371 Bayside AVE, Naples, FL 34108
Property image
Property image
FOR SALE
3D VIEW
0.58 ACRES

$5,400,000

Original price: $5,900,000
  • 4 Beds
  • 4 Baths
  • 3,447 sqft (on 0.58 acres)

371 Bayside AVE, Naples, FL 34108

Est. Mortgage $32,431/mo*
Get Pre-Qualified

Home Highlights

Single-Family Home
Built in 1998
0.58 acre lot
$1,567/sqft
4 Car Garage

Local Information

  • Map ViewExplore the area around 371 Bayside AVE.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

A Rare Investment Opportunity in one of Naples’ Most Sought After Waterfront Communities. Where the beauty of Vanderbilt Bay meets boundless possibility, discover a property unlike any other in Conners. Spanning over .58 acres on a rare corner tip lot with more than 300 feet of pristine bay frontage, this extraordinary offering presents the chance to create something truly remarkable. Here, western exposure sunsets melt into the water, boats drift by in the golden light, and every view feels like a postcard. But beyond its beauty lies extraordinary investment potential—the opportunity to design a grand 11,000+ sq/ft waterfront estate, divide the parcel for dual residences, or reimagine the current home while planning your next masterpiece. A new seawall and dock (2019), along with a rare covered boathouse and sun deck, ensure this property is ready to enjoy today while holding immense value for tomorrow. Just two miles to the Gulf of Mexico via Wiggins Pass, the location offers seamless access for boaters and unbeatable proximity to Vanderbilt Beach, the Ritz-Carlton Resorts, LaPlaya, Mercato, and Naples’ finest dining and shopping. For the visionary investor or homeowner who understands that opportunity and beauty seldom converge—this is your moment. Endless views. Endless potential. Endless Naples waterfront lifestyle.
Last check for updates: about 24 hours ago
Listing courtesy of Debbie Pappas-Burback, PA, (239) 404-4900
Compass Florida LLC
Originating MLS: Naples
Source: SWFLMLS, MLS#225072095
Also Listed on SWFLMLS.

Home Details for 371 Bayside AVE

Interior Features

Interior Details
Number of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Garage, Kitchen, Lanai, Living RoomWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 4
Dimensions and Layout
Living Area: 3447 Square Feet
Appliances & Utilities
Appliances: Electric Cooktop, Dishwasher, Disposal, Microwave, Refrigerator/Freezer, Self Cleaning Oven, WasherDishwasherDisposalLaundry: InsideMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: In Ground, Equipment Stays, Heated, BathNo FireplaceHas a Spa
Gas & Electric
Gas: Propane
Windows, Doors, Floors & Walls
Window: Window Coverings, Shutters Electric, Shutters - ManualDoor: Zero/Corner Door SlidersFlooring: Concrete, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: Multi/SplitFloors: Concrete, Tile, Wood
View
Has a ViewView: Bay, Gulf and Bay, Partial Gulf
Security
Security: Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Deck, Screened Lanai/PorchOther Structures: Boat HouseExterior: Dock, Boat Slip, Balcony, Outdoor Shower, Boat Canopy/Cover, Boat Lift, Elec Avail at dock, Hoist/Davit, Water Avail at DockFoundation: Concrete Block, Poured ConcreteHas a Private Pool
Parking & Garage
Number of Garage Spaces: 4Number of Covered Spaces: 4No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 4Parking: Circular Driveway,Attached
Pool
Pool: In Ground, Concrete, Equipment Stays, Electric HeatPool
Frontage
WaterfrontWaterfront: Bay, Canal Front, Intersecting Canal, Navigable Water, SeawallFrontage Type: Bay/HarborResponsible for Road Maintenance: Public Maintained RoadOn Waterfront
Farm & Range
Not Allowed to Raise Horses

Days on Market

Days on Market: 180+

Property Information

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, Concrete, Frame, Stucco, Vinyl SidingNot a New Construction
Property Information
Parcel Number: 27583080009

Price & Status

Price
List Price: $5,400,000Price Per Sqft: $1,567

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: NAPLESCommunity: CONNERS
School Information
Elementary School: NAPLES PARK ELEMENTARY SCHOOLJr High / Middle School: PINE RIDGE MIDDLE SCHOOLHigh School: BARRON COLLIER HIGH SCHOOL

Agent Information

Listing Agent
Listing ID: 225072095

Building

Building Area
Building Area: 11087 Square Feet

Community

Community Features: Fishing, Street Lights, BoatingNot Senior Community

HOA

Association for this Listing: NaplesNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.58 acres

Miscellaneous

Mls Number: 225072095Water ViewWater View: Bay, Gulf and Bay, Partial GulfAttribution Contact: 239-404-4900

Additional Information

HOA Amenities: Fish Cleaning Station,Fishing Pier,Internet Access,Streetlight,Underground UtilitySource Internet Entire Listing Display

Around this home

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
    Flag
  • Jeff W
    "What an awesome community. From the beach, to the restaurants, the berm, the amenities, people … just love Pelican Bay. "
    1
    Flag
  • 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
    Flag
  • Swatson645
    "There is so much space to walk your dog on nice sidewalks."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Lisa Ethier
    "Everyone would love living in my neighborhood it’s beautiful. It’s family oriented. Everyone gets along with everyone."
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Trulia User
    "Everyone in Naples is very kind and friendly. The crime rate is very low. It’s a very family friendly city. "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Kldaniel29
    "Family neighborhood great place laid back great schools nice place to live but pretty hot. Only set back"
    0
    Flag
  • Twalkercillins
    "Mostly retirees. Not a lot of children. Would not recommend for families with young children. Not very walkable."
    0
    Flag
  • Mccartneyjosh
    "It is a standard city commute with lengthy traffic lights and moderate to heavy traffic, but generally it is a normal commute "
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • Kim
    "Activities are organized by HOA director they always have lots of activities planned lots of fun "
    0
    Flag
  • 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
    Flag
  • Swatson645
    "Very convenient to major roads and businesses but quiet neighborhoods. Love this area! Just beautiful!!!"
    0
    Flag
  • 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
    Flag
  • Jkgc11
    "There are Lots of community parks and activities for children. Miles of bike paths. Near the beach. "
    0
    Flag
  • 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
    Flag
  • Trulia User
    "Easy commute. Beautiful area to live in. Lovely people, friendly, helpful, very neighborly and close to everything."
    1
    Flag

Market trends in Naples

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$568K
Sale-to-List Price
95.2%
Price per sq ft
$331
$1MoM
Available listings
4813
415MoM

Home Value

Trulia Estimate
$5.02M
Since last month
Increased$205K (+4.3%)
Since last year
Decreased$536K (-9.6%)
Since last sale
Increased$5M (+1,334.6%)
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 +43% in the last 10 years
MonthEstimated value
2026
September 2026$5.02M
August 2026$4.82M
June 2026$4.82M
May 2026$5.26M
April 2026$5.27M
March 2026$5.27M
February 2026$5.26M
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
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
0.16
Single-Family Home
$3,200,000
05/15/26
5
3.5
3,184
427 Willet Ave, Naples, FL
0.23
Single-Family Home
$3,275,000
07/20/26
4
4
3,269
434 Trade Winds AVE, Naples, FL
0.13
Single-Family Home
$4,250,000
12/19/25
4
4
5,087
9602 Vanderbilt DR, Naples, FL
0.16
Single-Family Home
$1,445,000
12/11/25
3
2.5
2,245
414 Palm CT, Naples, FL
0.26
Single-Family Home
$6,500,000
01/28/26
4
5.5
4,337
526 104th AVE N, Naples, FL
0.44
Single-Family Home
$2,150,000
06/23/26
5
3.5
2,817
536 97th AVE N, Naples, FL
0.25
Single-Family Home
$1,418,000
06/03/26
4
3
2,227
9940 Vanderbilt DR, Naples, FL
0.20
Single-Family Home
$1,075,000
12/15/25
3
2
1,832

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
404 Bayside AVE, Naples, FL 34108
0.05
$2,600,000
4
4.5
3,026
Recently Sold
342 Bayside AVE, Naples, FL 34108
0.03
$3,934,100
-
-
-
Off Market
368 Bayside AVE, Naples, FL 34108
0.04
$7,735,400
5
5
7,492
Off Market
432 Bayside AVE, Naples, FL 34108
0.07
$5,975,000
4
4.5
4,293
For Sale
369 Pine AVE, Naples, FL 34108
0.08
$4,168,500
3
2.5
2,109
Off Market
419 Pine AVE, Naples, FL 34108
0.09
$1,817,900
4
4
3,666
Off Market
388 Pine AVE, Naples, FL 34108
0.10
$3,945,000
4
5.5
3,384
For Sale
366 Pine AVE, Naples, FL 34108
0.11
$3,500,000
-
-
-
For Sale
319 Lagoon AVE, Naples, FL 34108
0.10
$4,350,000
4
4.5
4,278
For Sale
362 Trade Winds AVE, Naples, FL 34108
0.12
$1,550,000
-
-
-
Recently Sold
481 Lagoon AVE, Naples, FL 34108
0.14
$2,237,300
3
2
1,660
Off Market

Price and Tax history

DateEventPrice
Jun 5, 2026
Source: SWFLMLS #225072095
PriceChange
$5,400,000
Price decreased by 8%
Jan 23, 2026
Source: SWFLMLS #225072095
PriceChange
$5,900,000
Price decreased by 5%
Sep 30, 2025
Source: SWFLMLS #225072095
Listed For Sale
$6,200,000
Jul 28, 2025
Source: SWFLMLS #225011611
ListingRemoved
$6,500,000
Apr 18, 2025
Source: SWFLMLS #225011611
PriceChange
$6,500,000
Price decreased by 13%

LGBTQ Local Legal Protections

Debbie Pappas-Burback, PA, Compass Florida LLC
Agent Phone: (239) 404-4900
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.

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Frequently asked questions about 371 Bayside AVE

  • What is the estimated monthly payment for 371 Bayside AVE?
    Based on a $5,400,000 list price with 20% down at today's rates, the estimated monthly payment for 371 Bayside AVE in Naples, FL is approximately $32,857 (about $28,417 principal & interest, $4,365 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 371 Bayside AVE compare to homes in Naples?
    371 Bayside AVE in Naples, FL is listed at $5,400,000, about 850% above the $568K median sale price in Naples.
  • What do residents say about Naples?
    Residents describe Naples, FL as dog-friendly, easy to park in, and quiet. Most residents say you need a car. See homes for sale in Naples, FL.
  • What are the closest schools to 371 Bayside AVE?
    The closest schools to 371 Bayside AVE in Naples, FL are Aubrey Rogers High School (rated 6/10), Naples Park Elementary School (Pre-K, rated 7/10), Pine Ridge Middle School (rated 9/10).
  • Does 371 Bayside AVE have air conditioning?
    Yes, 371 Bayside AVE in Naples, FL has air conditioning.
  • Does 371 Bayside AVE have a pool?
    Yes, 371 Bayside AVE in Naples, FL has a pool.
371 Bayside AVE, Naples, FL 34108 is a 4 bedroom, 4 bathroom, 3,447 sqft single-family home built in 1998. This property is currently available for sale and was listed by SWFLMLS on Sep 30, 2025. The MLS # for this home is MLS# 225072095.