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For sale
    • Price cut: $30K (7/10)
    $1,040,000

    1611 Chestnut Ave, Winter Park, FL 32789

    4beds
    2,916sqft
    : 
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    Single Family Residence
    Built in 1973
    7,508 Square Feet Lot
    $998,700 Zestimate®
    $357/sqft
    $-- HOA

    What's special

    Home officeQuartz countertopsDesigner tileCustom tile workWelcoming fireplaceLush mature landscapingNumerous built ins
    NEW PRICE!! DON'T MISS THIS OPPORTUNITY! Situated on arguably the finest brick street in Winter Park, beneath a canopy of live oaks, this fully renovated 4-bedroom, 4-bath home delivers the rarest combination: the soul of an established neighborhood, unique charm and character, and the bones of new construction. Gutted to the studs and rebuilt with intention, every major system is new — electrical, Carrier ACs, roof, ductwork, drywall, Pella windows +++. With elevated finishes, like designer tile and quartz countertops as well as floors and beautifully reimagined kitchen and baths. A second-floor addition adds a sprawling 21 x 24 foot private primary suite and home office, one of the many reasons this an ideal setup for MULTIGENERATIONAL families and those who work from home. A welcoming fireplace, lush mature landscaping, butler's pantry, numerous built ins, custom tile work, and an address minutes from Park Avenue make this one of Winter Park's most compelling offerings. Come imagine the possibilities.
    77 days
    |
    1,573
    |
    55
    |

    Likely to sell faster than

    Zillow last checked:

    Listing updated:

    Listed by:

    Olivia Maxwell 407-222-4440,

    FANNIE HILLMAN & ASSOCIATES 407-644-1234,

    Julia Dalessandro 407-486-9651,

    FANNIE HILLMAN & ASSOCIATES

    Source: Stellar MLS,MLS#: O6402502MLS LogoOriginating MLS: Orlando Regional

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Primary bedroom
      • Features: Built-in Features, Walk-In Closet(s)
      • Level: Second
      • Area: 504 Square Feet
      • Dimensions: 21x24
      Bedroom 1
      • Features: Walk-In Closet(s)
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Kitchen
      • Features: Kitchen Island
      • Level: First
      • Area: 216 Square Feet
      • Dimensions: 18x12
      Living room
      • Features: Built-In Shelving
      • Level: First
      • Area: 336 Square Feet
      • Dimensions: 16x21
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Range, Refrigerator
      • Laundry: Laundry Room
      Features
      • Ceiling Fan(s), Solid Surface Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Ceramic Tile, Engineered Hardwood, Luxury Vinyl
      • Has fireplace: Yes
      • Fireplace features: Family Room, Stone
      Interior area
      • Total structure area: 3,316
      • Total interior livable area: 2,916 sqft
      Video & virtual tour

      Property

      Parking
      • Total spaces: 2
      • Parking features: Garage - Attached
      • Attached garage spaces: 2
      Features
      • Levels: Two
      • Stories: 2
      • Exterior features: Sidewalk, Sprinkler Metered
      Lot
      • Size: 7,508 Square Feet
      Details
      • Parcel number: 322130453601100
      • Zoning: R-1A
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Block, Stucco, Wood Frame
      • Foundation: Slab
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1973

      Utilities & green energy

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

      Community & HOA

      Community
      • Pet fee: $0 monthly
      • Subdivision: LAKE KNOWLES TERRACE
      HOA
      • Has HOA: No
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $357/sqft
      • Tax assessed value: $747,448
      • Annual tax amount: $3,589
      • Date on market: 4/30/2026
      • Cumulative days on market: 78 days
      • Listing terms: Cash,Conventional
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Brick

        Estimated market value

        $998,700

        $949,000 - $1.05M

        $5,771/mo

        Price history

        DateEventPrice
        7/10/2026Price change$1,040,000-2.8%$357/sqft
        Source: Stellar MLS #O6402502 Report a problem
        6/10/2026Price change$1,070,000-2.7%$367/sqft
        Source: Stellar MLS #O6402502 Report a problem
        4/30/2026Listed for sale$1,100,000-7.9%$377/sqft
        Source: Stellar MLS #O6402502 Report a problem
        8/15/2025Listing removed$1,195,000$410/sqft
        Source: Stellar MLS #O6281275 Report a problem
        7/3/2025Price change$1,195,000-7.7%$410/sqft
        Source: Stellar MLS #O6281275 Report a problem
        2/15/2025Listed for sale$1,295,000+4.4%$444/sqft
        Source: Stellar MLS #O6281275 Report a problem
        10/18/2023Listing removed--
        Source: Stellar MLS #O6133987 Report a problem
        8/14/2023Listed for sale$1,240,000+188.4%$425/sqft
        Source: Stellar MLS #O6133987 Report a problem
        5/22/2017Listing removed$429,900$147/sqft
        Source: RE/MAX 200 REALTY #O5470306 Report a problem
        10/12/2016Listed for sale$429,900+343.2%$147/sqft
        Source: RE/MAX 200 REALTY #O5470306 Report a problem
        11/26/1991Sold$97,000$33/sqft
        Source: Agent Provided Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$3,456 +4.6%$247,761 +3%
        2023$3,303 +92.2%$240,545 +59.5%
        2022$1,719 +1.8%$150,785 +3%
        2021$1,689 +0.2%$146,393 +1.4%
        2020$1,685 +1.2%$144,372 +2.3%
        2019$1,665 +1%$141,126 +1.9%
        2018$1,648 $138,495 -58.9%
        2017$1,648 +1.5%$337,079 +2.7%
        2016$1,624 +2.3%$328,178 +11.2%
        2015$1,587 -3%$295,210 +24.4%
        2014$1,637 +2.8%$237,242 +16.5%
        2013$1,593 +1.6%$203,698 +9.6%
        2012$1,568 +3.9%$185,892 -1.1%
        2011$1,510 +6.2%$188,002 -10.7%
        2010$1,422 $210,516 -17.9%
        2009-- $256,505 -14.2%
        2008$1,293 -64%$299,019 -13.9%
        2007$3,590 +8.1%$347,345 +23.5%
        2006$3,322 +5.7%$281,219 +10.8%
        2005$3,142 +26.3%$253,884 +33.5%
        2004$2,487 +5.2%$190,243 +1.1%
        2003$2,363 +12.3%$188,103 +16.1%
        2002$2,105 +37.2%$161,999 +31.9%
        2001$1,534 +3.3%$122,812 +3.4%
        2000$1,485 $118,781
        Find assessor info on the county website

        Monthly payment

        Est. payment

        Payment breakdown

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        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: 32789

        Getting around

        14 / 100
        Car-Dependent
        0 / 100
        No Nearby Transit
        37 / 100
        Somewhat Bikeable

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • Elementary: Lakemont Elem
        • Middle: Maitland Middle
        • High: Winter Park 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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