4 Bedroom Homes for Sale in Chesterton, IN

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Welcome to your dedicated resource for 4 bedroom homes for sale 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 4 bedroom properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All 4 Bedroom Homes for Sale in Chesterton, IN

$359,900

4 Beds ⋅ 2 Baths ⋅ 843482 MLS ⋅ 1,828 SqFt. ⋅ Melissa Capellari

Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

2342 Westwood Lane, Chesterton

Listing courtesy of Melissa Capellari from Coldwell Banker Real Estate Gr.

$395,000

4 Beds ⋅ 4 Baths ⋅ 843317 MLS ⋅ Paul Boyter

Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining rental unit, now vacant, includes 2 bedrooms and 2 bathrooms, allowing you to choose the tenants and rents. The 455 side has a brand new air conditioner and new appliances last year. New windows were installed in 2025. Both units enjoy large, private backyards perfect for relaxing, entertaining, or gardening. Conveniently located just minutes from the beautiful beaches of Lake Michigan, charming downtown Chesterton, and the renowned European Market, this property also offers an easy commute with quick access to the South Shore Line and I-94, putting downtown Chicago within approximately 45 minutes. Whether you're looking to reduce your housing costs or expand your investment portfolio, this property offers the perfect combination of comfort, convenience, and income potential.

455 Woodlawn Avenue, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

$679,000

4 Beds ⋅ 3 Baths ⋅ 843120 MLS ⋅ 2,409 SqFt. ⋅ Madison Young

Only 3 years young- this new construction build was completed by one of NWI's most prestigious builders in the desirable Preserve neighborhood known for its thick tree lines of protected land! A backyard oasis is already complete for you and makes this home the best value you could be looking for in Chesterton! It's not everyday you see a backyard like this - inground pool with automatic safety cover, putting green and large stamped concrete patio for backyard dinners. Beautiful mature landscaping and surrounded by trees on 2 sides. The home sits on a quiet cul de sac and is a show stopper with high end finishes. A 2 story foyer greets you and welcomes you into the 2 story great room with a gas fireplace at the heart. A bright kitchen overlooking your backyard oasis and featuring quartz countertops with a six drawer island, walk in pantry with built in shelving and including a mini fridge. Off kitchen dining for casual family dinners and a formal dining for entertaining. An office, half bath and bedroom finish the main level living with mudroom access from the garage to kitchen. Upstairs you will find a beutifully appointed primary en suite with wainscotting, walk in closet with custom built in organizers, walk in tiled shower with frameless glass doors, and double vanity. 2 other bedrooms complete the upstairs along with UPSTAIRS LAUNDRY for added convenience. And last but not least a full unfinished basement of additional 1300 potential living space with 9 ft ceilings for future expansion and includes egress window for future 5th bedroom and rough in plumbing for future 4th bathroom. This home has everything you are looking for and is 15 mins from train station for easy to commute to Chicago, 10 mins from Chesterton downtown with local restaurants, coffee shops and the famous European farmers market! Award winning Duneland School system with the high school and the popular Dogwood park only 4 minutes! Taxes will be lower with new owners homestead exemption!

18 Blue Grass Way, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$559,900

4 Beds ⋅ 3 Baths ⋅ 842981 MLS ⋅ 1,820 SqFt. ⋅ Madison Young

Introducing the Aspen on Lot 4 in 1100 Woods! PROPOSED CONSTRUCTION***** Located in the heart of Chesterton across from Dogwood Park and the Prairie Duneland Trail. The Aspen model is ideal for those looking for a primary ensuite on main level with walk in closet, a large kitchen island for extra seating to gather, and plenty of storage. Kitchen over looks your great room and dining for an open concept.

2350 Pradera Trail, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$529,900

4 Beds ⋅ 3 Baths ⋅ 842418 MLS ⋅ 2,412 SqFt. ⋅ Shelley Seely

FORE! Welcome to this exquisite Cape Cod residence in the prestigious Estates of Sand Creek subdivision. Enjoy breathtaking views of the 4th hole of the Marsh Course at Sand Creek Country Club from the comfort of your own home, without being directly on the course. This spacious 4-bedroom, 2.5-bath home offers over 2,400 square feet of well-appointed living space. Open concept living with vaulted and cathedral ceilings allow for a plethora of natural light to shine throughout. The kitchen and bathrooms feature elegant quartz countertops, owner added a maintenance free gas fireplace with white fireglass, and a new roof that provides peace of mind. The unfinished full basement with 9-foot ceilings offers incredible potential for expansion, perfect for a family room, home gym, theater, or additional bedrooms. Outdoor living shines with a flagstone patio and permanent ceramic gas firepit, mesmerizing green fireglass, ideal for entertaining or quiet evenings. Residents enjoy resort-style amenities within the Sand Creek community, including access to championship 27-hole golf with 3 (9 hole )courses, a beautiful pool complex, fitness center, tennis courts, and fine dining at the clubhouse, all set among scenic ponds and rolling terrain. Conveniently located just minutes from the Indiana Dunes National Lakeshore, Lake Michigan's pristine beaches, the South Shore Train Station, and major highways. Top-rated Duneland School District completes this exceptional package. This is more than a home -- it's a lifestyle.

961 Monterey Drive, Chesterton

Listing courtesy of Shelley Seely from Realty Executives Premier.

$649,900

4 Beds ⋅ 4 Baths ⋅ 842114 MLS ⋅ 2,878 SqFt. ⋅ Stefanie Neal

Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updated 4-bedroom, 3.5-bath home offers timeless design, modern improvements, and exceptional golf course views. A grand foyer welcomes you into a thoughtfully designed floor plan featuring a private home office, formal dining room, and inviting living room anchored by a cozy fireplace and expansive windows overlooking the course. The remodeled kitchen is the heart of the home, showcasing quartz countertops, custom cabinetry, stainless steel appliances, a generous center island, subway tile backsplash, and a bright breakfast area that flows effortlessly into the spectacular sunroom. Bathed in natural light from soaring windows and skylights, this versatile space offers panoramic views of the backyard and golf course, making it the perfect place to relax or entertain year-round. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully renovated spa-inspired bath featuring a custom tiled walk-in shower, infrared sauna, and premium finishes. Upstairs, you'll find three generously sized bedrooms, including a private en-suite and a Jack-and-Jill bath, providing comfort and privacy for family and guests alike. An unfinished basement offers endless possibilities for future living space, fitness, recreation, or storage. Outside, enjoy the beautifully landscaped yard, expansive deck, and picturesque setting overlooking one of Indiana's premier golf communities. With quality updates throughout, generous living spaces, and an unbeatable location in the Sand Creek Subdivision, this is a rare opportunity to enjoy refined golf course living while having easy access to Chicago, The Dunes, Lake Michigan and more!

1591 Hogan Avenue, Chesterton

Listing courtesy of Stefanie Neal from BHHS Indiana Realty.

$529,900

4 Beds ⋅ 4 Baths ⋅ 841929 MLS ⋅ 2,970 SqFt. ⋅ Lauren Piazza

First Time on the Market! Proudly offered by its original owner, this exceptional property presents a rare opportunity to own a private retreat nestled on 5 picturesque acres. You will notice quality craftsmanship & attention to detail throughout the home. Surrounded by mature trees and abundant wildlife, the property features a cleared walking trail, a dedicated hunting area, a cozy fire pit, an apple tree, and a peaceful setting you'll enjoy year-round. Designed for both everyday living and entertaining, the home offers 4 bedrooms and 4 bathrooms with generous living spaces throughout. The spacious eat-in kitchen includes a pantry, built-in space saver and room for the whole family to gather for meals. The oversized living room is highlighted by a beautiful wood-burning fireplace and a large sliding glass door that showcases the serene backdrop. Step outside onto the expansive deck overlooking the private backyard--an ideal space for morning coffee, evening sunsets, or just relaxing with friends and family. The primary suite features an updated 3/4 bath and ample closet space. Throughout the home you'll find numerous custom built-in storage solutions and spacious closets designed with organization and storage in mind. The finished lower level expands your living space with a massive family room centered around a second wood-burning fireplace, complete with a convenient exterior-access wood storage cabinet for easy restocking. The lower level also offers a spacious fourth bedroom, w/ a bonus room connected & a half bath. A full bathroom, laundry room, and a dedicated tool/workshop room, provide endless possibilities for hobbies, guests, or multi-generational living. Additional highlights include oversized 2 car garage, a metal storage shed, a buoy/storage shed. If you've been searching for privacy, nature, and a home that has been lovingly maintained by one owner, you'll want to see this one! Survey & original blueprints attached for added peace of mind.

1089 N 200 W, Chesterton

Listing courtesy of Lauren Piazza from Realty Executives Premier.

$869,900

4 Beds ⋅ 5 Baths ⋅ 841275 MLS ⋅ 4,299 SqFt. ⋅ Stefanie Neal

Within the gated Sand Creek community, this beautiful custom residence blends timeless architecture with thoughtfully curated designer updates, creating a home that is both elegant and inviting. Rich hardwood flooring, extensive millwork, designer selected custom lighting, and refined finishes elevate every space while offering exceptional comfort. At the heart of the home, the fully renovated kitchen showcases custom cabinetry, quartz countertops, a designer tile backsplash, stainless steel appliances, combination microwave and double wall ovens, gas cooktop, and kitchen island. It flows seamlessly into the breakfast area, sunroom, formal dining room, and great room featuring exposed wood beams, custom built-ins, and a striking floor-to-ceiling stone fireplace, creating an open concept feel. The main-level primary suite is a true retreat with private access to the expansive deck and a stunning spa-inspired bath featuring a steam shower, oversized tile, dual sink vanity, premium fixtures, and an oversized walk-in shower with multiple shower heads along with a custom designed closet. Upstairs offers three spacious bedrooms, two full baths, and a large bonus room ideal for a home office or flexible living space. The finished daylight basement is designed for entertaining with a spacious family room, stone fireplace, custom wet bar, recreation area, full bath, and abundant storage. Outdoor living is equally impressive with an expansive deck, screened gazebo, hot tub, paver patio, mature landscaping, and irrigation system, creating a private setting for entertaining or relaxing. Additional highlights include finished three-car garage with custom storage and the close proximity to easily join Sand Creek Country Club for its exceptional amenities, including championship golf, swimming, fitness, tennis, dining, and year-round social events. Thoughtfully updated, timeless design and modern luxury, this exceptional home offers a lifestyle at an exceptional value!

1035 Kilarney Road, Chesterton

Listing courtesy of Stefanie Neal from BHHS Indiana Realty.

$359,900

4 Beds ⋅ 2 Baths ⋅ 840771 MLS ⋅ 1,975 SqFt. ⋅ Geremy Rinker

Welcome to 3624 Fairway Drive in Chesterton's desirable Golfview Estates! Offering nearly 2,000 square feet of living space, this 4-bedroom, 2-bath quad-level home provides the room and flexibility today's buyers are looking for. The home's multi-level design creates distinct spaces for gathering, relaxing, entertaining, working from home, or simply spreading out. Step inside to vaulted ceilings, warm bamboo hardwood flooring, a welcoming fireplace, and multiple living areas filled with possibilities. Outside, the generously sized corner lot and expansive two-tier deck create an inviting setting for summer cookouts, entertaining friends and family, or enjoying a quiet evening at home. Beyond the property itself, you'll love everything this location has to offer. Golfview Estates features neighborhood walking opportunities, a playground and park, while nearby trails, the Indiana Dunes National Park, South Shore Line, shopping, dining, and major highways put recreation and everyday conveniences within easy reach. Commuters will also appreciate convenient access toward Chicago and the surrounding Northwest Indiana communities. Located within the Duneland School Corporation, 3624 Fairway Drive offers a wonderful combination of space, location, and versatility in an established Chesterton neighborhood. Come see the possibilities and imagine making this home your own!

3624 Fairway Drive, Chesterton

Listing courtesy of Geremy Rinker from @properties/Christie's Intl RE.

$699,000

4 Beds ⋅ 5 Baths ⋅ 839799 MLS ⋅ 3,983 SqFt. ⋅ Lana Conroy

Light, bright and thoughtfully designed, this custom-built brick home offers over 4,000 square feet of exceptional living space in the heart of Chesterton. The inviting main level showcases beautiful hardwood floors, a cozy fireplace an open concept living area, a separate den that could be turned into a fifth bedroom and a formal dining room. The well-appointed kitchen offers abundant cabinetry, a large pantry, center island and brand-new stove and refrigerator. Step outside to the lovely screened in porch and enjoy peaceful views of nature while listening to the birds sing. Upstairs, two bedrooms feature private en-suites while the remaining bedrooms share a convenient jack and jill bathroom. A hidden bonus room adds a touch of charm and creativity, offering the perfect space for a playroom, gaming room, office, craft room or additional den. The finished lower level is an entertainers dream, complete with a spacious rec room, pool table and wet bar. Major updates include a new roof in 2025, furnace and central air in 2022 and the peace of mind of a whole house generator. This one-of-a-kind property combines space, character, and functionality in a location you will love to call home.

543 Windridge Drive, Chesterton

Listing courtesy of Lana Conroy from Coldwell Banker Realty.

$309,900

4 Beds ⋅ 2 Baths ⋅ 838403 MLS ⋅ 2,242 SqFt. ⋅ Carla Ebert-Kienitz

Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 bedrooms plus an office, with character, space, and comfort throughout! The beautiful gourmet kitchen with cabinets galore is just waiting for you to host that special dinner party. The stunning formal dining room is perfect for entertaining, while the large living room with a spectacular fireplace creates the ideal place to cozy up on cool evenings. Now wait until you see the incredible upstairs retreat, a master suite to die for! Enjoy a walk-in closet that feels like an entire extra room along with your own private getaway featuring a grand 20x14 bathroom designed for relaxation and comfort. So much in this home is brand new! Beautiful arched doorways welcome you inside, while large windows flood the home with natural light. Gorgeous plank flooring flows throughout the home, complemented by new carpet in the bedrooms. Outside, you'll love the huge corner lot, fantastic location, fully fenced backyard, and gorgeous deck where you can sit and sip your favorite beverage while enjoying your own peaceful tranquility. ROOF AND GUTTERS are less than 7 months old! A fantastic 2.5-car detached garage adds even more convenience and storage space. There's even a welcoming front porch perfect for relaxing and watching the world go by. Step into tranquility with this beauty... priced under market value! and ready to welcome you home!

769 S Calumet Road, Chesterton

Listing courtesy of Carla Ebert-Kienitz from Century 21 Circle.

$440,000

4 Beds ⋅ 3 Baths ⋅ 837890 MLS ⋅ 1,953 SqFt. ⋅ Lisa Gaff

Welcome home to this beautiful 4-bedroom, 2.5-bath two-story in the desirable Village of Burns Harbor community! This thoughtfully designed home features an open-concept layout filled with natural light, a spacious kitchen with quartz countertops and stainless steel appliances, and plenty of room for entertaining. Upstairs you'll find generously sized bedrooms including a comfortable primary suite. The unfinished basement offers endless possibilities for future living space, storage, or recreation. Located in the Duneland School District and just minutes from the Indiana Dunes, South Shore train line, shopping, and an easy commute to Chicago. Don't miss your opportunity to own a home in this growing community!

1162 (lot 183) Putman Place, Chesterton

Listing courtesy of Lisa Gaff from White Hat Realty Group, LLC.

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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.