Vintage homes for sale & real estate in Chesterton, IN

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ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Don’t miss your opportunity to view this charming four-bedroom, two-full-bath home located in Chesterton, Indiana! From the moment you step inside, you’ll fall in love with the character and warmth this home offers. One of the bedrooms is conveniently located on the main level, giving you great flexibility for guests, an office, or main-floor living. The location is truly ideal, situated in Duneland School District and within walking distance to parks, downtown Chesterton, and more. You’re also just minutes from the Indiana Dunes National Park, making it easy to enjoy beaches, trails, and all the natural beauty the area has to offer. Outside, the property features a spacio

$330,000

4 beds2 baths1,924 sq ft

525 S Calumet Rd, Chesterton, IN 46304

Main level bedroom • Fenced in yard • 0.45 acre lot

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
This 4 bedroom 1 3/4 bathroom house in the Morgan Park area of Chesterton is ready for you to call it home! New roof, gutter and siding, newer total HVAC, new hot water heater, new electrical panel and new dishwasher make this house as solid as it gets! Beautiful hardwood floors throughout the main level in the huge living room, dining room and both spacious bedrooms. Eat in kitchen with brand new floors (all new appliances stay-including washer and dryer in basement), fully updated bathroom and convenient enclosed breezeway from the garage to the kitchen gives you extra space. Upstairs find two additional bedrooms (window units just for extra air-both have HVAC run to them). The basement h

$299,000

4 beds2 baths2,375 sq ft

511 E Morgan Ave, Chesterton, IN 46304

New hot water heater • Newer total hvac • New dishwasher

(219) 227-8454

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Charming Farmhouse on 2 Acres in Chesterton Welcome to this beautiful 3-bedroom, 3-bath farmhouse set on a serene 2-acre lot in Chesterton. This home blends classic character with modern updates -- including new flooring, fresh paint, and an updated upstairs bathroom. Enjoy a spacious yard perfect for entertaining, gardening, or simply relaxing under the open sky. The property also includes a small outbuilding, ideal for a home office, gym, studio, or play space.

$349,900

3 beds3 baths1,866 sq ft

17 E 900 N, Chesterton, IN 46304

Spacious yard • Farmhouse on 2 acres • Small outbuilding

(219) 531-2288

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Escape to your own private paradise on this stunning 14+ acre property, where a tree-lined driveway winds gracefully through mature hardwoods, welcoming you home the moment you arrive. This is more than a home -- it's a lifestyle. The charming main farmhouse offers 4 spacious bedrooms and 2.5 baths, with an open and inviting floor plan centered around a gorgeous brand-new stone fireplace with efficient wood-burning insert -- perfect for cozy evenings. Recently upgraded with all-new Andersen windows featuring cutting-edge technology that blocks almost all harmful UV rays, your furniture, flooring, and curtains will stay vibrant for years. Crafted from patented Fibrex(r) composite material, t

$925,000

4 beds2.5 baths2,494 sq ft

450 E Greening Rd, Chesterton, IN 46304

Tree-lined driveway • Finished loft • Large pole barn

(219) 227-8454

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Old-World Charm Meets Modern Comfort in a Prime Location! Step back in time while enjoying every modern convenience in this absolutely charming 1.5-story Cape Cod home, built in 1910. This home perfectly blends old-world flair with contemporary living, offering 2 bedrooms and 1.5 bathrooms in a highly sought-after area. Inside, you'll be captivated by the architectural details. The open-concept kitchen flows seamlessly into a bright sunroom, creating an ideal space for daily living and entertaining. Unique finishes abound, including a mixture of faux tin ceilings, elegant crown molding, hardwood floors, and the soaring, vaulted ceiling of the sunroom. Modern amenities have been thoughtfull

$275,000

2 beds1.5 baths1,506 sq ft

422 Jefferson Ave, Chesterton, IN 46304

Open-concept kitchen • Vaulted ceiling • Faux tin ceilings

(888) 724-2836

Property at 1288 N Brummitt Rd, Chesterton, IN 46304, 3 beds, 2 baths

$250,000

3 beds2 baths1,765 sq ft

1288 N Brummitt Rd, Chesterton, IN 46304

(219) 246-5200

Property at 975 N 250 E, Chesterton, IN 46304, 4 beds, 2.5 baths

$350,000

4 beds2.5 baths3,828 sq ft

975 N 250 E, Chesterton, IN 46304

(219) 462-2411

Property at 701 S Park Dr, Chesterton, IN 46304, 5 beds, 3.5 baths

$380,000

5 beds3.5 baths3,246 sq ft

701 S Park Dr, Chesterton, IN 46304

(269) 469-8300

Property at 2009 W Porter Ave, Chesterton, IN 46304, 4 beds, 2 baths

$264,900

4 beds2 baths1,664 sq ft

2009 W Porter Ave, Chesterton, IN 46304

(219) 762-8578

Property at 1038 N Meridian Rd, Chesterton, IN 46304, 0.5 baths

$675,000

0 beds0.5 baths— sq ft

1038 N Meridian Rd, Chesterton, IN 46304

(219) 531-6683

Property at 2375 Indian Boundary Rd, Chesterton, IN 46304, 2 beds, 2 baths

$319,900

2 beds2 baths2,049 sq ft

2375 Indian Boundary Rd, Chesterton, IN 46304

(219) 440-0070

Property at 506 W Morgan Ave, Chesterton, IN 46304, 3 beds, 2 baths

$419,900

3 beds2 baths2,304 sq ft

506 W Morgan Ave, Chesterton, IN 46304

(219) 462-5478

Property at 1116 N 350 E, Chesterton, IN 46304, 4 beds, 3 baths

$925,000

4 beds3 baths4,546 sq ft

1116 N 350 E, Chesterton, IN 46304

(219) 531-6683

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NEW 6 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Easy on your pocket book this 2 BR Brick Ranch features hardwood floors and a full basement. Newer furnace and A/C. Oversized 2 car tandem garage and privacy fenced yard. Located in Pine Township. Quick possession.

$139,900

2 beds1 bath783 sq ft

1521 Birch St, Michigan City, IN 46360

Newer furnace • Full basement • Privacy fenced yard

(219) 714-7148

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Escape to your own 1.7-acre private retreat just minutes from Lake Michigan and the Indiana Dunes! This classic Cape Cod-style home blends cozy charm with incredible potential. Step inside to find two comfortable bedrooms plus a spacious open loft that's perfect for a home office, playroom, or easy conversion to a third bedroom. The flowing layout and natural light create a warm, inviting atmosphere ready for your personal touch. Outside, the possibilities are endless: a stocked fish pond for quiet evenings, a large tool shed for projects and storage, and a chicken coop (chickens not included!) for the hobby farmer in you. The expansive, mostly level lot offers plenty of room to garden, pla

$275,000

2 beds1 bath1,860 sq ft

1198 N Babcock Rd, Chesterton, IN 46304

Fish pond • Tool shed • Open loft

(219) 462-5478

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
A rare find in today's market, a solid brick ranch on a corner lot that is priced to sell! This 3 bedroom 2 bathroom home is ready for new owners. Bring your vision and make this ranch your own. 3 spacious bedrooms on the main floor with a semi-finished basement below give you lots of flexibility. Situated on a private corner lot, you will be amazed and how secluded you feel while still being close to everything.

$275,000

3 beds1.5 baths2,642 sq ft

6416 Old Porter Rd, Portage, IN 46368

Solid brick ranch • Corner lot • Private corner lot

(219) 218-1181

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Welcome Home! This property sitting on 1.04 ACRES has so many updated features you will not want to miss out on. BRAND NEW ROOF, GUTTERS, WINDOWS, APPLIANCES, GARAGE DOORS, FLOORING, LIGHT FIXTURES, BRAND NEW WASHER AND DRYER, AND MUCH MORE! On the main level you will be greeted by the cozy living space with a brand new electric fireplace and you will notice the rounded archways keeping the home's original charm. There's BRAND NEW FLOORING throughout the entire home. The kitchen has been fully renovated with stainless steel appliances and beautiful granite countertops. There is a HUGE primary bedroom as well as 3 additional bedrooms. The main level also includes a dining room leading out t

$347,900

4 beds2.5 baths2,890 sq ft

6600 Central Ave, Portage, IN 46368

New garage doors • New flooring • New gutters

(219) 462-2224

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Beautifully updated 3 Bedroom Ranch with hardwood and ceramic tile floors throughout. Kitchen features maple cabinetry, quartz counter top and all appliances. Loads of windows offering natural lighting. Brand new roof on house and 2.5 car garage, bath updated, partial basement with interior and exterior access. Move in ready!

$249,900

3 beds1 bath1,238 sq ft

308 Rankin St, Chesterton, IN 46304

Natural lighting • Quartz counter top • Updated bath

(219) 714-7148

ABOUT THIS HOME
Vintage Home for sale in Chesterton, IN:
Move right in and start enjoying Chesterton living! This spacious three-bedroom ranch offers a bright and inviting layout with a large living room and an oversized kitchen complete with a dishwasher and plenty of space to cook, gather, and entertain. Each bedroom offers comfortable dimensions-- the primary suite spans an impressive 19x11 ft! An additional large flex room provides endless options -- ideal for a home office, den, or second living room space area. Perfectly positioned on the north side of Chesterton just off Woodlawn Ave, this home offers unbeatable convenience -- less than six minutes to the South Shore Line Duneland Station, Indiana Dunes National Park, and I-94, plus close

$237,900

3 beds1 bath1,433 sq ft

319 Michigami Trl, Chesterton, IN 46304

8,712 sq ft lot • Garage • Built 1955

(219) 462-5478

Property at 315 Franklin St, Chesterton, IN 46304, 4 beds, 2 baths

$450,000

4 beds2 baths1,900 sq ft

315 Franklin St, Chesterton, IN 46304

(219) 926-1616

Property at 1563 Maine Ave, Michigan City, IN 46360, 3 beds, 1 bath

$264,999

3 beds1 bath1,008 sq ft

1563 Maine Ave, Michigan City, IN 46360

(219) 874-5209

Property at 173 W 700 N, Valparaiso, IN 46385, 3 beds, 2 baths

$399,900

3 beds2 baths3,282 sq ft

173 W 700 N, Valparaiso, IN 46385

(219) 464-3531

Property at 2375 Arrow St, Portage, IN 46368, 3 beds, 1 bath

$224,000

3 beds1 bath1,065 sq ft

2375 Arrow St, Portage, IN 46368

(219) 763-4565

Property at 2528 Mccool Rd, Portage, IN 46368, 5 beds, 3 baths

$319,900

5 beds3 baths3,000 sq ft

2528 Mccool Rd, Portage, IN 46368

Property at 250 W Lake Front Dr W, Beverly Shores, IN 46301, 4 beds, 3.5 baths

$2,395,000

4 beds3.5 baths3,485 sq ft

250 W Lake Front Dr W, Beverly Shores, IN 46301

(219) 243-2120

Property at 11754 W 400 N, Michigan City, IN 46360, 5 beds, 3.5 baths

$409,999

5 beds3.5 baths3,031 sq ft

11754 W 400 N, Michigan City, IN 46360

(219) 462-2224

Property at 2954 Airport Rd, Portage, IN 46368, 4 beds, 1.5 baths

$349,999

4 beds1.5 baths2,756 sq ft

2954 Airport Rd, Portage, IN 46368

(219) 462-2224

Property at 1602 N 500 E, Michigan City, IN 46360, 2 beds, 2 baths

$365,000

2 beds2 baths1,680 sq ft

1602 N 500 E, Michigan City, IN 46360

(219) 262-0086

Property at 799 N 400 E, Valparaiso, IN 46383, 4 beds, 2 baths

$354,900

4 beds2 baths2,732 sq ft

799 N 400 E, Valparaiso, IN 46383

(219) 262-0086

Property at 806 N 450 W, Valparaiso, IN 46385, 2 beds

$137,000

2 beds— baths976 sq ft

806 N 450 W, Valparaiso, IN 46385

(219) 227-8454

Property at 7 S Shore Ave, Beverly Shores, IN 46301, 5 beds, 1 bath

$499,000

5 beds1 bath1,800 sq ft

7 S Shore Ave, Beverly Shores, IN 46301

(219) 872-4811

Property at 1290 Old Porter Rd, Chesterton, IN 46304, 3 beds, 1.5 baths

$270,000

3 beds1.5 baths1,716 sq ft

1290 Old Porter Rd, Chesterton, IN 46304

(219) 462-2411

Property at 1601 Columbia Ave, Michigan City, IN 46360

$125,000

— beds— baths— sq ft

1601 Columbia Ave, Michigan City, IN 46360

(219) 872-4000

Based on information submitted to the MLS GRID as of Sat Nov 29 2025. All data is obtained from various sources and may not have been verified by broker or 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.

Vintage Homes for Sale in Chesterton

There are currently 13 vintage homes for sale in Chesterton at a median listing price of $420K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Chesterton stay on the market for 68 days and receive 1 offers. This map is refreshed with the newest listings in Chesterton every 15 minutes.

In the past month, 34 homes have been sold in Chesterton. In addition to houses in Chesterton, there were also 8 condos, 7 townhouses, and 1 multi-family unit for sale in Chesterton last month. Find your dream home in Chesterton using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in Chesterton are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Chesterton. Our Chesterton real estate stats and trends will give you more information about home buying and selling trends in Chesterton. If you're looking to sell your home in the Chesterton area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Chesterton with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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