5743 THOMAS SQUARE DRIVE
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    +55 more
    Active
    Single Family Residence

    5743 THOMAS SQUARE DRIVE

    WINTER GARDEN, FL, 34787·OVERLOOK AT HAMLIN

    MLS# O6433669

    $825,000

    4

    Beds

    2.5

    Baths

    2,917

    Sq Ft

    Description

    Under contract-accepting backup offers. Welcome to 5743 Thomas Square Drive, an exceptional single-story pool home located in the lakefront community of The Cove at Hamlin in Winter Garden. Built in 2018, this beautifully upgraded Jamestown model offers 4 bedrooms, 2.5 bathrooms, 2,917 square feet, and a thoughtfully designed split floor plan that combines comfort, style, and effortless Florida living. Inside, engineered hardwood floors, custom archways, high ceilings, and abundant natural light lead into an expansive open-concept living space. The kitchen serves as the heart of the home with quartz countertops, stainless steel appliances, generous cabinetry, and seamless flow into the dining and living areas. One of the home's most impressive features is the massive owner's suite. Offering an exceptional amount of space rarely found in homes of this size, the suite easily accommodates a full bedroom setup with room for a sitting area, additional furnishings, or a private retreat within the room. A spacious owner's bath and generous custom closet complete the suite, while three additional bedrooms provide flexibility for family, guests, or a home office. Step outside to an extended screened lanai overlooking the private saltwater pool and beautifully landscaped fenced backyard. Solar and natural gas pool heating, built-in lighting, a fire pit, and a gas connection for an outdoor grill create a backyard designed for entertaining and enjoying the Florida lifestyle year-round. Lake views complete the setting, along with the opportunity to enjoy nightly Disney fireworks from home. Beyond the home, one of the biggest draws is the incredible Hamlin lifestyle just minutes from your front door. Spend an evening putting at PopStroke, catch a movie from a luxury recliner at Cinépolis, grab dinner at Ford's Garage or Agave Bandido, meet friends at Home State Brewing Co., or start the morning with coffee and breakfast at Toastique. Hamlin continues to offer an exciting mix of restaurants, entertainment, shopping, fitness, community events, and everyday conveniences, making it easy to enjoy a night out without traveling far from home. The Cove at Hamlin offers its own impressive collection of amenities, including a resort-style community pool, clubhouse, fitness center, splash pad, playgrounds, dog park, walking trails, outdoor gathering spaces, and private access to Lake Hancock with a community boat ramp and dock. With easy access to SR 429, Walt Disney World, Hamlin Town Center, and everything Horizon West has to offer, 5743 Thomas Square Drive is more than a beautiful pool home. It offers the opportunity to live in the heart of one of Central Florida's most exciting and rapidly growing communities.

    Property Overview

    StatusActive Under Contract
    TypeSingle Family Residence
    Year Built2018
    CityWINTER GARDEN
    Area34787 - WINTER GARDEN
    SubdivisionOVERLOOK AT HAMLIN
    StateFL
    CountyOrange
    List Date08/14/2026
    MLS#O6433669
    List Price$825,000

    Bedrooms & Bathrooms

    Bedrooms4
    Bathrooms2.5
    Full Bathrooms2
    Half Bathrooms1

    Structure

    Garage Capacity2
    Construction MaterialsBlock, Concrete, Stucco
    RoofShingle
    Foundation DetailsSlab
    FlooringCarpet, Hardwood, Tile
    Private PoolYes
    Patio & PorchEnclosed, Patio, Screened

    Size & Lot

    Living Area2,917 sqft
    Lot Size7,984 sqft
    Acres0.18
    Water FrontNo

    Utilities

    HeatingCentral, Electric
    CoolingCentral Air
    WaterPublic
    SewerPublic Sewer

    Additional Features

    Interior FeaturesCeiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
    Exterior FeaturesLighting, Sliding Doors
    AppliancesDishwasher, Disposal, Microwave, Range, Refrigerator

    Contact Agent

    Holiday Realty LLC

    Central Florida Real Estate Experts

    (800) 936-1754

    Our team typically responds within 1 hour during business hours.

    Neighborhood

    About OVERLOOK AT HAMLIN

    5743 THOMAS SQUARE DRIVE is located in the OVERLOOK AT HAMLIN community in WINTER GARDEN, FL. Part of Orange County.

    The OVERLOOK AT HAMLIN neighborhood offers convenient access to local schools, shopping, dining, parks, and major commute routes.

    HOA & Tax Information

    Annual Property Tax$10,730.6 (2025)

    HOA, Community & Pets

    HOA & Recurring Fees

    AssociationCastle Management, LLC
    HOA Fee$214.68 / monthly
    Fee Includes
    Pool
    Management
    Amenities
    Fitness Center
    Playground
    Pool

    Community Features

    Deed Restrictions
    Fitness Center
    Playground
    Pool
    Sidewalks
    Water Features
    Community Boat Ramp,Water Access,Waterfront

    Pet Policy

    Pets AllowedYes

    Pet policies are subject to HOA/condo association rules. Verify current restrictions before purchase.

    Ask About This Property

    Ask a question about this home and get quick, listing-based help from Holiday Realty.

    Answers are generated from listing data and may be incomplete — please verify details with a Holiday Realty agent.

    Listing courtesy of COMPASS FLORIDA LLC · Matthew McKee

    Frequently Asked Questions

    What is the asking price for 5743 THOMAS SQUARE DRIVE?

    The listing price for 5743 THOMAS SQUARE DRIVE is $825,000.

    How many bedrooms and bathrooms does 5743 THOMAS SQUARE DRIVE have?

    This property features 4 bedrooms and 2 full bathrooms plus 1 half bath(s).

    What is the square footage of 5743 THOMAS SQUARE DRIVE?

    The living area is approximately 2,917 square feet.

    What community is 5743 THOMAS SQUARE DRIVE located in?

    This property is located in the OVERLOOK AT HAMLIN community in WINTER GARDEN, FL. The neighborhood offers convenient access to local schools, shopping, dining, and parks.

    When was 5743 THOMAS SQUARE DRIVE built?

    This property was built in 2018.

    What schools are near 5743 THOMAS SQUARE DRIVE?

    WINTER GARDEN is served by the Orange County Public Schools district. Contact us for details on nearby elementary, middle, and high schools, including ratings and enrollment information.

    How do I schedule a showing for 5743 THOMAS SQUARE DRIVE?

    You can schedule a private showing by clicking "Schedule a Showing" on this page or calling us at (800) 936-1754.

    Listings courtesy of Stellar MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of 2026-08-21. All data is obtained from various sources and may not have been verified by broker or MLS GRID.

    IDX information is provided exclusively for consumers' personal noncommercial use.

    © 2026 Stellar MLS. All rights reserved.