To schedule a showing of 217 W Bay Street, Winter Garden, Florida, Call David Shippey at 863-521-4517 TODAY!

$1,395,000 Reduced -$55,000
217 W Bay Street
Winter Garden, FL 34787
  • 5Beds
  • 4.00Total Baths
  • 4 Full, 0 HalfBaths
  • 2,800SqFt
  • 2025Year Built
  • 0.17Acres
  • MLS# S5149527
  • Residential
  • SingleFamilyResidence
  • Active

  • Approx Time on Market1 month, 10 days
  • Area34787 - Winter Garden/oakland
  • CountyOrange
  • Subdivision Cooper & Sewell Add

Overview

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 chefs 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, youll 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 Floridas most sought-after communities. Dont miss this rare opportunity!



Agriculture / Farm

Association Fees / Info

Community Features:  BoatFacilities, Fishing, GolfCartsOk

Pets Allowed:  Yes

Bathroom Info

Total Baths:  4.00

Fullbaths:  4

Building Info

Window Features:  DoublePaneWindows, Shutters, WindowTreatments

Roof:  Shingle

Building Area Source:  Owner

Buyer Compensation

Exterior Features

Exterior Features:  FrenchPatioDoors, Garden, SprinklerIrrigation, Lighting, OutdoorGrill, OutdoorKitchen, PrivateYard, RainGutters, Storage

Fees / Restrictions

Financial

Original Price:  $1,495,000

Fencing:  Vinyl, Wood

Garage / Parking

Parking Features:  Covered, Driveway, ElectricVehicleChargingStations

Carport:  Yes

Car Ports:  1

Green / Env Info

Interior Features

Fireplace Desc:  Electric

Fireplace:  Yes

Floors:  LuxuryVinyl

Levels:  Two

Laundry Features:  LaundryRoom

Interior Features:  BuiltInFeatures, ChairRail, CeilingFans, EatInKitchen, HighCeilings, MainLevelPrimary, OpenFloorplan, SplitBedrooms, SolidSurfaceCounters, WalkInClosets, WindowTreatments

Appliances:  BuiltInOven, Cooktop, Dryer, Dishwasher, ExhaustFan, ElectricWaterHeater, Disposal, Microwave, Refrigerator, WineRefrigerator, Washer

Lot Info

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

Lot Size Units:  Acres

Lot Size Acres:  0.17

Lot Sqft:  7,741

Misc

Other

Special Conditions:  None

Other Rooms Info

Property Info

Section:  14

Class Type:  SingleFamilyResidence

Property Sub Type:  SingleFamilyResidence

Construction Materials:  Block, Stucco, VinylSiding

Stories:  2

Foundation:  Slab

Human Modified:  Yes

Room Info

Total Rooms:  10

Sqft Info

Sqft:  2,800

Bulding Area Sqft:  3,536

Living Area Units:  SquareFeet

Living Area Source:  Builder

Tax Info

Tax Year:  2,025

Tax Lot:  19

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

Tax Block:  E

Tax Annual Amount:  5958

Tax Book Number:  F-39

Unit Info

Utilities / Hvac

Heating:  Central, Electric

Water Source:  Public

Sewer:  PublicSewer

Cool System:  CentralAir, CeilingFans

Cooling:  Yes

Heating:  Yes

Utilities:  CableConnected, ElectricityConnected, HighSpeedInternetAvailable, MunicipalUtilities, SewerConnected, WaterConnected

Waterfront / Water

Waterfront Features:  LakePrivileges

Water Body Name:  LAKE APOPKA

Directions

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

This listing courtesy of Watson Realty Corp. 

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Price & Status History (on davidshippey.com since Sat, May 9th 2026)
  • Original Price: $1,495,000
  • Current Price: $1,395,000
  • Price Reduced: $100,000
Date ChangedFromTo
06/15/2026$1,450,000 $1,395,000 Reduced by $55,000
05/29/2026$1,495,000 $1,450,000 Reduced by $45,000

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If you have any questions on 217 W Bay Street, Winter Garden, Florida, please call David Shippey at 863-521-4517.


MLS# S5149527 located at 217 W Bay Street, Winter Garden, Florida is brought to you by David Shippey REALTOR®

217 W Bay Street, Winter Garden, Florida has 5 Beds, 4 Full Bath, and 0 Half Bath.
The MLS Number for 217 W Bay Street, Winter Garden, Florida is S5149527.
The price for 217 W Bay Street, Winter Garden, Florida is $1,395,000.
The status of 217 W Bay Street, Winter Garden, Florida is Active.
The subdivision of 217 W Bay Street, Winter Garden, Florida is Cooper & Sewell Add.
The home located at 217 W Bay Street, Winter Garden, Florida was built in 2026.