157 LAKE ROY DRIVE, Winter Haven, FL 33884

• 5 beds |
• 5 baths |
• 3,839 sqft

Property Description

Lakefront pool home on the Winter Haven Chain of Lakes with a detached apartment, 4 car garage, abundant open parking, RV parking pad, pool, dock and more! Perfectly positioned on Lake Roy, one of the Chain’s quietest and clearest lakes, this property delivers sunset views, calm waters, and direct boat access to 20 canal-connected lakes for endless fishing, skiing, cruising, lakefront dining, live music, and seasonal LEGOLAND fireworks. The main residence features over 3,800 sqft of living space with 4 bedrooms, 2 full baths, and 2 half baths, plus a detached 550 sqft apartment with its own living room, bedroom, and bath—ideal for guests and extended family. Inside the main home, formal living and dining spaces lead to a well-equipped kitchen with center island, breakfast bar, abundant cabinetry, and a lakeview dinette designed to capture nightly sunsets. The inviting family room—with its brick natural-gas fireplace—adds warmth and comfort for everyday living. The primary suite offers dual walk-in closets, split vanities, a jetted tub, and walk-in shower, while secondary bedrooms provide generous space and excellent storage. Outdoor living is where this property excels. Enjoy a natural gas–heated pool and spa, expansive covered and open decking, cabana bath, panoramic lake views, and a private boathouse with lift—creating the ultimate lakefront playground. A public boat ramp just one home away adds exceptional convenience. Major updates ensure peace of mind, including: new roofs on both structures (2018), complete replumbing (2019), new flooring throughout (2020), remodeled bathrooms (2020), new irrigation pump (2023), upgraded landscape lighting (2025), natural-gas pool/spa heater (2019), and a brand-new 2-ton A/C in the apartment (2025). Located between Tampa and Orlando, this property offers the perfect blend of small-town charm, recreation, and waterfront living. 157 Lake Roy Drive is more than a home—it’s a fully updated lakefront compound offering space, versatility, and true Winter Haven Chain of Lakes lifestyle.

Listing Status:

Pending

Date Added:

November 15, 2025

Data Last Updated:

February 11, 2026 at 3:23AM

Listing Office:

THE STONES REAL ESTATE FIRM : 863-412-2080

Listing Agent:

Michael Stone : 863-412-9733

MLS ID:

L4957283

Interior

• General: Ceiling Fans(s)Eat-in KitchenPrimary Bedroom Main FloorStone CountersWalk-In Closet(s)
• Rooms: Family RoomFormal Dining Room SeparateFormal Living Room SeparateGarage ApartmentInside Utility
• Appliances: Built-In OvenCooktopDryerGas Water HeaterMicrowaveRefrigeratorWasher
• Laundry: Laundry Room
• Flooring: CarpetLaminateTile
• A/C: Central Air
• Heating: CentralElectric
• Fireplace: Family RoomGasFireplace

Exterior

• General: LightingSliding DoorsStorageHeatedIn Ground
• Style: Custom
• Other Structures: Boat HouseGuest HouseStorageRear PorchScreenedCovered
• Pool: GuniteHeatedIn Ground
• Parking: BoatCircular DrivewayConverted GarageDrivewayGarage Door OpenerGarage Faces SideRV Access/Parking

Construction

• Roofing: Shingle
• Windows: BlindsShades
• General: BrickFrameOneSlab

Location

• Road/Access: Paved
• Originating MLS: Stellar MLS
• County: Polk

Lot

• Zoning: R-1ELOISE WOODS LAKE ROY UNIT PB 14 PG 19 19A 19B LOTS 15 & 1626-28-34-660000-000150
• View: Water

Utilities

• Utilities: Cable ConnectedElectricity ConnectedNatural Gas ConnectedWater Connected
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple