5644 Thomas Square Dr, Winter Garden, FL 34787
OFF MARKET

$660,000

Trulia Estimate
  • 4 Beds
  • 4.5 Baths
  • 2,600 sqft

5644 Thomas Square Dr, Winter Garden, FL 34787

Est. Refi. Payment $4,892/mo*
Refinance Your Home
Currently Off Market - Sold Oct 6, 2021 for $535,000

Home Value

Trulia Estimate
$660K
Since last month
Increased$1K (+0.2%)
Since last year
Decreased$3K (-0.4%)
Since last sale
Increased$124K (+23.1%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +106% in the last 10 years
MonthEstimated value
2026
October 2026$659K
September 2026$659K
August 2026$658K
July 2026$664K
June 2026$659K
May 2026$663K
April 2026$653K
March 2026$648K
February 2026$647K
January 2026$639K
2025
2024
2023
2022
2021
2020
2019
2018
2017

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
5596 THOMAS SQUARE DR, Winter Garden, FL
0.07
Single-Family Home
$578,000
06/18/26
4
3.5
2,458
15107 KIRSTY ALLEY, Winter Garden, FL
0.06
Single-Family Home
$570,000
01/27/26
4
2.5
2,292
5431 BOWMAN DRIVE, Winter Garden, FL
0.18
Single-Family Home
$640,000
04/15/26
4
3.5
2,458
5518 THOMAS SQUARE DRIVE, Winter Garden, FL
0.16
Single-Family Home
$585,000
01/08/26
5
4.5
2,775
5460 BOWMAN DRIVE, Winter Garden, FL
0.21
Single-Family Home
$550,000
07/27/26
3
3.5
2,474
5743 THOMAS SQUARE DRIVE, Winter Garden, FL
0.12
Single-Family Home
$826,000
09/21/26
4
2.5
2,917
5611 BOWMAN DRIVE, Winter Garden, FL
0.05
Single-Family Home
$557,000
12/22/25
4
2.5
2,292
5443 BOWMAN DRIVE, Winter Garden, FL
0.18
Single-Family Home
$649,000
07/02/26
4
4.5
2,656
15518 SUNQUAT DRIVE, Winter Garden, FL
0.31
Single-Family Home
$607,000
06/02/26
4
3.5
2,502
5637 TIGER WAY, Winter Garden, FL
0.15
Single-Family Home
$760,000
05/27/26
4
2.5
2,917

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
5638 Thomas Square Dr, Winter Garden, FL 34787
0.01
$572,200
4
3
2,455
Off Market
5632 Thomas Square Dr, Winter Garden, FL 34787
0.02
$563,100
2
3
2,195
Off Market
5626 Thomas Square Dr, Winter Garden, FL 34787
0.02
$605,400
4
4
2,452
Off Market
5653 Bowman Dr, Winter Garden, FL 34787
0.02
$668,500
3
4.5
3,300
Off Market
5647 Bowman Dr, Winter Garden, FL 34787
0.02
$561,400
3
4
2,326
Off Market
5641 Bowman Dr, Winter Garden, FL 34787
0.03
$628,100
4
3.5
2,458
Off Market
5620 Thomas Square Dr, Winter Garden, FL 34787
0.03
$572,000
4
3
2,292
Off Market
5635 Bowman Dr, Winter Garden, FL 34787
0.03
$567,500
4
3.5
2,315
Off Market
15112 Newtonia St, Winter Garden, FL 34787
0.03
$618,500
4
5
2,607
Off Market
15106 Newtonia St, Winter Garden, FL 34787
0.03
$498,200
2
2.5
1,975
Off Market
15118 Newtonia St, Winter Garden, FL 34787
0.03
$559,000
4
2.5
2,548
Off Market
15124 Newtonia St, Winter Garden, FL 34787
0.03
$471,200
3
2.5
1,858
Off Market
5629 Bowman Dr, Winter Garden, FL 34787
0.03
$576,100
3
3
2,284
Off Market
5614 Thomas Square Dr, Winter Garden, FL 34787
0.04
$557,700
3
4
1,984
Off Market
15130 Newtonia St, Winter Garden, FL 34787
0.04
$549,400
4
3.5
2,139
Off Market
Thomas square Dr, Winter garden, FL 34787
0.04
-
-
-
-
Off Market
5623 Bowman Dr, Winter Garden, FL 34787
0.04
$501,300
3
3
1,838
Off Market
5608 Thomas Square Dr, Winter Garden, FL 34787
0.04
$542,800
3
3
1,990
Off Market
15136 Newtonia St, Winter Garden, FL 34787
0.04
$669,600
4
3
2,768
Off Market
5617 Bowman Dr, Winter Garden, FL 34787
0.04
$544,000
3
3.5
2,228
Off Market

Local Information

  • Map ViewExplore the area around 5644 Thomas Square Dr.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2017
2,600 sqft
$254/sqft
Garage

About this House

What's unique:Law suiteSide yardHigh-end appliances
This single-family home is located at 5644 Thomas Square Dr, Winter Garden, FL. 5644 Thomas Square Dr is in Winter Garden, FL and in ZIP code 34787. This property has 4 bedrooms, 5 bathrooms and approximately 2,600 sqft of floor space. This property has a lot size of 7850 sqft and was built in 2017.
5644 Thomas Square Dr, Winter Garden, FL 34787 is a 4 bedroom, 5 bathroom, 2,600 sqft single-family home built in 2017. It last sold for $535,000 on Oct 6, 2021. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $660,000, with a rent estimate of $3,812/month.

Home Details for 5644 Thomas Square Dr

Interior Features

Heating & Cooling
Heating: Forced Air, Electric, GasHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Laminate
Interior Details
In-law unitTypes of Rooms: Walk In Closet, Breakfast Nook, Family Room, Laundry Room, Master Bath, Office, Pantry, Recreation RoomCeiling Fan
Appliances & Utilities
Cable ReadyDishwasherDisposalDryerMicrowaveRefrigeratorWasher
Windows, Doors, Floors & Walls
Double Paned Windows
Security
Security System

Property Information

Year Built
Year Built: 2017
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
DeckExterior: Shingle, Stucco, Cement ConcreteLawnPatioSprinkler System
Parking & Garage
GarageParking: Garage Detached

Community

Units in Building: 1

Lot Information

Lot Area: 7850 sqft

Price and Tax history

DateEventPrice
Oct 5, 2024
Source: Stellar MLS #T3325714
ListingRemoved
$534,900
Oct 5, 2023
Source: Stellar MLS #T3325714
ListingRemoved
Oct 6, 2021
Source: N/A
Sold
$535,000
Aug 25, 2021
Source: Stellar MLS #T3325714
Pending
$534,900
Aug 23, 2021
Source: Stellar MLS #T3325714
Listed For Sale
$534,900

Market trends in Winter Garden

Last updated September 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$585K
$333MoM
Sale-to-List Price
98.1%
Price per sq ft
$247
$4MoM
Available listings
717
27MoM
Sourced by Trulia Market Trends

Around this home

What Locals Say about Winter Garden

This October

Trick-or-Treat Score

Built from what locals say about this neighborhood.
  • 88% say there are sidewalks
  • 81% say there's holiday spirit
  • 54% say neighbors are friendly
Trulia Trick or TreatStart Ghost Hunt
At least 513 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 88 % Say there are sidewalks

  • 86 % Say car is needed

  • 83 % Say parking is easy

  • 81 % Say there's holiday spirit

  • 78 % Say kids play outside

  • 76 % Say it's quiet

  • 75 % Say streets are well-lit

  • 74 % Say people would walk alone at night

  • 72 % Say yards are well-kept

  • 61 % Say they plan to stay for at least 5 years

  • 54 % Say neighbors are friendly

  • 54 % Say there's wildlife

  • 50 % Say it's walkable to grocery stores

  • 46 % Say it's walkable to restaurants

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • jhp331
    "A rated schools and lots to do for families "
    0
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  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
    Flag
  • Amanda
    "Great safe area for all ages and diversity. Good schools, lots of shopping, dining, nearby and more coming."
    0
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  • Ypgs9v7hpd
    "It is a nice area and the schools are nice. It is good area to raise children away from the tourists area and the city ."
    0
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  • Ypgs9v7hpd
    "The only thing that is unique about this neighborhood is the people that are friendly and the kids get along great. The only downside of living here in Wintergarden is it’s not enough places to go out to eat and it is not enough places for kids to hang out or teenagers to hang out and the closest place for teenagers to hang out is at the Wintergarden Grove area where you have to take off the exit 9, which I think that’s a bit too far for them to hang out when they can remain closer, it would be better if they had a place to hang out within the neighborhood. Also, Price is over here for a living is very high so if you’re not making a decent amount of money, it is expensive even the apartments that are surrounding it. It’s expensive.."
    0
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  • Emilye Chasen
    "Downtown events occur all the time. Christmas, Halloween, 4th of July etc. Santa comes down my street"
    1
    Flag
  • Ypgs9v7hpd
    "I’ve living here for the last 3 yrs. It’s nice area, people are nice. It’s nice area to raise your family there."
    0
    Flag
  • Heather Kotyk
    "I work near the airport and the commute using the turnpike and I4 is about 25-30 minutes. Traffic is usually manageable and continuously is moving "
    0
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  • Erin
    "There are many families in the neighborhood, a great playground and an A rated school nearby. There’s also a grocery store and pharmacy conveniently within a mile. "
    0
    Flag
  • Maria Rojas
    "Great place to have a family, lots of parks and activities for kids. Amazing schools and the community is very united. Most communities have hoa "
    0
    Flag
  • Rosa Aguilar
    "There’s lots of places, activities, parks, trails to take kids. There’s also lots of churches with daycare and city programs for children to take part in."
    0
    Flag
  • Andres.toro
    "Mostly all good schools. A lot of parks (and a few others upcoming) and services are increasing in availability. "
    0
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  • Logan Mahalek
    "The historic area of downtown winter garden boasts local shops and restaurants and also hosts a farmers market every weekend. There is also plenty of name brands within 15 minutes "
    0
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  • Cfbranf3rd
    "I’m don’t have a commute, as I’m retired. I’m in Cypress Reserve, and Avalon Road can be a nightmare at school drop off/pick up times."
    0
    Flag
  • Kelly
    "Beautiful, safe & friendly area. Winter Garden is a great place to raise a family! This is a very active area with tons of activities. Lots of wildlife & opportunities to get in touch with nature. Big, beautiful Florida birds and animals all around. Great restaurants too! "
    0
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  • Geisha
    "In Winter Garden for the area's of Horizon West, Hamlin, Summerlake, Waterleight, The Grove is amazing is like living in a perfect community bubble completely recomend"
    0
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  • Catherine Law
    "There is a private lake side park and a bbq area. Dogs poop trash and bags available. Dogs need to be on leash all the time. No many houses are fenced. "
    0
    Flag
  • Vanessaasantini
    "Wonderful , Safe, beatiful, peaceful, very good, clean, good school, nice and bog city Close to supermarket, gas station "
    2
    Flag
  • Aj2636
    "Halloween costume parties for kids. Community Easter egg hunts. Santa Claus visits on a fire truck. Community watch parties for football games. A soccer field, tennis courts, pickleball courts and basketball courts that allow the neighborhood to enjoy each other’s company. During COVID, we had live music performances in the park."
    0
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  • Cara Conley
    "The area is established and offers. Great amenities within 15 minutes. Clean and safe and welcoming."
    1
    Flag
  • Isaac Peterson
    "Very friendly and helpful neighbors, and the schools are awesome. Very safe "
    2
    Flag
  • Aj2636
    "I’ve lived here for 11 years. It’s close to shopping. The neighborhood feels comfortable with homes far apart from each other. Nice lakes nearby that most neighborhoods have access to. Hospital close-by for emergencies."
    1
    Flag
  • Felton.amanda
    "I lived here for 10 years and just now moving this month. The neighborhood is safe not a lot of crime just a few thieves here and there that steal packages from ppls door steps occasionally."
    1
    Flag
  • Dismiki24
    "Lots of dogs in our neighborhood but many don’t pick up after their dogs. There is a dog park nearby "
    0
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  • Jason M.
    "We see people walk their dogs all the time. The neighborhood has dog stations for easy to dispose of waste. "
    0
    Flag
  • Megan E.
    "You will love it! Lots of dog owners and very kind. Lots of doggy poop bag stations as we all know! Great dog parks and trails to go on lovely long walks. "
    13
    Flag
  • Zimmiac
    "Everything is very nice ,and the persons are very nice ,very quite area and the schools are good also,parks and events as well very nice"
    0
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  • Lil D.
    "The people and shops are great. Love all the bike tails as well. Every Saturday they have the farmers market and quite enjoyable to go to and walk around. "
    0
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  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
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  • Hollister M.
    "Lots of dogs. Most people are very polite about their dogs. People with cats do not keep them indoors and they roam the streets a lot. Most people pick up after their dogs and keep them on leashes."
    0
    Flag
  • Jim
    "It’s an amazing place to love. Doesn’t feel like living in Florida. I love living the country and still being close to Disney"
    6
    Flag
  • Cathy
    "Great it is safe and very homey the people are friendly and irs all clean. Very close to shopping places to eat and nice bars "
    5
    Flag
  • Jonathancrespo21
    "We have a neighborhood Facebook page open to everyone and we use this to communicate with each other regularly. We participate in food drives, raise money for special causes, and even sponsor dinners for our local police, firefighters, and nurses."
    0
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  • Chuckfink
    "Farmers market every Saturday. Monthly events downtown, car shows, Christmas party, local community theater. Things to do almost every week."
    0
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  • Valerie
    "Weekend Farmers Market. Beautiful downtown area. Older historic feeling. Very convenient with shops food and stores. Best city I've lived in since being here in Florida."
    0
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  • jay j
    "People love dogs. They are loving animals that make everyone happy when they see them. Most people now a days have dogs"
    0
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  • Nicola O.
    "Some neighbors don’t clean up after their pets or leave their pets on the balcony barking all night long, but there is a lot of open grass fields and dog stations all throughout. "
    0
    Flag
  • Candy H.
    "Winter Garden Farmer’s Market and shows going on at the Garden Theatre, along with more dog friendly mom and pop places."
    0
    Flag
  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 5644 Thomas Square Dr

  • What is 5644 Thomas Square Dr estimated to be worth?
    Trulia's estimated value for 5644 Thomas Square Dr in Winter Garden, FL is $660,000.
  • What is the price history for 5644 Thomas Square Dr?
    5644 Thomas Square Dr in Winter Garden, FL last sold for $535,000 in October 2021.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a buyer's market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $585K. That is down $333 from the prior month.
  • Does 5644 Thomas Square Dr have laundry facilities?
    Yes, 5644 Thomas Square Dr in Winter Garden, FL has in-unit laundry.
  • How big is the lot at 5644 Thomas Square Dr?
    The lot at 5644 Thomas Square Dr in Winter Garden, FL is about 0.18 acres (7,850 sq ft).

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