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Sold for $885,000
    • $885,000

    557 Upper Grassy Hill Road, Woodbury, CT 06798

    4beds
    3,784sqft
    Single Family Residence
    Built in 1999
    2.73 Acres Lot
    $891,400 Zestimate®
    $234/sqft
    $5,982 Estimated rent

    Home value

    $891,400

    $811,000 - $981,000

    $5,982/mo

    Zestimate® history
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    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

    Zillow last checked:

    Listing updated:

    Listed by:

    Susan Corleto (203)470-3918,

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

    Bought with:

    Margaretann Fiderio, RES.0807559

    William Raveis Real Estate

    Source: Smart MLS,MLS#: 24158380MLS Logo

    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: $234/sqft
    • Tax assessed value: $553,840
    • Annual tax amount: $13,082
    • Date on market: 4/1/2026

    Price history

    DateEventPrice
    7/30/2026Sold$885,000-1.1%$234/sqft
    Source: Smart MLS #24158380 Report a problem
    7/27/2026Pending sale$895,000$237/sqft
    Source: Smart MLS #24158380 Report a problem
    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

    Neighborhood: 06798

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    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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