Chesterton Real Estate

Chesterton Real Estate

Welcome to Chesterton, Indiana, a charming town nestled in the heart of Porter County. Known for its picturesque landscapes and vibrant community spirit, Chesterton is a delightful blend of small-town charm and modern convenience. With a population of around 13,000 residents, this welcoming community is perfectly situated just a short drive from the bustling city of Chicago, making it an ideal location for those seeking a peaceful retreat without sacrificing access to urban amenities.

One of the town's standout features is its proximity to the stunning Indiana Dunes National Park, where residents and visitors alike can enjoy miles of sandy beaches, scenic hiking trails, and breathtaking views of Lake Michigan. Chesterton also boasts a rich history, with a downtown area that showcases beautifully preserved architecture and a variety of local shops, restaurants, and cultural attractions. The Chesterton European Market, held every Saturday from May to October, is a must-visit, offering an array of fresh produce, artisanal goods, and handmade crafts that reflect the town's vibrant community spirit.

Families will appreciate the excellent schools and recreational facilities that Chesterton offers, including parks, sports leagues, and community events throughout the year. The town's friendly atmosphere and strong sense of community make it a wonderful place to call home.

Whether you're looking to settle down or simply explore, Chesterton, Indiana, is a hidden gem that promises a fulfilling lifestyle surrounded by natural beauty and a welcoming community. Discover the charm of Chesterton today!

Newest Listings in Chesterton

415 Sand Creek Drive N, Chesterton
$299,000
2 Beds ⋅ 3 Baths
Stunning, maintenance-free living awaits in this beautifully updated end-unit condo, ideally situated on a desirable corner lot! From the moment you step inside, you'll appreciate the impressive updates and inviting open layout. The spacious living room features a dramatic two-story tiled fireplace, rich hardwood flooring, and a sliding glass door leading to the back deck. The seamless flow into the dining area and kitchen makes this home ideal for both everyday living and entertaining. The completely renovated kitchen is sure to impress, offering abundant cabinetry, beautiful tiled backsplash, an extended island providing additional workspace and seating, and slate appliances. Adding to convenience, a main-level laundry room has been incorporated into the home and also serves as a stylishly updated half bath. Upstairs, retreat to the generously sized primary suite featuring hardwood flooring, a sleek, newly renovated bathroom, a custom closet organizer, and an extra-large walk-in closet. The second spacious bedroom offers its own private full bathroom and custom closet organizer, providing comfort and privacy for guests or family members. Additional highlights include an unfinished basement offering excellent storage or future finishing potential, along with an attached two-car garage. Beautifully updated, thoughtfully designed, and truly move-in ready. This exceptional condo offers the perfect combination of style, space, and maintenance-free convenience!

415 Sand Creek Drive N, Chesterton
2036 Texas Street, Chesterton
$284,900
2 Beds ⋅ 2 Baths
Welcome home to this beautifully remodeled, move-in-ready ranch-style townhome in desirable Chesterton. Featuring an expansive side lot and peaceful backyard pond views, this home offers a rare blend of generous outdoor space and low-maintenance one-level living. Step inside to discover soaring high ceilings, fresh neutral paint, and brand-new flooring and trim throughout an airy, open living and dining area. The bright, spacious eat-in kitchen provides a distinct and functional space for everyday dining, while skylights bathe the home in cheerful natural light. The primary bedroom suite serves as a private retreat, complete with a generous walk-in closet and a dedicated ensuite bath featuring its own sunlit skylight and walk-in shower. A comfortable second bedroom and an updated second full bath provide ample accommodations for guests or a home office. Practical conveniences abound with a dedicated laundry room and significant mechanical updates, including all-new plumbing fixtures and shutoff valves, a 7-year-old furnace, and a roof approximately 10 years old. Outside, unwind on the back patio while soaking in tranquil water views and the expansive feel of the adjoining lot. This turn-key gem perfectly marries tasteful modern updates with comfortable scenic living.

2036 Texas Street, Chesterton
2108 Tupelo Lane, Chesterton
$215,000
2 Beds ⋅ 2 Baths
EASY, MAINTENANCE FREE LIVING! This charming 2 bedroom, 2 bathroom ranch style townhouse offers the perfect combination of comfort and convenience! Step inside to find impressive, vaulted ceilings in the kitchen and dining area, creating and open and airy feel that flows seamlessly into the inviting living room. The spacious primary suite features its own private full bathroom. Enjoy peace of mind with a brand NEW roof (no assessment) , LOW taxes, AND and HOA that takes care of the rest. HOA fees cover all utilities except gas and electric, along with lawn care, snow removal, and exterior maintenance. Minutes to downtown Chesterton, parks, schools, restaurants, shopping and I-94. Whether you're looking to downsize or simply enjoy a low maintenance lifestyle, this home is a must see. Schedule your showing TODAY!

2108 Tupelo Lane, Chesterton
1764 Elgin Street, Chesterton
$225,000
3 Beds ⋅ 3 Baths
Fixer-upper on nearly 3 acres in Chesterton with Duneland Schools! This 3-bedroom, 2.5-bath brick and wood ranch offers 1,849 sq ft on the main level, a full unfinished basement, a 2-car attached garage, a family room with fireplace, main-floor laundry and a primary suite with private bath. Three parcels sold together give you room to spread out, build or invest. Needs a full rehab. Ideal for investors, contractors or a buyer ready to make it their own. Cash or rehab financing.

1764 Elgin Street, Chesterton
1040 Country Creek Lane, Chesterton
$995,000
4 Beds ⋅ 3 Baths
Custom 5,000 Sq Ft Country Lodge | 3.21 Acres | Creek, Fruit Trees & Pasture |No HOA | Duneland Schools Come home, relax, and enjoy every day. Designed by an architect and designer and brought to life by a custom builder, this country lodge is a one-of-a-kind retreat on 3.21 acres in Chesterton. Every detail of its 5,000 sq ft of smart-home living was meticulously chosen, with 3-4 bedrooms and 3 baths. A welcoming wrap-around porch and solid hickory front door set the tone. Inside, oversized kiln-dried logs, timber frame beams, and soaring ceilings create a warm, dramatic lodge feel, anchored by curated wood floors and a massive stone wood-burning fireplace made for cold-weather evenings. From morning coffee to sunset dinners, the 3-season porch is where you'll live. A second wood-burning fireplace, a BBQ grill with exhaust, make it the perfect spot to unwind or entertain, surrounded by mature trees and wildlife. Outside, true country living awaits. A 2-sided 16x18 equipment/ wood shed and a 16x18 Hay /equipment shed makes life a lot easier to store all you need. A meandering creek winds through the property, fruit trees add seasonal bounty, and a fenced pasture gives you room for animals, hobby farming, or wide-open space to roam. The walkout level has its own separate entrance, opening the door to related living for extended family or guests. An attached 24x26 flex space works as a workshop or an additional garage. There is no HOA, and all utilities are run underground for an uncluttered view of the landscape. Zoned for Duneland Schools. Enjoy country living without the isolation. You're about 7 minutes from downtown Chesterton's shops, restaurants, and seasonal European Market, and close to the beaches and trails of Indiana Dunes National Park, major highways, and the South Shore Railway. Downtown Chicago and Notre Dame are each about 60 minutes away. Schedule your private tour today!

1040 Country Creek Lane, Chesterton
256 E Burdick Place, Chesterton
$95,000
Bring your vision to life with this vacant lot in Burdick Place. Whether you're looking to build your dream home or invest in land for the future, this property offers an exciting opportunity to make your plans a reality. Enjoy the chance to create a home tailored to your style and needs in a desirable Chesterton location, conveniently close to local shopping, dining, parks, major highways, Southshore trains, Indiana Dunes, and area amenities.

256 E Burdick Place, Chesterton
253 E Burdick Road, Chesterton
$95,000
Bring your vision to life with this vacant lot in Burdick Place. Whether you're looking to build your dream home or invest in land for the future, this property offers an exciting opportunity to make your plans a reality. Enjoy the chance to create a home tailored to your style and needs in a desirable Chesterton location, conveniently close to local shopping, dining, parks, major highways, Southshore trains, Indiana Dunes, and area amenities. Don't miss this opportunity to secure your piece of land and start planning your future!

253 E Burdick Road, Chesterton
2524 Hilfiger Drive, Chesterton
$499,999
4 Beds ⋅ 4 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 spacious bedrooms, four bathrooms, and a well-appointed kitchen, this home seamlessly blends comfort, style, and functionality. The thoughtfully designed floor plan provides inviting spaces for both everyday living and entertaining, while the fully finished basement offers exceptional additional living space with endless possibilities. The Ensuite Primary bedroom offers a beverage center, built-in window seat and a HUGE walk in closet. Pride of ownership is evident throughout, making this a wonderful opportunity to own a truly special home in a sought-after location. The big ticket items; roof, HVAC and HWH have all been replaced over the last 5 years

2524 Hilfiger Drive, Chesterton
2227 W 1100 N, Chesterton
$899,900
6 Beds ⋅ 5 Baths
SIGNIFICANT PRICE IMPROVEMENT! Now offered substantially below appraised value, this stunning NEW CONSTRUCTION home presents an opportunity to own one of Chesterton's most impressive luxury residences. Overlooking Dogwood Park and situated on nearly half an acre, this extraordinary 6-bedroom, 4.5-bath home offers over 5,000 square feet of thoughtfully designed living space. Luxury upgrades and designer finishes are showcased throughout. The main-level primary suite provides a private retreat featuring a soaking tub, custom tiled shower, dual vanity, walk-in closet, and dedicated laundry area. The open-concept great room boasts soaring 11-foot ceilings and flows seamlessly to a spacious 20' x 16' covered patio, perfect for entertaining or relaxing. The chef-inspired kitchen is truly the heart of the home, highlighted by an oversized island, Cafe matte white appliances, double ovens, high-efficiency double-drawer dishwasher, instant hot water dispenser, beverage center, ceiling-height backsplash, and an expansive walk-in pantry with built-in desk area. The main floor also features a dramatic two-story foyer, sun-filled den, generous dining area, convenient half bath, and a unique dog-washing station just inside the garage entry. Upstairs, you'll find a second private ensuite complete with dual vanity and laundry area, two additional bedrooms, a full hall bath, and a comfortable loft overlooking the park. The finished lower level offers 9-foot ceilings, a large recreation space, two additional bedrooms, a full bath, dedicated laundry room, and abundant unfinished storage space. Additional highlights include custom window treatments throughout, a 3-car garage with heated and cooled dog room, security system, and immediate availability. Ideally located directly across from Dogwood Park and within walking distance of Chesterton High School. Close to the Indiana Dunes National Park, expressways and less than an hour from downtown Chicago. Award-winning Duneland Schools.

2227 W 1100 N, Chesterton
620 S 18th Street, Chesterton
$349,900
3 Beds ⋅ 2 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, situated on nearly a half-acre lot! The property offers a peaceful, country-like atmosphere while remaining just minutes from everything Chesterton has to offer. Inside, the stunning remodeled kitchen features custom maple cabinetry with soft-close doors and drawers, granite countertops, stainless steel appliances, updated lighting, and a spacious center island perfect for gathering with family and friends. Rich dark walnut hardwood floors flow throughout the main living areas. A charming fireplace highlights the dining room along with an abundance of natural light streaming in through the sliding glass door that opens onto the back covered porch. Step outside to enjoy the 12' x 20' concrete patio, perfect for entertaining or relaxing. A custom built shed featuring a SmartSide exterior, metal roof, and oversized double doors provide exceptional outdoor storage. Major improvements add both value and peace of mind, including a newer roof, insulated vinyl siding, soffits, gutters, windows, and sliding glass door. Both bathrooms have been tastefully updated, including a beautifully remodeled en suite bath with a tiled shower, updated lighting, and vanity. The partially finished basement expands the living space with recessed lighting, new windows, drywall, painted ceiling, and luxury vinyl plank flooring, making it ideal for a family room, home office, workout space, or recreation area. Conveniently located near award-winning Duneland Schools, Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, shopping, dining, and major highways for an easy Chicago commute, this exceptional property offers the best of both worlds: modern comfort with a spacious, country-feel setting in one of Northwest Indiana's most desirable communities!

620 S 18th Street, Chesterton
219 E 1200 N, Chesterton
$899,900
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 Sand Creek community, this rare offering presents nearly 8 acres of prime real estate with exceptional possibilities. This is a peninsula parcel surrounded by the golf course and pond. Whether you envision an expansive private estate surrounded by breathtaking golf course views or the opportunity to develop multiple residential homesites, this property offers remarkable flexibility and potential, making this a truly unique opportunity. Located in Chesterton, home to Indiana Dunes National Park and approximately 50 minutes from downtown Chicago, Sand Creek offers an exceptional setting with convenient access to amenities that will make this more than a place to life but the lifestyle you have been in search of.

219 E 1200 N, Chesterton
383 E 1050 N, Chesterton
$460,000
4 Beds ⋅ 3 Baths
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 space on a full acre of land. The brand new kitchen offers granite countertops with all new appliances and soft close cabinets. All 3 bathrooms have been completely renovated with new bathtub/showers, and vanities. The large living room offers a massive picture window for plenty of natural light. Off the kitchen is a full dining room with a picturesque 4 seasons room with plenty of windows to view the natural surroundings. New laminate flooring flows through the entire upstairs for a clean and elegant appearance. There are 3 bedrooms on the main level with the primary bedroom having an en suite bathroom to escape for some privacy. Downstairs you will find a massive rec room that could be easily transformed into a game room, large media area, or anything else your heart could desire. With a full bathroom and separate bedroom with egress window, the lower level could even be converted into related living space. There is also a large flex area in the lower level that could be finished as a home office, gym, or used for large storage. Parking will never be an issue with a heated attached garage and a 20x24 ft detached 2 car garage. All the big ticket items in this house have been updated, windows, roof, kitchen, bathrooms, water heater, flooring, and more are all new! Don't miss your opportunity to buy in the very desirable Jackson Township area, schedule your showing today!

383 E 1050 N, Chesterton
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