1444 HEMINGWAY PL, Naples, FL 34103
Property image
Property image
OFF MARKET

$3,242,700

Trulia Estimate
  • 5 Beds
  • 5.5 Baths
  • 4,731 sqft (on 0.26 acres)

1444 HEMINGWAY PL, Naples, FL 34103

Est. Refi. Payment $19,539/mo*
Refinance Your Home
Currently Off Market - Sold Feb 20, 2024 for $3,000,000

Home Value

Trulia Estimate
$3.24M
Since last month
Increased$25K (+0.8%)
Since last year
Increased$479K (+17.3%)
Since last sale
Increased$241K (+8%)
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 +119% in the last 10 years
MonthEstimated value
2026
August 2026$3.24M
August 2026$3.24M
July 2026$3.22M
June 2026$3.17M
May 2026$3.17M
April 2026$3.14M
March 2026$3.09M
February 2026$3.15M
January 2026$3.05M
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
1408 Hemingway PL, Naples, FL
0.14
Single-Family Home
$1,900,000
09/11/25
4
4.5
4,098
1086 Michigan Ave, Naples, FL
0.18
Single-Family Home
$2,458,113
11/14/25
3
5
4,218
667 Binnacle DR, Naples, FL
0.60
Single-Family Home
$3,500,000
07/24/26
5
4.5
4,120
1381 Trail Terrace DR, Naples, FL
0.31
Single-Family Home
$1,870,000
08/12/26
4
3.5
2,828
3353 Binnacle DR, Naples, FL
0.53
Single-Family Home
$5,500,000
02/03/26
4
5
3,972
745 Riviera DR, Naples, FL
0.60
Single-Family Home
$5,520,000
03/17/26
4
4.5
4,912
696 Fountainhead LN, Naples, FL
0.60
Single-Family Home
$5,500,000
01/20/26
4
4.5
3,805
1136 Trail Terrace DR, Naples, FL
0.26
Single-Family Home
$1,600,000
01/07/26
3
3.5
2,340
645 Park Shore DR, Naples, FL
0.66
Single-Family Home
$2,925,000
10/24/25
4
3.5
3,336

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
1248 Frank Whiteman BLVD, Naples, FL 34103
0.06
$675,000
3
2
1,490
For Sale
1315 Frank Whiteman BLVD, Naples, FL 34103
0.06
$615,600
2
1
1,025
Off Market
1148 Frank Whiteman BLVD, Naples, FL 34103
0.10
$573,100
2
2
1,180
Off Market
1139 Frank Whiteman BLVD, Naples, FL 34103
0.09
$550,000
2
1
950
For Sale
1200 Cypress Woods DR, Naples, FL 34103
0.07
$1,836,100
3
2
2,156
Off Market
1254 Cooper Dr, Naples, FL 34103
0.13
$674,400
3
1.5
1,634
Off Market
1236 Cooper DR, Naples, FL 34103
0.13
$470,000
2
1
840
Recently Sold
1419 Hemingway PL, Naples, FL 34103
0.10
$2,941,100
4
4.5
4,122
Off Market
1132 Cypress Woods DR, Naples, FL 34103
0.10
$973,900
3
2
1,293
Off Market
1255 Illinois DR, Naples, FL 34103
0.15
$710,000
3
2
1,334
Recently Sold
1105 Hollygate LN, Naples, FL 34103
0.12
$4,250,000
6
6
4,674
For Sale

Local Information

  • Map ViewExplore the area around 1444 HEMINGWAY PL.
  • Schools2 Preschool Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2005
0.26 acre lot
4,731 sqft
$685/sqft
2 Car Garage
HOA $733/mo

About this House

Enjoy the modern elegance of this custom two-story home in exclusive Hemingway place. The chef's kitchen features, an oversized island with bar seating, gas cooktop & oven, gorgeous counters, & built-in breakfast nook. Modern design & decor can be found throughout, including high ceilings, gorgeous wood flooring, and unique architectural accents. Master retreat, features, custom closets & spa like bathroom ideal for relaxation. The well laid out floor plan allows easy access from the interior living space to the private courtyard, pool & outdoor living area. Open balconies with a variety of seating showcase, the relaxing atmosphere of this unique property. A separate stairway leads to another bedroom/bath, which is perfect for guests. Major updates for this property include new HVAC units 2013 w/thermostats in 2022, bath remodel 2013, new appliances 2016, pool renovation 2019, hot water heaters 2013/2014, generator 2020, exterior painting 2021, & replacement of central vac, sealing garage floors & garage cabinetry 2022. Ideally located off of Goodlette Road just a short drive to downtown Naples fine dining, world-class, shopping, entertainment, and white sand beaches.
1444 HEMINGWAY PL, Naples, FL 34103 is a 5 bedroom, 6 bathroom, 4,731 sqft single-family home built in 2005. It last sold for $3,000,000 on Feb 20, 2024 (8% below the $3,250,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $3,242,700.
Last check for updates: about 10 hours ago
Listed by Dante DiSabato, LLC, (239) 537-5351
William Raveis Real Estate
Bought with: Diane Landgren, (708) 975-7258, Downing Frye Realty Inc.
Originating MLS: Naples
Source: SWFLMLS, MLS#223029845

Home Details for 1444 HEMINGWAY PL

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Bedroom, Dining Room, Kitchen
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4731 Square Feet
Appliances & Utilities
Appliances: Dishwasher, Disposal, Dryer, Microwave, Range, Refrigerator/Freezer, Self Cleaning Oven, WasherDishwasherDisposalDryerLaundry: Inside,Laundry TubMicrowaveWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Ceiling Fan(s),Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Spa: In Ground, Concrete, Equipment Stays, Heated, Pool Bath, Pool IntegratedHas a FireplaceHas a Spa
Gas & Electric
Gas: Propane
Windows, Doors, Floors & Walls
Window: Window Coverings, Impact Resistant Windows, Storm Protection (Other)Door: French Doors, Impact Resistant DoorsFlooring: Concrete, Tile
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Concrete, Tile
View
Has a ViewView: Pool/Club
Security
Security: Security System, Smoke Detector(s), Gated Community

Exterior Features

Exterior Home Features
Roof: TileFencing: FencedFoundation: Concrete BlockHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached
Pool
Pool: Pool/Spa Combo, In Ground, Concrete, Custom Upgrades, Equipment Stays, Gas Heat, Pool BathPool
Frontage
Waterfront: NoneNot on Waterfront
Farm & Range
Not Allowed to Raise Horses

Property Information

Year Built
Year Built: 2005
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: HouseArchitecture: House
Building
Building: DSL/Cable AvailableConstruction Materials: Block, StuccoNot a New Construction
Property Information
Parcel Number: 49520000402

Price & Status

Price
List Price: $3,250,000
Status Change & Dates
Off Market Date: Tue Feb 20 2024

Active Status

MLS Status: Closed

Media

Location

Direction & Address
City: NAPLESCommunity: HEMINGWAY PLACE
School Information
Elementary School: SEA GATE ELEMENTARYJr High / Middle School: GULFVIEW MIDDLE SCHOOLHigh School: NAPLES HIGH SCHOOL

Building

Building Area
Building Area: 6499 Square Feet

Community

Community Features: Sidewalks, GatedNot Senior Community

HOA

Association for this Listing: NaplesNo HOAHOA Fee: $8,800/Annually

Lot Information

Lot Area: 0.26 acres

Offer

Contingencies: Inspection

Rental Terms, Policies & Fees

Furnished

Miscellaneous

Mls Number: 223029845

Additional Information

HOA Amenities: Play Area,Sidewalk

Price and Tax history

DateEventPrice
Feb 20, 2024
Source: SWFLMLS #223029845
Sold
$3,000,000
Jan 16, 2024
Source: SWFLMLS #223029845
Pending
$3,250,000
Oct 23, 2023
Source: SWFLMLS #223029845
Listed For Sale
$3,250,000
Aug 1, 2023
Source: William Raveis Real Estate, Mortgage & Insurance
ListingRemoved
Jun 21, 2023
Source: SWFLMLS #223029845
PriceChange
$3,295,000
Price decreased by 6%

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 "
    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."
    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

The source of this real property information is the copyrighted and proprietary database compilation of the Southwest Florida MLS. Copyright 2026 Southwest Florida MLS. All rights reserved. The accuracy of this information is not warranted or guaranteed. This information should be independently verified if any person intends to engage in a transaction in reliance upon it.

Frequently asked questions about 1444 HEMINGWAY PL

  • What is 1444 HEMINGWAY PL estimated to be worth?
    Trulia's estimated value for 1444 HEMINGWAY PL in Naples, FL is $3,242,700.
  • What is the price history for 1444 HEMINGWAY PL?
    1444 HEMINGWAY PL in Naples, FL last sold for $3,000,000 in February 2024.
  • 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 1444 HEMINGWAY PL have air conditioning?
    Yes, 1444 HEMINGWAY PL in Naples, FL has air conditioning.
  • Does 1444 HEMINGWAY PL have a pool?
    Yes, 1444 HEMINGWAY PL in Naples, FL has a pool.

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