Woodstock Hill
415 Route 169, Woodstock, CT 06281
Woodstock sits in Connecticut's Quiet Corner in northern Windham County, bordering Massachusetts. It's the second-largest town in Connecticut by land area, settled in 1686 by a group from Roxbury, Massachusetts, who first called it New Roxbury before renaming it Woodstock in 1690.
Most Woodstock addresses use 06281 (Woodstock); South Woodstock (06267) and Woodstock Valley (06282) are separate ZIP codes within town.
| Area | Zip code | Where it is |
|---|---|---|
| Woodstock Hill | 06281 | The town center, on Route 169, where Town Hall, the historic green and Roseland Cottage sit. |
| South Woodstock | 06267 | South of the center along Route 169, near the Woodstock Fairgrounds. |
| Woodstock Valley | 06282 | The western part of town, near the Union town line. |
Woodstock covers about 61.8 square miles and borders Union, Ashford, Pomfret and Thompson. It was incorporated in 1690.
Start with Roseland Cottage and Roseland Park, then 2 more below.
A pink 1846 Gothic Revival summer home built by businessman Henry C. Bowen, with 21 formal gardens and the country's oldest surviving indoor bowling alley in its carriage barn. Ulysses S. Grant bowled there while a sitting president. Run by Historic New England and open for seasonal tours.
556 Route 169, Woodstock, CT 06281
Plan a visitA 60-acre town park on Roseland Lake that Bowen gave to the community, with a playground, pavilion, basketball court, boat launch, swimming and fishing. Bowen hosted Fourth of July celebrations here that drew up to 10,000 people and several sitting U.S. presidents.
205 Roseland Park Rd, Woodstock, CT 06281
Plan a visitA working winery and brewery on the CT Wine Trail offering tastings and tours.
848 Bailey Hill Rd, Pomfret Center area / Woodstock, CT
Plan a visitHome of the Woodstock Fair, run by the Woodstock Agricultural Society since 1846 and held annually since 1860.
281 Route 171, Woodstock, CT 06281
A group of 13 men from Roxbury, Massachusetts, settled the area in 1686 and called it New Roxbury; the town was renamed Woodstock in 1690 and became part of Connecticut in 1749.
Businessman Henry C. Bowen, a Woodstock native, built the Roseland Cottage summer home in 1846 and hosted Fourth of July celebrations there attended by Presidents Grant, Hayes and Harrison.
The Woodstock Fair has been held annually since 1860, run by the Woodstock Agricultural Society, founded in 1846.
Woodstock has more lake and park acreage than commercial development, with Roseland Park anchoring the town center and several smaller lakes elsewhere in town.
Woodstock is a rural, spread-out town; Woodstock Hill and South Woodstock have a walkable cluster of civic buildings and a few businesses, but most errands require a car.
415 Route 169, Woodstock, CT 06281
Approximate, without traffic.
No fixed-route bus service; the Northeastern Connecticut Transit District provides dial-a-ride service to Woodstock. There is no passenger rail station in town.
Woodstock's 2026–27 mill rate is 20.21, which is $20.21 of tax for every $1,000 of assessed value. Some areas also pay a fire or special district tax on top of that. Connecticut taxes a home at 70% of its appraised value, so every $100,000 of value costs about $1,415 a year in taxes at 20.21 mills.
| 12 months ending | Single-family | Condo |
|---|---|---|
| Sep 2024 | $390,000105 sales | $233,6989 sales |
| Sep 2025 | $477,50089 sales | $265,00011 sales |
October to September, state records. Text us for this month's sales.
20.21mills, fiscal year 2026–27
| Fiscal year | Town rate |
|---|---|
| 2022–23 | 20.85 |
| 2023–24 | 22.41 |
| 2024–25 | 23.04 |
| 2025–26 | 23.04 |
| 2026–27 | 20.21 |
Woodstock's town rate went from 20.85 in 2022–23 to 20.21 in 2026–27. Next revaluation: October 1, 2030.
What we check on a Woodstock purchase: CHFA limits, the flood map, crumbling foundations, private wells & septic and lake communities.
CHFA sets Woodstock's income and price limits for Windham County. We check them with you before you shop.
See CHFA's limits mapParts of Woodstock along the Muddy Brook and around Roseland, Bungee and Quasset lakes fall within FEMA-mapped flood zones; lakefront and low-lying parcels should be checked against the flood map before an offer. We check FEMA's map before you offer.
FEMA's flood map for WoodstockWoodstock is within the northeastern Connecticut area affected by pyrrhotite-related crumbling concrete foundations. Homes built or with foundations poured roughly between the 1980s and mid-2010s are the ones typically tested. We recommend a foundation inspection as part of due diligence on older homes.
CT Foundation Solutions Indemnity CompanyMost of Woodstock relies on private wells and septic systems rather than town water or sewer. Well and septic inspections are a standard part of a purchase here.
Homes around Lake Bungee, Quasset Lake and Roseland Lake may belong to a lake or homeowners' association with its own dues and rules; ask for the association documents before you make an offer.
All loans are subject to credit approval, underwriting, and property and program requirements. CHFA and USDA limits and eligibility are set by those agencies and change from time to time.
Send us a Woodstock address and we'll run the numbers, taxes included.
Who to call in Woodstock: Eversource for power.
49 Paine District Rd, Woodstock, CT Tuesday, Friday, Saturday, Sunday, 10:00 a.m.–3:45 p.m.
Annual permit sold at the Town Clerk's office during Town Hall hours
Transfer station detailsWoodstock Town Hall is at 415 Route 169, Woodstock, CT 06281. Hours: Monday, Tuesday, Thursday 8:30 a.m.–4:30 p.m.; Wednesday 8:30 a.m.–6:00 p.m.; closed Friday. Main line: (860) 928-6595. Each link opens that office's page on the town's website.
The short answers. Call or text us for the long ones.
Woodstock's 2026–27 mill rate is 20.21, which is $20.21 of tax for every $1,000 of assessed value. Some areas also pay a fire or special district tax on top of that. The motor vehicle rate is 20.21 mills.
Connecticut assesses homes at 70% of appraised value, so a $500,000 home would be assessed at about $350,000. At 20.21 mills that's about $7,074 a year, or about $589 a month, before any district tax. The actual bill depends on the town assessor's appraisal, not the price you pay.
In the 12 months from October 2024 through September 2025, the median single-family sale in Woodstock was $477,500 across 89 sales, compared with $390,000 the year before. The median condo sale was $265,000 across 11 sales.
Woodstock's next revaluation takes effect October 1, 2030, on the state's schedule. The new assessments first show up on the tax bills due in July 2031.
Woodstock is in Windham County, in Connecticut's Northeastern Connecticut Planning Region.
06281 (Woodstock/Woodstock Hill), 06267 (South Woodstock) and 06282 (Woodstock Valley).
No. Residents use the Woodstock Transfer & Recycling Center at 49 Paine District Road with an annual permit, or contract with a private hauler.
There's no fixed-route bus service; the Northeastern Connecticut Transit District offers dial-a-ride service in town. There is no passenger rail station.
Worcester, Massachusetts is about 28 miles away. Bradley International Airport is roughly 55 miles away.
Connecticut towns bill property taxes twice a year, generally due July 1 and January 1; check the Tax Collector's office for Woodstock's exact schedule.
Neighbors of Woodstock in Windham County and nearby. All Windham County towns.