Chester, located in Hampden County, Massachusetts, is a picturesque town known for its scenic landscapes, rich history, and tight-knit community. With a blend of rural charm and modern conveniences, Chester provides a serene lifestyle surrounded by beautiful nature. This article explores the best residential areas in Chester, highlighting their characteristics, housing options, and average prices.
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Chester Village

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Chester Village is the center of the town, offering a quaint, small-town atmosphere with local shops, restaurants, and community events. It’s ideal for those who enjoy being in the heart of the action while having easy access to nature.
Characteristics of the Chester Village
* Culture: Historic homes and local artisan stores
* Transportation: Mostly walkable; proximity to major routes
* Services: Grocery stores, local cafes, and community services
* Environment: Friendly and community-oriented
Housing Options in the Chester Village
Single-family homes, historic buildings
Average Home Prices in the Chester Village
* Buying: $250,000 – $350,000
* Renting: $1,200 – $1,800/month
Chester Woods

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Chester Woods area is known for its lush greenery and spacious properties, making it a great choice for families and those looking for more land. It offers a serene environment with plenty of outdoor activities nearby.
Characteristics of the Chester Woods
* Culture: Nature-centric community and outdoor enthusiasts
* Transportation: Car necessary for commuting; rural roads
* Services: Limited amenities, but close to nature parks
* Environment: Peaceful and spacious
Housing Options in the Chester Woods
Large single-family homes, some new constructions
Average Home Prices in the Chester Woods
* Buying: $300,000 – $450,000
* Renting: $1,500 – $2,000/month
Chester Hill

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The Chester Hill area is known for its elevated views and quiet streets. It is ideal for those looking for a tranquil setting near hiking trails and nature spots.
Characteristics of the Chester Hill
* Culture: Outdoor activities and hiking trails close by
* Transportation: Car essential; private and secluded roads
* Services: Basic amenities available; more extensive ones in nearby towns
* Environment: Tranquil and scenic
Housing Options in the Chester Hill
Single-family homes, custom-built homes
Average Home Prices in the Chester Hill
* Buying: $280,000 – $400,000
* Renting: $1,400 – $1,900/month
Blissful Meadows

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Blissful Meadows offers a blend of pastoral beauty with modern family homes. It is perfect for those wanting to enjoy the suburban feel while being a short drive from Chester Village.
Characteristics of the Blissful Meadows
* Culture: Family-friendly community events and activities
* Transportation: Easy access to main roads; minimal public transport
* Services: Schools, parks, and local shops nearby
* Environment: Suburban and welcoming
Housing Options in the Blissful Meadows
Newer single-family homes, townhomes
Average Home Prices in the Blissful Meadows
* Buying: $320,000 – $475,000
* Renting: $1,600 – $2,300/month
Long Lake Area

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The Long Lake area is a hidden gem providing lakeside living with opportunities for fishing, boating, and other water activities. This region attracts those who enjoy recreational pursuits and water sports.
Characteristics of the Long Lake Area
* Culture: Active lifestyle focused on outdoor water activities
* Transportation: Car needed to reach shops and restaurants; local roads
* Services: Limited with some lakeside amenities
* Environment: Lakeside and recreational
Housing Options in the Long Lake Area
Lakefront homes, vacation-style cabins
Average Home Prices in the Long Lake Area
* Buying: $350,000 – $600,000
* Renting: $1,800 – $2,500/month
Huntington Road

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Huntington Road is characterized by larger properties set back from the road, providing privacy and a rural feel. It is popular among agricultural enthusiasts and those who enjoy gardening.
Characteristics of the Huntington Road
* Culture: Rural lifestyle with a focus on farming and gardening
* Transportation: Car essential; rural and quiet roads
* Services: Farmers markets and related services
* Environment: Rural and cozy
Housing Options in the Huntington Road
Farmhouses, single-family homes on larger lots
Average Home Prices in the Huntington Road
* Buying: $280,000 – $380,000
* Renting: $1,300 – $1,800/month
Frequently Asked Questions About the Best Residential Areas in Chester:
The best residential areas in Chester include Chester Village, Chester Woods, Chester Hill, Blissful Meadows, Long Lake Area, and Huntington Road.
Blissful Meadows is considered the most family-friendly due to its community events and amenities like parks and schools.
The average price of homes in Chester ranges from $250,000 to $600,000, depending on the area and type of home.
The Long Lake Area offers a variety of waterfront properties, ideal for those looking to enjoy water activities.
Yes, Chester offers a peaceful atmosphere with plenty of outdoor activities, making it a great place for retirees.
Chester offers a range of housing options, including single-family homes, historic properties, and lakefront cabins.
Public transportation options are limited, so having a car is recommended for getting around and commuting.
Chester hosts local events, farmers markets, and has nearby hiking trails and nature parks contributing to its cultural scene.
Yes, Chester is served by quality schools with a strong community involvement, making it great for families.
The real estate market in Chester has been stable with a good mix of houses available for various budgets, especially appealing for families and those seeking a rural lifestyle.
Conclusion on the Best Residential Areas in Chester:
Chester offers a diverse range of residential areas tailored to a variety of lifestyles, whether you're seeking a vibrant village atmosphere, a tranquil lakeside retreat, or a spacious rural property. Each neighborhood has its unique charm and advantages, appealing to families, retirees, and outdoor enthusiasts alike. The real estate market remains active, with properties ranging from historic homes to modern new builds. With its captivating natural surroundings and strong community spirit, Chester is an excellent choice for anyone looking to enjoy the tranquility of rural living without sacrificing modern amenities.
About the Author

Published by:Eribert De Oliveira
Mechatronics Engineer and founder of Mi Inmueble Online, with a background in real estate. I combine technology and analysis to help you find the best areas to live.