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For sale
    • $895,000

    557 Upper Grassy Hill Road, Woodbury, CT 06798

    4beds
    3,784sqft
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    Single Family Residence
    Built in 1999
    2.73 Acres Lot
    $-- Zestimate®
    $237/sqft
    $-- HOA

    What's special

    Decorative gas fireplaceStone wallsMurphy bedStunning bluestone patioPrivate home officeBelgium block-lined drivewayIrrigation system
    Welcome to Upper Grassy Hill Living! This stunning Colonial offers 3784 sf on three levels of thoughtfully designed living space in the sought-after Upper Grassy Hill community. From the moment you enter the grand two-story foyer with gleaming marble floors, you'll be captivated by the home's timeless elegance and comfort.The main level features a formal, front-to-back living and dining room perfect for entertaining, along with a private home office ideal for today's lifestyle. The sun-drenched kitchen boasts granite countertops, stainless steel appliances, a pantry, and a skylight and flows effortlessly into the spacious sunken family room with vaulted ceiling and a cozy pellet stove. Just off the kitchen, step out onto the expansive deck, offering privacy and distant views-your own private outdoor escape. Upstairs, you'll find three generous bedrooms, including a luxurious primary suite with hardwood floors, trey ceiling, dual walk-in closets, and a beautifully remodeled spa bath. A dressing room/sitting room adds the perfect finishing touch to this serene retreat. The fully finished walk-out lower level is an exceptional in-law or au pair setup. It features hardwood floors throughout, a kitchen area with granite counters, a bedroom with built-ins, a Murphy bed and a decorative gas fireplace. There is also a spa-like marble bath complete with a steam shower, and a spacious great room with built-in seating. French doors lead to a stunning bluestone patio with a plunge pool/spa-perfect for relaxing or entertaining. Additional highlights include: surround sound, a Belgium block-lined driveway, stone walls, irrigation system, and a generator. Located just 90 minutes from NYC, this home is part of the self-managed Cardinal Hill HOA ($100/year), and backs up to designated open space for added privacy and peace of mind. This is more than a home-it's a lifestyle. PLEASE NOTE: interior/exterior security cameras/video. 24/7 monitoring
    94 days
    |
    719
    |
    41
    |

    Zillow last checked:

    Listing updated:

    Listed by:

    Susan Corleto (203)470-3918,

    William Pitt Sotheby's Int'l 203-796-7700

    Source: Smart MLS,MLS#: 24158380MLS Logo

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      Facts & features

      Interior

      Bedrooms & bathrooms
      • Bedrooms: 4
      • Bathrooms: 4
      • Full bathrooms: 3
      • 1/2 bathrooms: 1
      Rooms
      • Room types: Bonus Room
      Primary bedroom
      • Features: High Ceilings, Bedroom Suite, Dressing Room, Full Bath, Walk-In Closet(s)
      • Level: Upper
      • Area: 256.8 Square Feet
      • Dimensions: 12 x 21.4
      Bedroom
      • Features: Vinyl Floor
      • Level: Upper
      • Area: 115.44 Square Feet
      • Dimensions: 10.4 x 11.1
      Bedroom
      • Features: Wall/Wall Carpet
      • Level: Upper
      • Area: 116.55 Square Feet
      • Dimensions: 10.5 x 11.1
      Bedroom
      • Features: High Ceilings, Built-in Features, Gas Log Fireplace, Hardwood Floor
      • Level: Lower
      • Area: 115.5 Square Feet
      • Dimensions: 10.5 x 11
      Dining room
      • Features: High Ceilings, Hardwood Floor
      • Level: Main
      • Area: 184.34 Square Feet
      • Dimensions: 12.2 x 15.11
      Family room
      • Features: Palladian Window(s), Vaulted Ceiling(s), Ceiling Fan(s), Pellet Stove, Hardwood Floor
      • Level: Main
      • Area: 283.75 Square Feet
      • Dimensions: 14.11 x 20.11
      Great room
      • Features: High Ceilings, Built-in Features, Dining Area, French Doors, Patio/Terrace, Hardwood Floor
      • Level: Lower
      • Area: 523.91 Square Feet
      • Dimensions: 17.4 x 30.11
      Kitchen
      • Features: Skylight, High Ceilings, Balcony/Deck, Granite Counters, Pantry, Hardwood Floor
      • Level: Main
      • Area: 350.88 Square Feet
      • Dimensions: 17.2 x 20.4
      Living room
      • Features: High Ceilings, Hardwood Floor
      • Level: Main
      • Area: 174.72 Square Feet
      • Dimensions: 11.2 x 15.6
      Office
      • Features: High Ceilings, French Doors, Hardwood Floor
      • Level: Main
      • Area: 133.2 Square Feet
      • Dimensions: 11.1 x 12
      Other
      • Features: Hardwood Floor
      • Level: Upper
      • Area: 192.91 Square Feet
      • Dimensions: 10.1 x 19.1
      Heating
      • Forced Air, Oil, Propane
      Cooling
      • Central Air, Zoned
      Appliances
      • Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Wine Cooler, Water Heater
      • Laundry: Upper Level
      Features
      • Sound System, Wired for Data, Open Floorplan, Entrance Foyer
      • Doors: French Doors
      • Basement: Full,Heated,Finished,Cooled,Walk-Out Access,Liveable Space
      • Attic: Pull Down Stairs
      • Number of fireplaces: 2
      Interior area
      • Total structure area: 3,784
      • Total interior livable area: 3,784 sqft
      • Finished area above ground: 2,791
      • Finished area below ground: 993

      Property

      Parking
      • Total spaces: 2
      • Parking features: Attached, Garage Door Opener
      • Attached garage spaces: 2
      Features
      • Patio & porch: Deck, Patio
      • Exterior features: Rain Gutters, Underground Sprinkler
      • Has private pool: Yes
      • Pool features: Fenced, In Ground
      Lot
      • Size: 2.73 Acres
      • Features: Borders Open Space, Dry, Level, Sloped, Landscaped, Open Lot
      Details
      • Parcel number: 934825
      • Zoning: OS80
      • Other equipment: Generator

      Construction

      Type & style
      • Home type: SingleFamily
      • Architectural style: Colonial,Contemporary
      • Property subtype: Single Family Residence
      Materials
      • Vinyl Siding
      • Foundation: Concrete Perimeter
      • Roof: Asphalt
      Condition
      • New construction: No
      • Year built: 1999

      Utilities & green energy

      • Sewer: Septic Tank
      • Water: Well

      Community & HOA

      Community
      • Features: Golf, Health Club, Lake, Library, Medical Facilities, Park, Private School(s)
      • Security: Security System
      HOA
      • Has HOA: No
      Location
      • Region: Woodbury

      Financial & listing details

      • Price per square foot: $237/sqft
      • Tax assessed value: $553,840
      • Annual tax amount: $13,082
      • Date on market: 4/1/2026

        Estimated market value

        Not available

        Estimated sales range

        Not available

        Not available

        Price history

        DateEventPrice
        4/1/2026Listed for sale$895,000-2.2%$237/sqft
        Source: Smart MLS #24158380 Report a problem
        10/24/2025Listing removed$915,000$242/sqft
        Source: Smart MLS #24104194 Report a problem
        9/16/2025Price change$915,000-3.7%$242/sqft
        Source: Smart MLS #24104194 Report a problem
        7/30/2025Price change$949,900-4.9%$251/sqft
        Source: Smart MLS #24104194 Report a problem
        6/30/2025Listed for sale$999,000+29.7%$264/sqft
        Source: Smart MLS #24104194 Report a problem
        3/1/2024Sold$770,000+0.7%$203/sqft
        Source: Smart MLS #170606501 Report a problem
        2/28/2024Pending sale$765,000$202/sqft
        Source: Smart MLS #170606501 Report a problem
        1/2/2024Price change$765,000-3.8%$202/sqft
        Source: Smart MLS #170606501 Report a problem
        11/24/2023Listed for sale$795,000$210/sqft
        Source: Smart MLS #170606501 Report a problem
        11/12/2023Contingent$795,000$210/sqft
        Source: Smart MLS #170606501 Report a problem
        10/30/2023Listed for sale$795,000+31.4%$210/sqft
        Source: Smart MLS #170606501 Report a problem
        8/4/2021Sold$605,000+0.8%$160/sqft
        Source: Smart MLS #170366978 Report a problem
        2/8/2021Contingent$599,995$159/sqft
        Source: Smart MLS #170366978 Report a problem
        2/1/2021Listed for sale$599,995$159/sqft
        Source: Smart MLS #170366978 Report a problem
        10/27/2020Listing removed$599,995$159/sqft
        Source: William Pitt Sotheby's International Realty #170232058 Report a problem
        1/19/2020Price change$599,995-2.4%$159/sqft
        Source: William Pitt Sotheby's International Realty #170232058 Report a problem
        9/13/2019Listed for sale$615,000-5.2%$163/sqft
        Source: William Pitt Sotheby's International Realty #170232058 Report a problem
        7/1/2019Listing removed$649,000$172/sqft
        Source: William Pitt Sotheby's International Realty #170139389 Report a problem
        5/23/2019Price change$649,000-3%$172/sqft
        Source: William Pitt Sotheby's International Realty #170139389 Report a problem
        1/29/2019Price change$669,000-8.2%$177/sqft
        Source: William Pitt Sotheby's International Realty #170139389 Report a problem
        10/27/2018Listed for sale$729,000$193/sqft
        Source: William Pitt Sotheby's International Realty #170139389 Report a problem

        Public tax history

        YearProperty taxesTax assessment
        2025$13,082 +1.9%$553,840
        2024$12,832 +3.6%$553,840 +30%
        2023$12,382 -0.4%$426,090
        2022$12,429 $426,090
        2021$12,429 $426,090
        2020$12,429 $426,090
        2019$12,429 +23.3%$426,090 +12.4%
        2018$10,077 -2.1%$379,110
        2017$10,297 +3.3%$379,110
        2016$9,967 +0.8%$379,110
        2015$9,883 +1.5%$379,110
        2014$9,739 +0.4%$379,110 -8.6%
        2013$9,704 -3.2%$414,720 +0.2%
        2012$10,028 +12.3%$413,880 +4.1%
        2011$8,929 +17%$397,530 +11.7%
        2010$7,634 +1.5%$355,910
        2009$7,520 +1.2%$355,910 +16.6%
        2008$7,434 +1.6%$305,290
        2007$7,315 +5.1%$305,290
        2006$6,958 +6.4%$305,290
        2005$6,539 $305,290
        2004$6,539 +28%$305,290 +62.8%
        2003$5,110 $187,530

        Find assessor info on the county website

        Monthly payment

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        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: 06798

        Getting around

        0 / 100
        Car-Dependent

        Nearby schools

        GreatSchools rating
        Schools provided by the listing agent
        • High: Nonnewaug

        Source: Smart 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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