1444 E Winchester Ave, Labelle, FL 33935
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Property image
FOR SALE
3D VIEW
3.02 ACRES

1444 E Winchester Ave
Labelle, FL 33935

  • 6 Beds
  • 5.5 Baths
  • 5,176 sqft (on 3.02 acres)

$1,169,000

Est. Mortgage $7,747/mo*
Get Pre-Qualified

$1,169,000

Est. Mortgage $7,747/mo*
Get Pre-Qualified
6 Beds
5.5 Baths
5,176 sqft
(on 3.02 acres)

Home Highlights

Parking
3 Car Garage
Outdoor
Porch, Patio, Pool
HOA
None
Price/Sqft
$226
Climate Control
Central, Electric & Central Air, Ceiling Fans
Listed
180+ days ago

Local Information

  • Map ViewExplore the area around 1444 E Winchester Ave.
  • Schools2 Preschool Schools2 Elementary Schools3 Middle Schools3 High Schools
  • Shop & Eat
-- mins to
Commute Destination

About this House

*Recently reduced by $20,000. Seller is motivated and will consider all offers from qualified buyers.*

Luxury meets country charm within this Exceptional 3.02-Acre gated estate in LaBelle, Florida!
Welcome to this rare multi-residence property offering over 5000 Sq ft of living space across the main home, guest house, and garage apartment. The two-story main home features cathedral ceilings, a beautiful eat in kitchen with stainless steel appliances and a stunning floor to ceiling fireplace. Eating dinner in the formal dining room with the beautiful views from the surrounding windows will make family dinners unforgettable. Step into a breathtaking master suite designed for both comfort and style. This spacious retreat features a private bathroom with a separate soaking tub and shower, custom-designed closet with ample storage, built-ins, and useful finishes to keep your wardrobe organized and accessible. The suite also boasts a dual-sided fireplace, thoughtfully engineered to open to both the bedroom and the living room, creating a warm, inviting atmosphere and a seamless flow between spaces. The 2 story Guest house features a full kitchen, large family room, 2 bedrooms and downstairs bath. The extra apartment provides 1 bedroom, 1 bath, and a full kitchen above a 3-car garage with workshop/gym. Enjoy resort-style outdoor living with a saltwater pool, triple waterfall, and screened lanai connecting to the main house with a paver walk way. Nestled on the property is a charming shed-style building, perfect as a home office, creative studio, or “she shed.” Its cozy yet functional layout offers a private retreat, ideal for focused work, hobbies, or quiet relaxation. With its quaint design and versatile space, it adds both character and utility to the property, providing a peaceful escape right in your backyard. The property is fully fenced with dual electric gates, surrounded by beautiful mature oak trees, and includes a 3 bay pole barn with separate areas for different animals near by. The large fenced in side yard is suitable for horses. Perfect for multi-generational living, entertaining, or income potential, this estate combines privacy, luxury, and versatility in one of LaBelle’s most desirable Communities "The Ranchettes"!
Last check for updates: about 1 hour ago
Listing courtesy of Maureen Creagh, (863) 233-1847
Weatherford Realty Group LLC
Originating MLS: Florida Gulf Coast
Source: Florida Gulf Coast MLS, MLS#2025009608
Also Listed on Florida Gulf Coast MLS.

Home Details for 1444 E Winchester Ave

Active Status

MLS Status: Active

Interior Features

Beds & Baths
Number of Bedrooms: 6Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5176 Square Feet
Appliances & Utilities
Utilities: Cable Not Available, High Speed Internet Available, Underground UtilitiesAppliances: Dishwasher, Freezer, Microwave, Range, Refrigerator, Self Cleaning Oven, Tankless Water Heater, Warming Drawer, Water Softener, Water PurifierDishwasherLaundry: Washer Hookup,Dryer Hookup,Inside,In Garage,Laundry TubMicrowaveRefrigerator
Heating & Cooling
Heating: Central,Electric,Wall FurnaceHas CoolingAir Conditioning: Central Air,Ceiling Fan(s),Electric,Wall Unit(s)Has HeatingHeating Fuel: Central
Fireplace & Spa
Has a FireplaceNo Spa
Windows, Doors, Floors & Walls
Window: Impact Glass, Shutters, Window CoveringsDoor: French DoorsFlooring: Carpet, Tile, Wood
Levels, Entrance, & Accessibility
Stories: 2Number of Stories: 2Levels: TwoFloors: Carpet, Tile, Wood
View
Has a ViewView: Landscaped, Pool, Trees/Woods
Security
Security: Fenced, Secured Garage/Parking, Security System, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: MetalPatio / Porch: Lanai, Open, Patio, Porch, ScreenedOther Structures: Apartment, Barn(s), OutbuildingExterior: Fence, Fruit Trees, Security/High Impact Doors, Sprinkler/Irrigation, Patio, StorageHas a Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Attached,Circular Driveway,Driveway,Garage,Guest,Paved,RV Access/Parking,Two Spaces,Garage Door Opener
Pool
Pool: Concrete, Electric Heat, Heated, Pool Equipment, Pool Sweep, Screen Enclosure, Salt WaterPool
Frontage
Waterfront: NoneResponsible for Road Maintenance: Public Maintained RoadRoad Surface Type: PavedNot on Waterfront
Water & Sewer
Sewer: Septic Tank
Farm & Range
Horse Amenities: Horses AllowedAllowed to Raise Horses

Days on Market

Cumulative Days on Market: 262Days on Market: 180+

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Two Story
Building
Construction Materials: Vinyl Siding, Wood Frame
Property Information
Condition: ResaleParcel Number: S25422900100060150

Price & Status

Price
List Price: $1,169,000Price Per Sqft: $226
Status Change & Dates
Possession Timing: Close Of Escrow

Media

Location

Direction & Address
City: LabelleCommunity: RANCHETTES
School Information
Elementary School: West GladesJr High / Middle School: Labelle Middle SchoolHigh School: Labelle High School

Agent Information

Listing Agent
Listing ID: 2025009608

Building

Building Area
Building Area: 7197 Square Feet

Community

Community Features: Non-Gated, Street LightsNot Senior CommunityUnits in Building: 3

HOA

HOA Fee Includes: NoneHOA Phone: 863-675-3903HOA Fee (second): 60HOA Fee Frequency (second): AnnuallyAssociation for this Listing: Florida Gulf CoastHas an HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 3.02 Acres

Offer

Listing Terms: All Financing Considered, Cash

Business

Business Information
Ownership: Single Family

Miscellaneous

Mls Number: 2025009608Living Area Range Units: Square FeetAttic: Pull Down StairsAbove Grade Unfinished Area Units: Square FeetBelow Grade Unfinished Area Units: Square FeetUniversal Property Id: US-12043-N-S25422900100060150-R-N

Additional Information

HOA Amenities: Guest Suites,Hobby RoomSource Internet Entire Listing Display

Around this home

What Locals Say about Labelle

At least 62 Trulia users voted on each feature.

  • 89 % Say parking is easy

  • 89 % Say car is needed

  • 88 % Say yards are well-kept

  • 81 % Say it's dog friendly

  • 76 % Say there's holiday spirit

  • 72 % Say it's quiet

  • 69 % Say kids play outside

  • 60 % Say people would walk alone at night

  • 59 % Say there's wildlife

  • 58 % Say neighbors are friendly

  • 55 % Say they plan to stay for at least 5 years

  • 43 % Say streets are well-lit

  • 41 % Say it's walkable to grocery stores

  • 36 % Say there are community events

  • 35 % Say there are sidewalks

  • 33 % Say it's walkable to restaurants

Sourced by Trulia users. Learn more about our methodology.
  • Angell Zamarripa
    "Neighborhood is calm and everyone is very friendly, you feel safe enough to go on walks with your dog without fear"
    0
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  • Saray Lopez
    "The cabbage festivals each year is a great way the community gets together to unite small businesses and have a celebration of the town. "
    0
    Flag
  • Donna G.
    "It’s not just the neighborhood, it’s all of Labelle. I came from North Fort Myers where the traffic is horrible and there’s a lot of crime. The people in Labelle are friendly and I find quite religious. Each time I checked the real estate apps, there was 0 crime reported in those neighborhoods. It’s a wonderful place."
    32
    Flag
  • Elvis S.
    "Good town to live and pretty quiet with minimum problems and a little bit of everything with not too many places to hang around but close to big cities "
    0
    Flag
  • Sierra B.
    "There are lots of owners who let their dogs run around off leash without supervision so there have been situations where a dog follows me and my dogs all the way to our home. "
    12
    Flag
  • Clorivel L.
    "You need a vehicle to get around. The taxi service is not dependable. There are no Uber or Lyft options here. There is no public transportation in this small town."
    0
    Flag
  • Billings.deb
    "The neighborhood welcomes new people so easily...even in a very small old Florida town. The neighborhood has 3 people that raise chickens and they give them to neighbors."
    9
    Flag
  • Jgaud1988
    "It is a very friendly small town, there are plenty of parks for kids and plenty of stores that have just about all of your every day needs"
    7
    Flag
  • William W.
    "We live just outside.of city limits. Very pleasant little downtown area with Charlie's Coffee shop, Belle's Ice Cream Store and Forrey's Grill."
    0
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  • Charles S.
    "It’s a pretty great area to live, family lives close by. It’s a very small town, living in a small town is always fun"
    0
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  • Tris
    "The elementary schools are good but middle and high schools aren’t great.. very small town not much to do except get in trouble "
    0
    Flag
  • Mary V.
    "This neighborhood is where me and my brothers grew up. Rode bicycles and used skates. very friendly "
    5
    Flag
  • Samanthabrogers
    "We have local Plays, festivals, community events and music concerts. The town is small and everybody knows your name. "
    9
    Flag
  • Jamie B.
    "I grew up here and then bought the home I was raised in from my mom. our neighbors all.look out for each other and it's just a wonderful place to raise kids, retire or just about anything. We are basically right between Orlando, Tampa and Miami but away enough to have the quiet small town feel :)"
    0
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  • Mark J.
    "Mainly made up of larger parcels this area brings peace of mind with its relaxing atmosphere. Enjoy the natural Florida landscape and convenience of a major thoroughfare for quick travel to nearby areas."
    0
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Market trends in Labelle

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
188
6MoM

Home Value

Trulia Estimate
$1.08M
Since last month
Increased$5K (+0.4%)
Since last year
Increased$134K (+14.1%)
Since last sale
Increased$444K (+69.3%)
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 +53% in the last 10 years
MonthEstimated value
2026
August 2026$1.08M
July 2026$1.08M
June 2026$1.08M
May 2026$1.09M
April 2026$1.09M
March 2026$1.1M
February 2026$1.1M
January 2026$1.1M
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
1236 March Ln, Labelle, FL
0.78
Single-Family Home
$372,999
05/22/26
4
2
1,828
1300 E Bucknell Ln, Labelle, FL
0.84
Single-Family Home
$340,000
07/20/26
4
2.5
1,503
1044 Bucknell Ln, Labelle, FL
1.03
Single-Family Home
$425,000
02/20/26
3
2
1,681
1069 N Hilton Cir, Labelle, FL
1.02
Single-Family Home
$350,000
11/07/25
4
3
1,616
1035 March Ln, Labelle, FL
0.84
Single-Family Home
$325,000
09/26/25
3
2
1,362
1115 Leader St, Labelle, FL
0.90
Single-Family Home
$318,000
02/17/26
3
2
1,681
1712 Frontier CIR, Labelle, FL
1.60
Single-Family Home
$650,000
06/05/26
3
2
2,239
1008 Bucknell Ln, Labelle, FL
0.98
Single-Family Home
$309,000
10/08/25
3
2
1,863
1042 N Bronze CT, Labelle, FL
0.91
Single-Family Home
$306,000
01/28/26
3
2
1,449

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
1566 Winchester Ave E, Labelle, FL 33935
0.06
$712,000
4
3
2,751
Off Market
1407 Winchester Ave W, Labelle, FL 33935
0.06
-
-
-
-
Off Market
1135 Firebrand Ct #W, Labelle, FL 33935
0.22
$899,000
3
3.5
2,850
Off Market
15920 Firebrand Ct, Labelle, FL 33935
0.31
-
-
-
-
Off Market
1170 Firebrand Ct, Labelle, FL 33935
0.35
$685,000
3
2.5
2,043
Off Market
1031 March Ln, Labelle, FL 33935
0.61
$29,600
3
2
1,343
Off Market
0000 March Lane, Labelle, FL 33935
0.61
-
-
-
-
Off Market
4 March Ln, Labelle, FL 33935
0.63
-
-
-
-
Off Market
8012 Oakleaf Cir, Labelle, FL 33935
0.65
$353,500
4
3
1,715
Off Market
1077 March Ln, Labelle, FL 33935
0.65
$361,800
4
3
1,935
Off Market
5030 N Pechatree Cir, Labelle, FL 33935
0.65
$387,700
4
3
1,935
Off Market

Price and Tax history

DateEventPrice
Apr 1, 2026
Source: Florida Gulf Coast MLS #2025009608
PriceChange
$1,169,000
Price decreased by 2%
Sep 19, 2025
Source: Florida Gulf Coast MLS #2025009608
Listed For Sale
$1,189,000
Oct 27, 2023
Source: Florida Gulf Coast MLS #223019677
ListingRemoved
Aug 1, 2023
Source: BeachesMLS #RX-10872329
PriceChange
$1,499,900
Price decreased by 3%
Jul 18, 2023
Source: BeachesMLS #RX-10872329
PendingToActive
$1,549,900

LGBTQ Local Legal Protections

Maureen Creagh, Weatherford Realty Group LLC
Agent Phone: (863) 233-1847
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 1444 E Winchester Ave

  • What is the estimated monthly payment for 1444 E Winchester Ave?
    Based on a $1,169,000 list price with 20% down at today's rates, the estimated monthly payment for 1444 E Winchester Ave in Labelle, FL is approximately $7,835 (about $6,084 principal & interest, $1,676 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • What do residents say about Labelle?
    Residents describe Labelle, FL as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See homes for sale in Labelle, FL.
  • What are the closest schools to 1444 E Winchester Ave?
    The closest schools to 1444 E Winchester Ave in Labelle, FL are Glades Virtual Franchise (Middle/High), Glades Virtual Instruction Program (Elementary/Middle/High, rated 3/10), Moore Haven Elementary School (Pre-K, rated 5/10).
  • What is 1444 E Winchester Ave estimated to be worth?
    Trulia's estimated value for 1444 E Winchester Ave in Labelle, FL is $1,083,700.
  • Does 1444 E Winchester Ave have air conditioning?
    Yes, 1444 E Winchester Ave in Labelle, FL has air conditioning.
  • Does 1444 E Winchester Ave have a pool?
    Yes, 1444 E Winchester Ave in Labelle, FL has a pool.
1444 E Winchester Ave, Labelle, FL 33935 is a 6 bedroom, 6 bathroom, 5,176 sqft single-family home built in 2001. This property is currently available for sale and was listed by Florida Gulf Coast MLS on Sep 19, 2025. The MLS # for this home is MLS# 2025009608.