4442 Wayside Dr, Naples, FL 34119
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Property image
OFF MARKET

4442 Wayside Dr
Naples, FL 34119

  • 5 Beds
  • 6.5 Baths
  • 5,857 sqft (on 0.82 acres)

$4,632,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $27,510/mo*
Refinance Your Home

$4,632,000

Trulia Estimate
as of Jul 24, 2026
Est. Refi. Payment $27,510/mo*
Refinance Your Home
5 Beds
6.5 Baths
5,857 sqft
(on 0.82 acres)

Local Information

  • Map ViewExplore the area around 4442 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
2001
Lot Size
0.82 acres
Living Area
5,857 sqft
Price/Sqft
$791
Parking
Garage

About this House

Astonishing home on a sensational lot which also includes a Full Golf Membership to Quail West Golf & Country Club. Lake & wide Golf Course views from your immense lanai that are incredible. 5 Bedrooms plus den, 6-1/2 bathrooms, large living room, marvelous dining room with butler's galley way, open family room with zero corner sliding doors, private elevator, private outdoor kitchen, 3 private courtyards, and so much more. Every bedroom is in it's own corner of the house, with the 5th bedroom upstairs currently being used as a 2nd office, which makes for great privacy. Quail West has 8 lighted tennis courts, pickle ball, kid's play area, 2 championship golf courses, restaurants, 2-story fitness center, full-service spa and more. Live in a dream home in a prestigous golf course community.
4442 Wayside Dr, Naples, FL 34119 is a 5 bedroom, 7 bathroom, 5,857 sqft single-family home built in 2001. It last sold for $2,850,000 on May 5, 2021. It is currently off market. The Trulia Estimate is $4,632,000, with a rent estimate of $35,800/month.

Home Details for 4442 Wayside Dr

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Carpet, Hardwood
Interior Details
Types of Rooms: OfficeWet BarCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerRefrigeratorWasher
Fireplace & Spa
FireplaceHot Tub or SpaJetted Bath Tub
Security
Security System

Exterior Features

Exterior Home Features
Roof: TileDeckExterior: StuccoPorch
Pool
Pool
Parking & Garage
GarageParking Spaces: 3Parking: Garage Attached

Property Information

Year Built
Year Built: 2001Year Updated: 2001
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.82 acres

Building

Community rooms
Fitness Center
Fitness & Sports
Tennis Court

Additional Information

Intercom

Price History for 4442 Wayside Dr

DatePriceEventSource
05/05/2024ListingRemovedSWFLMLS #221001370
08/16/2022$2,995,000ListingRemovedSWFLMLS #221001370
05/05/2021$2,850,000Sold
Marco Multi List #2211548
02/05/2021$2,995,000PendingSWFLMLS #221001370
01/12/2021$2,995,000Listed For SaleSWFLMLS #221001370
09/07/2001$2,800,000Sold
N/A
10/19/1999$405,000Sold
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$30,236
Assessment$4,499,856
Home facts updated by county records

Comparable Sales for 4442 Wayside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5923 Sunnyslope DR, Naples, FL
0.33
Single-Family Home
$3,725,000
01/05/26
5
5.5
4,758
4297 Deephaven LN, Naples, FL
0.10
Single-Family Home
$6,450,000
10/09/25
4
4.5
5,173
4484 Brynwood DR, Naples, FL
0.31
Single-Family Home
$3,600,000
06/29/26
4
4.5
6,213
5900 Burnham RD, Naples, FL
0.38
Single-Family Home
$3,950,000
04/15/26
4
5
4,869
4468 Brynwood DR, Naples, FL
0.29
Single-Family Home
$6,125,000
11/20/25
4
4.5
4,972
28981 Somers Dr, Naples, FL
0.39
Single-Family Home
$4,850,000
04/15/26
4
5
4,661
4190 Cortland WAY, Naples, FL
0.36
Single-Family Home
$3,775,000
06/17/26
4
4.5
3,526
4565 Brynwood DR, Naples, FL
0.50
Single-Family Home
$3,825,000
10/20/25
5
4.5
4,807
13700 Pondview CIR, Naples, FL
0.55
Single-Family Home
$4,650,000
04/15/26
6
6.5
7,217
4244 Brynwood DR, Naples, FL
0.59
Single-Family Home
$4,150,000
11/07/25
5
6.5
7,511

Nearby homes

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Assigned Schools

These are the assigned schools for 4442 Wayside Dr.
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 1695 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.
  • 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
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  • Jarek Przada
    "Bingo, pool gymnastics, potluck, every holiday is celebrated in the community. There are pool parties and grill dinners."
    0
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  • Jimandhelensimon
    "This is more of a senior community. There are not many families with children here. The greater community is very family oriented."
    0
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  • 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
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  • 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
    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
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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
    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
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  • Jt276297
    "It’s one of the cleanest towns in the United States and has a vast number of culture with in it’s population "
    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
    Flag
  • 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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  • H5hnmg992c
    "none. i like that it isn’t gated. its a friendly neighborhood and people are kind. it’s becoming more accessible to food and restaurants"
    2
    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
  • Naplesjan29
    "The school’s are excellent and close by! It’s a very safe and convenient area!!The school bus picks up here daily."
    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

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Homes for sale near 4442 Wayside Dr

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Off Market Homes Near 4442 Wayside Dr

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