415 Macchi Ave, Oakland, FL 34787
OFF MARKET

415 Macchi Ave
Oakland, FL 34787

  • 4 Beds
  • 3.5 Baths
  • 3,423 sqft (on 0.34 acres)

$890,000

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $6,048/mo*
Refinance Your Home

$890,000

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $6,048/mo*
Refinance Your Home
4 Beds
3.5 Baths
3,423 sqft
(on 0.34 acres)

Local Information

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

Description

Move in Ready and a Fresh Look... New exterior paint, interior wall, trim and door paint, new front, back and side yard tropical landscape and sod. Nestled amongst the majestic oaks of Downtown Oakland and Winter Garden & steps from the WEST ORANGE TRAIL, this home sits in one of the most popular areas of Central Florida. Just minutes away from highly sought after HISTORIC DOWNTOWN WINTER GARDEN, this David Weekly Custom Built Home, perfect for recreation & relaxation, is waiting for you. After your morning walk on the trail (right across the street) enjoy COMPLETE PRIVACY on your FULLY FENCED Corner Lot & take a dip in your private POOL & SPA. Inside, you will find 4 Bedrooms, 4 Bathrooms + BONUS ROOM!! SOARING ceilings provide unbelievable natural light in this updated and upgraded home, including: ~ NEW ROOF (2019) ~ SOLAR PANELS (2015) .. hello energy savings!! ~ a WHOLE HOUSE GENERATOR (2016) and a TRUE GOURMET CHEF's KITCHEN w/ Restaurant Style Refrigerator, gorgeous exotic granite, Convection Wall Oven, separate Cook Top w/ SS vent system & entertaining/prep island, large pantry & tons of cabinet space. The floor to ceiling STACKED STONE FIREPLACE w/ Custom Built-ins will make the Family Room your favorite room in the house. The DOWNSTAIRS MASTER SUITE offers a huge bedroom w/ Crown Molding & Plantation Shutters over looking the pool & backyard. Dual sinks, Large Walk -in Shower, corner soaker tub & CUSTOM BUILT-INs in the MASTER CLOSET make it the perfect retreat. The ext. driveway, OVERSIZED GARAGE & Lush Tropical Landscaping make it complete. Also enjoy preferred enrollment & walking distance to 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. This description is from July 11, 2023

Home Highlights

Parking
2 Car Garage
Outdoor
Porch, Patio, Pool
View
Trees/Woods
HOA
$58/Monthly
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 415 Macchi Ave

Interior Features

Interior Details
Number of Rooms: 11Types of Rooms: Master Bedroom, Bedroom 2, Bedroom 3, Bedroom 4, Balcony Porch Lanai, Bonus Room, Dining Room, Family Room, Kitchen, Laundry, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 3Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 3423 Square Feet
Appliances & Utilities
Utilities: BB/HS Internet Available, Cable Connected, Electricity Connected, Propane, SolarAppliances: Oven, Convection Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Range Hood, RefrigeratorDishwasherDisposalLaundry: Laundry RoomMicrowaveRefrigerator
Heating & Cooling
Heating: Central,ElectricHas CoolingAir Conditioning: Central Air,ZonedHas HeatingHeating Fuel: Central
Fireplace & Spa
Fireplace: Electric, Family RoomSpa: Heated, In GroundHas a FireplaceHas a Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: Blinds, ShuttersFlooring: Carpet, Ceramic Tile, Hardwood
Levels, Entrance, & Accessibility
Stories: 2Levels: TwoFloors: Carpet, Ceramic Tile, Hardwood
View
Has a ViewView: Trees/Woods
Security
Security: Security System Owned, Smoke Detector(s)

Exterior Features

Exterior Home Features
Roof: ShinglePatio / Porch: Covered, Front Porch, Patio, ScreenedFencing: FencedVegetation: Mature Landscaping, Oak Trees, Trees/LandscapedExterior: Irrigation System, Rain GuttersFoundation: SlabHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2Other Parking: Garage Dimensions: 23x22No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage Door Opener,Garage Faces Side,Oversized
Pool
Pool: Auto Cleaner, Gunite, Heated, In Ground, Salt Water, Screen EnclosurePool
Frontage
Road Surface Type: Paved, AsphaltNot on Waterfront
Water & Sewer
Sewer: Septic Tank

Days on Market

Cumulative Days on Market: 4

Property Information

Year Built
Year Built: 2006
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Traditional
Building
Construction Materials: Block, Stucco, Wood FrameNot a New ConstructionNo Additional Parcels
Property Information
Parcel Number: 212227940200450

Price & Status

Price
List Price: $799,900
Status Change & Dates
Off Market Date: Mon Jun 12 2023Possession Timing: Close Of Escrow

Active Status

MLS Status: Sold

Media

Location

Direction & Address
City: WINTER GARDENCommunity: WINTERS LANDING
School Information
Elementary School: Lakeville ElemJr High / Middle School: Lakeview MiddleHigh School: West Orange High

Building

Building Area
Building Area: 4533 Square Feet

Community

Community Features: Golf Carts OK, Irrigation-Reclaimed Water, Park, Playground, SidewalksNot Senior Community
Other
Playground

HOA

HOA Name: Southwest Property ManagementAssociation for this Listing: Orlando RegionalHas an HOAHOA Fee: $58/Monthly

Lot Information

Lot Area: 0.34 acres

Listing Info

Special Conditions: None

Offer

Listing Terms: Cash, Conventional, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

Mls Number: O6117313Showing Requirements: Call Listing Agent, ShowingTimeUniversal Property Id: US-12095-N-212227940200450-R-N

Additional Information

HOA Amenities: Park,Playground
Last check for updates: about 8 hours ago
Listed by Jeremy Sainlar, (407) 403-1977
JEEVES REALTY LLC, (407) 375-4566
Bought with: Robert Schott, (407) 347-3800, TEAMCONNECT REALTY LLC, (407) 347-3800
Originating MLS: Orlando Regional
Source: Stellar MLS, MLS#O6117313
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. Some IDX listings have been excluded from this website.
Listing Information presented by local MLS brokerage: Zillow, Inc - (407) 904-3511

Price History for 415 Macchi Ave

DatePriceEventSource
07/11/2023$750,000Sold
Stellar MLS #O6117313
06/12/2023$799,900PendingStellar MLS #O6117313
06/09/2023$799,900Listed For SaleStellar MLS #O6117313
11/19/2019$523,000Sold
N/A
09/27/2019$523,000PendingAgent Provided
09/24/2019$523,000Listed For SaleAgent Provided
12/02/2014$410,000Sold
N/A
01/04/2007$470,000Sold
N/A
03/02/2006$368,100Sold
N/A
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Property Tax and Assessment

Year2024
Tax$7,924
Assessment$643,566
Home facts updated by county records

Comparable Sales for 415 Macchi Ave

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
413 Macchi Ave, Oakland, FL
0.02
Single-Family Home
$840,000
08/29/25
4
3
3,290
501 E Oakland Ave, Oakland, FL
0.22
Single-Family Home
$850,000
04/06/26
4
3.5
3,448
8 Winters Landing Dr, Oakland, FL
0.20
Single-Family Home
$850,000
05/27/26
4
3
2,850
1126 Riverway Dr, Oakland, FL
0.03
Single-Family Home
$1,000,000
07/15/25
4
3
2,711
1180 Riverway Dr, Oakland, FL
0.10
Single-Family Home
$990,900
07/09/25
4
3.5
2,796
1096 Riverway Dr, Winter Garden, FL
0.08
Single-Family Home
$1,575,000
01/23/26
4
3.5
4,171
410 E Gulley Ave, Oakland, FL
0.11
Single-Family Home
$604,000
09/19/25
5
3
2,458
100 Demens St, Oakland, FL
0.24
Single-Family Home
$950,000
09/23/25
4
3
3,025
1185 Wilder Oaks Way, Oakland, FL
0.11
Single-Family Home
$999,000
02/17/26
4
3.5
2,789
70 Millholland St, Oakland, FL
0.32
Single-Family Home
$865,000
07/25/25
5
3
2,534

Nearby homes

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Assigned Schools

These are the assigned schools for 415 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

  • 61 % 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.
  • Trulia User
    "Its great to live this area we have market and restauran near us . We can walk when we want in our neighboorhood. We have parks schools near us …"
    0
    Flag
  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • 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
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  • John D. H.
    "average, plenty of bus access, no major traffic issues. normal boring vanilla winter garden. lahdeedah"
    0
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  • 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
  • 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
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  • 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
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  • Ryanm1995
    "They will love this neighborhood. Bright open space to walk around. We also have a lot of friendly dog in our neighborhood. "
    0
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415 Macchi Ave, Oakland, FL 34787 is a 4 bedroom, 4 bathroom, 3,423 sqft single-family home built in 2006. This property is not currently available for sale. 415 Macchi Ave was last sold on Jul 11, 2023 for $750,000 (6% lower than the asking price of $799,900). The current Trulia Estimate for 415 Macchi Ave is $890,000.