1423 Eastover Loop, Winter Garden, FL 34787
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Property image
OFF MARKET

1423 Eastover Loop
Winter Garden, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,163 sqft

$989,500

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,757/mo*
Refinance Your Home

$989,500

Trulia Estimate
as of Jul 6, 2026
Est. Refi. Payment $6,757/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,163 sqft

Local Information

  • Map ViewExplore the area around 1423 Eastover Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Showings are WELCOMED, VIRTUAL tour is available. Capture the beauty of this CUSTOM, one of a kind, PARK-VIEW home in the highly sought after community of OAKLAND PARK!! This tastefully crafted home was formerly a 1st PLACE winner in the Parade of Homes. It sits on an OVERSIZED lot and features 4 bedrooms, 3.5 baths (1/2 bath connects to the patio or future pool area), DINING room, OFFICE or gathering area which includes a gas FIREPLACE and park views, WOOD floors downstairs, bamboo style laminate floors upstairs, crown molding, custom TRIM and lighting, two sets of FRENCH doors, laundry room with GRANITE, utility sink and cabinet space, backyard DECK for family fun, FENCED yard with room for a POOL, ATTACHED garage with parking space behind the garage, tankless water heaters, and so much more! Kitchen is spacious and perfect for entertaining, and includes STAINLESS appliances, gas stove, butler's pantry, TRAVERTINE counters, breakfast bar, island sink, and under cabinet lighting. MASTER suite is upstairs and features park views, two closets, dual vanity, ample light, garden TUB, shower, and private toilet. Two additional bedrooms and full bath are located near the master. The 4th bedroom or BONUS area is towards the back of the home, and includes a kitchenette with refrigerator and microwave, granite counters, and full bath. Enjoy the LAKE views from this room! UPDATES: 2 ACs (2017 & 2018), paint interior/exterior (2016), SHUTTERS, newly installed landscaping and sod in various areas. Oakland Park, previously voted '#1 community to live in' by Orlando Style Magazine. PARADE of HOMES 'Community' Winner with homes over a million. Step outside & access the 22 mile long West Orange Trail for exercising or cruise on your GOLF CART to infamous downtown historic Winter Garden. A dream come true neighborhood. Community is GOLF cart approved, certified GREEN, & features parks, playgrounds, two pools (one resort style), sunset views, & a spectacular CLUBHOUSE! Located near interstate travel, shops, and restaurants. Buyer to verify information, measurements are approximate. Capture this custom beauty before it's SOLD!!
1423 Eastover Loop, Winter Garden, FL 34787 is a 4 bedroom, 4 bathroom, 3,163 sqft single-family home built in 2008. It last sold for $647,000 on Sep 18, 2020. It is currently off market. The Trulia Estimate is $989,500, with a rent estimate of $4,054/month.

Home Highlights

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

Home Details for 1423 Eastover Loop

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood, Laminate
Interior Details
Types of Rooms: Dining Room
Appliances & Utilities
Cable ReadyDishwasherMicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Shake ShingleDeckExterior: WoodPorch
Parking & Garage
GarageParking: On Street, Garage

Property Information

Year Built
Year Built: 2008Year Updated: 2008
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 9583 sqft

Price History for 1423 Eastover Loop

DatePriceEventSource
09/18/2020$647,000Sold
Stellar MLS #O5863798
08/14/2020$669,900PendingAgent Provided
06/18/2020$669,900PriceChange
Agent Provided
05/14/2020$675,000Listed For SaleAgent Provided
08/26/2016$488,000Sold
Stellar MLS #O5399039
08/12/2016$504,000PendingAgent Provided
06/04/2016$504,000PriceChange
Agent Provided
04/19/2016$514,000PriceChange
Agent Provided
02/24/2016$524,000PriceChange
Agent Provided
01/08/2016$529,000PriceChange
Agent Provided
10/19/2015$539,000Listed For SaleAgent Provided
10/14/2008$454,000Sold
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$7,828
Assessment$793,220
Home facts updated by county records

Comparable Sales for 1423 Eastover Loop

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
111 Lakeview Reserve Blvd, Winter Garden, FL
0.19
Single-Family Home
$646,000
02/13/26
4
2.5
2,882
1338 Union Club Dr, Winter Garden, FL
0.07
Single-Family Home
$869,700
05/22/26
4
3.5
2,637
1428 Union Club Dr, Winter Garden, FL
0.06
Single-Family Home
$845,000
02/18/26
4
3.5
2,548
1368 Union Club Dr, Winter Garden, FL
0.07
Single-Family Home
$849,000
02/27/26
3
2.5
2,484
97 Desiree Aurora St, Winter Garden, FL
0.14
Single-Family Home
$565,000
08/01/25
4
2
1,853
744 Lake Brim Dr, Winter Garden, FL
0.23
Single-Family Home
$935,000
06/30/26
4
3.5
2,667
243 Zachary Wade St, Winter Garden, FL
0.32
Single-Family Home
$1,005,000
01/07/26
5
3.5
3,097
1034 Huntspoint St, Winter Garden, FL
0.24
Single-Family Home
$770,000
11/03/25
4
3.5
2,219
1006 Lake Brim Dr, Winter Garden, FL
0.28
Single-Family Home
$1,320,000
02/27/26
4
3
3,056
971 Pawley Way, Winter Garden, FL
0.18
Single-Family Home
$775,000
11/26/25
4
2
2,106

Nearby homes

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Assigned Schools

These are the assigned schools for 1423 Eastover Loop.
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
    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
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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
    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
  • 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
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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
    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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Explore by feature - Pet Friendly

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Homes for sale near 1423 Eastover Loop

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Off Market Homes Near 1423 Eastover Loop

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