Chesterton Homes for Sale

Welcome to Chesterton, Indiana – a charming town that beautifully blends small-town warmth with modern conveniences. Nestled in the picturesque landscape of Porter County, Chesterton is a hidden gem that offers a vibrant community atmosphere, rich history, and an abundance of outdoor activities. Known for its friendly residents and strong sense of community, this town is perfect for families, professionals, and retirees alike.

One of the standout features of Chesterton is its proximity to the stunning Indiana Dunes National Park, where residents can enjoy miles of sandy beaches, scenic trails, and breathtaking views of Lake Michigan. The town is also home to a variety of local shops, restaurants, and annual festivals that celebrate its unique culture and heritage. With excellent schools and a commitment to community service, Chesterton provides an ideal environment for raising children or enjoying a peaceful retirement.

For those looking to make Chesterton their home, the real estate market offers a diverse range of options. From charming historic homes with character to modern new constructions, there’s something for everyone. Whether you're searching for a cozy bungalow, a spacious family home, or a sleek townhouse, the homes for sale in Chesterton cater to a variety of lifestyles and budgets.

With its delightful blend of nature, community, and convenience, Chesterton is not just a place to live; it's a place to thrive. Explore the available homes for sale today and discover your perfect slice of Indiana paradise!

Newest Chesterton Homes for Sale

$295,000

3 Beds ⋅ 3 Baths ⋅ 842952 MLS ⋅ 1,288 SqFt. ⋅ Jennifer Colvin

Welcome to this charming 3-bedroom, 2 1/2 bath ranch nestled in the established Chestnut Hill neighborhood! This inviting home offers comfortable one-level living with a spacious eat-in kitchen, providing plenty of room for everyday meals and entertaining. A 2-car garage offers convenient parking and additional storage space. The fenced-in backyard provides a wonderful space for outdoor enjoyment, pets, gardening, or relaxing with family and friends. With three bedrooms, two full bathrooms, and a desirable ranch layout, this home offers both convenience and functionality in a well-established neighborhood. Don't miss the opportunity to make this Chestnut Hill gem your new home!

610 Fox Point Drive, Chesterton

Listing courtesy of Jennifer Colvin from McColly Real Estate.

$283,500

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.

$900,000

5 Beds ⋅ 5 Baths ⋅ 842756 MLS ⋅ 6,360 SqFt. ⋅ Alexis Metcalf

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

Listing courtesy of Alexis Metcalf from Seramur Properties, LLC.

$240,000

3 Beds ⋅ 1 Baths ⋅ 842596 MLS ⋅ 1,784 SqFt. ⋅ Marcia Forcey

Welcome home to this inviting 3 bedroom, 1 bath residence located in the desirable community of Porter. Perfect for first-time homebuyers, those looking to downsize or anyone seeking a comfortable place to call home. This property offers a blend of charm, functionality and convenience. Conveniently located near local parks, schools and major highways. Also its just a short drive tin Indiana Dunes and Lake Michigan beaches.

107 Francis Street, Chesterton

Listing courtesy of Marcia Forcey from McColly Real Estate.

$249,900

3 Beds ⋅ 1 Baths ⋅ 842569 MLS ⋅ 977 SqFt. ⋅ Lindsay Phelan

Welcome home to this beautifully renovated 3-bedroom, 1-bath home that's truly move-in ready! Completely updated from top to bottom, this home features all new mechanicals, giving you peace of mind for years to come. The bright and modern kitchen comes complete with brand-new stainless steel appliances that stay with the home. Outside, you'll find a detached 2-car garage, offering plenty of space for parking and additional storage. The backyard provides space for entertaining, or simply relaxing outdoors. Conveniently located close to shopping, restaurants, and everyday amenities, with quick access to major highways for an easy commute. Don't miss this incredible opportunity to own a beautifully updated home--schedule your showing today!

400 Woodlawn Avenue, Chesterton

Listing courtesy of Lindsay Phelan from RE/MAX Executives.

$539,900

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.

$1,100,000

3 Beds ⋅ 3 Baths ⋅ 842375 MLS ⋅ 5,007 SqFt. ⋅ Alisha Fowler

Offered for the first time in nearly two decades, this exceptional custom ranch is a rare opportunity in the highly sought-after Sand Creek community. Perfectly positioned along the golf course, the home showcases breathtaking fairway views and the effortless main-level living today's buyers are searching for. Featuring three spacious bedrooms, a thoughtfully designed open floor plan, a custom gourmet kitchen with high-end appliances, and timeless craftsmanship throughout, every detail reflects quality and pride of ownership. Outside, the impeccably maintained grounds create a private setting that perfectly complements the home's picturesque surroundings. Meticulously cared for and rarely available, this is luxury golf course living at its finest.

1745 Nelson Drive, Chesterton

Listing courtesy of Alisha Fowler from Seramur Properties, LLC.

$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.

$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.

$449,900

3 Beds ⋅ 2 Baths ⋅ 842029 MLS ⋅ 1,488 SqFt. ⋅ Debra Lightfoot

LUXURY MEETS NATURE! On nearly an acre of land within charming Chesterton, this modern ranch home strikes the a rare balance of privacy, comfort and convenience. Relax on the covered patio surrounded by the sights and sounds of nature, or gather your guests around a fire pit in the secluded backyard. With no HOA and plenty of land, there is the opportunity to craft your vision on this exceptional site. Polished concrete floors with radiant in-floor heating provide year-round comfort, ease of maintenance, and reflect a design philosophy that celebrates natural materials and enduring craftsmanship. Soaring ceilings, expansive windows, and timeless finishes create a bright, inviting great room that feels both grand and comfortable. Just a few moments exploring the chef's kitchen will reveal curated details that elevate both cooking and entertaining. Designed as a relaxing retreat, the primary suite offers patio access, a walk-in closet, and a spa-inspired ensuite. Two additional bedrooms provide flexibility for both guests and a home office. Energy efficient and low maintenance features throughout make this home as functional as it is beautiful. Ideally located in Chesterton with easy access to the Prairie Duneland Trailhead, Dogwood Park, Migratory Bird Sanctuary, European Market, new YMCA campus, Duneland Schools and the Indiana Dunes.

2645 W 1100 N, Chesterton

Listing courtesy of Debra Lightfoot from McColly Real Estate.

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 841986 MLS ⋅ 4,361 SqFt. ⋅ Danelisse Hill

Timeless elegance defines this stately all-brick residence, perfectly positioned on a rare .69-acre pond lot within the prestigious gated, golf course community of Sand Creek. Backing to tranquil water with desirable southern exposure, this exceptional property is filled with natural light while offering peaceful views from two rear patios. Designed for both comfortable living and effortless entertaining, the main level showcases rich hardwood flooring, tray ceilings, formal living and dining rooms, and a private office with extensive custom built-ins. The chef's kitchen is beautifully appointed with commercial-grade stainless steel appliances, including a newer Wolf range, Thermador dishwasher, Viking refrigerator, double ovens, two sinks, abundant cabinetry, and a spacious pantry. The adjoining keeping room features a second fireplace and wet bar, creating an inviting gathering space. The main-floor primary suite offers a spacious walk-in closet and a beautifully remodeled spa-inspired bath. Upstairs are three generously sized bedrooms, including one with a private ensuite and two connected by a Jack-and-Jill bath. An oversized upper-level family room with two built-in desks provides flexible living space while overlooking the pond. The unfinished basement offers endless possibilities for future expansion. Recent improvements include a new roof (2021), new HVAC system, backup generator, tankless water heater, updated electrical, smart sprinkler system, remodeled primary bath, new lighting throughout, and a stunning motorized chandelier lift in the grand foyer for effortless maintenance. With its timeless architecture, exceptional craftsmanship, expansive lot, picturesque pond setting, and impressive list of upgrades, this remarkable home offers a rare opportunity to own one of Sand Creek's most distinguished properties.

1712 Snead Avenue, Chesterton

Listing courtesy of Danelisse Hill from Realty Executives Premier.

$264,900

3 Beds ⋅ 2 Baths ⋅ 841972 MLS ⋅ 1,131 SqFt. ⋅ Cody Potocki

Back on market at no fault of seller! Welcome to 252 S 21st St in Chesterton! This well-maintained home offers valuable updates, flexible living space, and outstanding garage/storage options, all tucked away at the end of a cul-de-sac. When you walk through the front door, you'll notice the vinyl flooring and open floor plan, with the floors flowing naturally into the kitchen and dining area. The renovated bathrooms provide a modern, updated feel alongside the main-floor bedrooms. Major improvements include a new roof, new air conditioner, new furnace, new gutters, and a newer sump pump, giving buyers added peace of mind. The home also features a partially finished basement with a family room, bedroom, and bathroom -- perfect for guests, hobbies, work-from-home needs, or additional living space. Out back, enjoy a deck overlooking the yard, ideal for relaxing, grilling, or entertaining. The property also stands out with two detached garages providing a total of four garage spaces, offering excellent room for vehicles, storage, tools, recreational equipment, or workshop potential. Conveniently located in Chesterton, this home combines practical updates, extra space, rare garage capacity, and a quiet cul-de-sac setting. Schedule your showing today!

252 S 21st Street, Chesterton

Listing courtesy of Cody Potocki from Prestige Midwest Realty, LLC.

Start Your Search

IDX information is provided by the Indiana Regional MLS and is exclusively for the consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data is deemed reliable but is not guaranteed accurate by the MLS.

Last updated

Updated . Information deemed reliable but not guaranteed.