ChesterAre Homes for Sale

Welcome to Chester Area, South Dakota, a vibrant and welcoming community that perfectly balances small-town charm with modern conveniences. Nestled amidst the picturesque landscapes of the Midwest, Chester Area is not only known for its scenic beauty but also for its exceptional school district, making it an ideal place for families looking to settle down.

The Chester Area School District is dedicated to providing a high-quality education, fostering a nurturing environment where students can thrive. With a commitment to academic excellence, the district offers a variety of programs and extracurricular activities that cater to diverse interests and talents. Small class sizes ensure personalized attention, allowing teachers to engage with each student effectively. From innovative STEM programs to a strong emphasis on the arts, Chester Area schools prepare students for success, both in and out of the classroom.

For those considering relocating to this delightful area, there are numerous homes for sale that cater to a range of preferences and budgets. Whether you’re seeking a cozy starter home, a spacious family residence, or a charming property with a bit of land, Chester Area has something for everyone. The real estate market here is thriving, with properties that reflect the warmth and character of the community.

Living in Chester Area means enjoying a peaceful lifestyle, surrounded by friendly neighbors and a strong sense of community. With its excellent school district and beautiful homes, Chester Area is not just a place to live; it’s a place to call home. Come discover the charm of Chester Area, SD, and find your perfect home today!

Newest ChesterAre Homes for Sale

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. 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 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

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

$699,900

5 Beds ⋅ 4 Baths ⋅ 22602470 MLS

Check out this amazing home near Lake Madison and a short golf cart ride to the Lakes Golf Course! This home was moved onto a new foundation, gutted and completely updated & upgraded from top to bottom. New shingles, siding, windows, electrical, furnace, air conditioner and a new deck. As you enter the home from the covered front porch you will fall in love with the open concept of the kitchen, dining and living room area. The kitchen has white cabinets w/ solid surface counters, a pantry, large island and LVP flooring. The the dining room/living room has 10ft ceilings and living room includes an electric fireplace. There are 3 bedrooms on the main with a primary suite that includes a large bathroom, walk in onyx shower, dual sinks and walk in closet. The two other bedrooms share a pass through bath. Main floor laundry. A half bath finishes off the main floor. The basement is large and include a bar and rec area, a sizeable family room, full bath and two more bedrooms. There is access to Round Lake for jet skiing, canoeing and kayaking. HOA is $150 per year and takes care of streetlights & community park with playground, dock on Round Lake, sand volleyball court and two pickleball courts. Roads are maintained by a Road District and assessed on taxes at $600 per year.

104 Silver Creek Dr, Wentworth

Courtesy of Brad Benson from Signature Realty Group LLC.

$999,500

4 Beds ⋅ 4 Baths ⋅ 22602082 MLS

Experience the very best of lake living in this beautifully appointed 4-bedroom, 4-bath home on Lake Madison, where comfort, quality, and breathtaking views come together. From the moment you step onto the expansive deck, you'll appreciate panoramic views stretching the length of the lake, along with unforgettable sunsets that make every evening feel special. Inside, warm wood flooring and an open, inviting layout showcase the home's spectacular lake views. The spacious kitchen features solid surface countertops, a double oven, and abundant workspace for preparing meals and entertaining family and friends. Just off the main living area, the four-season porch offers a peaceful place to relax and enjoy the scenery year-round. The walk-out lower-level family room provides additional living and entertaining space with direct access to the lakeside patio. The upper-level primary suite is a true retreat, featuring an impressive 11' x 11' walk-in closet and a luxurious ensuite bathroom with heated floors and a walk-in shower. Two additional upstairs bedrooms share a full bathroom complete with a relaxing Jacuzzi tub. Designed for both relaxation and recreation, the property offers exceptional outdoor amenities. Multiple exterior storage areas provide plenty of room for lake gear, while the RV pad includes a 30-amp hookup that also accommodates Level 2 EV charging. A sprinkler system, vegetable garden, and mature apple and pear trees enhance the beautifully maintained grounds. Concrete steps lead down to a sandy beach, where the included dock offers excellent fishing, convenient boat hookups, and easy access to the water. Adding even more functionality, the concrete boathouse provides ideal storage for your boat and water toys, while a rail system with a winch-driven cart makes launching and retrieving equipment simple and convenient. The heated attached garage includes two parking stalls plus an additional heated workshop with durable tile flooring, making it an ideal space for woodworking, hobbies, or projects. The workshop is equipped with a dust collection system, and the garage also includes a 240-volt outlet suitable for Level 2 EV charging, RVs, or other 240-volt needs. This home is as efficient as it is beautiful. Recent updates include a 90% efficient three-zone gas furnace (2024), a newer central air conditioning unit (2025), and new shingles installed in 2022. Additional features include a central vacuum system, reverse osmosis water filtration, and super-insulated walls that help keep heating and cooling costs remarkably low. Conveniently located just minutes from Madison, less than 40 minutes from Sioux Falls, and just blocks from The Lakes Golf Course, this exceptional property offers the perfect balance of peaceful lakeside living and convenient access to everyday amenities. Whether you're searching for a year-round residence or an unforgettable lake retreat, this one-of-a-kind Lake Madison property delivers the lifestyle you've been waiting for.

6797 Zimmerman Dr, Wentworth

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

$1,350,000

6 Beds ⋅ 4 Baths ⋅ 22602052 MLS

Stunning 6-bedroom lakefront home on the Peninsula with sweeping water views throughout! Main-level primary suite and open-concept living with a gourmet kitchen featuring a 12-ft island, spacious dining area that comfortably seats 12, and a wall of windows facing the lake. Gorgeous sunroom with fireplace opens to a gated private courtyard, which includes a handheld outdoor shower—perfect after a day on the water. Upstairs offers 5 spacious bedrooms, multiple baths, and a versatile office/den—ideal for multi-generational living with two separate bedroom zones. Outside, enjoy a new concrete patio, fire pit, large yard, seawall, and sandy beach with no-stairs, easy water access. Heated 4-car garage. Exceptional privacy, space, and layout—perfect for entertaining. A rare lakefront gem! Move in and immediately enjoy as this home is available fully furnished!

6604 Peninsula Pt, Wentworth

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

$694,900

4 Beds ⋅ 3 Baths ⋅ 22601920 MLS

This executive walkout home overlooks the park and Hole #1 of the Lakes Golf Course, offering sweeping views of Round Lake and an unbeatable setting. With 4 bedrooms and 3 bathrooms, this property is designed for comfort, style, and year-round enjoyment. Step inside to a vaulted living room with a cozy fireplace, a spacious eat-in kitchen, and a private master suite. The lower level features a welcoming family room with a gas fireplace and a game room complete with a full kitchen and a wet bar—perfect for entertaining. Car lovers, golfers, and lake enthusiasts will appreciate the oversized 3-stall garage, providing ample space for vehicles, a golf cart, or even a boat. Outdoor living shines here with a covered deck and patio that make the most of the stunning views. Situated on a generous 105' x 142' corner lot, this home offers space, scenery, and a lifestyle you won’t want to miss. Don’t let this opportunity pass you by. Buyer not liking the oak look, then the sellers agrees to pay their licensed/professional painter to paint all kitchen and bathroom cabinets, all interior doors, and all interior millwork (baseboards, casings, trim) at the Property. Painting is limited to surfaces listed here; repairs, replacements, or staining are excluded unless agreed in writing.

45 Golf Dr, Wentworth

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