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For sale
    • Price increase: $6K (9/30)
    $445,000

    240 SANTA ROSA DRIVE, WINTER HAVEN, FL 33884

    4beds
    2,850sqft
    : 
    $3,081/mo
    Get pre-qualified
    Single Family Residence
    Built in 1988
    0.28 Acres Lot
    $-- Zestimate®
    $156/sqft
    $46/mo HOA

    What's special

    Pool home
    Back on the market! Beautiful 4 bedroom, 2 1/2-bathroom, pool home with new roof (2024), septic (2024), A/C (2025) in gated Overlook Estates. Fresh price reduction, bring your offers! Experience the pinnacle of Florida living in this exceptional pool home, offering 2,850 sq ft of light-drenched space in the established Overlook Estates neighborhood, where privacy and prestige define the community. This is the rare opportunity you've been waiting for: a spacious, ultra-private luxury home in a top-tier location. Schedule your showing today and make this dream residence yours before it's gone.
    296 days
    188
    15

    Zillow last checked:

    Listing updated:

    Listed by:

    Brian Surrency 863-204-4298,

    LIVE FLORIDA REALTY 863-868-8905

    Source: Stellar MLS,MLS#: L4958092MLS LogoOriginating MLS: Suncoast Tampa

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Attic, Family Room, Florida Room, Dining Room, Living Room, Utility Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: Second
      • Area: 351 Square Feet
      • Dimensions: 27x13
      Bedroom 2
      • Features: Built-in Closet
      • Level: Second
      • Area: 165 Square Feet
      • Dimensions: 15x11
      Bedroom 3
      • Features: Built-in Closet
      • Level: Second
      • Area: 143 Square Feet
      • Dimensions: 13x11
      Bedroom 4
      • Features: Built-in Closet
      • Level: Second
      • Area: 180 Square Feet
      • Dimensions: 18x10
      Primary bathroom
      • Features: Dual Sinks, Shower No Tub
      • Level: Second
      • Area: 80 Square Feet
      • Dimensions: 8x10
      Bathroom 2
      • Level: Second
      • Area: 80 Square Feet
      • Dimensions: 8x10
      Bonus room
      • Features: No Closet
      • Level: First
      • Area: 300 Square Feet
      • Dimensions: 12x25
      Dining room
      • Level: First
      • Area: 154 Square Feet
      • Dimensions: 14x11
      Family room
      • Level: First
      • Area: 420 Square Feet
      • Dimensions: 28x15
      Kitchen
      • Features: Pantry
      • Level: First
      • Area: 221 Square Feet
      • Dimensions: 17x13
      Living room
      • Level: First
      • Area: 210 Square Feet
      • Dimensions: 14x15
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Gas Water Heater, Microwave, Range, Refrigerator, Washer
      • Laundry: Inside
      Features
      • Cathedral Ceiling(s), Ceiling Fan(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Split Bedroom, Walk-In Closet(s)
      • Flooring: Carpet, Ceramic Tile
      • Doors: Outdoor Shower
      • Has fireplace: Yes
      • Fireplace features: Family Room, Living Room, Wood Burning
      Interior area
      • Total structure area: 4,216
      • Total interior livable area: 2,850 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Covered, Patio, Porch
      • Exterior features: Fire Pit, Irrigation System, Outdoor Shower, Rain Gutters, Storage
      • Has private pool: Yes
      • Pool features: Gunite, In Ground, Salt Water
      • Has spa: Yes
      • Spa features: Above Ground, Heated
      • Fencing: Fenced
      Lot
      • Size: 0.28 Acres
      • Dimensions: 95.0 x 130.0
      • Features: In County, Landscaped
      • Residential vegetation: Mature Landscaping, Trees/Landscaped
      Details
      • Additional structures: Shed(s)
      • Parcel number: 262835662927000220
      • Zoning: 0
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Wood Frame, Wood Siding
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1988

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, Fire Hydrant, Sprinkler Well

      Community & HOA

      Community
      • Features: Deed Restrictions, Gated Community - No Guard
      • Security: Gated Community
      • Pet fee: $0 monthly
      • Subdivision: OVERLOOK ESTS PH 3
      HOA
      • Has HOA: Yes
      • Amenities included: Gated
      • HOA fee: $46 monthly
      • HOA name: Overlook Estates
      • HOA phone: 717-855-3110
      Location
      • Region: Winter Haven

      Financial & listing details

      • Price per square foot: $156/sqft
      • Tax assessed value: $358,676
      • Annual tax amount: $2,790
      • Date on market: 12/24/2025
      • Cumulative days on market: 172 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        9/30/2026Price change$445,000+1.4%$156/sqft
        Source: Stellar MLS #L4958092 Report a problem
        9/26/2026Pending sale$439,000$154/sqft
        Source: Stellar MLS #L4958092 Report a problem
        8/11/2026Listed for sale$439,000$154/sqft
        Source: Stellar MLS #L4958092 Report a problem
        7/8/2026Contingent$439,000$154/sqft
        Source: Stellar MLS #L4958092 Report a problem
        5/29/2026Pending sale$439,000$154/sqft
        Source: Stellar MLS #L4958092 Report a problem
        5/18/2026Price change$439,000+0.9%$154/sqft
        Source: Stellar MLS #L4958092 Report a problem
        3/24/2026Price change$434,900-2.3%$153/sqft
        Source: Stellar MLS #L4958092 Report a problem
        3/8/2026Price change$445,000-0.4%$156/sqft
        Source: Stellar MLS #L4958092 Report a problem
        2/6/2026Price change$446,700-0.7%$157/sqft
        Source: Stellar MLS #L4958092 Report a problem
        1/17/2026Price change$450,000-0.6%$158/sqft
        Source: Stellar MLS #L4958092 Report a problem
        1/2/2026Price change$452,900-2.2%$159/sqft
        Source: Stellar MLS #L4958092 Report a problem
        12/25/2025Listed for sale$462,900+5.2%$162/sqft
        Source: Stellar MLS #L4958092 Report a problem
        4/18/2024Sold$440,000-2.2%$154/sqft
        Source: Stellar MLS #L4941822 Report a problem
        3/6/2024Pending sale$450,000$158/sqft
        Source: Stellar MLS #L4941822 Report a problem
        1/31/2024Price change$450,000-4.1%$158/sqft
        Source: Stellar MLS #L4941822 Report a problem
        1/15/2024Listed for sale$469,000+115.6%$165/sqft
        Source: Stellar MLS #L4941822 Report a problem
        6/28/2013Sold$217,500+1.6%$76/sqft
        Source: Stellar MLS #P4625193 Report a problem
        4/20/2013Listed for sale$214,000+1.9%$75/sqft
        Source: Keller Williams Realty of Winter Haven #P4625193 Report a problem
        11/4/2012Listing removed$210,000$74/sqft
        Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem
        10/7/2012Price change$210,000-10.6%$74/sqft
        Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem
        7/4/2012Price change$234,900-4.1%$82/sqft
        Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem
        2/25/2012Listed for sale$245,000+32.4%$86/sqft
        Source: NORRIS & COMPANY REALTY, LLC #P4619759 Report a problem
        10/4/1999Sold$185,000$65/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,754 +102.1%$358,676 +61.5%
        2024$2,353 +2.2%$222,048 +3%
        2023$2,301 +2.2%$215,581 +3%
        2022$2,251 -0.4%$209,302 +3%
        2021$2,260 +0.9%$203,206 +1.4%
        2020$2,240 +0%$200,400 +2.3%
        2019$2,240 -15.6%$195,894 +1.9%
        2018$2,653 +1.9%$192,241 +2.1%
        2017$2,605 +21.5%$188,287 +2.1%
        2016$2,144 -1.7%$184,414 +0.7%
        2015$2,181 -8.9%$183,132 +0.8%
        2014$2,395 -7.8%$181,679 +12%
        2013$2,598 -0.8%$162,185 -1.6%
        2012$2,618 +24.2%$164,824 -2.7%
        2011$2,107 -5.6%$169,396 -3.2%
        2010$2,232 -14.6%$174,908 -8.2%
        2009$2,615 +7.2%$190,445 +0.1%
        2008$2,440 $190,255
        2007-- --
        2006$2,793 --
        2005-- --
        2004$2,468 +2.2%--
        2003$2,414 +0.3%$166,697 +2.4%
        2002$2,406 -14%$162,790 +1.6%
        2001$2,796 $160,150
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

        Explore the cost of this home by adjusting the details. Changes won't be saved.
        All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
        HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
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        Climate risks

        Neighborhood: Cypress Gardens

        Getting around

        1 / 100
        Car-Dependent
        26 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Elbert Elem
        • Middle: Denison Middle
        • High: Winter Haven Senior

        Source: Stellar MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.

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