ChesterAre Real Estate

Welcome to Chester Area School District, a vibrant educational community nestled in the heart of Chester, South Dakota. Known for its commitment to excellence in education, Chester Area School District serves students from preschool through high school, offering a nurturing environment where academic achievement and personal growth go hand in hand.

Chester Area School District prides itself on a dedicated team of educators who are passionate about fostering a love for learning. With a focus on innovative teaching methods and a robust curriculum, students are encouraged to explore their interests and develop critical thinking skills. The district boasts a student-to-teacher ratio that allows for personalized attention, ensuring that each child receives the support they need to thrive.

In addition to a strong academic foundation, Chester Area School District emphasizes the importance of extracurricular activities. Students have the opportunity to engage in a variety of sports, arts, and clubs, allowing them to discover their talents and build lasting friendships. The sense of community is palpable, as families and educators come together to support students in their endeavors.

The district is also committed to integrating technology into the classroom, preparing students for the challenges of the future. With access to modern resources and facilities, Chester Area students are well-equipped to excel in an increasingly digital world.

Choosing to settle in the Chester area means not only investing in a beautiful home but also in a future filled with educational opportunities for your children. Experience the charm of Chester and the excellence of its school district—where education meets community!

Newest Listings in ChesterAre

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 10-15-2026. 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. 23 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 Todd Nelson from Harr & Lemme Real Estate. Cell: 605-321-9147

$125,000

22605919 MLS

Photos are virtual. Interior photo shows possibilities for living quarters and is "similar to". Currently under construction with a completion date of 10-15-2026. 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 4, Wentworth

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

$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 Tonya Madsen from 605 Real Estate LLC.

$1,450,000

5 Beds ⋅ 3 Baths ⋅ 22604684 MLS

From peaceful sunrise mornings to unforgettable sunset evenings, this extraordinary lakefront retreat showcases some of the most breathtaking views on the lake and offers the ultimate year-round lifestyle of luxury, relaxation, and lasting memories. This stunning ranch walk-out offers an open concept with 5 bedrooms, 3 baths, vinyl plank flooring throughout, and stylish stepped ceiling detail. The kitchen features gorgeous quartz countertops that continue seamlessly up the wall as a full backsplash, high-end finishes, abundant workspace, and a massive hidden pantry complete with two additional refrigerator/freezer units for ultimate convenience. The open concept living area is highlighted by a striking electric fireplace wall with custom built-ins surrounding the TV, offering both style and functional storage. Expansive 9-foot doors lead directly out to the large heat-resistant deck, creating seamless indoor-outdoor living and showcasing breathtaking lake views. Primary suite offers an ensuite bath with a walk-in closet that includes laundry and direct access to the deck. Descend to the lower level to find a walk-out family room, 3 additional bedrooms, full bath, safe room, laundry space and storage room. Designed with entertaining in mind, it also features an incredible gathering space complete with a bar and a garage-style door that opens to the massive patio, pool, and hot tub area. The outdoor living space was thoughtfully designed with a heated auto-fill pool, creating a worry-free setup. 1,278 sq ft heated garage with storage room. The home is also wired for a whole-house generator. Commercial steel roof. Endless lake days, sunset cruises, poolside afternoons, and nights under the stars—this extraordinary property brings the ultimate Lake Madison lifestyle to life.

6319 Stoney Pt, 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

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

$560,000

3 Beds ⋅ 2 Baths ⋅ 22604209 MLS

New Construction twin home on Hole #9 of The Lakes Golf Course near Lake Madison. 3 beds, 2 baths, and oversized, fully finished 2 stall garage. In floor heat throughout the twin home including the garage. Primary suite is large with golf course views, a double vanity, large walk-in tiled shower with two heads and sizeable walk in closet. The kitchen/dining and living room is an open concept with lots of natural light. Quartz tops throughout the twin home including the bathrooms and kitchen includes tiled backsplash. 6 foot island in kitchen with pendant lighting. Plenty of storage throughout with cabinets in the mudroom off the garage and in the laundry room along with closet organization in all closets. There is a slider off the dining room to a covered patio with great views of the hole number 9 fairway. Anderson windows throughout. Luxury vinyl plank flooring throughout. Cedar ceiling in entryway and ceiling on the covered patio. Lawn is sodded and includes underground sprinkler and rock around the home. The HOA takes care of streetlights and includes a community park with a play system, sand volleyball, pickleball, a dock on Round Lake and a shelter for only $150 a year. The roads are maintained by a Road District for $600 a year that is assessed through property taxes.

23748 461a Ave Unit 2, Wentworth

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

$560,000

3 Beds ⋅ 2 Baths ⋅ 22604208 MLS

New Construction twin home on Hole #9 of The Lakes Golf Course near Lake Madison. 3 beds, 2 baths, and oversized, fully finished 2 stall garage. In floor heat throughout the twin home including the garage. Primary suite is large with golf course views, a double vanity, large walk-in tiled shower with two heads and sizeable walk in closet. The kitchen/dining and living room is an open concept with lots of natural light. Quartz tops throughout the twin home including the bathrooms and kitchen includes tiled backsplash. 6 foot island in kitchen with pendant lighting. Plenty of storage throughout with cabinets in the mudroom off the garage and in the laundry room along with closet organization in all closets. There is a slider off the dining room to a covered patio with great views of the hole number 9 fairway. Anderson windows throughout. Luxury vinyl plank flooring throughout. Cedar ceiling in entryway and ceiling on the covered patio. Lawn will be sodded and includes underground sprinkler and rock around the home. The HOA takes care of streetlights and includes a community park with a play system, sand volleyball, pickleball, a dock on Round Lake and a shelter for only $150 a year. The roads are maintained by a Road District for $600 a year that is assessed through property taxes.

23748 461a Ave Unit 1, Wentworth

Courtesy of Tom Schwebach from Schwebach Realty.

$439,500

4 Beds ⋅ 4 Baths ⋅ 22604162 MLS

Here is the country hide-away the you've been searching for! Spacious ranch home with 4 bedrooms and 3.5 baths, many recent improvements including shingles, siding, windows, doors, decks, furnace and ac. 2520 square feet finished featuring master suite, main floor laundry, formal dining, vaulted ceilings, newer flooring and paint. The front deck and back wraparound deck are newer composite material and includes a covered 21 x 12 area. Above ground heated pool too! Lot is 3 acres with nice shelter to the North and West. There are numerous fruit trees and an asparagus patch. The shed is 36 x 30 with cement floor and a separate woodworking area that is insulated and has a wood burner. There is extra storage in the 12 x 30 lean to. Also includes a 10 x 16 greenhouse. You'll love it!

24253 467a Ave, Dell Rapids

Courtesy of Justin Garry from Hegg, REALTORS. OFFICE: 605-336-2100

$675,000

3 Beds ⋅ 2 Baths ⋅ 22603657 MLS

Welcome to 6630 Peninsula Point, a delightful lakefront retreat nestled along the pristine shores of Lake Madison. This charming single-family cabin blends rustic warmth with modern comfort, offering the perfect setting for year-round living or a relaxing seasonal getaway. The main cabin features two comfortable bedrooms, a full bathroom, and an inviting open-concept kitchen and living area designed to capture beautiful lake views. Spanning the entire lakeside frontage is a wonderful four-season room, providing the ideal space to unwind, entertain, or simply enjoy the peaceful scenery in every season. Just steps away, the bunkhouse adds valuable flexibility with an additional bedroom, a laundry area, and a second bathroom—perfect for guests or extended stays. Attached to the bunkhouse is a single-stall garage, ideal for storing a vehicle or all your lake toys. The property also includes a carport and an extended-length driveway, offering ample parking for family and friends. Out toward the water, you’ll step onto a spacious composite deck overlooking one of the best sandy beaches on the entire lake. Whether you're swimming, catching some rays, or enjoying evening lakeside gatherings, this shoreline is truly exceptional. In additon to the property, Peninsula Park, which includes the open grassy area that hosts one of the best Independence Day fireworks shows annually also has a community picnic shelter you can use for you and your guests! With its serene setting, beautiful views, and the peaceful charm of Peninsula Point, this cabin is a hidden gem for anyone looking to embrace authentic lakeside living (and have a front row seat to the best fireworks display on Independence Day!)

6630 Peninsula Pt, Wentworth

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