Explore Chesterton, IN Homes for Sale Between $450,000 to $500,000

Homes for Sale in Chesterton, IN Between $450,000 to $500,000

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Welcome to your dedicated resource for Homes for Sale Between $450,000 to $500,000 in Chesterton, IN. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesterton, IN agent, Listing Leaders specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $450,000 to $500,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Chesterton, IN Homes for Sale Between $450,000 to $500,000

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

6 Beds ⋅ 6 Baths

Excellent investment opportunity in the heart of Porter! Built in 2019, this well-maintained duplex features two spacious townhome-style units, each offering 3 bedrooms, 2.5 bathrooms, an attached garage, and approximately 1,530 square feet of living space. Both units are currently leased through August 31, 2026, providing immediate cash flow with additional rental upside. Tenants pay all utilities, including heat, A/C, water, sewer, and trash, while owner expenses are limited to lawn care and snow removal. Conveniently located near major highways, shopping, dining, Indiana Dunes National Park, and South Shore commuter rail, this low-maintenance property is an excellent addition to any investment portfolio.

1250-1252 Lawson Lane, Chesterton

3 Beds ⋅ 2 Baths

Better than new and loaded with thoughtful upgrades, this beautiful ranch home offers the perfect blend of comfort, convenience, and low-maintenance living. Ideally located near walking trails, restaurants, and everyday amenities, you'll love the lifestyle this location provides. Step inside to discover over 1800 square feet of this open concept floor plan featuring three spacious bedrooms and bright, light-filled spaces designed for both entertaining and everyday living. The well-appointed kitchen is a standout with double ovens, a gas cooktop, abundant workspace, and seamless flow into the main living and dining areas. Expand your living space into the basement that is ready to be finished to your liking and currently offers a finished storage closet. Outside, enjoy relaxing or entertaining on the composite deck beneath the pergola overlooking the partially fenced backyard. Additional upgrades provide peace of mind and exceptional value, including an irrigation system, whole-house generator, battery backup for the sump pump, radon system and more! This move-in ready home combines modern style and upgrades that truly set it apart from the competition. Don't miss your opportunity to make it yours!

1669 Gossett Mill Avenue, Chesterton

9 Beds ⋅ 4 Baths

501 Wabash Ave is an extraordinary property located in the heart of Chesterton, Indiana. This versatile space offers numerous possibilities: Generational living? Absolutely. Income-producing potential? Yes. A stunning open-concept home with an apartment and guest suite for visiting family and friends? Definitely. Spanning 4,400 square feet, this property is as adaptable as it is distinctive. The main living area features beautiful hardwood floors, an expansive open layout perfect for entertaining and relaxation, four well-sized bedrooms, and a luxurious custom-built shower in the main bathroom. The kitchen, renovated in Spring 2026, is a chef's paradise, featuring new countertops, stainless steel appliances, a pot filler and plenty of cabinetry to accommodate all your cooking essentials. Additionally, there are two more bedrooms, a full bathroom, and another kitchen, dining and living room adjacent to the main area with brand new flooring. This area can function as space for multi-generational living or be easily separated to create two distinct spaces. But that's not all! Above the three-car garage, you will discover a three-bedroom, one-bathroom apartment with modern flooring, recessed lighting, its own entrance, and a private deck perfect for enjoying the outdoors. This hidden gem is situated within the award-winning Duneland School District, just a leisurely stroll from the Chesterton European Market, minutes from the beach and State & National Parks, and conveniently close to fantastic local amenities. Plus, it's just a short drive to Chicago. Don't wait or hesitate--schedule your showing today and make this versatile and delightful home yours!

501 Wabash Avenue, Chesterton

3 Beds ⋅ 3 Baths

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

3 Beds ⋅ 2 Baths

CUSTOM RANCH HOME IN DESIRABLE ABERCROMBIE WOODS-MODERN COMFORT IN AN EXCEPTIONAL LOCATION. Welcome home to this beautifully maintained custom-built ranch in the highly sought-after Abercrombie Woods neighborhood. Offering 2,172 square feet of thoughtfully designed main-level space, this Spacious home features an inviting open floor plan with three generously sized bedrooms, two full bathrooms, and a full unfinished basement with a rough in for future bath- providing endless possibilities for additional living space, hobbies, a workshop, home gym, or abundant storage. Designed for both comfortable family living and effortless entertaining, the bright and open layout includes spacious living and dining areas that flow seamlessly into the well-appointed kitchen. You'll appreciate the rich cherry cabinetry , quartz countertops and backsplash, spacious pantry and the welcoming breakfast nook perfect for casual meals and morning coffee. The Private Primary Suite serves as a relaxing retreat, complete with a Luxurious En-Suite bath featuring a jetted soaking tub, separate shower, double vanity, heated tile floor for the chilly mornings, and a large wake-in closet. Two additional spacious bedrooms and a second full bath provide plenty of room for family or guests. Quality Craftsmanship is evident throughout with Vaulted Ceilings Custom Moldings, Rounded Corners, Ceiling Fans, and Numerous Thoughtful details that add both style and character. Major Maintenance updates provide peace of mind, including a New Central Air Conditioner Installed in 2025, along with a Furnace, Water Heater, Sump Pump, Refrigerator and Dishwasher all recently replaced allowing you to move in with confidence. Beyond the home itself, the Neighborhood has 5 Scenic Ponds, Sidewalks, and is 6 Miles from Indian Dunes State Park. Located in the Award-Winning Duneland Community School School Corporation. This is a MUST SEE.

4171 Westwood Lane S, Chesterton

3 Beds ⋅ 4 Baths

Now available in Sand Creek--currently the only townhouse on the market! Located in one of Northwest Indiana's premier golf course communities, Sand Creek offers beautifully maintained surroundings, mature trees, and an upscale lifestyle just minutes from downtown Chesterton and the Indiana Dunes. This beautifully updated three-bedroom home features a fully remodeled open concept main level and easy, maintenance-free living. Say goodbye to lawn care and snow removal and enjoy more time relaxing in a home that blends comfort, style, and convenience. Step inside to cathedral ceilings and large windows that fill the home with natural light and create an open, spacious feel. The kitchen features granite countertops, a large center island, and hardwood floors throughout the main level, flowing seamlessly into the spacious living and dining areas--ideal for everyday living and entertaining. Upstairs, you'll find three generously sized bedrooms, including a spacious primary suite with a large walk-in closet. The finished lower level offers flexible space ideal for a home gym, recreation room, office, or additional living area. Step outside to a private backyard with a peaceful Zen garden feel, featuring a waterfall and relaxing outdoor setting. Additional highlights include a two-car garage with a storage lift that stays with the home and a convenient location close to major highways for an easy commute. This move-in-ready home combines comfort, style, and low-maintenance living all in one!

1077 Mission Hills Court, Chesterton

3 Beds ⋅ 2 Baths

Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat located within minutes of award-winning schools, commuter expressways, and the IN Dunes National Lakeshore. The Driftwood floor plan offers almost 1,700 sq. ft. on the main floor, plus a full basement! Upon entrance you'll find the expansive kitchen where you'll enjoy an abundance of soft-close cabinetry, center island, pantry, and dinette seating. With cathedral ceilings soaring overhead, the living room is centered around the cozy fireplace. The master suite boasts a tray ceiling, large walk in closet, and private bath with dual vanities. The unfinished basement offers plenty of room to grow or additional storage spaces! Prepare to enjoy the simple life with your lawn care maintenance and snow removal all taken care of! Quality features such as tankless water heater, fully finished garage with insulated garage door and Wifi-enabled opener, soundproofing insulation, comfort-height Toto toilets, full kitchen appliance package, customized lighting allowance, and full landscaping package including in-ground sprinklers ensure this home is ready for your instant enjoyment. Schedule your showing today to discover all that this exciting community has to offer! *Photos are of another home recently completed and are representative.

2316 Redwood Lane, Chesterton

Attention train lovers! This is the opportunity of a lifetime...you can own and operate your own business out of four train cars. There is a building in the middle that connects all four cars. In between the cars is an eighty foot deck on each side. The building is just across the tracks from a train bed and breakfast, the Duneland Chamber of Commerce(where the European Market is held and has as many as 3,000 visitors per weekend), and quaint downtown Chesterton. There's even a public bathroom in a train car in the park. Across Fourth Street is the 4th Street Theater. Lake Michigan, Porter Beach, the South Shore Train Station, the Indiana Toll Road, I-94, and the Indiana Dunes National Park(over four million visitors in 2022) are within minutes of this stellar location. This property lies within the Chesterton Riverfront Development Project, which you can apply for a liquor license.

301 Grant Avenue, Chesterton

6 Beds ⋅ 6 Baths

This newly completed duplex was finished in 2024. This exceptional investment property features two spacious units--each offering 3 bedrooms, 3 bathrooms, and a convenient one-car garage. Both sides are currently leased, providing immediate rental income. The main level showcases durable LVP flooring, while the primary suite includes a generous walk-in closet. Quality finishes such as 6-panel oak interior doors add warmth and character throughout. Ideally located near downtown Chesterton and Porter, the South Shore Train Station, and the breathtaking Indiana Dunes State Park, this property combines modern comfort with unbeatable access to Northwest Indiana's top amenities.

150-152 N 16th Street, Chesterton

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