101 Courtside Dr, Naples, FL 34105
Property image
Property image
OFF MARKET

$356,000

Trulia Estimate
  • 2 Beds
  • 2 Baths
  • 1,169 sqft

101 Courtside Dr, Naples, FL 34105

Est. Refi. Payment $2,197/mo*
Refinance Your Home
Currently Off Market - Sold Mar 3, 2016 for $185,000

Home Value

Trulia Estimate
$356K
Since last month
Decreased$2K (-0.4%)
Since last year
Decreased$500 (-0.1%)
Since last sale
Increased$172K (+93%)
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 +89% in the last 10 years
MonthEstimated value
2026
August 2026$357K
August 2026$356K
July 2026$359K
June 2026$355K
May 2026$362K
April 2026$356K
March 2026$362K
February 2026$365K
January 2026$359K
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
301 Courtside DR, Naples, FL
0.03
Condo
$425,000
04/29/26
2
2
1,282
203 Courtside DR #B103, Naples, FL
0.02
Condo
$430,000
05/01/26
2
2
1,421
401 Courtside DR #D101, Naples, FL
0.02
Condo
$485,000
05/01/26
2
2
1,282
200 Wyndemere WAY #B302, Naples, FL
0.12
Condo
$475,000
02/24/26
2
2
1,651
300 Wyndemere Way #C104, Naples, FL
0.10
Condo
$545,000
03/18/26
2
2
1,786
114 Amblewood LN, Naples, FL
0.11
Condo
$750,000
03/24/26
2
2
1,700
400 Wyndemere WAY #D102, Naples, FL
0.11
Condo
$698,000
03/03/26
2
2
1,786
163 Amblewood LN #4-404, Naples, FL
0.14
Condo
$760,000
02/19/26
2
2
1,550
161 Amblewood Ln, Naples, FL
0.11
Condo
$950,000
05/28/26
2
2
1,700
101 Amblewood LN #1-104, Naples, FL
0.06
Condo
$720,000
07/01/26
3
2
1,792

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
204 Courtside DR #B-104, Naples, FL 34105
0.01
$422,800
2
2
1,225
Off Market
301 Courtside DR, Naples, FL 34105
0.03
$425,000
2
2
1,282
Recently Sold
203 Courtside DR #B103, Naples, FL 34105
0.02
$430,000
2
2
1,421
Recently Sold
207 Courtside DR #B203, Naples, FL 34105
0.03
$484,900
2
2
1,421
Off Market
406 Courtside DR #D201, Naples, FL 34105
0.02
$407,300
2
2
1,225
Off Market
401 Courtside DR #D101, Naples, FL 34105
0.02
$485,000
2
2
1,282
Recently Sold
506 Courtside DR #E201, Naples, FL 34105
0.04
$440,000
2
2
1,325
For Sale
504 Courtside DR #E104, Naples, FL 34105
0.05
$476,400
3
2
1,351
Off Market
408 Courtside DR #D203, Naples, FL 34105
0.04
$446,800
2
2
1,450
Off Market
601 Courtside DR #F101, Naples, FL 34105
0.06
$414,900
2
2
1,225
Off Market
104 Courtside DR #A104, Naples, FL 34105
0.05
$454,500
2
2
1,550
Off Market
606 Courtside DR #F201, Naples, FL 34105
0.07
$358,500
2
2
1,225
Off Market

Local Information

  • Map ViewExplore the area around 101 Courtside Dr.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Condo
Built in 1985
1,169 sqft
$305/sqft

About this House

ONE OF A KIND! Lovely completely updated 2 bedroom 2 baths end unit that lives like a villa with private entrance and no one above. Granite kitchen counters, wood flooring, spacious screened in porch for outdoor living, custom paint and custom closets, beautifully maintained and ready for new owner. WYNDEMERE is one of the most sought after golfing communities in the area with state of the art amenities like a new resort style swimming pool complex and popular fitness center plus a newly renovated fabulous Clubhouse. Social Membership is required. (See confidential information!)
101 Courtside Dr, Naples, FL 34105 is a 2 bedroom, 2 bathroom, 1,169 sqft condo built in 1985. It last sold for $185,000 on Mar 3, 2016. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $356,000.

Home Details for 101 Courtside Dr

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Interior Details
Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Carpet, Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: WoodGardenPatioPorch
Parking & Garage
Parking Space: 1

Property Information

Year Built
Year Built: 1985Year Updated: 1985
Property Type / Style
Property Type: CondoArchitecture: Other

Rental Terms, Policies & Fees

Furnished

Community

Units in Building: 10

Additional Information

On Site Laundry Available

Building

Fitness & Sports
Tennis Court

Price and Tax history

DateEventPrice
Mar 3, 2016
Source: N/A
Sold
$185,000
May 27, 2015
Source: Agent Provided
ListingRemoved
$129,500
May 14, 2014
Source: Agent Provided
Listed For Sale
$129,500
Oct 1, 2010
Source: N/A
Sold
$127,000
Aug 9, 2004
Source: N/A
Sold
$120,000

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. "
    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 "
    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

Frequently asked questions about 101 Courtside Dr

  • What is 101 Courtside Dr estimated to be worth?
    Trulia's estimated value for 101 Courtside Dr in Naples, FL is $356,000.
  • What is the price history for 101 Courtside Dr?
    101 Courtside Dr in Naples, FL last sold for $185,000 in March 2016.
  • 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 101 Courtside Dr have air conditioning?
    Yes, 101 Courtside Dr in Naples, FL has air conditioning.
  • Does 101 Courtside Dr have laundry facilities?
    Yes, 101 Courtside Dr in Naples, FL has in-unit laundry.

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Off Market Homes Near 101 Courtside Dr

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Homes for sale near 101 Courtside Dr

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