5743 Thomas Square Drive, FL5743 Thomas Square Drive, FL5743 Thomas Square Drive, FL
Stellar MLS
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$825,000

5743 Thomas Square Drive

Winter Garden, FL 34787

Listing updated: August 14, 2026 at 3:50 PM ET

Active
Stellar MLSListing courtesy of Compass Florida Llc · Matthew McKee · MLS #O6433669 · Active · 407-203-9441
4
Beds
3
Baths
2,917
Sq Ft
0.18
Acres
2018
Built
Water viewPrivate pool$283/sqft
Single Family Residence

Property type

2018

Year built

7,984 sqft

Lot size

$283

Price / sq ft

$215/mo

HOA dues

0

Days on market

2

Garage spaces

X

Flood zone

About this home

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 primary 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 primary bath and generous storage 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.

Estimated monthly payment

Principal & interest$4,172
Property taxes$894
Home insurance (est.)$378
HOA dues$215

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Aug 14, 2026
  2. Listed$825,000
    Aug 14, 2026
  3. Price increased$825,000

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
0
Subdivision
Overlook At Hamlin
County
Orange
Year built
2018
Living area
2,917 sq ft
Price/sq ft
$283
Building area
3,742 sq ft (Public Records)
Lot size
7,984 sq ft
Lot category
0 to less than 1/4
Flood zone
X (12095C0380H)
Garage
2 spaces
Pool
Private pool
Annual taxes
$10,731 (2025)
Parcel #
20-23-27-5853-02-130
Zoning
P-D
MLS #
O6433669

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Interior Details

Bedrooms
4
Full bathrooms
2
Half bathrooms
1
Flooring
Carpet, Hardwood, Tile
Appliances
Dishwasher, Disposal, Microwave, Range, Refrigerator
Interior features
Ceiling Fans(s), Eat-in Kitchen, High Ceilings, Kitchen/Family Room Combo, Open Floorplan, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
Laundry
Inside, Laundry Room
Stories / Levels
One
Direction faces
West

Heating & Cooling

Heating
Central, Electric
Cooling
Central Air

Parking

Garage spaces
2
Attached garage
Yes

HOA & Financial

HOA fee
$215 / Monthly
Monthly HOA
$215/mo
Total monthly fees
$215/mo
Total annual fees
$2,576
HOA name
Castle Management, LLC
CDD
No
Homestead exemption
Yes
Min lease term
7 Months
Listing terms
Cash, Conventional, FHA, VA Loan
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
No
Additional lease restrictions
Buyer to verify with HOA
Approval process
Buyer to verify with HOA

Exterior & Construction

Exterior features
Lighting, Sliding Doors
Construction materials
Block, Concrete, Stucco
Roof
Shingle
Foundation
Slab
Pool
Private pool
Water view
Yes
Road surface
Concrete

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Cable Available, Cable Connected, Natural Gas Connected

Community

Pets allowed
Yes

Schools

ElementaryAIndependence ElementaryGreatSchools ↗
MiddleABridgewater MiddleGreatSchools ↗
High SchoolAWindermere High SchoolGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Room Details

RoomLevelDimensions
KitchenFirst18x12
Living RoomFirst20x18
DinetteFirst12x11
Dining RoomFirst11x10
Primary BedroomFirst24x17
Bedroom 2First14x11
Bedroom 3First12x11
Bedroom 4First11x11

Listing Details

Listing date
2026-08-14
On market date
2026-08-14
Original list price
$825,000
Occupant type
Owner
MLS area
34787 - Winter Garden/Oakland
Listing AOR
Osceola
Status changed
2026-08-14
Tax legal description
OVERLOOK 2 AT HAMLIN PHASE 2 AND 5 89/107 LOT 213

Flood risk

Minimal riskFEMA Zone XPanel 12095C0380H

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

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.

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Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of August 14, 2026 at 3:50 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

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