Acreage in Liberty Township! Beautiful 4.12 Acre Lot in the sought out Duneland School District with just a 3 minute drive to Chestertion High School & 5 minutes to downtown Chesterton. No HOA, natural gas & electric have already been run to the property, soil borings have been completed, all other permits needed.

1065 N 50 W, Chesterton

Listing courtesy of Marina Klein from Blackrock Real Estate Services.

$559,900

4 Beds ⋅ 3 Baths ⋅ 842981 MLS ⋅ 1,820 SqFt. ⋅ Madison Young

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 Aspen model is ideal for those looking for a primary ensuite on main level with walk in closet, a large kitchen island for extra seating to gather, and plenty of storage. Kitchen over looks your great room and dining for an open concept.

2350 Pradera Trail, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$519,900

3 Beds ⋅ 2 Baths ⋅ 842980 MLS ⋅ 1,800 SqFt. ⋅ Madison Young

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-concept layout with a spacious great room with optional fireplace, dining area, and kitchen complete with quartz countertops and upgrade options available. The primary ensuite provides a private retreat, while generous guest bedrooms offer comfort and versatility. Enjoy the flexibility of a partial unfinished basement--ideal for future living space or ample storage. Located in the heart of Chesterton, this home is being built by one of the area's most highly regarded custom builders. Now is the perfect opportunity to personalize your selections and bring your dream home to life!

2420 Pradera Trail, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$569,900

3 Beds ⋅ 2 Baths ⋅ 842978 MLS ⋅ 2,000 SqFt. ⋅ Madison Young

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 lookout basement with 3 car garage is the perfect blend of main level living with room to expand to almost 4000 sqft when finishing the basement. The view from your living room and deck is only of trees giving you a beautiful feeling of seclusion while being close to everything Chesterton has to offer! Across the street is the popular Dogwood Park and Prairie Duneland trail. If you are a waking, running or biking enthusiast this is the perfect location for you! Inside you will find a versatile floorplan that you can customize and select all finishes. Primary bedroom features spa like bathroom and walk in closet. 2nd and 3rd bedrooms are good sized and there is a bonus flex room perfect for an office or possible 4th bedrooms.

2431 Pradera Trail, Chesterton

Listing courtesy of Madison Young from Brokerworks Group.

$475,000

842974 MLS ⋅ 1,744 SqFt. ⋅ Nicholas Sommer

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 features a full commercial kitchen with walk-in cooler, two levels of indoor dining, and a bathroom on each floor, plus a spacious courtyard and deck offering additional outdoor dining. Extensive top-to-bottom renovations include new HVAC, restored hardwood floors, new windows, gutters, soffit, fascia, siding, shutters, corbels, bathrooms, ceiling tiles, and lighting fixtures -- delivering a move-in-ready space with modern systems and timeless character. Situated in a highly walkable downtown corridor surrounded by shops and restaurants, the location offers excellent visibility and foot traffic, with the added draw of close proximity to Indiana Dunes National Park and convenient access to major highways. Call today to schedule your property tour.

321 Broadway Avenue, Chesterton

Listing courtesy of Nicholas Sommer from Century 21 Alliance Group.

$269,900

2 Beds ⋅ 1 Baths ⋅ 842889 MLS ⋅ 1,204 SqFt. ⋅ Diane Cline

515 S Park Drive, Chesterton

Listing courtesy of Diane Cline from McColly Real Estate.

$97,500

842783 MLS ⋅ Matt Evans

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! Lot 21 in Phase VI-A backs directly to the golf course, on Marsh Course #4, offering beautiful views and a picturesque setting for your future custom home. Sand Creek Country Club features an outstanding array of membership amenities, including championship golf, swimming, tennis, fitness facilities, dining, social events, and year round recreational programs. Ideally located just minutes from the beautiful shores of Lake Michigan, this property also provides convenient access to the South Shore Line for an easy commute to downtown Chicago, approximately one hour away. Located within the highly regarded Duneland School Corporation, this homesite offers an outstanding combination of location, lifestyle, and accessibility. An adjoining golf course lot is also available for purchase under a separate MLS listing, providing the opportunity to expand your homesite or enhance your privacy. Buyer to verify lot dimensions, utilities, HOA information, building requirements, membership availability, and all intended uses.

1160 Monterey Drive, Chesterton

Listing courtesy of Matt Evans from RE/MAX Lifestyles.

$97,500

842782 MLS ⋅ Matt Evans

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! Lot 20 in Phase VI backs directly to the golf course, on Marsh Course #4, offering beautiful and a picturesque setting for your future custom home. Sand Creek Country Club features an outstanding array of membership amenities, including championship golf, swimming, tennis, fitness facilities, dining, social events, and year round recreational programs. Ideally located just minutes from the beautiful shores of Lake Michigan, this property also provides convenient access to the South Shore Line for an easy commute to downtown Chicago, approximately one hour away. Located within the highly regarded Duneland School Corporation, this homesite offers an outstanding combination of location, lifestyle, and accessibility. An adjoining golf course lot is also available for purchase under a separate MLS listing, providing the opportunity to expand your homesite or enhance your privacy. Buyer to verify lot dimensions, utilities, HOA information, building requirements, membership availability, and all intended uses.

1180 Monterey Drive, Chesterton

Listing courtesy of Matt Evans from RE/MAX Lifestyles.

$875,000

5 Beds ⋅ 5 Baths ⋅ 842756 MLS ⋅ 6,360 SqFt. ⋅ Alexis Metcalf

Step into a timeless masterpiece where history, craftsmanship, and tradition come together in one of Chesterton's most iconic neighborhoods. Proudly positioned at the heart of this cherished community on ONE ACRE this extraordinary three-story residence has been lovingly preserved while offering the space and amenities desired for modern living. Rich in architectural character, the home showcases stunning original details including exquisite tilework, handcrafted wood paneling, custom cabinetry, and elegant millwork that speak to a bygone era of unparalleled craftsmanship. Grand entertaining spaces include a stately formal dining room, a classic butler's pantry, and beautifully proportioned living areas designed for memorable gatherings. Offering 5 spacious bedrooms and 5 baths, the home seamlessly blends historic elegance with exceptional comfort. A rare indoor pool provides year-round enjoyment, while the enchanting English garden creates a private sanctuary of manicured beauty and quiet reflection. More than a home, this is a time honored property--a place where generations have celebrated holidays, hosted gatherings, and created lasting memories. Opportunities to own a residence of this significance are exceptionally rare. For those who appreciate history, timeless architecture, and the privilege of becoming the next steward of an extraordinary legacy, this is truly a once-in-a-lifetime offering.

229 E Morgan Avenue, Chesterton

Listing courtesy of Alexis Metcalf from Seramur Properties, LLC.

$449,900

3 Beds ⋅ 3 Baths ⋅ 842666 MLS ⋅ 1,857 SqFt. ⋅ The Villages BLDG. ⋅ Michelle Renninger

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 the maintenance-free lifestyle, where all of your snow removal and landscaping is taken care of for you. Upon entrance you'll find a spacious mudroom with plenty of room for storage, and a convenient desk space for a home office. On the main floor you'll find an abundance of soft-close cabinetry, walk in pantry, and great island with seating. The living room boasts open space to the dining area and a fireplace as the focal point of the room. Upstairs offers a master suite with private bath and walk in closet, 2 additional bedrooms, full bath, and laundry room. Features such as a fully finished garage, custom lighting, tankless water heater, whole house humidifier, and more ensure this home is a pleasure for years to come. All of this located just minutes from the Dunes Lakeshore, South Shore commuter train station, commuter expressways, and more! Schedule your showing today! *Photos are of a recently complete home with a similar floor plan. Photos are representative.

1602 Melanie Lane, Chesterton

Listing courtesy of Michelle Renninger from Brokerworks Group.

$449,900

3 Beds ⋅ 3 Baths ⋅ 842665 MLS ⋅ 1,857 SqFt. ⋅ The Villages BLDG. ⋅ Michelle Renninger

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 the maintenance-free lifestyle, where all of your snow removal and landscaping is taken care of for you. Upon entrance you'll find a spacious mudroom with plenty of room for storage, and a convenient desk space for a home office. On the main floor you'll find an abundance of soft-close cabinetry, walk in pantry, and great island with seating. The living room boasts open space to the dining area and a fireplace as the focal point of the room. Upstairs offers a master suite with private bath and walk in closet, 2 additional bedrooms, full bath, and laundry room. Features such as a fully finished garage, custom lighting, tankless water heater, whole house humidifier, and more ensure this home is a pleasure for years to come. All of this located just minutes from the Dunes Lakeshore, South Shore commuter train station, commuter expressways, and more! Schedule your showing today! *Photos are of a recently complete home with a similar floor plan. Photos are representative.

1600 Melanie Lane, Chesterton

Listing courtesy of Michelle Renninger from Brokerworks Group.

$799,000

842493 MLS ⋅ 3,172 SqFt. ⋅ Terry McCaleb

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 years: New Flooring, Lighting, and Paint throughout. New Sinks/Vanities in each room. Newer Roof. Currently used as a medical facility, could easily be converted to traditional office spaces. Large Reception Desk and Lobby. Large Windows in rooms. Generac whole-building generator. 20 Parking spaces. Storage Shed stays, washer and dryer stay. 2 Bathrooms + shower room that could be a set up as a locker room.

407 W Indiana Avenue, Chesterton

Listing courtesy of Terry McCaleb from Brokerworks Group.

Homes for Sale with a Basement in Chesterton, IN

All Homes for Sale with a Basement in Chesterton, IN