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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.
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Newest Chesterton Homes and Condos for Sale
Opportunities to become a central part of a thriving town are few and far between. This historic building with a successful, local tap business included, is that chance. ...
Tucked on a quiet street in downtown Chesterton you will find this sprawling ranch perfect for a growing family. This all brick open concept home offers over 1800 sq ft o...
- 4 Beds
- 4 Baths
READY NOW and available for showings! Designed for maintenance free comfort and modern living, the Brighton features an open concept design with 2 bedrooms and a flex roo...
- 2 Beds
- 2 Baths
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
This ranch home has it all on one level. Finished laundry room area, finished garage, deck, and a beautiful lot. Quality Low E windows. HERS energy rated home. Nine foot ...
- 3 Beds
- 2 Baths
MOVE-IN READY NOW! If you are looking for Maintenance Free, you must see the Driftwood Villa in Easton Park. Unlike anything in Porter County. They offer stunning elevati...
- 3 Beds
- 2 Baths
UNDER CONSTRUCTION. IN TRIMS. ESTIMATED COMPLETION, JAN/FEB, 2023. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.The Aria Model is a home you mu...
- 4 Beds
- 3 Baths
MOVE IN READY! ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.This is the gorgeous Sandstone Villa! If you are looking for Maintenance Free, you ...
- 2 Beds
- 2 Baths
UNDER CONSTRUCTION, FRAMING COMPLETED, IN ROUGHS. ESTIMATED COMPLETION FEBRUARY 2023. ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONSOpen concept ...
- 3 Beds
- 2 Baths
UNDER CONSTRUCTION, FRAMING COMPLETE. IN MECHANICAL ROUGHS. ESTIMATED COMPLETION MARCH, 2023.ALL PHOTOS ARE FROM SIMILIAR MODEL AND NOT REPRESENTATIVE OF SELECTIONS.If yo...
- 3 Beds
- 2 Baths
UNDER CONSTRUCTION, CURRENT STAGE, TRIM CARPENTRY. ESTIMATED COMPLETION JANUARY, 2023.Open concept ranch in desired Easton Park subdivision. Home features vaulted ceiling...
- 3 Beds
- 2 Baths
Gorgeous 6 bed, 4.5 bath 2-Story boasts over 5,600 square feet of living space in desirable Duneland Cove Subdivision. The marble entry draws you into the living room wit...
- 6 Beds
- 5 Baths
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
Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan Including a versatile flex room and an open concept layout featuring...
- 4 Beds
- 3 Baths
Make a splash this season! Buy your loved ones a home with a heated INDOOR POOL. Enjoy swimming year round including a diving board. This 1.5 story on a little piece of ...
- 4 Beds
- 5 Baths
MOTIVATED SELLER! Just shy of half an acre and recently built in 2015. This home offers over 2,700 sq. ft of living space, an attached 3 car garage with 11 foot ceilings,...
- 4 Beds
- 3 Baths
TAKE NOTICE! This is not your typical bilevel! Here we offer a 5-bed/3-bath grand home, with 3000 sq ft of finished living space, on a nearly-1/2-acre gorgeous wooded lot...
- 5 Beds
- 3 Baths
Retreat to your custom built one owner home and be dazzled by 3 floors of uninterrupted views of the protected Coffee Creek Conservancy. 3 bedrooms, 5.5 baths and 6134 f...
- 3 Beds
- 6 Baths
The Starling is a beautifully designed open floor plan for the modern family home. Enjoy plenty of openspace, custom kitchen, and outdoor living space opportunities with ...
- 3 Beds
- 3 Baths
Over 5000 finished square feet welcomes you to Tamarack! This home offers all the bells & whistles in this highly desirable neighborhood. A spacious porch welcome you to ...
- 5 Beds
- 5 Baths
Location! Location! Welcome home to this beautiful 5 bedroom , 4 bath Two-story located 1 mile from Lake Michigan, Indiana Dunes National Park, the South Shore station a...
- 5 Beds
- 4 Baths
Welcome Home to 365 Conestoga Drive. Two-story cedar-sided home on corner lot, tree-lined streets in coveted Olde Towne subdivision. Perfect for Young Professionals or t...
- 3 Beds
- 3 Baths
MOTIVATED SELLER offering $2500 towards closing costs. FIVE WOODED ACRES- A custom, 2-story brick home nestled in the woods of the Winderemere neighborhood in Chesterton....
- 4 Beds
- 4 Baths
Fantastic charm and character can be found in this Chesterton home. Featuring 4 bedrooms and 2.5 baths. Large kitchen with island is perfect for gatherings with eat in an...
- 4 Beds
- 3 Baths
This BRAND NEW, never-occupied duplex in the heart of Chesterton makes for a great residence or investment property! Newly-constructed in July, 2022, the twin units featu...
- 4 Beds
- 4 Baths
Make country lodge living YOURS this holiday season! This 4.46-acre retreat has it all from a grove of fruit trees to Smart Home technology. Each and every detail of this...
- 4 Beds
- 3 Baths
Beautiful rolling property in desireable Jackson Township suitable for development, horse farm, vineyard or your own private estate is waiting for you. Established trees ...
Beautiful Setting. Property borders 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
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
- 3 Baths
Don't miss this opportunity to own a BEAUTIFUL NEW 2 Story home in the St. AndrewsCommunity! The elegant 2002 Plan offers flex room on the main floor. The kitchen feature...
- 4 Beds
- 3 Baths
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
- 3 Baths
Now building in the Villages of Sand Creek Condos! This exciting new development is now ready for construction! Nestled in the picturesque wooded landscape, this commun...
- 3 Beds
- 3 Baths
Like New Ranch in Downtown Chesterton! This Lovely Ranch on a Full, Finished Basement has So Much to Offer! Built in 2012, Home Features a Spacious Entry at the Front of ...
- 4 Beds
- 3 Baths
Get your hands on the most ideal location in all of Chesterton. This building is full of history and charm right in the heart of downtown with frontage on Broadway and 2n...
Subject property is located on NE corner of Meridian and Indiana Toll Rd. Property has approximately 491' of frontage on Meridian then traveling nearly 1/2 mile East and ...
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 ...
No need to search any further, the new home you have been looking for is HERE! This extraordinary, Chesterton, 4 bed, 3 bath RANCH will surely take your breath away with ...
- 4 Beds
- 3 Baths
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...
Nothing But the Best in this fabulous 4 Bedroom 4 bathroom home located in an established beautiful neighborhood. This home offers updated hardwood floors throughout, an ...
- 4 Beds
- 4 Baths
This one acre lot is located just two miles from The Indiana Dunes State Park and Indiana Dunes National Park. Which had an estimated 3,177,234 visitors in 2021 according...
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. The ...
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
Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan Including a versatile flex room and an open concept layout featuring...
- 4 Beds
- 3 Baths
Come check out this BEAUTIFUL NEW 2 Story Home in the The Preserve Community! The desirable 2402 Plan Including a versatile flex room and an open concept layout featuring...
- 4 Beds
New construction ranch home with full unfinished basement just down the street from Chesterton High School in The Preserve. If you want quality construction, this is the ...
- 3 Beds
- 2 Baths
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
- 3 Baths
Updated . Information deemed reliable but not guaranteed.
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