1429 Eastover Loop, Winter Garden, FL 34787
Property image
Property image
OFF MARKET

$766,500

Trulia Estimate
  • 3 Beds
  • 3.5 Baths
  • 2,378 sqft

1429 Eastover Loop, Winter Garden, FL 34787

Est. Refi. Payment $5,397/mo*
Refinance Your Home
Currently Off Market - Sold Aug 12, 2022 for $702,500

Home Value

Trulia Estimate
$767K
Since last month
Increased$13K (+1.7%)
Since last year
Increased$19K (+2.5%)
Since last sale
Increased$65K (+9.3%)
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 +133% in the last 10 years
MonthEstimated value
2026
August 2026$768K
August 2026$767K
July 2026$755K
June 2026$765K
May 2026$762K
April 2026$761K
March 2026$757K
February 2026$748K
January 2026$734K
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
1428 UNION CLUB DRIVE, Winter Garden, FL
0.05
Single-Family Home
$845,000
02/18/26
4
3.5
2,548
1016 HUNTSPOINT STREET, Winter Garden, FL
0.24
Single-Family Home
$850,000
01/05/26
3
2.5
2,421
1368 UNION CLUB DRIVE, Winter Garden, FL
0.07
Single-Family Home
$849,000
02/27/26
3
2.5
2,484
1034 HUNTSPOINT STREET, Winter Garden, FL
0.22
Single-Family Home
$770,000
11/03/25
4
3.5
2,219
1338 UNION CLUB DRIVE, Winter Garden, FL
0.08
Single-Family Home
$869,700
05/22/26
4
3.5
2,637
1087 HUNTSPOINT STREET, Winter Garden, FL
0.17
Single-Family Home
$800,000
04/01/26
3
2
1,932
744 LAKE BRIM DRIVE, Winter Garden, FL
0.22
Single-Family Home
$935,000
06/30/26
4
3.5
2,667
1024 KERSHAW DRIVE, Winter Garden, FL
0.30
Single-Family Home
$925,700
03/10/26
4
3.5
2,461
971 PAWLEY WAY, Winter Garden, FL
0.17
Single-Family Home
$775,000
11/26/25
4
2
2,106
111 LAKEVIEW RESERVE BOULEVARD, Winter Garden, FL
0.20
Single-Family Home
$646,000
02/13/26
4
2.5
2,882

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
1201 UNION CLUB DRIVE, Winter Garden, FL 34787
0.05
$1,197,500
4
3.5
2,793
Off Market
1453 UNION CLUB DRIVE, Winter Garden, FL 34787
0.05
$960,800
5
4
2,691
Off Market
1411 EASTOVER LOOP, Winter Garden, FL 34787
0.03
$642,600
3
3.5
1,937
Off Market
1049 PAWLEY WAY, Winter Garden, FL 34787
0.07
$1,277,700
4
3.5
3,259
Off Market
1043 PAWLEY WAY, Winter Garden, FL 34787
0.07
$1,223,100
4
2.5
2,683
Off Market
1031 PAWLEY WAY, Winter Garden, FL 34787
0.07
$1,017,100
3
3.5
2,822
Off Market
1224 UNION CLUB DRIVE, Winter Garden, FL 34787
0.08
$1,665,000
5
5.5
5,441
Recently Sold
1428 UNION CLUB DRIVE, Winter Garden, FL 34787
0.05
$845,000
4
3.5
2,548
Recently Sold
907 EASLEY AVENUE, Winter Garden, FL 34787
0.08
$859,000
3
2.5
2,252
For Sale
1338 UNION CLUB DRIVE, Winter Garden, FL 34787
0.08
$890,000
4
3.5
2,637
For Sale
1368 UNION CLUB DRIVE, Winter Garden, FL 34787
0.07
$849,000
3
2.5
2,484
Recently Sold
925 EASLEY AVENUE, Winter Garden, FL 34787
0.09
$1,125,000
4
3.5
2,667
For Sale

Local Information

  • Map ViewExplore the area around 1429 Eastover Loop.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2008
Living Area
2,378 sqft
Price/Sqft
$322
Parking
Garage

About this House

PARK FRONT CUSTOM MANOR HOME WITH A EUROPEAN FLAIR IN OAKLAND PARK. One of a kind, FGBC certified green Manor Home with 2,378 square feet and finishes that would rival any custom home built! Located on Eastover Loop with Reciprocity Park views from your partially screened wrap around porch and views of Lake Apopka from the rear of the home. This largest manor home in Oakland Park Home built by Castle & Cooke features 3 bedrooms and 3.5 baths plus a sunroom and a first floor balcony off a much desired mud room. The home is fully fenced giving privacy on the back and side yard. This home was recently totally renovated! With over $130,000 in updating and complete renovations. The double master setup has completely renovated en-suites including a soothing freestanding tub in the owners suite. New walk-in showers with gorgeous Italian Tiling and Full Frameless Glass Showers further enhance the full baths. Free standing sinks are in all bathrooms and the powder room. The mudroom and powder bath have been renovated with 8x8 Art Nouveau Woad Blue Tile. Renovations include but not limited to Medallion Collection Hardwood Flooring throughout the Great Room, French Country Kitchen and second floor Hallways. Lonely Days Berber Luxury Design Carpet in Silver Lining is in all bedrooms, and Country Mile Luxury Design Carpet on both staircases. French Doors leading from the great room to the spacious modern Farmhouse Country Kitchen, including a custom designed Kitchen Island, Italian Painted Backsplash and Caesarstone Primordia Quartz Counter Tops. The home also features other custom changes. Bedroom 2 has had custom shelving added and is currently being used as a den. The Bonus Room above the garage is currently being used as a second master bedroom. New appliances include 2 Rannai Natural Gas Tankless Water heaters, GE Appliances and Champagne Samsung Front Load Washer and Dryer. Energy saving features include: double pane/double hung low E windows, natural gas tankless hot water heaters, 16 SEER a/c, Icynene Spray Foam Insulation, Hardie Board Exterior Siding and a Metal Roof. HOA covers exterior painting, exterior pressure washing, roof and termite bond.
1429 Eastover Loop, Winter Garden, FL 34787 is a 3 bedroom, 4 bathroom, 2,378 sqft single-family home built in 2008. It last sold for $702,500 on Aug 12, 2022. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $766,500, with a rent estimate of $3,341/month.

Home Details for 1429 Eastover Loop

Interior Features

Heating & Cooling
Heating: ElectricAir ConditioningCooling System: CentralHeating Fuel: Electric
Levels, Entrance, & Accessibility
Stories: 2Floors: Softwood, Tile, Carpet
Interior Details
Number of Rooms: 9Types of Rooms: Dining Room
Appliances & Utilities
DishwasherDryerMicrowaveRefrigeratorWasher

Exterior Features

Exterior Home Features
Roof: MetalExterior: Other
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Property Information

Year Built
Year Built: 2008Year Updated: 2008
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 4791 sqft

Price and Tax history

DateEventPrice
Aug 12, 2022
Source: N/A
Sold
$702,500
Aug 10, 2022
Source: RE/MAX International #O6033384
Pending
$750,000
Aug 10, 2022
Source: RE/MAX International
ListingRemoved
Jul 7, 2022
Source: RE/MAX International #O6033384
Pending
$750,000
Jul 7, 2022
Source: Stellar MLS #O6033384
PendingToActive
$750,000

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
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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
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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
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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
    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
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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
    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
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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
    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
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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
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 1429 Eastover Loop

  • What is 1429 Eastover Loop estimated to be worth?
    Trulia's estimated value for 1429 Eastover Loop in Winter Garden, FL is $766,500.
  • What is the price history for 1429 Eastover Loop?
    1429 Eastover Loop in Winter Garden, FL last sold for $702,500 in August 2022.
  • 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 1429 Eastover Loop have air conditioning?
    Yes, 1429 Eastover Loop in Winter Garden, FL has air conditioning.
  • Does 1429 Eastover Loop have laundry facilities?
    Yes, 1429 Eastover Loop in Winter Garden, FL has in-unit laundry.

Explore by feature - Pet Friendly

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