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$1,267,500

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,676 Sq. Ft.
  • 5 Car Garage
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"Where Luxury Meets the Landscape." Welcome to a home where nature and craftsmanship converge in breathtaking harmony. Nestled on five professionally landscaped acres, this country manor is a sanctuary of serenity and sophistication. A statuesque quarry of stone lines one side of the property, perfectly balanced by a tranquil body of water-inviting you to kayak, canoe, or skate through the seasons or perhaps just enjoy the resident eagles or osprey who make the area their home during some of the year. As you enter, the grand open staircase is the centerpiece of a 2-story wrap-around Foyer that sets the stage for the comfortable elegance this home inspires. Step inside and experience the artistry of design. Sunlight pours through expansive windows, illuminating exquisite millwork: coffered ceilings, oversized crown and baseboard moldings, solid raised paneling, and wide-board hardwood floors. Every detail speaks to the builder's commitment to timeless quality. The grounds are thoughtfully engineered for beauty and function-featuring a level yard with industrial grade drainage, a low-maintenance milled crushed stone driveway, double-tiered decking, and a refreshing outdoor shower along with new stone seating area, walkways in the backyard.

Full Property Details for 101 Old Grassy Hill Rd

General

  • Price: $1,267,500
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24135665
  • Updated: 12/22/2025
  • Added to Site: 47 day(s) ago

Interior

  • Number of Rooms: 11
  • Rooms/Areas: Foyer, Laundry Room, Workshop
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Range Hood, Refrigerator, Dishwasher, Washer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: 9 ft+ Ceilings, Ceiling Fan, Full Bath, Hydro-Tub, Wal, 18 x 16, Upper
  • Bedroom 1: Bedroom - Ceiling Fan, Hardwood Floor, 14 x 14, Upper
  • Bedroom 2: Bedroom - Ceiling Fan, Hardwood Floor, 15 x 11, Upper
  • Bedroom 3: Bedroom - Ceiling Fan, Hardwood Floor, 20 x 19, Upper

Other Rooms

  • Living Room: Living Room - Hardwood Floor, 15 x 14, Main
  • Great Room: Great Room - Palladian Window(s), Gas Log Fireplace, Hardwood Floor, 22 x 21, Main
  • Eat In Kitchen: Eat-In Kitchen - Breakfast Nook, Granite Counters, Island, Pantry, Sliders, Hard, 45 x 33, Main
  • Formal Dining Room: Formal Dining Room - Bay/Bow Window, 9 ft+ Ceilings, Hardwood Floor, 16 x 14, Main
  • Office: Office - Built-Ins, Ceiling Fan, Full Bath, Wall/Wall Carpet, 24 x 15, Main
  • Theater/Media: Media Room - Built-Ins, Walk-In Closet, Wall/Wall Carpet, 18 x 16, Lower
  • Laundry: Upper Level

Exterior

  • Exterior Features: Underground Utilities, Shed, Porch, Deck, Gutters, Hot Tub, Stone Wall, Patio
  • Color: Moss

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 5
  • Parking: Attached Garage, Under House Garage

Location

  • County: Litchfield
  • Neighborhood: Grassy Hill
  • Driving Directions: Main Street South(Rt6) onto Rt317. Old Grassy Hill Road on left. End of the Cul de Sac on left hand side.

School Information

  • Elementary School: Per Board of Ed
  • High School: Nonnewaug

Community

  • Community Name: Grassy Hill

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Hydro Air, Zoned, Propane
  • Heating Fuel: Propane
  • Water Heater: 80 Gallon Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial, Contemporary
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Garage Access, Interior Access, Partially Finished, Walk-out, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Disability Access: 32" Minimum Door Widths, Bath Grab Bars, Hallways 36+ Inches Wide, Multiple Entries/Exits
  • Square Feet: 4,676
  • Above Ground: 3,976 Sq. Ft.
  • Below Ground: 700 Sq. Ft.
  • Year Built: 2004

Lot Features

  • Lot Size (Acres): 5.17
  • Zoning: OS80
  • Lot Description: Secluded, Lightly Wooded, On Cul-De-Sac, Professionally Landscaped, Water View

Water Features

  • Water Front: Yes
  • Water View: Yes
  • Water Front Desc.: Pond, Lake, Walk to Water, View

Green Features

  • Energy Features: Fireplace Insert, Ridge Vents, Thermopane Windows

Financial Considerations

  • Assessment Amount: $619,290
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Shed, portable generator, shed lawncare equipment, gar. refrigerator & shelving, some furnishings/decor items, home theater equip. & screen, gas grill negot
  • Property ID: 934419
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

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— 101 Old Grassy Hill Rd —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 101 Old Grassy Hill Rd

School District:Regional School District 14
NameGradesDistance
Mitchell Elementary School
14 School Street, Woodbury, CT 06798
PK-51.6 mi
Bethlehem Elementary School
92 East Street, Bethlehem, CT 06751
PK-57.5 mi
Woodbury Middle School
67 Washington Avenue, Woodbury, CT 06798
6-81.5 mi
Nonnewaug High School
5 Minortown Road, Woodbury, CT 06798
9-122.8 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 101 Old Grassy Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
12/16/2025
Listed
$1,267,500
105.76%
MLS
7/19/2019
Sold
$616,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 101 Old Grassy Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$14,628
2%
$619,290
—
2023
$14,349
10%
$619,290
38%
2023
$13,009
—
$447,660
—
2022
$13,058
—
$447,660
—
2021
$13,058
—
$447,660
—
2020
$13,058
—
$447,660
—
2019
$13,058
-3%
$447,660
-12%
2018
$13,492
-2%
$507,590
—
2017
$13,786
3%
$507,590
—
2016
$13,345
1%
$507,590
—
2015
$13,233
1%
$507,590
—
2014
$13,040
-3%
$507,590
-12%
2011
$13,487
—
$576,370
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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101 Old Grassy Hill Road, Woodbury, CT 06798 (MLS# 24135665) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 101 Old Grassy Hill Road is currently listed for $1,267,500 and was received on December 02, 2025. This property is listed by Deb Cody from our Newtown Office.Want to learn more about 101 Old Grassy Hill Road? Do you have questions about finding other Single Family real estate for sale in Woodbury? You can browse all Woodbury real estate or contact a Coldwell Banker agent to request more information.

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