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$759,900
New Listing

220 Upper Grassy Hill Road
Woodbury, CT 06798

For Sale|Single Family Residence|Active
3
Beds
3
Total Baths
3
Full Baths
1,620
SqFt
$469
/SqFt
1960
Built
County:
Litchfield
Listing courtesy of Timothy Drakeley of Drakeley Real Estate, Inc. Office Phone: (203) 263-4336 Broker Contact: (203) 510-9184

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220 Upper Grassy Hill Road220 Upper Grassy Hill Road220 Upper Grassy Hill Road220 Upper Grassy Hill Road
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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.

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Listing Snapshot
Price 
$759,900
Days On Site 
0 Days
Bedrooms 
3
Inside Area (SqFt) 
1,620 sqft
Total Baths 
3
Full Baths 
3
Partial Baths 
N/A
Lot Size 
2.45 Acres
Year Built 
1960
MLS® Number 
24163591
Status 
Active
Property Tax 
$5,936
HOA/Condo/Coop Fees 
N/A
Sq Ft Source 
N/A
Friends & Family
Recent Activity
21 hours agoListing updated with changes from the MLS®
21 hours agoListing first seen on site
General Features
Acres 
2.45
Foundation 
BlockConcrete Perimeter
Garage 
Yes
Garage Spaces 
1
Property Sub Type 
Single Family Residence
Sewer 
Septic Tank
SqFt Total 
2420
Style 
Ranch
Water Source 
Well
Zoning 
OS80
Interior Features
Appliances 
DishwasherGas RangeMicrowaveRefrigerator
Basement 
FullPartially FinishedWalk-Out Access
Cooling 
Central Air
Fireplace 
Yes
Fireplaces 
2
Heating 
ElectricPropaneForced Air
Laundry Features 
Main Level
Dining Room 
Level – Main
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Exterior Features
Construction Details 
BrickFrame
Lot Features 
Level
Other Structures 
Barn(s)Shed(s)
Patio And Porch 
Patio
Roof 
Asphalt
Community Features
Community Features 
Golf
Horse Allowed 
Yes
Schools
School District
Unknown
Elementary School
Mitchell
Middle School
Woodbury
High School
Nonnewaug
Listing courtesy of Timothy Drakeley of Drakeley Real Estate, Inc. Office Phone: (203) 263-4336 Broker Contact: (203) 510-9184



The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.
Last checked: 2026-04-05 03:53 PM UTC.

Neighborhood & Commute
Source: Walkscore
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