Chester Real Estate

Welcome to Chester, a charming town nestled in Penobscot County, Maine. Known for its picturesque landscapes and friendly community, Chester offers a tranquil setting for those looking to embrace a peaceful lifestyle.

With a rich history dating back to its early days as a logging town, Chester seamlessly blends the old with the new. Residents here take pride in their close-knit community, where neighbors often come together for town events and celebrations.

Nature enthusiasts will find plenty to explore in Chester, with its lush forests, winding rivers, and scenic hiking trails. Outdoor activities such as fishing, camping, and birdwatching are popular pastimes among locals.

Despite its serene ambiance, Chester is conveniently located near larger cities like Bangor, offering easy access to urban amenities while still maintaining its rural charm. Whether you're looking to settle down in a quaint neighborhood or build your dream home surrounded by nature, Chester has something for everyone.

Come discover the beauty and tranquility of Chester, Maine. Find your perfect piece of paradise in this idyllic town that feels like home from the moment you arrive.

Newest Listings in Chester

$295,000

3 Beds ⋅ 2 Baths

Welcome to 722 South Chester Road in Chester, Maine, where privacy, comfort, and outdoor adventure come together on 3.4± beautiful acres. This well-maintained 3-bedroom, 2-bath home offers 1,868± square feet of inviting living space and is perfectly situated for those seeking the peace of country living without sacrificing convenience. Inside, you'll find a spacious layout featuring a beautifully updated kitchen with quartz countertops, ample cabinet space, and room to gather with family and friends. Large Anderson windows, installed within the last five years, fill the home with natural light while adding energy efficiency and long-term value. The heated basement provides excellent space for storage, hobbies, a workshop, or future expansion to suit your needs. Outside, the possibilities continue. The attached two-car garage and two additional outbuildings provide plenty of room for vehicles, tools, recreational equipment, and more. As an added bonus, the lawn mower and snowblower convey with the property, making it even easier to maintain your new home. Outdoor enthusiasts will appreciate the property's proximity to ATV trails, excellent hunting opportunities, and its convenient location just 10 minutes from I-95, 45 minutes to Bangor, and 45 minutes to Baxter State Park, offering endless opportunities to explore the best of Maine. Whether you're searching for a year-round residence, a peaceful retreat, or a place to enjoy the Maine lifestyle, this property delivers space, privacy, and convenience. Schedule your private showing today and discover everything this exceptional Chester property has to offer!

722 S Chester Rd, Chester

Listing courtesy of United Country Lifestyle Properties of Maine. 207-794-6164

$215,000

2 Beds ⋅ 1 Baths

Discover a truly one-of-a-kind property offering the perfect blend of self-sufficiency and natural beauty. Situated on 12.6± surveyed acres in Chester, Maine, this unique homestead is ideal for those dreaming of country living, gardening, or creating a hobby farm. The property features a private pond, frontage along the scenic Medunkeunk Stream, and plenty of open space for gardens, animals, and outdoor recreation. Existing infrastructure includes power, a drilled well, a greywater system, and a composting toilet, making it well-suited for a sustainable lifestyle. Designed for convenient one-level living, the home offers a functional layout with a hallway laundry area, two bedrooms, a spacious living room and kitchen with a cozy wood stove, a sitting room or home office, and a second kitchen/living area featuring an additional wood stove--providing excellent flexibility for multigenerational living, guests, or a variety of other uses. Comfort is enhanced with three heat pumps, two wood stoves, and an on-demand hot water heater, offering efficient, year-round heating and cooling. Whether you're looking to homestead, start a small farm, enjoy gardening, or embrace a more self-sufficient lifestyle, this exceptional property offers endless possibilities surrounded by Maine's natural landscape.

62 Old Keene Rd, Chester

Listing courtesy of NextHome Experience.

$699,000

4 Beds ⋅ 3 Baths

Welcome to this exceptional modern farmhouse, built in 2018 and nestled on 80 acres of beautiful woods and open fields in Chester, Maine. Offering the perfect balance of comfort, privacy, and rural charm, this remarkable property is ideal for those seeking space to relax, explore, and enjoy the outdoors. Inside, you'll find 4 spacious bedrooms and 2.5 baths thoughtfully designed for modern living. The open-concept layout is filled with natural light and creates a seamless flow between the living, dining, and kitchen areas--perfect for everyday living and entertaining alike. The desirable main-floor primary suite offers comfort and convenience, creating a private retreat with easy access to the home's main living spaces. Three additional bedrooms provide plenty of room for family, guests, or a home office. The well-appointed kitchen features a propane range, while the convenient main-floor laundry room adds ease to daily living. Efficient heating systems include a propane furnace and two heat pumps to provide year-round comfort. Enjoy peaceful mornings on the welcoming front porch and unwind in the evenings on the back deck overlooking your expansive acreage. The attached two-car garage offers convenient parking and additional storage space for vehicles, equipment, and outdoor gear. Set on 80 acres of private woods and fields, with a view of Katahdin on clear days, this property offers endless possibilities--from recreation and hunting to gardening, hobby farming, or simply embracing the tranquility of country living. With modern construction, energy-efficient amenities, and abundant space to roam, this stunning Chester, Maine farmhouse delivers the best of rural living without sacrificing comfort or convenience.

272 N Chester Rd, Chester

Listing courtesy of True North Realty, Inc..

$155,000

3 Beds ⋅ 1 Baths

Welcome to this split level home nestled on approximately 2+/- acres in Chester, Maine. Built in 1983, this 3 bedroom, 1 bath residence offers 1,250 square feet of comfortable living space with beautiful views and a peaceful country setting. Inside, you'll find a functional layout with bright living spaces and room to make the home your own. The attached garage provides convenience and additional storage, while outside the property offers plenty of space to enjoy all that rural Maine living has to offer. The grounds offer a beautiful blend of established landscaping and usable outdoor space, featuring mature lilac bushes, a garden area, and fruit trees scattered throughout the property for seasonal enjoyment. A detached storage building provides additional room for tools, equipment, hobbies, or recreational gear. Located in the quiet town of Chester, this property offers the charm of small town Maine living while remaining conveniently positioned for access to nearby services and recreation. The area is known for its scenic surroundings, outdoor opportunities, and easy access to trails, lakes, and year-round activities that make this region appealing for both full time residents and those seeking a slower pace of life. Whether you're looking for a year round residence or a place to enjoy the quiet surroundings, scenic views, and outdoor space, this property offers comfort and opportunity in a welcoming Maine community.

247 Pea Ridge Rd, Chester

Listing courtesy of Acres Away, Inc..

$180,000

2 Beds ⋅ 1 Baths

Tucked away in the recreational heart of Chester, this well cared for chalet style home at 91 Pea Ridge Road offers comfort, functionality, and the benefits of low-tax living. Known for its peaceful setting and outdoor lifestyle, Chester is a favorite for those seeking privacy without sacrificing access to Maine's four-season recreation. The home features two bedrooms and one full bath, with a warm and inviting layout that has been thoughtfully maintained over the years. An attached two-car garage provides direct entry into the home, making everyday living convenient in all seasons. Adding even more versatility is an additional one-car garage attached to the rear of the property—ideal for storing recreational equipment, tools, or vehicles. Outside, the well-manicured lawn creates a pleasant setting for relaxing or entertaining, while a charming barn-style shed offers extra storage or potential space for small farm animals. The property is serviced by private utilities and is designed for easy, efficient living. Located in a highly desirable recreational area, this property offers close proximity to hunting, fishing, ATV trails, and snowmobile routes, making it an excellent year-round base for outdoor enthusiasts. Whether you're looking for a full-time residence, a seasonal retreat, or a manageable getaway in a low tax town, this chalet delivers a rare combination of comfort, storage, and location. A well maintained home in a sought after recreational community, ready to be enjoyed from day one.

90 Pea Ridge Rd, Chester

Listing courtesy of Acres Away, Inc..

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