29255 Cypress Dr, Big Pine Key, FL 33043
OFF MARKET

29255 Cypress Dr
Big Pine Key, FL 33043

  • 2 Beds
  • 2.5 Baths
  • 1,250 sqft

$722,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,106/mo*

$722,000

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $4,106/mo*
2 Beds
2.5 Baths
1,250 sqft

Local Information

  • Map ViewExplore the area around 29255 Cypress Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Very nice, unfurnished canal front 2.5/2+bdrm stilt home in desirable Eden Pines, Big Pine Key.
50' of bulkhead with 10,000 lb lift davits on canal with 10' wide 30' long side slip. 12 or 6 month minimum lease desired. Open lots across canal and one side for added privacy. Home includes new appliances, new dishwasher, new washer/dryer, central heat and A/C, newly installed porcelain tile flooring throughout (some pictures show previous flooring), new ceiling fan installed on balcony. Metal roof installed 2016. Fish right off the bulkhead and enjoy the manatees that visit regularly! There is a boat davit available for use by tenant over canal, as well as a fish cleaning station. Neighborhood boat launch. Covered carport with 12' x 12' enclosed, lockable storage for tenant use. Additional bonus room available. Property fenced. Very low maintenance yard. Nice neighborhood. First, last, and deposit required. Small pet ok with approval from landlord. No smoking on premises. Available June 15 2025 Please respond to ad with any questions!

Garbage included two days a week (must be kept secure inside fence except on garbage day, due to Key deer in area). Tenant responsible for all other utilities, water, sewer, etc.. Owner has 5th wheel trailer parked stored on property.
29255 Cypress Dr, Big Pine Key, FL 33043 is a 2 bedroom, 3 bathroom, 1,250 sqft single-family home. It last sold for $426,000 on Mar 7, 2019 (10,823% above the $3,900 asking price). More recently, it was listed as a rental in June 2025 with an asking price of $4,000 per month. That rental listing was removed on July 18, 2025. It is currently off market. The Trulia Estimate is $722,000, with a rent estimate of $4,087/month.

Home Highlights

Parking
No Info
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 29255 Cypress Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 YearAvailable: now

Interior Features

Appliances & Utilities
DishwasherDryerWasher
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price History for 29255 Cypress Dr

DatePriceEventSource
07/18/2025$3,900ListingRemovedZillow Rentals
06/23/2025$3,900PriceChange
Zillow Rentals
06/13/2025$4,000Listed For RentZillow Rentals
09/13/2024$3,850ListingRemovedZillow Rentals
06/20/2024$3,850PriceChange
Zillow Rentals
06/06/2024$4,000PriceChange
Zillow Rentals
04/24/2024$4,100PriceChange
Zillow Rentals
03/18/2024$4,200PriceChange
Zillow Rentals
03/05/2024$4,300PriceChange
Zillow Rentals
02/24/2024$4,400Listed For RentZillow Rentals
06/30/2023ListingRemovedZillow Rentals
06/06/2023$3,950Listed For RentZillow Rentals
08/25/2021ListingRemovedZillow Rental Manager
08/07/2021$3,250Listed For RentZillow Rental Manager
02/25/2021ListingRemovedN/A
09/21/2020$2,800ListingRemovedN/A
08/09/2020$2,800PriceChange
N/A
07/23/2020$2,995Listed For RentN/A
08/03/2019$2,800ListingRemovedAgent Provided
06/25/2019$2,800Listed For RentAgent Provided
03/07/2019$426,000Sold
FLKMLS #583554
01/07/2019$425,000Listed For SaleAgent Provided
03/18/2002$240,000Sold
FLKMLS #510818
01/17/2001$200,000Sold
N/A

Market trends in Big Pine Key

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
99
1
MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$5,669
Assessment$651,781
Home facts updated by county records

Comparable Sales for 29255 Cypress Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.21
Single-Family Home
$615,000
03/31/26
2
2
1,336
0.13
Single-Family Home
$865,000
04/23/26
2
2
1,092
0.09
Single-Family Home
$755,000
09/22/25
3
2
1,200
0.26
Single-Family Home
$595,000
09/18/25
2
2
912
0.18
Single-Family Home
$805,000
05/27/26
2
2
936
0.20
Single-Family Home
$880,000
10/15/25
2
2
1,056
0.18
Single-Family Home
$500,000
08/19/25
2
1
1,020
0.13
Single-Family Home
$935,000
06/08/26
3
2
1,152
0.25
Single-Family Home
$610,000
04/03/26
3
2
1,353
0.17
Single-Family Home
$887,000
01/27/26
3
2
1,204

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 29255 Cypress Dr.
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 Big Pine Key

At least 29 Trulia users voted on each feature.
  • 95 % Say it's dog friendly

  • 91 % Say there's wildlife

  • 82 % Say car is needed

  • 82 % Say yards are well-kept

  • 81 % Say parking is easy

  • 76 % Say people would walk alone at night

  • 75 % Say it's quiet

  • 66 % Say there's holiday spirit

  • 62 % Say it's walkable to grocery stores

  • 59 % Say it's walkable to restaurants

  • 55 % Say they plan to stay for at least 5 years

  • 52 % Say neighbors are friendly

  • 43 % Say there are community events

  • 35 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Dawn M.
    "I live in Big Pine Key! Neighbors are friendly but keep to themselves. Lots of wildlife . Pretty safe place. "
  • Dawn M.
    "I do not believe there are community events! If there are I have not gone to any! I love Key Deer Blvd good place to run, walk or jog. Also bike riders there are tons! "
  • Sailjane
    "Yes, they would love the area. No restrictions for size, amount, breed, etc. yards are large so pets have room. There is a dog park down the road, excellent vets, many restaurants are dog friendly. There are pet parades, etc too"
  • Sailjane
    "Great parks, great schools, people are very kind and friendly. The scenery is gorgeous. Key deer, peacocks, cool birds, are all around. This is a great place to vacation to and to live. Water all around and the fishing is spectacular. It is a artistic community and very interesting. "
  • Karen F.
    "We have a nautical flea market as well as a weekend flea market, the wildlife refuge has events and there are various events at the park"
  • Shannon M.
    "friendly neighborhood with lots of wildlife both in the water and on land. nice and quiet and away from the craziness of key West but close enough to visit. nowhere else will you see an endangered key deer in your yard on the same day you have. manatee in your back canal. simply beautiful ❤️"
  • Gwalter
    "A great place to live, fish, hang out and enjoy your friends !! It’s well worth a visit. Come as you are and leave as friends "
  • Chelsea G.
    "Born and raised here in Big Pine. Low crime rate. Small property lots. I like it here because there is a grocery store and a a couple gas stations for easy accessibility. "
  • Katherine V.
    "Home to US Fish and Wildlife nature sanctuary, with star-filled nights and sunny, breezy days year-round. Caring community with good basic services. Bike paths, incredible boating and diving. "
  • Maya T.
    "Quiet area for peace and nature lovers."

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

Explore by feature - Pool

Explore by feature - Washer/dryer

Homes for sale near 29255 Cypress Dr

Skip to last item
Skip to first item

Off Market Homes Near 29255 Cypress Dr

Skip to last item
Skip to first item