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For sale
  • $985,000

    1611 CHESTNUT AVENUE, WINTER PARK, FL 32789

    4beds
    2,916sqft
    : 
    $6,919/mo
    Get pre-qualified
    Single Family Residence
    Built in 1973
    7,508 Square Feet Lot
    $-- Zestimate®
    $338/sqft
    $-- HOA

    What's special

    Generous islandBeautifully redesigned kitchenQuartz countertopsAttached two-car garageDedicated built-in office alcoveCustom built-insSeparate expansive family room
    Located on one of Winter Park's beautiful oak-lined brick streets, 1611 Chestnut Avenue is an extensively renovated and expanded 4-bedroom, 4-bath residence offering nearly 3,000 square feet of thoughtfully designed living space in the highly desirable 32789 ZIP code. Far beyond cosmetic updates, this home has undergone a substantial transformation, including major additions to the rear and second floor, creating a spacious, versatile layout with high-quality finishes and modern comforts throughout. The result is a home that combines the established character of its surroundings with the space and functionality of a contemporary residence. The beautifully redesigned kitchen features quartz countertops, stainless steel appliances, a generous island, farmhouse sink, and adjoining pantry, opening to inviting living and dining areas. Whether preparing a quiet dinner or hosting a gathering, the kitchen's generous workspace and connection to the surrounding rooms make it a natural center of daily life. A separate, expansive family room showcases a stone wood-burning fireplace and custom built-ins, providing another comfortable setting for relaxing or entertaining. Engineered hardwood and luxury vinyl flooring, designer tilework, upgraded fixtures, and beautifully appointed bathrooms reflect the attention and investment devoted to this home. The thoughtful separation of living spaces gives everyone room to enjoy the home in their own way without sacrificing the ease of gathering together. The impressive upstairs primary retreat provides exceptional privacy, featuring a spacious en-suite bathroom with freestanding soaking tub, double vanity, walk-in closet, and dedicated built-in office alcove. Occupying its own upper-level space, this generously proportioned suite feels like a retreat within the home, with room for both a restful bedroom setting and a practical workspace. Three additional bedrooms are located downstairs, including two with en-suite bathrooms. One enjoys an adjoining sitting room with sliding doors opening to the backyard, creating an ideal arrangement for extended family, guests, or multigenerational living. This flexible layout is equally appealing for those seeking a private guest area, a home office, or separate spaces for different daily routines. Additional improvements include an updated roof, newer AC system, a dedicated laundry room, attached two-car garage, and a private fenced backyard surrounded by mature landscaping. The outdoor setting provides space to unwind, enjoy fresh air, or create a welcoming area for casual get-togethers, while the mature trees and greenery reinforce the charm of this established neighborhood. Situated in Winter Park's established Lake Knowles Terrace neighborhood, the property is surrounded by charming residences, beautifully renovated homes, and impressive newer custom construction. Here, brick-paved streets and a canopy of mature oaks create a distinctive streetscape that is increasingly difficult to find. Enjoy convenient access to the Winter Park Chain of Lakes, Winter Park Golf Course, Phelps Park, the YMCA, and the renowned shopping, dining, and cultural attractions of Park Avenue. From neighborhood walks beneath the oaks to an afternoon along Park Avenue, this address places many of Winter Park's most loved destinations close to home. An exceptional combination of extensive improvements, generous living space, flexible accommodations, and a highly sought-after Winter Park location.
    1 day
    642
    37

    Zillow last checked:

    Listing updated:

    Listed by:

    Gunel Aydamirli 407-907-7704,

    OLYMPUS EXECUTIVE REALTY INC 407-469-0090

    Source: Stellar MLS,MLS#: O6449003MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Primary bedroom
      • Features: En Suite Bathroom, Walk-In Closet(s)
      • Level: Second
      • Area: 528 Square Feet
      • Dimensions: 22x24
      Bedroom 2
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 12x14
      Bedroom 3
      • Features: En Suite Bathroom, Built-in Closet
      • Level: First
      • Area: 154 Square Feet
      • Dimensions: 14x11
      Bedroom 4
      • Features: Built-in Closet
      • Level: First
      • Area: 121 Square Feet
      • Dimensions: 11x11
      Bonus room
      • Features: No Closet
      • Level: First
      • Area: 108 Square Feet
      • Dimensions: 12x9
      Dining room
      • Features: Pantry
      • Level: First
      • Area: 132 Square Feet
      • Dimensions: 11x12
      Family room
      • Level: First
      • Area: 340 Square Feet
      • Dimensions: 17x20
      Foyer
      • Features: Built-In Shelving
      • Level: First
      • Area: 54 Square Feet
      • Dimensions: 9x6
      Kitchen
      • Features: Pantry
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 21x8
      Laundry
      • Features: Built-In Shelving, Sink - Pedestal
      • Level: First
      • Area: 135 Square Feet
      • Dimensions: 9x15
      Living room
      • Level: First
      • Area: 168 Square Feet
      • Dimensions: 14x12
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Disposal, Dryer, Electric Cooktop, Electric Water Heater, Range, Range Hood, Refrigerator, Washer
      • Laundry: Electric Dryer Hookup, Inside, Laundry Room, Sink, Washer Hookup
      Features
      • Carbon Mono/Detector, Ceiling Fan(s), Crown Molding, High Ceilings, PrimaryBedroom Upstairs, Solid Surface Counters, Solid Wood Cabinets, Stone Counters, Thermostat, Walk-In Closet(s)
      • Flooring: Ceramic Tile, Engineered Hardwood, Luxury Vinyl
      • Doors: Sliding Doors, Sliding Doors
      • Has fireplace: Yes
      • Fireplace features: Family Room, Stone
      Interior area
      • Total structure area: 3,530
      • Total interior livable area: 2,916 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Driveway, Ground Level, Off Street, Oversized
      • Has attached garage: Yes
      • Has uncovered spaces: Yes
      • Details: Garage Dimensions: 22X20
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Patio
      • Exterior features: Courtyard, Private Yard, Rain Gutters, Sidewalk, Sprinkler Metered, Storage
      • Fencing: Fenced,Wood
      Lot
      • Size: 7,508 Square Feet
      • Features: City Lot, Landscaped, Level, Near Golf Course, Near Public Transit, Sidewalk
      • Residential vegetation: Mature Landscaping, Oak Trees
      Details
      • Additional structures: Shed(s)
      • Parcel number: 322130453601100
      • Zoning: WP-R-1A
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Contemporary,Custom
      • 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: Cable Connected, Electricity Connected, Fiber Optics, Public, Sewer Connected, Sprinkler Meter, Street Lights, Underground Utilities, Water Connected

      Community & HOA

      Community
      • Security: Smoke Detector(s)
      • Pet fee: $0 monthly
      • Subdivision: LAKE KNOWLES TERRACE
      HOA
      • Has HOA: No
      Location
      • Region: Winter Park

      Financial & listing details

      • Price per square foot: $338/sqft
      • Tax assessed value: $747,448
      • Annual tax amount: $3,697
      • Date on market: 10/13/2026
      • Cumulative days on market: 147 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Brick

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        10/14/2026Listed for sale$985,000-1%$338/sqft
        Source: Stellar MLS #O6449003 Report a problem
        9/22/2026Listing removed$995,000$341/sqft
        Source: Stellar MLS #O6402502 Report a problem
        8/4/2026Price change$995,000-4.3%$341/sqft
        Source: Stellar MLS #O6402502 Report a problem
        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.
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        Climate risks

        Neighborhood: 32789

        Getting around

        13 / 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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