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

$715,300

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,285 sqft

29 Madison Dr, Naples, FL 34110

Est. Refi. Payment $4,349/mo*
Refinance Your Home
Currently Off Market - Sold Jan 4, 2010 for $309,000

Home Value

Trulia Estimate
$715K
Since last month
Increased$6K (+0.9%)
Since last year
Decreased$6K (-0.8%)
Since last sale
Increased$407K (+131.6%)
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 +51% in the last 10 years
MonthEstimated value
2026
August 2026$716K
August 2026$715K
July 2026$710K
June 2026$707K
May 2026$702K
April 2026$729K
March 2026$727K
February 2026$735K
January 2026$727K
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
302 Sawgrass CT, Naples, FL
0.11
Single-Family Home
$665,000
08/24/26
4
2
2,341
39 Mentor DR, Naples, FL
0.12
Single-Family Home
$659,000
11/24/25
3
2
2,049
297 Sawgrass CT, Naples, FL
0.07
Single-Family Home
$759,000
04/15/26
4
3
2,250
60 MENTOR DRIVE, Naples, FL
0.19
Single-Family Home
$492,000
01/02/26
3
2
1,452
101 Heritage Way, Naples, FL
0.30
Single-Family Home
$550,000
09/15/25
4
2
2,174
89 Kirtland Dr, Naples, FL
0.17
Single-Family Home
$629,000
12/15/25
3
2
1,709
16129 Parque LN, Naples, FL
0.37
Single-Family Home
$890,000
04/20/26
4
2
2,109
16144 Parque LN, Naples, FL
0.33
Single-Family Home
$690,000
03/12/26
3
2
2,000
30 Wickliffe DR, Naples, FL
0.36
Single-Family Home
$612,000
01/15/26
3
2
1,884
49 Willoughby Dr, Naples, FL
0.26
Single-Family Home
$650,000
10/22/25
3
2
1,558

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
297 Sawgrass CT, Naples, FL 34110
0.07
$759,000
4
3
2,250
Recently Sold
54 Madison DR, Naples, FL 34110
0.10
$532,800
3
2
1,275
Off Market
38 HERITAGE WAY, Naples, FL 34110
0.10
$885,500
4
3
2,234
Off Market
302 Sawgrass CT, Naples, FL 34110
0.11
$665,000
4
2
2,341
Recently Sold
75 Kirtland DR, Naples, FL 34110
0.14
$631,000
3
2
1,462
Off Market
39 Mentor DR, Naples, FL 34110
0.12
$659,000
3
2
2,049
Recently Sold
35 Heritage WAY, Naples, FL 34110
0.13
$924,200
4
3
2,291
Off Market
88 Erie DR, Naples, FL 34110
0.17
$555,900
3
2
1,436
Off Market
20 Heritage WAY, Naples, FL 34110
0.13
$749,900
4
2
2,013
For Sale
89 Kirtland Dr, Naples, FL 34110
0.17
$629,000
3
2
1,709
Recently Sold
92 Madison DR, Naples, FL 34110
0.19
$817,600
5
3
2,047
Off Market
72 Heritage WAY, Naples, FL 34110
0.20
$761,700
3
2
2,016
Off Market

Local Information

  • Map ViewExplore the area around 29 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
2001
Living Area
2,285 sqft
Price/Sqft
$313

About this House

OPEN HOUSE DAILY! Come on By! This is an incredible opportunity to own a beautiful pool home at an unbelievable price! Featuring 4 bedrooms with a convenient split floorplan, 2 full baths, open kitchen into a spacious family room, darling breakfast nook overlooking the pool, formal dining area, formal living area, 4 sets of 6' sliding doors surrounding the pool and oversized 2 car garage. This home is in immaculate condition and is located in a quiet residential area. Pool backs to a private preserve and is surrounded by hibiscus hedges for ultimate privacy. Close to shopping, freeway access and 3 miles to Delnor Wiggins State Park. Excellent financing available. Realtors please see remarks.
29 Madison Dr, Naples, FL 34110 is a 4 bedroom, 2 bathroom, 2,285 sqft single-family home built in 2001. It last sold for $309,000 on Jan 4, 2010. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $715,300, with a rent estimate of $4,129/month.

Home Details for 29 Madison Dr

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Property Information

Year Built
Year Built: 2001Year Updated: 2001
Property Type / Style
Property Type: Single Family Home

Exterior Features

Exterior Home Features
Deck
Pool
Pool

Community

Units in Building: 1

Lot Information

Lot Area: 8712 sqft

Price and Tax history

DateEventPrice
Jan 4, 2010
Source: N/A
Sold
$309,000
Nov 25, 2009
Source: Agent Provided
PriceChange
$339,900
Price decreased by 0%
Nov 4, 2009
Source: Agent Provided
PriceChange
$341,500
Price increased by 1%
Nov 3, 2009
Source: Agent Provided
Listed For Sale
$339,500
Mar 7, 2001
Source: N/A
Sold
$69,900

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 29 Madison Dr

  • What is 29 Madison Dr estimated to be worth?
    Trulia's estimated value for 29 Madison Dr in Naples, FL is $715,300.
  • What is the price history for 29 Madison Dr?
    29 Madison Dr in Naples, FL last sold for $309,000 in January 2010.
  • 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 29 Madison Dr have a pool?
    Yes, 29 Madison Dr in Naples, FL has a pool.
  • How big is the lot at 29 Madison Dr?
    The lot at 29 Madison Dr in Naples, FL is about 0.20 acres (8,712 sq ft).

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