Every town in Windham County, with home values, population and local guides. Typical home value $377,000.
Reviewed and updated October 3, 2026 by Ryan and Megan Winslow, Winslow Homes
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Windham County is home to about 118,351 people across 512.7 square miles and 15 towns and cities with Winslow Homes guides. The largest are Windham, Killingly, Plainfield, Thompson. Median household income is $82,098 and 70% of households own their home.
Ryan and Megan compare every town in Windham County on price, taxes, schools and commute so you choose the right fit, then handle the loan through The Federal Savings Bank.
Tap any town for its full guide.
| Town | Typical value | 1 year | Residents |
|---|---|---|---|
| Windham | $333,000 | +2.5% | 24,105 |
| Killingly | $369,000 | +2.6% | 18,093 |
| Plainfield | $352,000 | +3.2% | 15,315 |
| Thompson | $395,000 | +7.2% | 9,513 |
| Putnam | $354,000 | +3.6% | 9,407 |
| Brooklyn | $418,000 | +8.1% | 8,708 |
| Woodstock | $449,000 | +2.9% | 8,434 |
| Canterbury | $417,000 | +5.9% | 5,222 |
| Pomfret | · | · | 4,355 |
| Ashford | $399,000 | +5.3% | 4,263 |
| Sterling | $402,000 | +4.0% | 3,694 |
| Chaplin | $371,000 | +7.8% | 2,179 |
| Hampton | $404,000 | +6.1% | 1,759 |
| Eastford | $416,000 | +6.5% | 1,706 |
| Scotland | $382,000 | +2.7% | 1,598 |
Windham County offers diverse real estate opportunities across Connecticut. The area features a mix of historic properties, new construction, and specialty homes. Buyers find options ranging from starter homes to luxury estates. The region attracts families, retirees, and investors drawn to the quality of life and strong property values. Local amenities, natural beauty, and community character make this one of Connecticut's notable real estate markets.
The Windham County real estate market spans a price range of $150K-$800K+. Single-family homes make up the largest segment, with condominiums and townhomes offering entry-level options. Waterfront and luxury properties command premium pricing. The market sees steady demand from both local move-up buyers and out-of-state relocators seeking the Connecticut lifestyle.
Winslow Homes serves Windham County buyers and sellers across FL, MA, CT, and RI. Ryan and Megan Winslow provide both brokerage and mortgage services (Ryan Winslow NMLS #2426605 | Megan Winslow NMLS #2692933). Get pre-approved at www.winslowloan.com or call 386-690-5858.
Windham County offers parks, trails, and outdoor activities year-round. Local and state parks provide hiking, fishing, and family recreation. Sports leagues and fitness facilities serve active residents.
Local galleries, theaters, and cultural events enrich the Windham County community. Seasonal festivals and farmers markets bring residents together. Historical societies preserve local heritage.
Windham County features a mix of local restaurants, regional chains, and specialty shops. Downtown areas offer walkable dining and retail. Farm-to-table options reflect the local agricultural heritage.
Annual events and seasonal celebrations create strong community bonds in Windham County. Holiday parades, summer concerts, and food festivals draw locals and visitors.
The heart of Windham County draws locals for dining, shopping, and community events. Walkable streets, local boutiques, and a mix of cuisines make it the social center.
Green spaces throughout Windham County offer trails, playgrounds, and sports facilities. Popular for morning runs, family outings, and weekend picnics.
Waterfront spots in Windham County attract boaters, fishers, and those seeking scenic views. Waterside dining and sunset walks are local favorites.
Single-family and multi-family rentals in Windham County generate steady cash flow. Cap rates range 5-8% depending on location and property condition. Screen tenants carefully and budget for maintenance.
Older properties in Windham County offer renovation potential. Target homes 20-30% below market value. Budget 15-20% of purchase price for renovations. Hold time of 3-6 months typical.
Long-term appreciation in Windham County has averaged 3-6% annually. Combined with mortgage paydown and tax benefits, buy-and-hold remains the most reliable wealth-building strategy.
The typical home in Windham County is worth $377,000, 16% below the Connecticut typical value of $451,000.
Zillow Home Value Index for Windham County, August 2026. The middle of the market for single family homes and condos.
Home values in Windham County moved +36.3% over five years and +101.1% over ten.
Median gross rent in Windham County. Useful for investors running rental numbers.
Share of occupied homes in Windham County lived in by the owner.
Older homes often need inspection focus on roof, systems and windows.
Median household income in Windham County.
Ryan and Megan are mortgage bankers with The Federal Savings Bank, lending in all 50 states. You get the home and the loan from one team. On a typical Windham County home of $377,000:
Ryan and Megan price Windham County homes from recent sales, not guesses. Send your address and you get a free market analysis, with no obligation.
Typical value $412,000 · 154,356 residents
Area guide →Typical value $433,000 · 271,289 residents
Area guide →Typical value $389,000 · 911,877 residents
Area guide →Typical value $465,000 · 167,398 residents
Area guide →Typical value $409,000 · 878,587 residents
Area guide →Typical value $428,000 · 188,143 residents
Area guide →The Zillow Home Value Index for Windham County was $377,000 in August 2026, +4.4% over the past year.
About 118,351 people as of 2024, based on the towns that make up the county.
Ashford, Brooklyn, Canterbury, Chaplin, Eastford, Hampton, Killingly, Plainfield, Pomfret, Putnam, Scotland, Sterling, Thompson, Windham, Woodstock.
Ryan and Megan Winslow of Winslow Homes have sold over 3,000 homes since 2009, with the home and the loan under one team. Call or text 386-690-5858.
17 years, over 3,000 homes sold, and one team for the home and the loan. Call or text 386-690-5858.
Sources: U.S. Census Bureau 2024 population estimates and 2019 to 2023 American Community Survey; Zillow Home Value Index, August 2026. Numbers update as new data is released. Talk to Ryan and Megan for current sold prices on your street.
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