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$1,499,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 2,188 Sq. Ft.
  • Updated 1 day ago
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Welcome to 20 Oakdale Street, an exceptional waterfront luxury residence in the highly sought-after Town of Windermere with direct access to Lake Down and the Butler Chain of Lakes offering an ideal blend of elegance, privacy, and Florida lifestyle, this beautiful home is perfectly positioned to enjoy the area's charming small-town atmosphere while remaining just minutes from world-class dining, shopping, golf, and attractions * Incredible backyard * Summer Kitchen with Pizza Oven * Firepit with Stone Seating * Boathouse * Viking 6 Burner Gas Cooktop * Viking Fridge * Built in 2004 * 2 Suites on 1st Floor * Step inside to discover spacious living areas filled with natural light, soaring ceilings, and thoughtfully designed spaces perfect for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into inviting gathering spaces, while the generous bedrooms provide comfort and privacy for family and guests. * Outside, enjoy your own private retreat with beautifully landscaped grounds, ample outdoor living space, and the opportunity to experience everything that makes Windermere one of Central Florida's most desirable communities. Whether relaxing by the pool, hosting friends, or taking advantage of nearby lakes and recreation, this home offers the lifestyle you've been searching for. * Located within close proximity to top-rated schools, renowned golf courses, the Butler Chain of Lakes, and just a short drive to downtown Orlando and major theme parks, this is a rare opportunity to own a premier property in one of Florida's most prestigious addresses.

Full Property Details for 20 Oakdale St

General

  • Price: $1,499,000
  • Taxes: $21,535 (2025)
  • Status: Active
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: O6421265
  • Updated: 7/1/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: No Minimum

Interior

  • Number of Rooms: 6
  • Interior Features: Eating Space In Kitchen, Kitchen and Family Room Combination, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Solid Wood Cabinets, Split Bedroom, Walk-In Closet(s)
  • Fireplace: Yes
  • Fireplace(s): Outside
  • Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Electric Water Heater, Microwave, Refrigerator
  • Furnishings: Unfurnished
  • Flooring: Travertine, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Inside, Laundry Room

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Gunite, In Ground, Tile
  • Spa: Yes
  • Spa Description: Heated, In Ground

Exterior

  • Exterior Features: Fire Pit, French Doors, Irrigation System, Outdoor Grill, Permeable Paving
  • Deck/Patio: Covered, Front Porch, Rear Porch
  • Porch/Patio/Deck: Covered, Front Porch, Rear Porch

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Garage Door Opener

Location

  • Area: 34786 - Windermere
  • County: Orange
  • Development Name: 34786 - Windermere
  • Subdivision: DAVIS SHORES
  • Driving Directions: Main St to 1st Avenue - Go West to Oakdale & turn left to the house
  • Direction Faces: East

School Information

  • Elementary School: Windermere Elem
  • Middle School: Gotha Middle
  • High School: Olympia High

Community

  • Community Name: 34786 - Windermere

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Septic Tank
  • Water District: LAKE DOWN - BUTLER CHAIN
  • Water: Canal/Lake For Irrigation
  • Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected

Structural Information

  • Architectural Info: Craftsman
  • Architectural Style: Craftsman
  • Exterior Const.: Block, HardiPlank Type, Stone, Stucco
  • Roof: Metal
  • Windows: Insulated Windows
  • Stories/Levels: Two
  • Square Feet: 2,188
  • Sq. Ft. Source: Public Records
  • Year Built: 2004

Additional Structures

  • Other Structures: Boat House, Outdoor Kitchen

Lot Features

  • Property View: Water
  • Lot Size (Acres): 0.42
  • Lot Size (Sq. Ft.): 18,500
  • Lot Size: 18500
  • Lot Dimensions: 185 x 100
  • Frontage: Street Paved
  • Street/Road Desc.: Paved, Asphalt
  • Fencing (Description): Fenced

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Access: Yes
  • Water Access Desc: Canal - Freshwater, Lake - Chain of Lakes
  • Water Extras: Yes
  • Water Front Name: LAKE DOWN - BUTLER CHAIN
  • Water Front Desc.: Freshwater Canal

Financial Considerations

  • Tax Amount: $21,535.36
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: DAVIS SHORES S/123 LOT 13 BLK A
  • Flood Zone Info: X
  • APN: 82328194801130
  • Property ID: 82328194801130
  • Block/Lot/Section: A

Listed by Vintage Realty Group Llc

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Listing agent

— 20 Oakdale St —

  • Vintage Realty Group Llc

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 20 Oakdale St

School District:Orange County School District
NameGradesDistance
Windermere Elementary School
11125 Park Avenue, Windermere, FL 34786
K-50.6 mi
Gotha Middle School
9155 Gotha Road, Windermere, FL 34786
6-82.1 mi
Olympia High School
4301 South Apopka Vineland Road, Orlando, FL 32835
9-121.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 20 Oakdale St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/01/2026
Listed
$1,499,000
36.27%
MLS
11/03/2021
Sold
$1,100,000
—
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 20 Oakdale St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$21,535
—
$1,261,700
-1%
2025
$21,535
6%
$1,275,020
3%
2024
$20,358
8%
$1,238,700
5%
2023
$18,880
68%
$1,184,151
85%
2021
$11,247
-31%
$639,899
-34%
2022
$16,307
45%
$976,267
58%
2021
$11,247
10%
$618,440
2%
2019
$10,240
1%
$604,536
2%
2018
$10,141
6%
$593,264
4%
2017
$9,534
—
$568,359
1%
2016
$9,570
52%
$560,865
55%
2015
$6,278
3%
$361,825
1%
2014
$6,114
2%
$358,953
2%
2013
$5,986
—
$353,648
—
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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Listed by Vintage Realty Group Llc

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20 Oakdale Street, Windermere, FL 34786 (MLS# O6421265) is a Single Family property with 3 bedrooms and 2 full bathrooms. 20 Oakdale Street is currently listed for $1,499,000 and was received on July 01, 2026. Want to learn more about 20 Oakdale Street? Do you have questions about finding other Single Family real estate for sale in Windermere? You can browse all Windermere real estate or contact a Coldwell Banker agent to request more information.

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