157 Lake Roy Drive, Winter Haven, FL 33884
Local realty services provided by:CENTURY 21 Selling Paradise
Listed by: michael stone, deanna stone
Office: the stones real estate firm
MLS#:L4957283
Source:MFRMLS
Price summary
- Price:$919,000
- Price per sq. ft.:$201.62
About this home
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.
Contact an agent
Home facts
- Year built:1987
- Listing ID #:L4957283
- Added:28 day(s) ago
- Updated:December 14, 2025 at 01:23 PM
Rooms and interior
- Bedrooms:5
- Total bathrooms:5
- Full bathrooms:3
- Half bathrooms:2
- Living area:3,839 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central, Electric
Structure and exterior
- Roof:Shingle
- Year built:1987
- Building area:3,839 sq. ft.
- Lot area:0.65 Acres
Schools
- High school:Lake Region High
- Middle school:Denison Middle
- Elementary school:Chain O Lakes Elem
Utilities
- Water:Public, Water Connected
- Sewer:Septic Tank
Finances and disclosures
- Price:$919,000
- Price per sq. ft.:$201.62
- Tax amount:$8,990 (2025)
New listings near 157 Lake Roy Drive
- New
$359,000Active5 beds 3 baths2,696 sq. ft.246 Meadowbrook Boulevard, WINTER HAVEN, FL 33881
MLS# S5140218Listed by: EXP REALTY LLC - New
$120,000Active1 beds 1 baths792 sq. ft.2025 San Marcos Drive Se #27, WINTER HAVEN, FL 33880
MLS# L4957911Listed by: CENTURY 21 MYERS REALTY - New
$320,000Active3 beds 2 baths1,622 sq. ft.4955 Old Lucerne Park Road, WINTER HAVEN, FL 33881
MLS# O6364911Listed by: AROD PARTNERS REALTY - New
$279,990Active3 beds 2 baths1,639 sq. ft.302 La Serena, WINTER HAVEN, FL 33884
MLS# P4936970Listed by: KELLER WILLIAMS REALTY SMART 1 - New
$239,500Active2 beds 2 baths1,232 sq. ft.466 Muirfield Court, WINTER HAVEN, FL 33884
MLS# P4937243Listed by: CENTURY 21 MYERS REALTY LAKE WALES - New
$139,500Active2 beds 2 baths888 sq. ft.845 Orchid Springs Drive, WINTER HAVEN, FL 33884
MLS# S5140064Listed by: EXP REALTY LLC - New
$185,000Active2 beds 1 baths576 sq. ft.1607 2nd Street Se, WINTER HAVEN, FL 33880
MLS# P4937275Listed by: LA ROSA REALTY PRESTIGE - New
$499,000Active4 beds 3 baths2,221 sq. ft.404 Talamone Drive, WINTER HAVEN, FL 33884
MLS# P4937070Listed by: EXP REALTY LLC - New
$280,000Active3 beds 1 baths1,602 sq. ft.3022 Hickory Street Nw, WINTER HAVEN, FL 33881
MLS# A4674941Listed by: COMPASS FLORIDA LLC - New
$325,000Active3 beds 2 baths2,043 sq. ft.587 Drayton Road, WINTER HAVEN, FL 33884
MLS# L4957863Listed by: KELLER WILLIAMS REALTY SMART