Chesterton, IN Real Estate Search

Chesterton, IN Homes between $250,000 and $300,000 for Sale

Our website features the best real estate search for homes between $250,000 and $300,000 available in Chesterton, IN and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Chesterton, IN real estate market? Sign up for a Chesterton, IN Real Estate Market Report to see what’s active, under contract, and sold!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Chesterton, IN Homes between $250,000 and $300,000 for Sale

3 Beds ⋅ 3 Baths

Welcome to this charming 3-bedroom, 2 1/2 bath ranch nestled in the established Chestnut Hill neighborhood! This inviting home offers comfortable one-level living with a spacious eat-in kitchen, providing plenty of room for everyday meals and entertaining. A 2-car garage offers convenient parking and additional storage space. The fenced-in backyard provides a wonderful space for outdoor enjoyment, pets, gardening, or relaxing with family and friends. With three bedrooms, two full bathrooms, and a desirable ranch layout, this home offers both convenience and functionality in a well-established neighborhood. Don't miss the opportunity to make this Chestnut Hill gem your new home!

610 Fox Point Drive, Chesterton

2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton

3 Beds ⋅ 2 Baths

Back on market at no fault of seller! Welcome to 252 S 21st St in Chesterton! This well-maintained home offers valuable updates, flexible living space, and outstanding garage/storage options, all tucked away at the end of a cul-de-sac. When you walk through the front door, you'll notice the vinyl flooring and open floor plan, with the floors flowing naturally into the kitchen and dining area. The renovated bathrooms provide a modern, updated feel alongside the main-floor bedrooms. Major improvements include a new roof, new air conditioner, new furnace, new gutters, and a newer sump pump, giving buyers added peace of mind. The home also features a partially finished basement with a family room, bedroom, and bathroom -- perfect for guests, hobbies, work-from-home needs, or additional living space. Out back, enjoy a deck overlooking the yard, ideal for relaxing, grilling, or entertaining. The property also stands out with two detached garages providing a total of four garage spaces, offering excellent room for vehicles, storage, tools, recreational equipment, or workshop potential. Conveniently located in Chesterton, this home combines practical updates, extra space, rare garage capacity, and a quiet cul-de-sac setting. Schedule your showing today!

252 S 21st Street, Chesterton

3 Beds ⋅ 1 Baths

ONLY 10 to 15 MINUTES to LAKE MICHIGAN'S SANDY BEACHES! ENJOY PEACE, QUIET, & SERENITY from your charming 3-bedroom ranch with a detached 1.5-car garage plus off-street parking! This lovely home is set back, away from the roadway. Enjoy soothing, natural views from your back yard & screened porch. Set on a spacious landscaped lot, next to a private, wooded area, this unique home boasts low-maintenance exterior, spacious open living room/dining room combo (great for entertaining! And the master bedroom will accommodate your king-sized bed)! Newer lighting; freshly painted in soft neutrals to match any decor! All appliances stay. Two storage sheds. Close to everything: lakes, parks, trails, shopping, restaurants! This well-maintained property is being sold as is. Schedule your showing today. Welcome home!

704 S 22nd Street, Chesterton

3 Beds ⋅ 2 Baths

Nice, solid all-brick ranch on a desirable corner lot directly across from the high school! This well-maintained home features a spacious eat-in kitchen with newer luxury vinyl hardwood flooring, a formal dining room, and all newer stainless steel appliances included. A built-in doggie door and sliders lead to a privacy-fenced backyard--perfect for pets and entertaining. Major updates include a new roof and sump pump in 2023, plus added washer and dryer hookups in the bathroom for extra convenience. Fantastic location close to schools, shopping, expressways and amenities!

1749 Green Meadow Lane, Chesterton

Presenting one of the final opportunities to own a GOLF COURSE lot in the highly sought-after gated community of Sand Creek. This spacious half-acre lot offers stunning views and direct frontage on the renowned 27-hole championship golf course, providing an ideal setting to design and build the custom home of your dreams. Located within one of Northwest Indiana's most prestigious neighborhoods, Sand Creek offers a truly elevated lifestyle. Residents enjoy access to a private clubhouse, upscale dining, fitness facilities, tennis courts, and a vibrant calendar of social and recreational events all within a secure, beautifully maintained environment. This lot is fully shovel-ready with utilities on site and is surrounded by some of the area's finest custom homes. With very few golf course lots remaining, this is a rare chance to become part of a community known for elegance, privacy, and timeless appeal. Don't let this opportunity pass you by your dream home and the coveted Sand Creek lifestyle await.

1441 Nelson Drive, Chesterton

Gorgeous lot located in the gated Sand Creek community and ready for your dream home! Enjoy a beautiful setting with added privacy and access to neighborhood amenities. Situated in the highly sought-after Duneland School District, this is a fantastic opportunity to build in a desirable location. Bring your builder and start planning today!

1711 Littler Drive, Chesterton

Location, Location, Location. Two adjacent Commercial building sites totaling 1.7 acres in established, fast growing Chesterton business park. Excellent location just South of downtown, off Calumet Rd., West of Highway 49 and quick access to the Indiana Toll Road and Highway 94. Utilities to the site, favorable B-3 Business Zoning.

123 & 127 Venturi Drive, Chesterton

3 Beds ⋅ 2 Baths

Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning trails and beaches of Indiana Dunes National Park, this 1,977-square-foot haven offers 3 bedrooms, 2 bathrooms, and effortless access to Chicago commutes--blending small-town charm with big-city convenience in the highly rated Duneland School District. From the moment you arrive, the home's warm light yellow siding and inviting deck beckon you into a world of timeless elegance. Step inside to a light-filled living room with dramatic cathedral ceilings, creating an open, airy retreat perfect for family gatherings. The adjacent kitchen inspires gourmet meals and connects seamlessly to the versatile den--ideal as a home office or guest space. Enjoy a full main-floor bathroom, convenient laundry/mud room, and direct access to the expansive covered patio, with the sprawling backyard perfect for barbecues or serene views. Upstairs, unwind in the luxurious primary bedroom suite with a spa-like en-suite bathroom and generous closet. The adaptable loft offers endless possibilities, complemented by a spacious second bedroom. The full unfinished basement awaits your vision as a media room or workshop, alongside a dedicated office. Modern comforts include central air, natural gas heating, municipal utilities. This isn't just a house--it's a legacy of tranquility and adventure. With historic soul and unbeatable location, it's ready to welcome you home.

214 Woodlawn Avenue, Chesterton

Start Your Search

Updated . Information deemed reliable but not guaranteed.