421 Winding Hollow Ave, Ocoee, FL 34761
OFF MARKET

421 Winding Hollow Ave
Ocoee, FL 34761

  • 4 Beds
  • 2 Baths
  • 1,948 sqft

$493,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $3,369/mo*
Refinance Your Home

$493,400

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $3,369/mo*
Refinance Your Home
4 Beds
2 Baths
1,948 sqft

Local Information

  • Map ViewExplore the area around 421 Winding Hollow Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Immaculate! Ready to move in 4 bedrooms, 2 bathroom home in the desired gated community!!! The kitchen has been remodeled with the highest of upgrades and plenty of storage. A completely remodeled master bath and second full bath complement a large family or those who like to host visitors. New bamboo hardwood floors in the living room and the kitchen set an elevated tone, along with new carpet throughout all bedrooms and the family room. New tile in the laundry room brightens that side of the home. Freshly painted, and turnkey ready. Great school districts, close to shopping and theme parks.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

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

Home Details for 421 Winding Hollow Ave

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1

Exterior Features

Exterior Home Features
Roof: Shake Shingle
Pool
Pool
Parking & Garage
GarageParking: Garage

Property Information

Year Built
Year Built: 1995Year Updated: 1999
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 9478 sqft

Price History for 421 Winding Hollow Ave

DatePriceEventSource
07/05/2019$315,000Sold
N/A
06/03/2019$324,900Listed For SaleAgent Provided
10/06/1995$139,400Sold
N/A

Market trends in Ocoee

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$433K
$18.33KMoM
Sale-to-List Price
98.5%
0.3%MoM
Price per sq ft
$223
$3MoM
Available listings
210
3MoM
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Property Tax and Assessment

Year2024
Tax$4,681
Assessment$402,770
Home facts updated by county records

Comparable Sales for 421 Winding Hollow Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
430 Winding Hollow Ave, Ocoee, FL
0.03
Single-Family Home
$465,000
04/23/26
3
2
1,770
608 Bridge Creek Blvd, Ocoee, FL
0.16
Single-Family Home
$370,000
04/17/26
4
2
1,659
438 Darkwood Ave, Ocoee, FL
0.03
Single-Family Home
$479,900
05/01/26
4
3
1,895
325 Longshadows Ct, Ocoee, FL
0.11
Single-Family Home
$474,000
06/04/26
3
2
1,870
632 Bridge Creek Blvd, Ocoee, FL
0.16
Single-Family Home
$475,000
07/24/25
4
2
1,864
2437 Cliffdale St, Ocoee, FL
0.15
Single-Family Home
$475,000
02/27/26
3
2
1,778
700 Little Hampton Ln, Gotha, FL
0.20
Single-Family Home
$639,750
10/20/25
4
2
2,486
814 Windergrove Ct, Ocoee, FL
0.39
Single-Family Home
$525,000
03/20/26
4
2
1,862
811 Huntsville Rd, Gotha, FL
0.36
Single-Family Home
$590,000
12/09/25
4
2
2,436
466 Drexel Ridge Cir, Ocoee, FL
0.29
Single-Family Home
$434,000
09/23/25
5
2.5
2,324

Nearby homes

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Assigned Schools

These are the assigned schools for 421 Winding Hollow Ave.
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 Ocoee

At least 340 Trulia users voted on each feature.

  • 89 % Say there are sidewalks

  • 88 % Say it's dog friendly

  • 86 % Say car is needed

  • 79 % Say parking is easy

  • 78 % Say yards are well-kept

  • 77 % Say there's holiday spirit

  • 70 % Say it's quiet

  • 70 % Say kids play outside

  • 69 % Say streets are well-lit

  • 66 % Say people would walk alone at night

  • 51 % Say neighbors are friendly

  • 51 % Say it's walkable to grocery stores

  • 49 % Say they plan to stay for at least 5 years

  • 40 % Say there's wildlife

  • 34 % Say it's walkable to restaurants

  • 30 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Rose4andy
    "Community Market and lots of events every week Clean and well organized city hall is neat and charming"
    0
    Flag
  • Analisa Doczekalski
    "Becoming a very busy area with traffic especially around drop off and pick up time. Lots of commercial building going up causing daily trucks on the road keeping one lane traffic on roads back. "
    0
    Flag
  • Queenjai247
    "Love it here! Very safe for the children no complaints at all from the cleanliness or neighborliness."
    0
    Flag
  • Mdshumate1
    "No public transport is available - I drive my personal vehicle. The roads are well maintained and traffic flows smoothly. "
    1
    Flag
  • Mike D.
    "The neighborhood is great feel extra safe and everyone is very nice. I would recommend it to anyone!!!"
    5
    Flag
  • Neysha C.
    "my neighborhood had great success to public transportation and also commute to downtown and would like to buy a house around here "
    0
    Flag
  • Tamyres V.
    "People walk with their dogs everyday, and they always seemed friendly and happy doing it....... dog "
    4
    Flag
  • Sidebyeachinc
    "Great community. Safe and good value for real estate Everything is close and convenient. Great schools and activities to do. "
    0
    Flag
  • Jamalreece
    "Founders Day is celebrated every year and families have been here for generations. Can’t complain with good food options like authentic Mexican and Jamaican cuisines "
    1
    Flag
  • Jose.deleon0322
    "Awesome area. Many stores and restaurants withing short distance and close to the highway. I recommend it. "
    2
    Flag
  • Bert K.
    "i like this neighborhoods it's myself home we all are friends and we helped one anotherhhggfghjjjhffgu"
    0
    Flag
  • Ann W.
    "Commuting is easy. Most restaurants and shopping areas are less than five miles. You can get to downtown Orlando in about 25 minutes. All major attractions are easily accessible."
    0
    Flag
  • Lisa S.
    "Family fun block parties a lot of trees parks pool friendly neighbors Santa rides through with the fire department "
    0
    Flag
  • Eric J. C.
    "There is a variety of shopping choices nearby good schools and major crime is very low. It is near the 408 the turnpikes day 429. Downtown isn’t far. "
    0
    Flag
  • Eric J. C.
    "It’s quiet and safe here. Quite clean. Good schools nearby. Shopping and medical clinics are close. "
    0
    Flag
  • Carrollann B.
    "Child friendly with parks, lakeview with shallow water, playgrounds, good schools, library close by, churches, hospital,pumpkin patches, blueberry and fruit picking and centralized grocery stores/supermarkets for healthy eating"
    0
    Flag
  • David S
    "Tucked away and in a space where downtown, midtown, I4, and the tolls are all accessible is Ocoee. A quiet and safe space for new homeowners to grow and established families can thrive. "
    0
    Flag
  • Martin29usa
    "I live here, good area many shopping center, easy the get the high way like I4,408,429 and turnpike "
    0
    Flag
  • Holleyparis
    "Convenient to most major highways and fairly central to most of major locations in the Orlando area. "
    0
    Flag
  • Courtney A.
    "There are many parks for the kids to enjoy in Ocoee. The west orange trail is also easily accessible, and nicely shaded. "
    0
    Flag
  • Courtney A.
    "We have an Annual get together and movie nights in the neighborhood. Nice neighbors. Community is growing more, and the downtown has been newly renovated. Excited for the growing Ocoee. "
    0
    Flag
  • Attilahgdhdhdhdhdhdhsj Verdell
    "Size matters and I see the difference in the water bill . Well kept lawn. The community seems to keep the outside well maintained"
    0
    Flag
  • Tb_waller
    "I love Ocoee and am looking to buy a home here. It is a great neighborhood with really good schools."
    0
    Flag
  • Sam P. .
    "Unless you live in a neighborhood subdivision of kids with a large population of children, it’s a sad place to be for kids and sort of unsafe for kids to walk or play outside. It’s a decently sized town that is trying to clean up its act. The mall in town is terribly unsafe. This isn’t the type of town that kids can go out and explore by themselves "
    0
    Flag
  • Kerrie L.
    "My neighborhood is very pretty. The commute seems to be very good. I do run into traffic near Gotha. But, that's only during high traffic times. Other than that I think it's beautiful. "
    0
    Flag
  • Well
    "Very quietly place and very good schools near to my house. Good neighborhood and good access. My daughter loves her school."
    0
    Flag
  • CP
    "It's a nice and safe place. Mall,stores and hospital are very close. It's a family friendly place to live but parking is horrible."
    0
    Flag
  • Clewisjr1969
    "helping out in the community is it and how it works. neighborhood is very special with a lot nationalities and kids and vary good school."
    0
    Flag
  • Zahmoulemnaben
    "hi. I like the area it's very quiet and nice. everything is too close restaurant, shopping area, banks, hospital"
    0
    Flag
  • Nic T.
    "It was affordable but it is high crime and noisy. Lots of stray cats and a few stay people. Residents use my street like it was a race track. Loud and unsafe"
    1
    Flag
  • Clare B.
    "It’s a lovely gated area with a lovely lake. The roads are clear and the surrounding gardens are well kept "
    0
    Flag
  • Jason Bailey
    "It is a beautiful, new, and quiet neighborhood far away from I4 traffic. Lots of kids and families throughout the neighborhood."
    1
    Flag
  • Metaltek92
    "My neighbors don't walk their dogs, they run wild here with wild cats! The wild animals around keep the cat population under 16 cats!"
    0
    Flag
  • Beccabecca777
    "Block parties friendly neighborhood lots of kids, dogs and very quite NeighborHood. Friendly neighbors no crime"
    0
    Flag
  • Patricia S.
    "i see dogs all the time, walking with owners. there are many vet clinics around, some are really affordable."
    0
    Flag

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Apartments for Rent

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Explore by feature - Pet Friendly

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Explore by feature - Pool

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Explore by feature - Outdoor Space

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Homes for sale near 421 Winding Hollow Ave

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Off Market Homes Near 421 Winding Hollow Ave

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421 Winding Hollow Ave, Ocoee, FL 34761 is a 4 bedroom, 2 bathroom, 1,948 sqft single-family home built in 1995. This property is not currently available for sale. 421 Winding Hollow Ave was last sold on Jul 5, 2019 for $315,000. The current Trulia Estimate for 421 Winding Hollow Ave is $493,400.