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Chesterton, IN Restaurants for Sale

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Historic Chesterton Commercial Property For Sale
$460,000
3,398 SF

Historic Chesterton Commercial Property For Sale

125 S Calumet Rd, Chesterton, IN 46304

Commercial property with long-term tenant in historic Chesterton location.

  • Historic location in the heart of Chesterton
  • Building holds Flannery's Tavern, a tenant of over 100 years
  • Currently under a long‑term triple net (NNN) lease
  • Year Built: 1908
  • Heating: Hot Water and Forced Air
Updated: Feb 3
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Unique Train Car Commercial Opportunity
$450,000
6,236 SF

Unique Train Car Commercial Opportunity

301 Grant Ave, Chesterton, IN 46304

Own a unique business in four interconnected train cars!

  • Unique business opportunity: Own and operate a business within four train cars connected by a central building and eighty‑foot decks.
  • Prime location across from the Duneland Chamber of Commerce and quaint downtown Chesterton.
  • Proximity to high‑traffic areas including Indiana Dunes National Park and Lake Michigan.
  • Convenient access to the South Shore Train Station, Indiana Toll Road, and I‑94.
  • Located within the Chesterton Riverfront Development Project, offering the potential to apply for a liquor license.
Updated: Oct 16, 2025
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Unique Train Car Restaurant Opportunity
$450,000

Unique Train Car Restaurant Opportunity

Own and operate a business in four train cars!

301 Grant Ave, Chesterton, IN 46304
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Shovel-Ready Retail Site Available
Contact for pricing

Shovel-Ready Retail Site Available

0.71-acre site with high traffic and build-to-suit opportunity.

14 Coffee Creek Rd, Chesterton, IN 46304
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Based on your search, we've compiled 34 Potential Opportunities for your consideration. Besides 4 Active listings in Chesterton, IN, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 26 Off-Market properties to explore as potential leads

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Michigan City Commercial Property For Sale
Contact for pricing
3,955 SF

Michigan City Commercial Property For Sale

Commercial property with ample parking and highway frontage available for sale.

402 W Us Highway 20, Michigan City, IN 46360
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Restaurant Property on Franklin Street
Contact for pricing

Restaurant Property on Franklin Street

Restaurant property with frontage on Franklin Street, near Highway 20.

3940 Franklin St, Michigan City, IN 46360
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Valparaiso Mixed-Use Commercial Building
$1,100,000
10,086 SF

Valparaiso Mixed-Use Commercial Building

Multi-tenancy building in downtown Valparaiso with restaurant and office suites.

13 Lincolnway, Valparaiso, IN 46383
View details
Downtown Valparaiso Redevelopment Opportunity
Contact for pricing

Downtown Valparaiso Redevelopment Opportunity

Prime downtown Valparaiso location with redevelopment potential.

16-18 Indiana Ave, Valparaiso, IN 46383
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Explore Off-Market Properties in Chesterton, IN

Consider similar Off-Market properties in Chesterton, IN. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

139-141 Calumet Rd

139-141 Calumet Rd

RESTAURANT • 5,856 SF
Value Estimation by Request
139-141 Calumet Rd, Chesterton, IN 46304
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701 Plz Dr

701 Plz Dr

RESTAURANT • 1,480 SF
Value Estimation by Request
701 Plz Dr, Chesterton, IN 46304-1550
View details
475 Gtwy N Blvd

475 Gtwy N Blvd

RESTAURANT • 5,313 SF
Value Estimation by Request
475 Gtwy N Blvd, Chesterton, IN 46304-9660
View details
381 Indian Boundary Rd

381 Indian Boundary Rd

RESTAURANT • 2,665 SF
Value Estimation by Request
381 Indian Boundary Rd, Chesterton, IN 46304-1510
View details
715 Plz Dr

715 Plz Dr

RESTAURANT • 3,268 SF
Value Estimation by Request
715 Plz Dr, Chesterton, IN 46304-1550
View details
117 Calumet Rd

117 Calumet Rd

RESTAURANT • 5,968 SF
Value Estimation by Request
117 Calumet Rd, Chesterton, IN 46304-2433
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526 Indian Boundary Rd

526 Indian Boundary Rd

RESTAURANT • 10,958 SF
Value Estimation
$725,000
526 Indian Boundary Rd, Chesterton, IN 46304-1515
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798 Wabash Ave

798 Wabash Ave

RESTAURANT • 10,484 SF
Value Estimation by Request
798 Wabash Ave, Chesterton, IN 46304-2343
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535 Indian Boundary Rd

535 Indian Boundary Rd

RESTAURANT • 3,229 SF
Value Estimation by Request
535 Indian Boundary Rd, Chesterton, IN 46304-1514
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361 Wagner Rd

361 Wagner Rd

RESTAURANT • 3,772 SF
Value Estimation by Request
361 Wagner Rd, Chesterton, IN 46304-1752
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428 Calumet Rd

428 Calumet Rd

RESTAURANT • 1,914 SF
Value Estimation by Request
428 Calumet Rd, Chesterton, IN 46304-2453
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419 Calumet Rd

419 Calumet Rd

RESTAURANT • 1,173 SF
Value Estimation by Request
419 Calumet Rd, Chesterton, IN 46304-2431
View details
754 Indian Boundary Rd, Unit 1

754 Indian Boundary Rd, Unit 1

RESTAURANT • 3,534 SF
Value Estimation by Request
754 Indian Boundary Rd, Chesterton, IN 46304-1519
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702 Plz Dr

702 Plz Dr

RESTAURANT • 2,253 SF
Value Estimation by Request
702 Plz Dr, Chesterton, IN 46304-1549
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1300 Us-20

1300 Us-20

Restaurants • 2,046 SF
Value Estimation by Request
1300 Us-20, Chesterton, IN 46304
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900 Lincoln Ave

900 Lincoln Ave

RESTAURANT • 7,560 SF
Value Estimation by Request
900 Lincoln Ave, Chesterton, IN 46304-2241
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3000 Matson Dr

3000 Matson Dr

RESTAURANT • 4,266 SF
Value Estimation by Request
3000 Matson Dr, Chesterton, IN 46304-2416
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480 Indian Boundary Rd

480 Indian Boundary Rd

RESTAURANT • 4,708 SF
Value Estimation by Request
480 Indian Boundary Rd, Chesterton, IN 46304-1513
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552 Indian Boundary Rd, Unit 554

552 Indian Boundary Rd, Unit 554

RESTAURANT • 4,543 SF
Value Estimation by Request
552 Indian Boundary Rd, Chesterton, IN 46304-5504
View details
706 Plz Dr

706 Plz Dr

RESTAURANT • 2,771 SF
Value Estimation by Request
706 Plz Dr, Chesterton, IN 46304
View details

Chesterton, IN Restaurants Investment Opportunities Market Analysis

Explore 30 restaurants for sale in Chesterton, IN, showcased through 4 active listings on our real estate platform. These investment opportunities span a total of 568,895 square feet of properties for sale, with an estimated market value of $5,980,000.

Sale prices for restaurant properties in Chesterton, IN start at $240,000, averaging $284,761, and reaching up to $460,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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