Chester Homes for Sale

Welcome to Chester, South Dakota, a charming town nestled in the heart of Lake County. With its picturesque landscapes and warm community spirit, Chester is a hidden gem that offers both tranquility and a vibrant lifestyle. Known for its friendly atmosphere and tight-knit community, this quaint town is perfect for families, retirees, and anyone seeking a peaceful yet engaging environment.

Chester boasts a rich history and a variety of local amenities, including parks, shops, and delightful dining options. The town is surrounded by stunning natural beauty, with nearby lakes and recreational areas perfect for outdoor enthusiasts. Whether you enjoy fishing, hiking, or simply taking in the serene views, Chester has something for everyone.

For those considering a move to this idyllic location, there are a variety of homes for sale that cater to diverse tastes and budgets. From charming historic houses with character to modern family homes equipped with all the latest amenities, Chester’s real estate market offers a range of options to suit your lifestyle. Each property is nestled within a friendly neighborhood, ensuring that you’ll feel right at home from the moment you arrive.

If you’re ready to embrace the warm community and beautiful surroundings of Chester, SD, explore the available homes for sale today. With its unique blend of small-town charm and modern conveniences, Chester is the perfect place to find your forever home. Let us help you discover the ideal property that fits your dreams and lifestyle!

Newest Chester Homes for Sale

Courtesy of Maggie Miller from Hegg, REALTORS. OFFICE: 605-336-2100

$250,000

4 Beds ⋅ 2 Baths ⋅ 22608181 MLS

ORIGINAL CHARM INSIDE AND OUT! From the inviting covered front porch to the beautiful original woodwork throughout, this 4-bedroom, 2-bathroom home blends timeless character with thoughtful modern updates. The kitchen is full of personality with exposed brick, butcher block countertops, and stainless steel appliances, while the living room showcases original hardwood floors and a classic pocket door that adds to the home's historic appeal. All four bedrooms are conveniently located on the upper level, and main-floor laundry adds everyday convenience. Enjoy peace of mind with updates completed within the last several years, including windows, shingles, paint, water heater, and radon mitigation system. Outside, the fully fenced backyard offers privacy, while two detached garages provide plenty of options for vehicle parking, hobbies, or additional storage. If you're looking for a home with character you simply can't recreate, paired with updates that make everyday living easier, this one deserves a closer look!

303 E 2nd St, Chester

Courtesy of Dave Larson from Hegg, REALTORS. OFFICE: 605-336-2100

$435,000

3 Beds ⋅ 1 Baths ⋅ 22607886 MLS

Enjoy lake-area living at this charming one-level home just across the road from beautiful Lake Brandt! This 3-bedroom, 1-bath home offers a functional layout with everything conveniently located on one level. Whether you're looking for a year-round home, weekend getaway, or a place to enjoy everything lake life has to offer, this property is full of possibilities. A 1-stall garage provides additional parking and storage, while the location puts you just steps from the lake and all the recreation that comes with it. Enjoy boating, fishing, beautiful South Dakota summers, and the relaxed atmosphere of living near the water. Don't miss your chance to make this Lake Brandt property your own!

4861 S Spawn Cir, Chester

Courtesy of Jack VanLeur from Alpine Residential.

$720,000

5 Beds ⋅ 4 Baths ⋅ 22606992 MLS

Discover the lake home you’ve been dreaming of! This incredible, one-of-a-kind property on Lake Brant offers beach access, a 40-ft dock, jet ski lift, and breathtaking sunset views. Inside, modern amenities blend beautifully with timeless charm, featuring a stunning renovation with granite countertops, quality cabinetry, Andersen windows, tiled showers, wood floors, and tall ceilings. Designed for gathering, the spacious layout is perfect for large families looking to enjoy lake life together. The main floor features a private bedroom suite with its own entrance, while upstairs offers TWO impressive master suites, each with remarkable lake views and no detail overlooked. The upper-level living space opens to a charming Juliet balcony overlooking the water. There is truly too much to list—this is a property you need to experience in person. Come see it and make your lake-living dreams a reality!

5361 S Shore Dr, Chester

Courtesy of Callie Wockenfuss from Real Estate Retrievers of Sioux Falls.

$459,900

2 Beds ⋅ 1 Baths ⋅ 22604243 MLS

Rare opportunity to own one of Lake Brant's premier waterfront properties! Offering over 110 feet of shoreline frontage and nearly 140 feet of depth, this oversized lake lot provides an exceptional setting for your future dream home. The existing property features a charming 2-bedroom, 1-bath cabin, allowing you to start enjoying lake life immediately while planning for the future. The possibilities are endless with ample space to build a spectacular lakefront residence with a walk-out basement designed to capture breathtaking water views. Positioned near the deepest part of Lake Brant, this location offers outstanding boating, fishing, water skiing, jet skiing, and year-round recreation. Conveniently located just 25 minutes from Sioux Falls and a short drive to Brookings and Madison, you'll enjoy the perfect balance of lake living and accessibility. Nearby amenities include the popular Shipwreck Bar & Grill just minutes away and Lakes Golf Course only about 10 minutes from the property. Whether you're looking for a summer getaway, an investment opportunity, or the ideal location to build your forever lake home, this property is a rare find. Act quickly and you could be enjoying lake life in time for the Fourth of July! See Last Picture for example of what lot could look like with new home. Inside pictures digitally enhanced to indicate actual room sizes and space. !

5471 S Shore Dr, Chester

Courtesy of Todd Nelson from Harr & Lemme Real Estate. Cell: 605-321-9147

$539,900

2 Beds ⋅ 2 Baths ⋅ 22601406 MLS

Here is your opportunity to own a lake front compound that includes 2 lots with your own boat ramp on Lake Brant. Each lot measures 40ft x 80ft. Lakeside lot has its own water and sewer hookups. New exterior paint in 2025. Large kitchen features plenty of hickory cabinets, dual ovens and is open to living room. Entire main level has in-floor heat. Living room features projection TV with whole home audio and slider to patio with lake views. Two sizeable bedrooms with large walk-in closets and in-floor heat on upper level. Hickory trim and 3 panel Hickory doors throughout. 9000 watt generator hooked up to home. Water and sewer on lake side lot which provides plenty of room for expansion. 40 feet of beached shoreline to enjoy those summer sunsets with a bonfire and making memories with your family. Sale includes (2) 110 amp outlets and (2) 220 amp outlets for campers on the property. There is a back lot with metal storage/workshop building with propane that is also available for purchase at an additional price.

4892 N Spawn Cir, Chester

Start Your Search

The data relating to real estate for sale on this web site comes in part from the Internet Data Exchange Program of the REALTOR® Association of the Sioux Empire, Inc., Multiple Listing Service. Real estate listings held by brokerage firms other than our company are marked with the Internet Data Exchange™ logo or the Internet Data Exchange thumbnail logo (a little black house) and detailed information about them includes the name of the listing brokers. Information deemed reliable but not guaranteed. The broker(s) providing this data believes it to be correct, but advises interested parties to confirm the data before relying on it in a purchase decision. © 2026 REALTOR® Association of the Sioux Empire, Inc. Multiple Listing Service. All rights reserved.

Chester Homes for Sale

Newest Chester Homes for Sale

How much is your home worth?

How much is your home worth?