240 Santa Rosa Drive, Winter Haven, FL 33884
Local realty services provided by:ERA American Suncoast
Listed by: brian surrency
Office: live florida realty
MLS#:L4958092
Source:MFRMLS
Price summary
- Price:$446,700
- Price per sq. ft.:$105.95
- Monthly HOA dues:$45.83
About this home
***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.
Contact an agent
Home facts
- Year built:1988
- Listing ID #:L4958092
- Added:50 day(s) ago
- Updated:February 13, 2026 at 01:50 PM
Rooms and interior
- Bedrooms:4
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Living area:2,850 sq. ft.
Heating and cooling
- Cooling:Central Air
- Heating:Central
Structure and exterior
- Roof:Shingle
- Year built:1988
- Building area:2,850 sq. ft.
- Lot area:0.28 Acres
Schools
- High school:Winter Haven Senior
- Middle school:Denison Middle
- Elementary school:Elbert Elem
Utilities
- Water:Public
- Sewer:Septic Tank
Finances and disclosures
- Price:$446,700
- Price per sq. ft.:$105.95
- Tax amount:$2,790 (2023)
New listings near 240 Santa Rosa Drive
- New
$235,000Active2 beds 2 baths1,161 sq. ft.31 Cactus Circle N, WINTER HAVEN, FL 33880
MLS# L4959400Listed by: BHHS FLORIDA PROPERTIES GROUP - Open Sat, 11am to 2pmNew
$290,000Active3 beds 2 baths1,675 sq. ft.4018 Cypress Landing S, WINTER HAVEN, FL 33884
MLS# TB8475857Listed by: LING REALTY, LLC - New
$129,000Active2 beds 2 baths1,496 sq. ft.4204 Cedarwood Street, WINTER HAVEN, FL 33880
MLS# P4937790Listed by: COLDWELL BANKER REALTY - New
$130,000Active2 beds 2 baths1,104 sq. ft.4056 Rolling Oaks Drive, WINTER HAVEN, FL 33880
MLS# P4937783Listed by: COLDWELL BANKER REALTY - New
$387,500Active4 beds 2 baths2,078 sq. ft.5828 Marsh Landing Drive, WINTER HAVEN, FL 33881
MLS# L4958953Listed by: FLORIDA REAL ESTATE COMPANY - New
$225,000Active2 beds 2 baths1,118 sq. ft.3343 Livingston Way, WINTER HAVEN, FL 33884
MLS# P4937723Listed by: CENTURY 21 MYERS REALTY LAKE WALES - New
$247,000Active3 beds 2 baths1,238 sq. ft.5750 Harbor Isle Boulevard, WINTER HAVEN, FL 33884
MLS# S5143689Listed by: RE/MAX HERITAGE PROFESSIONALS - New
$235,000Active3 beds 2 baths1,230 sq. ft.606 Holt Circle, WINTER HAVEN, FL 33880
MLS# L4959309Listed by: KELLER WILLIAMS REALTY SMART 1 - New
$477,555Active4 beds 2 baths2,428 sq. ft.1051 Lena Run Court, WINTER HAVEN, FL 33880
MLS# L4959294Listed by: COLDWELL BANKER REALTY - New
$249,900Active2 beds 2 baths1,531 sq. ft.447 San Jose Drive, WINTER HAVEN, FL 33884
MLS# P4937807Listed by: COLDWELL BANKER REALTY