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Single Family Homes for Sale in Chesterton, IN

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

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All Single Family Homes for Sale in Chesterton, IN

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

4 Beds ⋅ 2 Baths

Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

2342 Westwood Lane, 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 ⋅ 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

2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton

5 Beds ⋅ 5 Baths

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

229 E Morgan Avenue, Chesterton

4 Beds ⋅ 3 Baths

FORE! Welcome to this exquisite Cape Cod residence in the prestigious Estates of Sand Creek subdivision. Enjoy breathtaking views of the 4th hole of the Marsh Course at Sand Creek Country Club from the comfort of your own home, without being directly on the course. This spacious 4-bedroom, 2.5-bath home offers over 2,400 square feet of well-appointed living space. Open concept living with vaulted and cathedral ceilings allow for a plethora of natural light to shine throughout. The kitchen and bathrooms feature elegant quartz countertops, owner added a maintenance free gas fireplace with white fireglass, and a new roof that provides peace of mind. The unfinished full basement with 9-foot ceilings offers incredible potential for expansion, perfect for a family room, home gym, theater, or additional bedrooms. Outdoor living shines with a flagstone patio and permanent ceramic gas firepit, mesmerizing green fireglass, ideal for entertaining or quiet evenings. Residents enjoy resort-style amenities within the Sand Creek community, including access to championship 27-hole golf with 3 (9 hole )courses, a beautiful pool complex, fitness center, tennis courts, and fine dining at the clubhouse, all set among scenic ponds and rolling terrain. Conveniently located just minutes from the Indiana Dunes National Lakeshore, Lake Michigan's pristine beaches, the South Shore Train Station, and major highways. Top-rated Duneland School District completes this exceptional package. This is more than a home -- it's a lifestyle.

961 Monterey Drive, Chesterton

3 Beds ⋅ 3 Baths

PROPOSED CONSTRUCTION-Welcome to the Sonoma in Easton Park! This stunning custom-built, 1.5-story home offers over 2,100 square feet of luxury living with 3 bedrooms, 2.5 baths and a 3-car garage, all situated on a desirable corner lot. Step inside to a spacious foyer featuring a private office and convenient half bath before entering the impressive open-concept living space. The great room showcases beautiful hardwood floors, a custom fireplace, solid-core doors, an upgraded trim package and quality craftsmanship throughout. The kitchen is designed for both everyday living and entertaining, featuring quartz countertops, custom cabinetry, stainless steel appliances and a large walk-in pantry. The main-level primary suite offers a relaxing retreat with double sinks, a soaking tub and a spacious walk-in closet. Upstairs, you'll find two additional bedrooms...each with its own walk-in closet...a full bath, and a huge loft offering flexible space for a second living area, playroom, or entertainment space. Additional highlights include energy-smart features, zoned high-efficiency HVAC, a whole-home humidifier, fresh air intake, R-20 basement insulation, an egress window for a possible future bedroom and rough-in plumbing for a future bathroom. Located in the desirable Easton Park neighborhood, this home offers convenient access to Indiana Dunes National Park, the South Shore Line, major expressways, shopping, dining, and award-winning schools. Experience luxury, quality craftsmanship and thoughtful design in the Sonoma!

801 Ashwood Lane, Chesterton

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