Skip main navigation
Under contract
  • $674,900

    111 Chestnut Glen Dr, Louisville, KY 40245

    7beds
    4,457sqft
    : 
    $4,473/mo
    Get pre-qualified
    Single Family Residence
    Built in 2002
    0.35 Acres Lot
    $656,300 Zestimate®
    $151/sqft
    $48/mo HOA

    What's special

    Impressive custom walk-in closetElegant millworkSix-burner gas cooktopLarge recreation roomBeautiful stone fireplaceInviting front porchManicured landscaping
    OPEN HOUSE 8/9/26 12-2PM. Welcome to 111 Chestnut Glen Drive, a 7 bedroom, 3.5 bath estate offering nearly 4,500 finished square feet in one of East Louisville's most sought-after neighborhoods. Thoughtfully designed for both everyday living and exceptional entertaining, this home blends timeless architecture with generous living spaces throughout. A stately stone exterior, manicured landscaping, and inviting front porch lead to a dramatic foyer with hardwood flooring, elegant millwork, and a formal dining room. The two-story great room features soaring vaulted ceilings and a wall of windows overlooking the private, wooded backyard. The chef's kitchen is equipped with custom cabinetry, stainless steel appliances, a six-burner gas cooktop, and an oversized center island, while the cozy, adjoining hearth room offers a beautiful stone fireplace for more intimate gatherings. The spacious first-floor primary suite is a true retreat with triple tray ceilings, backyard views, a luxurious ensuite bath with a jacuzzi tub, frameless walk-in shower, dual vanities, and an impressive custom walk-in closet. Upstairs are four generously-sized bedrooms, including vaulted ceilings, Palladian windows, sitting areas, and charming Juliet balconies overlooking the great room. The finished walkout basement provides incredible flexibility with a large recreation room, kitchenette, dining area, custom built-in library shelving, two additional bedrooms, and a 3rd full bathroom, making it ideal for guests, multigenerational living, or extended entertaining. Meanwhile, the unfinished section adds abundant storage solutions, as well as possible workout area (or, alternatively, it's current setup: a golf simulator!). Outside, multiple levels of decking overlook beautifully landscaped, grounds where winding stone pathways lead through mature trees to a secluded stone patio with a brick fire pit, creating an unforgettable setting for relaxing or entertaining. Meanwhile, the outdoor sprinkler system makes lawn maintenance a breeze! An attached two-car garage—featuring a Tesla charger!—completes this exceptional property. Chestnut Glen's central location means your family retains the convenience of nearby access to ample shopping, dining, and entertainment options (a new Publix just opened within walking distance!), while still retaining safety and security of a quiet, low-traffic, Mayberry-like community. Rarely does a home offer this combination of space, craftsmanship, privacy, and convenience. Experience one of East Louisville's finest opportunities at 111 Chestnut Glen Drive.
    16 days
    |
    1,551
    |
    98
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Eric Scroggin 502-262-5475,

    RE/MAX Results

    Source: Metro Search Inc. LLC DBA Apex MLS,MLS#: 1725607MLS Logo

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 7
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Primary bedroom
      • Level: First
      Bedroom
      • Level: Second
      Bedroom
      • Level: Second
      Bedroom
      • Level: Second
      Bedroom
      • Level: Basement
      Bedroom
      • Level: Basement
      Primary bathroom
      • Level: First
      Half bathroom
      • Level: First
      Full bathroom
      • Level: Second
      Full bathroom
      • Level: Basement
      Dining room
      • Description: Formal
      • Level: First
      Family room
      • Level: First
      Foyer
      • Level: First
      Great room
      • Level: First
      Great room
      • Level: Basement
      Kitchen
      • Description: Eat in Kitchen
      • Level: First
      Laundry
      • Level: First
      Other
      • Level: Basement
      Other
      • Level: Basement
      Heating
      • Natural Gas
      Cooling
      • Central Air
      Features
      • Basement: Walkout Finished
      • Number of fireplaces: 1
      Interior area
      • Total structure area: 3,132
      • Total interior livable area: 4,457 sqft
      • Finished area above ground: 3,132
      • Finished area below ground: 1,325
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached, Entry Side, Driveway
      • Attached garage spaces: 2
      • Has uncovered spaces: Yes
      Features
      • Stories: 2
      • Patio & porch: Deck, Patio
      • Fencing: Other,Full
      Lot
      • Size: 0.35 Acres
      • Features: Sidewalk, See Remarks
      Details
      • Parcel number: 00000

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Traditional
      • Property subtype: Single Family Residence
      Materials
      • Brick Veneer, Stone
      • Foundation: Concrete Perimeter
      • Roof: Shingle
      Condition
      • Year built: 2002

      Utilities & green energy

      • Sewer: Public Sewer
      • Water: Public
      • Utilities for property: Electricity Connected, Natural Gas Connected

      Community & HOA

      Community
      • Subdivision: Chestnut Glen
      HOA
      • Has HOA: Yes
      • HOA fee: $575 annually
      Location
      • Region: Louisville

      Financial & listing details

      • Price per square foot: $151/sqft
      • Tax assessed value: $476,810
      • Annual tax amount: $5,321
      • Date on market: 8/6/2026
      • Electric utility on property: Yes

        Estimated market value

        $656,300

        $623,000 - $689,000

        $4,101/mo

        Price history

        DateEventPrice
        8/11/2026Contingent$674,900$151/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1725607 Report a problem
        8/6/2026Listed for sale$674,900+42.7%$151/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1725607 Report a problem
        10/31/2019Sold$472,900$106/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1543160 Report a problem
        9/16/2019Listing removed$3,250$1/sqft
        Source: Metro Realty #1541884 Report a problem
        9/4/2019Listed for rent$3,250$1/sqft
        Source: Metro Realty #1541884 Report a problem
        8/24/2019Price change$472,900-0.4%$106/sqft
        Source: Metro Realty #1535858 Report a problem
        7/18/2019Price change$474,900-1%$107/sqft
        Source: Metro Realty #1535858 Report a problem
        6/25/2019Price change$479,900+0.2%$108/sqft
        Source: Metro Realty #1535858 Report a problem
        6/2/2019Price change$478,900-1.6%$107/sqft
        Source: Mink Realty #1532473 Report a problem
        5/18/2019Listed for sale$486,625+4.4%$109/sqft
        Source: Mink Realty #1532473 Report a problem
        9/28/2018Sold$465,900+1.7%$105/sqft
        Source: Metro Search Inc. LLC DBA Apex MLS #1511519 Report a problem
        8/22/2018Pending sale$457,900$103/sqft
        Source: Schuler Bauer Real Estate ERA Powered #1511519 Report a problem
        8/10/2018Listed for sale$457,900+14.8%$103/sqft
        Source: Schuler Bauer Real Estate Services ERA Powered #1511519 Report a problem
        11/4/2013Sold$399,000+6.4%$90/sqft
        Source: Public Record Report a problem
        11/9/2009Sold$375,000+5.3%$84/sqft
        Source: Public Record Report a problem
        9/23/2002Sold$356,241+409.6%$80/sqft
        Source: Public Record Report a problem
        4/22/2002Sold$69,900+16.5%$16/sqft
        Source: Public Record Report a problem
        2/8/2002Sold$60,000$13/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$5,321 -1.9%$476,810
        2024$5,426 -1.7%$476,810
        2023$5,521 -0.3%$476,810
        2022$5,541 -6.6%$476,810 +0.8%
        2021$5,934 +8.9%$472,900
        2020$5,448 $472,900 +1.5%
        2019$5,448 +28.5%$465,900 +17.6%
        2018$4,241 $396,160
        2017$4,241 +13.1%$396,160 +5.6%
        2013$3,750 $375,000
        2011$3,750 $375,000
        2010$3,750 +5.3%$375,000 +5.3%
        2009$3,562 $356,240
        2007-- $356,240
        2006-- $356,240
        2005-- $356,240
        2004-- $356,240
        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.
        See how much you could borrow to make a competitive offer.

        Climate risks

        Neighborhood: Eastwood

        Getting around

        13 / 100
        Car-Dependent
        2 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating

        A local agent can set up tours, give advice and negotiate with sellers.

        Browse local experts

        Similar homes