Chester Homes for Sale

Welcome to Chester, Michigan—an enchanting community nestled in the heart of Otsego County. Known for its picturesque landscapes and friendly atmosphere, Chester offers a serene lifestyle that perfectly balances small-town charm with modern conveniences. With its lush greenery, sparkling lakes, and scenic trails, this neighborhood is ideal for nature lovers and outdoor enthusiasts alike.

Chester boasts a tight-knit community where neighbors become friends, and local events bring everyone together. Enjoy summer picnics at the local parks, or take part in seasonal festivities that celebrate the vibrant spirit of the area. With excellent schools, friendly shops, and cozy cafes, Chester provides all the essentials for comfortable living while maintaining a peaceful ambiance.

For those looking to make Chester their home, you’ll be delighted to discover a variety of homes for sale that cater to different lifestyles and budgets. Whether you’re searching for a charming cottage, a spacious family home, or a modern retreat, the real estate options here are as diverse as the community itself. Many properties feature stunning views, ample outdoor space, and convenient access to local amenities, making them perfect for families, retirees, and everyone in between.

Investing in a home in Chester means embracing a lifestyle filled with tranquility, community spirit, and natural beauty. Explore the available listings today and find your dream home in this idyllic Michigan neighborhood. Your new life in Chester awaits!

Newest Chester Homes for Sale

$469,900

5 Beds ⋅ 3 Baths ⋅ 201841745 MLS

Big Lake! Just minutes from downtown Gaylord, this captivating property on Big Lake offers two charming log cabins, each with its unique allure. The main cabin, meticulously maintained, features 3 bedrooms, 1.5 bathrooms, and elegant, original hardwood floors that lead you through a warm living space. Step out onto the deck or relax on the expansive patios to soak up the breathtaking lake views. A sandy beach and a 12x16 boathouse is a rare add to the lakeside charm. The second cabin offers a spacious living area, perfect for gatherings, with 2 bedrooms and 1 bath, making it a perfect guest retreat. Situated on .65 acres with 136 feet of lake frontage, this property is a haven for relaxation, water activities, plentiful golf and ski options and local shopping. Don't miss out on this one.

1598 Shallow Shores Dr, Gaylord

$350,000

3 Beds ⋅ 3 Baths ⋅ 201841491 MLS

3560 Southview Dr, Johannesburg

$539,000

2 Beds ⋅ 2 Baths ⋅ 201841466 MLS

COME HOME TO 45 private acres near Treetops Golf & Ski Resort in beautiful Gaylord, Michigan! This charming 2+ bedroom, 2-bath home features a spacious loft ideal for extra sleeping, a bunk room or cozy sitting area. Relax on the deck overlooking your private trout pond flowing into a scenic creek winding through the woods. Warm tongue-and-groove interiors, custom kitchen cabinetry and a welcoming Up North feel make this home truly special. Includes a 28x28 attached garage plus a 14x18 storage garage for ATVs and toys. Rolling wooded acreage offers trails, 3 elevated deer blinds and a field perfect for a future food plot. New power has been extended to the rear of the property for future possibilities. Ideal as a year-round home, hunt camp or Northern Michigan retreat!

5031 Wilkinson Rd, Gaylord

$589,000

3 Beds ⋅ 3 Baths ⋅ 201841311 MLS

Come home to a wonderful WATERFRONT on ALL-SPORTS BIG LAKE! Beautifully maintained 3 BR, 3 Bath ranch with 99' of frontage, just 5 miles east of downtown Gaylord, Michigan, close to Treetops and Otsego Golf & Ski Resorts! Recent updates include a newer roof, heating system, attic insulation, water heater, and more. Gorgeous granite kitchen features stainless steel appliances, breakfast bar and dining room. Take in splendid lake views from the spacious living room or relax in the enclosed sun porch, ideal as a sitting room or sleeping area. A finished walkout lower level includes a solid-surface wet bar with bar fridge, spacious living/dining areas, bunk room, and 3rd full bath. Enjoy the lakeside cabana/beach house, too! A perfect year-round home, getaway, or vacation rental property

1741 Big Lake Rd, Gaylord

$330,000

3 Beds ⋅ 2 Baths ⋅ 201841174 MLS

ADORABLE CHALET AT LAKE LOUISE - This 3 bedroom, 2 bath home with walkout basement has been updated and upgraded with quality materials and workmanship. As you enter the home , the new covered porch invites you in to find NEW - LVT flooring thoughout, new Kitchen including appliances, new baths, lovely solid wood interior doors, light fixtures, plumbing fixtures & fresh paint. Exterior has new siding, roof, side stairs with deck, landscaping, some new windows, all new exterior doors and new front covered porch. Enjoy all the amenities of Lake Louise amenities include Private shared Deeded Access to ALL-Sports lake, park with Pavillion, boat launch, bathouse and playgrounds. It's a must see and won't last long! Make your appointment today!

3074 Coolwater Ave, Johannesburg

$229,000

3 Beds ⋅ 2 Baths ⋅ 201840645 MLS

Private Up North Retreat! 🌲 Very well maintained 3-bedroom, 1.5-bath chalet situated on .68 acres in a peaceful, private setting. This charming home features a nice open floor plan with plenty of space to gather and relax. Enjoy the beauty of Northern Michigan from your own secluded getaway while still being close to outdoor recreation. Additional features include a spacious 24' x 24' detached garage, perfect for storing vehicles, toys, or workshop space. Conveniently located near Little Bass Lake public access, making it easy to enjoy boating, fishing, and all your favorite lake activities. Whether you're looking for a year-round home or a weekend escape, this property is a must-see!

8078 Old State Rd, Johannesburg

$224,900

2 Beds ⋅ 1 Baths ⋅ 201840260 MLS

Amazing property you have to experience in person! Nestled on 22 breathtaking acres with frontage on a Crapo Creek flowing into the North Branch Au Sable River, perfect for canoeing, kayaking, or a peaceful swim. This dreamy Northern Michigan retreat is filled with trails & designed for comfort, function, & peaceful Up North living. Charming 2 bedroom, 1 bath home in exceptional condition offers the perfect place to unwind and enjoy nature. Thoughtful details include an on site generator and canoes included with the sale. Tucked into a quaint, private setting, this property offers charm, privacy, and a true escape that still feels like home. Whether you're looking for a getaway, year round retreat, or your own slice of Northern Michigan paradise, this one is special. Ready to enjoy today!

11786 Monarch Meadow Trl, Grayling

$175,000

2 Beds ⋅ 1 Baths ⋅ 201840222 MLS

Charming & full of potential, this super adorable 2 bedroom, 1 bath cabin offers the perfect blend of cozy comfort & peaceful surroundings near the North Branch Au Sable River. Tucked into a private setting, this inviting retreat features an attached garage, additional family room for extra living space, & a storage shed for all your outdoor gear or hobby needs. Step outside to enjoy the tranquil patio setting, perfect for relaxing, entertaining, or soaking in the peaceful surroundings. Whether you are looking for a getaway, year round living, or an investment opportunity, this charming cabin offers the chance to make it your own & create an adorable retreat to enjoy for years to come.

5715 Loeffler Dr, Grayling

$449,900

3 Beds ⋅ 2 Baths ⋅ 201840004 MLS

Northern Michigan lakefront living at its finest on beautiful Big Lake in Gaylord! This updated 3 bedroom, 2 bath ranch seamlessly blends modern style with waterfront relaxation. Step inside to bright, refreshed interiors featuring an easy-flowing layout and thoughtful updates throughout. Year-round comfort is guaranteed thanks to a brand-new forced air furnace and central A/C. High-speed fiber internet keeps you seamlessly connected for remote work or streaming. Storage abounds with generous closets and ample space for all your water sports gear and Up North essentials. Outside, enjoy endless summer fun, fishing, and stunning water views right from your composite deck. Whether you're seeking a primary residence or a vacation getaway, this turn-key property delivers it all for $449,900!!

1761 Big Lake Rd, Gaylord

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