$1,450,000

217 Bay Street

Winter Garden, FL 34787

Active
5
Beds
4
Baths
2,800
Sq Ft
0.17
Acres
2025
Built
Water accessFireplace$518/sqft360° tour

About this home

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!

Estimated monthly payment

$8,493/mo

Principal & interest$7,332
Property taxes$497
Home insurance (est.)$665

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history20 days on market

  1. Status: Active
    May 9, 2026
  2. Listed$1,495,000
    May 9, 2026
  3. Price reduced$1,450,000

Virtual Tour

Facts & features

Property type
Residential
Sub type
Single Family Residence
Status
Active
Days on market
20
Subdivision
Cooper & Sewell Add
County
Orange
Year built
2025
Living area
2,800 sq ft
Price/sq ft
$518
Building area
3,536 sq ft (Owner)
Lot size
7,741 sq ft
Lot category
0 to less than 1/4
Flood zone
X
Annual taxes
$5,958 (2025)
Parcel #
14-22-27-1728-05-191
Zoning
R-2
MLS #
S5149527

Interior Details

Bedrooms
5
Full bathrooms
4
Flooring
Luxury Vinyl
Appliances
Microwave, Built-In Oven, Refrigerator, Washer, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Wine Refrigerator
Interior features
Eat-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 Fans(s), Chair Rail
Laundry
Laundry Room
Stories / Levels
Two
Direction faces
East
Fireplace
Yes

Heating & Cooling

Heating
Central, Electric
Cooling
Central Air

Parking

Parking features
Covered, Driveway, Electric Vehicle Charging Station(s)
Carport
Yes

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Homestead exemption
Yes
Min lease term
8-12 Months
Listing terms
Cash, Conventional
Ownership
Fee Simple
Available for lease
Yes
Lease restrictions
Yes
Additional lease restrictions
See county requirements

Exterior & Construction

Exterior features
French Doors, Garden, Lighting, Outdoor Grill, Outdoor Kitchen, Private Yard, Rain Gutters, Storage
Construction materials
Block, Stucco, Vinyl Siding
Roof
Shingle
Foundation
Slab
Water access
Yes
Road surface
Asphalt

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Public, Sewer Connected, Water Connected, Cable Connected, Electricity Connected

Community

Pets allowed
Yes

Room Details

RoomLevelDimensions
WorkshopFirst10x9
Utility RoomFirst8x8
Bedroom 5First11x9
Bedroom 4First16x11
Bedroom 3Second13x10
Bedroom 2Second15x13
Primary BedroomFirst15x14
KitchenFirst18x12
Dining RoomFirst19x15
Living RoomFirst19x15

Listing Details

Listing date
2026-05-09
On market date
2026-05-09
Original list price
$1,495,000
Occupant type
Owner
MLS area
34787 - Winter Garden/Oakland
Listing AOR
Osceola
Status changed
2026-05-09
Tax 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

Location

Flood zone
X

Directions

Highway 50 west to Dillard St North, to Plant Street West, to N Highland Ave North, W onto W Bay St

More homes like this

MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of May 29, 2026 at 10:06 AM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA