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$565,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 3 Beds
  • 2 Full Baths
  • 1,338 Sq. Ft.
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Experience the best of Historic Winter Garden living in this gorgeous, fully renovated, 3 bed, 2 bath home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange Trail. Recently renovated to a high standard. Upgrades include: New AC, new water heater, new kitchen cabinets, quartz countertops, kitchen sink and faucet, tiled splashback, all new stainless appliances, new washer/dryer, new luxury vinyl flooring throughout, upgraded bathrooms, repainted internal and external, new interior doors and hardware, all new trim throughout, all new lighting, new windows and extensive landscaping Live the coveted Winter Garden lifestyle with golf cart access to charming boutiques, restaurants, breweries, parks, the weekly farmers market, Lake Apopka, splash pad, and more. This exceptional home perfectly combines historic charm with luxurious modern living in one of Central Florida's most sought-after communities. Don't miss this rare opportunity!

Full Property Details for 227 W Bay St

General

  • Price: $565,000
  • Taxes: $5,193 (2025)
  • Status: Pending
  • Type: Single Family
  • Source: MidFloridaRegionalMLS
  • MLS ID: S5154601
  • Updated: 7/30/2026
  • Added to Site: 24 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 8
  • Interior Features: Primary Bedroom Main Floor, Solid Surface Counters, Ceiling Fan(s), Chair Rail
  • Fireplace: Yes
  • Fireplace(s): Wood Burning
  • Appliances: Microwave, Range, Refrigerator, Washer, Dishwasher, Disposal, Dryer
  • Furnishings: Unfurnished
  • Flooring: Luxury Vinyl

Rooms

Bathrooms

  • Total Bathrooms: 2
  • Full Bathrooms: 2

Bedrooms

  • Total Bedrooms: 3

Other Rooms

  • Laundry: Laundry Closet

Exterior

  • Exterior Features: Sidewalk

Parking

  • Carports: Yes
  • Carport: 2
  • Carport Spaces: 2
  • Covered Spaces: 2
  • Parking Features: Driveway

Location

  • Area: 34787 - Winter Garden/Oakland
  • County: Orange
  • Development Name: 34787 - Winter Garden/Oakland
  • Subdivision: COOPER & SEWELL ADD
  • Driving Directions: Highway 50 west to Dillard St North, to Plant Street West, to N Highland Ave North, W onto W Bay St
  • Direction Faces: North

Community

  • Community Name: 34787 - Winter Garden/Oakland
  • Community Features: Lake
  • Pet Restrictions: SEE COUNTY PET RULES

Heating & Cooling

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

Utilities

  • Sewer: Public Sewer
  • Water District: LAKE APOPKA
  • Water: Public
  • Utility Description: BB/HS Internet Available, Public, Sewer Connected, Cable TV Available, Water Connected, Electricity Connected, Natural Gas Available

Structural Information

  • Exterior Const.: Block
  • Roof: Built-Up
  • Windows: Blinds
  • Stories/Levels: One
  • Square Feet: 1,338
  • Sq. Ft. Source: Public Records
  • Year Built: 1956

Lot Features

  • Lot Size (Acres): 0.2
  • Lot Size (Sq. Ft.): 9,100
  • Lot Size: 9100
  • Street/Road Desc.: Asphalt

Water Features

  • Water Access: Yes
  • Water Access Desc: Lake
  • Water Front Name: LAKE APOPKA
  • Water Front Desc.: Lake

Financial Considerations

  • Tax Amount: $5,193
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Fee Simple
  • Special Conditions: None
  • Legal Description: COOPER & SEWELL ADDITION F/3 9 W 97 FT OFS 1/2 LOT 19 & W 97 FT OF LOT 20 BLK E
  • Flood Zone Info: X
  • APN: 142227172805192
  • Property ID: 142227172805192
  • Block/Lot/Section: E

Listed by Watson Realty Corp.

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Listing agent

— 227 W Bay St —

  • Watson Realty Corp.

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 227 W Bay St

School District:Orange County School District
NameGradesDistance
Dillard Street Elementary School
311 North Dillard Street, Winter Garden, FL 34787
PK-50.6 mi
Lakeview Middle School
1200 West Bay Street, Winter Garden, FL 34787
6-80.8 mi
West Orange High School
1625 Beulah Road, Winter Garden, FL 34787
9-122.2 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 227 W Bay St Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/29/2026
Listed
$565,000
61.43%
MLS
1/21/2026
Sold
$350,000
—
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 227 W Bay St

Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,193
5%
$368,952
6%
2024
$4,934
-11%
$349,127
-10%
2023
$5,522
91%
$386,992
118%
2021
$2,889
-13%
$177,625
-21%
2022
$3,312
15%
$225,116
185%
2021
$2,889
654%
$78,909
2%
2019
$383
—
$77,135
2%
2018
$382
1%
$75,697
2%
2017
$379
-1%
$74,140
2%
2016
$384
-4%
$72,615
1%
2015
$400
-2%
$72,110
1%
2014
$407
4%
$71,538
1%
2013
$393
—
$70,481
—
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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with our affiliated lender
NMLS#: 1598647

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Listed by Watson Realty Corp.

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227 W Bay Street, Winter Garden, FL 34787 (MLS# S5154601) is a Single Family property with 3 bedrooms and 2 full bathrooms. 227 W Bay Street is currently listed for $565,000 and was received on July 29, 2026. Want to learn more about 227 W Bay Street? Do you have questions about finding other Single Family real estate for sale in Winter Garden? You can browse all Winter Garden real estate or contact a Coldwell Banker agent to request more information.

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