37 Willoughby Dr, Naples, FL 34110
Property image
65inch outdoor tv
OFF MARKET

$713,800

Trulia Estimate
as of Sep 17, 2026
  • 3 Beds
  • 2 Baths
  • 2,000 sqft

37 Willoughby Dr, Naples, FL 34110

Home Highlights

Single-Family Home
2,000 sqft
$357/sqft
Attached Garage

Local Information

  • Map ViewExplore the area around 37 Willoughby Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Snow birds dream home
Nov - April $10,888 per month
May - oct $4800 per month
pet friendly with fully fenced in gates with locks , massive resort style backyard. This Fully renovated 3 bedroom 2 full bath full baths
Finished all utilities, cable ,Wi-Fi included 65 inch led tv in living room 55 inch led tv in master bedroom Newley renovated resort style outdoor living area has 3500 sq ft of travertine with a 30 by 16 inground heated pool with all new high end outdoor furniture we also added a 65inch outdoor tv with 3000 sq ft of beautiful landscaping making this a full resort backyard Paradise. Front of the house was just re done with new extra wide driveway with pavers new landscaping as well this property is very close to all shopping like famous seed to table , Mercado & only 2.2 miles too the beach at Wiggins pass park

Snow bird dream Vacation rental or short term rental rates varies from $5000 to $10800 depends on month of the year longer leases available . cable , Wi-Fi , fully furniture & laundry all includes
37 Willoughby Dr, Naples, FL 34110 is a 3 bedroom, 2 bathroom, 2,000 sqft single-family home. It last sold for $700,000 on Nov 30, 2021 (13,900% above the $5,000 asking price). More recently, it was listed as a rental in April 2025 with an asking price of $5,000 per month. That rental listing was removed on May 16, 2025. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $713,800, with a rent estimate of $4,171/month.

Home Details for 37 Willoughby Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 MonthAvailable: now

Interior Features

Appliances & Utilities
DishwasherDryerWasher
Heating & Cooling
Air ConditioningCooling System: Central Air

Exterior Features

Pool
Pool
Parking & Garage
Parking: Attached Off Street, On Site

Comparable Sales for 37 Willoughby Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
49 Willoughby Dr, Naples, FL
0.05
Single-Family Home
$650,000
10/22/25
3
2
1,558 sqft
39 Mentor DR, Naples, FL
0.13
Single-Family Home
$659,000
11/24/25
3
2
2,049 sqft
30 Wickliffe DR, Naples, FL
0.15
Single-Family Home
$612,000
01/15/26
3
2
1,884 sqft
302 Sawgrass CT, Naples, FL
0.15
Single-Family Home
$665,000
08/24/26
4
2
2,341 sqft
89 Kirtland Dr, Naples, FL
0.23
Single-Family Home
$629,000
12/15/25
3
2
1,709 sqft
60 MENTOR DRIVE, Naples, FL
0.12
Single-Family Home
$492,000
01/02/26
3
2
1,452 sqft
92 Chardon PL, Naples, FL
0.22
Single-Family Home
$550,000
10/17/25
3
2
1,642 sqft
157 Willoughby DR, Naples, FL
0.33
Single-Family Home
$710,000
06/24/26
3
2
1,668 sqft
133 Wickliffe DR, Naples, FL
0.27
Single-Family Home
$753,000
06/25/26
3
3
1,790 sqft
104 Johnnycake DR, Naples, FL
0.20
Single-Family Home
$520,000
04/09/26
2
2
1,744 sqft

Nearby homes

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Rental Market Trends in Naples

Last updated Sep 2026
Trulia Rent Estimate$4,171/mo
Average rent
$5.5K
Available listings
3949
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.
  • 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."
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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
    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
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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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  • 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
    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
May 16, 2025
Source: Zillow Rentals
ListingRemoved
$5,000
Apr 25, 2025
Source: Zillow Rentals
Listed For Rent
$5,000
Nov 25, 2024
Source: Zillow Rentals
ListingRemoved
$10,888
Oct 5, 2024
Source: Zillow Rentals
PriceChange
$10,888
Price increased by 142%
Sep 6, 2024
Source: Zillow Rentals
PriceChange
$4,500
Price decreased by 67%

Frequently asked questions about 37 Willoughby Dr

  • What is 37 Willoughby Dr estimated to be worth?
    Trulia's estimated value for 37 Willoughby Dr in Naples, FL is $713,800.
  • What is the price history for 37 Willoughby Dr?
    37 Willoughby Dr in Naples, FL last sold for $700,000 in November 2021.
  • 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 37 Willoughby Dr have air conditioning?
    Yes, 37 Willoughby Dr in Naples, FL has air conditioning.
  • Does 37 Willoughby Dr have a pool?
    Yes, 37 Willoughby Dr in Naples, FL has a pool.

Homes for rent near 37 Willoughby Dr

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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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