4448 Wayside Dr
Naples, FL 34119
- 4 Beds
- 6 Baths
- 6,563 sqft (on 0.81 acres)
4 Beds
6 Baths
6,563 sqft
(on 0.81 acres)
Local Information
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Description
The ultimate country club lifestyle awaits at this spectacular custom-built Quail West estate home! The sprawling single story layout was designed for entertaining, offering a living room, family room with sunken bar, open kitchen with wet bar and breakfast nook, dining room with french doors out to a fountain courtyard, 3 en suite bedrooms, a private study, laundry room and a powder room in the main house. The master suite has dual bathrooms, a sitting area and a "morning bar" with mini fridge. An oversized screened lanai and large pool deck with a heated pool and separate gas-heated hot tub overlook a pristine stretch of the course's widest fairway. Off the lanai, find a guest cabana complete with a kitchenette, sitting area and full bathroom. The property comes with a fully transferable Quail West Golf Club membership and even includes use of the owners' golf cart, stored in the 3 car garage! Quail West Country Club offers a newly expanded 70,000 square foot Grand Clubhouse, two championship golf courses, gourmet dining, an indoor lagoon style pool, 8 red clay tennis courts and a full service salon and spa.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
Porch, Deck, Pool
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 4448 Wayside Dr
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Heating & Cooling Heating: Other, GasAir ConditioningCooling System: CentralHeating Fuel: Other |
Interior Details Types of Rooms: Walk In ClosetWet Bar |
Appliances & Utilities DishwasherDryerMicrowaveRefrigeratorWasher |
Fireplace & Spa FireplaceHot Tub or Spa |
Levels, Entrance, & Accessibility Floors: Tile, Carpet, Hardwood |
Security Security System |
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Exterior Home Features Roof: TileDeckExterior: Other, StuccoPorch |
Pool Pool |
Parking & Garage GarageParking Spaces: 3Parking: Garage Attached |
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Year Built Year Built: 1999Year Updated: 1999 |
Property Type / Style Property Type: Single Family HomeArchitecture: Other |
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Furnished |
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Units in Building: 1 |
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Lot Area: 0.81 acres |
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Community rooms Fitness Center |
Fitness & Sports Tennis Court |
Price History for 4448 Wayside Dr
| Date | Price | Event | Source |
|---|---|---|---|
| 08/04/2019 | $27,000 | ListingRemoved | Agent Provided |
| 08/04/2018 | $27,000 | Listed For Rent | Agent Provided |
| 04/11/2018 | $1,900,000 | Sold | N/A |
| 01/30/2018 | $1,990,000 | Pending | Agent Provided |
| 12/18/2017 | $1,990,000 | Listed For Sale | Agent Provided |
| 08/01/2017 | $2,090,000 | ListingRemoved | Agent Provided |
| 02/25/2017 | $2,090,000 | PriceChange | Agent Provided |
| 10/26/2016 | $2,190,000 | PriceChange | Agent Provided |
| 01/23/2016 | $2,350,000 | PriceChange | Agent Provided |
| 07/23/2015 | $2,495,000 | PriceChange | Agent Provided |
| 04/02/2015 | $2,650,000 | PriceChange | Agent Provided |
| 02/09/2015 | $2,750,000 | PriceChange | Agent Provided |
| 04/08/2014 | $2,850,000 | Listed For Sale | Agent Provided |
| 06/14/1996 | $350,000 | Sold | N/A |
Market trends in Naples
Last updated April 2026
Avg. sale price
$589K $10.33KMoM
Sale-to-List Price
95.2% 0.1%MoM
Price per sq ft
$327 $5MoM
Available listings
6576 386MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $30,261 |
| Assessment | $3,155,856 |
Home facts updated by county records
Comparable Sales for 4448 Wayside Dr
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.07 | Single-Family Home | $4,325,000 | 07/15/25 | 5 | 7.5 | 6,917 | |
0.12 | Single-Family Home | $6,450,000 | 10/09/25 | 4 | 4.5 | 5,173 | |
0.36 | Single-Family Home | $3,950,000 | 04/15/26 | 4 | 5 | 4,869 | |
0.32 | Single-Family Home | $3,725,000 | 01/05/26 | 5 | 5.5 | 4,758 | |
0.36 | Single-Family Home | $4,850,000 | 04/15/26 | 4 | 5 | 4,661 | |
0.29 | Single-Family Home | $6,125,000 | 11/20/25 | 4 | 4.5 | 4,972 | |
0.38 | Single-Family Home | $3,750,000 | 07/08/25 | 4 | 4.5 | 4,463 | |
0.46 | Single-Family Home | $6,345,000 | 03/25/26 | 4 | 4.5 | 5,938 | |
0.52 | Single-Family Home | $4,000,000 | 01/05/26 | 4 | 4.5 | 5,030 | |
0.40 | Single-Family Home | $7,550,000 | 05/20/26 | 4 | 4.5 | 4,931 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 4448 Wayside Dr.
What Locals Say about Naples
At least 1692 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
61 % Say streets are well-lit
61 % Say yards are well-kept
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.
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4448 Wayside Dr, Naples, FL 34119 is a 4 bedroom, 6 bathroom, 6,563 sqft single-family home built in 1999. This property is not currently available for sale. 4448 Wayside Dr was last sold on Apr 11, 2018 for $1,900,000. The current Trulia Estimate for 4448 Wayside Dr is $4,124,900.

