219 Preston Street, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1

1/1

$834,000

Sold
Closed
Duplex
4 Beds
2 Full Baths
1,766 Sq. Ft.
Updated 12 days ago

1/1

Property 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.

Full Property Details

Full Property Details for 219 Preston St

General

Sold For: $834,000
Taxes: $7,749 (2025)
Status: Closed
Type: Duplex
Source: 927
MLS ID: 617660
Added to Site: 168 day(s) ago

Interior

Appliances: Oven, Range, Refrigerator

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 2

Bedrooms

Total Bedrooms: 4

Parking

Parking Features: Off Street

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

Central air: Yes
Air Conditioning: Yes
Cooling Type: Central Air, Ceiling Fans(s)
Heating Type: Central

Structural Information

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

Lot Features

Property View: No Waterview
Lot Size (Acres): 0.19
Lot Size (Sq. Ft.): 8,375
Zoning: SR - Settlers Residential

Water Features

Water View: Yes

Financial Considerations

Tax Amount: $7,749.71
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
Sold by Coldwell Banker Schmitt Key Largo, Jeanette Silvestri

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Listing agent

— 219 Preston St —

Patti Stanley

Coldwell Banker Schmitt Islamorada

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Schools

Schools serving 219 Preston St

School District:Monroe County School District, Middle Torch Key, FL

Name	Grades	Distance
Plantation Key School 100 Lake Road, Tavernier, FL 33070	PK-8	7.9 mi
Coral Shores High School 89901 Old Highway, Tavernier, FL 33070	9-12	8.2 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 219 Preston St

Date

Details

Price

Change

Source

5/05/2026

Sold

$834,000

-6.82%

MLS

2/27/2026

Price Reduced

$895,000

-9.6%

MLS

12/10/2025

Listed

$990,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

87851 Old Hwy, Islamorada, FL 33036 - Photo 1

Just Listed

$1,525,000

87851 Old Hwy #M42 Islamorada, FL 33036

Condo
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,736
Sq. Ft.

84961 Old Hwy, Islamorada, FL 33036 - Photo 1

Just Listed

$899,000

84961 Old Hwy #LOT 27 Islamorada, FL 33036

Single Family
Active
Updated 1 day ago

1
Bed
1
Total Bath
468
Sq. Ft.

Listed by American Caribbean Real Estate, Christie's International Real Estate, Lorie LaLonde-Miller

316 Woods Ave, Plantation Key, FL 33070 - Photo 1

Just Listed

$2,400,000

316 Woods Ave Plantation Key, FL 33070

Single Family
Active
Updated 4 days ago

4
Beds
4
Total Baths
2,793
Sq. Ft.

Listed by Coastal Realty of the Florida Keys, Claire Johnson

87851 Old Hwy, Plantation Key, FL 33036 - Photo 1

Just Listed

$1,525,000

87851 Old Hwy #M42 Plantation Key, FL 33036

Condo
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,736
Sq. Ft.

Listed by American Caribbean Real Estate, Christie's International Real Estate, Carolyn C Ambler

247 Apache St, Plantation Key, FL 33036 - Photo 1

Price Reduced

-$250,000 (-11.37%)

$1,949,000

247 Apache St Plantation Key, FL 33036

Single Family
Active
Updated 6 days ago

4
Beds
2
Total Baths
2,384
Sq. Ft.

Listed by Island Life Realty Experts, Jimmy R Lane and Island Life Realty Experts, Charity E. Rebl, P.A.

121 Lisbon Ct, Lower Matecumbe, FL 33036 - Photo 1

Price Reduced

-$125,000 (-5.68%)

$2,075,000

121 Lisbon Ct Lower Matecumbe, FL 33036

Single Family
Active
Updated 23 hours ago

3
Beds
2
Total Baths
1,228
Sq. Ft.

Listed by Coldwell Banker Schmitt Islamorada, Alina Davis

117 Leoni Dr, Plantation Key, FL 33036 - Photo 1

Price Reduced

-$350,000 (-7.07%)

$4,600,000

117 Leoni Dr Plantation Key, FL 33036

Single Family
Active
Updated 5 days ago

5
Beds
6
Total Baths
4,100
Sq. Ft.

Listed by Fairchild Partners, Inc., Michael Jones

155 Fontaine Dr, Plantation Key, FL 33070 - Photo 1

155 Fontaine Dr Plantation Key, FL 33070

Single Family
Active
Updated 1 day ago

5
Beds
4
Total Baths
2,492
Sq. Ft.

Listed by Berkshire Hathaway HomeServices Keys Real Estate - Islamorada, Katie Raskob

219 Preston St, Islamorada, FL 33036 - Photo 1

Sold

$834,000

219 Preston St Islamorada, FL 33036

Single Family
Closed

4
Beds
2
Total Baths
1,766
Sq. Ft.

81200 Overseas Hwy, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1

Sold

$910,000

81200 Overseas Hwy #7, 8, 9 Upper Matecumbe Key Islamorada, FL 33036

Multi-Family
Closed
Updated 11 days ago

0.12
Acres

Listed and Sold by Ocean Sotheby's International Realty, Leslie Leopold

82260 Overseas Hwy, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1

Sold

$880,000

82260 Overseas Hwy Upper Matecumbe Key Islamorada, FL 33036

Single Family
Closed
Updated 12 days ago

3
Beds
3
Total Baths
2,314
Sq. Ft.

Listed and Sold by Ocean Sotheby's International Realty, Sabrina Wampler & Sarah Ewald

83201 Old Hwy, Upper Matecumbe Key Islamorada, FL 33036 - Photo 1

Sold

$905,000

83201 Old Hwy #409 Upper Matecumbe Key Islamorada, FL 33036

Condo
Closed
Updated 11 days ago

2
Beds
2
Total Baths
1,275
Sq. Ft.

Listed by Palm House Real Estate, AJ Vetter and Palm House Real Estate, Drew Moret
Sold by Paradise Florida Keys Real Estate, a Luxury Brand, Richard Trottnow and Paradise Florida Keys Real Estate, a Luxury Brand, Judy Rossignol

219 Preston Street, Upper Matecumbe Key Islamorada, FL 33036 (MLS# 617660) is a Duplex property that was sold at $834,000 on May 05, 2026. Want to learn more about 219 Preston Street? Do you have questions about finding other Duplex real estate for sale in Upper Matecumbe Key Islamorada? You can browse all Upper Matecumbe Key Islamorada real estate or contact a Coldwell Banker agent to request more information.

219 Preston St Upper Matecumbe Key Islamorada, FL 33036