237 Gary Dr, Winter Garden, FL 34787
OFF MARKET

237 Gary Dr
Winter Garden, FL 34787

  • 2 Beds
  • 1 Bath
  • 1,027 sqft

$420,900

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $2,900/mo*
Refinance Your Home

$420,900

Trulia Estimate
as of Jun 29, 2026
Est. Refi. Payment $2,900/mo*
Refinance Your Home
2 Beds
1 Bath
1,027 sqft

Local Information

  • Map ViewExplore the area around 237 Gary Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

A Rare Offer - this Historic home on spacious lot in Downtown Winter Garden. A short stroll or golf cart ride away, 237 Gary Drive features over 1000 sqft - 2 bedrooms, 1 total bathroom. The garage could easily be a bedroom and likely was one in the past. The seller would be willing to help with this transition with the right offer. Super clean move in ready home - with recent updates throughout. The galley kitchen was remodeled with new cabinets, gorgeous granite, and S/S appliance package. The living area is bright with natural light passing through the plantation shutters and large front windows. The covered rear patio is the place to spend summer evenings and the large rear yard is fully fenced. Aside from being very close to famed Plant Street and West Orange Bike Trail, this property is very convenient to the 429, the Turnpike, near top rated public and private schools, and Winter Garden Village.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
No Info
View
No Info
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 237 Gary Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Appliances & Utilities
MicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: Shake Shingle
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1974Year Updated: 1974
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 10454 sqft

Price History for 237 Gary Dr

DatePriceEventSource
07/24/2018$247,000Sold
N/A
06/20/2018$254,900PendingAgent Provided
06/08/2018$254,900Listed For SaleAgent Provided
06/20/2015$90,000Sold
N/A

Market trends in Winter Garden

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$592K
$1.67KMoM
Sale-to-List Price
98.3%
0.3%MoM
Price per sq ft
$248
$3MoM
Available listings
744
17MoM
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Property Tax and Assessment

Year2024
Tax$3,026
Assessment$381,250
Home facts updated by county records

Comparable Sales for 237 Gary Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
236 E Newell St, Winter Garden, FL
0.09
Single-Family Home
$543,000
03/10/26
2
2
1,659
215 Pennsylvania Ave, Winter Garden, FL
0.55
Single-Family Home
$289,000
08/07/25
2
1
836
344 E Maple St, Winter Garden, FL
0.48
Single-Family Home
$390,000
07/30/25
3
1
1,150
85 N Boyd St, Winter Garden, FL
0.38
Single-Family Home
$450,000
08/18/25
3
1
1,067
345 Winter St, Winter Garden, FL
0.56
Single-Family Home
$285,000
06/08/26
2
1
700
135 E Story Rd, Winter Garden, FL
0.68
Single-Family Home
$280,000
09/12/25
2
1
957
112 N Lakeview Ave, Winter Garden, FL
0.49
Single-Family Home
$505,000
08/21/25
2
1
1,342
18 W Vining St, Winter Garden, FL
0.71
Single-Family Home
$435,000
02/17/26
2
1
948
308 Florida Avenue, Winter Garden, FL
0.52
Single-Family Home
$315,000
02/20/26
3
2
1,050
329 W Bay St, Winter Garden, FL
0.71
Single-Family Home
$375,000
02/02/26
2
1
1,004

Nearby homes

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Assigned Schools

These are the assigned schools for 237 Gary Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Winter Garden

At least 511 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

  • 47 % Say it's walkable to restaurants

  • 43 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • 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
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  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
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  • 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
    Flag
  • 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
  • Dawnddavidson1
    "Great little town if you live in the north side near old Winter Garden. Quaint small town feel with plenty to do. Surrounding area is overdeveloped like everywhere in central Florida. Schools could be better. Real estate is inflated, but the town is desirable. Everything you need is close; no need to go to Orlando for much. "
    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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
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Homes for sale near 237 Gary Dr

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Off Market Homes Near 237 Gary Dr

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237 Gary Dr, Winter Garden, FL 34787 is a 2 bedroom, 1 bathroom, 1,027 sqft single-family home built in 1974. This property is not currently available for sale. 237 Gary Dr was last sold on Jul 24, 2018 for $247,000. The current Trulia Estimate for 237 Gary Dr is $420,900.