Chesterton Homes with In Ground Pool features

Welcome to Chesterton, Indiana, a charming town nestled in Porter County, where small-town charm meets modern convenience. With its picturesque landscapes and a close-knit community, Chesterton is an ideal place for families and individuals looking to enjoy a serene lifestyle while still being close to urban amenities. Known for its vibrant downtown area filled with delightful shops, restaurants, and local events, this town offers a unique blend of historical charm and contemporary living.

One of the standout features of homes in Chesterton is the presence of in-ground pools, perfect for those warm Indiana summers. Imagine stepping into your own backyard oasis, where you can unwind with family and friends, host summer barbecues, or simply relax by the water with a good book. These homes not only provide a private retreat but also enhance your lifestyle, allowing for endless opportunities for recreation and relaxation right at your doorstep.

Chesterton is also conveniently located near the stunning Indiana Dunes National Park, offering residents a wealth of outdoor activities, from hiking and biking to swimming and sunbathing on the pristine beaches of Lake Michigan. The local schools are highly rated, making this community a fantastic choice for families seeking quality education for their children.

Whether you’re looking for a cozy starter home or a spacious family residence, Chesterton has something for everyone. Explore the delightful homes with in-ground pools and discover your own slice of paradise in this captivating Indiana town!

Newest Chesterton Homes with In Ground Pool features

$679,000

4 Beds ⋅ 3 Baths ⋅ 843120 MLS ⋅ 2,409 SqFt. ⋅ Madison Young

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

Listing courtesy of Madison Young from Brokerworks Group.

$875,000

5 Beds ⋅ 5 Baths ⋅ 842756 MLS ⋅ 6,360 SqFt. ⋅ Alexis Metcalf

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

Listing courtesy of Alexis Metcalf from Seramur Properties, LLC.

$1,350,000

4 Beds ⋅ 5 Baths ⋅ 835684 MLS ⋅ 5,809 SqFt. ⋅ Lisa Gaff

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

Listing courtesy of Lisa Gaff from White Hat Realty Group, LLC.

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Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.