400 Macchi Ave, Oakland, FL 34787
Property image
Property image
OFF MARKET

400 Macchi Ave
Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,454 sqft (on 0.29 acres)

$812,500

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $5,574/mo*
Refinance Your Home

$812,500

Trulia Estimate
as of Jul 12, 2026
Est. Refi. Payment $5,574/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,454 sqft
(on 0.29 acres)

Local Information

  • Map ViewExplore the area around 400 Macchi Ave.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Set in the small town of Oakland, Florida, this two-story home adds charm and beauty to a community full of history. Covered porches in the front and back provide lovely opportunities to socialize and enjoy nature. The backyard overlooks the 20+ mile West Orange Trail, perfect for a relaxing stroll, vigorous exercise, or as a scenic path that can lead you to Oakland Nature Preserve or downtown Winter Garden. Indoors, the layout was thoughtfully created with both privacy and togetherness in mind. Downstairs holds all common areas, the master suite/bathroom, guest half bathroom, laundry room, and a two-car side-loaded garage. Upstairs holds three bedrooms, two bathrooms, and an open loft with attached workspace. Lovely architectural details were added such as two-story ceilings, perfect window placements for natural lighting and view, and indoor/outdoor columns to enhance this home's decorative style. Tile, stunning wood laminate, and comfortable carpeting can be seen throughout the interior, enhancing style and versatility. The community of Winters Landing is located near popular roadways: West Colonial Dr and FL Turnpike/Central Florida Interchanges. Schedule a tour today and come see all this property offers.
400 Macchi Ave, Oakland, FL 34787 is a 4 bedroom, 4 bathroom, 3,454 sqft single-family home built in 2006. It last sold for $415,000 on Sep 7, 2018. It is currently off market. The Trulia Estimate is $812,500, with a rent estimate of $4,337/month.

Home Highlights

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

Home Details for 400 Macchi Ave

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Interior Details
Types of Rooms: Walk In Closet, Dining Room, Family Room, Master Bath, Office
Appliances & Utilities
DishwasherDisposalMicrowaveRefrigerator
Levels, Entrance, & Accessibility
Floors: Tile, Carpet

Exterior Features

Exterior Home Features
Roof: Shake ShingleExterior: Stucco
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 2006Year Updated: 2006
Property Type / Style
Property Type: Single Family HomeArchitecture: Other

Community

Units in Building: 1

Lot Information

Lot Area: 0.29 acres

Price History for 400 Macchi Ave

DatePriceEventSource
09/07/2018$415,000Sold
N/A
07/18/2018$420,000Listed For SaleAgent Provided
01/31/2015$368,500ListingRemovedAgent Provided
10/07/2014$368,500PriceChange
Agent Provided
08/02/2014$373,500PriceChange
Agent Provided
06/19/2014$378,900PriceChange
Agent Provided
04/09/2014$384,900Listed For SaleAgent Provided
04/10/2006$356,400Sold
N/A

Market trends in Oakland

Last updated June 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
28
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2024
Tax$6,622
Assessment$640,004
Home facts updated by county records

Comparable Sales for 400 Macchi Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
413 Macchi Ave, Oakland, FL
0.11
Single-Family Home
$840,000
08/29/25
4
3
3,290
505 E Gulley Ave, Winter Garden, FL
0.20
Single-Family Home
$850,000
07/01/26
4
3.5
3,399
410 E Gulley Ave, Oakland, FL
0.14
Single-Family Home
$604,000
09/19/25
5
3
2,458
501 E Oakland Ave, Oakland, FL
0.25
Single-Family Home
$850,000
04/06/26
4
3.5
3,448
8 Winters Landing Dr, Oakland, FL
0.28
Single-Family Home
$850,000
05/27/26
4
3
2,850
1126 Riverway Dr, Oakland, FL
0.16
Single-Family Home
$1,000,000
07/15/25
4
3
2,711
100 Demens St, Oakland, FL
0.20
Single-Family Home
$950,000
09/23/25
4
3
3,025
70 Millholland St, Oakland, FL
0.27
Single-Family Home
$865,000
07/25/25
5
3
2,534
1096 Riverway Dr, Winter Garden, FL
0.21
Single-Family Home
$1,575,000
01/23/26
4
3.5
4,171
1143 Bulwark Oaks Ln, Oakland, FL
0.12
Single-Family Home
$1,159,532
09/26/25
5
4.5
4,436

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 400 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 Oakland

At least 12 Trulia users voted on each feature.

  • 100 % Say yards are well-kept

  • 100 % Say it's dog friendly

  • 93 % Say there's holiday spirit

  • 93 % Say car is needed

  • 92 % Say there are sidewalks

  • 85 % Say kids play outside

  • 84 % Say it's quiet

  • 83 % Say there's wildlife

  • 79 % Say parking is easy

  • 79 % Say they plan to stay for at least 5 years

  • 67 % Say streets are well-lit

  • 63 % Say people would walk alone at night

  • 63 % Say there are community events

  • 57 % Say neighbors are friendly

  • 27 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • shatiea mcwhorter
    "Nice quiet neighborhood great neighbors everyone gets alone and we all help each other when needed great place to have a family "
    0
    Flag
  • Matthewckent
    "It’s quiet and nature friendly. I have lived here for over two years and it’s my favorite part of Orlando. "
    0
    Flag
  • Kauffmanlondon
    "Family area and quiet great schools low crime and there own police department. Mostly newer builds and on the exspensive side "
    0
    Flag
  • Karenamiles
    "very close to gas stations restaurants and shopping. just off Florida Turnpike. nearby lake in subdivision. nice walking community "
    0
    Flag
  • Cassyperrin
    "There are quite a few dogs, so if you have an antisocial pet this might not be the best place for your furry friend!!"
    1
    Flag
  • Jayrwingfield
    "the people are unique and its s very quiet and slow. kids play outside and the people of the community are very welcoming"
    1
    Flag
  • Michael G.
    "Easy Access to most things in central fl"
    2
    Flag
  • Anne M.
    "I visit this area frequently. My family members live there as well. It's a great neighborhood where people know one another and look out for each other. Only 69 lots and it's a dead end street so no additional traffic in this gated community of all custom homes"
    3
    Flag

LGBTQ Local Legal Protections

Apartments for Rent

Skip to last item
Skip to first item

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

6 rentals with air conditioning in Oakland, FL

Explore by feature - Pool

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Oakland, FL

Homes for sale near 400 Macchi Ave

Skip to last item
Skip to first item

Off Market Homes Near 400 Macchi Ave

Skip to last item
Skip to first item