Living in Woodstock, CT
Woodstock is a 60.68 square mile town in Windham County, in Connecticut's northeast corner, home to Roseland Cottage, Roseland Park and the annual Woodstock Fair.
Woodstock at a glance
- Median sale price
- $415,000−9.8% vs last year 111 sales, last 12 months
- Property tax rate
- 20.21 mills town-wide, FY2027
- Estimated yearly tax
- ~$5,900 median-priced home
- Population
- 8,434 2024 Census estimate
- Land area
- 60.7 sq mi 139 per sq mi
What it is like in Woodstock
Woodstock covers 60.68 square miles in Windham County and had a population of 8,434. It borders Eastford, Pomfret, Union, Thompson and Putnam, and lies in the northeast part of the state often called the Quiet Corner.
Massachusetts bought the land that includes Woodstock from the Mohegans in 1682, and it later passed to Connecticut. Henry C. Bowen, born in Woodstock in 1813, built Roseland Cottage in 1846. It is a Gothic Revival National Historic Landmark owned by Historic New England.
Village centers include Woodstock Hill, South Woodstock and the Little River Plaza area on Route 171.
Roseland Park is a 500-acre park and lake with playgrounds, picnic sites, fishing and a nine-hole golf course. Town and nearby places include Woodstock Town Beach, Beeches Recreation Park, Town Commons, Black Pond Boat Launch, the Little River Greenway, Williams Preserve, Harvey Preserve, Rocky Hill Refuge and Goodell Morse Memorial Forest. Harrisville and Woodstock golf courses are also in town.
The Woodstock Fair has been held every Labor Day weekend since 1859. Roseland Cottage offers guided tours, and the Recreation Commission runs free summer concerts with it. Dining includes The Mansion at Bald Hill and Woodstock Tavern.
Getting around from Woodstock
| Drive to | Time | Miles |
|---|---|---|
| Hartford | 60 min | 42 |
| New Haven | 102 min | 78 |
| Stamford | 155 min | 116 |
| New York City (Midtown) | 208 min | 151 |
| Boston | 96 min | 67 |
| Providence | 62 min | 37 |
| Bradley Airport (BDL) | 75 min | 51 |
Rail
No passenger rail station within 8 miles.
Highways and routes
The facts file lists no rail station for Woodstock. By car, Hartford is 60 minutes (42 miles), Providence 62 minutes (37 miles), Boston 96 minutes (67 miles), New Haven 102 minutes (78 miles) and New York City (Midtown) 208 minutes (151 miles).
Bradley Airport is 75 minutes (51 miles) away. Route 169 runs through Woodstock Hill and South Woodstock, and Route 171 passes Little River Plaza.
Schools in Woodstock
3 public schools in Woodstock School District and The Woodstock Academy District. Which one serves an address depends on the district, so confirm with them.
Elementary 1
- Woodstock
Middle 1
- Woodstock
High school 1
- The Woodstock Academy
Grades, number of students. Hover a school for its address.
For report cards, enrollment trends and spending per student, look up Woodstock School District and The Woodstock Academy District on the state's EdSight site.
Source: National Center for Education Statistics, Common Core of Data. We do not rate or rank schools.
Eat, drink and explore in Woodstock
Open Woodstock in Google Maps →Eat and drink 5
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Farm brewery and taproom on a 44-acre farm, down the hill from the winery.
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Winery and vineyard with a tasting room on a 44-acre farm.
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Dinner restaurant in a historic house that also runs a bed and breakfast and hosts events.
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Farm brewery and orchard on a 100-acre property; visits follow the brewery's reservation rules.
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Tavern in Little River Plaza serving Greek and Mediterranean dishes, with a full bar and live entertainment.
Things to do and see 2
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Gothic Revival summer house built in 1846 and run by Historic New England, with guided tours and a gift shop.
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Orchard with a farm store and bakery, plus pick-your-own apples and blueberries in season.
Parks, preserves and trails 26
Show 12 more parks and conservation parcels
Parks and open space © OpenStreetMap contributors. Places to eat and visit last checked October 2026. These are not paid placements; they are simply our selection. Hours and menus change, so check before you go.
Woodstock housing market
Over the last 12 months, 111 homes sold in Woodstock with a median sale price of $415,000 and a median of 12 days on market. There are 20 homes for sale right now.
Homes sold for a median of $259 per square foot. The typical home sold for 100% of its list price, and the median sale price is down 9.8% from the year before. At the current pace of sales, the homes for sale would last about 2.2 months.
Woodstock's town-wide property tax rate is 20.21 mills (FY2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $5,900 a year. Special taxing districts, such as fire districts, can add to this, and a home's actual assessment may differ from its sale price.
Source: SmartMLS, residential sales (single-family, condo and multi-family); mill rates: Connecticut Office of Policy and Management. Updated November 10, 2026.
Homes for sale in Woodstock
See all 20 →
Know before you move
Official and independent sources worth bookmarking if you are considering Woodstock.
Questions about Woodstock
What is the median home price in Woodstock, CT?
The median sale price in Woodstock is $415,000, based on 111 home sales in the last 12 months (SmartMLS). Updated November 10, 2026.
What is the property tax rate in Woodstock, CT?
Woodstock's town-wide property tax rate is 20.21 mills (fiscal year 2027). Connecticut assesses homes at 70% of market value, so a median-priced home pays roughly $5,900 a year. Special taxing districts can add to this.
How far is Woodstock, CT from Hartford?
Woodstock is about 42 miles and a 60-minute drive from downtown Hartford, measured from the town center without traffic.
How far is Woodstock, CT from New York City?
Woodstock is about 151 miles from Midtown Manhattan, roughly a 208-minute drive without traffic.
What is the population of Woodstock, CT?
Woodstock has about 8,434 residents (U.S. Census Bureau estimate, 2024) and covers 60.7 square miles.
How many public schools are in Woodstock, CT?
Woodstock has 3 public schools in Woodstock School District and The Woodstock Academy District. Which school serves an address depends on the district's boundaries, so confirm with the district.
How many homes are for sale in Woodstock, CT?
There are 20 homes for sale in Woodstock right now, per SmartMLS, as of November 10, 2026.
What is there to see in Woodstock?
Roseland Cottage, a National Historic Landmark from 1846, Roseland Park, the Woodstock Fair in September, and preserves such as Williams Preserve and Goodell Morse Memorial Forest.
When is the Woodstock Fair?
It runs from the Thursday before Labor Day through Labor Day Monday. The fairground site lists Sept. 2 to 6, 2027 for the next fair.
How far is Woodstock from Hartford and Providence?
Hartford is 60 minutes and 42 miles by car. Providence is 62 minutes and 37 miles.
Which towns border Woodstock?
Eastford, Pomfret, Union, Thompson and Putnam.
Is there a rail station in Woodstock?
No station is listed for the town in our data.
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