Chesterton Homes with Garage Faces Side Parking Features

Chesterton Homes with Garage Faces Side Parking Features

Welcome to Chesterton, Indiana – a charming town nestled in Porter County that beautifully balances small-town charm with modern conveniences. Known for its picturesque landscapes and vibrant community, Chesterton offers a welcoming environment that appeals to families, professionals, and retirees alike. With its proximity to Lake Michigan and the stunning Indiana Dunes National Park, outdoor enthusiasts will find endless opportunities for hiking, biking, and enjoying the serene natural beauty that surrounds this delightful town.

Chesterton is also home to a thriving downtown area, featuring an array of unique shops, local eateries, and cultural attractions. The annual Chesterton European Market is a highlight, showcasing local artisans and farmers, making it a perfect spot to connect with neighbors and support local businesses.

When it comes to housing, Chesterton offers a variety of options to suit diverse lifestyles. Among the popular features of homes in this area are properties with side-facing garages. These homes not only provide convenient parking solutions but also enhance the curb appeal of the property, allowing for beautifully landscaped front yards. Side-entry garages are particularly sought after for their ability to keep the garage door hidden from view, creating a more aesthetically pleasing facade.

Whether you’re looking to settle down in a cozy family home or seeking a peaceful retreat, Chesterton’s real estate market has something for everyone. Explore the charm of this vibrant community and discover your dream home in Chesterton, where comfort and convenience meet the beauty of Indiana living.

Newest Chesterton Homes with Garage Faces Side Parking Features

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

4 Beds ⋅ 4 Baths

Unmatched curb appeal, custom craftsmanship, with 3.44 acres of privacy with 4 Bedroom and 4 Baths. This stunning Craftsman-style home offers an idyllic retreat within the coveted Duneland School District. From the moment you pull up to the expansive three-car garage. Featuring a generous 13 ft by 30 third bay perfect for a boat, workshop, or extra storage and see the gorgeous wrap-around front porch, you'll know you've found something special. Inside, the quality is undeniable 2x6 construction, solid wood doors, and wood trim throughout the main floor. Beautiful wood floors flow seamlessly through the entryway, dining room, kitchen, and hallway. Host gatherings in the elegant dining room, by solid wood columns and plantation shutters, or cook with ease in the spacious eat-in kitchen, complete with beautiful maple cabinets and an ample amount of counter and storage space. Step directly from the kitchen out to a charming screened-in porch, which opens to a durable Trex deck,ideal for outdoor dining and taking in views of your private acreage. Afterwards, relax in the impressive living room anchored by soaring vaulted ceilings and a warm gas fireplace. Main-floor primary sanctuary features direct access to the wrap-around porch and a spa-like ensuite bath complete with a double vanity, soaking tub, walk-in shower, private toilet closet, and a spacious walk-in closet. Down the hall, a secondary main-floor in-law suite with an adjacent 3/4 bath provides unmatched flexibility. As you head upstairs, you will notice the gorgeous wooden staircase. You'll find two generously sized bedrooms and a full bath with double sinks and along with an unfinished area above the garage offering incredible potential for future expansion. Downstairs in the partially finished basement adds even more versatile space, complete with daylight windows, a full bath, and direct interior stairs leading right up to the garage. For complete peace of mind, the home comes with Generac Generator

386 E 1050 N, 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

3 Beds ⋅ 2 Baths

LUXURY MEETS NATURE! On nearly an acre of land within charming Chesterton, this modern ranch home strikes the a rare balance of privacy, comfort and convenience. Relax on the covered patio surrounded by the sights and sounds of nature, or gather your guests around a fire pit in the secluded backyard. With no HOA and plenty of land, there is the opportunity to craft your vision on this exceptional site. Polished concrete floors with radiant in-floor heating provide year-round comfort, ease of maintenance, and reflect a design philosophy that celebrates natural materials and enduring craftsmanship. Soaring ceilings, expansive windows, and timeless finishes create a bright, inviting great room that feels both grand and comfortable. Just a few moments exploring the chef's kitchen will reveal curated details that elevate both cooking and entertaining. Designed as a relaxing retreat, the primary suite offers patio access, a walk-in closet, and a spa-inspired ensuite. Two additional bedrooms provide flexibility for both guests and a home office. Energy efficient and low maintenance features throughout make this home as functional as it is beautiful. Ideally located in Chesterton with easy access to the Prairie Duneland Trailhead, Dogwood Park, Migratory Bird Sanctuary, European Market, new YMCA campus, Duneland Schools and the Indiana Dunes.

2645 W 1100 N, Chesterton

3 Beds ⋅ 4 Baths

This exceptional all-brick ranch offers over 4,200 finished square feet of thoughtfully designed living space. A traditional floor plan welcomes you with a gracious foyer, rich Cherry hardwood floors, and crown molding that flow throughout the main living areas. The library/office--originally designed as a third main-floor bedroom--offers flexibility for work or additional guest accommodations. Formal living with elegant fireplace and dining room with convenient service bar, create an inviting setting for entertaining. The kitchen is appointed with stainless steel appliances and an island workspace and opens seamlessly to the breakfast room with access to the screened porch and adjoining keeping room featuring a slanted ceiling and bay windows that fill the space with natural light. Privately situated on the opposite side of the home, the bedroom wing includes a spacious primary suite with tiled shower, dual vanities, and walk-in closet, along with a guest bedroom featuring its own full ensuite bath. The walk-out lower level expands the home's versatility with a large great room anchored by a double-sided fireplace, wet bar with granite countertops, family room, game room, private bedroom suite, and a dedicated workroom ideal for planting, painting, crafts, or woodworking. Completing the property are a two-car garage and separate golf cart garage, perfectly suited for an active lifestyle. Enjoy the ease of a low-maintenance lifestyle while retaining the spacious feel and individuality of a traditional residence. The association provides lawn care and fertilization, irrigation, snow removal, and maintenance of common areas--allowing more time to enjoy life and less time worrying about exterior upkeep.

1340 Cantigny Court, Chesterton

4 Beds ⋅ 3 Baths

The Acadia in Easton Park! Welcome to luxury living in this stunning two-story home offering just under 2,300 square feet of thoughtfully designed living space. Featuring 4 spacious bedrooms, 3 bathrooms and a spacious 2-car garage, this home perfectly blends comfort, quality and style. Step inside to an open-concept floor plan showcasing hardwood floors, custom cabinetry, a beautiful trim package throughout, solid core doors and soft-close cabinets. The gourmet kitchen is complete with stainless steel appliances, quartz countertops, a large island and an abundance of workspace, making it perfect for entertaining or everyday living. Gather around the custom fireplace, thoughtfully placed to create a warm and inviting living space. The luxurious primary suite offers a peaceful retreat with a double vanity, alcove tub, custom tiled shower with seamless glass enclosures and a large walk-in closet. 3 additional bedrooms, 1 w/walk-in closet and a beautiful full bath complete the upper level. Additional highlights include energy-smart features, zoned efficient HVAC, humidifier, fresh air intake, R-20 insulation in exterior walls, tankless hot water heater, generous electrical lighting package, irrigation system and a beautiful composite deck perfect for outdoor enjoyment. The unfinished basement includes roughed-in plumbing and an egress window, providing endless possibilities for a future bedroom, bathroom, recreation space, or additional living area. Situated on a desirable corner lot in the highly sought-after Easton Park subdivision, this exceptional home is just minutes from the Indiana Dunes National Park, the South Shore Line, major expressways and award-winning schools! Call for your showing today!

2230 Redwood Lane, Chesterton

4 Beds ⋅ 5 Baths

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

5 Beds ⋅ 6 Baths

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

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