508 Macchi Ave, Oakland, FL 34787
OFF MARKET

508 Macchi Ave
Oakland, FL 34787

  • 3 Beds
  • 3 Baths
  • 2,425 sqft (on 0.33 acres)

$681,800

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $4,658/mo*
Refinance Your Home

$681,800

Trulia Estimate
as of Jun 18, 2026
Est. Refi. Payment $4,658/mo*
Refinance Your Home
3 Beds
3 Baths
2,425 sqft
(on 0.33 acres)

Local Information

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

Description

Amazing Winters Landing Home. Ready for Summer fun and relaxation? Then check out this meticulously maintained David Weekley home! Private back yard with no rear neighbors, backs to West Orange Trail with privacy hedge. Very gently lived in. Located in sought after quaint town of Oakland Florida. Features 3 bedrooms, 3 baths, 3 car side entry garage and an additional "Flex/Bonus" space which is perfect for media area, office, library, etc. The choice is yours. Very large kitchen is designed for family gatherings, Sunday suppers, entertaining and holiday dinners. Offers center island and 42 inch cabinets. Other amazing features include crown molding throughout, plantation shutters, wood flooring and the list goes on. Perfect floor plan includes large master with dual walk in closets, master bath with garden tub and separate shower. Formal living and dining room. Great location and easy stroll or bike ride on the West Orange Trail leads you to beautiful downtown Winter Garden with restaurants, shops, weekend farmers market, tons of family activities and more. This home also provides preferred enrollment at Oakland 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
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HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 508 Macchi Ave

Interior Features

Heating & Cooling
Heating: Forced Air, ElectricAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 1Floors: Tile, Carpet, Hardwood
Interior Details
Types of Rooms: Walk In ClosetCeiling Fan
Appliances & Utilities
Cable ReadyMicrowaveRefrigerator

Exterior Features

Exterior Home Features
Roof: Composition
Parking & Garage
GarageParking: Carport, Garage Attached

Property Information

Year Built
Year Built: 2006Year Updated: 2006
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 0.33 acres

Price History for 508 Macchi Ave

DatePriceEventSource
08/25/2016$325,000Sold
Stellar MLS #O5457358
08/15/2016$329,900PendingAgent Provided
08/04/2016$329,900PendingToActiveAgent Provided
08/04/2016$329,900PendingAgent Provided
08/03/2016$329,900Listed For SaleAgent Provided
07/12/2006$410,000Sold
N/A
04/10/2006$296,600Sold
N/A

Market trends in Oakland

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
28
1MoM
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Property Tax and Assessment

Year2024
Tax$3,806
Assessment$526,177
Home facts updated by county records

Homeowner tools

Estimated monthly rent$3,274/mo
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Homes for rent near 508 Macchi Ave

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Comparable Sales for 508 Macchi Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
8 Winters Landing Dr, Oakland, FL
0.13
Single-Family Home
$850,000
05/27/26
4
3
2,850
410 E Gulley Ave, Oakland, FL
0.14
Single-Family Home
$604,000
09/19/25
5
3
2,458
413 Macchi Ave, Oakland, FL
0.12
Single-Family Home
$840,000
08/29/25
4
3
3,290
1126 Riverway Dr, Oakland, FL
0.10
Single-Family Home
$1,000,000
07/15/25
4
3
2,711
310 E Gulley Ave, Oakland, FL
0.23
Single-Family Home
$683,000
04/17/26
3
2
1,763
501 E Oakland Ave, Oakland, FL
0.20
Single-Family Home
$850,000
04/06/26
4
3.5
3,448
936 Allendale Ln, Winter Garden, FL
0.20
Single-Family Home
$1,025,000
07/21/25
4
3
2,711
1180 Riverway Dr, Oakland, FL
0.20
Single-Family Home
$990,900
07/09/25
4
3.5
2,796
70 Millholland St, Oakland, FL
0.42
Single-Family Home
$865,000
07/25/25
5
3
2,534
1096 Riverway Dr, Winter Garden, FL
0.06
Single-Family Home
$1,575,000
01/23/26
4
3.5
4,171

Nearby homes

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Assigned Schools

These are the assigned schools for 508 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 11 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

  • 89 % Say it's quiet

  • 85 % Say kids play outside

  • 83 % Say there's wildlife

  • 79 % Say parking is easy

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

  • 64 % Say streets are well-lit

  • 63 % Say people would walk alone at night

  • 60 % 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
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  • Matthewckent
    "It’s quiet and nature friendly. I have lived here for over two years and it’s my favorite part of Orlando. "
    0
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  • Kauffmanlondon
    "Family area and quiet great schools low crime and there own police department. Mostly newer builds and on the exspensive side "
    0
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  • 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
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  • 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
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Apartments for Rent

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Homes for sale near 508 Macchi Ave

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Off Market Homes Near 508 Macchi Ave

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508 Macchi Ave, Oakland, FL 34787 is a 3 bedroom, 3 bathroom, 2,425 sqft single-family home built in 2006. This property is not currently available for sale. 508 Macchi Ave was last sold on Aug 25, 2016 for $325,000. The current Trulia Estimate for 508 Macchi Ave is $681,800.