Date
Details
Price
Change
Source
11/15/2025
Listed
$919,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$919,000
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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.
Full Property Details
Full Property Details for 157 Lake Roy Dr
General
- Price: $919,000
- Taxes: $8,990 (2025)
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: L4957283
- Updated: 12/30/2025
- Added to Site: 63 day(s) ago
Rental Information
- Min. Lease: 6 Months
Interior
- Number of Rooms: 12
- Interior Features: Ceiling Fan(s), Eating Space In Kitchen, Primary Bedroom Main Floor, Stone Counters, Walk-In Closet(s)
- Fireplace: Yes
- Fireplace(s): Family Room, Gas
- Appliances: Built-In Oven, Cooktop, Dryer, Gas Water Heater, Microwave, Refrigerator, Washer
- Flooring: Carpet, Laminate, Tile
Rooms
Bathrooms
- Total Bathrooms: 5
- Full Bathrooms: 3
- Half Bathrooms: 2
Bedrooms
- Total Bedrooms: 5
Other Rooms
- Laundry: Laundry Room
Additional Information
- Pool: Yes
- Private Pool: Yes
- Pool Description: Gunite, Heated, In Ground
- Spa: Yes
- Spa Description: Heated, In Ground
Exterior
- Exterior Features: Irrigation System, Lighting, Sliding Doors, Storage
- Deck/Patio: Covered, Rear Porch, Screened
- Porch/Patio/Deck: Covered, Rear Porch, Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 4
- Covered Spaces: 4
- Parking Features: Boat, Circular Driveway, Converted Garage, Driveway, Garage Door Opener, Garage Faces Side, RV Parking
Location
- Area: 33884 - Winter Haven / Cypress Gardens
- County: Polk
- Development Name: 33884 - Winter Haven / Cypress Gardens
- Subdivision: ELOISE WOODS LAKE ROY UNIT
- Driving Directions: Cypress Gardens Blvd - South on Hillcrest which turns into Lake Roy Dr - Home will be down on your right
- Direction Faces: Southeast
School Information
- Elementary School: Chain O Lakes Elem
- Middle School: Denison Middle
- High School: Lake Region High
Community
- Community Name: 33884 - Winter Haven / Cypress Gardens
- Pet Restrictions: Must contact the county to confirm all pet rules and restrictions.
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric
Utilities
- Sewer: Septic Tank
- Water District: LAKE ROY
- Water: Public
- Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Water Connected
Structural Information
- Architectural Info: Custom
- Architectural Style: Custom
- Exterior Const.: Brick, Wood Frame
- Roof: Shingle
- Windows: Blinds, Shades
- Stories/Levels: One
- Square Feet: 3,839
- Sq. Ft. Source: Public Records
- Year Built: 1987
Additional Structures
- Other Structures: Boat House, Guest House, Storage
Lot Features
- Property View: Water
- Lot Size (Acres): 0.65
- Lot Size (Sq. Ft.): 28,192
- Lot Size: 28192
- Lot Dimensions: 137 x 188
- Frontage: Street Paved
- Street/Road Desc.: Paved
Water Features
- Water Front: Yes
- Water View: Yes
- Water Access: Yes
- Water Access Desc: Lake, Lake - Chain of Lakes
- Water Extras: Yes
- Water Front Name: LAKE ROY
- Water Front Desc.: Lake Front, Lake - Chain of Lakes
Financial Considerations
- Tax Amount: $8,990.13
- Tax Year: 2025
Disclosures and Reports
- Ownership: Fee Simple
- Special Conditions: None
- Legal Description: ELOISE WOODS LAKE ROY UNIT PB 14 PG 19 19A 19B LOTS 15 & 16
- Flood Zone Info: X
- APN: 262834660000000150
- Property ID: 262834660000000150
Listed by The Stones Real Estate Firm
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Listing agents
— 157 Lake Roy Dr —
The Stones Real Estate Firm
The Stones Real Estate Firm
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 157 Lake Roy Dr
School District:Polk County School District
| Name | Grades | Distance |
|---|---|---|
Chain Of Lakes Elementary School 7001 State Highway 653, Winter Haven, FL 33884 | PK-5 | 3.5 mi |
Denison Middle School 400 Avenue A Southeast, Winter Haven, FL 33880 | 6-8 | 1.6 mi |
Lake Region High School 1995 Thunder Road, Eagle Lake, FL 33839 | 9-12 | 3 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 157 Lake Roy Dr
Tax History
Tax History for 157 Lake Roy Dr
Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,017
6%
$640,652
1%
2023
$8,521
20%
$635,507
36%
2021
$7,129
-15%
$466,337
-30%
2022
$8,340
17%
$664,094
56%
2021
$7,129
1%
$426,682
-5%
2019
$7,063
8%
$447,708
2%
2017
$6,514
—
$437,703
7%
2017
$6,514
4%
$409,658
6%
2016
$6,242
4%
$385,269
7%
2015
$6,021
2%
$361,358
2%
2014
$5,881
2%
$353,287
4%
2013
$5,765
—
$338,327
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 157 Lake Roy Dr
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157 Lake Roy Drive, Winter Haven, FL 33884 (MLS# L4957283) is a Single Family property with 5 bedrooms, 3 full bathrooms and 2 partial bathrooms. 157 Lake Roy Drive is currently listed for $919,000 and was received on November 15, 2025. Want to learn more about 157 Lake Roy Drive? Do you have questions about finding other Single Family real estate for sale in Winter Haven? You can browse all Winter Haven real estate or contact a Coldwell Banker agent to request more information.