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Property Description
LOCATION, LOCATION, LOCATION! Experience the best of Historic Winter Garden living in this brand-new Craftsman-style home, ideally located just steps from downtown dining, shopping, entertainment, and the renowned West Orange Trail. Originally a charming 1950s bungalow, the 576 sq. ft. home has been completely renovated and thoughtfully expanded into a stunning 2,800 sq. ft. residence offering 5 bedrooms, 4 bathrooms, and exceptional modern upgrades throughout. Relax on the inviting front porch and enjoy the charm and atmosphere of this idyllic golf cart community. Inside, a bright and spacious open floor plan welcomes you with designer finishes, 10-foot ceilings, luxury waterproof vinyl plank flooring, plantation shutters, 8-foot doors, and elegant architectural details throughout. The heart of the home is the spectacular chef's kitchen featuring premium LG stainless steel appliances, built-in oven and microwave, induction cooktop, wine fridge, oversized island with seating and storage, 42" refrigerator, and an enormous walk-in pantry complete with an additional retro-style refrigerator. The adjoining family room showcases a custom fireplace with built-in storage and two sets of French doors opening to a large covered lanai with summer kitchen, overlooking the beautifully landscaped and fully fenced backyard with additional deck space for entertaining and relaxing. The luxurious primary suite offers custom walk-in closets, a spa-inspired en-suite bath, and private French doors leading to a secluded patio and deck area. A separate lower-level wing includes two additional bedrooms, a full bath, and utility room, creating endless possibilities for an in-law suite, home office, theater room, or private guest retreat. Upstairs, you'll find two spacious bedrooms, including one with en-suite bath, an additional full bath, linen storage, and generous extra storage space. Additional highlights include a covered carport with EV charging outlet, oversized driveway with parking for at least 6 cars, 2-zone A/C system, gutters with leaf guards, upgraded lighting, charming picket fencing, lush landscaping, and a 10x8 storage/workshop. 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
Full Property Details for 217 W Bay St
General
- Price: $1,495,000
- Taxes: $5,958 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: S5149527
- Updated: 5/9/2026
- Added to Site: 6 day(s) ago
Rental Information
- Min. Lease: 8-12 Months
Interior
- Number of Rooms: 10
- Interior Features: Eating Space In Kitchen, High Ceilings, Open Floorplan, Primary Bedroom Main Floor, Solid Surface Counters, Split Bedroom, Walk-In Closet(s), Window Treatments, Built-in Features, Ceiling Fan(s), Chair Rail
- Fireplace: Yes
- Fireplace(s): Electric
- Appliances: Microwave, Built-In Oven, Refrigerator, Washer, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Wine Refrigerator
- Furnishings: Unfurnished
- Flooring: Luxury Vinyl
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 4
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Laundry Room
Exterior
- Exterior Features: French Doors, Garden, Irrigation System, Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard, Rain Gutters, Storage
Parking
- Carports: Yes
- Carport: 1
- Carport Spaces: 1
- Covered Spaces: 1
- Parking Features: Covered, Driveway, Electric Vehicle Charging Station(s)
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: East
Community
- Community Name: 34787 - Winter Garden/Oakland
- Community Features: Community Boat Ramp, Fishing, Public Boat Ramp, Golf Carts OK
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, Water Connected, Cable Connected, Electricity Connected
Structural Information
- Exterior Const.: Block, Stucco, Vinyl Siding
- Roof: Shingle
- Windows: Shutters, Double Pane Windows
- Stories/Levels: Two
- Square Feet: 2,800
- Sq. Ft. Source: Builder
- Year Built: 2025
Lot Features
- Lot Size (Acres): 0.17
- Lot Size (Sq. Ft.): 7,741
- Lot Size: 7741
- Street/Road Desc.: Asphalt
- Fencing (Description): Vinyl, Wood
Water Features
- Water Access: Yes
- Water Access Desc: Lake
- Water Extras: Yes
- Water Front Name: LAKE APOPKA
Financial Considerations
- Tax Amount: $5,958
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: COOPER & SEWELL ADDITION F/39 E1/2 OF S1/2 LOT 19 & E1/2 OF LOT 20 (LESS W 10 FT THEREOF) & W1/2 OF VAC ALLEY ON E BLK E
- Flood Zone Info: X
- APN: 142227172805191
- Property ID: 142227172805191
- Block/Lot/Section: E
Listed by Watson Realty Corp.
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Schools
Schools serving 217 W Bay St
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Dillard Street Elementary School 311 North Dillard Street, Winter Garden, FL 34787 | PK-5 | 0.6 mi |
Lakeview Middle School 1200 West Bay Street, Winter Garden, FL 34787 | 6-8 | 0.9 mi |
West Orange High School 1625 Beulah Road, Winter Garden, FL 34787 | 9-12 | 2.2 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 217 W Bay St
Date
Details
Price
Change
Source
5/09/2026
Listed
$1,495,000
346.27%
MLS
2/09/2023
Sold
$335,000
—
Public Record
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
Tax History for 217 W Bay St
Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,555
—
$465,970
61%
2025
$4,555
15%
$289,560
17%
2024
$3,960
959%
$248,208
411%
2023
$374
11%
$48,531
6%
2021
$337
-5%
$45,745
-3%
2022
$353
5%
$47,117
4%
2021
$337
6%
$45,113
2%
2019
$318
3%
$44,099
2%
2018
$308
5%
$43,277
2%
2017
$292
3%
$42,387
2%
2016
$283
-1%
$41,515
1%
2015
$285
—
$41,226
1%
2014
$284
5%
$40,899
1%
2013
$271
—
$40,295
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 217 W Bay St
217 W Bay Street, Winter Garden, FL 34787 (MLS# S5149527) is a Single Family property with 5 bedrooms and 4 full bathrooms. 217 W Bay Street is currently listed for $1,495,000 and was received on May 09, 2026. Want to learn more about 217 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.

