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Sold for $680,000
    • $680,000

    1742 Chestnut Ave, Winter Park, FL 32789

    4beds
    1,729sqft
    Single Family Residence
    Built in 1957
    9,437 Square Feet Lot
    $747,400 Zestimate®
    $393/sqft
    $3,348 Estimated rent

    Home value

    $747,400

    $703,000 - $800,000

    $3,348/mo

    Zestimate® history
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    What's special

    Welcome to this charming retreat in one of Winter Park’s most desirable neighborhoods! Only minutes from Park Avenue, this home sits on a large lot along the beautiful and infamous “Tree Streets.” This updated pool home offers 4 bedrooms plus a bonus guest room, perfect for visitors or an office. Step inside and be greeted by the warm terracotta and wood floors that create a cozy and inviting atmosphere. The kitchen is a chef’s delight, complete with Frank Lloyd Wright style cabinets, stone countertops, and stainless steel backsplash. This home features a BRAND NEW ROOF and A/C system, newer appliances, and a fresh coat of interior paint throughout. The heart of this home is undoubtedly the stunning pool area, a private and spacious retreat that offers relaxation in the Florida sun. The location of this property is unparalleled, just minutes from Phelps Park, Winter Park Racquet Club, YMCA, Winter Park Hospital and medical center, lavish shopping and some of Central Florida’s best restaurants.

    Zillow last checked:

    Listing updated:

    Listed by:

    Brinley Donovan 321-704-5791,

    ACME REAL ESTATE FLORIDA LLC 407-601-4958

    Bought with:

    Blaike Gill, 3495240

    KELLER WILLIAMS WINTER PARK

    Source: Stellar MLS,MLS#: O6156499MLS LogoOriginating MLS: Orlando Regional

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 4
    • Bathrooms: 2
    • Full bathrooms: 2
    Primary bedroom
    • Level: First
    • Dimensions: 14x11
    Kitchen
    • Level: First
    • Dimensions: 11x10
    Living room
    • Level: First
    • Dimensions: 12x16
    Heating
    • Central
    Cooling
    • Central Air
    Appliances
    • Included: Convection Oven, Dishwasher, Electric Water Heater, Microwave, Refrigerator
    Features
    • Other, Solid Wood Cabinets, Stone Counters
    • Flooring: Tile, Hardwood
    • Has fireplace: No
    Interior area
    • Total structure area: 2,241
    • Total interior livable area: 1,729 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage - Attached
    • Attached garage spaces: 2
    Features
    • Levels: One
    • Stories: 1
    • Exterior features: Irrigation System, Storage
    • Has private pool: Yes
    • Pool features: Child Safety Fence, In Ground
    Lot
    • Size: 9,437 Square Feet
    Details
    • Parcel number: 322130170802050
    • Zoning: R-1A
    • 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: 1957

    Utilities & green energy

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

    Community & HOA

    Community
    • Pet fee: $0 monthly
    • Subdivision: CONWILL ESTATES
    HOA
    • Has HOA: No
    Location
    • Region: Winter Park

    Financial & listing details

    • Price per square foot: $393/sqft
    • Tax assessed value: $513,275
    • Annual tax amount: $5,811
    • Date on market: 11/10/2023
    • Cumulative days on market: 70 days
    • Listing terms: Cash,Conventional,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Road surface type: Asphalt

    Price history

    DateEventPrice
    4/23/2024Listing removed--
    Source: Stellar MLS #O6187438 Report a problem
    3/29/2024Price change$4,699-5.9%$3/sqft
    Source: Stellar MLS #O6187438 Report a problem
    3/15/2024Listed for rent$4,995$3/sqft
    Source: Stellar MLS #O6187438 Report a problem
    1/30/2024Sold$680,000-1.3%$393/sqft
    Source: Stellar MLS #O6156499 Report a problem
    1/19/2024Pending sale$689,000$398/sqft
    Source: Stellar MLS #O6156499 Report a problem
    1/12/2024Price change$689,000-4.2%$398/sqft
    Source: Stellar MLS #O6156499 Report a problem
    1/2/2024Price change$719,000-4%$416/sqft
    Source: Stellar MLS #O6156499 Report a problem
    12/13/2023Price change$749,000-2%$433/sqft
    Source: Stellar MLS #O6156499 Report a problem
    11/25/2023Price change$764,000-3.2%$442/sqft
    Source: Stellar MLS #O6156499 Report a problem
    11/10/2023Listed for sale$789,000+79.7%$456/sqft
    Source: Stellar MLS #O6156499 Report a problem
    6/1/2020Sold$439,000-0.2%$254/sqft
    Source: Public Record Report a problem
    4/28/2020Pending sale$439,900$254/sqft
    Source: PARKSIDE PROPERTIES, LLC #O5856944 Report a problem
    4/10/2020Listed for sale$439,900+16.4%$254/sqft
    Source: PARKSIDE PROPERTIES, LLC #O5856944 Report a problem
    4/8/2016Listing removed$378,000$219/sqft
    Source: Owner Report a problem
    4/8/2016Listed for sale$378,000+5%$219/sqft
    Source: Owner Report a problem
    4/5/2016Sold$360,000-4.8%$208/sqft
    Source: Public Record Report a problem
    2/26/2016Pending sale$378,000$219/sqft
    Source: Owner Report a problem
    12/30/2015Price change$378,000+0.5%$219/sqft
    Source: Owner Report a problem
    8/23/2015Price change$376,000-5.3%$217/sqft
    Source: Owner Report a problem
    7/20/2015Listed for sale$397,000+213.8%$230/sqft
    Source: Owner Report a problem
    12/30/1996Sold$126,500+10%$73/sqft
    Source: Public Record Report a problem
    6/12/1995Sold$115,000$67/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$6,478 +4%$440,937 +3%
    2023$6,226 +7.2%$428,094 +3%
    2022$5,811 +1.2%$415,625 +3%
    2021$5,744 +15.8%$403,519 +15.8%
    2020$4,960 +0.8%$348,499 +2.3%
    2019$4,920 +0.6%$340,664 +1.9%
    2018$4,890 $334,312 +2.1%
    2017$4,890 +1%$327,436 +2%
    2016$4,843 +89.2%$320,863 +7.7%
    2015$2,560 -3.1%$297,947 +28.4%
    2014$2,642 +2.5%$231,999 +10.2%
    2013$2,578 +1.3%$210,506 +11.1%
    2012$2,545 +3.4%$189,500 -9.3%
    2011$2,461 +5.6%$208,967 -12.4%
    2010$2,330 $238,620 -18.6%
    2009-- $293,214 -17.3%
    2008$2,135 -5.9%$354,356 -9.9%
    2007$2,271 -6.3%$393,305 +31.2%
    2006$2,423 +0.3%$299,801 +21.4%
    2005$2,417 +4.8%$247,037 +25%
    2004$2,305 +5.8%$197,681 +0.5%
    2003$2,178 +3%$196,682 +16.1%
    2002$2,116 +0.6%$169,474 +12.2%
    2001$2,103 +22.2%$151,109 +18.7%
    2000$1,721 $127,272
    Find assessor info on the county website

    Neighborhood: 32789

    Nearby homes

    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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    Estimated market value
    $747,400
    Get a cash offer in 3 minutes
    Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
    Estimated market value
    $747,400

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