4305 Cutlass Ln, Naples, FL 34102
Property image
Property image
OFF MARKET

$22,733,500

Trulia Estimate
  • 4 Beds
  • 7 Baths
  • 6,314 sqft (on 0.94 acres)

4305 Cutlass Ln, Naples, FL 34102

Port Royal
Est. Refi. Payment $139,326/mo*
Refinance Your Home
Currently Off Market - Sold Sep 1, 2021 for $16,000,000

Home Value

Trulia Estimate
$22.7M
Since last month
Decreased$278K (-1.2%)
Since last year
Increased$5M (+25.9%)
Since last sale
Increased$7M (+42.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +124% in the last 10 years
MonthEstimated value
2026
September 2026$22.73M
August 2026$23.01M
July 2026$22.3M
June 2026$22.99M
May 2026$21.1M
April 2026$17.6M
March 2026$17.84M
February 2026$18.51M
January 2026$17.05M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
4115 Cutlass LN, Naples, FL
0.18
Single-Family Home
$25,000,000
02/25/26
6
7
6,291
3580 Gin LN, Naples, FL
0.54
Single-Family Home
$15,900,000
05/11/26
5
5.5
6,816
860 Admiralty Parade E, Naples, FL
0.38
Single-Family Home
$40,000,000
04/13/26
5
6
11,559
3777 Gordon DR, Naples, FL
0.44
Single-Family Home
$36,500,000
07/22/26
6
7
9,074
14 Sabre LN, Naples, FL
0.29
Single-Family Home
$10,950,000
07/29/26
4
4.5
5,416
3455 Gin LN, Naples, FL
0.70
Single-Family Home
$13,000,000
03/16/26
6
7.5
8,044
3440 RUM ROW, Naples, FL
0.70
Single-Family Home
$28,250,000
04/21/26
5
7
7,835
3525 Rum Row, Naples, FL
0.70
Single-Family Home
$6,075,000
12/17/25
4
5.5
5,935
3300 Gin LN, Naples, FL
0.73
Single-Family Home
$23,200,000
10/27/25
5
7.5
8,187
1212 Spyglass Ln, Naples, FL
1.03
Single-Family Home
$15,900,000
04/06/26
5
5.5
7,997

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
4253 Cutlass LN, Naples, FL 34102
0.07
$32,850,000
5
6
6,883
For Sale
4296 Cutlass LN, Naples, FL 34102
0.10
$55,000,000
6
10.5
15,309
Recently Sold
225 Cove LN, Naples, FL 34102
0.19
$12,881,800
4
6.5
7,454
Off Market
4120 Cutlass LN, Naples, FL 34102
0.18
$13,927,000
6
6.5
7,964
Off Market
4115 Cutlass LN, Naples, FL 34102
0.18
$25,000,000
6
7
6,291
Recently Sold
61 COVE LN, Naples, FL 34102
0.23
$800,000
-
-
-
Recently Sold
63 Cove LN, Naples, FL 34102
0.24
$3,651,800
-
-
-
Off Market
230 & 240 Bay RD, Naples, FL 34102
0.27
$31,000,000
Studio
-
1,000
For Sale
12 Sabre LN, Naples, FL 34102
0.26
$17,900,000
6
8.5
7,211
For Sale
4550 GORDON DR, Naples, FL 34102
0.30
$49,950,000
-
-
-
For Sale
605 Admiralty Parade W, Naples, FL 34102
0.26
$16,185,400
6
6.5
6,044
Off Market
700 Admiralty Parade W, Naples, FL 34102
0.26
$24,001,800
5
6
7,640
Off Market

Local Information

  • Map ViewExplore the area around 4305 Cutlass Ln.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1991
0.94 acre lot
6,314 sqft
$3,600/sqft
Garage

About this House

One of the most beautiful waterfront properties in all of Naples ! Built by Newbury North Associates, Inc. and designed by Jerry DeGennaro, this 4 bedroom plus a den home is a perfection combination of Old Florida and New England architecture. Port Royal Club and Cutlass Cove Beach Club membership eligibility.
4305 Cutlass Ln, Naples, FL 34102 is a 4 bedroom, 8 bathroom, 6,314 sqft single-family home in Port Royal, built in 1991. It last sold for $16,000,000 on Sep 1, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $22,733,500.

Home Details for 4305 Cutlass Ln

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2ElevatorFloors: Other, CarpetGated Entry
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Family Room, Laundry Room, Library, Master Bath, Office, PantryCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Security
Security System

Exterior Features

Exterior Home Features
Roof: Built Up, Other, Shake ShingleDeckExterior: WoodLawnSprinkler System
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 1991Year Updated: 1991
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Community

Units in Building: 1

Lot Information

Lot Area: 0.94 acres

Price and Tax history

DateEventPrice
Sep 1, 2024
Source: SWFLMLS #221016154
ListingRemoved
$16,950,000
Oct 26, 2022
Source: SWFLMLS #221016154
ListingRemoved
Sep 1, 2021
Source: N/A
Sold
$16,000,000
Jul 9, 2021
Source: SWFLMLS #221016154
PriceChange
$16,950,000
Price decreased by 5%
Jun 25, 2021
Source: SWFLMLS #221016154
PendingToActive
$17,900,000

Market trends in Naples

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$550K
$18.33KMoM
Sale-to-List Price
95.0%
0.1%MoM
Price per sq ft
$323
$9MoM
Available listings
4452
376MoM

Around this home

Neighborhood Overview

Port Royal
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Port Royal

At least 4 Trulia users voted on each feature.

  • 100 % Say parking is easy

  • 100 % Say it's dog friendly

  • 100 % Say people would walk alone at night

  • 100 % Say car is needed

  • 78 % Say it's quiet

  • 75 % Say there's holiday spirit

  • 67 % Say they plan to stay for at least 5 years

  • 50 % Say yards are well-kept

  • 43 % Say there's wildlife

  • 39 % Say neighbors are friendly

  • 25 % Say streets are well-lit

  • 17 % Say it's walkable to restaurants

  • 17 % Say there are sidewalks

Sourced by Trulia users. Learn more about our methodology.
  • Eurobaby
    "I've done a fair amount of travel throughout the US-but never have I found a more perfectly planned and aesthetically pleasing place. Whether you're young, middle-aged, senior, living w/ children or empty nester, it just doesn't get much better than this on planet earth. "
    25
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 4305 Cutlass Ln

  • What is 4305 Cutlass Ln estimated to be worth?
    Trulia's estimated value for 4305 Cutlass Ln in Naples, FL is $22,733,500.
  • What is the price history for 4305 Cutlass Ln?
    4305 Cutlass Ln in Naples, FL last sold for $16,000,000 in September 2021.
  • Is Naples a buyer's or seller's market?
    Naples is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Naples?
    The median sale price in Naples is $550K. That is down $18.33K from the prior month.
  • Does 4305 Cutlass Ln have air conditioning?
    Yes, 4305 Cutlass Ln in Naples, FL has air conditioning.
  • Does 4305 Cutlass Ln have a pool?
    Yes, 4305 Cutlass Ln in Naples, FL has a pool.

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