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Homes for Sale with a Basement in Chesterton, IN

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Welcome to your dedicated resource for homes for sale with a basement 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 with a basement properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Homes for Sale with a Basement in Chesterton, IN

3 Beds ⋅ 3 Baths

Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Duneland trail. The Bassett Grove is PROPOSED CONSTRUCTION on LOT 30.. A 2 story with primary en suite on main level and 2 separate guest bedrooms upstairs with full bathroom. Standard finished include Luxury vinyl Plank flooring, quartz or granite countertops, custom cabinets and a spa like primary ensuite. Numerous options to choose from and we invite you to visit the design center at 2179 W 1100 to start your new build!

2274 Pradera Trail, Chesterton

4 Beds ⋅ 2 Baths

Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Duneland trail. The Windmill model is PROPOSED CONSTRUCTION on Lot 30. A sprawling ranch with an impressive great room and boasts 4 bedrooms and a full unfinished basement to give you 4,000 sqft of potential living space. Standard finished include Luxury vinyl Plank flooring, quartz or granite countertops, custom cabinets and a spa like primary ensuite. Numerous options to choose from and we invite you to visit the design center at 2179 W 1100 to start your new build!

2246 Pradera Trail, Chesterton

3 Beds ⋅ 2 Baths

Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully designed living space in The Preserve. Situated on a premium homesite bordering protected wetlands, this home offers serene views, added privacy, and a peaceful natural setting. The open-concept floor plan seamlessly connects the kitchen, dining area, and great room, extending to a private rear deck perfect for outdoor dining, relaxing, or entertaining. Large Andersen windows and elevated ceilings fill the home with natural light, creating a bright atmosphere. The well-designed layout includes three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or additional living space. The kitchen blends timeless style and everyday functionality with classic shaker cabinetry, stainless steel appliances, a generous pantry, large island, and abundant counter space. The spacious primary suite offers a private retreat with a dual-sink vanity, beautifully tiled walk-in shower, expansive walk-in closet, and an additional oversized closet for exceptional storage. A standout feature is the unfinished daylight basement overlooking the protected wetlands, complete with full-size windows that provide abundant natural light. Future expansion offers endless possibilities for a recreation room, home gym, media room, guest suite, home office, or additional bedrooms. Plumbing is already roughed in for a future full bathroom, making it easy to customize as your needs evolve. Premium features include 42-inch soft-close cabinetry, LVP flooring throughout the main living areas, Andersen windows, a high-efficiency HVAC system, professionally designed landscaping, and a two-car garage. Located within The Preserve, a thoughtfully planned community spanning 90 acres of protected natural landscape, residents enjoy privacy and convenience just 40 miles SE of Chicago, with easy access to shopping, dining, highly rated schools, commuter routes, the South Shore Line, and Indiana Dunes.

1002 Preserve Lane, Chesterton

3 Beds ⋅ 2 Baths

Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully designed living space in The Preserve. Set on a premium homesite overlooking a wooded natural buffer, this home offers peaceful views and a tranquil setting. The open-concept floor plan seamlessly connects the kitchen, dining area, and living room, extending to a private rear deck overlooking the wooded backdrop, perfect for relaxing or entertaining. Large Andersen windows and elevated ceilings fill the home with natural light, creating a bright, airy atmosphere throughout. Designed for both style and functionality, the kitchen features classic shaker cabinetry, stainless steel appliances, a generous pantry, large island, and abundant counter space for everyday living and entertaining. The spacious primary suite offers a private retreat with a dual-sink vanity, tiled walk-in shower, expansive walk-in closet, and an additional oversized closet for exceptional storage. A standout feature is the unfinished daylight basement overlooking the natural wetlands, complete with full-size windows that provide abundant natural light. Designed for future expansion, the lower level can easily become a recreation room, home gym, media room, guest suite, home office, or additional bedrooms. Plumbing is already roughed in for a future full bathroom, providing even more flexibility to customize the space. Premium features include 42-inch soft-close cabinetry, LVP throughout the main living areas, fireplace, Andersen windows, a high-efficiency HVAC system, professionally designed landscaping, and a finished two-car garage. Buyers also have the opportunity to personalize select interior finishes during construction. Located within The Preserve, a thoughtfully planned community spanning 90 acres of protected natural landscape, enjoy privacy and convenience just 40 miles SE of Chicago, with easy access to shopping, dining, highly rated schools, commuter routes, the South Shore Line, and Indiana Dunes.

1003 Preserve Lane, Chesterton

3 Beds ⋅ 4 Baths

Welcome to 1429 Calais Court, a beautifully maintained paired home nestled in the CHATEAUX DU CHAMBORDE area in the sought-after Sand Creek community of Chesterton. Offering the perfect blend of comfort, convenience, and low-maintenance living, this home is ideal for anyone looking to enjoy a relaxed lifestyle in one of Northwest Indiana's premier neighborhoods. Step inside to find a bright, inviting floor plan with spacious living areas, abundant natural light, and a layout designed for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living spaces, creating a warm and welcoming atmosphere. The generous primary suite provides a private retreat, while additional living space offers flexibility for guests, a home office, or hobbies. Enjoy your morning coffee or unwind in the evening on your private patio while taking in the peaceful surroundings. Located within the prestigious Sand Creek community, you'll appreciate easy access to golf, walking paths, shopping, dining, top-rated Duneland schools, and the beautiful Indiana Dunes National Park and Lake Michigan shoreline. With convenient access to major highways and the South Shore Line, commuting to Chicago is also within easy reach.

1429 Calais Court, Chesterton

4 Beds ⋅ 4 Baths

Nestled on a private, wooded 4.5-acre lot in Chesterton's Jackson Township within the Duneland School District, this captivating multi-level home blends distinctive mid-century character with more than 4,300 square feet of versatile living space. Floor-to-ceiling windows, clean architectural lines, serene wooded and open views, and a year-round flowing creek create a peaceful setting that feels timeless and connected to nature. The main level offers a sunlit living room anchored by a dramatic Wisconsin Cascade stone fireplace, a formal dining room with updated lighting, and a fully equipped kitchen with new stainless steel appliances, updated fixtures, and a reverse osmosis water system. Upstairs, you'll find three bedrooms and two full baths--including a hall bath with radiant heated floors--plus a flexible office/flex space adjoined to the primary suite that can easily serve as a nursery, private sitting room, or expansive second walk-in closet. The main and lower levels provide additional living and entertaining space, featuring a fourth bedroom, half bath, family room with a second stone fireplace, and a spacious recreation room. Multiple bedrooms open to three private decks, while a screened porch overlooks the scenic grounds. A dedicated heated and cooled workshop with a private exterior entrance adds even more functionality. Recent improvements include a newer well pressure tank, Presby septic system, radon mitigation system, roof on the detached garage, kitchen reverse osmosis system, and an owned water softener. Outside, the property is a true retreat with parklike grounds, five garage bays, raised garden beds, fruit-bearing apple trees, mature woods, and picturesque outdoor spaces. All of this is located just minutes from downtown Chesterton, Indiana Dunes National Park, nearby beaches, and the South Shore Line with convenient access to Chicago.

1147 N 400 E, Chesterton

4 Beds ⋅ 4 Baths

Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining rental unit, now vacant, includes 2 bedrooms and 2 bathrooms, allowing you to choose the tenants and rents. The 455 side has a brand new air conditioner and new appliances last year. New windows were installed in 2025. Both units enjoy large, private backyards perfect for relaxing, entertaining, or gardening. Conveniently located just minutes from the beautiful beaches of Lake Michigan, charming downtown Chesterton, and the renowned European Market, this property also offers an easy commute with quick access to the South Shore Line and I-94, putting downtown Chicago within approximately 45 minutes. Whether you're looking to reduce your housing costs or expand your investment portfolio, this property offers the perfect combination of comfort, convenience, and income potential.

455 Woodlawn Avenue, Chesterton

4 Beds ⋅ 3 Baths

Only 3 years young- this new construction build was completed by one of NWI's most prestigious builders in the desirable Preserve neighborhood known for its thick tree lines of protected land! A backyard oasis is already complete for you and makes this home the best value you could be looking for in Chesterton! It's not everyday you see a backyard like this - inground pool with automatic safety cover, putting green and large stamped concrete patio for backyard dinners. Beautiful mature landscaping and surrounded by trees on 2 sides. The home sits on a quiet cul de sac and is a show stopper with high end finishes. A 2 story foyer greets you and welcomes you into the 2 story great room with a gas fireplace at the heart. A bright kitchen overlooking your backyard oasis and featuring quartz countertops with a six drawer island, walk in pantry with built in shelving and including a mini fridge. Off kitchen dining for casual family dinners and a formal dining for entertaining. An office, half bath and bedroom finish the main level living with mudroom access from the garage to kitchen. Upstairs you will find a beutifully appointed primary en suite with wainscotting, walk in closet with custom built in organizers, walk in tiled shower with frameless glass doors, and double vanity. 2 other bedrooms complete the upstairs along with UPSTAIRS LAUNDRY for added convenience. And last but not least a full unfinished basement of additional 1300 potential living space with 9 ft ceilings for future expansion and includes egress window for future 5th bedroom and rough in plumbing for future 4th bathroom. This home has everything you are looking for and is 15 mins from train station for easy to commute to Chicago, 10 mins from Chesterton downtown with local restaurants, coffee shops and the famous European farmers market! Award winning Duneland School system with the high school and the popular Dogwood park only 4 minutes! Taxes will be lower with new owners homestead exemption!

18 Blue Grass Way, Chesterton

4 Beds ⋅ 3 Baths

Introducing the Aspen on Lot 4 in 1100 Woods! PROPOSED CONSTRUCTION***** Located in the heart of Chesterton across from Dogwood Park and the Prairie Duneland Trail. The Aspen model is ideal for those looking for a primary ensuite on main level with walk in closet, a large kitchen island for extra seating to gather, and plenty of storage. Kitchen over looks your great room and dining for an open concept.

2350 Pradera Trail, Chesterton

3 Beds ⋅ 2 Baths

Introducing The Chestnut - A Brand New Custom Ranch Floorplan on Lot 6! This thoughtfully designed ranch offers the perfect blend of style and function, featuring an open-concept layout with a spacious great room with optional fireplace, dining area, and kitchen complete with quartz countertops and upgrade options available. The primary ensuite provides a private retreat, while generous guest bedrooms offer comfort and versatility. Enjoy the flexibility of a partial unfinished basement--ideal for future living space or ample storage. Located in the heart of Chesterton, this home is being built by one of the area's most highly regarded custom builders. Now is the perfect opportunity to personalize your selections and bring your dream home to life!

2420 Pradera Trail, Chesterton

3 Beds ⋅ 2 Baths

Welcome home to The Prescott in 1100 Woods! PROPOSED CONSTRUCTION on lot 16- one of the last tree lined lots of the subdivision. Large 2000 sqft ranch with unfinished lookout basement with 3 car garage is the perfect blend of main level living with room to expand to almost 4000 sqft when finishing the basement. The view from your living room and deck is only of trees giving you a beautiful feeling of seclusion while being close to everything Chesterton has to offer! Across the street is the popular Dogwood Park and Prairie Duneland trail. If you are a waking, running or biking enthusiast this is the perfect location for you! Inside you will find a versatile floorplan that you can customize and select all finishes. Primary bedroom features spa like bathroom and walk in closet. 2nd and 3rd bedrooms are good sized and there is a bonus flex room perfect for an office or possible 4th bedrooms.

2431 Pradera Trail, Chesterton

Turnkey opportunity in the heart of downtown Chesterton -- this fully renovated 1,744 SF, two-story restaurant building is ready for its next concept. The property features a full commercial kitchen with walk-in cooler, two levels of indoor dining, and a bathroom on each floor, plus a spacious courtyard and deck offering additional outdoor dining. Extensive top-to-bottom renovations include new HVAC, restored hardwood floors, new windows, gutters, soffit, fascia, siding, shutters, corbels, bathrooms, ceiling tiles, and lighting fixtures -- delivering a move-in-ready space with modern systems and timeless character. Situated in a highly walkable downtown corridor surrounded by shops and restaurants, the location offers excellent visibility and foot traffic, with the added draw of close proximity to Indiana Dunes National Park and convenient access to major highways. Call today to schedule your property tour.

321 Broadway Avenue, Chesterton

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