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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
Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, perfectly situated on an expansive .48-acre lot within the highly sought-after D...
- 3 Beds
- 2 Baths
Six-unit multifamily property in Chesterton, built in 1999 and masonry-framed over two stories: four two-bedroom, one-bath units and two one-bedroom, one-bath units acros...
Welcome to this 4 bedroom, 3 bath, 2-story home located in desirable Villages of Sand Creek. Main level offers a Formal Living Room as well as a Formal Dining, spacious ...
- 4 Beds
- 3 Baths
Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly 3,000 sq. ft. of finished living...
- 3 Beds
- 3 Baths
This sweet villa home has everything you need--without the worry of exterior maintenance! Conveniently located on the near east side of Chesterton, you'll enjoy easy acce...
- 3 Beds
- 2 Baths
Built in 2025 and practically brand new, this beautiful 4-bedroom, 2.5-bath home offers modern finishes, a functional layout, and plenty of room to grow! The open-concept...
- 4 Beds
- 3 Baths
Quality-built home that has been beautifully maintained and is truly move-in ready! This open-concept tri-level floor plan makes exceptional use of every square foot. The...
- 4 Beds
- 3 Baths
Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new...
- 4 Beds
- 3 Baths
Construction Complete - July! MOVE IN READY! The Preserve in the Duneland School Corp. This 2,735 square foot home makes an unforgettable impression. Off the foyer, a pri...
- 4 Beds
- 3 Baths
Stunning, updated 2-story home nestled on a private, wooded 0.56-acre in-town lot in Chesterton! A grand 2-story entry welcomes you with luxury vinyl plank flooring exten...
- 4 Beds
- 3 Baths
Welcome to 1909 Catkin Circle, an impressive fully updated Modern Farmhouse located in the highly desirable Tamarack Subdivision of Chesterton. Situated on nearly half an...
- 3 Beds
- 4 Baths
This meticulously updated four-bedroom, three-bathroom residence is situated in a prime Chesterton location. The interior features a thoughtfully redesigned kitchen equip...
- 4 Beds
- 3 Baths
Rarely available home in the sought after Tamarack subdivision. Elegant custom-built brick ranch with impressive curb appeal, lush landscaping, and a grand columned entr...
- 3 Beds
- 3 Baths
Bring your offer!!! Calling all buyers, contractors, and investors who see potential where others see projects. Some pictures are AI generated. See what the potential is ...
- 3 Beds
- 3 Baths
Welcome Home to the Ruby on Lot 12 in 1100 Woods! This new build is on one of the last tree lined lots left and features 4 generous sized bedrooms upstairs including a pr...
- 4 Beds
- 3 Baths
Welcome to one of out most desirable floorplans in 1100 Woods! This is PROPOSED CONSTRUCTION and we invite you to visit 2179 W 1100 which is the model home for this listi...
- 4 Beds
- 3 Baths
Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Du...
- 3 Beds
- 3 Baths
Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Du...
- 4 Beds
- 2 Baths
Discover the perfect blend of thoughtful design, modern comfort, and peaceful surroundings in this new construction home. Offering over 2,100 square feet in The Preserve,...
- 3 Beds
- 3 Baths
Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully designed living space in The Preserve. Situated on a premium homesite bordering protec...
- 3 Beds
- 2 Baths
Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully designed living space in The Preserve. Set on a premium homesite overlooking a wooded ...
- 3 Beds
- 2 Baths
Welcome to 1429 Calais Court, a beautifully maintained paired home nestled in the CHATEAUX DU CHAMBORDE area in the sought-after Sand Creek community of Chesterton. Offer...
- 3 Beds
- 4 Baths
Move-in ready and loaded with updates, this turn-key tri-level offers the space, style, and location today's buyers are searching for. Situated in the award-winning Dunel...
- 4 Beds
- 2 Baths
Here's your opportunity to enjoy homeownership while generating rental income! This well-maintained duplex offers an ideal owner-occupied investment, with the neighboring...
- 4 Beds
- 4 Baths
Imagine the possibilities! 52 acres ready for your dreams to be built here! There's even a 2 acre stocked pond! Approximately 880ft. of frontage on 1050N, and 2,500 ft. f...
Only 3 years young- this new construction build was completed by one of NWI's most prestigious builders in the desirable Preserve neighborhood known for its thick tree li...
- 4 Beds
- 3 Baths
Welcome to this 4-bedroom, 3-bathroom tri-level home located in the Porter Cove neighborhood of Chesterton. The upper level features three bedrooms, including the primary...
- 4 Beds
- 3 Baths
Introducing the Aspen on Lot 4 in 1100 Woods! PROPOSED CONSTRUCTION***** Located in the heart of Chesterton across from Dogwood Park and the Prairie Duneland Trail. The ...
- 4 Beds
- 3 Baths
Introducing The Chestnut - A Brand New Custom Ranch Floorplan on Lot 6! This thoughtfully designed ranch offers the perfect blend of style and function, featuring an open...
- 3 Beds
- 2 Baths
Welcome home to The Prescott in 1100 Woods! PROPOSED CONSTRUCTION on lot 16- one of the last tree lined lots of the subdivision. Large 2000 sqft ranch with unfinished lo...
- 3 Beds
- 2 Baths
Turnkey opportunity in the heart of downtown Chesterton -- this fully renovated 1,744 SF, two-story restaurant building is ready for its next concept. The property featur...
Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the he...
- 5 Beds
- 5 Baths
Nestled on an absolutely stunning wooded homesite, this brand new 3 bedroom home is sure to impress! Completion November-just in time for the holidays! Come and enjoy t...
- 3 Beds
- 3 Baths
Nestled on an absolutely stunning wooded homesite, this brand new 3 bedroom home is sure to impress! Completion November-just in time for the holidays! Come and enjoy t...
- 3 Beds
- 3 Baths
FULLY RENOVATED OFFICE/MEDICAL BUILDING CENTRALLY LOCATED, JUST ONE BLOCK OFF BROADWAY. Turn Key Property featuring 13 rooms/offices has been fully remodeled in past 3 ye...
FORE! Welcome to this exquisite Cape Cod residence in the prestigious Estates of Sand Creek subdivision. Enjoy breathtaking views of the 4th hole of the Marsh Course at S...
- 4 Beds
- 3 Baths
Excellent investment opportunity in the heart of Porter! Built in 2019, this well-maintained duplex features two spacious townhome-style units, each offering 3 bedrooms, ...
- 6 Beds
- 6 Baths
PROPOSED CONSTRUCTION-Welcome to the Sonoma in Easton Park! This stunning custom-built, 1.5-story home offers over 2,100 square feet of luxury living with 3 bedrooms, 2.5...
- 3 Beds
- 3 Baths
Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updated 4-bedroom, 3.5-bath home offers timeless design, modern improvements, and exc...
- 4 Beds
- 4 Baths
LUXURY MEETS NATURE in this exceptional 3 bedroom, 2 bath ranch, perfectly nestled on a .92 acre wooded lot! This custom built home offers an open-concept design with so...
- 3 Beds
- 2 Baths
First Time on the Market! Proudly offered by its original owner, this exceptional property presents a rare opportunity to own a private retreat nestled on 5 picturesque a...
- 4 Beds
- 4 Baths
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. Acro...
Within the gated Sand Creek community, this beautiful custom residence blends timeless architecture with thoughtfully curated designer updates, creating a home that is bo...
- 4 Beds
- 5 Baths
Welcome to 3624 Fairway Drive in Chesterton's desirable Golfview Estates! Offering nearly 2,000 square feet of living space, this 4-bedroom, 2-bath quad-level home provid...
- 4 Beds
- 2 Baths
Welcome to this beautifully maintained ranch home in the desirable community of Chesterton, now featuring a brand-new roof! This spacious residence offers 3 bedrooms, 3 b...
- 3 Beds
- 3 Baths
Welcome to 1622 Port Cove Dr in Porter, Indiana -- a charming 3-bedroom, 3-bathroom tri-level home offering approximately 1,742 square feet of comfortable living space, b...
- 3 Beds
- 3 Baths
Highly desirable Sand Creek property!!!! Presenting this custom built, 5 bedroom, 4.5 bath home. The list of updates to this property are endless!!! New gourmet appliance...
- 5 Beds
- 5 Baths
Light, bright and thoughtfully designed, this custom-built brick home offers over 4,000 square feet of exceptional living space in the heart of Chesterton. The inviting ...
- 4 Beds
- 5 Baths
Prime commercial opportunity with endless potential! Situated on just over an acre along a high-traffic roadway, this unique property features four buildings totaling nea...
This property offers the ideal combination of location, lot, and lifestyle. Located in Duneland Cove, this nearly 3,000-square-foot home features 3 bedrooms, 3 bathrooms,...
- 3 Beds
- 3 Baths
Updated . Information deemed reliable but not guaranteed.
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