Chesterton Homes with In Ground Pool Features

Chesterton Homes with In Ground Pool Features

Welcome to Chesterton, Indiana – a charming town nestled in the heart of Porter County, where small-town allure meets vibrant community spirit. Known for its picturesque landscapes and friendly atmosphere, Chesterton offers a unique blend of suburban comfort and easy access to urban amenities. Just a stone's throw away from the stunning shores of Lake Michigan, this delightful town boasts a rich history, thriving local businesses, and a variety of recreational opportunities.

One of the standout features of homes in Chesterton is the abundance of properties equipped with in-ground pools, perfect for those hot summer days. Imagine stepping into your own private oasis, where you can relax and unwind with family and friends. These homes are designed for both leisure and entertainment, providing ample space for poolside gatherings, barbecues, and sun-soaked afternoons.

Whether you're looking for a cozy family home or a luxurious retreat, Chesterton’s real estate market offers a diverse selection of properties with stunning pool features. Enjoy the convenience of having a refreshing dip just steps from your back door, all while being surrounded by the natural beauty that Chesterton has to offer.

With its excellent schools, vibrant parks, and a strong sense of community, Chesterton is not just a place to live; it's a place to thrive. Explore the possibilities of finding your dream home with an in-ground pool in this delightful Indiana town, where every day feels like a vacation!

Newest Chesterton Homes with In Ground Pool Features

354 E 1300 N, Chesterton
$525,000
4 Beds ⋅ 2 Baths
Tucked away in Chesterton is a unique property where natural beauty, history, and opportunity come together! Spanning 11.52 acres across two separate parcels, this property features expansive open lawns, mature trees, wooded acreage, and the Calumet River winding through the back landscape. The first parcel consists of 2.35 acres and features a 4-bedroom, 1.75-bath bi-level home built in 1977. Inside, the spacious family room is highlighted by an impressive brick wood-burning fireplace with a wood stove insert and original wood accents. The kitchen offers abundant cabinetry, while the attached two-car garage provides convenience and additional storage. A backyard deck overlooks the expansive lawn framed by mature trees. The home remains largely in its original condition, offering the opportunity to update and make it your own. The second parcel consists of 9.17 acres and holds a unique piece of Chesterton history. Nestled among the trees is a 1,004-square-foot historic cottage featuring rustic wood interiors, exposed ceiling beams, and 2 fireplaces. Beyond the cottage, wooded acreage surrounds the Calumet River as it winds through the property, creating a beautiful natural setting. The cottage is in need of restoration, offering an opportunity for someone who appreciates its history and original character. From the open green spaces to the secluded wooded surroundings and historic cottage, this property offers something truly different. A rare opportunity to own 11.52 acres with a 2,244 sqft home and a 1,000 sqft 1900's cottage with a story waiting for its next chapter. There is an in-ground pool in between the house and the cottage, with a privacy fence around it. Condition unknown. Property and structures are being sold AS IS.

354 E 1300 N, Chesterton
1137 N 475 E, Chesterton
$1,350,000
4 Beds ⋅ 5 Baths
15.67 Private Acres | 4 Bed, 5 Bath All-Brick Estate | Pool, Pond & Sunroom | Duneland Schools *THE INTERIOR IS BEING PAINTED A BEAUTIFUL CREAMY WHITE* NEW PICS COMING! Tucked away on 15.67 sprawling acres in Jackson Township, this all-brick estate feels less like a home and more like a private escape -- where luxury, space, and nature meet in perfect balance. With 4 bedrooms and 5 bathrooms across a layout built for both quiet evenings and unforgettable gatherings, every room here earns its place. The kitchen is the heart of the show: granite counters, stainless appliances, and a 6-burner cooktop with griddle ready for anything from Sunday brunch to a full holiday spread. Just off the kitchen, a huge, light-filled family room offers the flexibility to suit however you live -- set it up as a game room for movie nights and gatherings, or dress it up as a formal dining space for holiday entertaining; the choice is yours. The primary suite is a true retreat, with a spacious en suite bath designed for unwinding, while two more bedrooms come with their own private en-suite baths -- comfort and privacy for family or guests alike. A sunroom with a built-in hot tub turns any season into relaxation season, and a dedicated bathroom just steps from the pool keeps pool days effortless. Outside, the estate transforms into a personal resort: dive into the in-ground pool, host under the stars on the expansive deck, or wander private walking trails through mature woods. The stocked pond rounds things out -- perfect for a lazy afternoon of fishing or simply soaking in the scenery. Downstairs, an unfinished basement is a blank canvas waiting for a home theater, gym, extra living space, or guest suite. Zoned for Duneland School Corporation and just minutes from the beaches of Indiana Dunes National Lakeshore, with the South Shore Railway offering an easy ride into Chicago, this is countryside living without giving up the convenience of the city. Schedule your private tour today!

1137 N 475 E, Chesterton
2461 Aeropostale Drive, Chesterton
$580,000
5 Beds ⋅ 3 Baths
Style, space, and thoughtful design come together in this exceptional ranch set within desirable Abercrombie Woods. Positioned on nearly half an acre, this five bedroom, three bath residence offers an impressive scale of living with a fresh, modern aesthetic and a layout designed for both everyday living and entertaining. The main level makes a lasting impression with its open-concept design, generous proportions, and seamless flow between the living, dining, and kitchen spaces. The elevated primary suite provides a private retreat, complete with a luxurious en-suite bath, while two additional bedrooms offer comfortable accommodations for family or guests. The fully finished basement adds an entirely new dimension to the home, featuring expansive recreation space, a dedicated media area, wet bar, home office, two additional bedrooms, and a full bath. Designed for entertaining, relaxing, and hosting, this level offers exceptional versatility. Outside, the backyard creates a private escape of its own. A resort style in-ground pool, three level deck and pergola anchor the outdoor space, with plenty of room to lounge, dine, entertain, and enjoy the seasons. Set in one of the area's most desirable neighborhoods, within the award winning Duneland School District and ideally located for everyday convenience, this home offers a rare combination of modern interiors, generous living space, exceptional outdoor amenities, and the lifestyle that makes Abercrombie Woods so sought after.

2461 Aeropostale Drive, Chesterton
229 E Morgan Avenue, Chesterton
$875,000
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
Start Your Search

Updated . Information deemed reliable but not guaranteed.

How much is your home worth?

Get instant property value now!