240 SANTA ROSA DRIVE, Winter Haven, FL 33884

• 4 beds |
• 3 baths |
• 2,850 sqft

Property Description

***NEW PRICE DROP*** Discover a remarkable private home in Winter Haven’s premier Overlook Estates. This spacious 4-bedroom, 2.5 bath residence boasts 2,850 square feet of elegant living space, featuring highly desirable outdoor amenities within an established and coveted neighborhood. Built in 1988, the house combines classic style with significant modern enhancements. Inside, you’ll find soaring ceilings, generous rooms, and abundant sunlight that together create a refined yet welcoming setting, perfect for daily life or entertaining guests. Its open design effortlessly connects formal areas with casual ones, providing ample options for social gatherings, home offices, or multi-generational living arrangements. At the heart of the home is a well-equipped kitchen, offering plenty of cabinetry and counter area, plus direct access to the outdoor entertainment spaces. The large primary suite serves as a peaceful sanctuary with its own en-suite bath and walk-in closet, while three additional bedrooms provide flexibility for family, guests, or other uses. Step outside into your secluded backyard retreat, which includes a sparkling saltwater pool, detached hot tub, bar or pool house, and extensive patio ideal for relaxing or hosting year-round events, a true representation of Florida lifestyle. Major recent updates add both security and enduring value: a new roof (2018), updated drain field and septic system (2024), and a brand-new second-floor air conditioning system (2025) ensure ongoing comfort and reliability. Perfectly located just minutes from the Chain of Lakes, golf courses, shops, restaurants, and main routes to Tampa and Orlando, this home offers unparalleled prestige, privacy, and convenience. Don’t miss this rare chance to own a luxurious, spacious, and upgraded residence in one of Winter Haven’s top communities. Schedule your private visit today before this outstanding property is sold.

Listing Status:

Active

Date Added:

December 24, 2025

Data Last Updated:

February 10, 2026 at 12:22AM

Listing Office:

LIVE FLORIDA REALTY : 863-868-8905

Listing Agent:

Brian Surrency : 863-204-4298

MLS ID:

L4958092

Interior

• General: Cathedral Ceiling(s)Ceiling Fans(s)Crown MoldingHigh CeilingsPrimaryBedroom UpstairsSplit BedroomWalk-In Closet(s)
• Rooms: AtticFamily RoomFlorida RoomFormal Dining Room SeparateFormal Living Room SeparateInside Utility
• Appliances: DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRefrigeratorWasher
• Laundry: Inside
• Flooring: CarpetCeramic Tile
• A/C: Central Air
• Heating: Central
• Fireplace: Family RoomLiving RoomWood BurningFireplace

Exterior

• General: Fire PitOutdoor ShowerRain GuttersStorageAbove GroundHeated
• Style: Traditional
• Other Structures: Shed(s)PorchPatioCovered
• Pool: GuniteIn GroundSalt Water
• Parking: Garage Door Opener

Construction

• Roofing: Shingle
• Windows: BlindsWindow Treatments
• General: FrameWood SidingTwoSlab

Location

• Road/Access: Paved
• HOA Amenities: Gated550.0Annually
• Originating MLS: Stellar MLS
• County: Polk

Lot

• Zoning: 0OVERLOOK ESTATES PHASE 3 PB 83 PG 50 LOT 2226-28-35-662927-000220
• Fencing: Fenced

Utilities

• Utilities: Cable AvailableElectricity ConnectedFire HydrantSprinkler Well
• Water: Public
• Sewer: Septic Tank

Financial

• Source: Stellar MLS
• Ownership: Fee Simple