37 Cypress Ave, Key West, FL 33040
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Property image
OFF MARKET

37 Cypress Ave
Key West, FL 33040

  • 3 Beds
  • 2 Baths
  • 1,530 sqft

$1,454,100

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $8,345/mo*
Refinance Your Home

$1,454,100

Trulia Estimate
as of Jul 31, 2026
Est. Refi. Payment $8,345/mo*
Refinance Your Home
3 Beds
2 Baths
1,530 sqft

Local Information

  • Map ViewExplore the area around 37 Cypress Ave.
  • Schools1 Preschool School2 Elementary Schools1 Middle School2 High Schools
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1980
Living Area
1,530 sqft
Price/Sqft
$950

About this House

Exclusive Key Haven. Sought after location overlooking Cypress Lake. This 3 bedroom 2 bathroom home offers beautiful sunset views in a quiet neighborhood. Open floor plan and high ceilings. Boat dockage and davits in a deep water canal. Quick access to both the Atlantic and the Gulf, allow for world class fishing and diving.
37 Cypress Ave, Key West, FL 33040 is a 3 bedroom, 2 bathroom, 1,530 sqft single-family home built in 1980. It last sold for $599,000 on May 10, 2011. It is currently off market. The Trulia Estimate is $1,454,100, with a rent estimate of $4,792/month.

Home Details for 37 Cypress Ave

Interior Features

Levels, Entrance, & Accessibility
Stories: 1Floors: Other

Exterior Features

Exterior Home Features
Roof: AsphaltDeckExterior: StuccoFoundation Type: Slab
Parking & Garage
Parking: Carport

Property Information

Year Built
Year Built: 1980Year Updated: 1990
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 6825 sqft

Price History for 37 Cypress Ave

DatePriceEventSource
05/10/2011$599,000Sold
FLKMLS #114272
02/07/2011$639,000Listed For SaleAgent Provided

Market trends in Key West

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$1.23M
$20.83KMoM
Sale-to-List Price
94.6%
0.3%MoM
Price per sq ft
$958
$15MoM
Available listings
288
17MoM
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Property Tax and Assessment

Year2025
Tax$10,502
Assessment$1,327,391
Home facts updated by county records

Comparable Sales for 37 Cypress Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
12 Beechwood Dr, Key West, FL
0.26
Single-Family Home
$900,000
10/16/25
3
2
1,232
16 Bamboo Ter, Key West, FL
0.35
Single-Family Home
$1,475,000
07/15/26
3
2
1,626
3 Birchwood Dr, Key West, FL
0.24
Single-Family Home
$907,500
03/24/26
3
1
1,223
20 Bamboo Ter, Key West, FL
0.35
Single-Family Home
$1,650,000
10/03/25
3
2
1,428
12 Aster Ter, Key West, FL
0.49
Single-Family Home
$1,100,000
08/01/25
3
2
1,280
412 Cactus Dr, Key West, FL
0.22
Single-Family Home
$2,350,000
03/31/26
3
2
2,308
19 Azalea Dr, Key West, FL
0.43
Single-Family Home
$1,800,000
04/17/26
3
2
1,936
117 Key Haven Rd, Key West, FL
0.31
Single-Family Home
$1,850,000
03/10/26
3
2
2,090
8 Floral Ave, Key West, FL
0.32
Single-Family Home
$2,522,000
10/30/25
3
3
2,521
37 Evergreen Ave, Key West, FL
0.28
Single-Family Home
$2,425,000
09/30/25
3
3
2,685

Nearby homes

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Assigned Schools

These are the assigned schools for 37 Cypress Ave.
View nearby schools on GreatSchools
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 267 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Nicholas B.
    "Great place to live; expensive though. Base housing so you give up all your BAH but worth it in this area. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Romero7648
    "Neighbor is downtown and free transportation in immediate vicinity. Many establishments will provide employee discount if you live in the area. "
    0
    Flag
  • Oshry B.
    "open area very friendly neighborhood and neighbors you will love it and your dog would love it even more"
    0
    Flag
  • 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
    Flag

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Explore by feature - Pet Friendly

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Homes for sale near 37 Cypress Ave

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Off Market Homes Near 37 Cypress Ave

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