Chesterton Homes with Westchester Intermediate Middle School

Welcome to Chesterton, Indiana – a charming gem nestled in Porter County, where small-town warmth meets modern convenience. Just a stone's throw from the stunning shores of Lake Michigan, Chesterton boasts a vibrant community spirit, a rich history, and an abundance of natural beauty. With its picturesque parks, quaint downtown area, and proximity to the bustling cities of Chicago and Gary, Chesterton offers the perfect blend of tranquility and accessibility.

For families, Chesterton is particularly appealing due to its strong educational opportunities, notably the renowned Westchester Intermediate Middle School. This institution is celebrated for its commitment to academic excellence and fostering a nurturing environment for students. Homes located within the Westchester Intermediate Middle School district are highly sought after, making this area a prime choice for families looking to provide their children with quality education.

The real estate landscape in Chesterton features a diverse array of homes, from charming historic houses to modern new builds, ensuring there’s something to suit every taste and budget. The neighborhoods around Westchester Intermediate are particularly desirable, offering spacious yards, friendly neighbors, and a sense of community that makes you feel right at home.

With a rich array of local shops, restaurants, and recreational activities, Chesterton is not just a place to live; it’s a place to thrive. Whether you’re strolling through the scenic parks, enjoying a local festival, or simply relaxing in your backyard, Chesterton invites you to experience the best of Indiana living. Come discover your new home in this delightful town!

Newest Chesterton Homes with Westchester Intermediate Middle School

$529,900

4 Beds ⋅ 3 Baths ⋅ 844236 MLS ⋅ 2,596 SqFt. ⋅ John Guest

Stunning, updated 2-story home nestled on a private, wooded 0.56-acre in-town lot in Chesterton! A grand 2-story entry welcomes you with luxury vinyl plank flooring extending throughout the main level, featuring a formal dining room. French doors from a den/office and flow into the family room, highlighted by a gas-start fireplace and a wall of windows showcasing the woods. The open-concept layout effortlessly connects the family room, eating area, and peninsula counter kitchen, which boasts painted oak cabinets, solid surface countertops, and recessed lighting. The rear hallway leads to the laundry room, a 3-car garage, and a vaulted ceiling screen porch with skylights. Step outside to a private, professionally designed outdoor oasis featuring a paver patio, a granite gas grill island with bar seating, a 55" outdoor TV in a storm box, a wood-burning fireplace, and a 4-person hot tub. Upstairs, the primary suite offers vaulted ceilings, a walk-in closet, a double vanity, a soaking tub, and separate shower, alongside three additional bedrooms and a full bath. The garage features a walk-up attic stairwell for easy storage or potential expansion with access through the 4th bedroom too. Complete with zoned 2010 Lennox HVAC and city utilities, this property offers quick access to Highways 49, I-90, and I-94 and near the Indiana Dunes National Park.

131 Beverly Drive, Chesterton

Listing courtesy of John Guest from Coldwell Banker Realty.

$269,900

2 Beds ⋅ 1 Baths ⋅ 842889 MLS ⋅ 1,204 SqFt. ⋅ Diane Cline

515 S Park Drive, Chesterton

Listing courtesy of Diane Cline from McColly Real Estate.

$425,000

3 Beds ⋅ 3 Baths ⋅ 839267 MLS ⋅ 3,444 SqFt. ⋅ Patricia Raffin

This property offers the ideal combination of location, lot, and lifestyle. Located in Duneland Cove, this nearly 3,000-square-foot home features 3 bedrooms, 3 bathrooms, and a 3-car garage, all just minutes from shopping, healthcare, major highways, rail access, and the shoreline beaches of Lake Michigan. The main level's circular floor plan connects the living room, dining room, kitchen, and family room, with beautiful backyard views from inside the home and from the deck. A centrally located half bath sits next to the den. Upstairs, you'll find three spacious bedrooms and a full hall bathroom shared by Bedrooms 2 and 3. The primary suite includes a three-quarter bath and an adjacent loft that can serve as an office or flexible living space. The daylight basement adds more finished living area, including recreation space and a double-door walkout to a brick patio and garden path. This two-story home also features a welcoming covered front porch, a split HVAC system for garage comfort, a functional layout, and a convenient location. Home is being sold "As Is".

947 Sandpiper Drive, Chesterton

Listing courtesy of Patricia Raffin from McColly Real Estate.

$335,000

3 Beds ⋅ 2 Baths ⋅ 838462 MLS ⋅ 1,419 SqFt. ⋅ Jamie Bond

Deal Fell Thru No Fault to Seller!!! Perfectly Located Just Minutes from the Indiana Dunes National Park and Lakeshore. This Classic Ranch is Nestled Among Mature Trees in a Quant Neighborhood, Offering a Rare Blend of Quality Craftsmanship and Commuter Convenience. The Open -Concept Design Features Vaulted Ceilings, Stunning Cedar Accents, and an Original 1963 Floor to Ceiling Brick Fireplace Extending to the Unfinished Basement, Serving as a Striking Mid- Century Focal Point. The Custom Kitchen Showcases Quartz Countertops and Handcrafted Cabinetry Made from a Single Tree, Offering Exceptional Character and Craftmanship. The Spacious Layout Includes 3 Bedrooms and 2 Baths, including a Private Primary Suite with Attached Bath and Your Very Own Sliding Door Leading to a secluded Patio. The Unfinished Basement Provides Endless Possibilities for Additional Living Space, Storage, or Recreation. Located in the Award -Winning Duneland School District with Convenient Access to the South Shore Train Station, Toll Road and Expressways- Perfect for Chicago Commuters.

1248 Dogwood Drive, Chesterton

Listing courtesy of Jamie Bond from Listing Leaders.

$1,199,900

5 Beds ⋅ 6 Baths ⋅ 834301 MLS ⋅ 7,084 SqFt. ⋅ Stefanie Neal

Perfectly positioned along the fairway in the gated Sand Creek community, this impressive custom residence blends grand scale living with thoughtful design and exceptional versatility. From the moment you enter, a dramatic two-story foyer sets the tone, opening to inviting living spaces and a sweeping catwalk overlooking the heart of the home. The two-story great room is anchored by a striking stone fireplace and windows framing picturesque golf course views. Designed for gathering, the kitchen offers premium appliances, a center island, walk-in pantry, and butler's pantry, all seamlessly connected to casual dining and living areas. Dual staircases provide both functionality and architectural interest throughout the home. The main-level primary suite offers a private retreat complete with a spa-inspired bath, steam shower, soaking tub, dual vanities, and walk-in closets. A home office or study with French doors is also located on the main. Upstairs, 3 spacious bedrooms each feature access to full baths, while a large bonus room offers endless possibilities as an additional bedroom, playroom, media lounge, creative studio, home office, fitness area, or hobby space -- truly adaptable to fit your lifestyle. Outdoor living shines with a 900-sq ft deck overlooking the large backyard and sweeping fairway views, creating the perfect setting for entertaining or quiet evenings at home. The finished daylight basement is designed with entertainment in mind, featuring a large recreation area, custom bar, theatre room, and hidden rooms cleverly tucked behind built-in shelving for a unique and memorable experience. The basement easily functions as a guest retreat or extended living quarters. Additional highlights include a heated 3-car garage, abundant storage throughout, and incredible flexibility to create anything you desire for your new home. Experience elevated living-where grand entertaining, everyday comfort, and breathtaking views create a truly unforgettable home.

1240 Ryder Road, Chesterton

Listing courtesy of Stefanie Neal from BHHS Indiana Realty.

Start Your Search

Updated . Information deemed reliable but not guaranteed.

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.