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    Chesterton Real Estate Search

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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. 

    You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire. 

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    Contact us today to find out how we can be of assistance to you!

    Newest Chesterton Homes and Condos for Sale

    1245 Kilarney Road, Chesterton image
    1245 Kilarney Road, Chesterton $799,923

    Highly desirable Sand Creek property!!!! Presenting this custom built 3,800 square foot, 4 bedroom, 3.5 bath home. The list of updates to this property are endless!!! New...

    • 4 Beds
    • 3.5 Baths
    517 S 20th Street, Chesterton image
    517 S 20th Street, Chesterton $379,000

    Just like new! Are you looking for a single level floorplan? Here's your chance! This wonderfully remodeled home features 4 bedrooms, enough for everyone to have their ow...

    • 4 Beds
    • 2.5 Baths
    312 Roberts Road, Chesterton image
    312 Roberts Road, Chesterton $2,250,000

    Excellent location for a corporate or regional headquarters and/or distribution center. 21,300sf all steel flex building for sale or lease. Currently consists of 8,300sf ...

    1054 Mission Hills Court, Chesterton image
    1054 Mission Hills Court, Chesterton $449,900

    I'm proud to present this wonderful Townhome located in the sought after Sand Creek neighborhood. This home offers just over 2,500 finished square feet of living space an...

    • 3 Beds
    • 2.5 Baths
    1294 Chalemel Drive, Chesterton image
    1294 Chalemel Drive, Chesterton $309,900

    You'll love the four seasons room overlooking a wooded backyard and rear decks that are perfect for outdoor entertaining and gardening projects! Recently remodeled bathro...

    • 4 Beds
    • 2 Baths
    358 W North Boo Road, Chesterton image
    358 W North Boo Road, Chesterton $465,000

    Welcome home! In addition to many other updates from this last year, sellers have added: new baseboard trim, fresh paint, garage doors and openers, electrical & lighting ...

    • 3 Beds
    • 3 Baths
    1577 N 375  E, Chesterton image
    1577 N 375 E, Chesterton $389,000

    Nestled on over a half acre and surrounded by the gorgeous Indiana Dunes National Park, this nature lovers' paradise is waiting for you to call it home! Beautifully done ...

    • 2 Beds
    • 1.5 Baths
    499 Cherrywood Drive, Chesterton image
    499 Cherrywood Drive, Chesterton $359,900

    BETTER THAN NEW, stunning MAINTENANCE-FREE villa on a PREMIUM LOT in Chesterton's desirable Easton Park subdivision! Beautiful right from the curb with STONE ACCENTS and ...

    • 3 Beds
    • 1.75 Baths
    702 S 18th Street, Chesterton image
    702 S 18th Street, Chesterton $360,000 ▼

    Amazing 3 Bed 2 bath ranch located in Duneland school system,on a beautiful landscaped lot. The colorful and interesting plantings are a Master Gardeners dream. Enter an ...

    • 3 Beds
    • 2 Baths
    1335 Dune Meadows Drive, Chesterton image
    1335 Dune Meadows Drive, Chesterton $537,900

    Location! Location! Welcome home to this beautiful 5 bedroom , 4 bath Two-story located 1 mile from Lake Michigan, Indiana Dunes National Park, and just 45 minutes from ...

    • 5 Beds
    • 4 Baths
    200 Wren Court, Chesterton image
    200 Wren Court, Chesterton $415,000 ▼

    1.5 STORY CORNER LOT WITH FULL FINISHED BASEMENT IN ESTABLISHED, CONVIENT LOCATION SUBDIVISION! Large open entrance with hardwood floors through the main level. Beautiful...

    • 3 Beds
    • 3.5 Baths
    2021 Cherrywood Lane, Chesterton image
    2021 Cherrywood Lane, Chesterton $389,897

    Why wait for construction to begin? Here it is! A move-in ready three bedroom, two bathroom ranch in Chesterton's Easton Park, known as the Driftwood Villa.This ranch is ...

    • 3 Beds
    • 2 Baths
    4301 Westwood Lane, Chesterton image
    4301 Westwood Lane, Chesterton $434,999 ▼

    Enjoy an open setting in the Westwood Manor subdivision bi-level home, located just a few steps from the neighborhood park and in the same corner where the bus stops! The...

    • 5 Beds
    • 3.5 Baths
    899 St. Andrews Drive, Chesterton image
    899 St. Andrews Drive, Chesterton $358,990 ▲

    BEAUTIFUL NEW 2 story home in the St. Andrews Community! The desirable 1802 Plan features a main floor guest suite means this plan offers private living space both upstai...

    • 4 Beds
    • 3 Baths
    34 Blueberry Lane, Chesterton image
    34 Blueberry Lane, Chesterton $347,990

    Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan includes a versatile flex room and an open concept layout featuring ...

    • 4 Beds
    • 2.5 Baths
    1049 Preserve Lane, Chesterton image
    1049 Preserve Lane, Chesterton $350,990

    Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan includes a versatile flex room and an open concept layout featuring ...

    • 5 Beds
    • 2.5 Baths
    1046 Crabtree Lane, Chesterton image
    1046 Crabtree Lane, Chesterton $317,000 ▼

    A real Show Place. 4 bedroom, 3 bath brick and vinyl Tri-level in beautiful Chestnut Hills. Featuring large gathering room with gas fireplace. Master Suite is large with ...

    • 4 Beds
    • 3 Baths
    1201 Monterey Drive, Chesterton image
    1201 Monterey Drive, Chesterton $639,900

    This gorgeous 2 story home is Sitting pretty in The Highland's of Sand Creek! As you enter the foyer you will find the main floor office with with barn wood doors.This ho...

    • 4 Beds
    • 3.5 Baths
    1261 Redbud Drive, Chesterton image
    1261 Redbud Drive, Chesterton $319,000

    *Back on the market! The previous buyers are in the military and received some last minute orders requiring them to move elsewhere. The VA appraisal and inspection both c...

    • 4 Beds
    • 2.5 Baths
    1035 Blue Lake Circle, Chesterton image
    1035 Blue Lake Circle, Chesterton $342,990

    Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan includes a versatile flex room and an open concept layout featuring ...

    • 4 Beds
    • 2.5 Baths
    2061 Northwood Lane, Chesterton image
    2061 Northwood Lane, Chesterton $349,500 ▼

    Check out this beautiful, move in ready ranch in Chesterton's Easton Park subdivision! Why wait for new construction when you can have one now? This three bedroom two bat...

    • 3 Beds
    • 2 Baths
    412 Emerald Drive, Chesterton image
    412 Emerald Drive, Chesterton $343,000 ▼

    Welcome to this spacious 3000 sq. ft. open concept home with 3 bedrooms and 3 full-baths. The kitchen and dining room are connected with cathedral ceilings and a 3/4 wall...

    • 3 Beds
    • 3 Baths
    1064 Oak Trail Drive, Chesterton image
    1064 Oak Trail Drive, Chesterton $385,000 ▼

    What a wonderful house in a great neighborhood. This two story, five bedroom, 3 1/2 bathroom house has everything. Living room with the cathedral ceilings leads you to an...

    • 5 Beds
    • 4 Baths
    375 E Burdick Road, Chesterton image
    375 E Burdick Road, Chesterton $399,999 ▼

    NATURE LOVERS ENVY. This home is perfectly located between the thriving community of Valparaiso and the Lake Michigan beaches affectionately known as the Dunes. A very ...

    • 3 Beds
    • 3 Baths
    1033 Preserve Lane, Chesterton image
    1033 Preserve Lane, Chesterton $333,490

    Prepare to be impressed by this BEAUTIFUL NEW 2-story home in the The Preserve Community! The elegant 2202 Plan boasts a flex space and a guest suite with a walk-in close...

    • 5 Beds
    • 3 Baths
    899 Dunhill Drive, Chesterton image
    899 Dunhill Drive, Chesterton $355,990 ▲

    You will love this BEAUTIFUL NEW 2 story home in the St. Andrews Community! The desirable 1802 Plan features a main floor guest suite means this plan offers private livin...

    • 4 Beds
    • 3 Baths
    898 Dunhill Drive, Chesterton image
    898 Dunhill Drive, Chesterton $364,990 ▲

    Don't miss this opportunity to own a BEAUTIFUL NEW 2 Story home in the St. Andrews Community! The elegant 2002 Plan offers flex room on the main floor. The kitchen featur...

    • 4 Beds
    • 2.5 Baths
    108 Washington Avenue, Chesterton image
    108 Washington Avenue, Chesterton $367,000 ▼

    WELCOME HOME! SPACIOUS AND WELL MAINTAINED RANCH WITH FINISHED BASEMENT!4 BED, 3 Bath RANCH with 2 CAR GARAGE, and FULLY FINSHED BASEMENT.Searching for space? You'll find...

    • 4 Beds
    • 3 Baths
    1083 N 475  E, Chesterton image
    1083 N 475 E, Chesterton $399,900 ▼

    Wanna get away, but still be at home?! Look no further than this beautiful 2 Story Log Cabin home with 4 bedrooms and 2 bathrooms situated on over 2 acres! As you approac...

    • 4 Beds
    • 2 Baths
    532 Windridge Drive, Chesterton image
    532 Windridge Drive, Chesterton $399,900 ▼

    4 bedroom, 2.5 bath, brick and cedar 2 story with basement in Tanglewood subdivision on 1/4 acre lot. Cherry cabinets in kitchen, well-lit breakfast nook, formal dining r...

    • 4 Beds
    • 2.5 Baths
    1040 Wabash Avenue, Chesterton image
    1040 Wabash Avenue, Chesterton $3,600,000

    NNN lease, 3.5+ yrs of term remaining on current 5 year lease. Renewal option with 10% rent increase in 2nd year of renewal option. Building for sale only. Existing tenan...

    720 Tanglewood Lane, Chesterton image
    720 Tanglewood Lane, Chesterton $545,900

    UNDER CONSTRUCTION. CURRENTLY IN ROUGHTS. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONSThe Aria Model is a home you must see to believe. This op...

    • 4 Beds
    • 2.5 Baths
    1040 Country Creek Lane, Chesterton image
    1040 Country Creek Lane, Chesterton $1,399,900

    ONLY 45 MILES to CHICAGO! Private 4.46A, Equestrian, Country, Timber Frame, Log Home Lodge Resort!! Looking for a full time residence or a sweet getaway? Own your own res...

    • 4 Beds
    • 2.75 Baths
    2016 Timberwood Lane, Chesterton image
    2016 Timberwood Lane, Chesterton $599,900

    Don't miss your chance for this new construction stunner! The two story foyer and impressive staircase greet you. Then walk into an open concept great room, nook and kitc...

    • 4 Beds
    • 2.5 Baths
    1014 Preserve Lane, Chesterton image
    1014 Preserve Lane, Chesterton $347,990 ▲

    Prepare to be impressed by this BEAUTIFUL NEW 2-story home in the The Preserve Community! The elegant 2202 Plan boasts a flex space and a guest suite with a walk-in close...

    • 5 Beds
    • 3 Baths
    470 Eastwood Lane, Chesterton image
    470 Eastwood Lane, Chesterton $384,900 ▲

    HOME IS UNDER CONSTRUCTION. CURRENTLY IN DRYWALL. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.This is the gorgeous Sandstone Villa! If you are...

    • 2 Beds
    • 2 Baths
    2001 Timberwood Lane, Chesterton image
    2001 Timberwood Lane, Chesterton $531,900 ▲

    UNDER CONSTRUCTION, HOME IS IN FRAMING STAGE. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONSOpen concept ranch in desired Easton Park subdivisi...

    • 3 Beds
    • 2 Baths
    2010 Timberwood Lane, Chesterton image
    2010 Timberwood Lane, Chesterton $556,900 ▲

    HOME IS UNDER CONSTRUCTION, IN ROUGHS STAGE. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.The expanded Sycamore Model is a home you must see t...

    • 4 Beds
    • 2.5 Baths
    75 Canondale Drive, Chesterton image
    75 Canondale Drive, Chesterton $349,990 ▼

    Don't miss this opportunity to own a BEAUTIFUL NEW 2 Story home in the St. Andrews Community! The elegant 2002 Plan offers flex room on the main floor. The kitchen featur...

    • 4 Beds
    • 2.5 Baths
    2105 Northwood Lane, Chesterton image
    2105 Northwood Lane, Chesterton $374,900 ▲

    UNDER CONSTRUCTION, FOUNDATION ONLY.ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.If you are looking for Maintenance Free, you must see the Some...

    • 3 Beds
    • 2 Baths
    476 Eastwood Lane, Chesterton image
    476 Eastwood Lane, Chesterton $374,900 ▲

    NEW CONSTRUCTION, IN TRIMS STAGE.ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.If you are looking for Maintenance Free, you must see the Somerse...

    • 3 Beds
    • 2 Baths
    1023 Blue Lake Circle, Chesterton image
    1023 Blue Lake Circle, Chesterton $324,990 ▼

    Prepare to be impressed by this BEAUTIFUL NEW 2-story home in the The Preserve Community! The elegant 2202 Plan boasts a flex space and a guest suite with a walk-in close...

    • 5 Beds
    • 3 Baths
    1034 Blue Lake Circle, Chesterton image
    1034 Blue Lake Circle, Chesterton $338,990 ▲

    Prepare to be impressed by this BEAUTIFUL NEW 2-story home in the The Preserve Community! The elegant 2202 Plan boasts a flex space and a guest suite with a walk-in close...

    • 5 Beds
    • 3 Baths
    2009 Timberwood Lane, Chesterton image
    2009 Timberwood Lane, Chesterton $522,900 ▲

    UNDER CONSTRUCTION, CURRENT STAGE, TRIM CARPENTRY.Open concept ranch in desired Easton Park subdivision. Home features vaulted ceilings in the living room w/ a stone gas ...

    • 3 Beds
    • 2 Baths
    119 S Calumet Road, Chesterton image
    119 S Calumet Road, Chesterton $674,900 ▼

    MAIN STREET TAP HOUSE is a must see for owner/operators. This turnkey opportunity includes building, business, assets, and liquor license. A truly iconic property locate...

    505 Grant Avenue, Chesterton image
    505 Grant Avenue, Chesterton $1,600,000 ▼

    This is a mixed use property zoned I-1. This commercial building is fully rented with multiple tenants used for offices and warehouse space. There are 36 storage units of...

    1200 N St Rd 49, Chesterton image
    1200 N St Rd 49, Chesterton $749,000 ▲

    Strategic northeast corner at a signalized intersection on State Rd 49 sits just 1/4 mile south of the Indiana Dunes Visitors Center at the intersection of the cutoff ro...

    371 E US Highway 20, Chesterton image
    371 E US Highway 20, Chesterton $499,900 ▼

    GREAT INVESTMENT PROPERTY In the Indiana Dunes Lakeshore. Custom Built 3250sq.ft. Ranch style all brick and stone home/office. 4 bedrooms 2.5 baths with a basement that h...

    371 E US Highway 20, Chesterton image
    371 E US Highway 20, Chesterton $499,900 ▼

    Beautiful Setting. Property boarders Indiana Dunes Lakeshore. Custom Built 3250sq.ft. Ranch style all brick and stone home/office. 4 bedrooms 2.5 baths with a 2000 sq. ft...

    • 4 Beds
    • 3 Baths
    988 N 350  E, Chesterton image
    988 N 350 E, Chesterton $1,400,000 ▼

    Beautiful rolling property in desireable Jackson Township suitable for development, horse farm, vineyard or your own private estate is waiting for you. Established trees ...

    Updated . Information deemed reliable but not guaranteed.

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