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$618,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 2,458 Sq. Ft.
  • Updated 4 days ago
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Welcome to this beautiful 4-bedroom, 3.5-bath home in the highly sought-after Overlook at Hamlin community of Winter Garden. Ideally positioned with a serene front lake view, this well-maintained residence offers over 2,400 square feet of thoughtfully designed living space. The open-concept floor plan features a spacious kitchen overlooking the main living and dining areas, perfect for everyday living and entertaining. Upstairs, the generous primary suite and additional bedrooms provide comfort and privacy for the whole family. Enjoy outdoor living from the rear patio and the convenience of nearby Hamlin Town Center shopping, dining, parks, and top-rated schools, with easy access to FL-429. A wonderful opportunity to own in one of Winter Garden's most desirable communities.

Full Property Details for 5596 Thomas Square Dr

General

  • Price: $618,000
  • HOA FEE: $324/month
  • Taxes: $8,568 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6386791
  • Updated: 4/13/2026
  • Added to Site: 47 day(s) ago

Rental Information

  • Min. Lease: 7 Months

Interior

  • Number of Rooms: 5
  • Interior Features: Walk-In Closet(s), Window Treatments
  • Appliances: Dishwasher, Dryer, Microwave, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Carpet, Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Exterior

  • Exterior Features: Irrigation System, Sidewalk

Parking

  • 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 FL-429 take Exit 15 (New Independence Pkwy), left on Hamlin Groves Tr, right on Thomas Square Dr — home on right.
  • Direction Faces: North

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Association: Yes
  • Assoc. Name: Artemis Lifestyles Services, Inc.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Public, Water Available

Structural Information

  • Exterior Const.: Stucco, Wood Frame
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 2,458
  • Sq. Ft. Source: Public Records
  • Year Built: 2015

Lot Features

  • Lot Size (Acres): 0.17
  • Lot Size (Sq. Ft.): 7,548
  • Lot Size: 7548
  • Street/Road Desc.: Concrete, Paved

Financial Considerations

  • Association Fee: $324
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $8,568.93
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: OVERLOOK 2 AT HAMLIN PHASE 1 AND 6 84/10 LOT 73
  • Flood Zone Info: x
  • APN: 2023275846 00730
  • Property ID: 2023275846 00730
  • Block/Lot/Section: 58

Listed by Xcellence Realty Inc.

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Listing agent

— 5596 Thomas Square Dr —

  • Xcellence Realty Inc.

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5596 Thomas Square Dr

School District:Orange County School District
NameGradesDistance
Independence Elementary
6255 New Independence Parkway, Winter Garden, FL 34787
K-51.2 mi
Bridgewater Middle School
5600 Tiny Road, Winter Garden, FL 34787
6-81.1 mi
Horizon High School
10393 Seidel Road, Winter Garden, FL 34787
9-123.3 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 5596 Thomas Square Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/02/2026
Listed
$618,000
67.03%
MLS
12/08/2015
Sold
$369,995
—
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 5596 Thomas Square Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$8,174
—
$481,052
-9%
2024
$8,174
16%
$528,369
14%
2023
$7,075
25%
$462,694
41%
2021
$5,639
-11%
$328,565
-20%
2022
$6,366
13%
$408,636
30%
2021
$5,639
4%
$315,361
3%
2019
$5,404
1%
$307,157
2%
2018
$5,356
7%
$300,406
8%
2017
$5,027
-7%
$278,812
-5%
2016
$5,410
1450%
$294,935
1375%
2015
$349
—
$20,000
—
View All
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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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Xcellence Realty Inc.

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5596 Thomas Square Dr, Winter Garden, FL 34787 (MLS# O6386791) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 5596 Thomas Square Dr is currently listed for $618,000 and was received on March 02, 2026. Want to learn more about 5596 Thomas Square Dr? 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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