39 Evergreen Ave, Key West, FL 33040
SOLD
JAN 28, 2026

39 Evergreen Ave
Key West, FL 33040

  • 8 Beds
  • 9.5 Baths
  • 6,611 sqft (on 0.36 acres)

$5,400,000

Last Sold: Jan 28, 2026
7% below list $5.8M
$817/sqft
Est. Refi. Payment $31,014/mo*
Refinance Your Home

$5,400,000

Last Sold: Jan 28, 2026
7% below list $5.8M
$817/sqft
Est. Refi. Payment $31,014/mo*
Refinance Your Home
8 Beds
9.5 Baths
6,611 sqft
(on 0.36 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

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.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from January 28, 2026

Home Highlights

Parking
Attached Garage
Outdoor
Porch, Patio, Deck, Pool
View
Canal
HOA
None
Price/Sqft
$817/sqft
Listed
180+ days ago

Home Details for 39 Evergreen Ave

Interior Features

Interior Details
Wet Bar
Beds & Baths
Number of Bedrooms: 8Number of Bathrooms: 10Number of Bathrooms (full): 9Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6611 Square Feet
Appliances & Utilities
Utilities: FKAA, Propane, Cable Available, Buyer to Verify, Cable ConnectedAppliances: Washer, Stainless Steel Appliance(s), Gas Appliances, Microwave, Oven, Range, Refrigerator, Dishwasher, DryerDishwasherDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Central,Propane Stove,Fireplace(s)Has CoolingAir Conditioning: Central Air,Wall/Window Unit(s)Has HeatingHeating Fuel: Central
Fireplace & Spa
Has a Fireplace
Gas & Electric
Electric: Generator
Windows, Doors, Floors & Walls
Window: Skylight(s), Roll Down ElectricDoor: Glass Doors, Sliding Glass DoorsFlooring: Tile, Marble, Carpet
Levels, Entrance, & Accessibility
Floors: Tile, Marble, Carpet
View
Has a ViewView: Canal

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Lanai, Open Porch/Balcony, Deck, Patio, Roof Top DeckFencing: Privacy, FencedOther Structures: Guest House, Detached Guest Qtrs, Gazebo, Chickee HutExterior: Bar, Storage, Outdoor Shower, Outdoor Kitchen, Lighting, Rain Gutters, Built-in BarbecueHas a Private Pool
Parking & Garage
No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Garage,Trailer Storage,Guest,Open,Garage Door Opener,Attached
Pool
Pool: Heated, In GroundPool
Frontage
WaterfrontWaterfront: Canal Front, Waterfront, Dock: Concrete, Dock Length: 180, Dockage: Boat LiftOn Waterfront
Water & Sewer
Sewer: Municipal Sewer, Public Sewer

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Building: LobbyConstruction Materials: CBS, ICFs (Insulated Concrete Forms), Combo Construction, ConcreteNot a New Construction
Property Information
Condition: Updated/RemodeledParcel Number: 00140440000000

Price & Status

Price
List Price: $5,800,000Price Per Sqft: $817/sqft

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: Key HavenCommunity: Key Haven 10th Add (5.0)

HOA

HOA Fee Includes: NoneAssociation for this Listing: Florida KeysNo HOA

Lot Information

Lot Area: 0.36 acres

Listing Info

Special Conditions: Standard

Offer

Listing Terms: Cash, Conventional

Miscellaneous

Mls Number: 616954Water ViewWater View: Canal
Last check for updates: about 1 hour ago
Listed by Sabrina Wampler & Sarah Ewald, (305) 393-0585
Ocean Sotheby's International Realty
Bought with: Nick Norman, (657) 730-8963, Island Life Realty Experts
Originating MLS: Florida Keys
Source: FLKMLS, MLS#616954

Price History for 39 Evergreen Ave

DatePriceEventSource
01/28/2026$5,400,000Sold
FLKMLS #616954
12/27/2025$5,800,000PendingFLKMLS #616954
12/27/2025$5,800,000PendingToActiveKey West AOR #616954
12/11/2025$5,800,000ContingentKey West AOR #616954
10/20/2025$5,800,000Listed For SaleKey West AOR #616954
07/31/2025$5,799,000ListingRemovedFLKMLS #611707
07/11/2025$5,799,000PriceChange
FLKMLS #611707
03/07/2025$5,999,000PriceChange
FLKMLS #611707
11/12/2024$6,699,000PriceChange
FLKMLS #611707
11/07/2024$6,799,000PriceChange
FLKMLS #611707
10/30/2024$6,899,000PriceChange
FLKMLS #611707
10/03/2024$6,999,000Listed For SaleFLKMLS #611707
08/28/2024$6,999,000ListingRemovedFLKMLS #606778
06/01/2024$6,999,000PriceChange
Key West AOR #606778
04/23/2024$7,699,000PriceChange
Key West AOR #606778
04/13/2024$7,799,000PriceChange
Key West AOR #606778
11/08/2023$7,999,000PriceChange
Key West AOR #606778
09/26/2023$8,199,000Listed For SaleKey West AOR #606778
05/20/2020$5,600,000Sold
FLKMLS #589942
02/22/2020$7,000,000PriceChange
Agent Provided
08/07/2019$6,500,000Listed For SaleAgent Provided
01/05/1998$265,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$49,209
Assessment$5,669,287
Home facts updated by county records

Comparable Sales for 39 Evergreen Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
10 Cypress Ter, Key West, FL
0.16
Single-Family Home
$3,000,000
01/14/26
3
3
3,024
33 Cypress Ave, Key West, FL
0.30
Single-Family Home
$3,250,000
02/12/26
4
4.5
4,102
37 Evergreen Ave, Key West, FL
0.02
Single-Family Home
$2,425,000
09/30/25
3
3
2,685
8 Floral Ave, Key West, FL
0.19
Single-Family Home
$2,522,000
10/30/25
3
3
2,521
117 Key Haven Rd, Key West, FL
0.53
Single-Family Home
$1,850,000
03/10/26
3
2
2,090
30 Allamanda Ave, Key West, FL
0.85
Single-Family Home
$2,500,000
06/24/25
4
3
2,102
26 Bamboo Ter, Key West, FL
0.63
Single-Family Home
$1,925,000
06/19/25
3
3
1,610
30 Key Haven Rd, Key Haven, FL
0.77
Single-Family Home
$1,750,000
12/19/25
3
3
2,715

Assigned Schools

These are the assigned schools for 39 Evergreen Ave.
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The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Key West

At least 266 Trulia users voted on each feature.

  • 88 % Say it's dog friendly

  • 83 % Say people would walk alone at night

  • 77 % Say it's walkable to restaurants

  • 74 % Say there are sidewalks

  • 69 % Say streets are well-lit

  • 69 % Say it's walkable to grocery stores

  • 68 % Say yards are well-kept

  • 65 % Say there's holiday spirit

  • 64 % Say it's quiet

  • 54 % Say parking is easy

  • 52 % Say kids play outside

  • 51 % Say they plan to stay for at least 5 years

  • 49 % Say there's wildlife

  • 46 % Say neighbors are friendly

  • 44 % Say car is needed

  • 44 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Gene Graham
    "I’ve lived in this neighborhood for the past seven years. It is close to the airport and Stock Island."
    0
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  • Ken
    "Walking or bike riding, and extremely bicycle, friendly town! Walking, golf carts, scooters, and bicycles are all very popular here."
    0
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  • David Atkinson
    "I so look forward to getting to Key West. I volunteer at the Tropic and love it. It feels like home."
    0
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  • Trulia User
    "Dogs are welcomed at 90% of the restaurants. Everyone will remember your dogs name but not yours! I love living here with my dog Jack."
    0
    Flag
  • Angela Garcia
    "It’s a small town with little bar life so it would be relatively safe. There is a high school a block away "
    1
    Flag
  • Trulia User
    "Key West is a huge dog community. They even are allowed in some restaurants . When I walk my dog on the main tourist street (Duval St) I get stopped many times from people wanting to pet my dog. A group of dog owners meet up at the park in the morning every day."
    0
    Flag
  • Bawsnack
    "Themed bike rides, parades, fairs, boat races. There is also a bundle of free activities to do when you are a local on first Sunday of every month downtown"
    0
    Flag
  • Sgarvin3281
    " Bikes are all you need small island. Safe and secure. No commute I do t work here it is a vacation community."
    0
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  • Trulia User
    "I ride my bicycle to and from work. It is uneventful but there are natural barriers.t some of the streets are not well lit."
    0
    Flag
  • Trulia User
    "It’s a great neighborhood, we absolutely love having the opportunity to be able to live here!! We don’t have young kids so can’t really express things that are impt for them to know!!"
    1
    Flag
  • Trulia User
    "Everywhere dogs are welcome here in key west, Florida. Come joining us here in key west. Most food and service places, boats, and entertainment venues are good with dogs."
    0
    Flag
  • Trulia User
    "It’s a great community there is tourism so there can be alot of people traffic but for the most part everyone is in good spirits."
    0
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  • Nancy S.
    "So beautiful here everyone calls it paradise! The most relaxing place I have ever been. Welcome to your new Key West Home!(Gieger Key, 10 minutes from Key West downtown) . Make sure you visit all of the wonderful attractions, especially the butterfly garden and don't forget to stop at Gieger Key Marinal for a wonderful meal."
    1
    Flag
  • Trulia User
    "Sunset Carnival and walkability. Beautiful houses and sidewalks. Many houses have gardens and are very well maintained. "
    0
    Flag
  • Trulia User
    "too many festivals to name. There's always something going on Old Town and then come on it's Duvall Street crying out loud mark this would not be a family neighborhood. It's definitely an easy rental"
    0
    Flag
  • Trulia User
    "Feels very safe, super clean, super walkable in old town, and Catholic school looks very vibrant. "
    0
    Flag
  • Trulia User
    "Very beautiful, most people are really nice and cordial. Also very walkable to shops, the marina, and restaurants/bars. But I am just visiting and walking around for a few days."
    0
    Flag
  • Trulia User
    "Great people, great neighborhood, great police, family friendly events. Lots of things to do within a decent drive. Very family friendly generally "
    0
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  • Trulia User
    "I love my neighborhood I have lived here since 1976 and my husband since 1951. Love that it’s easy to get around."
    0
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  • Nicholas B.
    "Great place to live; expensive though. Base housing so you give up all your BAH but worth it in this area. "
    0
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  • Key W. B. F.
    "Gatherings on the local Mangia Mangia bench at 900 Southard street, safe & friendly town. Feel connected & welcomed in Key West. Enjoy the peaceful neighborhood & the tropical weather! You can walk or bike to everything you need & want!"
    0
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  • Mari.lindsley
    "I've lived here for 2 years and enjoy the walkability to local theatres and restaurants. There's a strong homeless contingency that detracts from the seaport. But you can't blame them for wanting to be in paradise."
    11
    Flag
  • Rechele M.
    "Easy compared to city life! 25 minutes max to get from one end of the island to the other in 5 o’clock traffic."
    0
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  • Kfowler
    "I am not currently aware of any neighborhood events that would bring the neighbors closer. However, both my husband and I would be open to any such event that would do so and would improve the neighborhood. The area is beautiful and well maintained, with a few exceptions. "
    2
    Flag
  • Tom
    "There are many festivals and events that include the Key West Historic Harbor. Venues include Schooner Wharf, Waterfront Brewery, The Marker, etc.."
    2
    Flag
  • Hannah B.
    "Vintage Cottage houses, small island feel, Duval Street in a few minutes with hundreds of worldly trendy restaurants "
    6
    Flag
  • Coltonbutler15
    "I grew up in this neighborhood, There have been many upgrades to the neighborhood that have made it more appealing to families with children. "
    12
    Flag
  • MisterE
    "Bicycles, electric golf carts and scooters are the most popular. Although many people still drive cars the island is small so you never have far to go. "
    0
    Flag
  • Caleb G.
    "My neighborhood has the small town vibe mixed with a little party. I love how historic Key West is and how well the history is kept alive. "
    3
    Flag
  • MisterE
    "Great place to raise a family, although we sort of live in a bubble. Kids need to understand how things are in the real world and that’s sometimes difficult to teach. "
    0
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  • Romero7648
    "Neighbor is downtown and free transportation in immediate vicinity. Many establishments will provide employee discount if you live in the area. "
    0
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  • Oshry B.
    "open area very friendly neighborhood and neighbors you will love it and your dog would love it even more"
    0
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  • Bwruble
    "Tourist don’t clean up after their dogs, but locals do. This is a wonderful neighborhood. Gecko lane is especially beautiful and very private. "
    1
    Flag
  • Ctmortman
    "Perfect place for dogs. There are several dog pearls on the island and some restaurants are pet friendly. I own a dog watching business on Marco Island...a service much needed there"
    2
    Flag
  • Carib28
    "Many places to walk your pet and meet people. It’s also very beautiful with hummingbirds and lovely butterflies."
    0
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Homes for sale near 39 Evergreen Ave

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Off Market Homes Near 39 Evergreen Ave

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MLS Internet Data Exchange (IDX) information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that the data is deemed reliable but is not guaranteed accurate by the Florida Keys Board of Realtors.

Homes for rent near 39 Evergreen Ave

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39 Evergreen Ave, Key West, FL 33040 is a 8 bedroom, 10 bathroom, 6,611 sqft single-family home built in 2001. This property is not currently available for sale. 39 Evergreen Ave was last sold on Jan 28, 2026 for $5,400,000 (7% lower than the asking price of $5,800,000). The current Trulia Estimate for 39 Evergreen Ave is $5,350,800.