165 Cutlass Ln

2,448 Sq. Ft.
$449 / Sq. Ft.
2,448
Sq. Ft.
$449
per Sq. Ft.

Description

Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests. Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous kitchen and dining area serve as the heart of the home, ideal for hosting memorable gatherings. Each...Discover Your Dream Waterfront Home in the Florida Keys! This stunning canal-front residence boasts 4 spacious bedrooms and 3 bathrooms. With 2,448 sq. ft. of thoughtfully laid-out living space, this home is perfect for accommodating large families and entertaining guests. Step onto the expansive covered balconies on both floors, where you can relax and take in the serene canal views. The generous kitchen and dining area serve as the heart of the home, ideal for hosting memorable gatherings. Each updated bathroom radiates modern sophistication, while the roomy master suite provides a private sanctuary for relaxation. The exterior of the property offers ample off-street parking and the potential space for a pool--a perfect opportunity for outdoor living. Additionally, a versatile 299 sq. ft. enclosure downstairs provides excellent extra storage for all your needs. Enjoy unparalleled water access to the Gulf and Atlantic, making it easy to indulge in aquatic adventures. With a variety of fantastic restaurants and vibrant bars within walking distance, the lifestyle here is as appealing as the home itself. At an exceptional price of $480 per square foot, this property stands out as one of the best-valued waterfront homes in the Lower Keys. Bring your boat and immerse yourself in the laid-back charm of the Florida Keys--your paradise awaits!

Property Details for 165 Cutlass Lane

Waterfront
Canal Front
Waterfront
Yes
Zoning
IS - Improved Subivision District
Subdivision
Cutthroat Harbor Est (23.0)
Vehicle Storage
Carport, Covered Parking
Pets
Pets Allowed
LISTING UPDATED: 02/16/2026 10:43 AM

Property Details for 165 Cutlass Lane

StatusActive
MLS #616305
Days on Market179
Taxes$5,854 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential / Single Family
Year Built1991
Lot Size0.14 AC / 6,000 SF
CountyMonroe County

Location

Listing Courtesy of Expert Realty LLC (HQ)
Add your commute

Building Information for 165 Cutlass Lane

Stories2Year Built1991Building Size-Lot Size0.14 AC / 6,000 SF

Payment Calculator

$5,844 per month

30 year fixed, 6.15% Interest

Principal and Interest

$5,356

Property Taxes

$488

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 165 Cutlass Lane

Summary
Location and General Information
  • Waterview: Canal View
  • Area: 07 - Cudjoe Key
  • Absolute Longitude: 81.479653
  • Control Depth: 3
  • Listing Board: Key West Association
  • Side: Ocean
  • Mile Marker: 23.0
  • Marathon Neighborhood: N/A
  • Key/Island: Cudjoe Key
Taxes and HOA Information
  • Association Info: Mandatory Home Owners Asc: No
  • Association Info: 1st Right of Refusal: No
  • Fee Includes: None
  • Tax Year: 2024
  • Tax Exemptions: Homestead
Property
Lot Information
  • Lot Size: 60X100
  • Acres: 0.14
  • Land Size: Less Than 1/4 Acre
  • License Info: Non Trans Rntl Lic
Property and Assessments
  • MLS Approved: Y
  • SqFt Source: Property Data Card
  • Flood Zone: AE
  • Rentals Allowed: With Restrictions
  • Deed Restrictions: Unknown
  • Picture Count: 65
  • Document Count: 0
  • Building Style: Above Flood: Yes
Utilities
  • Utilities: FKAA, Municipal Sewer
  • Pub Sewer HkUp: Yes
  • Species List: Yes
  • Pool: No
  • Porch/Balcony: Open Porch/Balcony
Interior and Exterior Features
Interior Features
  • Interior Features: Pantry, Walk-in Closet(s), Storage
  • Appliances: Washer, Range, Refrigerator, Dryer
Exterior Features
  • Roof: Metal Roof
  • Dockage: Dock Length: 50
  • Dockage: Dock: Concrete
  • Dockage: Seawall: Concrete
  • Construction: Frame, Combo Construction
Room Information
  • Specialty Rooms: Laundry Room

Property History for 165 Cutlass Lane

DateEvent & SourcePriceAppreciation
Sep 30, 2025

Listed (Active)

FKMLS #616305

Sep 28, 2025

Backup Contract

FKMLS #616305

Aug 28, 2025

Price Change

FKMLS #616305

$1,175,000
Aug 28, 2025

Listed (Active)

FKMLS #616305

$1,099,000
May 20, 2025

Expired

FKMLS #612352

Nov 20, 2024

Price Change

FKMLS #612352

$1,349,000
Nov 20, 2024

Expired

FKMLS #610089

Nov 20, 2024

Listed (Active)

FKMLS #612352

$1,299,000
May 21, 2024

Price Change

FKMLS #610089

$1,499,000
May 21, 2024

Price Change

FKMLS #610089

$1,449,000
May 21, 2024

Listed (Active)

FKMLS #610089

$1,399,000
Sep 26, 2019

Sold (Public Record)

Public Record #655125206

$724,000

+24.1% / yr

Sep 26, 2019

Sold

FKMLS #581344

$724,000
Aug 25, 2019

Pending

FKMLS #581344

Jul 25, 2018

Listed (Active)

FKMLS #581344

$730,000
Jul 21, 2017

Sold

FKMLS #575352

$442,000
Jun 14, 2017

Sold (Public Record)

Public Record #602222988

$442,000
Jun 9, 2017

Pending

FKMLS #575352

Apr 28, 2017

Listed (Active)

FKMLS #575352

$474,900
Dec 7, 2015

Expired

FKMLS #566040

Dec 10, 2014

Listed (Active)

FKMLS #566040

$450,000
Nov 30, 2013

Expired

FKMLS #556125

Oct 20, 2011

Listed (Active)

FKMLS #556125

$549,000
DateEvent & SourcePrice
09/30/2025

Listed (Active)

FKMLS #616305

09/28/2025

Backup Contract

FKMLS #616305

08/28/2025

Price Change

FKMLS #616305

$1,175,000
08/28/2025

Listed (Active)

FKMLS #616305

$1,099,000
05/20/2025

Expired

FKMLS #612352

11/20/2024

Price Change

FKMLS #612352

$1,349,000
11/20/2024

Expired

FKMLS #610089

11/20/2024

Listed (Active)

FKMLS #612352

$1,299,000
05/21/2024

Price Change

FKMLS #610089

$1,499,000
05/21/2024

Price Change

FKMLS #610089

$1,449,000
05/21/2024

Listed (Active)

FKMLS #610089

$1,399,000
09/26/2019

Sold (Public Record)

Public Record #655125206

$724,000

+24.1% / yr

09/26/2019

Sold

FKMLS #581344

$724,000
08/25/2019

Pending

FKMLS #581344

07/25/2018

Listed (Active)

FKMLS #581344

$730,000
07/21/2017

Sold

FKMLS #575352

$442,000
06/14/2017

Sold (Public Record)

Public Record #602222988

$442,000
06/09/2017

Pending

FKMLS #575352

04/28/2017

Listed (Active)

FKMLS #575352

$474,900
12/07/2015

Expired

FKMLS #566040

12/10/2014

Listed (Active)

FKMLS #566040

$450,000
11/30/2013

Expired

FKMLS #556125

10/20/2011

Listed (Active)

FKMLS #556125

$549,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 165 Cutlass Lane

Taxable ValueLand-Additions-Total-
Tax Record2024$6,087 ($507 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,448 SqFtAbove Grade Finished SqFt2,448 SqFtStories3Lot Size6,000 SqFtStyleSingle Family ResidenceYear Built1991Year Renovated2011CountyMONROEAPN00179960-000000

Schools near 165 Cutlass Lane

This home is within Monroe.
Rating
School
Type
Grades
Distance
Public - PK to 8
Public - 9 to 12
Charter - PK to 5
Charter - 9 to 12
Rating
School
Distance
Sugarloaf School
PublicPK to 8

Key West High School
Public9 to 12

Big Pine Academy
CharterPK to 5

The College Of The Florida Keys Academy
Charter9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

165 Cutlass Lane is a single family home for sale in Cudjoe, FL 33042. This property was listed for sale on August 28, 2025 by Expert Realty LLC (HQ), it's currently listed at $1,099,000. It has been on the market for a total of 179 days and was last sold on September 26, 2019. This listing's school district is Monroe. Nearby schools include Sugarloaf School, Key West High School and Big Pine Academy. 165 Cutlass Lane is a 4-bed, 3-bath, 2,448 sqft single family home built in 1991.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Expert Realty LLC (HQ)

Based on information from one of the following Multiple Listing Services: Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS®. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Beaches Multiple Listing Service, Inc., Martin County REALTORS® of the Treasure Coast, Inc., Miami Association of REALTORS® is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.