265 Madison Dr, Naples, FL 34110
Property image
Property image
OFF MARKET

265 Madison Dr
Naples, FL 34110

  • 3 Beds
  • 2.5 Baths
  • 1,700 sqft

$540,900

Trulia Estimate
as of Aug 21, 2026

$540,900

Trulia Estimate
as of Aug 21, 2026
  • 3 Beds
  • 2.5 Baths
  • 1,700 sqft

Home Highlights

Property Type
Single-Family Home
Living Area
1,700 sqft
Price/Sqft
$318
Parking
Attached Garage

Local Information

  • Map ViewExplore the area around 265 Madison Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Beautiful 3 bedroom 2 1/2 bath home. Southern exposure! Completely remodeled. Impact windows and doors. New beautiful landscaping. New kitchen, new floors, new interior doors and so much more. Walk in closet in the master suite.

Flexible
265 Madison Dr, Naples, FL 34110 is a 3 bedroom, 3 bathroom, 1,700 sqft single-family home. It last sold for $280,000 on Jul 17, 2007 (7,900% above the $3,500 asking price). More recently, it was listed as a rental in April 2025 with an asking price of $3,800 per month. That rental listing was removed on June 2, 2025. It is currently off market. The Trulia Estimate is $540,900, with a rent estimate of $3,042/month.

Home Details for 265 Madison Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: 1 Year

Interior Features

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

Exterior Features

Parking & Garage
Parking: Attached, On Site

Comparable Sales for 265 Madison Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
212 Willowick DR, Naples, FL
0.16
Single-Family Home
$545,000
02/13/26
3
2
1,655 sqft
261 Kirtland DR, Naples, FL
0.06
Single-Family Home
$700,000
05/29/26
3
2
1,942 sqft
208 Erie DR, Naples, FL
0.14
Single-Family Home
$710,000
11/07/25
3
2
1,758 sqft
231 Johnnycake DR, Naples, FL
0.21
Single-Family Home
$607,000
10/27/25
3
2
1,597 sqft
380 Ashbury WAY, Naples, FL
0.18
Single-Family Home
$600,000
05/29/26
3
2
2,029 sqft
224 Channing CT, Naples, FL
0.22
Single-Family Home
$645,000
04/08/26
3
2
1,714 sqft
404 Ashbury WAY, Naples, FL
0.24
Single-Family Home
$672,500
01/09/26
3
2
1,650 sqft
272 Johnnycake DR, Naples, FL
0.23
Single-Family Home
$665,000
07/06/26
3
2
1,884 sqft
205 Madison DR, Naples, FL
0.15
Single-Family Home
$759,000
02/01/26
4
2
2,023 sqft
258 Willoughby Drive Ext, Naples, FL
0.35
Single-Family Home
$610,000
07/13/26
3
2.5
1,613 sqft

Nearby homes

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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
Jun 2, 2025
Source: Zillow Rentals
ListingRemoved
$3,500
May 12, 2025
Source: Zillow Rentals
PriceChange
$3,500
Price decreased by 8%
Apr 24, 2025
Source: Zillow Rentals
Listed For Rent
$3,800
Mar 15, 2010
Source: Agent Provided
ListingRemoved
$270,000
Feb 27, 2010
Source: Agent Provided
Listed For Sale
$270,000

Frequently asked questions about 265 Madison Dr

  • What is 265 Madison Dr estimated to be worth?
    Trulia's estimated value for 265 Madison Dr in Naples, FL is $540,900.
  • What is the price history for 265 Madison Dr?
    265 Madison Dr in Naples, FL last sold for $280,000 in July 2007.
  • 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 265 Madison Dr have air conditioning?
    Yes, 265 Madison Dr in Naples, FL has air conditioning.
  • Does 265 Madison Dr have laundry facilities?
    Yes, 265 Madison Dr in Naples, FL has in-unit laundry.

Homes for rent near 265 Madison 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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