20 E DIVISION STREET, Winter Garden, FL 34787
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Property image
FOR SALE
3D VIEW
0.3 ACRES

20 E DIVISION STREET
Winter Garden, FL 34787

  • 4 Beds
  • 3 Baths
  • 2,729 sqft (on 0.30 acres)

$1,080,000

Original price: $1,120,000
Est. Mortgage $7,470/mo*
Get Pre-Qualified

$1,080,000

Original price: $1,120,000
Est. Mortgage $7,470/mo*
Get Pre-Qualified
4 Beds
3 Baths
2,729 sqft
(on 0.30 acres)

Home Highlights

Parking
1 Car Garage
Outdoor
Pool
Climate Control
Central & Central Air
HOA
None
Price/Sqft
$396
Listed
74 days ago

Local Information

  • Map ViewExplore the area around 20 E DIVISION STREET.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Appraisal in hand! Welcome to one of Winter Garden's most remarkable custom transformations. This wasn't a flip—it was the owner's forever dream home. Originally built in 1959 and completely reimagined in 2023 and 2026. This extraordinary residence has undergone an extensive renovation and expansion, creating a truly one-of-a-kind property just minutes from Historic Downtown Winter Garden and Plant Street. Offering 2,729 square feet of beautifully designed living space, this 4-bedroom, 3-bathroom home showcases exceptional craftsmanship, thoughtful design, and luxury finishes throughout. In 2026, the owners completed a stunning expansion that includes an ultra-luxury primary suite designed as a private retreat. The spa-inspired custom bathroom features premium finishes, a private sauna, and a level of comfort rarely found at this price point. The heart of the home features open-concept living spaces filled with natural light, designer finishes, and seamless flow for everyday living and entertaining. Step outside to your private backyard oasis featuring a brand-new custom pool completed in 2026, creating the perfect setting for relaxing weekends and unforgettable gatherings. Major improvements include a 2026 HVAC system, 2026 luxury primary suite addition, 2026 custom pool, 2022 plumbing, 2022 electrical, 2018 roof, and all new windows installed in 2018, providing peace of mind for years to come. Every inch of this home tells the story of a family who spared no expense creating their dream home. Now, that dream can become yours. Schedule your private showing today!!!
Last check for updates: about 2 hours ago
Listing Provided by: Liz Boyce, (407) 784-4919
CHARLES RUTENBERG REALTY ORLANDO, (407) 622-2122
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6413659
Also Listed on Stellar MLS.
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Home Details for 20 E DIVISION STREET

Interior Features

Interior Details
Number of Rooms: 3Types of Rooms: Primary Bedroom, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2729 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity AvailableAppliances: Bar Fridge, Convection Oven, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer, Wine RefrigeratorDishwasherDisposalDryerLaundry: Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: CentralHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Family RoomHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Luxury Vinyl, Marble, Porcelain TileCommon Walls: Corner Unit
Levels, Entrance, & Accessibility
Stories: 1Levels: OneFloors: Luxury Vinyl, Marble, Porcelain Tile
View
No View

Exterior Features

Exterior Home Features
Roof: ShingleExterior: Garden, Private Yard, Rain Gutters, SaunaFoundation: SlabGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Garage Attached
Pool
Pool: In GroundPool
Frontage
Road Surface Type: AsphaltNot on Waterfront
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 48Days on Market: 74

Property Information

Year Built
Year Built: 1959
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence
Building
Construction Materials: ConcreteNot a New ConstructionNo Additional Parcels
Property Information
Condition: CompletedParcel Number: 142227938801010

Price & Status

Price
List Price: $1,080,000Price Per Sqft: $396

Active Status

MLS Status: Active

Media

Location

Direction & Address
City: WINTER GARDENCommunity: WINTER GARDEN SHORES FIRST ADD

Agent Information

Listing Agent
Listing ID: O6413659

Building

Building Area
Building Area: 3435 Square Feet

Community

Not Senior Community

HOA

Association for this Listing: Orlando RegionalNo HOAHOA Fee: No HOA Fee

Lot Information

Lot Area: 0.30 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6413659Showing Advance Notice: 24Showing Requirements: 24 Hour Notice, Appointment OnlyUniversal Property Id: US-12095-N-142227938801010-R-N

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 "
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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 ."
    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
    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
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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
    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
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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
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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

Home Value

Trulia Estimate
$1.04M
Since last month
Increased$1K (+0.1%)
Since last year
Increased$306K (+41.6%)
Since last sale
Increased$293K (+39%)
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 +293% in the last 10 years
MonthEstimated value
2026
August 2026$1.04M
July 2026$1.04M
June 2026$1.09M
May 2026$799K
April 2026$799K
March 2026$769K
February 2026$747K
January 2026$724K
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
426 N BOYD STREET, Winter Garden, FL
0.13
Single-Family Home
$775,000
12/08/25
3
2.5
2,637
515 N BOYD STREET, Winter Garden, FL
0.10
Single-Family Home
$825,000
02/04/26
5
4
3,152
336 COURTLEA PARK DRIVE, Winter Garden, FL
0.34
Single-Family Home
$775,000
04/16/26
4
4
2,640
423 N MAIN STREET, Winter Garden, FL
0.06
Single-Family Home
$655,000
09/26/25
3
2
1,668
405 COURTLEA PARK DRIVE, Winter Garden, FL
0.35
Single-Family Home
$775,000
09/30/25
4
4
2,686
213 W TILDEN STREET, Winter Garden, FL
0.37
Single-Family Home
$750,000
05/18/26
4
2
2,151
418 COURTLEA OAKS BOULEVARD, Winter Garden, FL
0.48
Single-Family Home
$675,000
11/25/25
4
2.5
2,238
403 COURTLEA CREEK DRIVE, Winter Garden, FL
0.43
Single-Family Home
$950,000
10/08/25
5
3
2,886
308 FOREST HAVEN DRIVE, Winter Garden, FL
0.38
Single-Family Home
$1,170,000
03/27/26
4
2.5
3,534

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
506 N DILLARD STREET, Winter Garden, FL 34787
0.07
$758,500
3
3.5
2,241
Off Market
423 N MAIN STREET, Winter Garden, FL 34787
0.06
$653,400
3
2
1,668
Off Market
515 N BOYD STREET, Winter Garden, FL 34787
0.10
$825,000
5
4
3,152
Recently Sold
501 N DILLARD STREET, Winter Garden, FL 34787
0.10
$988,600
4
3.5
3,352
Off Market
519 N DILLIARD STREET LOT 4, Winter Garden, FL 34787
0.11
-
-
-
-
Off Market
208 SURPRISE DRIVE, Winter Garden, FL 34787
0.14
$810,200
3
2.5
2,577
Off Market
426 N BOYD STREET, Winter Garden, FL 34787
0.13
$775,000
3
2.5
2,637
Recently Sold
232 SURPRISE DRIVE, Winter Garden, FL 34787
0.14
$907,100
4
3.5
3,464
Off Market
226 SURPRISE DRIVE, Winter Garden, FL 34787
0.14
$848,600
4
3.5
2,914
Off Market
214 SURPRISE DRIVE, Winter Garden, FL 34787
0.14
$901,100
4
3.5
3,464
Off Market
427 N LAKEVIEW AVENUE, Winter Garden, FL 34787
0.15
$477,800
4
2
1,781
Off Market

Price and Tax history

DateEventPrice
Jul 23, 2026
Source: Stellar MLS #O6413659
PriceChange
$1,080,000
Price decreased by 4%
Jun 26, 2026
Source: Stellar MLS #O6413659
PriceChange
$1,120,000
Price decreased by 3%
Jun 5, 2026
Source: Stellar MLS #O6413659
Listed For Sale
$1,149,000
Aug 1, 2024
Source: Stellar MLS #O6192153
Sold
$750,000
Jul 16, 2024
Source: Stellar MLS #O6192153
Pending
$810,000

LGBTQ Local Legal Protections

Liz Boyce, CHARLES RUTENBERG REALTY ORLANDO, (407) 622-2122
Agent Phone: (407) 784-4919

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Frequently asked questions about 20 E DIVISION STREET

  • What is the estimated monthly payment for 20 E DIVISION STREET?
    Based on a $1,080,000 list price with 20% down at today's rates, the estimated monthly payment for 20 E DIVISION STREET in Winter Garden, FL is approximately $7,624 (about $5,632 principal & interest, $1,917 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 20 E DIVISION STREET compare to homes in Winter Garden?
    20 E DIVISION STREET in Winter Garden, FL is listed at $1,080,000, about 85% above the $583K median sale price in Winter Garden.
  • What do residents say about Winter Garden?
    Residents describe Winter Garden, FL as dog-friendly, pedestrian-friendly, and easy to park in. See homes for sale in Winter Garden, FL.
  • What are the closest schools to 20 E DIVISION STREET?
    The closest schools to 20 E DIVISION STREET in Winter Garden, FL are Dillard Street Elementary School (Pre-K, rated 5/10), Lakeview Middle School (rated 4/10), West Orange High School (rated 7/10).
  • Does 20 E DIVISION STREET have air conditioning?
    Yes, 20 E DIVISION STREET in Winter Garden, FL has air conditioning.
  • Does 20 E DIVISION STREET have a pool?
    Yes, 20 E DIVISION STREET in Winter Garden, FL has a pool.
20 E DIVISION STREET, Winter Garden, FL 34787 is a 4 bedroom, 3 bathroom, 2,729 sqft single-family home built in 1959. This property is currently available for sale and was listed by Stellar MLS on Jun 5, 2026. The MLS # for this home is MLS# O6413659.