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For sale
    • $535,000

    5106 Chanticleer Dr, Leesburg, FL 34748

    3beds
    3,112sqft
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    Single Family Residence
    Built in 2006
    10,500 Square Feet Lot
    $514,500 Zestimate®
    $172/sqft
    $180/mo HOA

    What's special

    Abundant natural lightBeautiful french doorsOversized living spacesSoaring ceilingsElegant archwaysGenerous counter spaceUpgraded appliances
    Welcome to 5106 Chanticleer Dr, a rare and extensively expanded custom home located in the highly sought-after Plantation at Leesburg, one of Central Florida’s premier 55+ gated golf communities. Offering 3 bedrooms, 2.5 baths, a versatile flex room, and an impressive 3,112 square feet of living space, this thoughtfully designed residence combines spacious living, quality upgrades, and exceptional functionality rarely found in the community. From the moment you enter, you’ll appreciate the soaring ceilings, elegant archways, abundant natural light, and oversized living spaces that create an open yet inviting feel throughout the home. The expansive layout offers multiple entertaining and gathering areas, while the split-bedroom floor plan provides privacy and flexibility for guests or multigenerational living. The flex room is ideal for a home office, hobby space, library, or additional guest accommodations. The kitchen is both spacious and functional, featuring upgraded appliances, abundant cabinetry, generous counter space, and a large center island perfect for cooking and entertaining. The adjacent living areas flow seamlessly to the oversized rear porch through beautiful French doors, creating the ideal indoor-outdoor Florida lifestyle. Extensive structural upgrades set this home apart, including a garage expansion with an additional 6’ on the right side and 4’ to the front, a 4’ bedroom extension, a fully enclosed 16’x10’ room off the left-side patio with windows, and a massive 30’x10’ rear porch ideal for relaxing or entertaining. Additional custom storage spaces include a 10’x10’ closet with window in the flex room and another 12’x10’ closet in the rear guest room. The primary suite features upgraded luxury vinyl plank flooring and its own dedicated HVAC system for enhanced comfort and efficiency. Major mechanical updates include a new roof (2021), HVAC system (2021), and hot water heater (2020). The home also features an upgraded oversized gutter and downspout system engineered to meet FBC2001 wind load standards for added durability and peace of mind. Residents of Plantation at Leesburg enjoy resort-style amenities including two 18-hole championship golf courses, three clubhouses, three heated pools, fitness centers, tennis and pickleball courts, walking trails, fishing lakes, an on-site restaurant, and countless clubs and social activities. Conveniently located near shopping, dining, medical facilities, and the Florida Turnpike, this one-of-a-kind property offers the perfect blend of comfort, flexibility, and active Florida living.
    59 days
    |
    132
    |
    7
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Mary Jane Grimes 410-353-0795,

    CENTURY 21 MYERS ROSE REALTY 352-717-2000

    Source: Stellar MLS,MLS#: G5112349MLS LogoOriginating MLS: Lake and Sumter

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 3
      • Bathrooms: 3
      • Full bathrooms: 2
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Breakfast Room Separate, Family Room, Dining Room, Living Room, Great Room, Utility Room
      Primary bedroom
      • Features: En Suite Bathroom, Garden Bath, Split Vanities, Tub with Separate Shower Stall, Water Closet/Priv Toilet, Walk-In Closet(s)
      • Level: First
      • Area: 378 Square Feet
      • Dimensions: 21x18
      Bedroom 2
      • Features: No Closet
      • Level: First
      • Area: 165 Square Feet
      • Dimensions: 11x15
      Bedroom 3
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 162 Square Feet
      • Dimensions: 9x18
      Bathroom 1
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 270 Square Feet
      • Dimensions: 18x15
      Balcony porch lanai
      • Level: First
      • Area: 290 Square Feet
      • Dimensions: 29x10
      Den
      • Features: Built-in Closet
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Dinette
      • Level: First
      • Area: 195 Square Feet
      • Dimensions: 15x13
      Dining room
      • Features: Wet Bar
      • Level: First
      • Area: 150 Square Feet
      • Dimensions: 10x15
      Family room
      • Level: First
      • Area: 323 Square Feet
      • Dimensions: 19x17
      Kitchen
      • Features: Pantry, Kitchen Island
      • Level: First
      • Area: 210 Square Feet
      • Dimensions: 14x15
      Laundry
      • Level: First
      • Area: 45 Square Feet
      • Dimensions: 9x5
      Living room
      • Level: First
      • Area: 285 Square Feet
      • Dimensions: 19x15
      Heating
      • Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Ice Maker, Microwave, Range, Refrigerator, Washer
      • Laundry: Electric Dryer Hookup, Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Eating Space In Kitchen, Kitchen/Family Room Combo, Open Floorplan, Primary Bedroom Main Floor, Split Bedroom, Walk-In Closet(s), Wet Bar
      • Flooring: Carpet, Luxury Vinyl, Tile
      • Doors: French Doors
      • Windows: Blinds, Window Treatments
      • Has fireplace: No
      Interior area
      • Total structure area: 4,326
      • Total interior livable area: 3,112 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 3
      • Parking features: Garage Door Opener, Off Street
      • Attached garage spaces: 3
      • Details: Garage Dimensions: 26X24
      Features
      • Levels: One
      • Stories: 1
      • Patio & porch: Covered, Enclosed, Rear Porch, Screened
      • Exterior features: Irrigation System
      • Waterfront features: Fishing Pier
      Lot
      • Size: 10,500 Square Feet
      • Residential vegetation: Mature Landscaping
      Details
      • Parcel number: 252024022900002700
      • Zoning: PUD
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 2006

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Cable Available, Electricity Connected, Public

      Community & HOA

      Community
      • Features: Fishing, Association Recreation - Owned, Buyer Approval Required, Clubhouse, Community Mailbox, Deed Restrictions, Fitness Center, Gated Community - Guard, Golf Carts OK, Golf, Pool, Restaurant, Sidewalks, Special Community Restrictions, Tennis Court(s), Wheelchair Access
      • Security: Gated Community, Smoke Detector(s)
      • Pet fee: $0 monthly
      • Senior community: Yes
      • Subdivision: PLANTATION AT LEESBURG CHANTICLEER VILLAGE L
      HOA
      • Has HOA: Yes
      • Amenities included: Basketball Court, Elevator(s), Fence Restrictions, Fitness Center, Gated, Golf Course, Optional Additional Fees, Pickleball Court(s), Pool, Recreation Facilities, Sauna, Security, Shuffleboard Court, Spa/Hot Tub, Storage, Tennis Court(s), Trail(s), Vehicle Restrictions, Wheelchair Access
      • Services included: 24-Hour Guard, Common Area Taxes, Community Pool, Reserve Fund, Manager, Pool Maintenance, Private Road, Recreational Facilities, Security
      • HOA fee: $180 monthly
      • HOA name: HOA Office
      Location
      • Region: Leesburg

      Financial & listing details

      • Price per square foot: $172/sqft
      • Tax assessed value: $370,366
      • Annual tax amount: $4,549
      • Date on market: 5/18/2026
      • Cumulative days on market: 60 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

        $514,500

        $489,000 - $540,000

        $2,611/mo

        Price history

        DateEventPrice
        5/18/2026Listed for sale$535,000$172/sqft
        Source: Stellar MLS #G5112349 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$4,549 +2.4%$319,130 +2.9%
        2024$4,444 +8.4%$310,140 +3%
        2023$4,098 +4.8%$301,110 +3%
        2022$3,909 +3.7%$292,340 +3%
        2021$3,769 -4.7%$283,828 +1.4%
        2020$3,955 +0.6%$279,910 +2.3%
        2019$3,930 +4.4%$273,617 +1.9%
        2018$3,765 $268,516 -2.9%
        2017$3,765 -2.6%$276,416
        2016$3,864 -14.6%$276,416 +3.8%
        2015$4,522 +0.9%$266,325 +1.8%
        2014$4,482 +17.8%$261,697 +2.4%
        2013$3,805 -1%$255,680
        2012$3,844 -5.8%$255,680 -5.9%
        2011$4,079 -4.8%$271,697 -3.5%
        2010$4,285 -0.6%$281,416 -0.8%
        2009$4,312 -6.5%$283,572 -6.6%
        2008$4,613 -15%$303,635 -14.7%
        2007$5,425 $356,147
        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.
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        Climate risks

        Neighborhood: 34748

        Getting around

        1 / 100
        Car-Dependent
        21 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

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