557 Upper Grassy Hill Rd

Woodbury, CT 06798

$895,000
Price
4
Beds
3,784 Sq. Ft.
$237 / Sq. Ft.
3,784
Sq. Ft.
$237
per Sq. Ft.
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a front view of a house with a yard
a view of a houses with a yard
an aerial view of a house with garden space and car parked
a living room with furniture and a large window
a view of an entryway with staircase
a view of an empty room with wooden floor and a window
a dining room with wooden floor and a rug
a bedroom with furniture and a window
a kitchen with granite countertop wooden floors white cabinets and stainless steel appliances
a kitchen with stainless steel appliances granite countertop a stove top oven a sink dishwasher a dining table and chairs with wooden floor
a kitchen with stainless steel appliances granite countertop wooden floors and refrigerator
a living room with furniture and a flat screen tv
a living room with fireplace furniture and a large window
a view of entryway
a bedroom with a bed and wooden floor
a living room with furniture and a wooden floor
a spacious bedroom with a balcony a bed and wooden floor
a view of a living room and kitchen
a view of walk in closet with clothes and shoes
a bathroom with a double vanity sink a toilet and shower
a spacious bathroom with a bathtub and window
a view of a storage & utility room with a window
a large bed sitting in a bedroom next to a window with a chair
a bed sitting in a bedroom next to a window
a bathroom with a granite countertop shower and a sink
a kitchen with stainless steel appliances granite countertop a stove and a sink
a living room with furniture and large windows
a living room with furniture and a large window
a view of empty room with wooden floor
a living room with furniture and a wooden floor
a big room with wooden floor and a ceiling fan
a bathroom with a sink a toilet and a mirror
a balcony with wooden floor and city view
a view of swimming pool from a balcony
a view of a backyard with a sitting area
a view of sunset and yard
unknown
a picture of a floor plan

Description

Welcome to Upper Grassy Hill Living!Welcome to Upper Grassy Hill Living!
  1. Listed by Susan Corleto • William Pitt Sotheby's Int'l
    P: (203)-470-3918 C: (203)-470-3918 scorleto@wpsir.com

Property Details for 557 Upper Grassy Hill Road

Basement Description
Full, Heated, Fully Finished, Cooled, Walk-out, Liveable Space, Full With Walk-Out
Direct Waterfront
No
Garages Number
2
Neighborhood
N/A
Style
Colonial, Contemporary
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 04/24/2026 10:26 PM

Property Details for 557 Upper Grassy Hill Road

StatusActive
MLS #24158380
Days on Market40
Taxes$13,082 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1999
Lot Size2.73 AC / 118,918 SF
CountyLitchfield County
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Location

Listing Courtesy of William Pitt Sotheby's Int'l, Susan Corleto
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Building Information for 557 Upper Grassy Hill Road

Stories-Year Built1999Building Size-Lot Size2.73 AC / 118,918 SF

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$5,597 per month

30 year fixed, 6.46% Interest

Principal and Interest

$4,507

Property Taxes

$1,090

HOA Dues

$0

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Property Information for 557 Upper Grassy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Transylvania to Upper Grassy Hill
  • Elementary School: Per Board of Ed
  • High School: Nonnewaug
  • Latitude: 41.522533
  • Longitude: -73.249016
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Medical Facilities, Park, Private School(s)
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $13,082
Interior and Exterior Features
Exterior Features
  • Exterior Features: Deck, Gutters, French Doors, Underground Sprinkler, Patio
  • Pool Description: Safety Fence, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Refrigerator, Dishwasher, Wine Chiller
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: bedroom level
  • Rooms Additional: Bonus Room, Foyer
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Length: 15.6
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 11.2
Room 2
  • Room Entry Order: 10
  • Room Features: 9 ft+ Ceilings,Built-Ins,Gas Log Fireplace,Hardwood Floor
  • Room Length: 11.0
  • Room Level: Lower
  • Room Type: Bedroom
  • Room Width: 10.5
Room 3
  • Room Entry Order: 11
  • Room Features: 9 ft+ Ceilings,Built-Ins,Dining Area,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 30.11
  • Room Level: Lower
  • Room Type: Great Room
  • Room Width: 17.4
Room 4
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Length: 15.11
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 12.2
Room 5
  • Listing Key: 4C99EBAEC39A6785E0631A01100A7265
  • Room Entry Order: 3
  • Room Features: Palladian Window(s),Vaulted Ceiling,Ceiling Fan,Pellet Stove,Hardwood Floor
  • Room Length: 20.11
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 14.11
Room 6
  • Room Entry Order: 4
  • Room Features: Skylight,9 ft+ Ceilings,Balcony/Deck,Granite Counters,Pantry,Hardwood Floor
  • Room Length: 20.4
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 17.2
Room 7
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,French Doors,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 11.1
Room 8
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Bedroom Suite,Dressing Room,Full Bath,Walk-In Closet
  • Room Length: 21.4
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 12.0
Room 9
  • Listing Key: 4C99EBAEC39A6785E0631A01100A7265
  • Room Entry Order: 7
  • Room Features: Hardwood Floor
  • Room Length: 19.1
  • Room Level: Upper
  • Room Type: Other
  • Room Width: 10.1
Room 10
  • Room Entry Order: 8
  • Room Features: Vinyl Floor
  • Room Length: 11.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.4
Room 11
  • Room Entry Order: 9
  • Room Features: Wall/Wall Carpet
  • Room Length: 11.1
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 10.5
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1999
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Separate Entry
  • In Law Apartment: Possible
  • Sq Ft Description: Includes w/o In-law/au-pair apartment
  • Sq Ft Est Heated Below Grade: 993
  • Living Area SQFT Per Public Records: 2791
Lot Information
  • Lot Description: Borders Open Space, Dry, Level Lot, Sloping Lot, Professionally Landscaped, Open Lot
  • Parcel Number: 934825
  • Sq Ft Est Heated Above Grade: 2791.0
  • Sq Ft Total: 3784.0
  • Zoning: OS80
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil, Propane
  • Hot Water Description: Domestic, Upright Tank, 40 Gallon Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 557 Upper Grassy Hill Road

DateEvent & SourcePriceAppreciation
Mar 1, 2024

Closed (Public Record)

Public Record #1528433513

$770,000

+9.8% / yr

Aug 4, 2021

Closed (Public Record)

Public Record #1468429171

$605,000—
DateEvent & SourcePrice
03/01/2024

Closed (Public Record)

Public Record #1528433513

$770,000

+9.8% / yr

08/04/2021

Closed (Public Record)

Public Record #1468429171

$605,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 557 Upper Grassy Hill Road

Taxable ValueLand$86,940Additions$466,900Total$553,840
Tax Record2024$13,082 ($1,090 / month)
Home Facts
Beds4Baths3.5Total Finished SqFt2,791 SqFtAbove Grade Finished SqFt2,791 SqFtUnfinished Basement SqFt467 SqFtStories2Lot Size118,919 SqFtStyleSingle Family ResidenceYear Built1999Year Renovated2016ZoningOS80CountyNAUGATUCK VALLEYAPNWOOD M:062 B:022L L:12Fireplace TypeHas Fireplace

Schools near 557 Upper Grassy Hill Road

This home is within Regional School District 14.
Rating
School
Type
Grades
Distance
Bethlehem Elementary School
Public - PK to 5
Mitchell Elementary School
Public - PK to 5
Woodbury Middle School
Public - 6 to 8
Nonnewaug High School
Public - 9 to 12
Rating
School
Distance
Bethlehem Elementary School
PublicPK to 5

Mitchell Elementary School
PublicPK to 5

Woodbury Middle School
Public6 to 8

Nonnewaug High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 557 Upper Grassy Hill Road, Woodbury, CT 06798

557 Upper Grassy Hill Road is a single family home for sale in Woodbury, CT 06798. This property was listed for sale on April 1, 2026 by William Pitt Sotheby's Int'l, it's currently listed at $895,000. It has been on the market for a total of 40 days and was last sold on March 1, 2024. This listing's school district is Regional School District 14. Nearby schools include Bethlehem Elementary School, Mitchell Elementary School and Woodbury Middle School. 557 Upper Grassy Hill Road is a 4-bed, 4-bath, 3,784 sqft single family home built in 1999.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Susan Corleto

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.