1614 Dennis Street, Key West, FL 33040

$1,499,000
Property Type: Residential Bedrooms: 7 Baths: 4 Square Footage: 2,699 Lot Size (sq. ft.): 5,056 Status: Active
Current Price: $1,499,000 List Date: 1/16/2026 Last Modified: 1/20/2026

Description

1614 Dennis St is a rare income-producing triplex offering strong cash flow and flexible use in the heart of Key West. Generating over $125,000 annually in rental income, this well-configured property features three separate units, each with its own washer and dryer, making it highly desirable for long-term tenants and employee housing. The layout includes two spacious 2-bedroom / 1-bath units and an upstairs 3-bedroom / 2-bath residence, providing multiple rental strategies and value-add potential. A standout feature is parking for up to 7 vehicles—a true luxury in Key West and a major draw for tenants. Large Shed on property with two dedicated spaces that could be converted into a workspace. Ideal for investors seeking steady returns or employers looking for quality workforce housing, this triplex combines strong income, practical design, and exceptional parking in one compelling opportunity. Please note some photos were digitally staged and or altered to protect tenant privacy.

More Information MLS# 618151

Contract Information

Current Price: $1,499,000 Listing Date: 2026-01-16 Listing Board: Key West Association List Price: $1,499,000

Location Tax Legal

Street #: 1614 Street Name: Dennis Street Suffix: Street Key/Island: Key West State/Province: FL Zip Code: 33040 County: Monroe Subdivision: New Town - Unrecord (3.0) Area: 03 - Key West

General Property Description

Realtor.COM Type: Multi-family Style: Multi-Units Waterfront: No Pool: No Year Built: 1968 Lot Size: 55 X 92 Lot SqFt: 5056 Acres: 0.12 Living Apx SqFt: 2699 SqFt Source: Tax Records Total Bedrooms: 7 Full Baths: 4 Total Baths: 4 Rentals Allowed: Yes

Status Change Info

Status: Active

Association Info

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

Building Style

Above Flood: Unknown Stories: 2 Stories

Vehicle Storage

Car(s): 4+

Property Features

Fee Includes: None Tax Exemptions: None Waterfront: None Waterview: No Waterview Dockage: None Property Condition: Fixer Upper Vehicle Storage: Off Street Parking Furnished: Unfurnished Cooling: Ceiling Fans(s); Central Air Utilities: Buyer to Verify; FKAA Interior Features: Cathedral Ceilings; Smoke Alarms Appliances: Dishwasher; Dryer; Range; Refrigerator; Washer Exterior Features: Shed Construction: CBS; Combo Construction; Frame Floor: Combo; Tile; Vinyl Roof: Combo Roof; Metal Roof Pets: Pets Allowed Land Size: Less Than 1/4 Acre Terms: Cash; Conventional Title: Negotiable
Listing Office: Ocean Sotheby's International Realty
Last Updated: January - 20 - 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.