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For sale
  • Price cut: $1K (8/3)
    $299,000

    5909 WINDSONG OAK DRIVE, LEESBURG, FL 34748

    3beds
    1,875sqft
    : 
    $2,068/mo
    Get pre-qualified
    Single Family Residence
    Built in 2013
    6,226 Square Feet Lot
    $295,800 Zestimate®
    $159/sqft
    $86/mo HOA

    What's special

    Virtually Staged. Lowest Price per foot in Windsong at Leesburg! Seller will put on a NEW Roof prior to closing with accepted contract! Welcome to 5909 Windsong Oak Drive NEAR the quiet culdesac in the very back of this quiet community, in the desirable Windsong at Leesburg community—where modern comfort, convenience, and Florida living come together beautifully. This move-in-ready home offers 1,875 square feet of thoughtfully designed living space featuring attractive stone accents, durable block-and-stucco construction, energy-efficient double-pane windows, and a spacious two-car garage. Step through the impressive foyer and discover an open-concept floor plan highlighted by large ceramic tile flooring, abundant natural light, and spacious gathering areas perfect for entertaining or everyday living. The heart of the home is the oversized kitchen featuring rich espresso cabinetry, granite countertops, stainless steel appliances, abundant prep space, and a large dining area ideal for family dinners and holiday celebrations. The expansive living room flows seamlessly to the large covered lanai through oversized sliding glass doors, creating the perfect indoor-outdoor lifestyle. Whether you're enjoying your morning coffee, relaxing after work, or hosting friends and family, this inviting space is designed to be enjoyed year-round. The oversized primary suite serves as a private retreat with plenty of room for a sitting area, a huge walk-in closet, and a luxurious ensuite bath featuring dual vanities, solid-surface countertops, a soaking tub, and a separate walk-in shower. Secondary bedrooms are with comfort and privacy, while the oversized laundry room provides additional storage and functionality. Beyond the home itself, Windsong at Leesburg offers exceptional community amenities with low HOA fees. Residents enjoy a beautiful community pool, covered seating and gathering areas, and a playground, creating the perfect setting for relaxation, recreation, and neighborhood gatherings. Location is another standout feature. Conveniently situated near Publix, shopping, restaurants, medical facilities, and daily conveniences, everything you need is just minutes away. Outdoor enthusiasts will appreciate the close proximity to public boat ramps and the area's beautiful lakes, providing endless opportunities for boating, fishing, kayaking, and waterfront fun. Commuters will love the easy drive to Clermont, Minneola, and surrounding Central Florida destinations, while wine enthusiasts can enjoy nearby weekends at Lakeridge Winery, one of Florida's premier wineries known for its scenic vineyards, festivals, and live entertainment. If you've been searching for a move-in-ready home in Leesburg with granite countertops, stainless steel appliances, an oversized primary suite, covered lanai, low HOA fees, community pool, playground, and convenient access to shopping, boating, and Clermont, then 5909 Windsong Oak Drive is the opportunity you've been waiting for. Schedule your private showing today and discover why this exceptional home stands out from the competition.
    69 days
    |
    364
    |
    25
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Corey Lott 407-222-0495,

    NEXTHOME LOTT PREMIER REALTY 407-222-0495

    Source: Stellar MLS,MLS#: O6411614MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 2
      • Full bathrooms: 2
      Rooms
      • Room types: Utility Room
      Primary bedroom
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 221 Square Feet
      • Dimensions: 17x13
      Bedroom 2
      • Features: Built-in Closet
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 12x11
      Bedroom 3
      • Features: Built-in Closet
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Dinette
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 10x12
      Kitchen
      • Features: Pantry
      • Level: First
      • Area: 120 Square Feet
      • Dimensions: 12x10
      Living room
      • Level: First
      • Area: 260 Square Feet
      • Dimensions: 20x13
      Heating
      • Central
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Microwave, Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Solid Wood Cabinets, Split Bedroom, Stone Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Carpet, Ceramic Tile
      • Doors: Sliding Doors
      • Has fireplace: No
      Interior area
      • Total structure area: 2,526
      • Total interior livable area: 1,875 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Rear Porch
      • Exterior features: Irrigation System, Sidewalk
      Lot
      • Size: 6,226 Square Feet
      • Features: Cleared, Sidewalk, Street Dead-End
      • Residential vegetation: Mature Landscaping
      Details
      • Parcel number: 242024230000008500
      • Zoning: RES
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2013

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: BB/HS Internet Available, Electricity Connected, Sewer Connected, Street Lights
      Green energy
      • Indoor air quality: Ventilation

      Community & HOA

      Community
      • Features: Community Mailbox, Playground, Pool
      • Pet fee: $0 monthly
      • Subdivision: WINDSONG AT LEESBURG
      HOA
      • Has HOA: Yes
      • Services included: Community Pool
      • HOA fee: $86 monthly
      • HOA name: Dave Ellis
      • HOA phone: 352-404-4116
      Location
      • Region: Leesburg

      Financial & listing details

      • Price per square foot: $159/sqft
      • Tax assessed value: $282,222
      • Annual tax amount: $3,578
      • Date on market: 5/30/2026
      • Cumulative days on market: 69 days
      • Listing terms: Cash,Conventional,FHA,USDA Loan,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        $295,800

        $281,000 - $311,000

        $2,033/mo

        Price history

        DateEventPrice
        8/3/2026Price change$299,000-0.3%$159/sqft
        Source: Stellar MLS #O6411614 Report a problem
        6/26/2026Price change$300,000-1.6%$160/sqft
        Source: Stellar MLS #O6411614 Report a problem
        6/18/2026Price change$305,000-3.2%$163/sqft
        Source: Stellar MLS #O6411614 Report a problem
        6/2/2026Price change$315,000+9%$168/sqft
        Source: Stellar MLS #O6411614 Report a problem
        5/30/2026Listed for sale$289,000+22.5%$154/sqft
        Source: Stellar MLS #O6411614 Report a problem
        7/12/2024Listing removed$236,000-0.8%$126/sqft
        Source: Stellar MLS #G5039124 Report a problem
        5/14/2021Sold$238,000+0.8%$127/sqft
        Source: Public Record Report a problem
        3/26/2021Pending sale$236,000$126/sqft
        Source: Stellar MLS #G5039124 Report a problem
        3/23/2021Listed for sale$236,000+57.3%$126/sqft
        Source: Stellar MLS #G5039124 Report a problem
        2/9/2019Listing removed$1,250$1/sqft
        Source: Noelco Inc DBA Orlando Homes and Investments Report a problem
        2/6/2019Listed for rent$1,250+4.3%$1/sqft
        Source: Noelco Inc DBA Orlando Homes and Investments Report a problem
        10/10/2014Listing removed$1,199$1/sqft
        Source: ORLANDO HOMES AND INVESTMENTS (287) #G4803684 Report a problem
        9/20/2014Listed for rent$1,199$1/sqft
        Source: Orlando Homes and Investments Report a problem
        9/12/2014Sold$149,990$80/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$3,643 +2.5%$258,710 +2.9%
        2024$3,555 +4.4%$251,420 +3%
        2023$3,406 +0.3%$244,100 +3%
        2022$3,397 +4.9%$236,996 +26.1%
        2021$3,237 -2.5%$187,970 +6.3%
        2020$3,322 +10.5%$176,789 +10%
        2019$3,006 +8.4%$160,717 +6.9%
        2018$2,773 $150,303 +9.1%
        2017$2,773 +8.4%$137,821
        2016$2,557 -1.5%$137,821 +4.2%
        2015$2,597 +8.3%$132,318 +1.8%
        2014$2,399 +974.2%$130,041 +970.3%
        2013$223 -0.8%$12,150
        2012$225 +0.1%$12,150
        2011$225 +21.6%$12,150
        2010$185 +0.1%$12,150
        2009$185 -39.9%$12,150 -40%
        2008$308 -44.6%$20,250 -44.4%
        2007$555 -7.3%$36,450
        2006$599 $36,450
        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.
        Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: 34748

        Getting around

        2 / 100
        Car-Dependent
        23 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Leesburg Elementary
        • Middle: Oak Park Middle
        • High: Leesburg High

        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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