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Living in proximity to the gorgeous Indiana Dunes and being an artist is much like being neighbors to Frank Lloyd Wright and being a designer; the inspiration for creating your own masterpieces is abundant. Perhaps it is for this reason Chesterton, Indiana has become a hub for artists like Craig Berg and Holly Jackson. Craig’s photographs can be purchased at Dunes Photography, as well as his restaurant Duneland Pizza, while Holly’s Matisse-inspired paintings can be purchased at her studio in Downtown Chesterton. Several other regional artists have works for sale at the Chesterton Art Center, many which feature dunescapes and other ecological treasures.

In addition to being an art-centric community, Chesterton is known for its many exciting annual festivals and events. For example, the European Market, which runs May through October is a popular destination, as are the year-round shops and restaurants here. In the heart of the community residents and visitors alike enjoy establishments like Octave Grill, Ivy’s Bohemia House, and Lucrezia Cafe. Serving up the best breakfast in the Cool North of Indiana is the 2018 Breakfast Wars Champion, the Northside Diner, also located in Chesterton is the 1950s-style Port Drive-In.

Beyond the art and the fabulous dining options, Chesterton also has excellent recreation opportunities at destinations like the 151-acre Coffee Creek Watershed Preserve, The Brassie Golf Club, and the Sand Creek Country Club. Also popular are entertainment venues like the Brown Mansion and adjoining Westchester History Museum. Shopping opportunities are also abundant at O’Gara & Wilson Ltd. Antiquarian Booksellers, Ella’s Bella, Ashley’s Jewelry by Design, Chelle’s, The Flower Cart, and other local establishments. With so much to offer in addition to its natural beauty and convenient location, Chesterton is an excellent place to buy a home. Homes for sale in Chesterton include a wide variety of housing styles, with both attached and detached options. Singles, couples, families, retirees, and everyone in between can easily find a Chesterton property to suit their needs and personal tastes. Because of the diversity of Chesterton real estate, listing prices for available Chesterton homes fall in a broad price range. If you would like to learn more about Chesterton homes or land for sale, please allow us to assist you and contact us at your earliest convenience.

Our website features the best Chesterton real estate search for homes, condos, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

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Newest Chesterton Homes and Condos for Sale

1116 N 350  E, Chesterton image
1116 N 350 E, Chesterton $980,000

Where CUSTOM+UNIQUE+PRIVACY MEETS! This 2 story home offers a private, serene country setting close to SAND CREEK GOLF COURSE! 5,000 SQ FT+ NESTLED ON A 10 ACRES W/ GAZEB...

  • 4 Beds
  • 3 Baths
1201 Monterey Drive, Chesterton image
1201 Monterey Drive, Chesterton $559,000

This upscale home with it's unique design and spacious interiors is perfect for both home living and entertaining guests, and also features excellent golf course views. W...

  • 4 Beds
  • 3.5 Baths
1623 Sarazen Drive, Chesterton image
1623 Sarazen Drive, Chesterton $1,195,000

Join the Sand Creek Community! Make this fabulous UPDATED 8,000 sqft, all brick home overlooking the private golf course & pond yours! Gather in your dream kitchen wi...

  • 5 Beds
  • 5.5 Baths
2315 Dunbar Street, Chesterton image
2315 Dunbar Street, Chesterton $374,566

Olthof Homes presents the energy savings Sequoia model featuring spacious 2 story open concept great room, 4 bedrooms, 2.5 baths, main floor laundry, flex/den space, part...

  • 4 Beds
  • 2.5 Baths
520 Emerald Drive, Chesterton image
520 Emerald Drive, Chesterton $319,900 ▲

New construction w/unmatchable style & quality complete in April, 2021! The welcoming foyer ushers you to the upper level where grand cathedral ceilings soar over th...

  • 3 Beds
  • 2.75 Baths
2021 Timberwood Lane, Chesterton image
2021 Timberwood Lane, Chesterton $434,900

Open concept ranch in desired Easton Park subdivision. Home features vaulted ceilings in the living room w/ a stone gas fireplace. Modern kitchen featuring white cabinets...

  • 3 Beds
  • 2 Baths
499 Cherrywood Drive, Chesterton image
499 Cherrywood Drive, Chesterton $329,900

If you are looking for Maintenance Free, you must see the Somerset Villa in Easton Park. Built by Nardo Homes they offer stunning elevations w/ full porch or stone entry ...

  • 3 Beds
  • 2 Baths
1754 Summerlin Drive, Chesterton image
1754 Summerlin Drive, Chesterton $364,900

2 Story Stone-Vinyl home situated on a wooded, landscaped lot on a cul-de-sac features 4 bedrooms, 2 3/4 baths with attached garage and a basement in Villages of Sand Cre...

  • 4 Beds
  • 2.75 Baths
1578 Sarazen Drive, Chesterton image
1578 Sarazen Drive, Chesterton $525,000

CLASSIC BRICK AND CEDAR TWO STORY OFFERS GREAT CURB APPEAL WITH WAGNER CONSTRUCTION QUALITY! Hardwood flooring throughout the first floor and newer carpeting upstairs. Th...

  • 5 Beds
  • 2.5 Baths
104 Washington Street, Chesterton image
104 Washington Street, Chesterton $329,900

New year, new home! New construction in Chesterton scheduled for completion end of March! This fabulous home boasts over 2,200 sq. ft. and is located minutes from the v...

  • 3 Beds
  • 2.75 Baths
102 Washington Street, Chesterton image
102 Washington Street, Chesterton $319,900 ▼

New construction in Chesterton, complete end of March 2021! Welcome home to this 1,600 sq. ft. ranch located minutes from the downtown district, award-winning schools, t...

  • 3 Beds
  • 2 Baths
210 E Tratebas Road, Chesterton image
210 E Tratebas Road, Chesterton $495,000

25 acres available in popular Jackson Township of Chesterton!! Perfect site to build your dream home. Open mix of mature trees and open clearings! Or a possible subdivisi...

777 S Calumet Road, Chesterton image
777 S Calumet Road, Chesterton $469,999

Peaceful Nature Views, Convenient location and Practical Living on 1 level that's walking distance to Downtown Chesterton is what you'll fall in love with at 777 S Calume...

  • 4 Beds
  • 3 Baths
1039 Country Creek Lane, Chesterton image
1039 Country Creek Lane, Chesterton $789,000

Proposed Construction by Younique Design + Build! This beautiful ranch on just under 5 acres of private, serene property with a full basement is ready for you to build! P...

  • 3 Beds
  • 3.5 Baths
705 Tanglewood Lane, Chesterton image
705 Tanglewood Lane, Chesterton $473,900 ▲

The New Aria Model by Nardo Homes is a home you must see to believe. This open concept plan offers a MAIN LEVEL master suite with soaking tub, tiled shower and separate v...

  • 4 Beds
  • 2.5 Baths
1700 Snead Avenue, Chesterton image
1700 Snead Avenue, Chesterton $1,399,000

Distinctively unique in every way is this custom Mediterranean Style home within the gates of Chesterton's Sand Creek. At over 8,000 sqft this home offers a jaw-dropping ...

  • 7 Beds
  • 8 Baths
2017 Timberwood Lane, Chesterton image
2017 Timberwood Lane, Chesterton $479,900

The Expanded Cobblestone Model by Nardo Homes is a home you must see to believe. This open concept plan offers breath taking views from the large picture window & is ador...

  • 4 Beds
  • 2.5 Baths
1097 Mission Hills Court, Chesterton image
1097 Mission Hills Court, Chesterton $367,000 ▼

Sand Creek Mission Hills Townhouse.&nbsp; The views are relaxing and the sound of the neighborhood water feature is just outside your door.<div>The foyer has a custom mar...

  • 2 Beds
  • 4 Baths
1485 Sand Creek Drive S, Chesterton image
1485 Sand Creek Drive S, Chesterton $649,000

Live your best life in this beautiful 4000 sq. ft. 4 bed, 5.5 bath home. Just steps away from the Midwest's premier residential golf club, this home has it all. Surrounde...

  • 4 Beds
  • 5.5 Baths
205 E Tratebas Road, Chesterton image
205 E Tratebas Road, Chesterton $750,000 ▼

---JUST REDUCED-- 38 BEAUTIFUL ACRES FOR SALE in the ultra popular Jackson Township of Chesterton! With the perfect mix of open clearings and natural terrain / mature tre...

75 W 1000  N, Chesterton image
75 W 1000 N, Chesterton $899,000

Development Opportunity in Chesterton Porter County Indiana. Approximately 69 acres of land situated just southwest of Chesterton. Utilities on site. Ideal for subdivisio...

975 N 50  W, Chesterton image
975 N 50 W, Chesterton $350,000

35 Acres for sale in Liberty Township. Utilities on site. Toll Road frontage, possible commercial use. Liberty Township, Duneland Schools. Owners also selling 69 acres ac...

1815 Carrick Lane, Chesterton image
1815 Carrick Lane, Chesterton $900,000

Living is easy in this prestigious residence with pond views. The open main floor plan encompasses a formal dining & living room (complete w floor to cathedral ceiling wi...

  • 6 Beds
  • 5.5 Baths
1560 Sand Creek Drive, Chesterton image
1560 Sand Creek Drive, Chesterton $474,900

Stunning golf course & pond views protect the privacy of this beautifully maintained brick and cedar 2 story in Sand Creek. Paring recreational country club lifestyle wit...

  • 4 Beds
  • 2.5 Baths
726 S Calumet Road, Chesterton image
726 S Calumet Road, Chesterton $350,000

<div><b>Go to our Virtual Tour for a COVID friendly tour.</b></div><div><b><br></b></div>The setting that the property and its buildings creates is felt the moment you ar...

  • 4 Beds
  • 2 Baths
726 S Calumet Road, Chesterton image
726 S Calumet Road, Chesterton $350,000

<div><b> go to our VIRTUAL TOUR!!</b></div><div><br></div>The setting that the property and its buildings creates is felt the moment you arrive. It has drawn in customers...

109 E 950  N, Chesterton image
109 E 950 N, Chesterton $335,000 ▼

A Unique Opportunity to own your own building with excellent exposure from IN Route 49 and the IN Toll Road. This parcel offers a 2,466 square foot office retail building...

1200  N, Chesterton image
1200 N, Chesterton $1,750,000 ▼

This Chesterton Location Offers A Lot of Potential!!! Wooded 35.4 Acre parcel that fronts 2 roads, Porter Avenue (1200 N) and Dickinson Rd. Developers some the prelimina...

315 S Calumet Road, Chesterton image
315 S Calumet Road, Chesterton $719,000 ▼

Expand, Start, your business. 9466 sq.ft bldg./ paved 2012 parking on .60acre in downtown.Brick 3stories. ADA accessible,parking.Great for restaurant/bar with banquet cen...

Updated . Information deemed reliable but not guaranteed.

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North Star Properties LLC
6212 U.S. Hwy 6 Suite 177
Portage, IN 46368

Phone: (219) 706-9139
Email: Sales@NorthStarPropertiesofIN.com

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