4437 Wayside Dr, Naples, FL 34119
Property image
Property image
OFF MARKET

4437 Wayside Dr
Naples, FL 34119

  • 4 Beds
  • 4.5 Baths
  • 5,601 sqft (on 0.84 acres)

$4,518,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $26,859/mo*
Refinance Your Home

$4,518,200

Trulia Estimate
as of Aug 23, 2026
Est. Refi. Payment $26,859/mo*
Refinance Your Home
4 Beds
4.5 Baths
5,601 sqft
(on 0.84 acres)

Home Value

Trulia Estimate
$4.52M
Since last month
Increased$98K (+2.2%)
Since last year
Increased$447K (+10.8%)
Since last sale
Increased$2M (+94.4%)
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 +31% in the last 10 years
MonthEstimated value
2026
August 2026$4.57M
July 2026$4.47M
June 2026$4.52M
May 2026$4.42M
April 2026$4.35M
March 2026$4.25M
February 2026$4.29M
January 2026$4.12M
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
4484 Brynwood DR, Naples, FL
0.27
Single-Family Home
$3,600,000
06/29/26
4
4.5
6,213
4297 Deephaven LN, Naples, FL
0.14
Single-Family Home
$6,450,000
10/09/25
4
4.5
5,173
4468 Brynwood DR, Naples, FL
0.25
Single-Family Home
$6,125,000
11/20/25
4
4.5
4,972
5900 Burnham RD, Naples, FL
0.44
Single-Family Home
$3,950,000
04/15/26
4
5
4,869
4190 Cortland WAY, Naples, FL
0.35
Single-Family Home
$3,775,000
06/17/26
4
4.5
3,526
5923 Sunnyslope DR, Naples, FL
0.38
Single-Family Home
$3,725,000
01/05/26
5
5.5
4,758
4203 Cortland WAY, Naples, FL
0.34
Single-Family Home
$3,825,000
07/01/26
4
4.5
3,521
6511 Highcroft DR, Naples, FL
0.54
Single-Family Home
$4,100,000
10/01/25
4
4.5
6,233
13871 Williston WAY, Naples, FL
0.60
Single-Family Home
$4,000,000
01/05/26
4
4.5
5,030
28981 Somers Dr, Naples, FL
0.43
Single-Family Home
$4,850,000
04/15/26
4
5
4,661

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
4431 Wayside DR, Naples, FL 34119
0.04
$5,866,400
4
5
4,966
Off Market
4436 Wayside DR, Naples, FL 34119
0.05
$4,174,400
5
7.5
6,917
Off Market
6439 Dunberry LN, Naples, FL 34119
0.16
$6,550,700
5
6.5
7,390
Off Market
4309 Deephaven LN, Naples, FL 34119
0.16
$6,583,500
4
5
5,874
Off Market
4265 Deephaven LN, Naples, FL 34119
0.21
$3,620,700
4
4
3,800
Off Market
4473 Wayside DR, Naples, FL 34119
0.21
$5,828,600
4
4.5
5,498
Off Market
4468 Brynwood DR, Naples, FL 34119
0.25
$6,125,000
4
4.5
4,972
Recently Sold
4421 Brynwood DR, Naples, FL 34119
0.26
$7,510,200
4
5
6,092
Off Market
4262 Deephaven LN, Naples, FL 34119
0.25
$4,120,300
4
5.5
4,334
Off Market
4484 Brynwood DR, Naples, FL 34119
0.27
$3,600,000
4
4.5
6,213
Recently Sold
4249 Deephaven LN, Naples, FL 34119
0.27
$3,176,800
4
4.5
3,333
Off Market
4485 Brynwood DR, Naples, FL 34119
0.30
$2,525,000
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For Sale

Local Information

  • Map ViewExplore the area around 4437 Wayside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2007
Lot Size
0.84 acres
Living Area
5,601 sqft
Price/Sqft
$807
Parking
Garage

About this House

Custom built luxurious estate home with golf course, lake & preserve views. Single story, open split floor plan creates effortless easy living & fabulous entertaining atmosphere. Truly appreciate the indoor/outdoor flow of living, visit & see it for yourself; not enough space here to adequately describe all the features. Feel like royalty in the master suite enclave. Utilize the formal living room, dining room, wet bar, for memorable dinners; add the great room & covered outdoor living space to create a casual or larger event. Wait till you visit this KITCHEN! Gas & electric cooking, large fully equipped island, enough gorgeous wood cabinetry to hold all your daily & special occasion table service pieces and so much more! Family/great room features entertainment center & surround sound wired for living areas & master bedroom. Glass doors open to covered outdoor living space, outdoor kitchen, fireplace, eating/entertainment area just steps from oasis of plantings, resort style heated pool, spa, waterfall, fountain, & multiple sun lounges. Cabana bath leads to 3 large bedrooms, walk-in closets, & baths. Full Golf membership included!
4437 Wayside Dr, Naples, FL 34119 is a 4 bedroom, 5 bathroom, 5,601 sqft single-family home built in 2007. It last sold for $2,350,000 on Aug 5, 2019. It is currently off market. The Trulia Estimate is $4,518,200, with a rent estimate of $34,753/month.

Home Details for 4437 Wayside Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Interior Details
Additional StorageTypes of Rooms: Walk In Closet, Family Room, Office, PantryStorage
Appliances & Utilities
DishwasherDryerMicrowave
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Levels, Entrance, & Accessibility
Floors: CarpetGated Entry
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoPatioPorch
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2007Year Updated: 2007
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.84 acres

Building

Fitness & Sports
Basketball CourtTennis Court

Additional Information

Sport Court

Price and Tax history

DateEventPrice
Aug 5, 2019
Source: N/A
Sold
$2,350,000
Jun 7, 2019
Source: Agent Provided
Pending
$2,800,000
Sep 27, 2018
Source: Agent Provided
PendingToActive
$2,800,000
Sep 22, 2018
Source: Agent Provided
Pending
$2,800,000
Aug 14, 2018
Source: Agent Provided
PriceChange
$2,800,000
Price decreased by 6%

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

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. "
    0
    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

LGBTQ Local Legal Protections

Frequently asked questions about 4437 Wayside Dr

  • What is 4437 Wayside Dr estimated to be worth?
    Trulia's estimated value for 4437 Wayside Dr in Naples, FL is $4,518,200.
  • What is the price history for 4437 Wayside Dr?
    4437 Wayside Dr in Naples, FL last sold for $2,350,000 in August 2019.
  • 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 $568K. That is roughly unchanged from the prior month.
  • Does 4437 Wayside Dr have air conditioning?
    Yes, 4437 Wayside Dr in Naples, FL has air conditioning.
  • Does 4437 Wayside Dr have a pool?
    Yes, 4437 Wayside Dr in Naples, FL has a pool.

Explore by feature - Pet Friendly

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202 rentals with an outdoor space in Naples, FL

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Off Market Homes Near 4437 Wayside Dr

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