$2,200 / Month
100 Main St S
Woodbury, CT 06798
Today
Favorites
203-442-9453
-
Bedrooms
1
-
Bathrooms
1
-
Square Feet
800 sq ft
-
Available
Available Now
Highlights
- Colonial Architecture
- Covered Deck
- Attic
- 1 Fireplace
- End Unit
- Porch
100 Main St S
Favorites
About This Home
Available Now
Charming In-Town Apartment in a Classic Vintage Home Nestled in the heart of Woodbury, this delightful second-floor apartment offers both comfort and character, just moments from all the town's shops, restaurants, and amenities. Set within a beautifully maintained vintage home, the residence features wideboard hardwood floors throughout and a cozy living room complete with a wood-burning fireplace. The apartment includes a generously sized bedroom, a separate study perfect for remote work or reading, and a charming eat-in kitchen with exposed beams and a vaulted ceiling that adds warmth and visual appeal. Enjoy outdoor living with a private screened porch ideal for summer evenings, a secluded back deck, and convenient level parking just outside. A rare opportunity for in-town living with classic charm and peaceful outdoor spaces.
100 Main St S 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 base rent and may not include non-optional fees and utilities.
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 1750
Attic
Walkup Attic
Storage In Attic
Bedrooms and Bathrooms
1 Full Bathroom
1 Bedroom
Home Design
Colonial Architecture
Clap Board Siding
Interior Spaces
1 Fireplace
Ceiling Fan
800 Sq Ft Home
Kitchen
Cooktop
Laundry
Dryer
Laundry on main level
Washer
Lot Details
0.4 Acre Lot
End Unit
Level Lot
Property is zoned MSD
Outdoor Features
Covered Deck
Porch
Breezeway
Parking
Parking Deck
2 Parking Spaces
Schools
Nonnewaug High School
Unfinished Basement
Basement Fills Entire Space Under The House
Utilities
Heat Pump System
Heating System Uses Natural Gas
Heating System Uses Oil Above Ground
Community Details
Overview
4 Units
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
Location
Get Directions
Amenities
- Washer/Dryer
- Heating
- Ceiling Fans
- Fireplace
- Kitchen
- Refrigerator
- Basement
- Attic
- Porch
- Deck
Education
| Colleges & Universities | Distance | ||
|---|---|---|---|
| Colleges & Universities | Distance | ||
| Drive: | 17 min | 10.0 mi | |
| Drive: | 21 min | 12.2 mi | |
| Drive: | 30 min | 21.2 mi | |
| Drive: | 34 min | 24.7 mi |
100 Main St S is within 17 minutes or 10.0 miles from Post University. It is also near UCONN, Tri Campus, Waterbury and Western Connecticut, Midtown.
Schools
Public Elementary School
Grades PK-5
347 Students
Attendance Zone
Public Elementary School
Grades PK-5
515 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 3-12
33 Students
Nearby
Private Elementary & Middle School
Grades PK-8
161 Students
Nearby
Private High School
Grades 9-12
179 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 © 2025. 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 © 2025. All rights reserved.
100 Main St S 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
100 Main St S
Woodbury, CT 06798