ChesterAre Homes under $500,000

Welcome to Chester Area, South Dakota, a charming community nestled in Lake County, where small-town warmth meets exceptional educational opportunities! This delightful region boasts a highly regarded school district, known for its commitment to academic excellence and fostering a supportive learning environment. Chester Area School District is dedicated to providing students with a well-rounded education, featuring a variety of extracurricular activities, advanced placement courses, and dedicated faculty who prioritize student success.

Families looking to settle down in this picturesque area will be thrilled to discover a range of beautiful homes available for under $500,000. Whether you’re seeking a cozy cottage or a spacious family home, Chester Area offers diverse options that cater to various lifestyles and budgets. These properties often come with generous yards, perfect for outdoor activities and family gatherings, and many are conveniently located near schools, parks, and local amenities.

Living in Chester Area means enjoying the best of both worlds: the tranquility of rural life combined with a strong sense of community. Residents take pride in their town, where friendly neighbors and local events create a close-knit atmosphere. With easy access to nearby lakes and recreational areas, outdoor enthusiasts will find plenty of opportunities for fishing, hiking, and enjoying nature.

If you’re considering a move to Chester Area, South Dakota, you’ll not only find a wonderful place to call home but also an environment that nurtures growth and learning for your family. Explore the available homes today and discover the charm and community spirit that make Chester Area a great place to live!

Newest ChesterAre Homes under $500,000

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 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 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 Randy Rozeboom from Harr & Lemme Real Estate. Cell: 605-366-8889

$419,900

3 Beds ⋅ 2 Baths ⋅ 22603563 MLS

Exceptional and impeccable best describes this 3 bedroom, 2 bath ranch twinhome with heated triple garage. Located between Round Lake and Lake Madison and just blocks from the Lakes Golf Course and Restaurant. Open floor plan in the kitchen/living room area. Kitchen has stainless appliances, large center island and beautiful cabinets. Dining area features sliders to a 10 x 25 patio with roll out awning. Primary bedroom has a 3/4 bath with double vanity and walk-in closet. Convenient main floor laundry with utility sink and new cabinetry. Oversized garage has heater, epoxy floor, drain, hot & cold water and pull down screens for both garage doors. Gorgeous backyard with mature trees and meandering canal. HOA is $150.00 per year for street lights, community park, pickle ball courts, sand volleyball and playground. Roads are maintained by a Road District and assessed on Real Estate taxes at $600 per year.

128 Silver Creek Dr, Wentworth

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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 Homes under $500,000

Newest ChesterAre Homes under $500,000

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