$3,600
Total Monthly Price
220 Upper Grassy Hill Rd
Woodbury, CT 06798
Today
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475-281-3909
-
Bedrooms
3
-
Bathrooms
3
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Square Feet
1,620 sq ft
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Available
Available Now
Highlights
- Ranch Style House
- Attic
- 2 Fireplaces
- Thermal Windows
- Storm Windows
- Patio
220 Upper Grassy Hill Rd
Favorites
About This Home
Available Now
Recently renovated single-family home on the Woodbury/Roxbury town line. Completely rebuilt from the studs up, this three-bedroom ranch features brand-new electrical, HVAC, spray-foam insulation, trim, drywall, hardwood floors, plus a new kitchen and three new baths. Rare opportunity to rent a truly "like-new" home available immediately. Enjoy a spacious main level with three bedrooms, a living room with fireplace, and an eat-in kitchen-plus a fully finished, full walkout lower level with a family room and fireplace and a full bath, ideal for an in-law setup or flexible bonus space.
220 Upper Grassy Hill Rd is a house located in Litchfield County and the 06798 ZIP Code. This area is served by the Regional School District 14 attendance zone.
* Price shown is total price based on community-supplied monthly required fees. Excludes user-selected optional fees and variable or usage-based fees and required charges due at or prior to move-in or at move-out. Price, availability, fees, and any applicable rent special are subject to change without notice.
* Square footage definitions vary. Displayed square footage is approximate.
Home Details
Year Built
Built in 1960
Attic
Pull Down Stairs to Attic
Bedrooms and Bathrooms
3 Full Bathrooms
3 Bedrooms
Home Design
Ranch Style House
Masonry Siding
Home Security
Storm Windows
Interior Spaces
2 Fireplaces
Thermal Windows
2,320 Sq Ft Home
Kitchen
Gas Cooktop
Dishwasher
Laundry
Laundry on lower level
Listing and Financial Details
Assessor Parcel Number 934850
Location
Property is near golf course
Lot Details
2.45 Acre Lot
Property is zoned OS80
Outdoor Features
Patio
Parking
1 Car Garage
Partially Finished Basement
Heated Basement
Walk-Out Basement
Basement Fills Entire Space Under The House
Schools
Mitchell Elementary School
Woodbury Middle School
Nonnewaug High School
Utilities
Central Air
Private Company Owned Well
Heating System Uses Oil Above Ground
Wall Furnace
Heating System Mounted To A Wall or Window
Heating System Uses Propane
Community Details
Pet Policy
Pets Allowed with Restrictions
Location
Get Directions
Amenities
- Washer/Dryer
- Air Conditioning
- Heating
- Fireplace
- Dishwasher
- Kitchen
- Range
- Refrigerator
- Basement
- Attic
Education
| Colleges & Universities | Distance | ||
|---|---|---|---|
| Colleges & Universities | Distance | ||
| Drive: | 27 min | 14.7 mi | |
| Drive: | 30 min | 17.5 mi | |
| Drive: | 36 min | 21.1 mi | |
| Drive: | 40 min | 24.6 mi |
220 Upper Grassy Hill Rd is within 27 minutes or 14.7 miles from Post University. It is also near UCONN, Tri Campus, Waterbury and Western Connecticut, Midtown.
Schools
Public Elementary School
Grades PK-5
415 Students
Nearby
Public Middle School
Grades 6-8
303 Students
Attendance Zone
Public High School
Grades 9-12
676 Students
Attendance Zone
Private Elementary, Middle & High School
Grades K-12
1,562 Students
Nearby
School data provided by
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Data provided by GreatSchools.org © 2026. All rights reserved.
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
Data provided by GreatSchools.org © 2026. All rights reserved.
Getting Around
What do Walkability, Transit, Drivability, and Bikeability mean?
Walkability measures the walking distance to day-to-day needs.
Transit measures access to public transportation.
Drivability measures congestion, parking availability, and access to major roads.
Bikeability measures the suitability for cycling.
How It Works
Not Walkable
Walkability
10
/ 100
Exceptionally Drivable
Drivability
100
/ 100
Somewhat Bikeable
Bikeability
30
/ 100
Scores provided by
What do Walkability, Transit, Drivability, and Bikeability mean?
Walkability measures the walking distance to day-to-day needs.
Transit measures access to public transportation.
Drivability measures congestion, parking availability, and access to major roads.
Bikeability measures the suitability for cycling.
How It Works
-
Soundscore™
-
/ 100
Traffic
-Airport
-Businesses
-Scores provided by
HowLoud What is a Sound Score Rating? A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources. How It Works220 Upper Grassy Hill Rd Photos
About the Listing Agent
Tim Drakeley
Drakeley Real Estate, Inc.
Since 1991, Tim Drakeley has solidified his reputation as a premier broker and salesperson, consistently ranked as Woodbury, CT’s #1 selling and listing broker for 12 years and a top producer in the Tri-bury region and all of Litchfield County. A graduate of Holy Cross High School, Northfield Mount Hermon Prep School, and Babson College, where he studied Finance and Entrepreneurial Studies, Tim brings deep expertise to Drakeley Real Estate. Founded in 1986 by his mother, entrepreneur Joyce S. Drakeley, this family-owned firm has earned a 39-year legacy of trust and integrity, serving home buyers and sellers across Connecticut. As owner and broker since 2018, Tim, alongside Joyce and their dedicated team, builds enduring client and community relationships. Tim’s commitment to community shines through Drakeley Real Estate’s generous support for local nonprofits, including donations of time and resources to Flanders Nature Center, Southbury and Woodbury Woman’s Clubs, and numerous local sports organizations. A passionate community leader, Tim has coached Nonnewaug High School’s Boys Varsity Basketball for over 25 years and currently leads the 7th-grade girls’ travel basketball team through Woodbury Park and Recreation. He serves as President of the Nonnewaug Athletic Club, a nonprofit supported by Drakeley Real Estate, and as President of Highfield Country Club. Together with his wife, Shelley, Tim has restored numerous Woodbury homes and owns Tim Drakeley Old Barns and Drakeley Construction. ”When you work with us, your house is not just a sale or a number; our partnership is a lifelong connection” a Drakeley motto that the family thrives to deliver on. Whether it’s helping you find your right home or prioritizing finding ways to give back to the Woodbury community, Drakeley Real Estate is committed to their mission.
MLS Number: 77000
What Are Walk Score®, Transit Score®, and Bike Score® Ratings?
Walk Score® measures the walkability of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
What is a Sound Score Rating?
A Sound Score Rating aggregates noise caused by vehicle traffic, airplane traffic and local sources.
220 Upper Grassy Hill Rd
Woodbury, CT 06798