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$220,000
837824 MLS ⋅ Stefanie Neal
Sold before market.

1939 Chamborde Lane, Chesterton

Listing courtesy of Stefanie Neal from BHHS Indiana Realty.

Selling Office: BHHS Indiana Realty.

$209,000
3 Beds ⋅ 1 Baths ⋅ 830172 MLS ⋅ 1,433 SqFt. ⋅ Charles Vanderstelt
Move right in and enjoy easy, everyday living in this spacious three-bedroom ranch in Chesterton. Inside, a bright and welcoming layout features a large living room and an oversized kitchen with a dishwasher and plenty of room to cook, gather, and entertain. All three bedrooms offer comfortable proportions, including a generously sized primary suite measuring an impressive 19x11. A versatile flex room adds even more value, perfect for a home office, den, or additional living space. Ideally located on the north side of Chesterton just off Woodlawn Ave, this home delivers outstanding convenience--less than six minutes to the South Shore Line Duneland Station, Indiana Dunes National Park, and I-94, with shopping, dining, banking, and daily essentials close by. Situated in the highly regarded Duneland School District, with schools including Brummitt Elementary, Westchester Intermediate/Middle, and Chesterton High School. Conventional, FHA, and VA financing are all welcome, making this an accessible opportunity in a prime location. Don't miss your chance to see 319 Michigami Trail--affordable, well-located, and ready to call home.

319 Michigami Trail, Chesterton

Listing courtesy of Charles Vanderstelt from Listing Leaders.

Selling Office: Realty Executives Premier.

$203,000
2 Beds ⋅ 1 Baths ⋅ 837609 MLS ⋅ 800 SqFt. ⋅ Jessica Cardin
Ranch on a basement! This home would be an ideal home if you are looking for space on a budget. 2 large bedrooms and an updated full bathroom. Hardwood floors throughout. Full basement is a bonus. Ideal location- close to highway, shopping, restaurants.

1608 W Porter Avenue, Chesterton

Listing courtesy of Jessica Cardin from Realty Executives Premier.

Selling Office: Prestige Midwest Realty, LLC.

$200,000
3 Beds ⋅ 1 Baths ⋅ 840551 MLS ⋅ 1,109 SqFt. ⋅ Tiffany Dowling
OH MY GOODNESS, THIS ONE HAS IT ALL!!! You know what they say: LOCATION, LOCATION, LOCATION! This charming three-bedroom ranch style home is nestled in the heart of beautiful Chesterton, Indiana. Just blocks from the historic and quaint downtown district, steps from an incredibly expansive park(with a splash pad), and only a short drive- 8 minutes to the beaches of Lake Michigan... lake life awaits! Incredible curb appeal greets you upon arrival, complete with a newer roof and gorgeous mature trees. The spacious living room showcases original hardwood floors that flow throughout the living room and bedrooms, along with fresh, modern paint colors. The eat-in kitchen offers abundant cabinet and counter space and opens seamlessly to the bonus four-seasons room, which also serves as the perfect formal dining area. Two main-floor bedrooms are conveniently located adjacent to the full bathroom. The full basement features a finished third bedroom with a closet, flexible living space, and a laundry room. The detached garage provides excellent storage and, with a little TLC, could become the ultimate garage, workshop, or man cave. Love to entertain? This home checks all the boxes with a generously sized backyard that's perfect for gatherings with family and friends. Whether you're just starting out, looking to downsize, or searching for your next investment property, THIS IS IT!!! Enjoy competitive Indiana taxes, an easy commute to Chicago, and close proximity to the beautiful shores of Lake Michigan. WELCOME HOME!!!

112 Chesterton Boulevard, Chesterton

Listing courtesy of Tiffany Dowling from Keller Williams Preferred Real.

Selling Office: White Hat Realty Group, LLC.

$189,000
814957 MLS ⋅ Stefanie Neal
LOT 10 in the newly developed Chamborde Lane in the gated community Sand Creek! This beautiful lot features water in the backyard with a beautiful fountain feature! 10 Lots available. Bring your own builder! Located just an hour from downtown Chicago, Chesterton offers easy access to major highways and train lines, all within an award-winning school district.

1930 Chamborde Ln Lane, Chesterton

Listing courtesy of Stefanie Neal from BHHS Indiana Realty.

Selling Office: BHHS Indiana Realty.

$178,000
2 Beds ⋅ 1 Baths ⋅ 841368 MLS ⋅ 725 SqFt. ⋅ Beth Janes
Charming, move-in ready ranch just a short walk to vibrant downtown Chesterton and the popular European Market. This beautifully maintained home offers low-maintenance living with numerous recent updates including roof, siding, chimney, sewer line, tankless water heater, and boiler. Enjoy a fenced backyard, oversized two-car garage, unfinished basement for storage, and inviting curb appeal. Whether you're a first-time buyer, downsizing, or looking for an investment property, this home offers an outstanding opportunity to enjoy one of Northwest Indiana's most desirable communities. Close to major highways, medical facilities, train station, beaches, dunes, and less than an hour to Chicago. Make your request to see this home today!

608 W Indiana Avenue, Chesterton

Listing courtesy of Beth Janes from Trueblood Real Estate, LLC.

Selling Office: Non-Member MLS Office.

$175,500
3 Beds ⋅ 2 Baths ⋅ 837561 MLS ⋅ 1,338 SqFt. ⋅ Westchester Village BLDG. ⋅ Alisha Fowler
Completely remodeled 3-bedroom, 2-bath condo in the heart of Chesterton--offering modern finishes, a functional layout, and true move-in ready convenience. MAINTENNACE FREE- lawn care, snow removal, trash, water, and all exterior maintenance covered. Single car enclosed garage! Located in a highly rated school district with easy access to major expressways and just minutes from the Indiana Dunes National Park. All of this for this list price is an exceptional opportunity for maintenance-free living in a prime location.

2128 Dogwood Lane, Chesterton

Listing courtesy of Alisha Fowler from Seramur Properties, LLC.

Selling Office: Real Broker, LLC.

$175,000
3 Beds ⋅ 1 Baths ⋅ 841451 MLS ⋅ 1,804 SqFt. ⋅ Debra Lightfoot
Welcome to this charming 1 1/2 story, 3 bedroom home ideally located in the heart of downtown Chesterton! Situated on a spacious .36 acre lot, this property offers an excellent location. The inviting great room features a vaulted ceiling, cozy, corner gas fireplace and sliding doors that lead out to the 24 x 8 deck overlooking the landscaped yard, which is filled with colorful perennial gardens that were planted with love and provide beautiful blooms throughout the seasons. Main floor also features a living/dining room, kitchen, 2 bedrooms and an updated bath with ceramic walk-in shower. The upper level features the 3rd bedroom. There is an attached garage, an additional detached garage, shed and extra parking, providing ample room for vehicles, hobbies or extra storage. Enjoy everything Chesterton has to offer just minutes from your doorstep, including restaurants, a winery and brewery, the seasonal European Market and a Farmer's Market, boutique and antique shopping, Lake Michigan beaches and recreational areas and year round community events. Bring your decorating ideas, this home has great bones and is ready for your personal updates and finishing touches. Don't miss this opportunity to own a home in one of Northwest Indiana's most desirable communities!

118 S 13th Street, Chesterton

Listing courtesy of Debra Lightfoot from McColly Real Estate.

Selling Office: McColly Real Estate.

$170,000
2 Beds ⋅ 1 Baths ⋅ 838693 MLS ⋅ 962 SqFt. ⋅ Westchester Village Cape Cod Cmnty BLDG. ⋅ Jacquelyn Brubaker
MOTIVATED SELLER!! Welcome to this charming 2-bedroom, 1-bath MAIN-level condo in the heart of Chesterton! Situated on a desirable corner unit, this home offers extra privacy and maintenance-free living -- say goodbye to lawn care and snow removal. Step inside and you'll love the bright and open feel, with newer LVP flooring flowing throughout. The kitchen is stocked with plenty of cabinet space, an eat in dinning room, and all appliances stay for your convenience. The spacious living room opens to a private paved patio, perfect for relaxing outdoors, while the primary bedroom also features its own sliding door to a second patio retreat. This condo is filled with natural light and cheerful charm. Enjoy the added bonus of a 1-car attached garage and a location right along the walking trail, making it easy to get outside and stay active. Centrally located near schools, parks, and downtown Chesterton, this home is the perfect blend of comfort and convenience.

2111 Tupelo Lane, Chesterton

Listing courtesy of Jacquelyn Brubaker from Coldwell Banker Real Estate Gr.

Selling Office: Listing Leaders Northwest.

$170,000
3 Beds ⋅ 2 Baths ⋅ 832457 MLS ⋅ 1,318 SqFt. ⋅ Westchester Village BLDG. ⋅ Karen Maynard
Eighth Wonder of the World!! C A R E F R E E L I V I N G!! Cute'n Cozy! Charming convenient maintenance free condo living just minutes from Downtown Chesterton and the magnificent INDIANA DUNES NATIONAL PARK! This main floor condo has a primary suite with private bath and TWO additional bedrooms (total 3 bedrooms) and bath. Lovely living area with slider out to peaceful deck area. NO STAIRS! Main floor laundry! 1 car garage! New carpet - new sliders - freshly painted - new ceiling fans - new furnace & new roof! Carefree, Convenient and Cost Effective! Enjoy two tennis courts, pond, walking paths and new Pickleball court going in this year! LIVABLE, LOVABLE & BEST OF ALL AVAILABLE! Relax and Enjoy Now!

2114 Tupelo Lane, Chesterton

Listing courtesy of Karen Maynard from McColly Real Estate.

Selling Office: Listing Leaders.

$168,000
2 Beds ⋅ 1 Baths ⋅ 830340 MLS ⋅ 1,228 SqFt. ⋅ Westchester Village Cape Cod Cmty BLDG. ⋅ Nikola Trajceski
Move-in ready, maintenance-free main-floor condo with a 1-car garage! A bright, open-concept living area features a cozy gas fireplace, and two new sliding doors to a private patio & your new backyard. The updated kitchen offers a brand-new quartz countertop, deep sink, pantry, and abundant cabinetry. Down the hall are two generous bedrooms, including a primary bedroom with a walk-in closet, an updated bath, and convenient in-unit laundry. Enjoy peace of mind with a brand-new A/C. HOA covers all utilities except gas and electric, plus lawn care, snow removal, and exterior maintenance. Minutes to downtown Chesterton, parks, schools, restaurants, shopping, and I-94 - this home blends comfort, convenience, and low-maintenance living. Schedule your showing TODAY!

2121 Tupelo Lane, Chesterton

Listing courtesy of Nikola Trajceski from Listing Leaders.

Selling Office: Brokerworks Group.

$162,000
3 Beds ⋅ 2 Baths ⋅ 838950 MLS ⋅ 1,447 SqFt. ⋅ Westchester Vlg Cape Cod Commu BLDG. ⋅ Karen Maynard
TOWNHOUSE LIVING AT ITS FINEST - Three bedrooms 2 1/2 baths & 1 car attached garage! Main floor laundry. Private community has so much to offer - tennis courts, pool, pond with Fountain and wooded walking trail - RELAX and enjoy maintenance free Living and let association take care of snow removal and lawn maintenance, Water, garbage, and exterior insurance. Minutes to downtown Chesterton, Parks, schools, restaurants, shopping and close to Dunes and I 94. This is a Win win and you can't beat the price!

2105 Tupelo Lane, Chesterton

Listing courtesy of Karen Maynard from McColly Real Estate.

Selling Office: McColly Real Estate.

$158,000
2 Beds ⋅ 1 Baths ⋅ 834405 MLS ⋅ 1,227 SqFt. ⋅ Westchester Village Home BLDG. ⋅ Brent Wright
HOME SWEET HOME! This beautifully maintained 2 Bed, 1 Bath Maintenance-Free Condo with a 1-Car Garage and POND VIEWS is a MUST SEE! From the moment you walk in, you'll appreciate the natural light and the spacious living room featuring peaceful pond views. The kitchen offers ample cabinet and counter space, a convenient breakfast bar, and stainless-steel appliances (newer refrigerator & garbage disposal) that stay -- making it move-in ready from day one. The formal dining area is perfect for entertaining and leads to your private balcony overlooking the pond -- an ideal spot for morning coffee or relaxing evenings. The spacious primary bedroom includes a walk-in closet and direct access to the full bath for added convenience. You'll also love the dedicated laundry room (newer dryer) with additional storage -- a feature not always found in condo living. Freshly painted and well cared for, this home also offers peace of mind with a newer roof. The HOA covers snow removal, lawn care, exterior maintenance, water, sewer, trash, and more -- giving you true low-maintenance living. PRICED TO SELL -- Schedule your showing today before this one is gone!

2023 Hawthorne Lane, Chesterton

Listing courtesy of Brent Wright from McColly Real Estate.

Selling Office: @properties/Christie's Intl RE.

$150,000
2 Beds ⋅ 1 Baths ⋅ 836723 MLS ⋅ 984 SqFt. ⋅ Jodi Gheaja
SOLD BEFORE PRINT

124 Grant Avenue, Chesterton

Listing courtesy of Jodi Gheaja from Realty Executives Premier.

Selling Office: Realty Executives Premier.

$135,000
3 Beds ⋅ 3 Baths ⋅ 833721 MLS ⋅ 1,480 SqFt. ⋅ Village Community Inc BLDG. ⋅ Olga Petryszyn
CAREFREE CONDO. More to life than weeding lawns! Enjoy tennis, a pool and a beautiful park nearby. This is a spacious unit with 3 bedrooms and 2.5 baths. The woodburning fireplace is wonderful on cold nights. The roof has been replaced 3 years ago. One car attached garage and extra street parking. Your association fees included outside maintenance, snow removal, water, sewer, trash and street lighting. This 2 story condo needs some TLC and is priced for quick sale. Wonderful Chesterton location.

2105 Dogwood Lane, Chesterton

Listing courtesy of Olga Petryszyn from McColly Real Estate.

Selling Office: Listing Leaders.

$125,000
3 Beds ⋅ 1 Baths ⋅ 842161 MLS ⋅ 864 SqFt. ⋅ Ruza Jevtic
Attention Investors Great Opportunity! This charming 3-bedroom, 1-bath ranch offers comfortable living in a fantastic Chesterton location. The home features a spacious 2.5-car detached garage, additional carport, and a new shed for extra storage. Conveniently located near schools, parks, downtown Chesterton, the Indiana Dunes, and major highways, you'll enjoy easy access to shopping, dining, recreation, and commuting. A wonderful opportunity to own a home in a highly desirable location!

415 S 16th Street, Chesterton

Listing courtesy of Ruza Jevtic from Realty Executives Premier.

Selling Office: Realty Executives Premier.

$125,000
835531 MLS ⋅ Tonia Dragon
Discover the possibilities with this beautiful 3.38-acre parcel. Located in the highly desirable Jackson Township and within the award-winning Duneland School Corporation, this property offers the perfect opportunity to build the home of your dreams. Enjoy the space, privacy, and peaceful surroundings while still being just minutes from major highways and the amenities of Chesterton. With endless possibilities for development, this property provides the ideal balance of rural charm and convenient access to town. An identical 3.38-acre parcel next door is also available, offering even more potential for those seeking additional land.

0-1 E 1050 N, Chesterton

Listing courtesy of Tonia Dragon from Better Homes and Gardens Real.

Selling Office: Better Homes and Gardens Real.

$125,000
835525 MLS ⋅ Tonia Dragon
Discover the possibilities with this beautiful 3.38-acre parcel. Located in the highly desirable Jackson Township and within the award-winning Duneland School Corporation, this property offers the perfect opportunity to build the home of your dreams. Enjoy the space, privacy, and peaceful surroundings while still being just minutes from major highways and the amenities of Chesterton. With endless possibilities for development, this property provides the ideal balance of rural charm and convenient access to town. An identical 3.38-acre parcel next door is also available, offering even more potential for those seeking additional land.

0-2 E 1050 N, Chesterton

Listing courtesy of Tonia Dragon from Better Homes and Gardens Real.

Selling Office: Better Homes and Gardens Real.

$100,000
843167 MLS ⋅ Lisa Gaff
Imagine your dream home nestled among the trees on this beautiful 1.36-acre corner lot at 369 Ridgeview Drive. Located in Woodridge Hills, a private Jackson Township community known for its spacious wooded homesites and impressive custom residences, this property offers the rare opportunity to create a home designed entirely around your lifestyle. The generous corner setting provides flexibility for a striking home design, welcoming driveway and outdoor living spaces while preserving the natural beauty and privacy of the surrounding woods. Building plans are subject to applicable covenants and approvals. Enjoy a peaceful, tucked-away setting without giving up convenience. Downtown Chesterton's locally owned restaurants, boutiques, art scene, festivals and popular European Market are just minutes away. Spend weekends hiking, biking and enjoying Lake Michigan's shoreline at Indiana Dunes National Park, which protects 15 miles of beaches along the southern shore of Lake Michigan. For commuters or Chicago day trips, nearby Dune Park Station provides access to the South Shore Line, connecting Northwest Indiana directly with Millennium Station in downtown Chicago. With convenient access to Route 49, major expressways, Chesterton and Valparaiso, this location brings together privacy, natural beauty and everyday convenience. Bring your vision and create something truly remarkable at 369 Ridgeview Drive.

369 Ridgeview Drive, Chesterton

Listing courtesy of Lisa Gaff from White Hat Realty Group, LLC.

Selling Office: White Hat Realty Group, LLC.

$94,000
3 Beds ⋅ 1 Baths ⋅ 843966 MLS ⋅ 1,017 SqFt. ⋅ Charles Vanderstelt
Calling all real estate investors looking for their next opportunity in Chesterton! Whether your strategy is to renovate and resell or improve and hold as a long-term rental, this property offers plenty of potential. The home features three bedrooms, one full bathroom, an oversized living room, and a practical layout with bedrooms spaced throughout the home. Adding to the opportunity is the additional parcel immediately to the north, which is included with the sale and brings the combined lot size to more than 9,300 square feet. The extra outdoor space provides additional breathing room and flexibility that can be difficult to find at this price point. Location is another important advantage. Situated in west central Chesterton, the property offers convenient access to employment, schools, shopping, restaurants, and the everyday necessities residents depend on. And unlike some properties in the area, you won't have train tracks or an interstate sitting directly in your backyard. For an investor, the possibilities are straightforward: renovate the home and bring it back to market, or make the necessary improvements and add another Chesterton property to your rental portfolio. The three-bedroom configuration, generous living space, additional parcel, and convenient location provide a solid foundation for either strategy. Bring your ideas, your contractor, and your numbers. If you've been searching for a Chesterton investment property where you can create value through renovation, this one deserves a closer look.

124 S Jackson Boulevard, Chesterton

Listing courtesy of Charles Vanderstelt from Listing Leaders.

Selling Office: Non Member.

$90,000
2 Beds ⋅ 2 Baths ⋅ 838453 MLS ⋅ 1,587 SqFt. ⋅ Georgeann Weisman
1057 Woodlawn presents a great opportunity for investors, rehabbers, or buyers looking to add value. This 2-bedroom, 2-bath home features a detached 2-car garage and a functional layout with plenty of potential. Property is in need of repairs and updates, including foundation and waterline repairs, and is being sold as-is. With the right vision and renovation work, this property could be transformed into a solid investment or future residence. Convenient location close to local amenities, schools, and major roadways.

1057 Woodlawn Avenue, Chesterton

Listing courtesy of Georgeann Weisman from Brokerworks Group.

Selling Office: CHERYL Real Estate Services, L.

$90,000
810942 MLS ⋅ Patricia Raffin
Create the possible! These in town, Duneland Cove lots, have municipal water & sewer, gas and electric available. Convenient easy transit to highways, rails, shopping, schools, parks, playgrounds and within minutes to our beautiful Lake Michigan shoreline beaches, parks and trails. All permits required, No HOA, covenants and restrictions apply.

Lot 132 Michael Drive, Chesterton

Listing courtesy of Patricia Raffin from McColly Real Estate.

Selling Office: McColly Real Estate.

$86,500
3 Beds ⋅ 1 Baths ⋅ 841500 MLS ⋅ 1,688 SqFt. ⋅ Susan Beyler
Best and final due by 7/6 at 5pm. Calling all investors, flippers, or handy buyers! This is a great opportunity with excellent potential for rental, flip, or to renovate your own home in a desirable location. Home is cleaned out and ready for rehab.

302 Indiana Street, Chesterton

Listing courtesy of Susan Beyler from Harbor & Lake Real Estate, LLC.

Selling Office: @properties/Christie's Intl RE.

$50,000
833901 MLS ⋅ Paul Boyter
Phase 3 is now open and ready for building. Lot 64 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

1002 Preserve Lane, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

Selling Office: McColly Real Estate.

$50,000
833899 MLS ⋅ Paul Boyter
Phase 3 is now open and ready for building. Lot 92 in one of Chesterton's newest neighborhoods. Conveniently located near the Chesterton High School and close to the South Shore Train, Indiana Toll Road, and Lake Michigan Indiana Dunes State Park. Drive out to see Where Nature is Your Neighbor.

1003 Preserve Lane, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

Selling Office: McColly Real Estate.

$49,000
839648 MLS ⋅ Valerie Huizar
Has it always been your dream to build? Look no further. Exceptional lot in a quiet cul-de-sac offering privacy and a peaceful setting in The Preserves subdivision, Chesterton, IN. This beautiful parcel sits in a desirable community known for its wooded lots. Conveniently located just minutes from Chesterton High School and with easy access to the South Shore Line and the Indiana Toll Road, commuting and travel are simple. Enjoy weekend escapes to nearby Lake Michigan and Indiana Dunes State Park for beaches, trails and outdoor recreation. Close to shopping, dining and local amenities while still offering a serene, neighborhood feel.

45 Karner Blue Court, Chesterton

Listing courtesy of Valerie Huizar from Realty Executives Premier.

Selling Office: Realty Executives Premier.

Updated . Information deemed reliable but not guaranteed.

Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker of MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some listings have been excluded from this website.