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Anchor Line Realty

Anchor Line Realty specializes in buyer brokerage, real estate sales listings, and long term property management in Key West & the Florida Keys.

Call: (305) 766-6835

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$5,400,000
39 Evergreen Avenue
Key Haven, FL 33040
MLS# 616954
Status: Closed
8 beds  |  10 baths  |  6611 sqft

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39 Evergreen Ave_1oakstudiosdrone_18
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39 Evergreen Ave_1oakstudiosdrone_18 Relaxing porch areas Sunset vibes Serene outdoor areas Large pool and outdoor areas Swim up bar and custom cabana Bar at custom cabana Protected dockage Outdoor entertaining area Large living pool Dreamy pool with swim up bar Fabulous pool outdoor entertaining area Pool and outdoor entertaining area 39 Evergreen Ave_1oakstudiosdrone_20 Expansive pool home Dockage galore! Expansive estate Driveway and entrace Unique and elegant home Large living area Living room with lots of light Comfortable living areas Open floor plan Dining area Wide open spaces Oversized living room Open floor plan, living area and kitchen Open concept living area and kitchen Guest bathroom Dreamy kitchen Kitchen area Chef's kitchen Kitchen and dining area Primary suite Primary bedroom Large primary suite Primary bathroom Primary bathroom Primary shower Primary bathroom and door to porch Double closets in primary suite Office Guest bedroom Guest bedroom Guest bathroom Guest suite Guest suite living area Guest suite kitchen Guest suite bedroom Guest suite bathroom Guest suite bedroom Guest suite bathroom Guest suite living areas Guest suite bedroom Guest suite bathroom Guest bedroom Gym Dockage for days Dockage Outdoor entertaining area Pretty porches and entertaining areas Covered porches overlooking the pool Stairs to the rooftop deck Lovely outdoor porches Outdoor entertaining area near the canal 39 Evergreen Ave_1oakstudios_70 Front of the home Bird's eye view Outdoor gazebo Shaded and relaxing cabana area Shaded outdoor space Bird's eye view Overlooking the estate and grounds Island vibes Large home with lots of dockage Roof top porch Entering the property Dockage galore! Oversized pool and gazebo 260' of waterfront Dockage and cabana Dockage on the point Large living in Key Haven Dreamy pool and lush landscaping Outdoor of your dreams! Garage for multiple vehicles Oversized garage and storage Garage Oversized garage and storage area Bird's eye view Ariel of property and dockage 1st_floor_39_evergreen_avenue_key_west_w 2nd_floor_39_evergreen_avenue_key_west_w 3rd_floor_39_evergreen_avenue_key_west_w all_floors_39_evergreen_avenue_key_west_

Property 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, 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.

Details
Maps
Contract Information
Current Price: $5,400,000
Listing Date: 2025-10-20
Listing Board: Florida Keys
Leased Price Monthly: $5,400,000
As is Rght to Inspct: Yes
Location, Tax & Legal
Street #: 39
Street Name: Evergreen
Street Suffix: Avenue
Key/Island: Key Haven
State/Province: FL
Zip Code: 33040
County: Monroe
Subdivision: Key Haven 10th Add (5.0)
Area: 05 - Stock Island to Shark Key
General Property Description
Realtor.COM Type: Residential - Single Family
Style: Single Family
Waterfront: Yes
Control Depth: 4
Pool: Yes
Year Built: 2001
Lot SqFt: 15687
Lot Sqft Source: Property Data Card
Acres: 0.36
Living Apx SqFt: 6611
SqFt Source: Tax Records
Total Bedrooms: 8
Full Baths: 9
Half Baths: 1
Total Baths: 10
Rentals Allowed: With Restrictions
Status Change Info
Under Contract Date: 2025-12-27
Leased Date: 2026-01-28
Leased Price Monthly: $5,400,000
Sold Comments: furnishings included
Status: Closed
Association Info
Mandatory Home Owners Asc: No
1st Right of Refusal: No
Dockage
Dock Length: 180
Dock: Concrete
Specialty Rooms
Guest/Servant Qtrs: Legal
Building Style
Above Flood: Unknown
Vehicle Storage
Car(s): 4+
Pool Info
Heated: Yes
Financial Status
Standard Sale: Yes
Property Features
Fee Includes: None
Tax Exemptions: None
Waterfront: Canal Front
Waterview: Canal View
Dockage: Boat Lift
Property Condition: Updated/Remodeled
Vehicle Storage: Garage; Attached; Auto Door Opener; Guest Parking; Open Parking; Trailer Storage
Furnished: Negotiable
Cooling: Central Air; Wall/Window Unit(s)
Heating: Central; Fireplace(s); Propane Stove
Utilities: Buyer to Verify; Cable Available; FKAA; Municipal Sewer; Propane; Whole House Generatr
Interior Features: Bar; Built-in Cabinets; Cathedral Ceilings; Entrance Foyer; Fireplace(s); Granite Counter Top; Lobby; Sky Light(s); Split Bedroom; Storage; Tray Ceilings; Walk-in Closet(s); Wet Bar
Pre-Wired: Cable
Specialty Rooms: Gym; Laundry Room
Appliances: Dishwasher; Dryer; Gas Appliances; Microwave; Oven; Range; Refrigerator; Stainless Steel Appliance(s); Washer
Exterior Features: Bar; Built-in Grill; Chickee Hut; Detached Guest Qtrs; Fencing; Gazebo; Lanai; Lighting; Outdoor Kitchen; Outdoor Shower; Privacy Wall/Fence; Rain Gutters; Storage
Pool Info: In Ground
Construction: CBS; Combo Construction; Concrete; ICFs (Insulated Concrete Forms)
Shutters: Roll Down Electric
Floor: Carpet; Marble; Tile
Roof: Metal Roof
Pets: Pets Allowed
Land Size: 1/4 - 1/2 Acre
Terms: Cash; Conventional
Title: Negotiable

Listing Office: Ocean Sotheby's International Realty

Last Updated: January - 28 - 2026

The data relating to real estate for sale on this web site comes in part from the Florida Keys MLS, Inc. Information provided is deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. The information being provided is for consumers’ personal, non-commeral use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. IDX data is deemed reliable but is not guaranteed accurate by the MLS.


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David Austin, Owner/Broker
Anchor Line Realty, LLC
820 Ashe Street
Key West, FL 33040
www.anchorlinerealty.com
[email protected]
305.766.6835
Member, National Association of Realtors (NAR)
Member, Florida Association of Realtors (FAR)
Member, Key West Association of Realtors (KWAR)