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$5,400,000

  • Sold
  • Closed
  • Single Family
  • 8 Beds
  • 9 Full Baths
  • 1 Partial Bath
  • 6,611 Sq. Ft.
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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.

Full Property Details for 39 Evergreen Ave

General

  • Sold For: $5,400,000
  • Taxes: $51,426 (2024)
  • Status: Closed
  • Type: Single Family
  • Source: 927
  • MLS ID: 616954
  • Added to Site: 132 day(s) ago

Interior

  • Rooms/Areas: Gym, Laundry Room
  • 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
  • Fireplace: Yes
  • Appliances: Washer, Stainless Steel Appliance(s), Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, Dryer
  • Furnishings: Negotiable
  • Flooring: Tile, Marble, Carpet

Rooms

Bathrooms

  • Total Bathrooms: 10
  • Full Bathrooms: 9
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 8

Additional Information

  • Pool: Yes
  • Pool Description: In Ground

Exterior

  • 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
  • Deck/Patio: Open Porch/Balcony, Deck, Patio, Roof Top Deck

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Parking: Garage, Trailer Storage, Guest Parking, Open Parking, Auto Door Opener, Attached

Location

  • Area: 05 - Stock Island to Shark Key
  • County: Monroe
  • Subdivision: Key Haven 10th Add (5.0)
  • Driving Directions: GPS

Community

  • Assoc. Fees Include: None
  • Pets Allowed: Yes

Heating & Cooling

  • Cooling Type: Central Air, Wall/Window Unit(s)
  • Heating Type: Central, Propane Stove, Fireplace(s)

Utilities

  • Water: Canal View
  • Utility Description: FKAA, Propane, Cable Available, Whole House Generatr, Buyer to Verify, Municipal Sewer

Structural Information

  • Architectural Style: Single Family
  • Construction Status: Updated/Remodeled
  • Construction: CBS, ICFs (Insulated Concrete Forms), Combo Construction, Concrete
  • Roof: Metal Roof
  • Windows/Doors: Glass Doors, Sliding Glass Doors
  • Dock Size: 180
  • Wiring: Cable
  • Square Feet: 6,611
  • Sq. Ft. Source: Tax Records
  • Year Built: 2001
  • Property Condition: Updated/Remodeled

Lot Features

  • Lot Size (Sq. Ft.): 15,687
  • Fence: Yes
  • Zoning: IS - Improved Subivision District

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Type: Canal Front
  • Dock Description: Boat Lift

Financial Considerations

  • Tax Amount: $51,426
  • Tax Year: 2024
  • Terms: Cash, Conventional

Disclosures and Reports

  • Legal Description: 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
  • Flood Zone: AE
  • APN: 00140440-000000

Listed by Ocean Sotheby's International Realty, Sabrina Wampler & Sarah Ewald (305) 393-0585
Sold by Island Life Realty Experts, Nick Norman

Listing agent

— 39 Evergreen Ave —

  • Sabrina Wampler & Sarah Ewald

    Ocean Sotheby's International Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39 Evergreen Ave

School District:Monroe County School District, Middle Torch Key, FL
NameGradesDistance
Gerald Adams Elementary School
5855 College Road, Key West, FL 33040
PK-50.7 mi
Key West High School
2100 Flagler Avenue, Key West, FL 33040
9-123.3 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39 Evergreen Ave

Date
Details
Price
Change
Source
1/28/2026
Sold
$5,400,000
-6.9%
MLS
10/20/2025
Listed
$5,800,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Ocean Sotheby's International Realty, Sabrina Wampler & Sarah Ewald (305) 393-0585
Sold by Island Life Realty Experts, Nick Norman

39 Evergreen Avenue, Key Haven, FL 33040 (MLS# 616954) is a Single Family property that was sold at $5,400,000 on January 28, 2026. Want to learn more about 39 Evergreen Avenue? Do you have questions about finding other Single Family real estate for sale in Key Haven? You can browse all Key Haven real estate or contact a Coldwell Banker agent to request more information.