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$110,000
Imagine your dream home nestled among the trees on this beautiful 1.36-acre corner lot at 369 Ridgeview Drive. Located in Woodridge Hills, a private Jackson Township community known for its spacious wooded homesites and impressive custom residences, this property offers the rare opportunity to create a home designed entirely around your lifestyle. The generous corner setting provides flexibility for a striking home design, welcoming driveway and outdoor living spaces while preserving the natural beauty and privacy of the surrounding woods. Building plans are subject to applicable covenants and approvals. Enjoy a peaceful, tucked-away setting without giving up convenience. Downtown Chesterton's locally owned restaurants, boutiques, art scene, festivals and popular European Market are just minutes away. Spend weekends hiking, biking and enjoying Lake Michigan's shoreline at Indiana Dunes National Park, which protects 15 miles of beaches along the southern shore of Lake Michigan. For commuters or Chicago day trips, nearby Dune Park Station provides access to the South Shore Line, connecting Northwest Indiana directly with Millennium Station in downtown Chicago. With convenient access to Route 49, major expressways, Chesterton and Valparaiso, this location brings together privacy, natural beauty and everyday convenience. Bring your vision and create something truly remarkable at 369 Ridgeview Drive.

369 Ridgeview Drive, Chesterton
$250,000
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 ran to the property, all other permits needed.

1065 N 50 W, Chesterton
$579,900
4 Beds ⋅ 4 Baths
Unmatched curb appeal, custom craftsmanship, with 3.44 acres of privacy with 4 Bedroom and 4 Baths. This stunning Craftsman-style home offers an idyllic retreat within the coveted Duneland School District. From the moment you pull up to the expansive three-car garage. Featuring a generous 13 ft by 30 third bay perfect for a boat, workshop, or extra storage and see the gorgeous wrap-around front porch, you'll know you've found something special. Inside, the quality is undeniable 2x6 construction, solid wood doors, and wood trim throughout the main floor. Beautiful wood floors flow seamlessly through the entryway, dining room, kitchen, and hallway. Host gatherings in the elegant dining room, by solid wood columns and plantation shutters, or cook with ease in the spacious eat-in kitchen, complete with beautiful maple cabinets and an ample amount of counter and storage space. Step directly from the kitchen out to a charming screened-in porch, which opens to a durable Trex deck,ideal for outdoor dining and taking in views of your private acreage. Afterwards, relax in the impressive living room anchored by soaring vaulted ceilings and a warm gas fireplace. Main-floor primary sanctuary features direct access to the wrap-around porch and a spa-like ensuite bath complete with a double vanity, soaking tub, walk-in shower, private toilet closet, and a spacious walk-in closet. Down the hall, a secondary main-floor in-law suite with an adjacent 3/4 bath provides unmatched flexibility. As you head upstairs, you will notice the gorgeous wooden staircase. You'll find two generously sized bedrooms and a full bath with double sinks and along with an unfinished area above the garage offering incredible potential for future expansion. Downstairs in the partially finished basement adds even more versatile space, complete with daylight windows, a full bath, and direct interior stairs leading right up to the garage. For complete peace of mind, the home comes with Generac Generator

386 E 1050 N, Chesterton
$900,000
5 Beds ⋅ 5 Baths
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
$125,000
Create the possible! These in town, Duneland Cove lots, have municipal water & sewer, gas and electric available. Convenient easy transit to highways, rails, shopping, schools, parks, playgrounds and within minutes to our beautiful Lake Michigan shoreline beaches, parks and trails. All permits required, No HOA, covenants and restrictions apply.

898 Lot 131 Michael Drive, Chesterton
$125,000
Welcome to the undeveloped phase of the desirable Hunters Glen Subdivision in Porter, Indiana--an excellent opportunity for builders or investors. This offering includes 8 spacious, wooded lots plus 2 additional parcels designated for roads and drainage infrastructure. Nestled in a peaceful, natural setting, this subdivision combines privacy with convenience. With easy access to I-94 and the South Shore Train, commuting to Chicago or nearby communities is a breeze. Enjoy the charm of Porter while being minutes from Indiana Dunes, Lake Michigan, and local amenities. Don't miss your chance to develop in one of Porter County's most sought-after areas. A buyer could apply to vacate the platted subdivision with the Town of Porter and build one house on the parcel(this would be contingent on Town of Porter approval).

860 Quail Ridge Circle, Chesterton
$625,000
4 Beds ⋅ 4 Baths
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
$199,900
10 Acre Estate Lot in Unincorporated Porter County. Lot A of a recorded, approved 5 lot subdivision Branham Meadows AVAILABLE in Chesterton, Indiana. This platted homesite offers approximately 340 feet of frontage on 1000 N and a deep 1,294-foot lot, ideal for a custom home, hobby farm, or long-term land investment in Northwest Indiana's Duneland area. The plat is recorded and approved, giving builders and buyers a ready-to-build acreage parcel with room to spread out. The land is sold without utilities in place. Buyers will install a private well and septic system, with electric and natural gas brought to the site. The open acreage sits in a quiet rural setting between 50 W and 100 W. Minutes from IN-49 and I-94, with downtown Chesterton shopping and dining a short drive north and the Indiana Dunes National Park and Lake Michigan beaches within easy reach. Commuters can access the South Shore Line for a direct ride to downtown Chicago, roughly an hour away. Bring your builder and your plans. Note that these lots cannot be further divided and permit one residential dwelling per lot. Additional accessory structures are permitted pursuant to porter county building code. The size of these lots create the potential for large structures.

62 W 1000 N, Chesterton
$199,900
10 Acre Estate Lot in unincorporated Porter County, rural Chesterton IN. Lot B of a recorded, approved 5 lot subdivision Branham Meadows. This platted homesite is a conventional rectangular lot with no trees to clear! The site offers approximately 340 feet of frontage on 1000 N and a deep 1,294-foot lot, ideal for a custom home, hobby farm, or long-term land investment in Northwest Indiana's Duneland area. The plat is recorded and approved, giving builders and buyers a ready-to-build acreage parcel with room to spread out. The land is sold without utilities in place. Buyers will install a private well and septic system, with electric and natural gas brought to the site. The open acreage sits in a quiet rural setting between 50 W and 100 W. Minutes from IN-49 and I-94, with downtown Chesterton shopping and dining a short drive north and the Indiana Dunes National Park and Lake Michigan beaches within easy reach. Commuters can access the South Shore Line for a direct ride to downtown Chicago, roughly an hour away. Note that these lots cannot be further divided and permit one residential dwelling per lot. Additional accessory structures are permitted pursuant to porter county building code. The size of these lots create the potential for large structures. Bring your builder and your plans and get away from the crowd!

68 W 1000 N, Chesterton
$199,900
10 Acre Estate Lot in Unincorporated Porter County, Chesterton IN. Lot C of a recorded, approved 5 lot subdivision Branham Meadows. All lots are conventionally shaped rectangular/square for ideal residential development with no trees to clear! This platted homesite offers approximately 340 feet of frontage on 1000 N and a deep 1,294-foot lot, ideal for a custom home, hobby farm, or long-term land investment in Northwest Indiana's Duneland area. The plat is recorded and approved, giving builders and buyers a ready-to-build acreage parcel with room to spread out. The land is sold without utilities in place. Buyers will install a private well and septic system, with electric and natural gas brought to the site. The open acreage sits in a quiet rural setting between 50 W and 100 W. Minutes from IN-49 and I-94, with downtown Chesterton shopping and dining a short drive north and the Indiana Dunes National Park and Lake Michigan beaches within easy reach. Commuters can access the South Shore Line for a direct ride to downtown Chicago, roughly an hour away. Note that these lots cannot be further divided and permit one residential dwelling per lot. Additional accessory structures are permitted pursuant to porter county building code. The size of these lots create the potential for large structures. Bring your builder and your plans and get away from the crowd!

76 W 1000 N, Chesterton
$199,900
10 acre ESTATE LOT parcel in newly subdivided Branham Meadows in UNINCORPORATED Porter County, CHESTERTON, IN. Lot D of a recorded, approved 5 lot subdivision. This platted homesite offers approximately 516 feet of frontage on 1000 N and a deep 903 foot lot, ideal for a custom home, hobby farm, or long-term land investment in Northwest Indiana's Duneland area. The plat is recorded and approved, giving builders and buyers a ready-to-build acreage parcel with room to spread out. The land is sold without utilities in place. Buyers will install a private well and septic system, with electric and natural gas brought to the site. The open acreage sits in a quiet rural setting between 50 W and 100 W. Minutes from IN-49 and I-94, with downtown Chesterton shopping and dining a short drive north and the Indiana Dunes National Park and Lake Michigan beaches within easy reach. Commuters can access the South Shore Line for a direct ride to downtown Chicago, roughly an hour away. Note that these lots cannot be further divided and permit one residential dwelling per lot. Additional accessory structures are permitted pursuant to porter county building code. The size of these lots create the potential for large structures. Bring your builder, your plans, and get away from the crowd!

84 W 1000 N, Chesterton
$199,900
Get Away From The Crowd with this 11 acre Estate Lot in beautiful rural setting located in Unincorporated Porter County, Chesterton IN, away from neighbors but close to town and highway access! Lot E of a recorded, approved 5 lot subdivision. This platted homesite offers approximately 500 feet of frontage on 100 W and a deep 1,050 foot lot, ideal for a custom home, hobby farm, or long-term land investment in Northwest Indiana's Duneland area. The plat is recorded and approved, giving builders and buyers a ready-to-build acreage parcel with room to spread out. The land is sold without utilities in place. Buyers will install a private well and septic system, with electric and natural gas brought to the site. The open acreage sits in a quiet rural setting between 50 W and 100 W. Minutes from IN-49 and I-94, with downtown Chesterton shopping and dining a short drive north and the Indiana Dunes National Park and Lake Michigan beaches within easy reach. Commuters can access the South Shore Line for a direct ride to downtown Chicago, roughly an hour away. Bring your builder and your plans! Tons of possibility here. Four other lots still available. Note that these lots cannot be further divided and permit one residential dwelling per lot. Additional accessory structures are permitted pursuant to porter county building code. The size of these lots create the potential for large structures.

981 N 100 W, Chesterton
$389,000
This 1.44 acre lot is located close to the Indiana Toll Road, I-94, the South Shore train station, The Indiana Dunes State Park, and the Indiana Dunes National Park. Across Highway 49 you will find Culver's, AJ's Pizza, Popeye's, Dunkin Donuts, Hilton Garden Inn, Bob Evans, and multiple medical and office buildings.

1022 N Old State Rd 49, Chesterton
$350,000
3 Beds ⋅ 3 Baths
Trade traffic for trailheads and design a home that completely reflects your soul. Tucked away on an expansive 2.03-acre wooded lot in Chesterton, this solid tri-level property is a dream canvas for the visionary buyer ready to bring a high-contrast, moody aesthetic to life. With 2,531 square feet, three bedrooms, and three bathrooms, plus a bonus room, the spacious layout features great architectural bones that practically beg for rich textures, deep color palettes, and a custom modern remodel. Location Highlights Outdoor Adventure: The Heron Rookery Trail and Dale B. Engquist Nature Preserve are practically at your doorstep. Spend your weekends exploring the Indiana Dunes State Park Nature Center or Coffee Creek Preserve. Top-Tier Education: Located within the highly desirable Duneland School Corporation boundaries. Easy Commuting: Enjoy the perfect balance of a secluded, peaceful retreat that is still highly connected--the Beverly Shores train station or by car is just a short drive away for effortless city trips. (approx. 40 minutes to the city). Outside, the massive yard is surrounded by trees, offering ultimate privacy for a stunning outdoor living area, a native garden, or quiet mornings listening to birdsong. Ample parking and a 2.5-car garage mean there's plenty of room for your weekend toys and guests. Opportunities that blend acreage, top schools, immediate trail access, and true renovation potential don't last long. Schedule your tour today. Home is being sold AS-IS.

397 E 1300 N, Chesterton
$1,500,000
Prime commercial opportunity with endless potential! Situated on just over an acre along a high-traffic roadway, this unique property features four buildings totaling nearly 6,500 square feet. Exceptional visibility and easy access make this an ideal location for a variety of business ventures, investment opportunities, retail, office space, storage, service industries, or mixed-use possibilities. The expansive lot offers ample parking, room for expansion, and flexibility to fit your vision. Whether you're looking to grow your business, start a new venture, or add to your investment portfolio, this property delivers location, exposure, and opportunity all in one package. Don't miss your chance to own a versatile commercial property in a prime location with unlimited potential!

1147 N Salt Creek Road, Chesterton
$420,000
3 Beds ⋅ 2 Baths
Looking for a place in Chesterton where you can actually breathe? This peaceful 2.2-acre country retreat offers the perfect balance of wide-open green space and a home designed for everyone to have their own corner. The main house features airy vaulted ceilings, a large country kitchen with stainless steel appliances, and oversized bedrooms with deep closets, plus extra attic storage in both garages. A standout feature is the clever "related living" setup: just close the French doors to create a fully private apartment complete with its own kitchen, laundry, and appliances. You can soak up the views year-round from the heated sunroom, which overlooks an above-ground pool with a wrap-around sun deck, or choose between the large party-sized fire pit and the smaller, cozy one for quieter nights. To top it all off, the property includes a massive 40' x 60' fully insulated pole barn with concrete floors, electric, and even a built-in bedroom and bathroom. With double barn doors and a drive-through exit for easy rear parking, this is the ultimate setup for hobbies, guests, or just enjoying the quiet life. Located in the award-winning Chesterton/Duneland School District, convenient to all major highways, don't wait - schedule your showing today!

141 W 900 N, Chesterton
$64,900
Nature lover's paradise. Beautiful 1.46 acres lot in town. Coffee Creek runs through the south and west of the property. Coffee Creek is a tributary of Lake Michigan. Take a short kayak ride from Coffee Creek in your yard to the Calumet River and then on to Lake Michigan. Go catch some fresh salmon, see deer, beavers and a host of other nature sights. Build a new home on this property and enjoy Duneland Schools and all of the benefits of living in the country right in town. Zoned R2 . You an also build a duplex, nursing home or retirement community. There are so many possibilities. Close to beaches, Dunes National Lakeshore, SouthShore Line, shopping and restaurants.

000 Grady Street, Chesterton
$1,479,999
4 Beds ⋅ 5 Baths
Welcome to your private Northwest Indiana retreat in desirable Jackson Township--where space, luxury, and nature come together on just over 15 stunning acres. This all-brick estate offers the perfect blend of elegance and outdoor adventure, featuring 4 bedrooms and 5 bathrooms, thoughtfully designed for both everyday living and unforgettable entertaining. Inside, you'll find a generously sized kitchen with granite counters and stainless appliances, including a 6-burner cooktop with a griddle. 4 bedrooms include a spacious primary suite that serves as a true sanctuary, complete with a large en suite bath and plenty of room to unwind. Two additional bedrooms also feature private en-suite bathrooms, providing comfort and privacy for family or guests. The home offers many living spaces filled with natural light, including a beautiful sunroom with a hot tub--the perfect place to relax year-round. Conveniently located nearby is a dedicated bathroom designed to service the pool area. Step outside and experience a property that truly feels like a personal resort. Enjoy summers by the in-ground pool, host gatherings on the expansive deck, or explore your own private walking trails and mature woods. The stocked pond adds to the peaceful setting and creates the perfect spot for fishing, quiet reflection, or simply taking in the scenery. The unfinished basement provides incredible opportunity for future expansion--whether you envision a home theater, gym, additional living space, or guest quarters. Located in the highly sought-after Duneland School District, this property offers the perfect balance of privacy and convenience. Just minutes away, you'll find the breathtaking beaches and trails of the Indiana Dunes National Lakeshore, while the South Shore Railway provides an easy commute to downtown Chicago.

1137 N 475 E, Chesterton
$100,000
Build-ready wooded homesite in desirable Pine Township. This approximately 1.5 plus acre parcel offers privacy and natural surroundings while still being conveniently located near Chesterton, major highways, and the Indiana Dunes. Significant due diligence work has already been completed, including wetland delineation, septic feasibility investigation, and site planning identifying a viable building envelope for construction. Engineering and health department documentation supports development of a 4-bedroom home with septic system, helping reduce uncertainty and upfront costs for future buyers. Private driveway easement provides access to the property. A recent appraisal indicates a completed custom home on this site could support an approximate value near 792,000, demonstrating strong end-value potential for builders or homeowners planning a custom residence. This is a rare opportunity to purchase a wooded homesite with extensive preliminary work already completed. Additional documentation available upon request.

1300 N, Chesterton
$250,000
Location, Location, Location. Two adjacent Commercial building sites totaling 1.7 acres in established, fast growing Chesterton business park. Excellent location just South of downtown, off Calumet Rd., West of Highway 49 and quick access to the Indiana Toll Road and Highway 94. Utilities to the site, favorable B-3 Business Zoning.

123 & 127 Venturi Drive, Chesterton
$290,000
3 Beds ⋅ 2 Baths
Escape to your own private paradise at 214 Woodlawn Ave in Chesterton, IN, where this enchanting 1905 craftsman-inspired home sits on a breathtaking 1.66-acre wooded lot, enveloped in mature pines and lush greenery for ultimate seclusion and natural beauty. Just a leisurely stroll from downtown Chesterton's eclectic shops, cozy cafes, and community events, and mere minutes from the stunning trails and beaches of Indiana Dunes National Park, this 1,977-square-foot haven offers 3 bedrooms, 2 bathrooms, and effortless access to Chicago commutes--blending small-town charm with big-city convenience in the highly rated Duneland School District. From the moment you arrive, the home's warm light yellow siding and inviting deck beckon you into a world of timeless elegance. Step inside to a light-filled living room with dramatic cathedral ceilings, creating an open, airy retreat perfect for family gatherings. The adjacent kitchen inspires gourmet meals and connects seamlessly to the versatile den--ideal as a home office or guest space. Enjoy a full main-floor bathroom, convenient laundry/mud room, and direct access to the expansive covered patio, with the sprawling backyard perfect for barbecues or serene views. Upstairs, unwind in the luxurious primary bedroom suite with a spa-like en-suite bathroom and generous closet. The adaptable loft offers endless possibilities, complemented by a spacious second bedroom. The full unfinished basement awaits your vision as a media room or workshop, alongside a dedicated office. Modern comforts include central air, natural gas heating, municipal utilities. This isn't just a house--it's a legacy of tranquility and adventure. With historic soul and unbeatable location, it's ready to welcome you home.

214 Woodlawn Avenue, Chesterton
$60,000
Rare 1-Acre Wooded Lot in a Desirable Established Area! Conveniently located near schools, shopping, dining, and major commuter routes. The seller has obtained a land-clearing quote of approximately 10k, with costs varying based on how much of the lot the buyer chooses to clear. Enjoy the privacy, flexibility, and space to build your dream home. Large lots like this are hard to find - the seller is motivated and welcomes all offers!

Tbd Union Avenue, Chesterton
$220,000
WOW! Beautiful new lots in the NEWEST part of Sand Creek. Located in the gated community! Schedule your tour today! Lot 2 is located on the East Side of Chamborde Lane and is the 2nd lot in on the left as you enter the street. 1.07 Acres. Contact for gate code to tour.

1909 Chamborde Lane, Chesterton
$374,000
Make your move on this 10 + AC parcel that is *PUD designated* towards a light industrial/commercial type use. Located on 1050 N LaHayne Rd just off IN Hwy 149 N near Burns Harbor, this property provides tremendous access to all region highways such as I-94, Hwy 20 and Hwy 12. Buyer to verify site for intended use. Property surrounds the Springdale retention pond and has inlets for storm sewers per Seller. Plat sketch of Phase 1 Springdale Commoms is available. Zoned PUD as per Chesterton Zoning Map. Seller principal is licensed broker in referral.

Tbd County Rd 1050 N, Chesterton
$95,000
High traffic commercial lots. Two adjoining commercial properties totaling almost 2 acres on Indian Boundary Road. The property is zoned Business 2 which enables most retail applications, medical uses, and office functions. Property is in a TIF district.

108 Indian Boundary Road, Chesterton
$101,000
Create the possible! These in town, Duneland Cove lots, have municipal water & sewer, gas and electric available. Convenient easy transit to highways, rails, shopping, schools, parks, playgrounds and within minutes to our beautiful Lake Michigan shoreline beaches, parks and trails. All permits required, No HOA, covenants and restrictions apply.

Michael Dr. Lot 135, Chesterton

Updated . Information deemed reliable but not guaranteed.