Darrin Smith

Key West FL

Key West Luxury Real Estate Inc (KW)

65 Closed Sales

$69.9M Total Value

$412.7K - $4.6M Price Range

$1.1M Average Price

Prior 5 years

About Darrin

Home Types: MultiFamily, House, Townhouse, Commercial, Condo, Lot/Land

Years of Experience: 12

Transaction History

1 Year
2 Year
5 Year

Seller Deals
Total Deals	4
Total Value	$4,700,000
Average Sale Price	$1,175,000
Price Range	$1M - $1.3M

Buyer Deals
Total Deals	1
Total Value	$1,159,500
Average Sale Price	$1,159,500

Seller Deals
Total Deals	6
Total Value	$6,405,000
Average Sale Price	$1,067,500
Price Range	$830K - $1.3M

Buyer Deals
Total Deals	7
Total Value	$12,072,500
Average Sale Price	$1,724,643
Price Range	$675K - $4.6M

Seller Deals
Total Deals	41
Total Value	$39,293,175
Average Sale Price	$958,370
Price Range	$16K - $3M

Buyer Deals
Total Deals	24
Total Value	$30,650,750
Average Sale Price	$1,277,115
Price Range	$445K - $4.6M

5 Year View

Neighborhoods Darrin is Experienced In

Darrin's Open Houses

$1,055,000

Open Sun 12PM - 2PM
- 3 Beds
- 3 Baths
- 1,797 Sq Ft
1421 12th St

Key West, FL
Welcome to 1421 12th St, a stunning oasis nestled in the heart of Key West. This charming property perfectly combines island living with modern convenience, offering an exceptional opportunity for both homeowners and investors alike. As you step inside, you are greeted by an open-concept layout that maximizes space and natural light. The living area boasts high ceilings and beautiful finishes,

Darrin Smith Key West Luxury Real Estate Inc (KW)

$2,395,000

Open Thu 10AM - 12PM
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
319 Grinnell St

Key West, FL
Introducing 319 Grinnell Street, a captivating residence in the heart of Key West's Historic Seaport, where charm and character abound. This beautifully framed Key West-style home reflects the rich tapestry of the area's history, showcasing classic architecture with inviting porches and intricate details that honor the past. Nestled among a collection of historic homes, 319 Grinnell Street offers

Darrin Smith Key West Luxury Real Estate Inc (KW)

Darrin's Active Listings

$735,000
- 2 Beds
- 1 Bath
- 745 Sq Ft
906 Truman Ave

Unit 1

Key West, FL
This performing vacation rental sold as shown is a beautiful property which exudes a sense of warmth and character from the moment you set eyes on it. As you approach the home, you are greeted by a picturesque facade that captures the essence of Key West architecture. The vibrant colors and tropical landscaping create a welcoming atmosphere that invites you to step inside and explore further.

Darrin Smith Key West Luxury Real Estate Inc (KW)

Joint Agent

$624,500
- 2 Beds
- 1 Bath
- 780 Sq Ft
81 Golf Club Dr

Key West, FL
**Golf course frontage. No rear neighbors. Minutes to Old Town Key West.** Welcome to your private island retreat in the sought-after Key West Golf Club community on Stock Island. Overlooking the first green of the Rees Jones-designed golf course, this beautifully updated 2-bedroom, 1.5-bath home offers a rare combination of privacy, scenic views, and resort-style living. Inside, the

Darrin Smith Key West Luxury Real Estate Inc (KW)

$3,400
- 2 Beds
- 1.5 Baths
- 780 Sq Ft
32 Merganser Ln

Key West, FL
Discover your perfect long-term rental in the heart of Key West Golf Club! This charming 780 sqft property offers an ideal blend of comfort and convenience, perfect for those looking to embrace the vibrant lifestyle of this tropical haven. For some work distances it is 2.5 miles from Naval Air Station Boca Chica, 5.1 miles from US Coast Guard Sector Key West Trumbo Point, 6.1 miles from JIATF

Darrin Smith Key West Luxury Real Estate Inc (KW)

Recently Sold

$1,200,000

Sold May 11, 2026
- 4 Beds
- 3 Baths
- 1,578 Sq Ft
2105 Fogarty Ave

Key West, FL
- 20% Below List
- $760/SF
- 156 Days On Market
- Current Est. Value $1M
Darrin Smith Key West Luxury Real Estate Inc (KW)

$1,000,000

Sold Mar 13, 2026
- 3 Beds
- 2 Baths
- 1,232 Sq Ft
2525 Patterson Ave

Key West, FL
- 23% Below List
- $812/SF
- 279 Days On Market
- Current Est. Value $1M
Darrin Smith Key West Luxury Real Estate Inc (KW)

$1,250,000

Sold Jul 18, 2025
- 2 Beds
- 1 Bath
- 792 Sq Ft
530 Grinnell St

Key West, FL
- 24% Below List
- $1,578/SF
- 47 Days On Market
- Current Est. Value $1M
Darrin Smith Key West Luxury Real Estate Inc (KW)

$830,000

Sold Dec 19, 2024
- 2 Beds
- 1 Bath
- 580 Sq Ft
620 Thomas St

Unit 286

Key West, FL
- 8% Below List
- $1,431/SF
- 88 Days On Market
- Current Est. Value $799K
Darrin Smith Key West Luxury Real Estate Inc (KW)

$620,000

Sold May 26, 2023
- 2 Beds
- 1 Bath
- 780 Sq Ft
28 Merganser Ln

Key West, FL
- 4% Below List
- $795/SF
- 24 Days On Market
- Current Est. Value $654K
Darrin Smith Key West Luxury Real Estate Inc (KW)

$1,400,000

Sold Oct 29, 2021
- 3 Beds
- 4 Baths
- 2,074 Sq Ft
1701 Jamaica Dr

Key West, FL
- 30% Below List
- $675/SF
- 33 Days On Market
- Current Est. Value $2M
Darrin Smith Key West Luxury Real Estate Inc (KW)

$650,000

Sold Oct 8, 2021
- 3 Beds
- 1 Bath
- 1,193 Sq Ft
1707 Bertha St

Key West, FL
- 10% Below List
- $545/SF
- 38 Days On Market
- Current Est. Value $919K
Darrin Smith Key West Luxury Real Estate Inc (KW)

$1,250,000

Sold Sep 24, 2021
- 2 Beds
- 2 Baths
- 1,085 Sq Ft
618 White St

Key West, FL
- 3% Below List
- $1,152/SF
- 23 Days On Market
- Current Est. Value $1M
Darrin Smith Key West Luxury Real Estate Inc (KW)

$895,000

Sold Aug 9, 2021
- 4 Beds
- 2 Baths
- 1,308 Sq Ft
1424 Catherine St

Key West, FL
- 1% Below List
- $684/SF
- 84 Days On Market
- Current Est. Value $1M
Darrin Smith Key West Luxury Real Estate Inc (KW)

Awards and Designations

NAR - National Association of Realtors

Agent License: Florida 3291885 New Mexico 3291885

Darrin Smith

(813) 850-0259

Key West Luxury Real Estate Inc (KW)

(813) 850-0259

Homes for Sale by City

Darrin Smith

About Darrin

Transaction History

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Seller Deals

Buyer Deals

Production Over Time

5 Year View

Neighborhoods Darrin is Experienced In

Darrin's Listings and Deals

Darrin's Open Houses

Darrin's Active Listings

Recently Sold

Awards and Designations