Seller's Agent in 2026
The Florida Keys Sold Sisters
Ocean Sotheby's International Realty
(305) 393-0585
81 Total Sales
39 Evergreen Ave Key West, FL 33040
8
Beds
9.5
Baths
6,611
Sq Ft
15,682
Sq Ft Lot
Highlights
- Dock made with concrete
- Boat Lift
- Home fronts a canal
- Detached Guest House
- Heated In Ground Pool
- Maid or Guest Quarters
About This Home
As of January 2026Tucked 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.
Last Agent to Sell the Property
Ocean Sotheby's International Realty Listed on: 10/20/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $51,426
Year Built
- Built in 2001 | Remodeled
Lot Details
- 0.36 Acre Lot
- Home fronts a canal
- Privacy Fence
- Fenced
- Property is zoned IS - Improved Subivision District
Home Design
- Insulated Concrete Forms
- Metal Roof
- Pre-Cast Concrete Construction
Interior Spaces
- 6,611 Sq Ft Home
- Wet Bar
- Bar
- Tray Ceiling
- Cathedral Ceiling
- Skylights
- Fireplace
- Sliding Doors
- Entrance Foyer
- Storage
- Home Gym
- Canal Views
- Complete Electric Power Shutters
Kitchen
- Oven
- Range
- Microwave
- Dishwasher
- Stainless Steel Appliances
- Granite Countertops
- Built-In or Custom Kitchen Cabinets
Flooring
- Carpet
- Marble
- Tile
Bedrooms and Bathrooms
- 8 Bedrooms
- Split Bedroom Floorplan
- Walk-In Closet
- Maid or Guest Quarters
Laundry
- Laundry Room
- Dryer
- Washer
Parking
- 4 Car Garage
- Automatic Garage Door Opener
- Guest Parking
- Open Parking
Pool
- Heated In Ground Pool
- Outdoor Shower
Outdoor Features
- Boat Lift
- Dock made with concrete
- Balcony
- Deck
- Patio
- Outdoor Kitchen
- Lanai
- Exterior Lighting
- Gazebo
- Outdoor Storage
- Tiki or Chickee Hut
- Attached Grill
- Rain Gutters
Additional Homes
- Detached Guest House
Utilities
- Central Heating and Cooling System
- Cooling System Mounted To A Wall/Window
- Propane Stove
- Whole House Permanent Generator
- Propane
- Public Hookup Available For Sewer
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 00140440-000000
Community Details
Overview
- No Home Owners Association
- Key Haven 10Th Add Subdivision
- Rental Restrictions
Amenities
- Lobby
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Listed on
Oct 20, 2025
Closed on
Jan 28, 2026
Sold by
Chapman Anne Marie and Chapman Matthew
Bought by
39 Evergreen Llc
Seller's Agent
The Florida Keys Sold Sisters
Ocean Sotheby's International Realty
Buyer's Agent
Nick Norman
Island Life Realty Experts
List Price
$5,800,000
Sold Price
$5,400,000
Premium/Discount to List
-$400,000
-6.9%
Views
282
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
83.29%
Purchase Details
Listed on
Feb 22, 2020
Closed on
May 26, 2020
Sold by
David M Shield Declaration Of Trust
Bought by
Chapman Anne Marie and Chapman Matthew
Seller's Agent
James Smith
LoKation Real Estate - Pompano Beach
Buyer's Agent
Michael Spirnak
Berkshire Hathaway HomeServices Knight & Gardner Realty
List Price
$7,000,000
Sold Price
$5,600,000
Premium/Discount to List
-$1,400,000
-20%
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Avg. Annual Appreciation
-0.64%
Purchase Details
Closed on
Apr 29, 1998
Sold by
Shield David M and Shield Linda
Bought by
Shield Linda M and Shield David M
Purchase Details
Closed on
Jan 5, 1998
Sold by
Tuzzolo Louis R and Tuzzolo Rose
Bought by
Shield David M and Shield Linda M
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$185,500
Interest Rate
7.2%
Mortgage Type
Balloon
Purchase Details
Closed on
Apr 1, 1985
Bought by
Shield David M Dec Trust 7/7/1997
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Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Warranty Deed | $5,400,000 | Coral Reef Title | |
| Warranty Deed | $5,600,000 | None Listed On Document | |
| Warranty Deed | $100 | -- | |
| Warranty Deed | $265,000 | -- | |
| Warranty Deed | $85,000 | -- |
Source: Public Records
Mortgage History
| Date | Status | Loan Amount | Loan Type |
|---|---|---|---|
| Previous Owner | $957,707 | New Conventional | |
| Previous Owner | $175,000 | New Conventional | |
| Previous Owner | $185,500 | Balloon |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft | Prior Sale |
|---|---|---|---|---|---|
| 01/28/2026 01/28/26 | Sold | $5,400,000 | -6.9% | $817 / Sq Ft | |
| 12/27/2025 12/27/25 | Pending | -- | -- | -- | |
| 10/20/2025 10/20/25 | For Sale | $5,800,000 | +3.6% | $877 / Sq Ft | |
| 05/20/2020 05/20/20 | Sold | $5,600,000 | -20.0% | $923 / Sq Ft | View Prior Sale |
| 05/19/2020 05/19/20 | Pending | -- | -- | -- | |
| 02/22/2020 02/22/20 | For Sale | $7,000,000 | -- | $1,154 / Sq Ft |
Source: Florida Keys Board of REALTORS®
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 |
|---|---|---|---|---|
| 2025 | $51,426 | $5,669,287 | $2,393,366 | $3,275,921 |
| 2024 | $50,041 | $6,078,736 | -- | -- |
| 2023 | $50,041 | $5,901,686 | $2,385,636 | $3,516,050 |
| 2022 | $42,401 | $5,261,770 | $1,767,827 | $3,493,943 |
| 2021 | $39,993 | $4,339,656 | $1,190,957 | $3,148,699 |
| 2020 | $16,457 | $1,782,053 | $0 | $0 |
| 2019 | $16,156 | $1,741,988 | $0 | $0 |
| 2018 | $16,310 | $1,709,508 | $0 | $0 |
| 2017 | $15,842 | $1,674,347 | $0 | $0 |
| 2016 | $15,980 | $1,639,909 | $0 | $0 |
| 2015 | -- | $1,628,509 | $0 | $0 |
| 2014 | -- | $1,615,584 | $0 | $0 |
Source: Public Records
Agents Affiliated with this Home
-
The Florida Keys Sold Sisters
-
Nick Norman
N
Buyer's Agent in 2026
Nick Norman
Island Life Realty Experts
(657) 730-8963
2 Total Sales
-
James Smith
J
Seller's Agent in 2020
James Smith
LoKation Real Estate - Pompano Beach
(786) 296-5248
21 Total Sales
-
D
Seller Co-Listing Agent in 2020
David Shield
LoKation Real Estate
-
M
Buyer's Agent in 2020
Michael Spirnak
Berkshire Hathaway HomeServices Knight & Gardner Realty
Map
Source: Florida Keys Board of REALTORS®
MLS Number: 616954
APN: 00140440-000000
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