Chestertown, nestled within the scenic landscapes of Warren County, New York, is a charming hamlet that offers a small-town lifestyle surrounded by nature. Known for its picturesque views, friendly community, and access to outdoor activities, Chestertown provides an excellent quality of life. This article details the best residential areas in Chestertown, emphasizing their unique characteristics, housing options, average prices, and lifestyle amenities.
Table of Contents
Downtown Chestertown

(Image for illustration purposes only.)
Downtown Chestertown is the central hub of the hamlet, featuring a mix of local shops, cafes, and services. It is ideal for those who enjoy vibrant community life and easy access to amenities.
Characteristics of the Downtown Chestertown
* Culture: Art galleries, seasonal festivals, and local markets.
* Transportation: Walkable area with easy access to main roads; public transport options are limited.
* Services: Grocery stores, dining options, healthcare services, library, and post office.
* Environment: Friendly and community-oriented, often bustling during events.
Housing Options in the Downtown Chestertown
Single-family homes, townhouses, and apartments.
Average Home Prices in the Downtown Chestertown
* Buying: $200,000 – $350,000
* Renting: $1,200 – $1,800/month
Loon Lake Area

(Image for illustration purposes only.)
The Loon Lake Area is a scenic neighborhood surrounding one of the region's beautiful lakes, perfect for those who love fishing, boating, and outdoor recreation.
Characteristics of the Loon Lake Area
* Culture: Strong emphasis on outdoor activities, lakefront events, and a close-knit community.
* Transportation: Car is essential; limited public transport options.
* Services: Local shops close by, primarily offering lake-related supplies and services.
* Environment: Tranquil and picturesque, with stunning waterfront views.
Housing Options in the Loon Lake Area
Lakefront cottages, single-family homes, and vacation homes.
Average Home Prices in the Loon Lake Area
* Buying: $250,000 – $450,000
* Renting: $1,500 – $2,500/month
Chester Creekside

(Image for illustration purposes only.)
Chester Creekside is known for its lush landscapes and proximity to hiking trails. It appeals to outdoor enthusiasts and those seeking a peaceful lifestyle near nature.
Characteristics of the Chester Creekside
* Culture: Focus on hiking, wildlife observation, and natural events throughout the year.
* Transportation: Car recommended due to limited public transportation.
* Services: Convenient access to local amenities and recreational facilities.
* Environment: Peaceful, nature-oriented, with a family-friendly vibe.
Housing Options in the Chester Creekside
Single-family homes, cabins, and custom-built houses.
Average Home Prices in the Chester Creekside
* Buying: $180,000 – $320,000
* Renting: $1,000 – $1,600/month
Greenwood Forest

(Image for illustration purposes only.)
Greenwood Forest offers a tranquil escape with its wooded landscapes and proximity to hiking paths, making it ideal for families and nature lovers.
Characteristics of the Greenwood Forest
* Culture: Strong community spirit with active involvement in local events and recreational activities.
* Transportation: Vehicle access is necessary; community is spread out.
* Services: Local grocery and supplies, with larger shopping options available in nearby towns.
* Environment: Relaxed and serene, perfect for a family-oriented lifestyle.
Housing Options in the Greenwood Forest
Single-family homes with large lots and some townhouses.
Average Home Prices in the Greenwood Forest
* Buying: $220,000 – $370,000
* Renting: $1,100 – $1,800/month
Brant Lake Village

(Image for illustration purposes only.)
Brant Lake Village, close to Chestertown, is perfect for those seeking a peaceful, lakeside life with easy access to Chestertown's amenities.
Characteristics of the Brant Lake Village
* Culture: Community events focus on boating and fishing; intimate, friendly environment.
* Transportation: Car travel is essential; limited public transportation options.
* Services: Basic amenities, local eateries, and recreational facilities available.
* Environment: Quaint and serene, with lake views and peaceful surroundings.
Housing Options in the Brant Lake Village
Cottages, single-family homes, and summer residences.
Average Home Prices in the Brant Lake Village
* Buying: $210,000 – $380,000
* Renting: $1,200 – $2,000/month
Chestertown Woods

(Image for illustration purposes only.)
Chestertown Woods is surrounded by dense woodlands that offer a beautiful backdrop for outdoor activities like hiking, biking, and bird watching.
Characteristics of the Chestertown Woods
* Culture: Active lifestyle-focused community with nature-oriented activities and gatherings.
* Transportation: Requires a car for access; limited public transportation services.
* Services: Basic shopping needs met locally, with more extensive shopping available in nearby larger towns.
* Environment: Tranquil and lush, fostering a natural environment.
Housing Options in the Chestertown Woods
Single-family homes and eco-friendly builds.
Average Home Prices in the Chestertown Woods
* Buying: $200,000 – $360,000
* Renting: $1,000 – $1,600/month
Frequently Asked Questions About the Best Residential Areas in Chestertown:
The best residential areas in Chestertown include Downtown Chestertown, Loon Lake Area, Chester Creekside, Greenwood Forest, Brant Lake Village, and Chestertown Woods.
Loon Lake Area and Chester Creekside are ideal for outdoor enthusiasts due to their proximity to lakes and hiking trails.
Downtown Chestertown has the highest concentration of shops, dining, and community services.
Housing options include single-family homes, townhouses, lakefront cottages, and eco-friendly builds.
Greenwood Forest and Chester Creekside are popular among families due to the family-friendly atmosphere and outdoor activities.
Yes, rental options are available across various neighborhoods, with monthly prices typically ranging from $1,000 to $2,500.
Home prices can vary widely depending on the area, typically ranging from $180,000 in quiet neighborhoods to $450,000 for lakefront properties.
Loon Lake Area and Chestertown Woods are well-known for their serene environments, making them ideal for those seeking tranquility.
The Downtown Chestertown area usually hosts a variety of community events throughout the year, fostering a strong local culture.
Most residents rely on cars for transportation, as public transportation options are limited.
Conclusion on the Best Residential Areas in Chestertown:
Chestertown, NY, is a charming and picturesque destination for those seeking a warm community and access to stunning natural landscapes. With its various residential areas each offering unique characteristics, potential residents can find spaces that cater to their lifestyle, from vibrant communities with easy access to amenities in Downtown Chestertown to tranquil, nature-centric living in areas like Loon Lake and Chester Creekside. The choice of housing options, coupled with a range of prices, makes Chestertown an inviting place for families, active individuals, and those looking to unwind amidst nature. Whichever area you choose, Chestertown promises a fulfilling living experience in a stunning setting.
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.