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$825,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 2,917 Sq. Ft.
  • Updated 14 hours ago
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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.

Full Property Details for 5743 Thomas Square Dr

General

  • Price: $825,000
  • HOA FEE: $215/month
  • Taxes: $10,730 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6433669
  • Updated: 8/15/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Ceiling Fan(s), Eating Space In Kitchen, High Ceilings, Kitchen and Family Room Combination, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
  • Appliances: Dishwasher, Disposal, Microwave, Range, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Carpet, Engineered Hardwood, Tile

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Shared Amenities: Fitness Center, Playground, Pool
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Lighting, Salt Water, Solar Heat
  • Spa Description: Heated

Exterior

  • Exterior Features: Irrigation System, Lighting, Sliding Doors
  • Deck/Patio: Enclosed, Patio, Screened
  • Porch/Patio/Deck: Enclosed, Patio, Screened

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: OVERLOOK AT HAMLIN
  • Driving Directions: From New Independence Pkwy, turn right onto Hamlin Groves. In 0.8 miles turn left onto Shonan Gold Dr. In 700 ft turn left onto Thomas Sq Dr. Home is on your right.
  • Direction Faces: West

School Information

  • Elementary School: Independence Elementary
  • Middle School: Bridgewater Middle
  • High School: Horizon High School

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Community Boat Ramp, Water Access, Waterfront, Deed Restrictions, Fitness Center, Playground, Pool, Sidewalks
  • Optional Amenities: Fitness Center, Playground, Pool
  • Association: Yes
  • Assoc. Name: Castle Management, LLC
  • Assoc. Fees Include: Community Pool, Manager
  • Pet Restrictions: Buyer to verify with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE HANCOCK
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable TV Available, Cable Connected, Natural Gas Connected

Structural Information

  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Windows: Blinds, Window Treatments
  • Stories/Levels: One
  • Square Feet: 2,917
  • Sq. Ft. Source: Public Records
  • Year Built: 2018

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.18
  • Lot Size (Sq. Ft.): 7,984
  • Lot Size: 7984
  • Street/Road Desc.: Concrete
  • Fencing (Description): Fenced

Water Features

  • Water View: Yes
  • Water Front Name: LAKE HANCOCK
  • Water Front Desc.: Waterfront

Financial Considerations

  • Association Fee: $215
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $10,730.6
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: OVERLOOK 2 AT HAMLIN PHASE 2 AND 5 89/107 LOT 213
  • Flood Zone Info: X
  • APN: 202327585302130
  • Property ID: 202327585302130
  • Block/Lot/Section: 2

Listed by Compass Florida Llc

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Listing agents

— 5743 Thomas Square Dr —

  • Compass Florida Llc

  • Compass Florida Llc

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5743 Thomas Square Dr

School District:Orange County School District
NameGradesDistance
Independence Elementary
6255 New Independence Parkway, Winter Garden, FL 34787
K-51.1 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-81.2 mi
Horizon High School
10393 Seidel Road, Winter Garden, FL 34787
9-123.1 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5743 Thomas Square Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/14/2026
Listed
$825,000
11.49%
MLS
12/29/2022
Sold
$740,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5743 Thomas Square Dr

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,731
4%
$684,873
6%
2024
$10,344
7%
$648,074
3%
2023
$9,634
37%
$629,198
37%
2021
$7,030
-1%
$460,684
-3%
2022
$7,125
1%
$474,505
15%
2021
$7,030
2%
$413,714
4%
2019
$6,869
464%
$397,338
468%
2018
$1,218
87%
$70,000
141%
2017
$652
32%
$29,100
—
2016
$495
—
$29,100
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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Listed by Compass Florida Llc

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5743 Thomas Square Drive, Winter Garden, FL 34787 (MLS# O6433669) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 5743 Thomas Square Drive is currently listed for $825,000 and was received on August 14, 2026. Want to learn more about 5743 Thomas Square Drive? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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