555 Jackson St, Winter Garden, FL 34787
OFF MARKET

555 Jackson St
Winter Garden, FL 34787

  • 2,059 sqft
2,059 sqft

Home Value

Learn more about this home's value by checking out the value of nearby homes and how much similar homes have sold for.

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
136 W MORGAN STREET LOT 23, Winter Garden, FL
0.49
Lot/Land
$105,000
10/17/25
-
-
227 W CYPRESS STREET LOT 22, Winter Garden, FL
0.31
Lot/Land
$155,000
05/21/26
-
-
143 W MORGAN STREET LOT 3, Winter Garden, FL
0.47
Lot/Land
$150,001
11/17/25
-
-
244 W STORY ROAD LOT 1, Winter Garden, FL
0.33
Lot/Land
$470,000
01/05/26
-
-
244 W STORY ROAD, Winter Garden, FL
0.33
Lot/Land
$470,000
01/05/26
-
-
W VINING STREET LOT 7, Winter Garden, FL
0.46
Lot/Land
$247,500
10/23/25
-
-
W VINING STREET, Winter garden, FL
0.46
Lot/Land
$247,500
10/24/25
-
-
1359 AVALON ROAD, Winter Garden, FL
0.91
Lot/Land
$65,000
02/12/26
-
-
1359 AVALON ROAD LOT 8, Winter Garden, FL
0.91
Lot/Land
$65,000
02/12/26
-
-
1351 AVALON ROAD LOT 7, Winter Garden, FL
0.91
Lot/Land
$105,000
02/12/26
-
-

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
829 PAMELA AVENUE, Winter Garden, FL 34787
0.01
$429,300
4
2
1,492
Off Market
809 PAMELA AVENUE LOT 23, Winter Garden, FL 34787
0.03
-
-
-
-
Off Market
761 PAMELA AVENUE, Winter Garden, FL 34787
0.05
$475,800
3
3
1,330
Off Market
1035 Highgate Blvd #18, Winter Garden, FL 34787
0.07
$85,000
3
2
1,176
For Sale
740 Queensbury Loop #213, Winter Garden, FL 34787
0.08
$80,000
2
2
1,680
For Sale
751 PAMELA AVENUE, Winter Garden, FL 34787
0.07
$433,300
3
2
1,394
Off Market
745 Queensbury Loop #222, Winter Garden, FL 34787
0.09
$95,000
2
2
1,680
For Sale
1065 Highgate Blvd #21, Winter Garden, FL 34787
0.09
$169,900
2
2
1,344
For Sale
509 WESTPOINT GARDEN CIRCLE, Winter Garden, FL 34787
0.06
$318,500
3
2.5
1,558
Off Market
810 FOSTER AVENUE, Winter Garden, FL 34787
0.09
$381,700
3
2
1,188
Off Market
765 White Chapel Rd #307, Winter Garden, FL 34787
0.15
$65,000
2
2
1,352
For Sale
442 WESTPOINT GARDEN CIRCLE, Winter Garden, FL 34787
0.09
$334,000
3
2.5
1,588
Off Market

Local Information

  • Map ViewExplore the area around 555 Jackson St.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Lot/Land
Year Built
2018
Living Area
2,059 sqft

About this House

Ready for plans! This site will accommodate a duplex and is a corner lot! Owner and Broker have contractors in place for blueprints and bids for building. Come build an income producer today!
555 Jackson St, Winter Garden, FL 34787 is a 2,059 sqft lot/land built in 2018. It last sold for $28,000 on Aug 12, 2015. It is currently off market. The Trulia Estimate rent is $1,703/month.

Home Details for 555 Jackson St

Interior Features

Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: Other

Property Information

Year Built
Year Built: 2018
Property Type / Style
Property Type: Lot LandArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 9274 sqft

Price and Tax history

DateEventPrice
Aug 12, 2015
Source: N/A
Sold
$28,000
Nov 24, 2013
Source: Agent Provided
ListingRemoved
$34,000
Sep 26, 2013
Source: Agent Provided
PriceChange
$34,000
Price decreased by 13%
Jun 4, 2013
Source: Agent Provided
Listed For Sale
$39,000

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
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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
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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
    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 ."
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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
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  • 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
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  • 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
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  • 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
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  • 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
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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! "
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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"
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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
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  • 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."
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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
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  • 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"
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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
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  • 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."
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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."
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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
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  • 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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Apartments for Rent

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Homes for sale near 555 Jackson St

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Off Market Homes Near 555 Jackson St

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Frequently asked questions about 555 Jackson St

  • What is the price history for 555 Jackson St?
    555 Jackson St in Winter Garden, FL last sold for $28,000 in August 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.
  • What do residents say about Winter Garden?
    Residents describe Winter Garden, FL as dog-friendly, pedestrian-friendly, and easy to park in. See recently sold homes in Winter Garden, FL.