219 Preston St

1,766 Sq. Ft.
$561 / Sq. Ft.
1,766
Sq. Ft.
$561
per Sq. Ft.

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....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.
  1. Listed by Patti Stanley • Coldwell Banker Schmitt Islamorada

Property Details for 219 Preston Street

Waterfront
None
Waterfront
No
Zoning
SR - Settlers Residential
Subdivision
Matecumbe Beach (82.0)
Directions
If coming from the North, on Overseas Hwy, Take a left on Johnson Road, and Right on Preston.
Building Style
Conch
Vehicle Storage
Off Street Parking
Pets
Pets Allowed
LISTING UPDATED: 02/20/2026 01:27 PM

Property Details for 219 Preston Street

StatusActive
MLS #617660
Days on Market74
Taxes$7,750 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeMulti Family
MLS TypeResidential / Duplex
Year Built1934
Lot Size0.19 AC / 8,375 SF
CountyMonroe County

Location

Listing Courtesy of Coldwell Banker Schmitt Islamorada
Add your commute

Building Information for 219 Preston Street

Stories-Residences-Year Built1934Building Size-Lot Size0.19 AC / 8,375 SF

Payment Calculator

$5,471 per month

30 year fixed, 6.15% Interest

Principal and Interest

$4,825

Property Taxes

$646

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 219 Preston Street

Summary
Location and General Information
  • Waterview: No Waterview
  • Area: 23 - Upper Matecumbe
  • Absolute Longitude: 80.63573
  • Control Depth: 0
  • Listing Board: Florida Keys
  • Side: Ocean
  • Mile Marker: 82.0
  • Marathon Neighborhood: N/A
  • Key/Island: Upper Matecumbe Key Islamorada
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Furnished: Negotiable
  • Tax Year: 2025
  • Tax Exemptions: None
Property
Lot Information
  • Acres: 0.19
  • Parcel #: 00401940-000000
  • Land Size: Less Than 1/4 Acre
Property and Assessments
  • 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
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 31
  • Document Count: 1
  • Building Style: Above Flood: Unknown
Utilities
  • Utilities: Buyer to Verify
  • Pub Sewer HkUp: Yes
  • Pool: No
Interior and Exterior Features
Interior Features
  • Appliances: Refrigerator, Oven, Range
Exterior Features
  • Construction: Frame, Combo Construction, Stucco
  • Dockage: None

Property History for 219 Preston Street

DateEvent & SourcePriceAppreciation
Jan 7, 2026

Listed (Active)

FKMLS #617989

$990,000
Dec 10, 2025

Listed (Active)

MFRMLS #TB8435119

$990,000
Dec 10, 2025

Listed (Active)

MiamiRE #A11928795

$990,000
Dec 10, 2025

Listed (Active)

FKMLS #617660

$990,000
Dec 10, 2025

Listed (Active)

RAPB #RX-11146822

$990,000
Nov 26, 2025

Temp Off Market

FKMLS #616583

Nov 26, 2025

Cancelled

RAPB #RX-11130023

Nov 26, 2025

Cancelled

MFRMLS #TB8435119

$1,250,000
Nov 26, 2025

Cancelled

MiamiRE #A11891298

Oct 20, 2025

Listed (Active)

MFRMLS #TB8435119

$1,250,000
Oct 6, 2025

Listed (Active)

RAPB #RX-11130023

$1,250,000
Oct 6, 2025

Listed (Active)

MiamiRE #A11891298

$1,250,000
Sep 22, 2025

Listed (Active)

FKMLS #616583

$1,250,000
Mar 17, 2016

Sold (Public Record)

Public Record #569715795

$482,000

+16.3% / yr

Mar 17, 2016

Sold

FKMLS #569982

$482,000
Mar 1, 2016

Pending

FKMLS #569982

Feb 9, 2016

Listed (Active)

FKMLS #569982

$510,000
Aug 12, 2014

Sold (Public Record)

Public Record #434387481

$379,000

+0.3% / yr

Apr 15, 2006

Expired

FKMLS #531420

Oct 15, 2005

Listed (Active)

FKMLS #531420

$699,000
Jun 10, 2003

Sold (Public Record)

Public Record #116676333

$366,300

+102.9% / yr

May 29, 2003

Sold

FKMLS #516372

$366,225
May 5, 2003

Pending

FKMLS #516372

May 2, 2003

Listed (Active)

FKMLS #516372

$395,000
Feb 20, 2003

Sold (Public Record)

Public Record #110303117

$296,000
Feb 19, 2003

Sold

FKMLS #513442

$296,000
Jan 12, 2003

Pending

FKMLS #513442

Oct 7, 2002

Listed (Active)

FKMLS #513442

$345,000
Feb 8, 2001

Expired

FKMLS #501639

Mar 5, 2000

Listed (Active)

FKMLS #501639

$270,000
DateEvent & SourcePrice
01/07/2026

Listed (Active)

FKMLS #617989

$990,000
12/10/2025

Listed (Active)

MFRMLS #TB8435119

$990,000
12/10/2025

Listed (Active)

MiamiRE #A11928795

$990,000
12/10/2025

Listed (Active)

FKMLS #617660

$990,000
12/10/2025

Listed (Active)

RAPB #RX-11146822

$990,000
11/26/2025

Temp Off Market

FKMLS #616583

11/26/2025

Cancelled

RAPB #RX-11130023

11/26/2025

Cancelled

MFRMLS #TB8435119

$1,250,000
11/26/2025

Cancelled

MiamiRE #A11891298

10/20/2025

Listed (Active)

MFRMLS #TB8435119

$1,250,000
10/06/2025

Listed (Active)

RAPB #RX-11130023

$1,250,000
10/06/2025

Listed (Active)

MiamiRE #A11891298

$1,250,000
09/22/2025

Listed (Active)

FKMLS #616583

$1,250,000
03/17/2016

Sold (Public Record)

Public Record #569715795

$482,000

+16.3% / yr

03/17/2016

Sold

FKMLS #569982

$482,000
03/01/2016

Pending

FKMLS #569982

02/09/2016

Listed (Active)

FKMLS #569982

$510,000
08/12/2014

Sold (Public Record)

Public Record #434387481

$379,000

+0.3% / yr

04/15/2006

Expired

FKMLS #531420

10/15/2005

Listed (Active)

FKMLS #531420

$699,000
06/10/2003

Sold (Public Record)

Public Record #116676333

$366,300

+102.9% / yr

05/29/2003

Sold

FKMLS #516372

$366,225
05/05/2003

Pending

FKMLS #516372

05/02/2003

Listed (Active)

FKMLS #516372

$395,000
02/20/2003

Sold (Public Record)

Public Record #110303117

$296,000
02/19/2003

Sold

FKMLS #513442

$296,000
01/12/2003

Pending

FKMLS #513442

10/07/2002

Listed (Active)

FKMLS #513442

$345,000
02/08/2001

Expired

FKMLS #501639

03/05/2000

Listed (Active)

FKMLS #501639

$270,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 219 Preston Street

Taxable ValueLand-Additions-Total-
Tax Record2024$7,824 ($652 / month)
Home Facts
Baths3Total Finished SqFt900 SqFtAbove Grade Finished SqFt900 SqFtStories1Lot Size8,375 SqFtStyleMulti-Family Dwelling (2-4)Year Built1934Year Renovated2009CountyMONROEAPN00401940-000000

Schools near 219 Preston Street

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Charter - PK to 8
Public - 6 to 12
Rating
School
Distance
Plantation Key School
PublicPK to 8

Coral Shores High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

219 Preston Street is a multi-family home for sale in Islamorada, FL 33036. This property was listed for sale on December 10, 2025 by Coldwell Banker Schmitt Islamorada, it's currently listed at $990,000. It has been on the market for a total of 74 days and was last sold on March 17, 2016. This listing's school district is Monroe. Nearby schools include Plantation Key School, Coral Shores High School and Treasure Village Montessori Charter School. 219 Preston Street is a 4-bed, 2-bath, 1,766 sqft multi-family home built in 1934.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of Coldwell Banker Schmitt Islamorada

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.