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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
Move-In Ready 3 Bed, 2 Bath Ranch | New 2026 Roof, Carpet & Paint | Rose Hill Estates | Just unpack and enjoy. This 3-bedroom, 2-bath ranch in Rose Hill Estates offers ...
- 3 Beds
- 2 Baths
Meticulously maintained and lovingly cared for by its original owner, this beautiful home is nestled in one of the area's most desirable neighborhoods. Offering four spac...
- 4 Beds
- 4 Baths
SIGNIFICANT PRICE IMPROVEMENT! Now offered substantially below appraised value, this stunning NEW CONSTRUCTION home presents an opportunity to own one of Chesterton's mos...
- 6 Beds
- 5 Baths
Beautifully updated 3 bed, 2 bath ranch in the heart of charming Chesterton! This move-in ready home offers the perfect blend of modern updates and timeless character, si...
- 3 Beds
- 2 Baths
Rare Opportunity to explore Development Potential or build a private estate on Just Under 8 Acres in Sand Creek. Situated along the golf course within the prestigious San...
Looking for a country home just minutes away from town? This maybe be the one for you! This fully remodeled home boasts 4 bedrooms, 3 bathrooms and 2500 sq ft of living s...
- 4 Beds
- 3 Baths
Timeless Elegance Meets Exceptional Craftsmanship! Welcome to this stunning 3-bedroom, 3.5-bath, two-story residence, where sophisticated design, beautiful architectural ...
- 3 Beds
- 4 Baths
LAST MAINTENANCE-FREE LOT IN EASTON PARK! Welcome to the popular Charlie floorplan, our LARGEST ranch design, offering spacious main-level living with thoughtful details ...
- 3 Beds
- 2 Baths
Tucked away in Chesterton is a unique property where natural beauty, history, and opportunity come together! Spanning 11.52 acres across two separate parcels, this proper...
- 4 Beds
- 2 Baths
Sellers offering a rate buy-down! Discover incredible land value and endless possibilities! Set far back from the road down a long driveway, this 3-bedroom, 2-bathroom b...
- 3 Beds
- 2 Baths
Welcome to the popular Melanie floor plan in Easton Park--FULLY LOADED with upgrades well beyond the standard features and MOVE IN READY! From custom cabinetry and elevat...
- 4 Beds
- 3 Baths
15.67 Private Acres | 4 Bed, 5 Bath All-Brick Estate | Pool, Pond & Sunroom | Duneland Schools *THE INTERIOR IS BEING PAINTED A BEAUTIFUL CREAMY WHITE* NEW PICS COMING! T...
- 4 Beds
- 5 Baths
Welcome to 1580 Eagle St in desirable Golfview Estates! This beautifully updated 4-bedroom, 3-full-bath home offers 2,364 sq ft of stylish and functional living space. Fr...
- 4 Beds
- 3 Baths
Rural residential property on 2.37 ACRES with POLE BARN! 4 bedroom/2 bath bi-level with attached garage. Spacious living room with fireplace, dining area & kitchen with ...
- 4 Beds
- 2 Baths
Chesterton ranch living at its best! This beautifully maintained 2006 ranch offers 1,680 sq ft, 3 bedrooms and 2 full baths, ideally located just minutes from Lake Michig...
- 3 Beds
- 2 Baths
Ranch living with room to spread out! This custom-built 4 bedroom, 3 bath home offers over 3,100 finished square feet, including an impressive finished daylight basement....
- 3 Beds
- 3 Baths
This stunning custom RANCH home sits on a private 1.18 wooded acre lot in the beautiful subdivision of Woodridge Hills featuring 3 bedrooms all with EN-SUITE BATHROOMS, 3...
- 3 Beds
- 4 Baths
Proposed Construction: We are excited to showcase THE ASPEN! This new construction, two-story craftsman style home encompasses four bedrooms, three bathrooms, and 1820 sq...
- 4 Beds
- 3 Baths
We are proud to introduce the Ruby model in The 1100 Woods. This grand Craftsman-style new-construction two-story home offers four bedrooms, three bathrooms, and over 2,1...
- 4 Beds
- 3 Baths
Welcome to this classic two-story home nestled in an established neighborhood surrounded by mature trees. This spacious home offers five bedrooms, beautiful hardwood fl...
- 5 Beds
- 2 Baths
Profitable duplex located less than 1 hour from Chicago, 10min to the South Shore Train, & 5min to I-94. Gross over 26,000 per year or live on one side & have your mortga...
- 4 Beds
- 4 Baths
Step into this nearly new Move-In ready 3- Bedroom, Maintenance-Free Ranch Duplex in Springdale! Open Concept layout with lots of natural light and beautiful Vinyl floor...
- 3 Beds
- 2 Baths
Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square fe...
- 5 Beds
- 5 Baths
Welcome to this Charming Townhome in the sought out Villages of Sand Creek! This home has great curb appeal with perennials galore and is a bird and butterfly paradise. ...
- 4 Beds
- 2 Baths
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...
SELLER OFFERING RATE BUY DOWN!! Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly ...
- 3 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
New construction home including irrigation, hydroseed and professional landscape package in the Preserve in the Duneland School Corp. This 2,735 square foot home makes an...
- 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
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
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...
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...
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
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
This is the opportunity you've been waiting for at 3624 Fairway Drive in Chesterton's Golfview Estates! Offering nearly 2,000 square feet, this 4-bedroom, 2-bath quad-lev...
- 4 Beds
- 2 Baths
Fresh updates, inviting spaces, and a fantastic Chesterton location make this ranch one you'll want to see! Featuring a newer roof , 3 bedrooms, 3 bathrooms, and an impre...
- 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. T...
- 3 Beds
- 3 Baths
Updated . Information deemed reliable but not guaranteed.
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