Explore Chesterton, IN Homes for Sale

Waterfront Homes for Sale in Chesterton, IN

Advanced Search Market Reports Home Value Connect

Welcome to your dedicated resource for waterfront homes for sale in Chesterton, IN. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesterton, IN agent, Listing Leaders specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the waterfront properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< Back to all Homes for Sale in Chesterton, IN

Search Chesterton, IN by Lifestyle

All Waterfront Homes for Sale in Chesterton, IN

4 Beds ⋅ 3 Baths

Refined updates and timeless design come together in this exceptional Sand Creek residence, where light-filled interiors and thoughtfully curated finishes create an atmosphere of warmth and sophistication. At the heart of the home, the beautifully reimagined living space is anchored by a stunning new fireplace, complemented by modern LED recessed lighting that enhances the home's open, inviting feel. Three fully renovated bathrooms showcase quality craftsmanship and contemporary style, including an impressive primary en suite with a freestanding soaking tub, oversized tiled walk-in shower, dual-sink vanity, and skylight that creates a bright, spa-like atmosphere. The refreshed front entry and updated laundry room add both elegance and everyday functionality. The exterior is equally impressive, featuring premium James Hardie siding, new gutters, professionally designed landscaping, and tasteful exterior lighting that highlight the home's architectural character day and night. With over 3,000 square feet, four bedrooms, and three bathrooms, this residence offers generous spaces for both entertaining and quiet moments alike. Nestled within the prestigious Sand Creek community, enjoy a lifestyle surrounded by beautifully maintained streets, championship golf, scenic ponds, walking paths, and convenient access to Lake Michigan, the South Shore Line, and major expressways.

1650 Hogan Avenue, Chesterton

2 Beds ⋅ 2 Baths

Welcome Home! This 2 Bedroom 1.75 Bath main floor condo, has been meticulous updated and is ready for a new owner. Inside you will find newer flooring, kitchen cabinets, countertops, bathrooms, as well as newer stainless steel kitchen appliances. Main floor living at its finest! Outside you will find a patio that overlooks a large pond. This home is complete with a 1 car garage , with shelving for your storage needs. No need to worry about the exterior maintenance, grass cutting, snow removal, water and sewer bills. Those are all taken care for you through the Association. Just move right in!

1913 David Drive, Chesterton

4 Beds ⋅ 4 Baths

Timeless elegance defines this stately all-brick residence, perfectly positioned on a rare .69-acre pond lot within the prestigious gated, golf course community of Sand Creek. Backing to tranquil water with desirable southern exposure, this exceptional property is filled with natural light while offering peaceful views from two rear patios. Designed for both comfortable living and effortless entertaining, the main level showcases rich hardwood flooring, tray ceilings, formal living and dining rooms, and a private office with extensive custom built-ins. The chef's kitchen is beautifully appointed with commercial-grade stainless steel appliances, including a newer Wolf range, Thermador dishwasher, Viking refrigerator, double ovens, two sinks, abundant cabinetry, and a spacious pantry. The adjoining keeping room features a second fireplace and wet bar, creating an inviting gathering space. The main-floor primary suite offers a spacious walk-in closet and a beautifully remodeled spa-inspired bath. Upstairs are three generously sized bedrooms, including one with a private ensuite and two connected by a Jack-and-Jill bath. An oversized upper-level family room with two built-in desks provides flexible living space while overlooking the pond. The unfinished basement offers endless possibilities for future expansion. Recent improvements include a new roof (2021), new HVAC system, backup generator, tankless water heater, updated electrical, smart sprinkler system, remodeled primary bath, new lighting throughout, and a stunning motorized chandelier lift in the grand foyer for effortless maintenance. With its timeless architecture, exceptional craftsmanship, expansive lot, picturesque pond setting, and impressive list of upgrades, this remarkable home offers a rare opportunity to own one of Sand Creek's most distinguished properties.

1712 Snead Avenue, Chesterton

3 Beds ⋅ 4 Baths

This exceptional all-brick ranch offers over 4,200 finished square feet of thoughtfully designed living space. A traditional floor plan welcomes you with a gracious foyer, rich Cherry hardwood floors, and crown molding that flow throughout the main living areas. The library/office--originally designed as a third main-floor bedroom--offers flexibility for work or additional guest accommodations. Formal living with elegant fireplace and dining room with convenient service bar, create an inviting setting for entertaining. The kitchen is appointed with stainless steel appliances and an island workspace and opens seamlessly to the breakfast room with access to the screened porch and adjoining keeping room featuring a slanted ceiling and bay windows that fill the space with natural light. Privately situated on the opposite side of the home, the bedroom wing includes a spacious primary suite with tiled shower, dual vanities, and walk-in closet, along with a guest bedroom featuring its own full ensuite bath. The walk-out lower level expands the home's versatility with a large great room anchored by a double-sided fireplace, wet bar with granite countertops, family room, game room, private bedroom suite, and a dedicated workroom ideal for planting, painting, crafts, or woodworking. Completing the property are a two-car garage and separate golf cart garage, perfectly suited for an active lifestyle. Enjoy the ease of a low-maintenance lifestyle while retaining the spacious feel and individuality of a traditional residence. The association provides lawn care and fertilization, irrigation, snow removal, and maintenance of common areas--allowing more time to enjoy life and less time worrying about exterior upkeep.

1340 Cantigny Court, Chesterton

4 Beds ⋅ 3 Baths

Spacious and inviting 4-bedroom, 2.5-bath home conveniently located near the heart of Chesterton, just minutes from the beautiful Indiana Dunes National Park, shopping, dining, and more! This well-maintained home offers plenty of room to spread out with a large living room, formal dining room, and an oversized eat-in kitchen that opens to the cozy family room featuring a gas fireplace. Main floor laundry adds everyday convenience. Upstairs you'll find 4 generously sized bedrooms, including a spacious primary suite with a large closet and attached full bath. Recent updates include freshly repainted interior, newer carpet, and a new garage roof. Great space, great location, and ready for you to move right in!

378 Ballenisle Court, Chesterton

4 Beds ⋅ 5 Baths

Welcome to your private Northwest Indiana retreat in desirable Jackson Township--where space, luxury, and nature come together on just over 15 stunning acres. This all-brick estate offers the perfect blend of elegance and outdoor adventure, featuring 4 bedrooms and 5 bathrooms, thoughtfully designed for both everyday living and unforgettable entertaining. Inside, you'll find a generously sized kitchen with granite counters and stainless appliances, including a 6-burner cooktop with a griddle. 4 bedrooms include a spacious primary suite that serves as a true sanctuary, complete with a large en suite bath and plenty of room to unwind. Two additional bedrooms also feature private en-suite bathrooms, providing comfort and privacy for family or guests. The home offers many living spaces filled with natural light, including a beautiful sunroom with a hot tub--the perfect place to relax year-round. Conveniently located nearby is a dedicated bathroom designed to service the pool area. Step outside and experience a property that truly feels like a personal resort. Enjoy summers by the in-ground pool, host gatherings on the expansive deck, or explore your own private walking trails and mature woods. The stocked pond adds to the peaceful setting and creates the perfect spot for fishing, quiet reflection, or simply taking in the scenery. The unfinished basement provides incredible opportunity for future expansion--whether you envision a home theater, gym, additional living space, or guest quarters. Located in the highly sought-after Duneland School District, this property offers the perfect balance of privacy and convenience. Just minutes away, you'll find the breathtaking beaches and trails of the Indiana Dunes National Lakeshore, while the South Shore Railway provides an easy commute to downtown Chicago.

1137 N 475 E, 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.