Chester Homes under $500,000

Chester Homes under $500,000

Welcome to Chester, South Dakota – a hidden gem nestled in the heart of Lake County. With its charming small-town atmosphere and stunning natural surroundings, Chester offers a perfect blend of tranquility and community spirit. This quaint city is known for its friendly residents, making it an ideal place for families, retirees, and anyone seeking a peaceful lifestyle.

Chester boasts a rich history and a vibrant local culture, characterized by annual events and festivals that bring the community together. The picturesque landscape surrounding the area is perfect for outdoor enthusiasts, with numerous parks, lakes, and trails just waiting to be explored. Whether you enjoy fishing, hiking, or simply taking in the breathtaking views, Chester has something for everyone.

When it comes to real estate, Chester is an attractive option for homebuyers seeking affordability without compromising on quality. With a variety of homes available for under $500,000, you can find your dream property in this charming city. From cozy single-family homes to spacious multi-bedroom residences, Chester offers diverse options to suit your lifestyle and budget.

Imagine raising your family in a home where the community feels like an extended family, or retiring in a peaceful neighborhood where you can enjoy your golden years. With its affordable housing market and welcoming atmosphere, Chester is not just a place to live; it’s a place to thrive. Explore the opportunities awaiting you in Chester, SD, and discover why this delightful city is the perfect place to call home!

Newest Chester Homes under $500,000

303 E 2nd St, Chester

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
4861 S Spawn Cir, 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
5471 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
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.

How much is your home worth?

Get instant property value now!