4431 Wayside DR, Naples, FL 34119
OFF MARKET

$5,800,300

Trulia Estimate
  • 4 Beds
  • 5 Baths
  • 4,966 sqft (on 0.84 acres)

4431 Wayside DR, Naples, FL 34119

Est. Refi. Payment $35,325/mo*
Refinance Your Home
Currently Off Market - Sold Oct 15, 2024 for $6,105,000

Home Value

Trulia Estimate
$5.8M
Since last month
Decreased$94K (-1.6%)
Since last year
Increased$138K (+2.4%)
Since last sale
Decreased$305K (-5%)
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 +115% in the last 10 years
MonthEstimated value
2026
September 2026$5.8M
August 2026$5.89M
July 2026$5.9M
June 2026$5.86M
May 2026$5.73M
April 2026$5.6M
March 2026$5.63M
February 2026$5.69M
January 2026$5.64M
2025
2024
2023
2022
2021
2020

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
4297 Deephaven LN, Naples, FL
0.14
Single-Family Home
$6,850,000
09/10/26
4
4.5
5,173
4468 Brynwood DR, Naples, FL
0.26
Single-Family Home
$6,125,000
11/20/25
4
4.5
4,972
4484 Brynwood DR, Naples, FL
0.29
Single-Family Home
$3,600,000
06/29/26
4
4.5
6,213
5949 Sunnyslope DR, Naples, FL
0.47
Single-Family Home
$7,550,000
05/20/26
4
4.5
4,931
6188 Freemont DR, Naples, FL
0.55
Single-Family Home
$6,345,000
03/25/26
4
4.5
5,938
4190 Cortland WAY, Naples, FL
0.32
Single-Family Home
$3,775,000
06/17/26
4
4.5
3,526
5054 Groveland TER, Naples, FL
0.58
Single-Family Home
$5,600,000
01/12/26
4
4.5
4,554
5900 Burnham RD, Naples, FL
0.46
Single-Family Home
$3,950,000
04/15/26
4
5
4,869

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
4436 Wayside DR, Naples, FL 34119
0.06
$4,212,000
5
7.5
6,917
Off Market
6439 Dunberry LN, Naples, FL 34119
0.18
$6,453,800
5
6.5
7,390
Off Market
4297 Deephaven LN, Naples, FL 34119
0.14
$6,850,000
4
4.5
5,173
Recently Sold
4309 Deephaven LN, Naples, FL 34119
0.17
$6,602,100
4
5
5,874
Off Market
4265 Deephaven LN, Naples, FL 34119
0.18
$3,583,600
4
4
3,800
Off Market
4473 Wayside DR, Naples, FL 34119
0.24
$5,849,800
4
4.5
5,498
Off Market
4468 Brynwood DR, Naples, FL 34119
0.26
$6,206,500
4
4.5
4,972
Off Market
4421 Brynwood DR, Naples, FL 34119
0.25
$7,741,700
4
5
6,092
Off Market
4262 Deephaven LN, Naples, FL 34119
0.22
$4,088,200
4
5.5
4,334
Off Market
4484 Brynwood DR, Naples, FL 34119
0.29
$3,600,000
4
4.5
6,213
Recently Sold
4249 Deephaven LN, Naples, FL 34119
0.24
$3,151,100
4
4.5
3,333
Off Market

Local Information

  • Map ViewExplore the area around 4431 Wayside DR.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2016
0.84 acre lot
4,966 sqft
$1,168/sqft
3 Car Garage
HOA $1,876/mo

About this House

Elegance and luxury meet functionality in this exquisite custom estate behind the gates of one of Naples’ most exclusive communities, Quail West. Immediate GOLF MEMBERSHIP and BEACH CLUB MEMBERSHIP available! This luxurious McGarvey built residence boasts unparalleled craftsmanship, panoramic golf course views and an opulent blend of sophistication and comfort. The inviting foyer sets the stage for what’s to come, revealing a preview of the outdoor oasis that awaits beyond the floor to ceiling glass windows. Indulge your culinary passions in the chef’s dream kitchen, featuring two islands and appointed with top-of-the-line Wolf appliances, Sub Zero Refrigerator and Freezer, and two Bosch dishwashers. The epitome of open-concept, each space effortlessly unfolds into the next. Pocketing glass doors disappear, seamlessly adjoining indoor and outdoor living spaces. The grandiose lanai boasts saltwater pool and spa, dual sided fireplace, fire pit and outdoor kitchen. Additional highlights include Control4 smart automation, temperature controlled wine cellar, media/cinema room, whole house generator and much, much more. Start living the life you’ve been dreaming about, today!
4431 Wayside DR, Naples, FL 34119 is a 4 bedroom, 6 bathroom, 4,966 sqft single-family home built in 2016. It last sold for $6,105,000 on Oct 15, 2024 (15% below the $7,199,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $5,800,300.
Last check for updates: about 5 hours ago
Listed by Roxanne Jeske, PA, (239) 450-5210
John R Wood Properties
Alyssa Heenan, (813) 928-2208
John R Wood Properties
Bought with: Brooke Walker, (865) 659-0856, John R Wood Properties
Originating MLS: Naples
Source: SWFLMLS, MLS#224010195

Home Details for 4431 Wayside DR

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Bedroom, Dining Room, KitchenWet Bar
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 6Number of Bathrooms (full): 4Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 4966 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Grill - Gas, Ice Maker, Microwave, Refrigerator/Icemaker, Self Cleaning Oven, Washer, Wine CoolerDishwasherDisposalDryerLaundry: Inside,Laundry TubMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: OutsideSpa: Community, In Ground, Concrete, Equipment Stays, Heated, Pool IntegratedHas a FireplaceHas a Spa
Gas & Electric
Gas: Propane
Windows, Doors, Floors & Walls
Window: Window Coverings, Impact Resistant Windows, Shutters ElectricDoor: Zero/Corner Door Sliders, Impact Resistant DoorsFlooring: Tile, Wood
Levels, Entrance, & Accessibility
Stories: 1Number of Stories: 1Floors: Tile, Wood
View
Has a ViewView: Golf Course
Security
Security: Security System, Smoke Detector(s), Gated Community

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Patio, Screened Lanai/PorchOther Structures: Tennis Court(s), Outdoor KitchenExterior: Outdoor Grill, Fire Pit, Outdoor KitchenFoundation: Concrete BlockHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Circular Driveway,Driveway,Attached
Pool
Pool: Community, Pool/Spa Combo, In Ground, Custom Upgrades, Equipment Stays, Electric Heat, Salt WaterPool
Frontage
Waterfront: NoneFrontage Type: Golf CourseRoad Surface Type: PavedNot on Waterfront
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 2016
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: Ranch
Building
Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction
Property Information
Parcel Number: 68985000507

Price & Status

Price
List Price: $7,199,000
Status Change & Dates
Off Market Date: Tue Oct 15 2024

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: NAPLESCommunity: QUAIL WEST

Building

Building Area
Building Area: 8469 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Pool, Fitness Center, Golf, Putting Green, Restaurant, Sidewalks, Street Lights, Tennis Court(s), GatedNot Senior Community

HOA

Association for this Listing: NaplesNo HOAHOA Fee: $22,516/Annually

Lot Information

Lot Area: 0.84 acres

Offer

Contingencies: Inspection

Miscellaneous

Mls Number: 224010195

Additional Information

HOA Amenities: Beauty Salon,Clubhouse,Pool,Community Room,Spa/Hot Tub,Concierge,Fitness Center,Full Service Spa,Golf Course,Internet Access,Pickleball,Play Area,Private Membership,Putting Green,Restaurant,Sauna,Sidewalk,Streetlight,Tennis Court(s),Underground Utility

Price and Tax history

DateEventPrice
Oct 15, 2024
Source: SWFLMLS #224010195
Sold
$6,105,000
Feb 22, 2024
Source: SWFLMLS #224010195
Pending
$7,199,000
Feb 5, 2024
Source: SWFLMLS #224010195
Listed For Sale
$7,199,000
Aug 3, 2021
Source: N/A
Sold
$4,125,000
Sep 4, 2014
Source: N/A
Sold
$500,000

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

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.
  • Silvia Polgati
    "Is a quiet neighborhood we really enjoy "
    0
    Flag
  • 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 "
    1
    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
  • 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
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  • 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

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.

Frequently asked questions about 4431 Wayside DR

  • What is 4431 Wayside DR estimated to be worth?
    Trulia's estimated value for 4431 Wayside DR in Naples, FL is $5,800,300.
  • What is the price history for 4431 Wayside DR?
    4431 Wayside DR in Naples, FL last sold for $6,105,000 in October 2024.
  • 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 4431 Wayside DR have air conditioning?
    Yes, 4431 Wayside DR in Naples, FL has air conditioning.
  • Does 4431 Wayside DR have a pool?
    Yes, 4431 Wayside DR in Naples, FL has a pool.

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