29267 Cypress Dr, Big Pine Key, FL 33043
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OFF MARKET

29267 Cypress Dr
Big Pine Key, FL 33043

  • 3 Beds
  • 2 Baths
  • 1,048 sqft

$742,200

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $4,327/mo*

$742,200

Trulia Estimate
as of Jul 22, 2026
Est. Refi. Payment $4,327/mo*
3 Beds
2 Baths
1,048 sqft

Local Information

  • Map ViewExplore the area around 29267 Cypress Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Living Area
1,048 sqft
Price/Sqft
$708

Description

Available now with lease starting October 1st, 2025! Eden Pines single family home - unfurnished two bedroom, two bath with bonus third room which can be used for office or third bedroom. Bring your boat! Concrete dock, boat lift, davits and neighborhood boat ramp with access to bayside and oceanside through Pine Channel. Washer and dryer included. Plenty of off-street parking.

Big Pine Key is conveniently located 30 minutes from both Key West and Marathon. Home is close to shopping, groceries, library, park, restaurants, and more!

6 month lease+ or annual lease options available. Pet friendly with deposit. Tenant pays electric and water. Owner pays trash and cable. Tenant background and credit check required. F/L/S.

Tenants are responsible for utilities, pest, and lawn maintenance. Cable and garbage service provided by the owner. 6-8 month lease or annual lease options available. Pet-friendly with a deposit of $ 1,000 ($250 is non-refundable for cleaning fees). First, last, and security are required for move-in a background and credit check are required.
29267 Cypress Dr, Big Pine Key, FL 33043 is a 3 bedroom, 2 bathroom, 1,048 sqft single-family home. It last sold for $380,000 on Feb 27, 2017 (10,170% above the $3,700 asking price). More recently, it was listed as a rental in September 2025 with an asking price of $3,700 per month. That rental listing was removed on October 8, 2025. It is currently off market. The Trulia Estimate is $742,200, with a rent estimate of $4,472/month.

Home Details for 29267 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
DishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Air ConditioningCooling System: Central Air, Window Unit
Levels, Entrance, & Accessibility
Floors: Tile

Exterior Features

Parking & Garage
Parking: Off Street Parking, On Site

Price History for 29267 Cypress Dr

DatePriceEventSource
10/08/2025$3,700ListingRemovedZillow Rentals
09/26/2025$3,700Listed For RentZillow Rentals
09/10/2025$3,900ListingRemovedZillow Rentals
08/11/2025$3,900PriceChange
Zillow Rentals
07/28/2025$4,200Listed For RentZillow Rentals
06/10/2025$4,400ListingRemovedZillow Rentals
05/16/2025$4,400Listed For RentZillow Rentals
05/09/2025$815,000ListingRemovedFLKMLS #613259
02/05/2025$815,000PriceChange
Key West AOR #613259
01/21/2025$825,000Listed For SaleMLKAR #613259
06/13/2017$399,000ListingRemovedAgent Provided
02/27/2017$380,000Sold
FLKMLS #573395
01/02/2017$399,000Listed For SaleAgent Provided
10/03/1997$158,500Sold
N/A

Market trends in Big Pine Key

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
93
6
MoM
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Property Tax and Assessment

Year2025
Tax$3,822
Assessment$663,722
Home facts updated by county records

Comparable Sales for 29267 Cypress Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.09
Single-Family Home
$755,000
09/22/25
3
2
1,200
0.14
Single-Family Home
$935,000
06/08/26
3
2
1,152
0.24
Single-Family Home
$693,800
07/16/26
3
2
1,039
0.16
Single-Family Home
$887,000
01/27/26
3
2
1,204
0.26
Single-Family Home
$610,000
04/03/26
3
2
1,353
0.11
Single-Family Home
$865,000
04/23/26
2
2
1,092
0.37
Single-Family Home
$600,000
03/03/26
3
2
984
0.18
Single-Family Home
$805,000
05/27/26
2
2
936
0.22
Single-Family Home
$615,000
03/31/26
2
2
1,336
0.26
Single-Family Home
$595,000
09/18/25
2
2
912

Nearby homes

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Assigned Schools

These are the assigned schools for 29267 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."

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Off Market Homes Near 29267 Cypress Dr

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