Chesterton Homes with Chesterton High School

Welcome to Chesterton, Indiana—a charming town nestled in the heart of Porter County, where small-town charm meets modern convenience. Known for its picturesque landscapes and vibrant community spirit, Chesterton offers a unique blend of suburban tranquility and easy access to urban amenities. With its close proximity to the stunning Indiana Dunes National Park and Lake Michigan, outdoor enthusiasts will find endless opportunities for hiking, biking, and enjoying the great outdoors.

One of the standout features of this delightful town is its commitment to education, highlighted by the esteemed Chesterton High School. Renowned for its academic excellence and diverse extracurricular programs, Chesterton High School is an integral part of the community, fostering a strong sense of pride among residents. Families seeking a nurturing environment for their children will find that the homes in Chesterton are not only surrounded by scenic beauty but also by a supportive educational framework.

Real estate in Chesterton is as diverse as its community, offering a variety of options from charming historic homes to modern new constructions. Whether you’re a first-time homebuyer or looking for a spacious family residence, Chesterton has something to suit every taste and budget. The town's welcoming neighborhoods, coupled with its strong sense of community, make it a perfect place to call home.

Experience the charm of Chesterton, where quality living meets a rich tapestry of history, nature, and community spirit. Discover your dream home today and become a part of this exceptional town that truly has it all!

Newest Chesterton Homes with Chesterton High School

$359,900

3 Beds ⋅ 2 Baths ⋅ 845085 MLS ⋅ 1,400 SqFt. ⋅ Samantha Cheatham

Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, perfectly situated on an expansive .48-acre lot within the highly sought-after Duneland School Corporation. With approximately 1,400 square feet of comfortable living space, this home offers the ideal blend of modern updates, functionality, and peaceful outdoor space. The home was completely taken down to the studs and renovated approximately five years ago, providing an impressive list of major improvements including new windows, roof, siding, furnace, air conditioning, vinyl flooring, well, septic system, and a newly paved driveway. The thoughtful updates continue with new storm doors in 2025 and, in 2026, a new shower with warranty, new shed, owned water softener, and new sump pump with a battery backup system. The stainless-steel appliances are included, and the versatile mudroom adds even more functionality with the flexibility to serve as a home office, den, or additional everyday living space. Step outside and enjoy the beauty and privacy of nearly half an acre. The spacious, well-maintained yard provides plenty of room for entertaining, gardening, pets, play, or simply enjoying your own outdoor retreat. With extensive updates, major systems already addressed, a beautiful lot, and the advantage of Chesterton schools, this is a home that offers both comfort and peace of mind. A wonderful opportunity to enjoy a move-in-ready property with nothing left to do but make it your own!

1430 N Veden Road, Chesterton

Listing courtesy of Samantha Cheatham from Realty Executives Premier.

$389,000

4 Beds ⋅ 3 Baths ⋅ 844907 MLS ⋅ 2,270 SqFt. ⋅ Branden Luna

Welcome to this 4 bedroom, 3 bath, 2-story home located in desirable Villages of Sand Creek. Main level offers a Formal Living Room as well as a Formal Dining, spacious Eat-in Kitchen which is open to the Family Room, and the Laundry Room. Upstairs you will find all 4 bedrooms freshly painted with newer carpet. The Primary Suite has an attached full bath with separate shower and tub and large walk-in closet. This home is situated on a cul-de-sac with a lovely view of the pond located across the walking path. This neighborhood is only 3 miles from the Indiana Dunes & Lake Michigan, close to restaurants, shopping, golf courses, and is an easy commute to Chicago.

378 Ballenisle Court, Chesterton

Listing courtesy of Branden Luna from Coldwell Banker Real Estate Gr.

$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.

$529,900

4 Beds ⋅ 3 Baths ⋅ 844236 MLS ⋅ 2,596 SqFt. ⋅ John Guest

Stunning, updated 2-story home nestled on a private, wooded 0.56-acre in-town lot in Chesterton! A grand 2-story entry welcomes you with luxury vinyl plank flooring extending throughout the main level, featuring a formal dining room. French doors from a den/office and flow into the family room, highlighted by a gas-start fireplace and a wall of windows showcasing the woods. The open-concept layout effortlessly connects the family room, eating area, and peninsula counter kitchen, which boasts painted oak cabinets, solid surface countertops, and recessed lighting. The rear hallway leads to the laundry room, a 3-car garage, and a vaulted ceiling screen porch with skylights. Step outside to a private, professionally designed outdoor oasis featuring a paver patio, a granite gas grill island with bar seating, a 55" outdoor TV in a storm box, a wood-burning fireplace, and a 4-person hot tub. Upstairs, the primary suite offers vaulted ceilings, a walk-in closet, a double vanity, a soaking tub, and separate shower, alongside three additional bedrooms and a full bath. The garage features a walk-up attic stairwell for easy storage or potential expansion with access through the 4th bedroom too. Complete with zoned 2010 Lennox HVAC and city utilities, this property offers quick access to Highways 49, I-90, and I-94 and near the Indiana Dunes National Park.

131 Beverly Drive, Chesterton

Listing courtesy of John Guest from Coldwell Banker Realty.

$242,900

843035 MLS ⋅ Marina Klein

Acreage in Liberty Township! Beautiful 4.12 Acre Lot in the sought out Duneland School District with just a 3 minute drive to Chestertion High School & 5 minutes to downtown Chesterton. No HOA, natural gas & electric have already been run to the property, soil borings have been completed, all other permits needed.

1065 N 50 W, Chesterton

Listing courtesy of Marina Klein from Blackrock Real Estate Services.

$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.

$269,900

2 Beds ⋅ 1 Baths ⋅ 842889 MLS ⋅ 1,204 SqFt. ⋅ Diane Cline

515 S Park Drive, Chesterton

Listing courtesy of Diane Cline from McColly Real Estate.

$97,500

842783 MLS ⋅ Matt Evans

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! Lot 21 in Phase VI-A backs directly to the golf course, on Marsh Course #4, offering beautiful views and a picturesque setting for your future custom home. Sand Creek Country Club features an outstanding array of membership amenities, including championship golf, swimming, tennis, fitness facilities, dining, social events, and year round recreational programs. Ideally located just minutes from the beautiful shores of Lake Michigan, this property also provides convenient access to the South Shore Line for an easy commute to downtown Chicago, approximately one hour away. Located within the highly regarded Duneland School Corporation, this homesite offers an outstanding combination of location, lifestyle, and accessibility. An adjoining golf course lot is also available for purchase under a separate MLS listing, providing the opportunity to expand your homesite or enhance your privacy. Buyer to verify lot dimensions, utilities, HOA information, building requirements, membership availability, and all intended uses.

1160 Monterey Drive, Chesterton

Listing courtesy of Matt Evans from RE/MAX Lifestyles.

$97,500

842782 MLS ⋅ Matt Evans

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! Lot 20 in Phase VI backs directly to the golf course, on Marsh Course #4, offering beautiful and a picturesque setting for your future custom home. Sand Creek Country Club features an outstanding array of membership amenities, including championship golf, swimming, tennis, fitness facilities, dining, social events, and year round recreational programs. Ideally located just minutes from the beautiful shores of Lake Michigan, this property also provides convenient access to the South Shore Line for an easy commute to downtown Chicago, approximately one hour away. Located within the highly regarded Duneland School Corporation, this homesite offers an outstanding combination of location, lifestyle, and accessibility. An adjoining golf course lot is also available for purchase under a separate MLS listing, providing the opportunity to expand your homesite or enhance your privacy. Buyer to verify lot dimensions, utilities, HOA information, building requirements, membership availability, and all intended uses.

1180 Monterey Drive, Chesterton

Listing courtesy of Matt Evans from RE/MAX Lifestyles.

$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.

$575,000

3 Beds ⋅ 3 Baths ⋅ 842133 MLS ⋅ 2,173 SqFt. ⋅ Tonia Dragon

PROPOSED CONSTRUCTION-Welcome to the Sonoma in Easton Park! This stunning custom-built, 1.5-story home offers over 2,100 square feet of luxury living with 3 bedrooms, 2.5 baths and a 3-car garage, all situated on a desirable corner lot. Step inside to a spacious foyer featuring a private office and convenient half bath before entering the impressive open-concept living space. The great room showcases beautiful hardwood floors, a custom fireplace, solid-core doors, an upgraded trim package and quality craftsmanship throughout. The kitchen is designed for both everyday living and entertaining, featuring quartz countertops, custom cabinetry, stainless steel appliances and a large walk-in pantry. The main-level primary suite offers a relaxing retreat with double sinks, a soaking tub and a spacious walk-in closet. Upstairs, you'll find two additional bedrooms...each with its own walk-in closet...a full bath, and a huge loft offering flexible space for a second living area, playroom, or entertainment space. Additional highlights include energy-smart features, zoned high-efficiency HVAC, a whole-home humidifier, fresh air intake, R-20 basement insulation, an egress window for a possible future bedroom and rough-in plumbing for a future bathroom. Located in the desirable Easton Park neighborhood, this home offers convenient access to Indiana Dunes National Park, the South Shore Line, major expressways, shopping, dining, and award-winning schools. Experience luxury, quality craftsmanship and thoughtful design in the Sonoma!

801 Ashwood Lane, Chesterton

Listing courtesy of Tonia Dragon from Better Homes and Gardens Real.

$216,000

3 Beds ⋅ 1 Baths ⋅ 842089 MLS ⋅ 945 SqFt. ⋅ Marcy Norman

This adorable 3 bedroom one bath home is ready for new owners. Kitchen has been updated. Quartz counter top with stainless steel sink and appliances. 1.5 car garage and storage shed as well. Yard is fenced. Duneland schools.

1025 W Porter Avenue, Chesterton

Listing courtesy of Marcy Norman from Trendsetters Realty, 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.