Homes for sale - 157 LAKE ROY DR, Winter Haven, FL 33884

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Jason Anderson

jason_anderson@kw.com +1(352) 848-4918

$ 919,000

Est. payment | -/mo

5 Beds

5 Baths

3,839 SqFt

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$ 919,000

Est. payment | -/mo

Save Virtual Tour

5 Beds

5 Baths

3,839 SqFt

Key Details

Property Type Single Family Home

Sub Type Single Family Residence

Listing Status Active

Purchase Type For Sale

Square Footage 3,839 sqft

Price per Sqft $239

Subdivision Eloise Woods Lake Roy Unit

MLS Listing ID L4957283

Bedrooms 5

Full Baths 3

Half Baths 2

Construction Status Completed

HOA Y/N No

Year Built 1987

Annual Tax Amount $8,990

Lot Size 0.650 Acres

Acres 0.65

Lot Dimensions 137x188

Property Sub-Type Single Family Residence

Source Stellar MLS

Property Description

One or more photo(s) has been virtually staged. Experience prime lakefront living on the world-famous Winter Haven Chain of Lakes at 157 Lake Roy Drive—one of the most exceptional and hard-to-find properties to come on the market. Perfectly positioned on a quiet, crystal-clear lake with direct access to more than 20 connected lakes, this rare compound brings together a spacious 3,289 sqft main residence (4 beds/4 baths), a 550 sqft detached apartment (1 bed/1 bath), unmatched parking and storage capacity (15+ vehicles), and premier lakefront amenities—all on a waterfront setting that is nearly impossible to duplicate in Central Florida. Thoughtfully updated and meticulously cared for, the property features new roofs on both structures (2018), complete replumbing (2019), new flooring throughout (2020), remodeled bathrooms (2020), a brand-new 2-ton A/C system in the apartment (2025), new irrigation pump (2023), upgraded landscape lighting (2025), natural-gas pool/spa heater (2019), and much more. Inside the main residence, generous living spaces blend warmth, comfort, and functionality, creating a home designed equally for everyday relaxation and large-scale entertaining. The spacious kitchen offers abundant cabinetry, a center cooking island, breakfast bar, and a lakeview dinette positioned to capture nightly sunsets. Formal living and dining rooms accommodate gatherings with ease, while the inviting family room—with its brick natural-gas fireplace—creates a cozy backdrop for daily living. The primary suite includes dual walk-in closets, split vanities, a jetted tub, and a large walk-in shower. Secondary bedrooms are well-sized, and the home's storage capacity is exceptional throughout. Where this property truly separates itself is outdoor living and entertainment potential. A natural gas–heated pool and spa, expansive covered and open decking, a cabana bath, panoramic sunset views, and a private boathouse with lift all come together to create a setting purpose-built for unforgettable gatherings. The extensive parking allows for 15+ vehicles, making this one of the few lakefront homes able to comfortably host large groups for holidays, events, and waterfront entertaining. Thoughtful landscape lighting sets a warm evening ambiance, highlighting the home's beauty long after sunset. Car collectors, hobbyists, and those needing significant workspace will appreciate the attached 29x21 garage with a 29x6 storage room, plus the massive 25x27 detached garage/workshop engineered with a vaulted ceiling suitable for a lift. The RV pad with 30-amp service adds even more versatility. Perfect for multi-generational living, long-term guests, or private accommodations during holidays and special events, the detached apartment includes its own living room, bedroom, and full bath and is serviced by a brand-new 2-ton A/C system (2025). Located on Lake Roy—one of the quietest and clearest lakes on the Chain—the property offers direct access to boating, fishing, lakefront dining, live music, and even seasonal LEGOLAND fireworks. A public boat ramp just one house away provides unmatched convenience for launching and retrieving boats. Ideally situated between Tampa and Orlando, Winter Haven blends a vibrant small-town lifestyle with boutique dining, cultural events, and year-round recreation. 157 Lake Roy Drive is more than a lakefront home—it's a rare waterfront compound offering space, privacy, storage, updates, entertainment capacity, and true Chain of Lakes living in one extraordinary package.

Location

State FL

County Polk

Community Eloise Woods Lake Roy Unit

Area 33884 - Winter Haven / Cypress Gardens

Zoning R-1

Rooms

Other Rooms Family Room, Formal Dining Room Separate, Formal Living Room Separate, Garage Apartment, Inside Utility

Interior

Interior Features Ceiling Fans(s), Eat-in Kitchen, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)

Heating Central, Electric

Cooling Central Air

Flooring Carpet, Laminate, Tile

Fireplaces Type Family Room, Gas

Fireplace true

Appliance Built-In Oven, Cooktop, Dryer, Gas Water Heater, Microwave, Refrigerator, Washer

Laundry Laundry Room

Exterior

Exterior Feature Lighting, Sliding Doors, Storage

Parking Features Boat, Circular Driveway, Converted Garage, Driveway, Garage Door Opener, Garage Faces Side, RV Access/Parking

Garage Spaces 4.0

Pool Gunite, Heated, In Ground

Utilities Available Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected

Waterfront Description Lake Front,Lake Privileges

View Y/N Yes

Water Access Yes

Water Access Desc Lake,Lake - Chain of Lakes

View Water

Roof Type Shingle

Porch Covered, Rear Porch, Screened

Attached Garage true

Garage true

Private Pool Yes

Building

Lot Description In County, Paved

Entry Level One

Foundation Slab

Lot Size Range 1/2 to less than 1

Sewer Septic Tank

Water Public

Architectural Style Custom

Structure Type Brick,Frame

New Construction false

Construction Status Completed

Schools

Elementary Schools Chain O Lakes Elem

Middle Schools Denison Middle

High Schools Lake Region High

Others

Pets Allowed Yes

Senior Community No

Ownership Fee Simple

Acceptable Financing Cash, Conventional, VA Loan

Listing Terms Cash, Conventional, VA Loan

Special Listing Condition None

Virtual Tour https://www.propertypanorama.com/instaview/stellar/L4957283

Listed by Michael Stone THE STONES REAL ESTATE FIRM

GET MORE INFORMATION

Jason Anderson

REALTOR® | Lic# SL3413061

jason_anderson@kw.com

+1(352) 848-4918

1918 SE 17th Street, Ocala FL 34471

157 LAKE ROY DR Winter Haven, FL 33884

Jason Anderson

Key Details

Location

Rooms

Interior

Exterior

Building

Schools

Others

157 LAKE ROY DR