419 Pine AVE, Naples, FL 34108
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Property image
OFF MARKET

419 Pine AVE
Naples, FL 34108

  • 4 Beds
  • 4 Baths
  • 3,666 sqft (on 0.25 acres)

$1,794,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $10,686/mo*
Refinance Your Home

$1,794,600

Trulia Estimate
as of Aug 6, 2026
Est. Refi. Payment $10,686/mo*
Refinance Your Home
4 Beds
4 Baths
3,666 sqft
(on 0.25 acres)

Local Information

  • Map ViewExplore the area around 419 Pine AVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1971
Lot Size
0.25 acres
Living Area
3,666 sqft
Price/Sqft
$490
Parking
2 Car Garage
HOA
None

About this House

LIVE THE WATERFRONT LIFESTYLE — BUILD FOR TOMORROW. Located on one of the most sought-after streets in Naples, this two-story home sits on an oversized waterfront lot in the prestigious Vanderbilt Beach area. Just a short stroll to white sandy beaches and minutes by boat to the Gulf of Mexico, this property offers the ultimate in coastal convenience. Enjoy the Florida lifestyle today, or reimagine the future — with gulf access, an 8’ x 53’ dock equipped with water and electric, and a 12,000 lb. boat lift already in place, the lot alone offers exceptional value for boaters and investors alike. Whether you’re looking to move in, renovate, or build new, this parcel presents a rare opportunity to own in a prime location surrounded by new luxury construction. The current residence features a gourmet kitchen with granite countertops, solid oak floors upstairs, designer tile downstairs, and a layout filled with natural light, vaulted ceilings, and expansive water views. French doors open to a screened lanai and paver patio, creating an ideal indoor-outdoor flow. Upstairs, a balcony and catwalk overlook the wide canal, perfect for sunset watching and entertaining. The primary suite includes double vanities, marble countertops, a jetted garden tub, and a walk-in shower with glass block accents. SOLD AS-IS, with Right to Inspect. While the home has experienced past flooding, it has also been maintained and enjoyed — and the true value lies in the land, the location, and the potential. Whether you choose to live now and build later, or create your dream waterfront retreat from the ground up, 419 Pine Ave is your gateway to the best of Naples living.
419 Pine AVE, Naples, FL 34108 is a 4 bedroom, 4 bathroom, 3,666 sqft single-family home built in 1971. It last sold for $1,850,000 on Aug 15, 2025 (7% below the $1,995,000 asking price). It is currently off market. The Trulia Estimate is $1,794,600, with a rent estimate of $7,136/month.

Home Details for 419 Pine AVE

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Bedroom, Dining Room, Kitchen
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 3666 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Dishwasher, Dryer, Microwave, Refrigerator/Freezer, WasherDishwasherDryerMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Skylight(s), Impact Resistant WindowsDoor: Impact Resistant DoorsFlooring: Marble
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Marble
View
Has a ViewView: Bay, Canal
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Patio, Screened Lanai/PorchExterior: Dock, Balcony, Boat Lift, Jet Ski LiftFoundation: Concrete BlockNo Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Circular Driveway,Driveway,Attached
Frontage
WaterfrontWaterfront: Bay, Canal FrontFrontage Type: Bay/HarborResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedOn Waterfront
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 1971
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: House
Building
Construction Materials: Block, StuccoNot a New Construction
Property Information
Parcel Number: 27582520007

Price & Status

Price
List Price: $1,995,000
Status Change & Dates
Off Market Date: Fri Aug 15 2025

Active Status

MLS Status: Closed

Location

Direction & Address
City: NAPLESCommunity: CONNERS
School Information
Elementary School: NAPLES PARK ELEMENTARYJr High / Middle School: PINE RIDGE MIDDLEHigh School: BARRON COLLIER HIGH SCHOOL

Building

Building Area
Building Area: 4773 Square Feet

Community

Community Features: Boating, Non-GatedNot Senior Community

HOA

Association for this Listing: NaplesNo HOA

Lot Information

Lot Area: 10890 sqft

Miscellaneous

Mls Number: 225037757Water ViewWater View: Bay, Canal

Additional Information

HOA Amenities: None
Last check for updates: about 2 hours ago
Listed by Nick Sadowski, (239) 378-0300
Berkshire Hathaway FL Realty
Bought with: Chris Schaller, (239) 450-7808, Downing Frye Realty Inc.
Originating MLS: Naples
Source: SWFLMLS, MLS#225037757

Price History for 419 Pine AVE

DatePriceEventSource
08/15/2025$1,850,000Sold
SWFLMLS #225037757
08/02/2025$1,995,000PendingSWFLMLS #225037757
05/01/2025$1,995,000PriceChange
SWFLMLS #225037757
04/14/2025$2,395,000Listed For SaleSWFLMLS #225037757
12/01/2009$609,000Sold
N/A
07/25/2009$699,900ListingRemovedAgent Provided
05/24/2009$699,900Listed For SaleAgent Provided
01/31/2009$899,900ListingRemovedAgent Provided
09/14/2008$899,900Listed For SaleAgent Provided
04/21/2005$1,310,000Sold
N/A

Market trends in Naples

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$568K
$19KMoM
Sale-to-List Price
95.2%
0.1%MoM
Price per sq ft
$330
$0MoM
Available listings
5204
766MoM
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Property Tax and Assessment

Year2025
Tax$20,230
Assessment$2,080,339
Home facts updated by county records

Comparable Sales for 419 Pine AVE

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
404 Bayside AVE, Naples, FL
0.05
Single-Family Home
$2,600,000
05/15/26
4
4.5
3,026
325 Oak Ave, Naples, FL
0.12
Single-Family Home
$3,200,000
05/15/26
5
3.5
3,184
9602 Vanderbilt DR, Naples, FL
0.10
Single-Family Home
$1,445,000
12/11/25
3
2.5
2,245
427 Willet Ave, Naples, FL
0.30
Single-Family Home
$3,275,000
07/20/26
4
4
3,269
434 Trade Winds AVE, Naples, FL
0.19
Single-Family Home
$4,250,000
12/19/25
4
4
5,087
542 92nd AVE N, Naples, FL
0.33
Single-Family Home
$1,650,000
04/15/26
3
3
3,093
536 97th AVE N, Naples, FL
0.20
Single-Family Home
$1,418,000
06/03/26
4
3
2,227
620 94th AVE N, Naples, FL
0.41
Single-Family Home
$3,437,500
05/19/26
4
4.5
3,726
558 100th AVE N, Naples, FL
0.31
Single-Family Home
$1,787,500
06/15/26
4
3
2,229

Nearby homes

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Assigned Schools

These are the assigned schools for 419 Pine AVE.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Naples

At least 1698 Trulia users voted on each feature.

  • 86 % Say it's dog friendly

  • 83 % Say car is needed

  • 78 % Say parking is easy

  • 75 % Say it's quiet

  • 69 % Say people would walk alone at night

  • 69 % Say there's holiday spirit

  • 67 % Say there are sidewalks

  • 62 % Say yards are well-kept

  • 61 % Say streets are well-lit

  • 60 % Say they plan to stay for at least 5 years

  • 53 % Say neighbors are friendly

  • 51 % Say there's wildlife

  • 48 % Say kids play outside

  • 47 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 39 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Mfontaine21
    "Many community events at our town center including food trucks, swim and dance parties and weekly bingo"
    0
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  • Jeff W
    "What an awesome community. From the beach, to the restaurants, the berm, the amenities, people … just love Pelican Bay. "
    0
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  • Trulia User
    "Safe neighborhoods but be wary of some of the complexes as you move east. Naples is amazing if you do your homework "
    0
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  • Swatson645
    "There is so much space to walk your dog on nice sidewalks."
    0
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  • Chad Roberson
    "Quiet, people leave you alone here. No hoa, can expand on your property. Weather is amazing 6-8 months out of the year. You’ll see amazing wildlife everywhere in this area. "
    0
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  • Jimandhelensimon
    "We have an excellent location to access numerous beaches and have an enormous amount of well landscaped green space. Our pool feels like a resort pool."
    0
    Flag
  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
    0
    Flag
  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
    0
    Flag
  • James
    "lots of green space in the area and there are dog parks that also can be visited by dog owners and the place is always well groomed"
    1
    Flag
  • Sandra Decain
    "Great friendly people - love the dining access to water amazing weather. Could not ask for more. "
    0
    Flag
  • Michael.mccann
    "Lovely and quiet. Great location with beach and shopping/dining nearby. Homes are well maintained "
    0
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  • Michelle SanFillipo
    "Great dog parks and open spaces for recreational activities. Safe and secure. Well lit at night. Wide sidewalks and others are respectful of dogs and clean up."
    1
    Flag
  • Cristiano Machado
    "Friendly and safe neighborhood Close to schools, lhospital and grocery stores plus great restaurants and pubs"
    0
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  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
    0
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  • Brian.bird
    "Fun people and safe gated community with golf and tennis and good food. Homes are nice and the grounds are well kept"
    0
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  • waterman46
    "Pet friendly all dogs on leashes . We have never had a problem and 99% pick up after their dogs. Just a really nice pet friendly area."
    1
    Flag
  • Jimandhelensimon
    "It’s dog friendly but dogs must be on a leash. The dogs must be twenty pounds or less unless they are an emotional support dog."
    0
    Flag
  • DonnaT
    "Naples is a great place to retire. It is paradise. The cost of living is outrageous but it is worth every penny! "
    0
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  • Wheeler04
    "The Isles is surrounded by nature with 1/2 of its 2,400 acres dedicated to preserve and waterways. Such a friendly and active community! "
    0
    Flag
  • Airwavessystem
    "I great community to live close to everything shops supermarkets and the beach. 15 minutes to the mall and 5 minutes to the main highway 75 to tampa Orlando or to miami."
    0
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  • Scottjohnnewhouse
    "I’ve lived in Naples for 33 years. It is growing at an alarming rate but it is such a safe place to live…."
    0
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  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
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  • Eric
    "There are a lot of young families with children out playing with each other. The community center is well equipped with gym equipment and a beautiful pool."
    0
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  • Oditth Ricardo
    "Peaceful and safe. No issues and no problems most of the time. Great schools. Great place to start a family and raise kids. "
    0
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  • Jimandhelensimon
    "Beautiful open spaces and amenities. Beaches and large variety of restaurants and entertainment. The shopping is awesome and the people are fun loving."
    0
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  • Laurel
    "This is a family friendly neighborhood. It is close to the beach, the Greenway, the zoo, parks, theater, shopping, and dining. It’s close to downtown Naples and just a few miles to The Mercato. "
    0
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  • Nmarranca
    "I am here on vacation and it is a wonderful community. We are in Beachwalk, which is very close to the beach and walking distance and we have a big pool."
    0
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  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
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  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
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  • Mccartneyjosh
    "It is a standard city commute with lengthy traffic lights and moderate to heavy traffic, but generally it is a normal commute "
    0
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  • Amolter
    "Lake park is close to everything anyone would want. Mall, restaurants, parks, dog park, hospital, grocery store, zoo, move theatre,downtown, boat launch to the bay, and the beach!!"
    0
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  • Blondbasket
    "Great groups of people live in the area. Everything is relatively easy and close to the house. I know my neighbors and they are so far very helpful and all around happy people. "
    0
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  • Kim
    "Activities are organized by HOA director they always have lots of activities planned lots of fun "
    0
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  • Kim
    "Very well kept sidewalks and community areas, yards are well maintained it’s so easily accessible to markets and stores very easy to walk around , biking is also easy to do there are nice friendly people "
    0
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  • Swatson645
    "Very convenient to major roads and businesses but quiet neighborhoods. Love this area! Just beautiful!!!"
    0
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  • Juntig5
    "Naples is a lovely place, tends to get crowded in the season, nice beaches and the city is clean with lots of restaurants. Pleasant weather. "
    0
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  • Jkgc11
    "There are Lots of community parks and activities for children. Miles of bike paths. Near the beach. "
    0
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  • Trulia User
    "Close to the beaches restaurant downtown feel like you on vacation family friendly and pet friendly neighborhood. Very clean and safe. Beautiful area "
    0
    Flag
  • Trulia User
    "Super nice location ! Close to beaches, downtown, everything you might want. Friendly neighbors. Close to restaurants, groceries, cafes. Beautiful homes. Historic homes "
    0
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  • Trulia User
    "Easy commute. Beautiful area to live in. Lovely people, friendly, helpful, very neighborly and close to everything."
    1
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Homes for sale near 419 Pine AVE

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Off Market Homes Near 419 Pine AVE

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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.