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For sale
    • Price cut: $10K (6/26)
    $889,000

    442 BRIERCLIFF DRIVE, ORLANDO, FL 32806

    4beds
    2,688sqft
    : 
    $5,883/mo
    Get pre-qualified
    Single Family Residence
    Built in 1925
    7,267 Square Feet Lot
    $856,700 Zestimate®
    $331/sqft
    $-- HOA

    What's special

    Timeless charmSpacious islandViews of the backyardCustom cabinetryDry barSeparate soaking tubLarge built-in closets
    Timeless charm meets refined living in this beautifully updated historic home in the heart of Delaney Park, complete with a detached guest house and thoughtfully designed living spaces. Offering 4 bedrooms, 4 bathrooms, and 2,688 square feet, this residence blends classic character with modern comfort in one of downtown Orlando’s most desirable neighborhoods. Inside, a welcoming living room with a built-in wood-burning fireplace creates a warm focal point and flows seamlessly into the separate dining room, both highlighted by wood flooring. Just beyond, the kitchen is designed for both everyday living and entertaining, featuring custom cabinetry, stone countertops, stainless steel appliances, a spacious island, dry bar, and generous cabinet and counter space. The kitchen overlooks a stunning family room with vaulted ceilings and an abundance of large windows and doors that fill the space with natural light while offering views of the backyard. The main level includes two bedrooms and two full bathrooms, providing flexibility for a variety of living arrangements. Upstairs, the private primary suite serves as a peaceful retreat with large built-in closets and a beautifully renovated en suite bathroom featuring dual sinks, a spacious glass walk-in shower with a built-in bench, and a separate soaking tub. The detached guest house includes a full bathroom, air conditioning, and a convenient kitchenette, providing a perfect space for guests, work, or hobbies. The fenced backyard with a large stone porch is ideal for entertaining or quiet evenings outdoors. Perfectly situated in the heart of downtown Orlando, this home offers effortless access to dining, shopping, and major roadways, with world-famous theme parks and Orlando International Airport just a short drive away—combining timeless elegance with modern city living. Mortgage savings may be available for buyers of this listing.
    131 days
    |
    884
    |
    68
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Wylie Devlin 407-463-1014,

    REDFIN CORPORATION 407-708-9747

    Source: Stellar MLS,MLS#: O6390631MLS LogoOriginating MLS: Orlando Regional

      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 4
      Rooms
      • Room types: Family Room
      Primary bedroom
      • Features: Ceiling Fan(s), En Suite Bathroom, Built-in Closet
      • Level: Second
      Primary bathroom
      • Features: Dual Sinks, Tub with Separate Shower Stall
      • Level: Second
      Family room
      • Features: Ceiling Fan(s)
      • Level: First
      Kitchen
      • Features: Kitchen Island
      • Level: First
      Living room
      • Features: Other
      • Level: First
      Heating
      • Central, Electric
      Cooling
      • Central Air
      Appliances
      • Included: Dishwasher, Microwave, Range, Refrigerator
      • Laundry: Inside, Laundry Room
      Features
      • Built-in Features, Ceiling Fan(s), Dry Bar, Eating Space In Kitchen, High Ceilings, Other, PrimaryBedroom Upstairs, Stone Counters, Vaulted Ceiling(s)
      • Flooring: Tile, Hardwood
      • Has fireplace: Yes
      • Fireplace features: Living Room, Wood Burning
      Interior area
      • Total structure area: 2,868
      • Total interior livable area: 2,688 sqft
      Video & virtual tour

      Property

      Parking
      • Parking features: Driveway, Electric Vehicle Charging Station(s)
      • Has uncovered spaces: Yes
      Features
      • Levels: Two
      • Stories: 2
      • Patio & porch: Rear Porch
      • Exterior features: Lighting, Other, Sidewalk
      • Fencing: Fenced,Wood
      • Has view: Yes
      • View description: Trees/Woods
      Lot
      • Size: 7,267 Square Feet
      • Features: Landscaped, Level, Sidewalk
      Details
      • Additional structures: Guest House
      • Parcel number: 362229000000062
      • Zoning: R-1/T/AN
      • Special conditions: None

      Construction

      Type & style
      • Home type: SingleFamily
      • Property subtype: Single Family Residence
      Materials
      • Stucco, Wood Frame
      • Foundation: Crawlspace
      • Roof: Shingle
      Condition
      • New construction: No
      • Year built: 1925

      Utilities & green energy

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

      Community & HOA

      Community
      • Pet fee: $0 monthly
      HOA
      • Has HOA: No
      Location
      • Region: Orlando

      Financial & listing details

      • Price per square foot: $331/sqft
      • Tax assessed value: $796,446
      • Annual tax amount: $13,489
      • Date on market: 3/19/2026
      • Cumulative days on market: 131 days
      • Listing terms: Cash,Conventional,FHA,VA Loan
      • Ownership: Fee Simple
      • Total actual rent: 0
      • Electric utility on property: Yes
      • Road surface type: Paved, Asphalt

        Estimated market value

        $856,700

        $814,000 - $900,000

        $4,279/mo

        Price history

        DateEventPrice
        6/26/2026Price change$889,000-1.1%$331/sqft
        Source: Stellar MLS #O6390631 Report a problem
        6/5/2026Price change$899,000-2.8%$334/sqft
        Source: Stellar MLS #O6390631 Report a problem
        3/31/2026Price change$925,000-2.6%$344/sqft
        Source: Stellar MLS #O6390631 Report a problem
        3/19/2026Listed for sale$950,000+13.8%$353/sqft
        Source: Stellar MLS #O6390631 Report a problem
        7/20/2022Sold$835,000+5%$311/sqft
        Source: Public Record Report a problem
        6/21/2022Pending sale$795,000$296/sqft
        Source: Stellar MLS #O6030357 Report a problem
        6/2/2022Listed for sale$795,000+104.9%$296/sqft
        Source: Stellar MLS #O6030357 Report a problem
        3/17/2017Sold$388,000-22.2%$144/sqft
        Source: Public Record Report a problem
        8/8/2015Listing removed$2,300$1/sqft
        Source: Zillow Rental Network Report a problem
        7/20/2015Listed for rent$2,300+7%$1/sqft
        Source: Zillow Rental Network Report a problem
        7/20/2015Listing removed$499,000$186/sqft
        Source: ORLANDO REO PROF I INC #O5322826 Report a problem
        6/15/2015Price change$499,000-3.9%$186/sqft
        Source: ORLANDO REO PROF I INC #O5322826 Report a problem
        4/30/2015Price change$519,000-1.9%$193/sqft
        Source: ORLANDO REO PROF I INC #O5322826 Report a problem
        4/9/2015Price change$529,000-3.6%$197/sqft
        Source: ORLANDO REO PROF I INC #O5322826 Report a problem
        2/24/2015Price change$549,000-1.8%$204/sqft
        Source: Orlando REO Professionals I, Inc. #O5322826 Report a problem
        12/6/2014Price change$559,000-3.5%$208/sqft
        Source: Orlando REO Professionals I, Inc. #O5322826 Report a problem
        11/8/2014Price change$579,000-3.3%$215/sqft
        Source: Orlando REO Professionals I, Inc. #O5322826 Report a problem
        10/3/2014Listed for sale$599,000+4.2%$223/sqft
        Source: Orlando REO Professionals I, Inc. #O5322826 Report a problem
        10/2/2012Listing removed$2,150$1/sqft
        Source: Coldwell Banker Residential Real Estate (99005919) Report a problem
        9/28/2012Listed for rent$2,150$1/sqft
        Source: Coldwell Banker Residential Real Estate (99005919) Report a problem
        8/25/2008Listing removed$575,000$214/sqft
        Source: NRT Florida #O4765065 Report a problem
        6/20/2008Listed for sale$575,000+112.2%$214/sqft
        Source: NRT Florida #O4765065 Report a problem
        3/18/2004Sold$271,000+8.4%$101/sqft
        Source: Public Record Report a problem
        7/10/2003Sold$250,000+29.9%$93/sqft
        Source: Public Record Report a problem
        6/20/2002Sold$192,500+49.8%$72/sqft
        Source: Public Record Report a problem
        11/11/1998Sold$128,500$48/sqft
        Source: Public Record Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2024$13,074 +3.7%$754,625 +3%
        2023$12,606 +104.7%$732,646 +95.6%
        2022$6,158 +1.6%$374,480 +3%
        2021$6,060 +0.8%$363,573 +1.4%
        2020$6,011 +1.1%$358,553 +2.3%
        2019$5,947 +1%$350,492 +1.9%
        2018$5,889 $343,957 -2.6%
        2017$5,889 -14.6%$353,101 -17.6%
        2016$6,898 -18.8%$428,523 +8.9%
        2015$8,499 +16.4%$393,500 +10.9%
        2014$7,302 +9%$354,784 +3.3%
        2013$6,696 -1.7%$343,551 -1.1%
        2012$6,811 -2.6%$347,382 -2.3%
        2011$6,995 -11.4%$355,685 -14.2%
        2010$7,898 $414,547 -5.5%
        2009-- $438,513 -21.5%
        2008$10,180 +31.2%$558,263 -5.4%
        2007$7,760 -6.1%$590,322 +29.3%
        2006$8,262 +97.9%$456,585 +118.5%
        2005$4,174 +3.4%$208,959 +1.9%
        2004$4,037 +35.2%$205,056 +37.9%
        2003$2,986 +22.1%$148,744 +22.7%
        2002$2,445 +3.3%$121,262 +6.3%
        2001$2,368 +34.6%$114,097 +2.7%
        2000$1,760 $111,092
        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.
        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: Delaney Park

        Getting around

        48 / 100
        Car-Dependent
        43 / 100
        Some Transit
        75 / 100
        Very Bikeable

        Nearby schools

        GreatSchools rating

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