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

271 Madison Dr
Naples, FL 34110

  • 3 Beds
  • 2 Baths
  • 2,300 sqft

$652,200

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,931/mo*
Refinance Your Home

$652,200

Trulia Estimate
as of Aug 20, 2026
Est. Refi. Payment $3,931/mo*
Refinance Your Home
3 Beds
2 Baths
2,300 sqft

Home Value

Trulia Estimate
$652K
Since last month
Increased$400 (+0.1%)
Since last year
Increased$19K (+3%)
Since last sale
Increased$244K (+60.1%)
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 +81% in the last 10 years
MonthEstimated value
2026
August 2026$649K
July 2026$649K
June 2026$652K
May 2026$647K
April 2026$655K
March 2026$656K
February 2026$655K
January 2026$640K
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
261 Kirtland DR, Naples, FL
0.06
Single-Family Home
$700,000
05/29/26
3
2
1,942
380 Ashbury WAY, Naples, FL
0.18
Single-Family Home
$600,000
05/29/26
3
2
2,029
212 Willowick DR, Naples, FL
0.17
Single-Family Home
$545,000
02/13/26
3
2
1,655
208 Erie DR, Naples, FL
0.15
Single-Family Home
$710,000
11/07/25
3
2
1,758
248 Channing CT, Naples, FL
0.16
Single-Family Home
$745,000
07/10/26
4
2
2,352
272 Johnnycake DR, Naples, FL
0.23
Single-Family Home
$665,000
07/06/26
3
2
1,884
224 Channing CT, Naples, FL
0.22
Single-Family Home
$645,000
04/08/26
3
2
1,714
231 Johnnycake DR, Naples, FL
0.22
Single-Family Home
$607,000
10/27/25
3
2
1,597
404 Ashbury WAY, Naples, FL
0.24
Single-Family Home
$672,500
01/09/26
3
2
1,650
205 Madison DR, Naples, FL
0.17
Single-Family Home
$759,000
02/01/26
4
2
2,023

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
270 Madison DR, Naples, FL 34110
0.04
$769,000
3
2.5
1,986
For Sale
276 Madison DR, Naples, FL 34110
0.04
$546,400
3
2
1,265
Off Market
282 Madison DR, Naples, FL 34110
0.05
$662,700
3
2
1,686
Off Market
295 Saybrook CT, Naples, FL 34110
0.05
$712,800
3
2
1,924
Off Market
282 Saybrook CT, Naples, FL 34110
0.06
$853,000
3
3
2,290
Off Market
261 Kirtland DR, Naples, FL 34110
0.06
$700,000
3
2
1,942
Recently Sold
244 Erie DR, Naples, FL 34110
0.07
$750,000
4
4
2,464
Recently Sold
247 Erie DR, Naples, FL 34110
0.09
$593,100
2
2
1,261
Off Market
227 Kirtland DR, Naples, FL 34110
0.12
$712,300
3
2
2,164
Off Market
238 Willowick DR, Naples, FL 34110
0.13
$749,200
3
2
2,435
Off Market
223 Kirtland DR, Naples, FL 34110
0.14
$768,200
3
2
1,936
Off Market
243 Willowick Dr, Naples, FL 34110
0.14
$595,700
3
2
1,579
Off Market

Local Information

  • Map ViewExplore the area around 271 Madison Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1997
Living Area
2,300 sqft
Price/Sqft
$284
Parking
Garage

About this House

IF YOU'D LIKE TO SEE THIS HOME, PLEASE respond with MY Pre-appointment questions BELOW THE DESCRIPTION

UNFURNISHED ANNUAL RENTAL in Willoughby Acres! (NO HOA!)
High ceilings, Spacious rooms, ALL Brand New Kitchen with soft close cabinets and ALL new appliances. LED lighting and ceiling fans,
Master BR with walk-in closet and Jacuzzi tub, separate shower.
Laundry room w/ Brand New Washer & Dryer.
New Tile Flooring and New carpeting in the BRs.
Conveniently located to shopping, Oake's Farms, Jason's Deli, Sam's Club, Mercado, Beaches and Excellent Naples School District.
Offering 1 year lease with renewal option
Good Credit Required! Sorry No Pets, No Smoking.
Landscaping service included
At Contract: 1st mo Rent, Security Deposit
Rent reflects an On time - Early Discount

** ** IF YOU'D LIKE TO SEE THIS HOME, PLEASE RESPOND WITH THE PRE-APPOINTMENT QUESTIONS BELOW.

Name: ______________ ______________
Phone: ______________
# of People total: ______________
# of Adults: ______________
Intended lease term: ______________
Occupancy Date: ______________
# of Pets: ______________ What kind of Pets: ______________
Smoking: Y or N: ______________
How is your Credit: (Excellent, Good, Bad or Ugly) ______________
Landlord Reference? Y or N: ______________
Your occupation(s): ______________ ______________
Ever owned a home? Y or N: ______________

Offering 1 year lease with renewal option
** ** IF YOU'D LIKE TO SEE THIS HOME, PLEASE RESPOND WITH THE PRE-APPOINTMENT QUESTIONS BELOW.

Name: ______________ ______________
Phone: ______________
# of People total: ______________
# of Adults: ______________
Intended lease term: ______________
Occupancy Date: ______________
# of Pets: ______________ What kind of Pets: ______________
Smoking: Y or N: ______________
How is your Credit: (Excellent, Good, Bad or Ugly) ______________
Landlord Reference? Y or N: ______________
Your occupation(s): ______________ ______________
Ever owned a home? Y or N: ______________
271 Madison Dr, Naples, FL 34110 is a 3 bedroom, 2 bathroom, 2,300 sqft single-family home built in 1997. It last sold for $405,500 on Mar 26, 2020. More recently, it was listed as a rental in August 2022 with an asking price of $2,895 per month. That rental listing was removed on September 6, 2022. It is currently off market. The Trulia Estimate is $652,200, with a rent estimate of $3,832/month.

Home Details for 271 Madison Dr

Interior Features

Heating & Cooling
Heating: Forced AirHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile
Appliances & Utilities
DryerWasher

Property Information

Year Built
Year Built: 1997Year Updated: 1997
Property Type / Style
Property Type: Single Family Home

Exterior Features

Parking & Garage
GarageParking: Garage Detached, Off Street

Community

Units in Building: 1

Lot Information

Lot Area: 10454 sqft

Price and Tax history

DateEventPrice
Sep 6, 2022
Source: Zillow Rental Manager
ListingRemoved
Aug 31, 2022
Source: Zillow Rental Manager
Listed For Rent
$2,895
Nov 6, 2020
Source: Agent Provided
ListingRemoved
$2,375
Oct 21, 2020
Source: Agent Provided
PriceChange
$2,375
Price decreased by 5%
Aug 11, 2020
Source: Agent Provided
PriceChange
$2,495
Price decreased by 2%

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. "
    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

Frequently asked questions about 271 Madison Dr

  • What is 271 Madison Dr estimated to be worth?
    Trulia's estimated value for 271 Madison Dr in Naples, FL is $652,200.
  • What is the price history for 271 Madison Dr?
    271 Madison Dr in Naples, FL last sold for $405,500 in March 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 271 Madison Dr have laundry facilities?
    Yes, 271 Madison Dr in Naples, FL has in-unit laundry.
  • How big is the lot at 271 Madison Dr?
    The lot at 271 Madison Dr in Naples, FL is about 0.24 acres (10,454 sq ft).

Explore by feature - Pet Friendly

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Explore by feature - Outdoor Space

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Apartments for Rent

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Off Market Homes Near 271 Madison Dr

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