Chester Real Estate

Welcome to Chester, South Dakota – a charming small town nestled in the heart of Lake County. With a population of just over 800 residents, Chester offers a close-knit community atmosphere, where neighbors become friends and everyone knows each other by name. The town is steeped in rich history and boasts a unique blend of rural charm and modern conveniences, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Chester is surrounded by stunning natural beauty, with picturesque landscapes that include rolling hills, serene lakes, and lush greenery. Outdoor enthusiasts will appreciate the proximity to Lake Madison and Lake Herman, perfect for fishing, boating, and picnicking. The town also features several parks and recreational areas, providing ample opportunities for hiking, biking, and enjoying the great outdoors.

Culturally, Chester is vibrant and welcoming, with community events and festivals that bring residents together throughout the year. From the annual Chester Community Days to local farmers' markets, there's always something happening that fosters community spirit and togetherness.

In terms of amenities, Chester offers essential services, including shops, restaurants, and schools, ensuring that residents have everything they need right at their fingertips. The town's affordability and low cost of living make it an attractive option for those looking to settle down in a serene environment without sacrificing quality of life.

Whether you’re considering a move or simply looking for a place to visit, Chester, SD, is a delightful destination that captures the essence of small-town living while providing a welcoming community for all. Come discover the charm of Chester – where every day feels like home!

Newest Listings in 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 Brad Nelson from Grand Sothebys International Realty. CELL: 605-370-2099

$699,000

3 Beds ⋅ 3 Baths ⋅ 22602904 MLS

PRICED REDUCED - READY FOR NEW OWNERS! One of the premier lots on Brant Lake offering a rare walkout to a flat, 87 ft. sandy beach—perfect for effortless lakeside living. This custom-built, year-round ranch home sits on a ½-acre lot. The property features an oversized double attached garage, ready to install a garage heater if wanted and has in-floor heat. Plus there a fully insulated (spray foam) 28 x 40 detached heated garage complete with a concrete storm shelter, pull down screen on the single door, 100 amp panel that makes this ideal for storage, hobbies, or extra workspace. Built with efficiency in mind, the home offers superior insulation, in-floor heat throughout, plus dual heat with heat pump/propane forced air heating, Anderson High Performance windows, 2 x 6 construction, and 9’ ceilings across the entire main level. Inside, the kitchen is both functional and inviting, showcasing maple cabinetry, a large granite-topped center island, walk-in pantry, extra storage room and ceramic tile flooring. The primary suite features a walk-in ceramic tile shower, dual sinks, and a spacious walk-in closet. Two additional bedrooms, a full bath, convenient main floor laundry, and a half bath with direct access to the lake add to the thoughtful layout. Keep the lawn looking great with the water pumping setup using the lake water. Take in stunning sunsets over the water from the four-season room, back patio, or right on your own sandy shoreline—this is lake living at its finest.

23931 464th Ave, Chester

Courtesy of Brad Benson from Signature Realty Group LLC. Cell: 605-480-8003

$1,295,000

4 Beds ⋅ 4 Baths ⋅ 22602062 MLS

Experience elevated lake living with 100 feet of prime Brant Lake frontage in this exceptional 4-bedroom, 4-bathroom home offering over 3,400 square feet of thoughtfully designed space. Showcasing breathtaking water views throughout, this lakeside retreat blends luxury, comfort, and functionality. Custom details shine from the moment you enter, including a striking wrought iron staircase, impressive ceiling treatments, and high-end finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring granite countertops, a large center island, a hidden walk-in pantry, and a commercial-grade vent hood. The primary suite offers a private escape with a spa-like tiled walk-in shower, while rich wood flooring and elegant finishes enhance the home’s overall warmth and sophistication. The lower level includes two additional bedrooms, an expansive family room, and a wet bar—perfect for hosting guests or relaxing evenings at home. Step outside to enjoy the covered patio with a tucked-away hot tub, ideal for unwinding after a day on the lake. A lakeside storage shed provides convenient space for all your recreational gear, and the durable custom metal roof ensures lasting quality and curb appeal. This remarkable property offers the perfect balance of luxury amenities and serene lakefront living—an opportunity you won’t want to miss.

5381 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

Courtesy of Rick Trapp from eXp Realty - Elevated Sioux Falls.

$175,000

22508289 MLS

ON BLACKTOP ROAD. 6.8 acres just 3 miles South of Lake Madison and Lakes Restaurants & Golf Course with 1 eligibility to build a home or a shed-house. Currently the property has hay ground. Utilities are at the site Sioux Valley Electric, Kingsbrook Rural Water. SEE Plot Map with Total Acres 12.8. Property can be split into 2 property sites with Tract 2 having 6 Acres for $200,000 with shelter belt and Tract 3 having 6.8 Acres for $175,000. All together with 12.8 Acres. Both lots can be sold together for $350,000. Rick Trapp is the owner and a License Real Estate Agent in South Dakota.

461st Ave, Chester

Courtesy of Rick Trapp from eXp Realty - Elevated Sioux Falls.

$200,000

22508288 MLS

ON BLACKTOP ROAD 461st Ave. 6 acres just 3 miles South of Lake Madison and Lakes Restaurants & Golf Course with 1 eligibility to build a home or a shed-house. Fantastic shelter belt of trees, along. Utilities are at the site Sioux Valley Electric, Kingsbrook Rural Water. SEE Plot Map with Total Acres 12.8 Property can be split into 2 property sites with Tract 2 having 6 Acres with shelter for $200,000 and Tract 3 having 6.8 Acres for $175,000. Preferred to sell both lots together, 12.8 Acres. for $350,000. Rick Trapp is the owner and a License Real Estate Agent in South Dakota.

461st Ave, Chester

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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.