Date
Details
Price
Change
Source
4/04/2026
Listed
$759,900
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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Property Description
Recently renovated from the studs up, this single-family ranch on the Woodbury/Roxbury town line offers the rare chance to own a truly like-new home with immediate availability. This three-bedroom home features all-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, a beautifully updated kitchen, and three brand-new bathrooms. The main level offers a spacious layout with three bedrooms featuring wide pine flooring, two full tiled baths, a living room with a fireplace, and a stunning new eat-in kitchen. The finished walkout lower level adds approximately 800 square feet of versatile living space. This space is ideally suited for an in-law apartment, with a family room and fireplace, a full bath, space for a kitchen, and a private entrance. Set on a gorgeous 2+ acre lot at the top of Woodbury, the property also includes a small portion in Roxbury.
Full Property Details
Full Property Details for 220 Upper Grassy Hill Rd
General
- Price: $759,900
- Taxes: (July 2025-June 2026)
- Status: Active
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24163591
- Updated: Today (4/4/2026)
- Added to Site: Today
Interior
- Number of Rooms: 7
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Gas Range, Microwave, Refrigerator, Dishwasher
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 3
Bedrooms
- Total Bedrooms: 3
- Primary Bedroom: Primary Bedroom - Full Bath, Hardwood Floor, Main
- Bedroom 1: Bedroom - Hardwood Floor, Main
- Bedroom 2: Bedroom - Wide Board Floor, Main
Other Rooms
- Living Room: Living Room - Built-Ins, Combination Liv/Din Rm, Fireplace, Wide Board Floor, Main
- Family Room: Family Room - Fireplace, Engineered Wood Floor, Vinyl Floor, Lower
- Kitchen: Kitchen - Remodeled, Eating Space, Main
- Dining Room: Dining Room - Combination Liv/Din Rm, Hardwood Floor, Main
- Game room: Yes
- Game Room: Rec/Play Room - Engineered Wood Floor, Vinyl Floor, Lower
- Rec Room: Engineered Wood Floor, Vinyl Floor, Lower
- Laundry: Lower Level, Main Level
Exterior
- Exterior Features: Sidewalk, Shed, Barn, Patio
- Color: Brick
Parking
- Garage: Yes
- Garage Spaces: 1
- Parking: Detached Garage
Location
- County: Litchfield
- Neighborhood: Grassy Hill
- Driving Directions: Rt 317 to Upper Grassy Hill Road
School Information
- Elementary School: Mitchell
- Middle School: Woodbury
- High School: Nonnewaug
Community
- Community Name: Grassy Hill
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Hot Air, Wall Unit, Electric, Propane
- Heating Fuel: Electric, Propane
- Water Heater: Other
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Ranch
- Description/Design: Horse Property
- Construction Status: No/Resale
- Exterior Const.: Brick
- Basement Desc.: Full, Heated, Cooled, Partially Finished, Walk-out, Liveable Space, Full With Walk-Out
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 2,420
- Above Ground: 1,620 Sq. Ft.
- Below Ground: 800 Sq. Ft.
- Year Built: 1960
Lot Features
- Lot Size (Acres): 2.45
- Zoning: OS80
- Lot Description: Lightly Wooded, Level Lot
Horse Property
- Horse Property: Yes
Financial Considerations
- Assessment Amount: $251,300
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 934850
Listed by Drakeley Real Estate, Inc., Timothy Drakeley
We Value Your Privacy
We Value Your Privacy
We Value Your Privacy
Listing agent
— 220 Upper Grassy Hill Rd —
Timothy Drakeley
Drakeley Real Estate, Inc.
Agent Contact: (203) 510-9184 Office Contact: (203) 263-4336
NMLS#: 1598647Get Pre-Approved Today
Schools
Schools serving 220 Upper Grassy Hill Rd
School District:Regional School District 14
| Name | Grades | Distance |
|---|---|---|
Mitchell Elementary School 14 School Street, Woodbury, CT 06798 | PK-5 | 2.6 mi |
Woodbury Middle School 67 Washington Avenue, Woodbury, CT 06798 | 6-8 | 2.4 mi |
Nonnewaug High School 5 Minortown Road, Woodbury, CT 06798 | 9-12 | 3.6 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 220 Upper Grassy Hill Rd
Tax History
Tax History for 220 Upper Grassy Hill Rd
Year
Property Taxes
Change
Tax Assessment
Change
2025
$5,936
2%
$251,300
—
2023
$5,823
7%
$251,300
35%
2023
$5,419
—
$186,490
—
2022
$5,440
—
$186,490
—
2021
$5,440
—
$186,490
—
2020
$5,440
—
$186,490
—
2019
$5,440
1%
$186,490
-8%
2018
$5,384
-2%
$202,560
—
2017
$5,502
3%
$202,560
—
2016
$5,325
1%
$202,560
—
2015
$5,281
1%
$202,560
—
2014
$5,204
-4%
$202,560
-12%
2011
$5,405
—
$230,990
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
Estimate the Cost
Estimate the Cost for 220 Upper Grassy Hill Rd
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- Single Family
- Active
- Updated 5 days ago
- 3Beds
- 2Total Baths
- 1,862Sq. Ft.
- Single Family
- Active
- Updated 3 days ago
- 4Beds
- 2Total Baths
- 2,008Sq. Ft.
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- Condo
- Active
- Updated 1 day ago
- 2Beds
- 2Total Baths
- 1,032Sq. Ft.
- Condo
- Active
- Updated 6 hours ago
- 2Beds
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- 1,398Sq. Ft.
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- Condo
- Active
- Updated 5 days ago
- 2Beds
- 2Total Baths
- 1,144Sq. Ft.
Listed by Doug Collins (203) 482-7167
- Condo
- Active
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- Condo
- Active
- Updated 4 days ago
- 2Beds
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- 1,432Sq. Ft.
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220 Upper Grassy Hill Road, Woodbury, CT 06798 (MLS# 24163591) is a Single Family property with 3 bedrooms and 3 full bathrooms. 220 Upper Grassy Hill Road is currently listed for $759,900 and was received on April 04, 2026. Want to learn more about 220 Upper 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.