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240 Santa Rosa Drive

Winter Haven, FL 33884
  • $445,000
  • STATUS: Active
  • ON SITE: 77 Days
  • MLS #: L4958092
Price Reduced
$445,000
  • 4
    BEDS
  • 0.28
    ACRES
  • 2
    BATHS
  • 1
    1/2 BATHS
  • 2,850
    SQFT
  • $156
    $/SQFT
Neighborhood:
Type:
Single-Family Home
Built:
1988
County:

School Information

Elementary School:
Middle School:
High School:

Description

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 second-floor 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.

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© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-11T23:46:15.48.
www.hesseteam.com/homes/171573702
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240 Santa Rosa Drive Winter Haven, FL 33884

  • Price: $445,000
  • Status: Active
  • On Site: 77 Days
  • MLS #: L4958092
4
Beds
2
Baths
1
½ Baths
0.28
Acres
2,850
SQFT
$156
$/SQFT
1988
Built
Neighborhood:
Overlook Ests Ph 3
County:
Polk
Area:
Winter Haven / Cypress Gardens
Elementary School:
Elbert Elem
Middle School:
Denison Middle
High School:
Winter Haven Senior
Property Description
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 second-floor 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.
Exterior Features

Architectural Style Traditional Attached Garage Yn Yes Carport Yn No Construction Materials Wood FrameWood Siding Covered Spaces 2 Direction Faces South Exterior Features Fire PitIrrigation SystemOutdoor ShowerRain GuttersStorage Fencing Fenced Foundation Details Slab Lot Features In CountyLandscaped Lot Size Dimensions 95.0 x 130.0 Other Structures Shed(s) Parking Features Garage Door Opener Patio And Porch Features CoveredPatioPorch Pool Features GuniteIn GroundSalt Water Pool Private Yn Yes Road Frontage Type Street Paved Road Surface Type Paved Roof Shingle Spa Features Above GroundHeated Spa YN Yes Water Access Yn No Water Extras Yn No Water View Yn No Waterfront Feet Total 0 Waterfront Yn No

Interior Features

Additional Rooms AtticFamily RoomFlorida RoomFormal Dining Room SeparateFormal Living Room SeparateInside Utility Appliances DishwasherDisposalDryerGas Water HeaterMicrowaveRangeRefrigeratorWasher Building Area Total 4216 Cooling Central Air Cooling YN Yes Fireplace Features Family RoomLiving RoomWood Burning Fireplace Yn Yes Flooring CarpetCeramic Tile Furnished Unfurnished Heating Central Heating YN Yes Interior Features Cathedral Ceiling(s)Ceiling Fan(s)Crown MoldingHigh CeilingsPrimaryBedroom UpstairsSplit BedroomWalk-In Closet(s) Laundry Features Inside Levels Two Rooms Bedroom 2 (Built-in Closet) Bedroom 3 (Built-in Closet) Bedroom 4 (Built-in Closet) Bonus Room (No Closet) Dining Room Kitchen (Pantry) Family Room Primary Bathroom (Dual SinksShower No Tub) Living Room Primary Bedroom (Walk-In Closet(s)) Bathroom 2 Sewer Septic Tank Water Source Public Window Features BlindsWindow Treatments

Property Features

Additional Lease Restrictions Please verify with HOA Association Amenities Gated Association Approval Required Yn No Association Fee 550 Association Fee Frequency Annually Association Fee Monthly Amount 45.83 Association Fee Requirement Required Association Yn Yes Cdd Yn No Community Features Deed RestrictionsGated Community - No Guard Down Payment Resource Yes Flood Zone Code X Garage Yn Yes Homestead Yn Yes Lease Considered YN Yes Lease Restrictions YN No Listing Terms CashConventionalFHAVA Loan Minimum Lease No Minimum New Construction Yn No Ownership Fee Simple Pet Restrictions Please verify with HOA Pets Allowed Yes Property Sub Type Single Family Residence Realtor Info As-IsList Agent is Owner Security Features Gated Community Senior Community Yn No Special Listing Conditions None Sw Subdiv Community Name Not Applicable Tax Annual Amount 2790 Total Annual Fees 550 Total Monthly Fees 45.83 Utilities Cable AvailableElectricity ConnectedFire HydrantSprinkler Well Yrs Of Owner Prior To Leasing Re No Zoning 0


Listing information © 2026 My Florida Regional MLS DBA Stellar MLS..
Listing provided courtesy of LIVE FLORIDA REALTY: 863-868-8905.



© 2026 My Florida Regional MLS DBA Stellar MLS. All rights reserved. All listings displayed pursuant to IDX. All listing information is deemed reliable but not guaranteed and should be independently verified through personal inspection by appropriate professionals. Listings displayed on this website may be subject to prior sale or removal from sale; availability of any listing should always be independently verified. Listing information is provided for consumers personal, non-commercial use, solely to identify potential properties for potential purchase; all other use is strictly prohibited and may violate relevant federal and state law. Data last updated 2026-03-11T23:46:15.48.
 
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