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.
Sold for $5,400,000
Street View
$5,400,000
39 Evergreen Ave, Key West, FL 33040
8beds
6,611sqft
Single Family Residence
Built in 2001
0.36 Acres Lot
$5,413,000 Zestimate®
$817/sqft
$7,958 Estimated rent
Home value
$5,413,000
$4.71M - $6.17M
$7,958/mo
Zestimate® history
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List your homeWhat's special
Waterfront estateThree fireplacesCascading waterfallsHeated glass-mosaic poolExclusive key haven cul-de-sacCustom cabanaRefined living space
Zillow last checked:
Listing updated:
Listed by:
Sabrina Wampler & Sarah Ewald 305-393-0585,
Ocean Sotheby's International Realty
Bought with:
Nick Norman, 3644313
Island Life Realty Experts
Source: FLKMLS,MLS#: 616954
Originating MLS: Florida Keys
Originating MLS: Florida KeysFacts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 8
- Bathrooms: 10
- Full bathrooms: 9
- 1/2 bathrooms: 1
Heating
- Central, Propane Stove, Fireplace(s)
Cooling
- Central Air, Wall/Window Unit(s)
Appliances
- Included: Washer, Stainless Steel Appliance(s), Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
- Laundry: Laundry Room
Features
- Wet Bar, Built-in Cabinets, Tray Ceiling(s), Bar, Walk-In Closet(s), Storage, Granite Counters, Entrance Foyer, Fireplace(s), Split Bedroom, Cathedral Ceiling(s), Gym
- Flooring: Tile, Marble, Carpet
- Doors: Glass Doors, Sliding Glass Doors
- Windows: Skylight(s), Roll Down Electric
- Has fireplace: Yes
Interior area
- Total interior livable area: 6,611 sqft
Property
Parking
- Total spaces: 4
- Parking features: Garage, Trailer Storage, Guest, Open, Garage Door Opener, Attached
- Has attached garage: Yes
- Has uncovered spaces: Yes
Features
- Patio & porch: Lanai, Open Porch/Balcony, Deck, Patio, Roof Top Deck
- Exterior features: Bar, Storage, Outdoor Shower, Outdoor Kitchen, Lighting, Rain Gutters, Built-in Barbecue
- Has private pool: Yes
- Pool features: Heated, In Ground
- Fencing: Privacy,Fenced
- Has view: Yes
- View description: Canal
- Has water view: Yes
- Water view: Canal
- Waterfront features: Canal Front, Waterfront, Dock: Concrete, Dock Length: 180, Dockage: Boat Lift
Lot
- Size: 0.36 Acres
- Features: 1/4 - 1/2 Acre
Details
- Additional structures: Guest House, Detached Guest Qtrs, Gazebo, Chickee Hut
- Parcel number: 00140440000000
- Zoning: IS
- Zoning description: Improved Subivision District
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- CBS, ICFs (Insulated Concrete Forms), Combo Construction, Concrete
- Roof: Metal
Condition
- Updated/Remodeled
- New construction: No
- Year built: 2001
Utilities & green energy
- Electric: Generator
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA, Propane, Cable Available, Buyer to Verify, Cable Connected
Community & neighborhood
Location
- Region: Key West
- Subdivision: Key Haven 10th Add (5.0)
HOA & financial
HOA
- Has HOA: No
- Services included: None
Other
Other facts
- Listing terms: Cash,Conventional
Price history
| Date | Event | Price |
|---|---|---|
| 1/28/2026 | Sold | $5,400,000-6.9%$817/sqft |
Source:  FLKMLS #616954 Report a problem | ||
| 12/27/2025 | Pending sale | $5,800,000$877/sqft |
Source: FLKMLS #616954 Report a problem | ||
| 12/27/2025 | Listed for sale | $5,800,000$877/sqft |
Source:  Key West AOR #616954 Report a problem | ||
| 12/11/2025 | Contingent | $5,800,000$877/sqft |
Source: Key West AOR #616954 Report a problem | ||
| 10/20/2025 | Listed for sale | $5,800,000+0%$877/sqft |
Source: Key West AOR #616954 Report a problem | ||
| 7/31/2025 | Listing removed | $5,799,000$877/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 7/11/2025 | Price change | $5,799,000-3.3%$877/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 3/7/2025 | Price change | $5,999,000-10.4%$907/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 11/12/2024 | Price change | $6,699,000-1.5%$1,013/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 11/7/2024 | Price change | $6,799,000-1.4%$1,028/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 10/30/2024 | Price change | $6,899,000-1.4%$1,044/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 10/3/2024 | Listed for sale | $6,999,000$1,059/sqft |
Source: FLKMLS #611707 Report a problem | ||
| 8/28/2024 | Listing removed | $6,999,000$1,059/sqft |
Source: FLKMLS #606778 Report a problem | ||
| 6/1/2024 | Price change | $6,999,000-9.1%$1,059/sqft |
Source: Key West AOR #606778 Report a problem | ||
| 4/23/2024 | Price change | $7,699,000-1.3%$1,165/sqft |
Source: Key West AOR #606778 Report a problem | ||
| 4/13/2024 | Price change | $7,799,000-2.5%$1,180/sqft |
Source: Key West AOR #606778 Report a problem | ||
| 11/8/2023 | Price change | $7,999,000-2.4%$1,210/sqft |
Source: Key West AOR #606778 Report a problem | ||
| 9/26/2023 | Listed for sale | $8,199,000+46.4%$1,240/sqft |
Source: Key West AOR #606778 Report a problem | ||
| 5/20/2020 | Sold | $5,600,000-20%$847/sqft |
Source: FLKMLS #589942 Report a problem | ||
| 2/22/2020 | Price change | $7,000,000+7.7%$1,059/sqft |
Source: LoKation Real Estate #589942 Report a problem | ||
| 8/7/2019 | Listed for sale | $6,500,000+2352.8%$983/sqft |
Source: Lokation Real Estate #586855 Report a problem | ||
| 1/5/1998 | Sold | $265,000$40/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $49,209 -4.3% | $5,669,287 -6.7% |
| 2024 | $51,426 +2.8% | $6,078,736 +3% |
| 2023 | $50,041 +18% | $5,901,686 +23.6% |
| 2022 | $42,401 +6% | $4,773,622 +10% |
| 2021 | $39,993 +143% | $4,339,656 +143.5% |
| 2020 | $16,457 | $1,782,053 +2.3% |
| 2019 | $16,457 +1.9% | $1,741,988 +1.9% |
| 2018 | $16,156 -0.9% | $1,709,508 +2.1% |
| 2017 | $16,310 | $1,674,347 +2.1% |
| 2016 | -- | $1,639,909 +0.7% |
| 2015 | -- | $1,628,509 |
Find assessor info on the county website
Neighborhood: 33040
Nearby schools
GreatSchools rating
- 4/10Gerald Adams Elementary SchoolGrades: PK-5Distance: 0.6 mi
- NAAdult/Vocational/Community EducationGrades: Distance: 0.6 mi
- 4/10Key West High SchoolGrades: 9-12Distance: 3.3 mi
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Estimated market value
$5,413,000
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Estimated market value
$5,413,000
- Florida
- Monroe County
- Key West
- 33040
- 39 Evergreen Ave
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