
14%
2015
$5,196
30%
$333,123
55%
2014
$3,982
4%
$214,864
8%
2013
$3,826
—
$198,280
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Coldwell Banker Schmitt Islamorada, Patti Stanley (305) 393-4433

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Price Reduced near 219 Preston St

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140 Tavern Dr, Tavernier, FL 33070 - Photo 1 Price Reduced
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219 Preston Street, Islamorada, FL 33036 (MLS# 617660) is a Duplex property with 4 bedrooms and 2 full bathrooms. 219 Preston Street is currently listed for $990,000 and was received on December 10, 2025. Want to learn more about 219 Preston Street? Do you have questions about finding other Duplex real estate for sale in Islamorada? You can browse all Islamorada real estate or contact a Coldwell Banker agent to request more information.

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