291 Gary Dr, Winter Garden, FL 34787
OFF MARKET

$959,800

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 3,167 sqft (on 0.25 acres)

291 Gary Dr, Winter Garden, FL 34787

Est. Refi. Payment $6,683/mo*
Refinance Your Home
Currently Off Market - Sold May 12, 2015 for $164,000

Home Value

Trulia Estimate
$960K
Since last month
Decreased$10K (-1%)
Since last year
Decreased$23K (-2.4%)
Since last sale
Increased$796K (+485.2%)
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 +342% in the last 10 years
MonthEstimated value
2026
August 2026$960K
August 2026$959K
July 2026$969K
June 2026$971K
May 2026$956K
April 2026$950K
March 2026$953K
February 2026$947K
January 2026$922K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

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
275 VIRGINIA DRIVE, Winter Garden, FL
0.07
Single-Family Home
$465,000
12/02/25
4
2.5
2,004
308 FOREST HAVEN DRIVE, Winter Garden, FL
0.11
Single-Family Home
$1,170,000
03/27/26
4
2.5
3,534
284 DONALD DRIVE, Winter Garden, FL
0.03
Single-Family Home
$1,550,000
12/10/25
4
4.5
3,438
418 COURTLEA OAKS BOULEVARD, Winter Garden, FL
0.17
Single-Family Home
$675,000
11/25/25
4
2.5
2,238
403 COURTLEA CREEK DRIVE, Winter Garden, FL
0.14
Single-Family Home
$950,000
10/08/25
5
3
2,886
753 ORANGE BELT LOOP, Winter Garden, FL
0.09
Single-Family Home
$775,000
12/12/25
4
3.5
3,074
313 COURTLEA PARK DRIVE, Winter Garden, FL
0.31
Single-Family Home
$750,000
10/28/25
5
4
3,152
716 ORANGE BELT LOOP, Winter Garden, FL
0.17
Single-Family Home
$865,000
12/19/25
4
3.5
3,145
205 TRAIL BRIDGE COURT, Winter Garden, FL
0.27
Single-Family Home
$720,000
09/17/25
3
2.5
2,405
336 COURTLEA PARK DRIVE, Winter Garden, FL
0.31
Single-Family Home
$775,000
04/16/26
4
4
2,640

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
284 DONALD DRIVE, Winter Garden, FL 34787
0.03
$1,550,000
4
4.5
3,438
Recently Sold
236 DONALD DRIVE, Winter Garden, FL 34787
0.06
$450,000
2
1
1,080
Recently Sold
290 GARY DRIVE, Winter Garden, FL 34787
0.04
$503,900
3
2
1,758
Off Market
275 VIRGINIA DRIVE, Winter Garden, FL 34787
0.07
$465,000
4
2.5
2,004
Recently Sold
772 LOOP, Winter Garden, FL 34787
0.09
$771,500
4
3.5
2,962
Off Market
753 ORANGE BELT LOOP, Winter Garden, FL 34787
0.09
$775,000
4
3.5
3,074
Recently Sold
776 ORANGE BELT LOOP, Winter Garden, FL 34787
0.10
$608,600
3
2
1,860
Off Market
777 ORANGE BELT LOOP, Winter Garden, FL 34787
0.12
$757,300
4
3
2,686
Off Market
308 FOREST HAVEN DRIVE, Winter Garden, FL 34787
0.11
$1,170,000
4
2.5
3,534
Recently Sold
412 COURTLEA OAKS BOULEVARD, Winter Garden, FL 34787
0.11
$1,207,800
4
4
3,668
Off Market
282 E NEWELL STREET LOT 57, Winter Garden, FL 34787
0.13
$345,000
-
-
-
Recently Sold
628 ORANGE BELT LOOP, Winter Garden, FL 34787
0.14
$510,000
3
2.5
1,850
Recently Sold

Local Information

  • Map ViewExplore the area around 291 Gary Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 2018
0.25 acre lot
3,167 sqft
$303/sqft

About this House

This single-family home is located at 291 Gary Dr, Winter Garden, FL. 291 Gary Dr is in Winter Garden, FL and in ZIP code 34787. This property has 4 bedrooms, 3 bathrooms and approximately 3,167 sqft of floor space. This property has a lot size of 10732 sqft and was built in 2018.
291 Gary Dr, Winter Garden, FL 34787 is a 4 bedroom, 3 bathroom, 3,167 sqft single-family home built in 2018. It last sold for $164,000 on May 12, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $959,800, with a rent estimate of $4,080/month.

Home Details for 291 Gary Dr

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2

Exterior Features

Exterior Home Features
Roof: Built Up

Property Information

Year Built
Year Built: 2018Year Updated: 1980
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 10732 sqft

Price and Tax history

DateEventPrice
May 12, 2015
Source: N/A
Sold
$164,000
Oct 17, 2006
Source: N/A
Sold
$205,000
Jan 27, 2000
Source: N/A
Sold
$85,000

Market trends in Winter Garden

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$583K
$3.33KMoM
Sale-to-List Price
98.3%
0.2%MoM
Price per sq ft
$254
$3MoM
Available listings
760
4MoM

Around this home

What Locals Say about Winter Garden

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
    Flag
  • 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
    Flag
  • 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
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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
    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
    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
    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
    Flag
  • 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
    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
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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
    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
    Flag
  • 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 291 Gary Dr

  • What is 291 Gary Dr estimated to be worth?
    Trulia's estimated value for 291 Gary Dr in Winter Garden, FL is $959,800.
  • What is the price history for 291 Gary Dr?
    291 Gary Dr in Winter Garden, FL last sold for $164,000 in May 2015.
  • Is Winter Garden a buyer's or seller's market?
    Winter Garden is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Winter Garden?
    The median sale price in Winter Garden is $583K. That is down $3.33K from the prior month.
  • Does 291 Gary Dr have air conditioning?
    Yes, 291 Gary Dr in Winter Garden, FL has air conditioning.
  • How big is the lot at 291 Gary Dr?
    The lot at 291 Gary Dr in Winter Garden, FL is about 0.25 acres (10,732 sq ft).

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