ChesterAre Real Estate

Welcome to the Chester Area School District, nestled in the heart of Lake County, South Dakota! This vibrant educational community is dedicated to fostering a nurturing environment where students can thrive academically, socially, and emotionally. The Chester Area School District serves students from preschool through high school, offering a comprehensive curriculum designed to meet the diverse needs of all learners.

One of the standout features of the Chester Area School District is its commitment to small class sizes, ensuring that each student receives personalized attention from highly qualified educators. With a focus on innovative teaching methods and hands-on learning experiences, students are encouraged to explore their interests and develop critical thinking skills that will serve them well beyond the classroom.

In addition to a strong academic foundation, the Chester Area School District prides itself on offering a wide range of extracurricular activities. From athletics to arts programs, students have ample opportunities to discover their passions and build lasting friendships. The district also emphasizes community involvement, fostering a sense of belonging and support among families.

Located in the picturesque town of Chester, residents enjoy a close-knit community atmosphere, with access to local parks, recreational facilities, and a variety of family-friendly events throughout the year. The town’s welcoming spirit and commitment to education make it an ideal place for families seeking a quality lifestyle.

Choosing Chester Area School District means investing in a bright future for your children. With dedicated educators, supportive families, and a rich community culture, this is where lifelong learning begins!

Newest Listings in ChesterAre

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

$125,000

22607980 MLS

Photos are virtual. Interior photo shows possibilities for living quarters and is "similar to". Currently under construction with a completion date of 11-30-2026. Why rent a storage unit/shouse/condo when you can own? Prime location near Lake Madison and the Lakes Golf Course. Perfect for a Man Cave, She Shed or living quarters with 1500 sq ft of main floor space. 25 ft x 60 ft unit with 16 ft wide x 14 ft high door and full concrete floor and common areas. All Units are available with full water and sewer hook ups. Sheetrocked and insulated side walls with plenty of outlets. Can be customized at an additional cost. Mezzanine space from 600 sq ft to 720 sq ft possible for an additional $15,000. Multiple units available. HOA of $1560/year includes building insurance, electrical meter for security camera and lights, snow, and lawncare.

120 Osprey Ave Unit 5, Wentworth

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

$349,000

3 Beds ⋅ 3 Baths ⋅ 22607214 MLS

Welcome to the Lakes Community and Lakes Golf Course near Lake Madison and Round Lake. Middle unit of a Lakes Golf Course ranch tri-plex with a full lower level finish. Watch them putt on #8 from the back deck or tee off from #9 from the front. This means no back or front yard neighbors the vast majority of the year. Potential for great current 4+ year renters to sign new lease if this is purchased as an investment property. Great summer VRBO & Off-Season Rental to students. Lots of options in this wonderful playground community. HOA is $150 per year and covers streetlights and community park that includes a dock on Round Lake, pickleball and basketball court, children's play system and shelter with electricity. Road district is established to maintain roads in the community and is assessed at $600 per year on property taxes. Seller is a licensed Real Estate Broker in the State of South Dakota.

104 Lake Dr, Wentworth

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 John Mallinger from Hegg, REALTORS. OFFICE: 605-336-2100

$40,000

22606667 MLS

Your Lake Madison getaway starts here! This lot at Lake Madison RV Resort offers the perfect opportunity to create your own weekend escape or seasonal retreat. Bring your camper or tiny home and enjoy everything resort living has to offer, including a private swimming pool, sand volleyball court, horseshoe pit, and convenient bath house. Spend your days relaxing by the lake, enjoying the amenities, and making the most of South Dakota summers. Come see why lake life is calling!

100 Silver Creek Trl, Wentworth

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

$165,000

22605926 MLS

Photos are virtual. Interior photo shows possibilities for living quarters and is "similar to". Currently under construction with a completion date of 11-30-2026. Why rent a storage unit/shouse/condo when you can own? Prime location near Lake Madison and the Lakes Golf Course. Perfect for a Man Cave, She Shed or living quarters with 1800 sq ft of main floor space with an additional 720 Sq Ft of Mezzanine space. 30 ft x 60 ft unit with 16 ft wide x 14 ft high door and full concrete floor and common areas. All Units are available with full water and sewer hook ups. Sheetrocked and insulated side walls with plenty of outlets. Can be customized at an additional cost. Multiple units available. HOA of $1560/year includes building insurance, electrical meter for security camera and lights, snow, and lawncare.

122 Osprey Ave Unit 3, Wentworth

Courtesy of Rick Trapp from eXp Realty - Elevated Sioux Falls. Cell: 605-728-8521

$685,000

3 Beds ⋅ 2 Baths ⋅ 22605357 MLS

Welcome to one of the finest homes to hit the market in The Lakes Golf Course community in years! Built with exceptional craftsmanship and quality throughout, this impressive ranch-style home offers the perfect combination of luxury, functionality, and peace of mind. The thoughtfully designed main floor features three spacious bedrooms, two bathrooms, and an oversized three-stall garage. The expansive living room is warm and inviting with a stunning gas fireplace, custom built-in custom cabinetry, and plenty of room for entertaining. The chef's kitchen is truly the heart of the home, showcasing quartz countertops, LG appliances, abundant custom cabinetry with convenient pull-out shelves, a large eat-up peninsula, and an incredible walk-in pantry offering storage galore. The primary suite is a private retreat featuring a generous walk-in closet and a luxurious ensuite complete with a soaking tub, walk-in Onyx shower, and expansive vanity. You'll also appreciate the oversized main-floor laundry room with built-in cabinetry, folding counter, and an additional flex room perfect for a home office, pet room, hobby space, or extra storage. The unfinished basement is ready for your personal vision and has been built with efficiency in mind, featuring both blown-in and batt insulation for outstanding comfort and energy performance. Step outside to enjoy both covered concrete porches —the rear overlooking the beautiful surroundings and the front porch providing the perfect place to enjoy both sunrises and sunsets. The exterior is equally impressive with maintenance-free steel siding and soffits that never require painting, gutter guards for easy upkeep, and an oversized garage complete with a floor drain. Perhaps the home's most remarkable feature is the whole-house natural gas generator, providing automatic backup power within seconds of an electrical outage, offering comfort and security year-round. Homes of this caliber rarely become available. Don't miss this incredible opportunity to own an exceptionally built home in one of the area's most desirable golf course communities. Schedule your private showing today!

109 Lake Ridge Dr, Wentworth

Courtesy of Todd Nelson from Harr & Lemme Real Estate.

$84,500

22605182 MLS

Welcome to the Lakes Community located between Lake Madison and Lake Brant. This walk out lot is located between holes 7 and 8 of the Lakes Golf Course. Great views of Hole number 7 green and hole number 8 tee box. Living on the golf course is like being on vacation all year long. The small HOA fee of $150/year takes care of street lights and a park that borders Round Lake with a community dock, playground, sand volleyball court and two pickleball courts. The Road District is assessed on taxes at $600 a year to cover road maintenance. Lake Madison Sanitary Sewer district, Sioux Valley Electric, Big Sioux Rural Water and Northwestern Energy handle the utilities that are at the lot. Just a short golf cart ride away is Lakes Bar & Grill that is open year round with a friendly and inviting atmosphere as well as great food. Covenants and Restrictions apply to help protect your investment.

Lake Ridge 11a Dr, Wentworth

Courtesy of Travis LaQua from Hegg, REALTORS.

$67,500

22605178 MLS

Build your dream home just one block from beautiful Lake Madison! This spacious lot is located in a new development on the south side of the lake along Nordstrom Trail. Enjoy a prime location just 2 minutes from Walker's Point State Recreation Area, featuring a boat launch and sandy beach, and only minutes from Hillside Resort, offering live entertainment, a restaurant/bar, and convenience store. This lot is approved for either a single-family home or a shouse, providing flexibility to fit your vision. Utilities available include Big Sioux Water, Sioux Valley Energy (electric), city sewer, and Northwestern Energy (natural gas). Don't miss this opportunity to enjoy lake-area living with modern conveniences nearby—must see!

Tbd Nordstrom Trl, Wentworth

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

$599,900

4 Beds ⋅ 3 Baths ⋅ 22605091 MLS

Easy living in the Lakes Community on hole #8 of the Lakes Golf Course near Lake Madison! Four bedroom, 2 1/2 bath ranch home. The main level has an open concept kitchen/living room with granite tops, electric fireplace, built-ins and formal dining. Huge pantry just inside from the garage. Easy access with 3' doors, maple flooring on main level and main floor laundry. Primary Suite has whirlpool tub, tiled shower and walk in closet. Lower level includes 3 bedrooms, full bath with dual vanity, large family room and unfinished storage/mechanical room. This home was designed with efficiency in mind: permanent cement board siding, aluminum soffit/facia, closed cell foam insulation (completely seals the walls which means no drafts), & Pella fiberglass windows. The backyard has fairway and green views of hole #8 with mature trees, a covered Trex deck and firepit. The South facing home and driveway means less hassle during the beautiful South Dakota winters. The South facing dormer will allow the winter sunlight to pour into your new home. The oversized garage is heated, includes hot and cold water and is designed for your cars and golf cart. The small HOA fee ($150 per year) takes care of street lights and a park that borders Round Lake with a community dock, playground, sand volleyball court and two pickleball courts. The Road District is assessed on taxes at $600 a year to cover road maintenance. Just a short golf cart ride away is the Lakes Bar & Grill that is open year round with a friendly and inviting atmosphere as well as great food. Covenants and Restrictions apply to help protect your investment.

54 N Gulch Ln, Wentworth

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

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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.

ChesterAre Real Estate

Newest Listings in ChesterAre

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