445 Winding Hollow Ave, Ocoee, FL 34761
OFF MARKET

$531,800

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,483 sqft

445 Winding Hollow Ave, Ocoee, FL 34761

Est. Refi. Payment $3,719/mo*
Refinance Your Home
Currently Off Market - Sold Jan 21, 2011 for $205,000

Home Value

Trulia Estimate
$532K
Since last month
Decreased$1K (-0.2%)
Since last year
Increased$6K (+1.1%)
Since last sale
Increased$326K (+158.9%)
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 +89% in the last 10 years
MonthEstimated value
2026
August 2026$531K
July 2026$532K
June 2026$535K
May 2026$535K
April 2026$531K
March 2026$528K
February 2026$525K
January 2026$516K
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
438 DARKWOOD AVENUE, Ocoee, FL
0.03
Single-Family Home
$479,900
05/01/26
4
3
1,895
513 DARKWOOD AVENUE, Ocoee, FL
0.09
Single-Family Home
$590,900
07/16/26
4
2.5
2,396
430 WINDING HOLLOW AVENUE, Ocoee, FL
0.03
Single-Family Home
$465,000
04/23/26
3
2
1,770
608 BRIDGE CREEK BOULEVARD, Ocoee, FL
0.14
Single-Family Home
$370,000
04/17/26
4
2
1,659
466 DREXEL RIDGE CIRCLE, Ocoee, FL
0.29
Single-Family Home
$434,000
09/23/25
5
2.5
2,324
2401 CLIFFDALE STREET, Ocoee, FL
0.09
Single-Family Home
$435,000
08/17/26
3
2
1,666
325 LONGSHADOWS COURT, Ocoee, FL
0.13
Single-Family Home
$474,000
06/04/26
3
2
1,870
2437 CLIFFDALE STREET, Ocoee, FL
0.15
Single-Family Home
$475,000
02/27/26
3
2
1,778
3345 FURLONG WAY, Gotha, FL
0.32
Single-Family Home
$545,000
01/15/26
5
2.5
2,433
700 LITTLE HAMPTON LANE, Gotha, FL
0.18
Single-Family Home
$639,750
10/20/25
4
2
2,486

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
430 WINDING HOLLOW AVENUE, Ocoee, FL 34761
0.03
$465,000
3
2
1,770
Recently Sold
438 DARKWOOD AVENUE, Ocoee, FL 34761
0.03
$479,900
4
3
1,895
Recently Sold
489 BRIDGE CREEK BOULEVARD, Ocoee, FL 34761
0.07
$489,800
3
2
1,551
Off Market
412 BRIDGE CREEK BOULEVARD, Ocoee, FL 34761
0.09
$462,100
3
2
1,810
Off Market
513 DARKWOOD AVENUE, Ocoee, FL 34761
0.09
$590,900
4
2.5
2,396
Recently Sold
2404 CLIFFDALE STREET, Ocoee, FL 34761
0.08
$568,600
5
2.5
2,293
Off Market
530 BRIDGE CREEK BOULEVARD, Ocoee, FL 34761
0.12
$460,300
3
2
1,536
Off Market
2401 CLIFFDALE STREET, Ocoee, FL 34761
0.09
$435,000
3
2
1,666
Recently Sold
345 BRIDGE CREEK BLVD, Ocoee, FL 34761
0.11
$500,600
4
2
1,938
Off Market
620 BRIDGE CREEK BOULEVARD, Ocoee, FL 34761
0.14
$483,700
4
2
1,988
Off Market
632 BRIDGE CREEK BOULEVARD, Ocoee, FL 34761
0.14
$470,000
4
2
1,864
Off Market

Local Information

  • Map ViewExplore the area around 445 Winding Hollow Ave.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1995
Living Area
2,483 sqft
Price/Sqft
$214
Parking
Garage

About this House

This is a Real Estate-Owned (REO)/post-foreclosure home owned by a bank. Offers significantly less than market value are often accepted.
445 Winding Hollow Ave, Ocoee, FL 34761 is a 4 bedroom, 3 bathroom, 2,483 sqft single-family home built in 1995. It last sold for $205,000 on Jan 21, 2011. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $531,800, with a rent estimate of $3,093/month.

Home Details for 445 Winding Hollow Ave

Interior Features

Heating & Cooling
Heating: Forced AirCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Exterior Features

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

Property Information

Year Built
Year Built: 1995Year Updated: 1998
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 7663 sqft

Price and Tax history

DateEventPrice
Jan 21, 2011
Source: Stellar MLS #O5020025
Sold
$205,000
Oct 18, 2010
Source: N/A
Sold
$105,000
Oct 8, 2010
Source: Agent Provided
PriceChange
$162,000
Price increased by 0%
Aug 20, 2010
Source: Agent Provided
PriceChange
$0
Price decreased by 100%
Aug 7, 2010
Source: Agent Provided
PriceChange
$162,000
Price decreased by 10%

Market trends in Ocoee

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$419K
$10.67KMoM
Sale-to-List Price
99.2%
Price per sq ft
$215
$6MoM
Available listings
188
6MoM

Around this home

What Locals Say about Ocoee

At least 341 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 kids play outside

  • 69 % Say it's quiet

  • 69 % Say streets are well-lit

  • 65 % 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.
  • Smoynihan51
    "Generally people seem to like dogs !"
    0
    Flag
  • 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

LGBTQ Local Legal Protections

Frequently asked questions about 445 Winding Hollow Ave

  • What is 445 Winding Hollow Ave estimated to be worth?
    Trulia's estimated value for 445 Winding Hollow Ave in Ocoee, FL is $531,800.
  • What is the price history for 445 Winding Hollow Ave?
    445 Winding Hollow Ave in Ocoee, FL last sold for $205,000 in January 2011.
  • Is Ocoee a buyer's or seller's market?
    Ocoee is currently a balanced market, based on recent for-sale activity.
  • What's the median sale price in Ocoee?
    The median sale price in Ocoee is $419K. That is down $10.67K from the prior month.
  • Does 445 Winding Hollow Ave have air conditioning?
    Yes, 445 Winding Hollow Ave in Ocoee, FL has air conditioning.
  • How big is the lot at 445 Winding Hollow Ave?
    The lot at 445 Winding Hollow Ave in Ocoee, FL is about 0.18 acres (7,663 sq ft).

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