Discover your dream waterfront retreat in the Florida Keys. This canal-front home features 4 spacious bedrooms and 3 bathrooms with 2,448 sq. ft. of thoughtfully designed living space, perfect for accommodating family, guests, and entertaining. Enjoy expansive covered balconies on both levels, where you can relax and take in peaceful canal views and the laid-back island lifestyle. The generous kitchen and dining area serve as the heart of the home--ideal for hosting gatherings after a day on the water. Updated bathrooms offer a modern feel, while the spacious primary suite provides a private sanctuary to unwind. Outside, the property offers ample off-street parking and room to add a pool, creating the perfect setting for outdoor living. A versatile 299 sq. ft. downstairs enclosure adds valuable storage space for fishing gear, water toys, and more. With direct boating access to both the Gulf and the Atlantic, adventure is always within reach. Plus, local restaurants, marinas, and island bars are just a short walk away, letting you enjoy the best of the Keys lifestyle. At just $439 per square foot, this property represents the lowest price per square foot for a waterfront home currently available in the Florida Keys, making it one of the best opportunities on the market today. Bring your boat and start living the Florida Keys dream.
For sale
$1,075,000
165 Cutlass Ln, Cudjoe Key, FL 33042
4beds
2,448sqft
Est.:
Single Family Residence
Built in 1991
6,098.4 Square Feet Lot
$1,491,300 Zestimate®
$439/sqft
$-- HOA
What's special
Ample off-street parkingCanal-front homePeaceful canal viewsUpdated bathrooms
- 34 days |
- 1,796 |
- 83 |
Zillow last checked:
Listing updated:
Listed by:
Justyn Ewald 305-587-7330,
Expert Realty LLC (HQ),
Mason C Kelly 631-603-6123,
Expert Realty LLC (HQ)
Source: FLKMLS,MLS#: 619003
Originating MLS: Key West Association
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 3
- Full bathrooms: 3
Cooling
- Central Air, Ceiling Fans(s)
Appliances
- Included: Washer, Range, Refrigerator, Dryer
- Laundry: Laundry Room
Features
- Pantry, Walk-In Closet(s), Storage
Interior area
- Total interior livable area: 2,448 sqft
Property
Parking
- Parking features: Carport, Covered
- Has carport: Yes
Features
- Levels: Two
- Stories: 2
- Patio & porch: Open Porch/Balcony
- Has view: Yes
- View description: Canal
- Has water view: Yes
- Water view: Canal
- Waterfront features: Canal Front, Waterfront, Seawall: Concrete, Dock: Concrete, Dock Length: 50
Lot
- Size: 6,098.4 Square Feet
- Features: Less Than 1/4 Acre
Details
- Parcel number: 00179960000000
- Zoning: IS
- Zoning description: Improved Subivision District
Construction
Type & style
- Home type: SingleFamily
- Property subtype: Single Family Residence
Materials
- Frame, Combo Construction
- Roof: Metal
Condition
- Year built: 1991
Utilities & green energy
- Sewer: Municipal Sewer, Public Sewer
- Utilities for property: FKAA
Community & HOA
Community
- Subdivision: Cutthroat Harbor Est (23.0)
HOA
- Has HOA: No
- Services included: None
Location
- Region: Cudjoe Key
Financial & listing details
- Price per square foot: $439/sqft
- Tax assessed value: $1,005,888
- Annual tax amount: $6,411
- Date on market: 3/10/2026
- Listing terms: Cash,FHA,VA Loan,Conventional
Estimated market value
$1,491,300
$1.42M - $1.57M
$7,951/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 3/10/2026 | Listed for sale | $1,075,000-2.2%$439/sqft |
Source: | ||
| 3/1/2026 | Listing removed | $1,099,000$449/sqft |
Source: | ||
| 10/17/2025 | Price change | $1,099,000-6.5%$449/sqft |
Source: | ||
| 10/1/2025 | Listed for sale | $1,175,000$480/sqft |
Source: | ||
| 9/28/2025 | Contingent | $1,175,000$480/sqft |
Source: | ||
| 8/28/2025 | Listed for sale | $1,175,000-9.5%$480/sqft |
Source: | ||
| 5/21/2025 | Listing removed | $1,299,000$531/sqft |
Source: | ||
| 2/25/2025 | Price change | $1,299,000-3.7%$531/sqft |
Source: | ||
| 11/21/2024 | Listed for sale | $1,349,000-3.6%$551/sqft |
Source: | ||
| 9/2/2024 | Listing removed | $1,399,000$571/sqft |
Source: | ||
| 7/18/2024 | Price change | $1,399,000-3.5%$571/sqft |
Source: | ||
| 6/24/2024 | Price change | $1,449,000-3.3%$592/sqft |
Source: | ||
| 5/21/2024 | Listed for sale | $1,499,000+107%$612/sqft |
Source: | ||
| 9/26/2019 | Sold | $724,000-0.8%$296/sqft |
Source: | ||
| 7/23/2019 | Price change | $730,000-0.7%$298/sqft |
Source: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys #581344 Report a problem | ||
| 7/3/2019 | Price change | $735,000-0.5%$300/sqft |
Source: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys #581344 Report a problem | ||
| 6/21/2019 | Price change | $739,000-0.7%$302/sqft |
Source: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys #581344 Report a problem | ||
| 6/1/2019 | Price change | $744,000-0.7%$304/sqft |
Source: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys #581344 Report a problem | ||
| 2/22/2019 | Price change | $749,000-3.9%$306/sqft |
Source: Berkshire Hathaway HomeServices Keys Real Estate - Lower Keys #581344 Report a problem | ||
| 1/3/2019 | Price change | $779,000-2.5%$318/sqft |
Source: Marathon & Lower Keys Association of Realtors #581344 Report a problem | ||
| 8/3/2018 | Listed for sale | $799,000+80.8%$326/sqft |
Source: American Caribbean Real Estate-Lower Keys #581344 Report a problem | ||
| 7/21/2017 | Sold | $442,000-6.9%$181/sqft |
Source: | ||
| 4/29/2017 | Listed for sale | $474,900+5.5%$194/sqft |
Source: Century 21 Schwartz Realty (ISL) #575352 Report a problem | ||
| 12/8/2015 | Listing removed | $450,000$184/sqft |
Source: Coldwell Banker Schmitt RE Co. Lower Keys Office #566040 Report a problem | ||
| 2/24/2015 | Listed for sale | $450,000$184/sqft |
Source: Coldwell Banker Schmitt Real Estate Co. #566040 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,411 +5.3% | $682,064 +2.9% |
| 2024 | $6,087 +4% | $662,842 +3% |
| 2023 | $5,854 +2.7% | $643,536 +3% |
| 2022 | $5,700 -3% | $624,793 +3% |
| 2021 | $5,874 -0.3% | $606,596 +0.5% |
| 2020 | $5,894 | $603,300 +14.6% |
| 2019 | $5,894 +5.6% | $526,274 +3.6% |
| 2018 | $5,579 +0.7% | $507,879 +3.6% |
| 2017 | $5,542 +4% | $490,400 +77.6% |
| 2016 | $5,329 +79.1% | $276,051 +0.7% |
| 2015 | $2,975 | $274,132 |
Find assessor info on the county website
Monthly payment
Est. payment
$5,893/mo
Principal & interest
$5158
Property taxes
$735
More affordability tools
Climate risks
Neighborhood: 33042
Nearby schools
GreatSchools rating
- 5/10Sugarloaf SchoolGrades: PK-8Distance: 3.2 mi
- 3/10Key West High SchoolGrades: 9-12Distance: 20.1 mi
A local agent can set up tours, give advice and negotiate with sellers.
A local lender can help you make sure your offer is ready when you are.
- Florida
- Monroe County
- Summerland Key
- 33042
- 165 Cutlass Ln





