4436 Wayside DR, Naples, FL 34119
Property image
Property image
OFF MARKET

$4,248,100

Trulia Estimate
  • 5 Beds
  • 7.5 Baths
  • 6,917 sqft (on 0.77 acres)

4436 Wayside DR, Naples, FL 34119

Est. Refi. Payment $25,012/mo*
Refinance Your Home
Currently Off Market - Sold Jul 15, 2025 for $4,325,000

Home Value

Trulia Estimate
$4.25M
Since last month
Increased$67K (+1.6%)
Since last year
Decreased$36K (-0.9%)
Since last sale
Decreased$84K (-1.9%)
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 +26% in the last 10 years
MonthEstimated value
2026
August 2026$4.24M
August 2026$4.23M
July 2026$4.17M
June 2026$4.23M
May 2026$4.14M
March 2026$4.19M
February 2026$4.29M
January 2026$4.17M
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
4297 Deephaven LN, Naples, FL
0.09
Single-Family Home
$6,450,000
10/09/25
4
4.5
5,173
5923 Sunnyslope DR, Naples, FL
0.34
Single-Family Home
$3,725,000
01/05/26
5
5.5
4,758
4484 Brynwood DR, Naples, FL
0.32
Single-Family Home
$3,600,000
06/29/26
4
4.5
6,213
4244 Brynwood DR, Naples, FL
0.57
Single-Family Home
$4,150,000
11/07/25
5
6.5
7,511
5900 Burnham RD, Naples, FL
0.41
Single-Family Home
$3,950,000
04/15/26
4
5
4,869
13700 Pondview CIR, Naples, FL
0.58
Single-Family Home
$4,650,000
04/15/26
6
6.5
7,217
4468 Brynwood DR, Naples, FL
0.29
Single-Family Home
$6,125,000
11/20/25
4
4.5
4,972
4190 Cortland WAY, Naples, FL
0.33
Single-Family Home
$3,775,000
06/17/26
4
4.5
3,526
6511 Highcroft DR, Naples, FL
0.54
Single-Family Home
$4,100,000
10/01/25
4
4.5
6,233

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
0.06
$5,915,200
4
5
4,966
Off Market
4309 Deephaven LN, Naples, FL 34119
0.12
$6,689,700
4
5
5,874
Off Market
4265 Deephaven LN, Naples, FL 34119
0.18
$3,640,700
4
4
3,800
Off Market
4262 Deephaven LN, Naples, FL 34119
0.21
$4,133,300
4
5.5
4,334
Off Market
6439 Dunberry LN, Naples, FL 34119
0.20
$6,596,800
5
6.5
7,390
Off Market
4473 Wayside DR, Naples, FL 34119
0.21
$5,853,500
4
4.5
5,498
Off Market
4249 Deephaven LN, Naples, FL 34119
0.25
$3,188,500
4
4.5
3,333
Off Market
5871 Sunnyslope DR, Naples, FL 34119
0.30
$6,189,700
4
5
5,017
Off Market
5865 Sunnyslope DR, Naples, FL 34119
0.30
$6,754,100
4
5
5,506
Off Market
4203 Cortland WAY, Naples, FL 34119
0.31
$3,825,000
4
4.5
3,521
Recently Sold
4468 Brynwood DR, Naples, FL 34119
0.29
$6,125,000
4
4.5
4,972
Recently Sold

Local Information

  • Map ViewExplore the area around 4436 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
1999
Lot Size
0.77 acres
Living Area
6,917 sqft
Price/Sqft
$614
Parking
4 Car Garage
HOA
$1,876/Monthly

About this House

TRANSFERABLE GOLF AND BEACH CLUB MEMBERSHIPS AVAILABLE IMMEDIATELY! Welcome to the epitome of luxury living at 4436 Wayside Drive, nestled in the prestigious Quail West community in Naples, FL. This stunning residence offers an unparalleled lifestyle with its exquisite design and top-notch amenities. Upon entering, you are greeted by a breathtaking chandelier, a true showstopper that sets the tone for the elegance and sophistication found throughout the home. The soaring ceilings and open floor plan seamlessly blend elegance with comfort. The gourmet kitchen is a chef's dream, featuring high-end appliances, custom cabinetry, and a spacious island adorned with under counter illuminating lights beneath the exquisite new quartzite countertops, creating a captivating ambiance perfect for entertaining. This home boasts a newer clay tile roof, ensuring both durability and timeless style. The freshly painted exterior and interior provide a modern and pristine look throughout. New countertops grace every room, adding a touch of luxury and sophistication. The property is surrounded by new landscaping and landscape lights, enhancing its curb appeal and creating a serene outdoor environment. For peace of mind, storm shutters with electric remotes are installed, offering convenience and protection. Throughout the home, you'll find all-new designer lighting, adding a touch of elegance and modern flair to every space. The master suite is a private oasis, complete with a spa-like bathroom and expansive walk-in closets. Large windows throughout the home provide breathtaking views of the lush landscaping and the pristine golf course. Situated on the 10th hole of the Preserve Course, this home offers direct access to the beauty and challenge of the course right from your backyard. Adding to the allure, this property includes a FULLY TRANSFERRABLE GOLF MEMBERSHIP AND 2 GOLF CARTS allowing you to enjoy the two championship golf courses at Quail West to the fullest. The community is renowned for its world-class amenities, including a state-of-the-art fitness center and a luxurious clubhouse offering dining and social events. Nearby, you'll find upscale shopping and dining options at Mercato and Waterside Shops, as well as the beautiful beaches of Naples. Four car garage, and Kohler house generator. This property is more than just a home; it's a lifestyle. Don't miss the opportunity to experience the best of Naples living in this extraordinary residence.
4436 Wayside DR, Naples, FL 34119 is a 5 bedroom, 8 bathroom, 6,917 sqft single-family home built in 1999. It last sold for $4,325,000 on Jul 15, 2025 (13% below the $4,995,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $4,248,100, with a rent estimate of $7,604/month.
Last check for updates: about 2 hours ago
Listed by AMY Zern, (847) 772-0128
Premier Sotheby's Int'l Realty
Bought with: Marc Galanto, (860) 839-3424, John R Wood Properties
Co-Buyer's Agent: Lynne Hancock, (239) 289-4272, John R Wood Properties
Originating MLS: Naples
Source: SWFLMLS, MLS#224004407

Home Details for 4436 Wayside DR

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Bedroom, Dining Room, KitchenWet Bar
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 8Number of Bathrooms (full): 7Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 6917 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Dishwasher, Disposal, Double Oven, Dryer, Grill - Gas, Microwave, Range, Refrigerator/Freezer, Walk-In Cooler, Warming Tray, Washer, Wine CoolerDishwasherDisposalDryerMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: In Ground, Heated, Pool Bath, BathHas a FireplaceHas a Spa
Gas & Electric
Gas: Propane
Windows, Doors, Floors & Walls
Window: Window Coverings, Shutters ElectricDoor: French Doors, Zero/Corner Door SlidersFlooring: Carpet, Tile
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Tile
View
Has a ViewView: Golf Course
Security
Security: Security System, Gated Community, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: TilePatio / Porch: Patio, Screened Lanai/PorchFencing: FencedOther Structures: Tennis Court(s), Outdoor KitchenExterior: Outdoor Grill, Outdoor KitchenFoundation: Concrete BlockHas 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: Community, In Ground, Gas Heat, InfinityPool
Frontage
Waterfront: NoneFrontage Type: Golf CourseRoad Surface Type: PavedNot on Waterfront
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 1999
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: 68985000824

Price & Status

Price
List Price: $4,995,000
Status Change & Dates
Off Market Date: Tue Jul 15 2025

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: NAPLESCommunity: QUAIL WEST

Building

Building Area
Building Area: 9074 Square Feet
Community rooms
Fitness Center

Community

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

HOA

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

Lot Information

Lot Area: 0.77 acres

Offer

Contingencies: Financing

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 224004407

Additional Information

HOA Amenities: Basketball Court,Barbecue,Beauty Salon,Bike And Jog Path,Bocce Court,Business Center,Clubhouse,Pool,Community Room,Concierge,Fitness Center,Full Service Spa,Golf Course,Guest Room,Internet Access,Pickleball,Play Area,Putting Green,Racquetball,Restaurant,Sauna,Shopping,Sidewalk,Streetlight,Tennis Court(s)

Price and Tax history

DateEventPrice
Jul 15, 2025
Source: SWFLMLS #224004407
Sold
$4,325,000
May 6, 2025
Source: SWFLMLS #224004407
Pending
$4,995,000
Apr 23, 2025
Source: SWFLMLS #224004407
PendingToActive
$4,995,000
Apr 21, 2025
Source: SWFLMLS #224004407
Pending
$4,995,000
Mar 20, 2025
Source: SWFLMLS #224004407
PriceChange
$4,995,000
Price decreased by 11%

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
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  • 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

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 4436 Wayside DR

  • What is 4436 Wayside DR estimated to be worth?
    Trulia's estimated value for 4436 Wayside DR in Naples, FL is $4,248,100.
  • What is the price history for 4436 Wayside DR?
    4436 Wayside DR in Naples, FL last sold for $4,325,000 in July 2025.
  • 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 4436 Wayside DR have air conditioning?
    Yes, 4436 Wayside DR in Naples, FL has air conditioning.
  • Does 4436 Wayside DR have a pool?
    Yes, 4436 Wayside DR in Naples, FL has a pool.

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