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$875,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,448 Sq. Ft.
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One or more photo(s) has been virtually staged. Welcome to your private retreat in the heart of Oakland! This stunning 4-bedroom, 3.5-bathroom home offers 3,448 sq. ft. of beautifully designed living space on an oversized 0.34-acre lot with no rear neighbors, providing peace and privacy in a serene setting. Enjoy the best of both worlds with a quiet neighborhood just steps from Oakland Avenue Charter School and minutes from Historic Downtown Winter Garden, where you can explore boutique shops, award-winning restaurants, and the scenic West Orange Trail. Inside, the thoughtfully designed layout features primary suites on both the first and second floors, offering flexible living arrangements perfect for multigenerational families or guests. The open floor plan and spacious living areas create a comfortable flow throughout, ideal for everyday living and entertaining alike. Step outside to your own backyard oasis, complete with a sparkling pool and spa surrounded by lush landscaping-perfect for relaxing weekends or hosting gatherings. Additional highlights include a brand-new roof installed in September 2025, offering long-term peace of mind and value. With its ideal location, privacy, and resort-style outdoor living, this home perfectly captures the essence of Florida living!

Full Property Details for 501 E Oakland Ave

General

  • Price: $875,000
  • HOA FEE: $73/month
  • HOA FEE FREQ.: Quarterly
  • Taxes: $6,337 (2024)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6355030
  • Updated: 12/30/2025
  • Added to Site: 87 day(s) ago

Interior

  • Number of Rooms: 12
  • Interior Features: Ceiling Fan(s), Crown Molding, High Ceilings, Primary Bedroom Main Floor, PrimaryBedroom Upstairs, Split Bedroom
  • Fireplace: Yes
  • Fireplace(s): Living Room
  • Appliances: Built-In Oven, Cooktop, Refrigerator
  • Flooring: Ceramic Tile, Engineered Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Laundry Room

Additional Information

  • Shared Amenities: Playground
  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, Heated, In Ground, Screen Enclosure
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Other
  • Deck/Patio: Front Porch
  • Porch/Patio/Deck: Front Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Covered Spaces: 3

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: WINTERS LNDG PH 01 A D F & G
  • Driving Directions: From West Colonial Drive (HWY SO), head north on Tubb Street. Turn right onto E Oakland Avenue. Home will be on the right.
  • Direction Faces: South

School Information

  • Elementary School: Tildenville Elem
  • Middle School: Lakeview Middle
  • High School: West Orange High

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Golf Carts OK, Playground, Sidewalks
  • Optional Amenities: Playground
  • Association: Yes
  • Assoc. Name: Southwest Property Management Of Central Florida
  • Pet Restrictions: Please verify with HOA

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central

Utilities

  • Sewer: Septic Tank
  • Water: Public
  • Utility Description: Other

Structural Information

  • Exterior Const.: Block, Concrete, Stucco
  • Roof: Shingle
  • Stories/Levels: Two
  • Square Feet: 3,448
  • Sq. Ft. Source: Public Records
  • Year Built: 2007

Lot Features

  • Lot Size (Acres): 0.34
  • Lot Size (Sq. Ft.): 14,831
  • Lot Size: 14831
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Association Fee: $220
  • Assoc Fee Freq.: Quarterly
  • Assoc Fee Desc.: Required
  • Tax Amount: $6,337
  • Tax Year: 2024

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: WINTERS LANDING PHASE 1 60/17 LOT 4
  • Flood Zone Info: X
  • APN: 212227940100040
  • Property ID: 212227940100040

Listed by Homevest Realty

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Listing agents

— 501 E Oakland Ave —

  • Homevest Realty

  • Homevest Realty

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 501 E Oakland Ave

School District:Orange County School District
NameGradesDistance
Tildenville Elementary School
1221 Brick Road, Winter Garden, FL 34787
PK-50.9 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-81.3 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-123.4 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 501 E Oakland Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/30/2025
Price Reduced
$875,000
-2.67%
MLS
11/21/2025
Price Reduced
$899,000
-5.37%
MLS
10/23/2025
Listed
$950,000
18.76%
MLS
5/10/2024
Sold
$799,900
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 501 E Oakland Ave

Year
Property Taxes
Change
Tax Assessment
Change
2024
$6,337
—
$701,672
80%
2024
$6,337
6%
$390,194
3%
2023
$5,984
4%
$378,829
6%
2021
$5,747
-1%
$357,083
-3%
2022
$5,808
1%
$367,795
4%
2021
$5,747
1%
$352,153
2%
2019
$5,668
—
$344,236
2%
2018
$5,655
10%
$337,817
10%
2017
$5,154
—
$307,362
2%
2016
$5,130
-1%
$301,040
1%
2015
$5,204
17%
$298,947
16%
2014
$4,454
2%
$258,445
1%
2013
$4,353
—
$254,626
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by Homevest Realty

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501 E Oakland Avenue, Oakland, FL 34787 (MLS# O6355030) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 501 E Oakland Avenue is currently listed for $875,000 and was received on October 23, 2025. Want to learn more about 501 E Oakland Avenue? Do you have questions about finding other Single Family real estate for sale in Oakland? You can browse all Oakland real estate or contact a Coldwell Banker agent to request more information.

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