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, Kimberly Sut Group 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

$455,000

3 Beds ⋅ 3 Baths ⋅ 844895 MLS ⋅ 2,932 SqFt. ⋅ Shelly Grimm

Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly 3,000 sq. ft. of finished living space has been thoughtfully updated from top to bottom, offering the charm of an established home with the finishes, comfort, and peace of mind of something new. Major upgrades include a **NEW ROOF, NEW FURNACE, NEW CENTRAL A/C, and a WHOLE-HOME GENERATOR**--making this home truly move-in ready. Inside, you'll find 3 spacious bedrooms, 2.5 beautifully updated baths, TWO separate living areas, an eat-in kitchen with stone countertops and stainless steel appliances, high ceilings, recessed lighting, a main-level primary bedroom, and convenient main-level laundry. The upper level offers two generously sized bedrooms plus a large loft, providing plenty of flexibility for an office, playroom, additional lounge, or guest space. Outside, enjoy a private, landscaped **0.54-acre lot**, rear deck, storage shed, and attached 2-car garage with NO HOA. With virtually everything already upgraded, all that's left to do is move in and enjoy this stunning Chesterton home!

2332 Dakota Street, Chesterton

Listing courtesy of Shelly Grimm from White Hat Realty Group, LLC.

$455,000

3 Beds ⋅ 2 Baths ⋅ 844885 MLS ⋅ 1,734 SqFt. ⋅ Dawn Bernhardt

This sweet villa home has everything you need--without the worry of exterior maintenance! Conveniently located on the near east side of Chesterton, you'll enjoy easy access to shopping, expressways, the train station, and one of the area's greatest attractions, Indiana Dunes National Park. More than cute and gently lived in, this charming three-bedroom, two-bath, 1,700-square-foot ranch is sure to impress. The open floor plan is perfect for entertaining, with a cozy fireplace to warm you in the winter and a large patio with a retractable sunshade to enjoy during the summer. Luxury vinyl flooring runs throughout the home, with tile flooring in the bathrooms. The primary bedroom is privately situated on one side of the home, while the other two bedrooms are located on the opposite side. The primary bath features a tiled shower with a frameless glass door, double sinks, a walk-in closet with organizers, and a linen closet. The kitchen features a large island that provides additional seating, along with a beverage refrigerator, newer stainless steel appliances, and a pantry. The laundry/mudroom offers a convenient place to sit and remove your shoes, along with space for coats and keys, a storage closet, plenty of cabinetry, a washer and dryer, and a laundry sink. The slightly oversized two-car garage provides plenty of additional storage along both sides. The home's mechanicals are conveniently housed in a large garage closet, and pull-down attic stairs provide access to even more floored storage above the garage. The maintenance package makes life easy and includes lawn mowing, snow removal up to your door and driveway, trimming, fertilizing, and spring and fall sprinkler-system maintenance. Comfortable, convenient, and easy to maintain--come see this one soon! .

472 Cypress Lane, Chesterton

Listing courtesy of Dawn Bernhardt from Blackrock Real Estate Services.

$459,000

4 Beds ⋅ 3 Baths ⋅ 844730 MLS ⋅ 2,276 SqFt. ⋅ Jarrod Carr

Built in 2025 and practically brand new, this beautiful 4-bedroom, 2.5-bath home offers modern finishes, a functional layout, and plenty of room to grow! The open-concept main level is designed for both everyday living and entertaining, featuring a spacious kitchen with quartz countertops, abundant counter and cabinet space, and a large center island. The kitchen flows seamlessly into the inviting living room and out to the deck, creating a great space for gatherings or relaxing outdoors. A private office and convenient half bath complete the main level. Upstairs, you'll find all four bedrooms, including a spacious primary suite with a private ensuite bath and an impressively large walk-in closet. The unfinished daylight basement provides excellent potential for additional living space, a recreation room, home gym, or whatever fits your needs. Outside, enjoy the convenience of an irrigation system and a newer home without the wait of new construction. Ideally located near downtown Chesterton with easy access to local restaurants, shops, parks, and highly regarded schools. Move right in and enjoy everything this nearly new home has to offer!

29 Karner Blue Court, Chesterton

Listing courtesy of Jarrod Carr from @properties/Christie's Intl RE.

$475,000

842974 MLS ⋅ 1,744 SqFt. ⋅ Nicholas Sommer

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

Listing courtesy of Nicholas Sommer from Century 21 Alliance Group.

$495,000

6 Beds ⋅ 6 Baths ⋅ 842346 MLS ⋅ Tariq Suboh

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

Listing courtesy of Tariq Suboh from Ellsbury Group.

$465,000

3 Beds ⋅ 4 Baths ⋅ 838852 MLS ⋅ 3,199 SqFt. ⋅ Jason Moon

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

Listing courtesy of Jason Moon from Trueblood Real Estate, LLC.

$459,900

3 Beds ⋅ 2 Baths ⋅ 838833 MLS ⋅ 1,676 SqFt. ⋅ Michelle Renninger

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

Listing courtesy of Michelle Renninger from Brokerworks Group.

$450,000

837371 MLS ⋅ 6,236 SqFt. ⋅ Paul Boyter

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

Listing courtesy of Paul Boyter from McColly Real Estate.

$499,900

6 Beds ⋅ 6 Baths ⋅ 831008 MLS ⋅ Paul Boyter

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

Listing courtesy of Paul Boyter from McColly Real Estate.

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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.