407 Macchi Ave, Oakland, FL 34787
OFF MARKET

407 Macchi Ave
Oakland, FL 34787

  • 5 Beds
  • 4 Baths
  • 3,344 sqft (on 0.29 acres)

$877,800

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $6,044/mo*
Refinance Your Home

$877,800

Trulia Estimate
as of May 24, 2026
Est. Refi. Payment $6,044/mo*
Refinance Your Home
5 Beds
4 Baths
3,344 sqft
(on 0.29 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

You will LOVE this 'Move In Ready' David Weekly home in the Historic and Charming Little Town of Oakland. This home has many upgrades such as hardwood floors, stainless appliances, wine cooler, plantation shutters, granite counters, crown mouldings and designer tile. It is tastefully decorated, very clean and well maintained. The private screen enclosure and patio are perfect for entertaining and overlooks a wooded area with no neighbors behind you. The oversize pool (33x14) and spa( 7.5x6.5) are solar and propane heated and kept clean by a salt chlorinator. The home has 5 bedrooms and 4 full baths. The bonus room upstairs has one of the baths so it could be used as a bedroom, game room or media center. The 3 car garage will provide plenty of space for all your toys! Walk one street over and you are on the West Orange Trail and less than 2 miles to the Winter Garden Historic Area and Plant Street Farmers Market where you will enjoy shopping, dining and entertainment! Walk to Oakland Avenue Charter School!
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
No Info

Home Details for 407 Macchi Ave

Interior Features

Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Interior Details
Types of Rooms: Walk In Closet, Dining Room
Appliances & Utilities
MicrowaveRefrigerator
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: CompositionExterior: Stucco
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2005Year Updated: 2005
Property Type / Style
Property Type: Single Family HomeArchitecture: Contemporary

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 407 Macchi Ave

DatePriceEventSource
05/17/2017$423,000Sold
N/A
05/12/2017$429,000PendingAgent Provided
05/12/2017$429,000Listed For SaleAgent Provided
04/08/2017$429,000ListingRemovedAgent Provided
04/05/2017$429,000PriceChange
Agent Provided
04/03/2017$439,500PriceChange
Agent Provided
03/19/2017$449,500Listed For SaleAgent Provided
12/12/2013$394,900Sold
N/A
10/24/2013$399,000PriceChange
Agent Provided
09/10/2013$399,900PriceChange
Agent Provided
08/04/2013$449,900PriceChange
Agent Provided
07/30/2013$459,900Listed For SaleAgent Provided
01/12/2006$396,800Sold
N/A
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$7,050
Assessment$654,513
Home facts updated by county records

Comparable Sales for 407 Macchi Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
413 Macchi Ave, Oakland, FL
0.06
Single-Family Home
$840,000
08/29/25
4
3
3,290
410 E Gulley Ave, Oakland, FL
0.12
Single-Family Home
$604,000
09/19/25
5
3
2,458
1180 Riverway Dr, Oakland, FL
0.03
Single-Family Home
$990,900
07/09/25
4
3.5
2,796
501 E Oakland Ave, Oakland, FL
0.24
Single-Family Home
$850,000
04/06/26
4
3.5
3,448
1143 Bulwark Oaks Ln, Oakland, FL
0.10
Single-Family Home
$1,159,532
09/26/25
5
4.5
4,436
70 Millholland St, Oakland, FL
0.27
Single-Family Home
$865,000
07/25/25
5
3
2,534
1126 Riverway Dr, Oakland, FL
0.10
Single-Family Home
$1,000,000
07/15/25
4
3
2,711
1096 Riverway Dr, Winter Garden, FL
0.16
Single-Family Home
$1,575,000
01/23/26
4
3.5
4,171
1185 Wilder Oaks Way, Oakland, FL
0.10
Single-Family Home
$999,000
02/17/26
4
3.5
2,789
1207 Ridge Lake Way, Oakland, FL
0.26
Single-Family Home
$1,700,000
04/09/26
5
3.5
3,909

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 407 Macchi 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 Winter Garden

At least 510 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

  • 60 % 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.
  • 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
    Flag
  • 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
    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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • 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
    Flag
  • Tony S.
    "I work 8 miles from my home. I am fortunate to live near my work. Disney is a huge employer in the area."
    0
    Flag
  • 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
    Flag
  • 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

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature

Homes for sale near 407 Macchi Ave

Skip to last item
Skip to first item

Off Market Homes Near 407 Macchi Ave

Skip to last item
Skip to first item

Homes for rent near 407 Macchi Ave

Skip to last item
Skip to first item
407 Macchi Ave, Oakland, FL 34787 is a 5 bedroom, 4 bathroom, 3,344 sqft single-family home built in 2005. This property is not currently available for sale. 407 Macchi Ave was last sold on May 17, 2017 for $423,000. The current Trulia Estimate for 407 Macchi Ave is $877,800.