29255 Cypress Dr
Big Pine Key, FL 33043
- 2 Beds
- 2.5 Baths
- 1,250 sqft
2 Beds
2.5 Baths
1,250 sqft
Local Information
-- mins to
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.
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
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Property Type / Style Property Type: Single Family Home |
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Lease Term: 1 YearAvailable: now |
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Appliances & Utilities DishwasherDryerWasher |
Heating & Cooling Air ConditioningCooling System: Central Air |
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Parking & Garage Parking: Off Street Parking, On Site |
Price History for 29255 Cypress Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 07/18/2025 | $3,900 | ListingRemoved | Zillow Rentals |
| 06/23/2025 | $3,900 | PriceChange | Zillow Rentals |
| 06/13/2025 | $4,000 | Listed For Rent | Zillow Rentals |
| 09/13/2024 | $3,850 | ListingRemoved | Zillow Rentals |
| 06/20/2024 | $3,850 | PriceChange | Zillow Rentals |
| 06/06/2024 | $4,000 | PriceChange | Zillow Rentals |
| 04/24/2024 | $4,100 | PriceChange | Zillow Rentals |
| 03/18/2024 | $4,200 | PriceChange | Zillow Rentals |
| 03/05/2024 | $4,300 | PriceChange | Zillow Rentals |
| 02/24/2024 | $4,400 | Listed For Rent | Zillow Rentals |
| 06/30/2023 | ListingRemoved | Zillow Rentals | |
| 06/06/2023 | $3,950 | Listed For Rent | Zillow Rentals |
| 08/25/2021 | ListingRemoved | Zillow Rental Manager | |
| 08/07/2021 | $3,250 | Listed For Rent | Zillow Rental Manager |
| 02/25/2021 | ListingRemoved | N/A | |
| 09/21/2020 | $2,800 | ListingRemoved | N/A |
| 08/09/2020 | $2,800 | PriceChange | N/A |
| 07/23/2020 | $2,995 | Listed For Rent | N/A |
| 08/03/2019 | $2,800 | ListingRemoved | Agent Provided |
| 06/25/2019 | $2,800 | Listed For Rent | Agent Provided |
| 03/07/2019 | $426,000 | Sold | FLKMLS #583554 |
| 01/07/2019 | $425,000 | Listed For Sale | Agent Provided |
| 03/18/2002 | $240,000 | Sold | FLKMLS #510818 |
| 01/17/2001 | $200,000 | Sold | N/A |
Market trends in Big Pine Key
Last updated May 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
99
1MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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.Assigned Schools
These are the assigned schools for 29255 Cypress Dr.
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.
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