"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. With separate entrance living quarters, a five car garage, and top-of-the-line mechanicals and kitchen appliances, this home is as practical as it is poetic. Whether hosting an intimate gathering or a grand celebration for 200, the space adapts effortlessly. Dare to be happy. This is more than a home-it's a lifestyle, a retreat, a masterpiece.
Sold for $1,200,000
$1,200,000
101 Old Grassy Hill Road, Woodbury, CT 06798
4beds
4,676sqft
Single Family Residence
Built in 2004
5.17 Acres Lot
$1,221,200 Zestimate®
$257/sqft
$6,204 Estimated rent
Home value
$1,221,200
$1.04M - $1.43M
$6,204/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Deb Cody (203)228-0539,
Coldwell Banker Realty 203-426-5679,
Meli Garthwait 203-917-5400,
Coldwell Banker Realty
Bought with:
Beth Hawley, REB.0756592
Berkshire Hathaway NE Prop.
Source: Smart MLS,MLS#: 24135665
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: High Ceilings, Ceiling Fan(s), Full Bath, Hydro-Tub, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 288 Square Feet
- Dimensions: 16 x 18
Bedroom
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Upper
- Area: 380 Square Feet
- Dimensions: 19 x 20
Bedroom
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Upper
- Area: 196 Square Feet
- Dimensions: 14 x 14
Bedroom
- Features: Ceiling Fan(s), Hardwood Floor
- Level: Upper
- Area: 165 Square Feet
- Dimensions: 11 x 15
Dining room
- Features: Bay/Bow Window, High Ceilings, Hardwood Floor
- Level: Main
- Area: 224 Square Feet
- Dimensions: 14 x 16
Great room
- Features: Palladian Window(s), Gas Log Fireplace, Hardwood Floor
- Level: Main
- Area: 462 Square Feet
- Dimensions: 21 x 22
Kitchen
- Features: Breakfast Nook, Granite Counters, Kitchen Island, Pantry, Sliders, Hardwood Floor
- Level: Main
- Area: 1485 Square Feet
- Dimensions: 33 x 45
Living room
- Features: Hardwood Floor
- Level: Main
- Area: 210 Square Feet
- Dimensions: 14 x 15
Media room
- Features: Built-in Features, Walk-In Closet(s), Wall/Wall Carpet
- Level: Lower
- Area: 288 Square Feet
- Dimensions: 16 x 18
Office
- Features: Built-in Features, Ceiling Fan(s), Full Bath, Wall/Wall Carpet
- Level: Main
- Area: 360 Square Feet
- Dimensions: 15 x 24
Heating
- Forced Air, Hydro Air, Zoned, Propane
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Cooktop, Range Hood, Refrigerator, Dishwasher, Washer, Water Heater
- Laundry: Upper Level
Features
- Sound System, Open Floorplan, Entrance Foyer
- Windows: Thermopane Windows
- Basement: Full,Heated,Garage Access,Interior Entry,Partially Finished,Walk-Out Access
- Attic: Storage,Pull Down Stairs
- Number of fireplaces: 1
- Fireplace features: Insert
Interior area
- Total structure area: 4,676
- Total interior livable area: 4,676 sqft
- Finished area above ground: 3,976
- Finished area below ground: 700
Property
Parking
- Total spaces: 5
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 5
Accessibility
- Accessibility features: 32" Minimum Door Widths, Bath Grab Bars, Accessible Hallway(s), Multiple Entries/Exits
Features
- Patio & porch: Porch, Deck, Patio
- Exterior features: Rain Gutters, Stone Wall
- Spa features: Heated
- Has view: Yes
- View description: Water
- Has water view: Yes
- Water view: Water
- Waterfront features: Waterfront, Pond, Lake, Walk to Water
Lot
- Size: 5.17 Acres
- Features: Secluded, Few Trees, Cul-De-Sac, Landscaped
Details
- Additional structures: Shed(s)
- Parcel number: 934419
- Zoning: OS80
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: 2004
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
- Utilities for property: Underground Utilities, Cable Available
Green energy
- Energy efficient items: Ridge Vents, Windows
Community & neighborhood
Security
- Security features: Security System
Community
- Community features: Basketball Court, Health Club, Library, Park, Stables/Riding
Location
- Region: Woodbury
- Subdivision: Grassy Hill
Price history
| Date | Event | Price |
|---|---|---|
| 2/9/2026 | Sold | $1,200,000-5.3%$257/sqft |
Source:  Smart MLS #24135665 Report a problem | ||
| 12/23/2025 | Pending sale | $1,267,500$271/sqft |
Source: Smart MLS #24135665 Report a problem | ||
| 12/16/2025 | Listed for sale | $1,267,500+105.8%$271/sqft |
Source: Smart MLS #24135665 Report a problem | ||
| 7/24/2019 | Sold | $616,000-1.4%$132/sqft |
Source: Smart MLS #170188467 Report a problem | ||
| 4/28/2019 | Listed for sale | $624,900-13.8%$134/sqft |
Source: Coldwell Banker Residential Brokerage #170188467 Report a problem | ||
| 6/17/2018 | Listing removed | $725,000$155/sqft |
Source: Klemm Real Estate Inc #L10230398 Report a problem | ||
| 11/3/2017 | Price change | $725,000+3.7%$155/sqft |
Source: Klemm Real Estate Inc #L10230398 Report a problem | ||
| 6/16/2017 | Listed for sale | $699,000+277.8%$149/sqft |
Source: Klemm Real Estate Inc #L10230398 Report a problem | ||
| 3/2/2004 | Sold | $185,000+7.2%$40/sqft |
Source: Smart MLS #W1015723 Report a problem | ||
| 8/28/2003 | Sold | $172,500$37/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,628 +1.9% | $619,290 |
| 2024 | $14,349 +10.3% | $619,290 +38.3% |
| 2023 | $13,009 -0.4% | $447,660 |
| 2022 | $13,058 | $447,660 |
| 2021 | $13,058 | $447,660 |
| 2020 | $13,058 | $447,660 |
| 2019 | $13,058 -3.2% | $447,660 -11.8% |
| 2018 | $13,492 -2.1% | $507,590 |
| 2017 | $13,786 +3.3% | $507,590 |
| 2016 | $13,345 +0.8% | $507,590 |
| 2015 | $13,233 +1.5% | $507,590 |
| 2014 | $13,040 -3.3% | $507,590 -11.9% |
| 2013 | $13,487 -3.4% | $576,370 |
| 2012 | $13,965 +7.9% | $576,370 |
| 2011 | $12,945 +4.7% | $576,370 |
| 2010 | $12,363 +1.5% | $576,370 |
| 2009 | $12,179 +5.7% | $576,370 +21.8% |
| 2008 | $11,520 +1.6% | $473,120 |
| 2007 | $11,336 +5.1% | $473,120 |
| 2006 | $10,782 +6.4% | $473,120 |
| 2005 | $10,134 +355.3% | $473,120 +355.2% |
| 2004 | $2,226 +73.6% | $103,940 +121% |
| 2003 | $1,282 -9.1% | $47,030 -35.1% |
| 1997 | $1,410 | $72,510 |
Find assessor info on the county website
Neighborhood: 06798
Nearby schools
GreatSchools rating
- 5/10Mitchell Elementary SchoolGrades: PK-5Distance: 1.6 mi
- 6/10Woodbury Middle SchoolGrades: 6-8Distance: 1.5 mi
- 9/10Nonnewaug High SchoolGrades: 9-12Distance: 2.7 mi
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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- Connecticut
- Litchfield County
- Woodbury
- 06798
- 101 Old Grassy Hill Road
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