157 LAKE ROY DRIVE Winter Haven, FL $ 919,000
157 LAKE ROY DRIVE
$ 919,000
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157 LAKE ROY DRIVE

Winter Haven, FL, 33884
$ 919,000
Bedrooms5 Baths3.2 Sq 3,839

Monthly Estimate*

$ 5,733

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Single Family Home for sale in Winter Haven, FL

for $919,000 with 5 bedrooms and 3 full baths, 2 half baths. This 3,839 square foot home was built in 1987 on a lot size of 0.65.

One or more photo(s) has been virtually staged. Welcome to 157 Lake Roy Drive—a rare lakefront offering on the world-famous Winter Haven Chain of Lakes. 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.

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Single Family Active

Price

$ 919,000

Bedrooms

5

Full Bath

3

Half Bath

2

Property Type

Single Family

Taxes

$ 8,990

Style

Custom

Lot Size

0.65

Year Built

1987

Town/City

Winter Haven

County/Region

Polk

MLS | Web ID

L4957283

Features
General
Sewer Septic Tank
Heating Central Electric
Cooling Central Air
Utilities Cable Connected Electricity Connected Natural Gas Connected Water Connected
Possession Close Of Escrow
Roof Shingle
Appliances Built-In Oven Cooktop Dryer Gas Water Heater Microwave Refrigerator Washer
Zoning R-1
Garage Spaces 4
Patio/Porch Features Covered Rear Porch Screened
Architectural Style Custom
Pool Features Gunite Heated In Ground
Construction Materials Brick Wood Frame
Pets Allowed Yes
Year Built 1987
View Water
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
Waterfront Features Lake Front Lake - Chain of Lakes
County Polk
New Construction false
Property Type Residential
Attached Garage true
Subdivision Name ELOISE WOODS LAKE ROY UNIT
Facing Direction Southeast
Garage Y/N true
Other Structures Boat House Guest House Storage
Total Rooms 12
Full Baths 3
Status Active
Directions Cypress Gardens Blvd - South on Hillcrest which turns into Lake Roy Dr - Home will be down on your right
High School Lake Region High
City WINTER HAVEN
Body of Water LAKE ROY
Senior Community Y/N false
MLS Area 33884 - Winter Haven / Cypress Gardens
Lot Size Units Square Feet
Lot Size Square Feet 28192
Carport Y/N false
Listing Terms Cash Conventional VA Loan
Spa Features Heated In Ground
Elementary School Chain O Lakes Elem
Land Lease Y/N false
Tax Annual Amount 8990.13
Middle/Junior High School Denison Middle
Property Condition Completed
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/L4957283
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Active
Occupancy Type Owner
Tax Lot 15
Legal Description ELOISE WOODS LAKE ROY UNIT PB 14 PG 19 19A 19B LOTS 15 & 16
Water View Lake Lake - Chain of Lakes
Water Access Type Lake Lake - Chain of Lakes
Minimum Lease 6 Months
Water Access Y/N true
Additional Rooms Family Room Formal Dining Room Separate Formal Living Room Separate Garage Apartment Inside Utility
ILS Total SQFT 550
ILS Under Air SQFT 550
Water View Y/N true
Flood Zone Code X
DockY/N true
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Interior
Interior Amenities Ceiling Fan(s) Eating Space In Kitchen Primary Bedroom Main Floor Stone Counters Walk-In Closet(s)
Flooring Carpet Laminate Tile
Fireplace Features Family Room Gas
Air Conditioning Y/N true
Heating Y/N true
Window Features Blinds Shades
Fireplace Y/N true
Half Baths 2
Laundry Features Laundry Room
Total Bedrooms 5
Total Baths 5
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Exterior
Exterior Amenities Irrigation System Lighting Sliding Doors Storage
Vegetation Mature Landscaping Trees/Landscaped
Parking Features Boat Circular Driveway Converted Garage Driveway Garage Door Opener Garage Faces Side RV Parking
Lot Features In County
Water Source Public
Lot Size Area 28192
Foundation Details Slab
Spa true
Building Area Total 4558
Lot Dimensions 137 x 188
Lot Size Acres 0.65
Road Surface Type Paved
Private Pool true
Waterfront Y/N true
Covered Spaces 4
Road Frontage Type Street Paved
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* Excluded Features
List By
The Stones Real Estate Firm

Broker

info@soldbystones.com

Email

Affordability Calculator

$6,483
Per Month
88%
12%
0%
Monthly Principal & Interest
$5,733
Monthly Property Taxes
$749
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.375% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Lake Region High High School High School
Pricing History
DatePricePrice ChangeDescription
12/19/2025$919,000 Listed Price

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157 LAKE ROY DRIVE, Winter Haven, FL, 33884 is a Single Family Home for sale at $919,000 with 3,839 sqft and a lot size of 0.65. 157 LAKE ROY DRIVE has 5 bedrooms, 3.2 baths, and was built in 1987. The property's zip code is 33884 which is in Winter Haven, FL