240 SANTA ROSA DRIVE WINTER HAVEN FL 33884 MLS #L4958092

240 SANTA ROSA DRIVE
WINTER HAVEN, FL, 33884
$445,000
4 Beds
2.5 Baths
2,850 SqFt
0.28 Acres
Add
MLS #L4958092 image #0
Luxury Meets Paradise in Winter Haven’s Exclusive Overlook Estates!

Experience the pinnacle of Florida living in this exceptional 4-bedroom, 2.5-bath pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community.

Originally built in 1988, this residence masterfully blends timeless elegance with impressive modern upgrades, delivering move-in-ready comfort and lasting value. The inviting open-concept layout features soaring ceilings, expansive rooms bathed in natural light, and seamless flow between formal and casual areas, ideal for effortless entertainment, relaxed family gatherings, a dedicated home office, or accommodating multi-generational living.

The heart of the home shines with a spacious, functional kitchen boasting abundant cabinetry, generous counter space, and convenient direct access to the incredible outdoor retreat. Retreat to the serene primary suite, your personal oasis complete with a private en-suite bath and large walk-in closet, while the three additional versatile bedrooms allow endless possibilities for family, guests, hobbies, or more.

Outside awaits your own private Florida paradise: a pristine saltwater pool, separate hot tub, dedicated poolside bar or pool house, and a sprawling patio perfect for year-round al fresco dining, BBQs, lounging, or hosting unforgettable events under the Florida sun.

Recent high-value updates provide total peace of mind: new roof (2018), fully updated septic system and drain field (2024), and a brand-new air conditioning system (2025), ensuring efficiency, reliability, and low-maintenance enjoyment for years to come.

Nestled in one of Winter Haven’s most coveted communities, you’re just minutes from the world-famous Chain of Lakes (boating, fishing, kayaking, and endless water recreation), championship golf courses, premier shopping, diverse dining, and easy commutes to Tampa, Orlando, and beyond, including nearby Legoland thrills.

This is the rare opportunity you’ve been waiting for: a spacious, impeccably updated, ultra-private luxury home in a top-tier location. Properties like this sell fast, don’t wait! Schedule your exclusive showing today and make this dream residence yours before it’s gone.

Property Details

Price:
$445,000
MLS #:
L4958092
Status:
Active
Beds:
4
Baths:
2.5
Type:
Single Family
Subtype:
Single Family Residence
Subdivision:
OVERLOOK ESTS PH 3
Neighborhood:
33884winterhavencypressgardens
Listed Date:
Dec 24, 2025
Finished Sq Ft:
2,850
Total Sq Ft:
4,216
Lot Size:
12,350 sqft / 0.28 acres (approx)
Year Built:
1988
TraditionalPoolCommunity Gated33884 – Winter Haven / Cypress Gardens33884winterhavencypressgardensOverlook Ests Ph 3Elbert ElemDenison MiddleWinter Haven SeniorPlease Verify With HoaNo MinimumPets Allowed

Ask a Question

See this Listing

Send
  

Schools

Elementary School:
Elbert Elem
Middle School:
Denison Middle
High School:
Winter Haven Senior

Interior

Appliances
Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
Bathrooms
2 Full Bathrooms, 1 Half Bathroom
Cooling
Central Air
Flooring
Carpet, Ceramic Tile
Heating
Central
Laundry Features
Inside

Exterior

Architectural Style
Traditional
Association Amenities
Gated
Community Features
Deed Restrictions, Gated Community – No Guard
Construction Materials
Wood Frame, Wood Siding
Exterior Features
Fire Pit, Irrigation System, Outdoor Shower, Rain Gutters, Storage
Other Structures
Shed(s)
Parking Features
Garage Door Opener
Roof
Shingle
Security Features
Gated Community

Financial

HOA Fee
$550
HOA Frequency
Annually
HOA Name
Overlook Estates
Tax Year
2023
Taxes
$2,790

Map

Community

Subdivisions in WINTER HAVEN

Market Summary

Current real estate data for Single Family in WINTER HAVEN as of Mar 18, 2026
841
Single Family Listed
119
Avg DOM
180
Avg $ / SqFt
$337,154
Avg List Price

Property Summary

    Located in the OVERLOOK ESTS PH 3 subdivision, 240 SANTA ROSA DRIVE WINTER HAVEN FL is a Single Family for sale in WINTER HAVEN, FL, 33884. It is listed for $445,000 and features 4 beds, 3 baths, and has approximately 2,850 square feet of living space, and was originally constructed in 1988. The current price per square foot is $156. The average price per square foot for Single Family listings in WINTER HAVEN is $180. The average listing price for Single Family in WINTER HAVEN is $337,154. To schedule a showing of MLS#l4958092 at 240 SANTA ROSA DRIVE in WINTER HAVEN, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.

Similar Listings Nearby

broker reciprocity
MLS# P4937228broker reciprocity
4025 SABLE LOOP DRIVE
LAKE WALES, FL

$575,000

4.7 miles away

broker reciprocity
MLS# S5143363broker reciprocity
191 BROAD STREET
WINTER HAVEN, FL

$550,000

2.6 miles away

broker reciprocity
MLS# P4936596broker reciprocity
4004 SABLE LOOP DRIVE
LAKE WALES, FL

$549,900

4.7 miles away

broker reciprocity
MLS# P4937366broker reciprocity
4189 LIMERICK DRIVE
LAKE WALES, FL

$549,000

4.8 miles away

broker reciprocity
MLS# O6318340broker reciprocity
209 7TH STREET S
HAINES CITY, FL

$540,000

4.1 miles away

broker reciprocity
MLS# P4937380broker reciprocity
4105 LIMERICK DRIVE
LAKE WALES, FL

$535,000

4.6 miles away

240 SANTA ROSA DRIVE
WINTER HAVEN, FL