39 Evergreen Dr

6,611 Sq. Ft.
$877 / Sq. Ft.
6,611
Sq. Ft.
$877
per Sq. Ft.

Description

Tucked within an exclusive Key Haven cul-de-sac, Casa di Sempre is a European-inspired waterfront estate offering more than 260 linear feet of water frontage across two sides of the property, including 200 feet of concrete dockage for boating enthusiasts. Resting on over 15,000 square feet of land, this residence showcases superior craftsmanship and thoughtful design throughout more than 6,500 square feet of refined living space. The main residence features five bedrooms and four-and-a-half baths,...Tucked within an exclusive Key Haven cul-de-sac, Casa di Sempre is a European-inspired waterfront estate offering more than 260 linear feet of water frontage across two sides of the property, including 200 feet of concrete dockage for boating enthusiasts. Resting on over 15,000 square feet of land, this residence showcases superior craftsmanship and thoughtful design throughout more than 6,500 square feet of refined living space. The main residence features five bedrooms and four-and-a-half baths, while a three-bedroom, three-bath guest villa provides privacy and comfort for visitors. Constructed of 11-inch insulated concrete forms with poured concrete floors and stairs, the home provides extraordinary strength, safety, and sound insulation. Impact glass windows and doors are complemented by hidden European-style roll-down shutters, ensuring both security and elegance. Inside, an open gourmet kitchen, formal dining room, study, and three fireplaces create a warm yet sophisticated ambiance. Eight-foot mahogany interior doors and windows elevate each space with timeless craftsmanship. Outdoors, the estate is a true entertainer's haven, highlighted by a 65-foot heated glass-mosaic pool with a 21-foot infinity edge, three cascading waterfalls, and an island with a six-seat swim-up bar leading to a custom cabana. A private 400-square-foot gym and 3,800-square-foot garage complete the amenities, along with a generator and fire suppression system for added peace of mind. A rare combination of elegance, engineering, and waterfront grandeur, Casa di Sempre represents one of the most remarkable estates in the Lower Florida Keys--crafted for those who value strength, sophistication, and sanctuary by the sea.
  1. Listed by Sabrina Wampler & Sarah Ewald • Ocean Sotheby's International Realty

Property Details for 39 Evergreen Drive

Waterfront
Canal Front
Waterfront
Yes
Zoning
IS - Improved Subivision District
Subdivision
Key Haven 10th Add (5.0)
Directions
GPS
Vehicle Storage
Garage, Trailer Storage, Guest Parking, Open Parking, Auto Door Opener, Attached
Pets
Pets Allowed
LISTING UPDATED: 12/27/2025 05:15 PM

Property Details for 39 Evergreen Drive

StatusPending
MLS #616954
Days on Market68
Taxes$51,426 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built2001
Lot Size0.36 AC / 15,687 SF
CountyMonroe County

Location

Listing Courtesy of Ocean Sotheby's International Realty
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Building Information for 39 Evergreen Drive

Stories-Year Built2001Building Size-Lot Size0.36 AC / 15,687 SF

Payment Calculator

$32,554 per month

30 year fixed, 6.15% Interest

Principal and Interest

$28,268

Property Taxes

$4,286

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 39 Evergreen Drive

Summary
Location and General Information
  • Waterview: Canal View
  • Area: 05 - Stock Island to Shark Key
  • Absolute Longitude: 81.739304
  • Control Depth: 4
  • Listing Board: Florida Keys
  • Side: Bay/Gulf
  • Mile Marker: 5.0
  • Marathon Neighborhood: N/A
  • Key/Island: Key Haven
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: 2024
  • Tax Exemptions: None
Virtual Tour
Property
Lot Information
  • Acres: 0.36
  • Parcel #: 00140440-000000
  • Land Size: 1/4 - 1/2 Acre
Property and Assessments
  • Legal: BK 4 LT 16 KEY HAVEN TENTH ADDITION RACCOON KEY PB-5-114 OR939-2206 OR1492-101 OR1511-1674/75 OR1511-1676/77 OR1562-1737
  • MLS Approved: Y
  • SqFt Source: Tax Records
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 99
  • Document Count: 0
  • Building Style: Above Flood: Unknown
  • Property Condition: Updated/Remodeled
  • Title: Negotiable
Utilities
  • Utilities: FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Pool: Yes
  • Pool Info: Heated: Yes
  • Pool Info: In Ground
  • Porch/Balcony: Open Porch/Balcony, Deck, Patio, Roof Top Deck
Interior and Exterior Features
Interior Features
  • Floor: Tile, Marble, Carpet
  • Interior Features: Wet Bar, Built-in Cabinets, Tray Ceilings, Bar, Walk-in Closet(s), Storage, Sky Light(s), Lobby, Granite Counter Top, Entrance Foyer, Fireplace(s), Split Bedroom, Cathedral Ceilings
  • Pre-Wired: Cable
  • Appliances: Washer, Stainless Steel Appliance(s), Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
Exterior Features
  • Roof: Metal Roof
  • Shutters: Roll Down Electric
  • Dockage: Dock Length: 180
  • Dockage: Dock: Concrete
  • Construction: CBS, ICFs (Insulated Concrete Forms), Combo Construction, Concrete
  • Dockage: Boat Lift
  • Exterior Features: Bar, Storage, Privacy Wall/Fence, Outdoor Shower, Outdoor Kitchen, Lanai, Lighting, Rain Gutters, Detached Guest Qtrs, Gazebo, Fencing, Chickee Hut, Built-in Grill
  • Windows/Doors: Glass Doors, Sliding Glass Doors
Room Information
  • Specialty Rooms: Gym, Laundry Room
  • Specialty Rooms: Guest/Servant Qtrs: Legal

Property History for 39 Evergreen Drive

DateEvent & SourcePriceAppreciation
Dec 27, 2025

Pending

FKMLS #616954

Dec 26, 2025

Listed (Active)

FKMLS #616954

Dec 11, 2025

Backup Contract

FKMLS #616954

Oct 20, 2025

Listed (Active)

FKMLS #616954

$5,800,000
Oct 3, 2025

Expired

FKMLS #611707

Jul 31, 2025

Temp Off Market

FKMLS #611707

Oct 3, 2024

Price Change

FKMLS #611707

$6,999,000
Oct 3, 2024

Price Change

FKMLS #611707

$6,899,000
Oct 3, 2024

Price Change

FKMLS #611707

$6,799,000
Oct 3, 2024

Price Change

FKMLS #611707

$6,699,000
Oct 3, 2024

Price Change

FKMLS #611707

$5,999,000
Oct 3, 2024

Listed (Active)

FKMLS #611707

$5,799,000
Sep 26, 2024

Expired

FKMLS #606778

Sep 26, 2023

Price Change

FKMLS #606778

$8,199,000
Sep 26, 2023

Price Change

FKMLS #606778

$7,999,000
Sep 26, 2023

Price Change

FKMLS #606778

$7,799,000
Sep 26, 2023

Price Change

FKMLS #606778

$7,699,000
Sep 26, 2023

Listed (Active)

FKMLS #606778

$6,999,000
May 20, 2020

Sold

FKMLS #589942

$7,000,000
May 20, 2020

Sold

FKMLS #589942

$5,600,000
May 19, 2020

Pending

FKMLS #589942

Feb 22, 2020

Listed (Active)

FKMLS #589942

$7,000,000
Feb 7, 2020

Expired

FKMLS #586855

$6,500,000
Aug 7, 2019

Listed (Active)

FKMLS #586855

$6,500,000
Jul 25, 2019

Expired

FKMLS #584005

$6,900,000
Jan 29, 2019

Listed (Active)

FKMLS #584005

$6,900,000
DateEvent & SourcePrice
12/27/2025

Pending

FKMLS #616954

12/26/2025

Listed (Active)

FKMLS #616954

12/11/2025

Backup Contract

FKMLS #616954

10/20/2025

Listed (Active)

FKMLS #616954

$5,800,000
10/03/2025

Expired

FKMLS #611707

07/31/2025

Temp Off Market

FKMLS #611707

10/03/2024

Price Change

FKMLS #611707

$6,999,000
10/03/2024

Price Change

FKMLS #611707

$6,899,000
10/03/2024

Price Change

FKMLS #611707

$6,799,000
10/03/2024

Price Change

FKMLS #611707

$6,699,000
10/03/2024

Price Change

FKMLS #611707

$5,999,000
10/03/2024

Listed (Active)

FKMLS #611707

$5,799,000
09/26/2024

Expired

FKMLS #606778

09/26/2023

Price Change

FKMLS #606778

$8,199,000
09/26/2023

Price Change

FKMLS #606778

$7,999,000
09/26/2023

Price Change

FKMLS #606778

$7,799,000
09/26/2023

Price Change

FKMLS #606778

$7,699,000
09/26/2023

Listed (Active)

FKMLS #606778

$6,999,000
05/20/2020

Sold

FKMLS #589942

$7,000,000
05/20/2020

Sold

FKMLS #589942

$5,600,000
05/19/2020

Pending

FKMLS #589942

02/22/2020

Listed (Active)

FKMLS #589942

$7,000,000
02/07/2020

Expired

FKMLS #586855

$6,500,000
08/07/2019

Listed (Active)

FKMLS #586855

$6,500,000
07/25/2019

Expired

FKMLS #584005

$6,900,000
01/29/2019

Listed (Active)

FKMLS #584005

$6,900,000

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

Schools near 39 Evergreen Drive

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 5
Charter - K to 8
Public - 9 to 12
Charter - 9 to 12
Rating
School
Distance
Gerald Adams Elementary School
PublicPK to 5

Sigsbee Charter School
CharterK to 8

Key West High School
Public9 to 12

The College Of The Florida Keys Academy
Charter9 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.

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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. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Ocean Sotheby's International Realty

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.