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

3 Beds ⋅ 4 Baths

Welcome to 1909 Catkin Circle, an impressive fully updated Modern Farmhouse located in the highly desirable Tamarack Subdivision of Chesterton. Situated on nearly half an acre with beautiful pond views, this 4,284 sq. ft. home offers exceptional indoor and outdoor living with mature landscaping surrounding the property and an expansive wraparound porch. Inside, you'll find 3 bedrooms and 3.5 bathrooms with a thoughtfully designed layout featuring an enlarged, vaulted primary suite, a spacious butler's pantry, and inviting living and entertaining spaces throughout. Three fireplaces add warmth and character, while a whole-house entertainment speaker system makes the home ideal for both everyday living and hosting. The Modern Farmhouse design carries throughout the home, combining updated finishes with comfortable, functional spaces. Step outside to enjoy the wraparound porch, professionally landscaped grounds, and peaceful pond setting that make this property stand out within Tamarack. With 4,284 square feet of living space, a premium pond-side lot, extensive updates, and a combination of luxury, privacy, and character, 1909 Catkin Circle offers a rare opportunity in one of Chesterton's desirable residential communities.

1909 Catkin Circle, Chesterton

4 Beds ⋅ 3 Baths

This meticulously updated four-bedroom, three-bathroom residence is situated in a prime Chesterton location. The interior features a thoughtfully redesigned kitchen equipped with custom hickory cabinetry, granite countertops, and premium stainless-steel appliances. Abundant natural light fills the living room through a newly installed expansive window, flowing seamlessly into a spacious dining area and a comfortable sunroom - perfect for morning coffee and evening relaxing. The home offers four generously proportioned bedrooms, including two en-suite bathrooms located on the upper and lower levels respectively, all complemented by new modern vanities and fixtures. Fresh interior paint, new lighting, and a combination of new carpeting and new luxury vinyl plank flooring complete the refined interior. Additional versatility is provided by lower-level bonus spaces suitable for a recreation room, home gym, or multi-generational living arrangements. The attached garage features all-new shelving and a new insulated overhead door with new quiet, side-mount opener. Exterior improvements include a new roof installed in 2025, upgraded gutters, fascia, soffit, exterior doors, and a newly constructed composite front porch. Conveniently positioned on a dead-end, cul-de-sac street, the property offers exceptional proximity to schools, parks, shopping, commuter transit, major interstates, and the Indiana Dunes National Park. Schedule your showing today!

762 Dunewood Drive, Chesterton

3 Beds ⋅ 3 Baths

Rarely available home in the sought after Tamarack subdivision. Elegant custom-built brick ranch with impressive curb appeal, lush landscaping, and a grand columned entry. Soaring ceilings, arched openings, abundant natural light, and hardwood floors create an inviting interior, while the spacious living room features a fireplace and flows easily into the formal dining room and breakfast area. The kitchen offers rich wood cabinetry, generous counter space, stainless steel appliances, a center island, and a built-in oven and microwave installed in 2022. The primary suite includes vaulted ceilings, plantation shutters, dual vanities, a walk-in tub, separate shower, and walk-in closets. Highlights include main-level laundry, furnace and central air replaced in 2020, a 2026 garage door opener, exterior railings, a huge unfinished basement with an egress window and flexible studio, recreation, hobby, and storage space. Enjoy the resurfaced covered patio, colorful gardens, and private tree-lined backyard.

1910 Catkin Circle, Chesterton

3 Beds ⋅ 4 Baths

Welcome to 1429 Calais Court, a beautifully maintained paired home nestled in the CHATEAUX DU CHAMBORDE area in the sought-after Sand Creek community of Chesterton. Offering the perfect blend of comfort, convenience, and low-maintenance living, this home is ideal for anyone looking to enjoy a relaxed lifestyle in one of Northwest Indiana's premier neighborhoods. Step inside to find a bright, inviting floor plan with spacious living areas, abundant natural light, and a layout designed for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living spaces, creating a warm and welcoming atmosphere. The generous primary suite provides a private retreat, while additional living space offers flexibility for guests, a home office, or hobbies. Enjoy your morning coffee or unwind in the evening on your private patio while taking in the peaceful surroundings. Located within the prestigious Sand Creek community, you'll appreciate easy access to golf, walking paths, shopping, dining, top-rated Duneland schools, and the beautiful Indiana Dunes National Park and Lake Michigan shoreline. With convenient access to major highways and the South Shore Line, commuting to Chicago is also within easy reach.

1429 Calais Court, Chesterton

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

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 in this exceptional 3 bedroom, 2 bath ranch, perfectly nestled on a .92 acre wooded lot! This custom built home offers an open-concept design with soaring vaulted ceilings in the kitchen, dining, and living areas. Every detail was thoughtfully designed for comfort, including polished concrete floors with radiant in-floor heat throughout the home. The beautifully appointed kitchen features granite countertops, soft-close cabinery and energy efficient appliances. The primary suite includes direct patio access, a walk-in closet and a spa inspired bath. Two additional bedrooms offer flexibility for guests or a home office. A convenient utility room includes a stackable washer and dryer and an Energy Star rated combi boiler, offering efficiency and year round comfort. The oversized 2 car garage is eqipped with insulated walls and doors, keyless entry and pull-down attic access for abundant storage. Relax on the 15 x 12 covered patio and enjoy the peaceful wooded views. Prime Chesterton location, near the seasonal European and Farmer's Markets, the new YMCA Healthy Living Campus, shopping, dining, wineries, and Indiana Dunes. Experience the perfect balance of luxury, comfort and nature all in one exceptional home!

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 ⋅ 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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