4253 Cutlass LN
Naples, FL 34102
Port Royal
5 Beds
6 Baths
6,883 sqft (on 0.73 acres)
5 Beds
6 Baths
6,883 sqft
(on 0.73 acres)
We estimate this home will sell faster than 95% nearby.
Local Information
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Description
An exceptionally rare lot and one-half with one of the most spectacular panoramic views in all of Port Royal. this exceptional waterfront estate offers 147 feet along one of the area’s deepest yacht basins, on no-wake waterfront with bay views —ideal for serious boating enthusiasts. The residence features 5 spacious bedrooms, each with its own ensuite bath, along with two additional half baths for guests. Designed for both comfort and entertaining, the home includes a private study, a dedicated media room, and expansive living spaces filled with natural light. Car collectors will appreciate the four-bay garage, thoughtfully designed with lift capabilities to maximize capacity. Owners are eligible for membership to the exclusive Port Royal Club and Cutlass Cove Beach Club, offering access to one of Naples’ most private beachfront experiences. This is a unique opportunity to own a premier property combining scale, location, and deep-water access in one of Naples’ most sought-after communities.
We estimate this home will sell faster than 95% nearby.
Home Highlights
Parking
4 Car Garage
Outdoor
Patio, Deck, Pool
View
Basin, Canal
HOA
None
Price/Sqft
$5,303
Listed
7 days ago
Home Details for 4253 Cutlass LN
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Interior Details Number of Rooms: 2Types of Rooms: Bedroom, Dining RoomWet Bar |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 7Number of Bathrooms (full): 5Number of Bathrooms (half): 2 |
Dimensions and Layout Living Area: 6883 Square Feet |
Appliances & Utilities Appliances: Gas Cooktop, Dishwasher, Disposal, Dryer, Freezer, Microwave, OtherDishwasherDisposalDryerLaundry: Inside,Laundry TubMicrowave |
Heating & Cooling Heating: Central,Natural GasHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central |
Fireplace & Spa Spa: In GroundNo FireplaceHas a Spa |
Gas & Electric Gas: Propane |
Windows, Doors, Floors & Walls Window: Skylight(s), Thermal, Storm Protection (Other)Door: French DoorsFlooring: Tile, Wood |
Levels, Entrance, & Accessibility Stories: 2Number of Stories: 2Levels: TwoFloors: Tile, Wood |
View Has a ViewView: Basin, Canal |
Security Security: Smoke Detector(s) |
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Exterior Home Features Roof: TilePatio / Porch: Deck, PatioExterior: Dock, Balcony, Outdoor Shower, Boat Lift, Elec Avail at dock, Hoist/Davit, Water Avail at DockFoundation: Concrete BlockHas a Private Pool |
Parking & Garage Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageParking Spaces: 4Parking: Attached |
Pool Pool: In GroundPool |
Frontage WaterfrontWaterfront: Basin, Canal FrontOn Waterfront |
Farm & Range Not Allowed to Raise Horses |
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Days on Market: 7 |
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Year Built Year Built: 1998 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: House |
Building Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction |
Property Information Parcel Number: 16860880001 |
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Price List Price: $36,500,000Price Per Sqft: $5,303 |
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MLS Status: Active |
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Direction & Address City: NAPLESCommunity: PORT ROYAL |
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Listing Agent Listing ID: 226016944 |
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Building Area Building Area: 10847 Square Feet |
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Community Features: Boating, Non-GatedNot Senior Community |
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Association for this Listing: NaplesNo HOAHOA Fee: No HOA Fee |
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Lot Area: 0.73 acres |
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Lease Term: Buyer Finance/Cash |
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Mls Number: 226016944Water ViewWater View: Basin, CanalAttribution Contact: 239-777-6622 |
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HOA Amenities: Beach Club Available,Private Beach Pavilion,Private Membership,See RemarksSource Internet Entire Listing Display |
Last check for updates: about 1 hour ago
Listing courtesy of Bill Earls, PA, (239) 777-6622
John R Wood Properties
Larry Lappin, Jr., (239) 571-8247
John R Wood Properties
Originating MLS: Naples
Source: SWFLMLS, MLS#226016944
Also Listed on SWFLMLS.
Price History for 4253 Cutlass LN
| Date | Price | Event | Source |
|---|---|---|---|
| 05/02/2026 | $36,500,000 | Listed For Sale | SWFLMLS #226016944 |
| 04/14/1995 | $1,650,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2024 |
|---|---|
| Tax | $117,364 |
| Assessment | $14,383,144 |
Home facts updated by county records
Comparable Sales for 4253 Cutlass LN
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.18 | Single-Family Home | $13,000,000 | 06/17/25 | 4 | 6.5 | 7,454 | |
0.12 | Single-Family Home | $25,000,000 | 02/25/26 | 6 | 7 | 6,291 | |
0.43 | Single-Family Home | $40,000,000 | 04/13/26 | 5 | 6 | 11,559 | |
0.55 | Single-Family Home | $20,500,000 | 08/29/25 | 5 | 7 | 7,706 | |
0.51 | Single-Family Home | $22,000,000 | 08/05/25 | 6 | 7.5 | 8,960 | |
0.65 | Single-Family Home | $8,550,000 | 04/30/26 | 6 | 6 | 4,584 | |
0.69 | Single-Family Home | $28,250,000 | 04/21/26 | 5 | 7 | 7,835 |
Assigned Schools
These are the assigned schools for 4253 Cutlass LN.
- Gulfview Middle School
- 6-8
- Public
- 604 Students
8/10GreatSchools RatingParent Rating AverageThis school honestly ruined my life and the three years I spent there were the worst In my life. The staff never did anything about bullying and they never contacted families unless there was an offense to the school itself. In my time there I had a total of 4 good teachers. In 6th grade a teacher wanted an honest review of her class from us, and I gave one. She would spend half of the class talking about her personal life and leave us with homework. When she saw my report on her class she took me into the hall and left the door open and started to berate me on my gifted status as well as my grades. When this was reported to administration all that happened was that I was switched to a different class, there was no punishment for any of her actions. My 7th grade math teacher there showed our class an animated political video discussing lizard people and the deep state. When our house flooded that same math teacher required me to rewrite all of the notes from the school year and there was no sympathy given from him. A group of kids literally got on all fours and started barking at me in the parking lot and because of the way any claim you made was dismissed I never reported it. In 8th grade my science teacher would pull up the attendance sheet that includes information about if a child has a 504 or IEP. You will get points taken off in gym class if you change in the bathrooms instead of the locker rooms, and at one point a random lady came and started recording us from outside of the fence. The way this school is run is disgusting and there are many teachers there that just need to retire. Do not send your children here.Other Review1y ago - Lake Park Elementary School
- PK-5
- Public
- 515 Students
10/10GreatSchools RatingParent Rating AverageThey do so much to make learning a great experience!Parent Review15y ago - Naples High School
- PK-12
- Public
- 1496 Students
6/10GreatSchools RatingParent Rating AverageWe have 3 kids in or through the school. Its got a great open campus, a diverse student body and some of the best athletics in the county. There are plenty of course offerings for all student levels.Parent Review2y ago 
Check out schools near 4253 Cutlass LN.
Neighborhood Overview
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
Learn more about our methodology.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Bill Earls, PA, John R Wood Properties
Agent Phone: (239) 777-6622
The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.
4253 Cutlass LN, Naples, FL 34102 is a 5 bedroom, 7 bathroom, 6,883 sqft single-family home built in 1998. 4253 Cutlass LN is located in Port Royal, Naples. This property is currently available for sale and was listed by SWFLMLS on May 2, 2026. The MLS # for this home is MLS# 226016944.