1444 E Winchester Ave
Labelle, FL 33935
6 Beds
5.5 Baths
5,176 sqft (on 3.02 acres)
6 Beds
5.5 Baths
5,176 sqft
(on 3.02 acres)
Local Information
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Description
*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"!
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"!
Home Highlights
Parking
3 Car Garage
Outdoor
Porch, Patio, Pool
View
Landscaped, Pool, Trees/Woods
HOA
None
Price/Sqft
$226
Listed
180+ days ago
Home Details for 1444 E Winchester Ave
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MLS Status: Active |
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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) |
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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 |
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Cumulative Days on Market: 222Days on Market: 180+ |
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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 |
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Price List Price: $1,169,000Price Per Sqft: $226 |
Status Change & Dates Possession Timing: Close Of Escrow |
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Direction & Address City: LabelleCommunity: RANCHETTES |
School Information Elementary School: West GladesJr High / Middle School: Labelle Middle SchoolHigh School: Labelle High School |
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Listing Agent Listing ID: 2025009608 |
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Building Area Building Area: 7197 Square Feet |
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Community Features: Non-Gated, Street LightsNot Senior CommunityUnits in Building: 3 |
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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 |
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Lot Area: 3.02 Acres |
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Listing Terms: All Financing Considered, Cash |
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Business Information Ownership: Single Family |
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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 |
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HOA Amenities: Guest Suites,Hobby RoomSource Internet Entire Listing Display |
Last check for updates: about 19 hours 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.
Price History for 1444 E Winchester Ave
| Date | Price | Event | Source |
|---|---|---|---|
| 04/01/2026 | $1,169,000 | PriceChange | Florida Gulf Coast MLS #2025009608 |
| 09/19/2025 | $1,189,000 | Listed For Sale | Florida Gulf Coast MLS #2025009608 |
| 10/27/2023 | ListingRemoved | Florida Gulf Coast MLS #223019677 | |
| 08/01/2023 | $1,499,900 | PriceChange | BeachesMLS #RX-10872329 |
| 07/18/2023 | $1,549,900 | PendingToActive | BeachesMLS #RX-10872329 |
| 07/18/2023 | $1,549,900 | Contingent | BeachesMLS #RX-10872329 |
| 03/09/2023 | $1,549,900 | Listed For Sale | BeachesMLS #RX-10872329 |
| 09/14/2020 | $640,000 | Sold | MIAMI #A10598434 |
| 12/27/2019 | $659,000 | Pending | Agent Provided |
| 11/18/2019 | $659,000 | PriceChange | Agent Provided |
| 09/13/2019 | $692,500 | PendingToActive | Agent Provided |
| 08/16/2019 | $692,500 | Pending | Agent Provided |
| 07/10/2019 | $692,500 | PriceChange | Agent Provided |
| 04/01/2019 | $695,000 | PriceChange | Agent Provided |
| 03/14/2019 | $724,900 | PriceChange | Agent Provided |
| 01/02/2019 | $749,900 | Listed For Sale | Agent Provided |
| 05/15/2018 | $575,000 | Sold | Florida Gulf Coast MLS #218000708 |
| 02/28/2018 | $595,000 | Pending | Agent Provided |
| 02/13/2018 | $595,000 | PriceChange | Agent Provided |
| 01/03/2018 | $699,900 | PriceChange | Agent Provided |
| 08/24/2016 | $749,900 | PriceChange | Agent Provided |
| 10/12/2015 | $895,000 | Listed For Sale | Agent Provided |
| 11/10/2005 | $775,000 | Sold | N/A |
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $11,924 |
| Assessment | $753,232 |
Home facts updated by county records
Comparable Sales for 1444 E Winchester Ave
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.74 | Single-Family Home | $315,000 | 05/28/25 | 4 | 2 | 1,439 | |
1.03 | Single-Family Home | $425,000 | 02/20/26 | 3 | 2 | 1,681 | |
1.02 | Single-Family Home | $350,000 | 11/07/25 | 4 | 3 | 1,616 | |
0.84 | Single-Family Home | $325,000 | 09/26/25 | 3 | 2 | 1,362 | |
0.90 | Single-Family Home | $318,000 | 02/17/26 | 3 | 2 | 1,681 | |
0.89 | Single-Family Home | $310,000 | 06/17/25 | 3 | 2 | 1,439 | |
0.98 | Single-Family Home | $309,000 | 10/08/25 | 3 | 2 | 1,863 | |
0.91 | Single-Family Home | $306,000 | 01/28/26 | 3 | 2 | 1,449 | |
0.95 | Single-Family Home | $285,000 | 09/02/25 | 3 | 2 | 1,380 |
Assigned Schools
These are the assigned schools for 1444 E Winchester Ave.
- Moore Haven Junior/Senior High School
- PK-12
- Public
- 442 Students
3/10GreatSchools RatingParent Rating AverageThey do absolutely nothing to help a child being bullied. In fact, the teachers do it as well. The staff sets a terrible example for children. Don't bother trying to get the superintendent to help either because he will just push it off to the others you've already been dealing with and have received no help from. The counselor informed me that there are constantly fights there.. they need to take a good hard look at the staff and work their way out.Other Review9y ago - Moore Haven Elementary School
- PK-5
- Public
- 336 Students
5/10GreatSchools RatingParent Rating AverageWe recently moved into the area and enrolled our son at this school. He was bullied by the other kids, and was definitely made to feel unwelcome The school was not up to par in academics and we were very disappointed. We pulled our son out of school there and are moving to another town to have a better school alternative.Parent Review15y ago - Glades Virtual Instruction Program
- K-12
- Public
- 123 Students
3/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Glades Virtual Franchise
- 1-12
- Public
- 14 Students
NAGreatSchools RatingParent Rating AverageNo reviews available for this school. 
Check out schools near 1444 E Winchester Ave.
What Locals Say about Labelle
At least 61 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
70 % Say kids play outside
60 % Say people would walk alone at night
59 % Say there's wildlife
58 % Say neighbors are friendly
54 % 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
Learn more about our methodology.
LGBTQ Local Legal Protections
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.
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.