14769 Windward Ln, Naples, FL 34114
Property image
Property image
OFF MARKET

$887,800

Trulia Estimate
as of Sep 5, 2026
  • 3 Beds
  • 5 Baths
  • 2,585 sqft

14769 Windward Ln, Naples, FL 34114

Home Highlights

Single-Family Home
2,585 sqft
$343/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 14769 Windward Ln.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

NOW AVAILABLE | FEBRUARY APRIL 2026! Slip into winter the way it's meant to be experienced. Sun-drenched, effortless, and beautifully curated. This refined 3-bedroom + den, 5-bath residence is tucked within the coveted Naples Reserve, offering a serene lakefront setting designed for elevated seasonal living. The heart of the home is an expanded chef's kitchen, thoughtfully appointed with premium GE Cafe appliances, a statement proline range hood, granite countertops, custom glass-front cabinetry, a dedicated wine refrigerator, and a custom butler's pantry, ideal for hosting intimate dinners or relaxed evenings in. Living and dining spaces feel both polished and inviting, accented by custom wall detailing, designer lighting, and tranquil water views framed by an aquarium-style window. The private den, lined with built-in bookcases, provides a quiet space to work, read, or unwind. Outdoors, the lanai becomes a true extension of the home. A fully equipped gourmet outdoor kitchen, electric retractable screens, remote-controlled hurricane protection, and a convenient outdoor bath create a seamless indoor-outdoor lifestyle, perfect for evening dinners and leisurely afternoons overlooking the lake. The primary suite features dual custom walk-in closets and an oversized walk-in shower. Throughout the home, you'll find refined finishes including tray ceilings, crown molding, plantation shutters, wood-look tile flooring, and thoughtfully selected lighting and ceiling fans. Additional comforts include a well-appointed laundry room, an air-conditioned 3-car garage with built-in storage. As a seasonal resident, you'll enjoy Naples Reserve's amenities which features, a lagoon shaped resort style pool/lap pool, fitness center, tennis and pickleball courts, walking and biking trails, dog parks, community boats, a sandy beach area with volleyball, and more. Naples Reserve is also undergoing renovations to expand their tiki bar, restaurant and a new clubhouse interior design estimated to be completed in March of 2026. Ideally located just 20 minutes from Naples' white-sand beaches and the Fifth Avenue South, 15 minutes to Marco Island and minutes to shopping, dining, and I-75, this home offers a rare opportunity to experience Southwest Florida living at its finest, without compromise. Your winter sanctuary awaits!

Please contact the owner for additional inforamtion.
14769 Windward Ln, Naples, FL 34114 is a 3 bedroom, 5 bathroom, 2,585 sqft single-family home. It last sold for $525,000 on Nov 3, 2020 (6,076% above the $8,500 asking price). More recently, it was listed as a rental in December 2025 with an asking price of $8,500 per month. That rental listing was removed on January 19, 2026. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $887,800, with a rent estimate of $5,524/month.

Home Details for 14769 Windward Ln

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: Central AirHeating Fuel: Forced Air
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher
Levels, Entrance, & Accessibility
Floors: Tile

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 6 MonthAvailable: now

Exterior Features

Parking & Garage
GarageParking: Attached Garage, On Site

Comparable Sales for 14769 Windward Ln

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
14531 Manchester Dr, Naples, FL
0.17
Single-Family Home
$580,000
11/14/25
3
2.5
1,980 sqft
14752 Windward Ln, Naples, FL
0.06
Single-Family Home
$1,349,000
12/18/25
3
3.5
3,144 sqft
14503 Manchester DR, Naples, FL
0.16
Single-Family Home
$570,000
08/20/26
4
2.5
2,248 sqft
14748 Windward LN, Naples, FL
0.06
Single-Family Home
$1,065,000
05/27/26
4
5
3,164 sqft
14878 Windward LN, Naples, FL
0.22
Single-Family Home
$920,000
06/09/26
3
2.5
2,344 sqft
14653 Tropical DR, Naples, FL
0.32
Single-Family Home
$639,900
09/08/25
3
2.5
2,039 sqft
14741 Leeward Dr, Naples, FL
0.17
Single-Family Home
$775,000
11/04/25
3
2
2,066 sqft
14776 Spinnaker Way, Naples, FL
0.25
Single-Family Home
$1,400,000
06/03/26
3
3.5
2,896 sqft
14439 Manchester DR, Naples, FL
0.28
Single-Family Home
$450,000
05/12/26
3
2
2,084 sqft
14558 Manchester DR, Naples, FL
0.25
Single-Family Home
$595,000
02/27/26
3
2
1,760 sqft

Nearby homes

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Rental Market Trends in Naples

Last updated Sep 2026
Trulia Rent Estimate$5,524/mo
Average rent
$5.5K
$250MoM
Available listings
3987
View rental market trends in Naples, FL

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

Price and Tax history

DateEventPrice
Jan 19, 2026
Source: Zillow Rentals
ListingRemoved
$8,500
Dec 23, 2025
Source: Zillow Rentals
Listed For Rent
$8,500
Nov 3, 2020
Source: N/A
Sold
$525,000
Aug 3, 2020
Source: Agent Provided
Pending
$549,900
Mar 3, 2020
Source: Agent Provided
PriceChange
$549,900
Price decreased by 4%

Frequently asked questions about 14769 Windward Ln

  • What is 14769 Windward Ln estimated to be worth?
    Trulia's estimated value for 14769 Windward Ln in Naples, FL is $887,800.
  • What is the price history for 14769 Windward Ln?
    14769 Windward Ln in Naples, FL last sold for $525,000 in November 2020.
  • 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 14769 Windward Ln have air conditioning?
    Yes, 14769 Windward Ln in Naples, FL has air conditioning.
  • Does 14769 Windward Ln have laundry facilities?
    Yes, 14769 Windward Ln in Naples, FL has in-unit laundry.

Homes for rent near 14769 Windward Ln

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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