$4,000,000
SOLD OCT 24, 2025

37 Cannon Royal Dr Key West, FL 33040

4 Beds
5 Baths
3,750 Sq Ft
0.35 Acres

Recently Sold

$1,067 Per Sq Ft

15% Below List Price

157 Days on Market

About This Home

As of October 2025

Hidden away in the exclusive enclave of Shark Key, 37 Cannon Royal Drive offers a rare balance of architectural elegance and coastal tranquility. This four-bedroom, four-and-a-half-bath home is perfectly positioned on over third an acre of waterfront property, where walls of glass frame sweeping views of the Gulf and fill the interiors with natural light.Inside, a series of exquisite arches adds a touch of old-world charm and craftsmanship, softening transitions between spaces and lending the home a sense of timeless character. Each bedroom is a private retreat with its own en suite bath, offering comfort and privacy for both residents and guests.The open-concept layout features soaring ceilings and expansive living areas that flow effortlessly to the outdoors. A lush tropical landscape surrounds a serene pool and spa, ideal for relaxing or entertaining. Beyond, an elevated observation deck and private dock extend your living space over the water--perfect for sunset views, paddleboarding, or simply taking in the stillness of the sea.Just minutes from Key West, yet worlds away in atmosphere--this is island living, redefined.

Last Agent to Sell the Property

Dan Serban

Key West Luxury Real Estate Inc (KW) License #3313073 Listed on: 05/07/2025

Last Buyer's Agent

Christopher Santry

Last Key Realty, Inc (KW) License #3214474

Home Details

Home Type

Single Family

Est. Annual Taxes

$22,850

Year Built

1998

Lot Details

0

Listing Details

  • Property Type: Residential
  • Style: Single Family
  • First Right of Refusal: No
  • Association Fee: 1523.00
  • Mandatory HOA: Yes
  • Fee Includes: Common Area Mnt, Other, Security
  • Key Island: Shark Key
  • Limited Representation: No
  • Marathon Neighborhood: N/A
  • Mile Marker: 11.00
  • Min Rental Days: 180.00
  • M L S Identifier: 20060123165453488875000000
  • Pets: Pets Allowed
  • Property Group I D: 19990816212109142258000000
  • Sale Terms: Cash
  • Side: Bay/Gulf
  • State Province: FL
  • Taxes: 25374.12
  • Year Built: 1998
  • Alternate Key Number: 8737149
  • Lot Sq Ft: 15315.00
  • Pool Info: Above Ground, Concrete, Salt Water
  • Pool Info Heated: Yes
  • Association Maintenance Fee Per: Quarterly
  • Tax Exemptions: None
  • Building Style Above Flood: Unknown
  • Estimated Living Sq Ft: 3750.00
  • Sewer Hook Up: Yes
  • Statistical Purposes Only: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bathrooms: 5.00
  • Full Bathrooms: 4
  • Appliances: More Appliances, Freezer, Microwave, Oven, Refrigerator, Dishwasher, Dryer
  • Half Bathrooms: 1
  • Total Bedrooms: 4

Exterior Features

  • Dockage: Other Dockage
  • Waterfront: Oceanfront, Open Water, Gulf Front
  • Waterfront: Yes
  • Construction: CBS, Stucco
  • Waterview: Ocean View, Open Water View, Bay/Gulf View
  • Pool: Yes

Utilities

  • Utilities: FKAA, Municipal Sewer

Lot Info

  • Deed Restrictions: Unknown
  • Flood Zone: VE,AE
  • Parcel Number: 00159252-005600
  • Land Size: 1/4 - 1/2 Acre
  • Acres: 0.35

Rental Info

  • Rentals Allowed: With Restrictions

Tax Info

  • Tax Year: 2024

Ownership History

Date Name Owned For Owner Type

Purchase Details

Listed on
May 7, 2025
Closed on
Oct 24, 2025
Sold by
Lecrone Frank N
Bought by
Labute Joel
Seller's Agent
Dan Serban
Key West Luxury Real Estate Inc (KW)
Buyer's Agent
Christopher Santry
Last Key Realty, Inc (KW)
List Price
$4,695,000
Sold Price
$4,000,000
Premium/Discount to List
-$695,000
-14.8%
Views
1415

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
339.72%

Purchase Details

Listed on
Jun 24, 2019
Closed on
Sep 10, 2019
Sold by
Smolic Janja
Bought by
Lecmne Franklin N
Seller's Agent
Suzanne Moore
Truman & Co. (KW)
Buyer's Agent
Dan Serban
Florida Keys Realty Group, LLC (KW)
List Price
$2,700,000
Sold Price
$2,269,635
Premium/Discount to List
-$430,365
-15.94%

Home Financials for this Owner

Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
9.69%
Original Mortgage
$1,815,700
Interest Rate
3.7%
Mortgage Type
New Conventional

Purchase Details

Closed on
Mar 31, 2014
Sold by
Smolic Janja
Bought by
Smolic Janja and Janja Smolic Revocable Trust

Purchase Details

Closed on
Oct 27, 2007
Sold by
Smolic Ivo I and Smolic Jania
Bought by
Smolic Jania

Purchase Details

Closed on
Apr 26, 1996
Sold by
Shark Key Development Corp
Bought by
Smolic Ivo I and Smolic Jania
Source: Public Records

Range of Values:

--
Value Increase
--
Percent Increase
--
Adjusted for Inflation
Collateral Analytics

Collateral Analytics Collateral Analytics AVMs (Automated Valuation Model) employ a number of statistical approaches combined with neighborhood-specific comparable selection guarantees the most up-to-date and precise valuations.

Not Available

Collateral Analytics does not have data for the current month. Please view the chart for historical values.

ICE

ICE Mortgage Technology ICE Mortgage Technology’s AVM (Automated Valuation Model) is a state-of-the-art online residential property valuation tool that provides a quick and accurate estimate of the value of almost any home in the U.S.

Not Available

ICE Mortgage Technology does not have data for the current month. Please view the chart for historical values.

First American

First American First American Data & Analytics’ next-generation AVM combines unrivaled data assets with a blended ensemble of valuation models to produce highly accurate, reliable valuations you can trust.

Not Available

First American does not have data for the current month. Please view the chart for historical values.

Quantarium

Quantarium Quantarium’s valuation service, repeatedly proven the industry’s most accurate and comprehensive, is supercharged with a self-learning and auto-tuning AI engine that continually becomes smarter and more accurate as it processes daily inputs from the industry’s leading RE data lake.

Not Available

Quantarium does not have data for the current month. Please view the chart for historical values.

Average Value
Not Available
List Price
Sold Price
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area

Home Values in the Area

Source: Public Records

Average Home Value in this Area

Source: Public Records

Purchase History

Date Type Sale Price Title Company
Warranty Deed $4,000,000 None Listed On Document
Warranty Deed $2,269,635 Attorney
Interfamily Deed Transfer -- Attorney
Interfamily Deed Transfer -- Attorney
Warranty Deed $135,000 --
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Previous Owner $1,815,700 New Conventional
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
10/24/2025 10/24/25 Sold $4,000,000 -11.1% $1,067 / Sq Ft
09/27/2025 09/27/25 Price Changed $4,500,000 -4.2% $1,200 / Sq Ft
05/07/2025 05/07/25 For Sale $4,695,000 +106.9% $1,252 / Sq Ft
09/10/2019 09/10/19 Sold $2,269,635 -15.9% $556 / Sq Ft View Prior Sale
08/14/2019 08/14/19 Pending -- -- --
06/24/2019 06/24/19 For Sale $2,700,000 -- $662 / Sq Ft
Source: Key West Association of REALTORS®

Tax History Compared to Growth

Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $22,850 $3,740,041 $2,223,547 $1,516,494
2023 $22,850 $3,300,231 $1,836,843 $1,463,388
2022 $20,452 $2,843,752 $1,372,798 $1,470,954
2021 $17,017 $1,820,438 $580,056 $1,240,382
2020 $17,721 $1,878,263 $623,560 $1,254,703
2019 $9,704 $1,016,015 $0 $0
2018 $13,915 $1,388,758 $537,850 $850,908
2017 $9,510 $976,564 $0 $0
2016 $9,586 $956,478 $0 $0
2015 $9,858 $949,829 $0 $0
2014 $10,195 $942,291 $0 $0
Source: Public Records

Agents Affiliated with this Home

  • Dan Serban

    Seller's Agent in 2025

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (305) 797-2352

    11 in this area

    106 Total Sales

    Dan Serban
    Section Image
  • Christopher Santry

    Buyer's Agent in 2025

    Christopher Santry

    Last Key Realty, Inc (KW)

    (305) 304-1933

    1 in this area

    30 Total Sales

    Christopher Santry
    Section Image

  • S

    Seller's Agent in 2019

    Suzanne Moore

    Truman & Co. (KW)

  • G

    Buyer Co-Listing Agent in 2019

    George Ciupuliga

    Key West Luxury Real Estate Inc (KW)

    (305) 509-4166

    1 Total Sale

    George Ciupuliga
    Section Image
See All Agents

Map

Source: Key West Association of REALTORS®

MLS Number: 614936

Key West Association of REALTORS®

APN: 00159252-005600

Florida Monroe County Key West 33040

37 Cannon Royal Dr, Key West, FL

Sold

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Key West Association of REALTORS® IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

Nearby Homes