101 Old Grassy Hill Rd

Woodbury, CT 06798

$1,267,500
Price
4
Beds
4,676 Sq. Ft.
$271 / Sq. Ft.
4,676
Sq. Ft.
$271
per Sq. Ft.
Under Contract
Under Contract
Back walkway

Description

"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..."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.

Property Details for 101 Old Grassy Hill Road

Basement Description
Full, Heated, Garage Access, Interior Access, Partially Finished, Walk-out, Full With Walk-Out
Direct Waterfront
Yes
Expected Active Date
12-16-2025
Garages Number
5
Neighborhood
Grassy Hill
Style
Colonial, Contemporary
Garage Parking Info
Attached Garage, Under House Garage
Swimming Pool
No
LISTING UPDATED: 12/23/2025 01:56 AM

Property Details for 101 Old Grassy Hill Road

StatusUnder Contract
MLS #24135665
Days on Market6
Taxes$14,628 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2004
Lot Size5.17 AC / 225,205 SF
CountyLitchfield County

Location

Listing Courtesy of Coldwell Banker Realty, Deb Cody; Coldwell Banker Realty, Meli Garthwait
Add your commute

Building Information for 101 Old Grassy Hill Road

Stories-Year Built2004Building Size-Lot Size5.17 AC / 225,205 SF

Payment Calculator

$7,482 per month

30 year fixed, 6.28% Interest

Principal and Interest

$6,263

Property Taxes

$1,219

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 101 Old Grassy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Main Street South(Rt6) onto Rt317. Old Grassy Hill Road on left. End of the Cul de Sac on left hand side.
  • Elementary School: Per Board of Ed
  • Flood Zone: No
  • High School: Nonnewaug
  • Latitude: 41.533259
  • Longitude: -73.232157
  • Neighborhood Amenities: Basketball Court, Health Club, Library, Park, Stables/Riding
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $14,628
Interior and Exterior Features
Exterior Features
  • Exterior Features: Underground Utilities, Shed, Porch, Deck, Gutters, Hot Tub, Stone Wall, Patio
  • Waterfront Description: Pond, Lake, Walk to Water, View
Interior Features
  • Appliances Included: Gas Cooktop, Range Hood, Refrigerator, Dishwasher, Washer
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Hydro Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 1
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: New renovated laundry room
  • Rooms Additional: Foyer, Laundry Room, Workshop
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 14.0
Room 2
  • Room Entry Order: 10
  • Room Features: Built-Ins,Walk-In Closet,Wall/Wall Carpet
  • Room Length: 18.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 16.0
Room 3
  • Room Entry Order: 2
  • Room Features: Palladian Window(s),Gas Log Fireplace,Hardwood Floor
  • Room Length: 22.0
  • Room Level: Main
  • Room Type: Great Room
  • Room Width: 21.0
Room 4
  • Room Entry Order: 3
  • Room Features: Built-Ins,Ceiling Fan,Full Bath,Wall/Wall Carpet
  • Room Length: 24.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 15.0
Room 5
  • Listing Key: 41DA8633C9847015E063E201100AA8D2
  • Room Entry Order: 4
  • Room Features: Bay/Bow Window,9 ft+ Ceilings,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Formal Dining Room
  • Room Width: 14.0
Room 6
  • Room Entry Order: 5
  • Room Features: Breakfast Nook,Granite Counters,Island,Pantry,Sliders,Hardwood Floor
  • Room Length: 45.0
  • Room Level: Main
  • Room Type: Eat-In Kitchen
  • Room Width: 33.0
Room 7
  • Room Entry Order: 6
  • Room Features: 9 ft+ Ceilings,Ceiling Fan,Full Bath,Hydro-Tub,Walk-In Closet,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 16.0
Room 8
  • Room Entry Order: 7
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Length: 20.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 19.0
Room 9
  • Listing Key: 41DA8633C9847015E063E201100AA8D2
  • Room Entry Order: 8
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 10
  • Room Entry Order: 9
  • Room Features: Ceiling Fan,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 11.0
Property
Property and Assessments
  • Color: Moss
  • Construction Description: Frame
  • Exclusions: Shed,portable generator,shed lawncare equipment,gar. refrigerator & shelving,some furnishings/decor items,home theater equip. & screen,gas grill negot
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Concrete
  • Fuel Tank Location: In Ground
  • Handicap Features: 32" Minimum Door Widths, Bath Grab Bars, Hallways 36+ Inches Wide, Multiple Entries/Exits
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2004
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • In Law Access: Lower Level, Separate Entry
  • In Law Apartment: Possible
  • Sq Ft Description: Theater room, office/ in law/ bedroom 700 sq ft
  • Sq Ft Est Heated Below Grade: 700
  • Living Area SQFT Per Public Records: 3976
Lot Information
  • Lot Description: Secluded, Lightly Wooded, On Cul-De-Sac, Professionally Landscaped, Water View
  • Parcel Number: 934419
  • Sq Ft Est Heated Above Grade: 3976.0
  • Sq Ft Total: 4676.0
  • Zoning: OS80
Utilities
  • Energy Features: Fireplace Insert, Ridge Vents, Thermopane Windows
  • Heat Fuel Type: Propane
  • Hot Water Description: 80 Gallon Tank
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: No
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 101 Old Grassy Hill Road

DateEvent & SourcePriceAppreciation
Jul 19, 2019

Closed (Public Record)

Public Record #649934425

$616,000

+8.1% / yr

Mar 4, 2004

Closed (Public Record)

Public Record #132759301

$185,000

+14.5% / yr

Aug 28, 2003

Closed (Public Record)

Public Record #127050288

$172,500—
DateEvent & SourcePrice
07/19/2019

Closed (Public Record)

Public Record #649934425

$616,000

+8.1% / yr

03/04/2004

Closed (Public Record)

Public Record #132759301

$185,000

+14.5% / yr

08/28/2003

Closed (Public Record)

Public Record #127050288

$172,500

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

Public Records for 101 Old Grassy Hill Road

Taxable ValueLand$122,010Additions$497,280Total$619,290
Tax Record2024$14,628 ($1,219 / month)
Home Facts
Beds4Baths4Total Finished SqFt3,976 SqFtAbove Grade Finished SqFt3,976 SqFtUnfinished Basement SqFt1,918 SqFtStories2Lot Size225,205 SqFtStyleSingle Family ResidenceYear Built2004Year Renovated2016ZoningOS80CountyLITCHFIELDAPNWOOD M:050 B:053A L:10Fireplace TypeHas Fireplace

Schools near 101 Old 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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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 makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty, Deb Cody; Coldwell Banker Realty, Meli Garthwait

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.