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Sold for $2,200,000
  • $2,200,000

    1340 Chestnut Ave, Winter Park, FL 32789

    6beds
    4,182sqft
    Single Family Residence
    Built in 1963
    0.25 Acres Lot
    $2,266,200 Zestimate®
    $526/sqft
    $6,611 Estimated rent

    Home value

    $2,266,200

    $2.06M - $2.52M

    $6,611/mo

    Zestimate® history
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    What's special

    Welcome to this stunning contemporary home on a brick-lined, tree street in the heart of Winter Park. Boasting a seamless blend of timeless charm and modern luxury, this 1963 home was fully remodeled in 2018. This residence showcases impeccable craftsmanship and thoughtful design, ensuring a comfortable and stylish living experience. Upon entering, you'll be greeted by an inviting foyer that leads you into the heart of the home. The main level features an open-concept layout, allowing for effortless flow and an abundance of natural light. The spacious living area is perfect for entertaining guests or relaxing with loved ones. The kitchen exudes modern sophistication with its sleek cabinetry, high-end appliances and exquisite countertops, and offers plenty of dining space for hosting friends and family. The first floor has three bedrooms and 3.5 baths, and extra space that could be an additional bedroom or office space. A highlight of this property is the addition of a second floor completed during the 2018 remodel. Here, you'll find a luxurious primary suite that serves as a private oasis. The main bedroom offers a tranquil retreat, featuring generous proportions and ample closet space. The accompanying main bath is a spa-like sanctuary, complete with a walk-in shower and contemporary fixtures, providing the ultimate in relaxation and comfort. The second floor also offers an additional bedroom with its own private bath and a flexible space that could be another bedroom, media room or additional office. Throughout the home, attention to detail is evident in the choice of finishes and fixtures, which perfectly complement the contemporary style. From the sleek flooring to the designer lighting, every aspect has been carefully selected to create a cohesive and visually striking environment. The outdoor spaces are equally impressive, with a professionally landscaped yard and a spacious patio area. Whether you prefer to unwind in the privacy of your own backyard or host gatherings for friends and family, this property offers the ideal setting. Located in a wonderful neighborhood, this home is conveniently situated near top-rated schools, Park Avenue shopping and dining, and the Winter Park Racquet Club and Interlachen Country Club. With its ideal blend of classic charm and modern updates, this fully remodeled residence is a rare find, offering an exceptional opportunity for those seeking a contemporary lifestyle in a sought-after location.

    Zillow last checked:

    Listing updated:

    Listed by:

    Alison Mosley 407-304-6458,

    PREMIER SOTHEBY'S INTL. REALTY 407-644-3295

    Bought with:

    Gioconda Martins, 3538509

    LA ROSA REALTY DOWNTOWN ORLANDO LLC

    Source: Stellar MLS,MLS#: O6116476MLS LogoOriginating MLS: Orlando Regional

    Facts & features

    Interior

    Bedrooms & bathrooms
    • Bedrooms: 6
    • Bathrooms: 6
    • Full bathrooms: 5
    • 1/2 bathrooms: 1
    Rooms
    • Room types: Bonus Room, Breakfast Room Separate, Utility Room, Media Room
    Primary bedroom
    • Level: Second
    Bedroom 2
    • Level: First
    • Dimensions: 11x12
    Bedroom 3
    • Level: First
    • Dimensions: 16x12
    Bedroom 4
    • Level: First
    • Dimensions: 13x10
    Bedroom 5
    • Level: Second
    Dining room
    • Level: First
    • Dimensions: 17x10
    Foyer
    • Level: First
    • Dimensions: 8x6
    Kitchen
    • Level: First
    • Dimensions: 17x12
    Living room
    • Level: First
    • Dimensions: 20x12
    Heating
    • Central, Electric
    Cooling
    • Central Air
    Appliances
    • Included: Oven, Cooktop, Dishwasher, Microwave, Range, Range Hood, Refrigerator
    • Laundry: Laundry Room
    Features
    • Eating Space In Kitchen, High Ceilings, Kitchen/Family Room Combo, PrimaryBedroom Upstairs, Open Floorplan, Walk-In Closet(s)
    • Flooring: Engineered Hardwood, Terrazzo, Tile
    • Has fireplace: Yes
    • Fireplace features: Living Room, Wood Burning
    Interior area
    • Total structure area: 4,864
    • Total interior livable area: 4,182 sqft

    Property

    Parking
    • Total spaces: 2
    • Parking features: Garage - Attached
    • Attached garage spaces: 2
    Features
    • Levels: Two
    • Stories: 2
    • Patio & porch: Patio
    • Exterior features: Irrigation System, Private Mailbox, Sidewalk
    • Has private pool: Yes
    • Pool features: Heated, In Ground
    • Fencing: Fenced
    Lot
    • Size: 0.25 Acres
    • Features: Oversized Lot
    • Residential vegetation: Bamboo
    Details
    • Parcel number: 322130453606131
    • Zoning: R-1A
    • Special conditions: None

    Construction

    Type & style
    • Home type: SingleFamily
    • Architectural style: Contemporary
    • Property subtype: Single Family Residence
    Materials
    • Block, Stucco, Wood Frame
    • Foundation: Block, Slab
    • Roof: Membrane
    Condition
    • New construction: No
    • Year built: 1963

    Utilities & green energy

    • Sewer: Public Sewer
    • Water: None
    • Utilities for property: Cable Available, Cable Connected, Phone Available, Propane, Underground Utilities

    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: $526/sqft
    • Tax assessed value: $1,861,696
    • Annual tax amount: $7,728
    • Date on market: 6/8/2023
    • Cumulative days on market: 69 days
    • Listing terms: Cash,Conventional,VA Loan
    • Ownership: Fee Simple
    • Total actual rent: 0
    • Road surface type: Brick

    Price history

    DateEventPrice
    3/8/2025Listing removed$1,977,000$473/sqft
    Source: Stellar MLS #O6176048 Report a problem
    3/7/2025Listing removed$7,500$2/sqft
    Source: Stellar MLS #O6282631 Report a problem
    2/24/2025Price change$7,500+8.7%$2/sqft
    Source: Stellar MLS #O6282631 Report a problem
    2/20/2025Listed for rent$6,900$2/sqft
    Source: Stellar MLS #O6282631 Report a problem
    11/14/2024Price change$1,977,000-12.1%$473/sqft
    Source: Stellar MLS #O6176048 Report a problem
    7/29/2024Price change$2,250,000-8.2%$538/sqft
    Source: Stellar MLS #O6176048 Report a problem
    4/19/2024Listed for sale$2,450,000$586/sqft
    Source: Stellar MLS #O6176048 Report a problem
    3/20/2024Listing removed--
    Source: Stellar MLS #O6176048 Report a problem
    2/29/2024Price change$2,450,000-5.8%$586/sqft
    Source: Stellar MLS #O6176048 Report a problem
    2/3/2024Listed for sale$2,600,000+18.2%$622/sqft
    Source: Stellar MLS #O6176048 Report a problem
    9/19/2023Sold$2,200,000-6.5%$526/sqft
    Source: Stellar MLS #O6116476 Report a problem
    8/17/2023Pending sale$2,352,000$562/sqft
    Source: Stellar MLS #O6116476 Report a problem
    8/10/2023Price change$2,352,000-2%$562/sqft
    Source: Stellar MLS #O6116476 Report a problem
    6/8/2023Listed for sale$2,400,000+336.4%$574/sqft
    Source: Stellar MLS #O6116476 Report a problem
    8/6/2015Sold$549,900-4.3%$131/sqft
    Source: Public Record Report a problem
    6/1/2015Pending sale$574,900$137/sqft
    Source: FANNIE HILLMAN & ASSOCIATES #O5344162 Report a problem
    5/27/2015Price change$574,900-3.4%$137/sqft
    Source: Fannie Hillman & Associates #O5344162 Report a problem
    1/31/2015Listed for sale$594,900-0.8%$142/sqft
    Source: Fannie Hillman + Associates, Inc. #O5344162 Report a problem
    11/30/2014Listing removed$599,500$143/sqft
    Source: Central Orlando Realty LLC DBA Keller Williams at the Parks #O5306717 Report a problem
    9/10/2014Price change$599,500-4.7%$143/sqft
    Source: Central Orlando Realty LLC DBA Keller Williams at the Parks #O5306717 Report a problem
    7/13/2014Price change$629,000-3.1%$150/sqft
    Source: Central Orlando Realty LLC DBA Keller Williams at the Parks #O5306717 Report a problem
    5/3/2014Price change$649,000-3.9%$155/sqft
    Source: Owner Report a problem
    2/15/2014Listed for sale$675,000+214%$161/sqft
    Source: Owner Report a problem
    10/9/1997Sold$215,000$51/sqft
    Source: Public Record Report a problem

    Public tax history

    YearProperty taxesTax assessment
    2024$29,011 +252.1%$1,861,696 +234.9%
    2023$8,240 +6.6%$555,902 +3%
    2022$7,728 +1.1%$539,711 +3%
    2021$7,644 -2.5%$523,991 -0.8%
    2020$7,842 -7.2%$528,153 -5.2%
    2019$8,454 +0.4%$557,258 +1.8%
    2018$8,418 $547,377 +13.5%
    2017$8,418 +16.5%$482,228 +4.9%
    2016$7,225 +2.1%$459,702 +16.4%
    2015$7,077 +138.1%$395,061 +40.8%
    2014$2,973 +2.5%$280,670 +21.8%
    2013$2,901 +1.3%$230,495 +10%
    2012$2,863 +3.4%$209,565 -8.3%
    2011$2,769 +5.6%$228,416 -11.3%
    2010$2,623 $257,576 -18.2%
    2009-- $314,824 -16.3%
    2008$2,487 -4.7%$376,126 -14.5%
    2007$2,609 -6.3%$439,928 +38.1%
    2006$2,786 +0.2%$318,572 +9.6%
    2005$2,781 +4.8%$290,717 +37.3%
    2004$2,654 +5.8%$211,675 +1.2%
    2003$2,510 +2.9%$209,205 +16%
    2002$2,439 +0.5%$180,402 +5.5%
    2001$2,426 +2.7%$171,065 +3.6%
    2000$2,362 $165,160
    Find assessor info on the county website

    Neighborhood: 32789

    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
    $2,266,200
    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
    $2,266,200