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601 Long Bridge Drive, Chesterton
$295,000
4 Beds ⋅ 2 Baths ⋅ 846319 MLS ⋅ 1,945 SqFt. ⋅ Neil Csonka
Welcome home to this charming and spacious 4-bedroom, 1.75-bathroom tri-level property perfectly situated in the heart of Chesterton, Indiana. Designed with a highly functional layout, this classic tri-level architecture maximizes living space, giving your family plenty of room to spread out, entertain, and grow. Key Features You'll Love: Versatile Tri-Level Living: Enjoy a seamless flow between the distinct levels. The bright and inviting main level serves as the central hub, ideal for daily gatherings and home-cooked meals. 4 Comfortable Bedrooms: Three well-appointed bedrooms are tucked away on the upper level, while a versatile fourth bedroom sits on the lower level. This separate space is perfect for a quiet home office, guest suite, or related living setup. 1.75 Bathrooms: Features a full guest bathroom alongside a convenient three-quarter bath, making busy mornings a breeze. The Perfect Location: Nestled in a peaceful Chesterton neighborhood, you are just minutes away from top-rated Duneland schools, local parks, and the beautiful Indiana Dunes National Park. Plus, commuting is a breeze with easy access to major highways and the South Shore Line. Whether you're looking for a cozy retreat or a home with room to entertain, this tri-level gem delivers the perfect blend of comfort and convenience. Schedule your private showing today and see why so many love calling Chesterton home!

601 Long Bridge Drive, Chesterton

Listing courtesy of Neil Csonka from Listing Leaders MVPs.

522 Park Avenue, Chesterton
$255,000
3 Beds ⋅ 1 Baths ⋅ 846149 MLS ⋅ 1,056 SqFt. ⋅ Elizabeth Garcia
Location, convenience, and small-town charm come together in this 3-bedroom, 1-bath ranch in the heart of Chesterton! Centrally located in town, this home puts you within easy walking distance of parks, splash pads, the European Market, and the future YMCA Healthy Living Campus. Enjoy having so many of Chesterton's favorite amenities just minutes from your front door! Inside, the functional ranch-style layout offers comfortable single-level living, while the basement provides additional space and plenty of possibilities. An especially valuable feature is the well-maintained whole-house Generac generator, offering added peace of mind and convenience during power outages--an increasingly appealing benefit with the storms our area has experienced. Step outside to a fenced-in backyard with plenty of room for summer gatherings, pets, play, gardening, or simply relaxing at home. Whether you're a first-time buyer, looking to downsize, or searching for a home in a convenient in-town location, this property offers a wonderful opportunity to enjoy all that Chesterton has to offer, with the added reassurance of whole-house backup power!

522 Park Avenue, Chesterton

Listing courtesy of Elizabeth Garcia from Blackrock Real Estate Services.

224 S Calumet Road, Chesterton
$275,000
3 Beds ⋅ 2 Baths ⋅ 846148 MLS ⋅ 1,324 SqFt. ⋅ Heather Alexander
Welcome to this charming and beautifully updated 3-bedroom, 2-bath home in the heart of Chesterton just a short walking distance to town, where the character of a 1900s home meets the comfort of today's improvements! From the moment you step inside, you'll appreciate the inviting layout, beautiful flooring, original built-ins, and thoughtful updates that have brought new life to this classic home. The updated kitchen features granite countertops, plenty of cabinetry, and a fresh, functional design, while the main level bathroom includes an added shower. The upper level provides a full bathroom with a soaking tub. This home provides a detached 2 car garage and it sits on just under a quarter of an acre with a fire pit and partially fenced backyard. Even better, many of the major improvements have already been taken care of, including a new sewer in 2021, updated upstairs plumbing in 2021, updated basement/main-level plumbing in 2023, upstairs electrical updates in 2025, and a new central A/C, and whole-house ductwork in 2025. The home also features a newer roof. And then there's the location! Enjoy everything that makes Chesterton such a special place to call home. Spend Saturday mornings browsing Chesterton's European Market in historic downtown, explore local shops and restaurants, or head to the Indiana Dunes and Lake Michigan just minutes away. The European Market is held downtown from May through October, and Chesterton offers an impressive mix of dining, shopping, community events, and outdoor recreation. Chesterton has convenient access to I-94, the Indiana Toll Road, and State Road 49 which also makes getting around Northwest Indiana and beyond easy. Schedule your showing today!

224 S Calumet Road, Chesterton

Listing courtesy of Heather Alexander from @properties/Christie's Intl RE.

1954 David Drive, Chesterton
$172,500
1 Beds ⋅ 1 Baths ⋅ 845895 MLS ⋅ 780 SqFt. ⋅ Providence Community Assn Inc BLDG. ⋅ Sarah Eenigenburg
This charming 1-bedroom, 1-bath condo offers comfortable, maintenance-free living in a convenient location. Enjoy home ownership without the hassle of exterior maintenance, giving you more time to enjoy your home and everything the area has to offer. The inviting layout provides a comfortable space to relax and entertain, making this an excellent option for a first-time buyer, downsizer, or anyone looking for a low-maintenance lifestyle. Conveniently located near shopping, dining, parks, and major transportation routes, this condo combines comfort and convenience. HOA includes trash pick up, water, sewer, snow removal, landscaping, and building maintenance! Don't miss this opportunity! Schedule your showing today!

1954 David Drive, Chesterton

Listing courtesy of Sarah Eenigenburg from Better Homes and Gardens Real.

1708 Tower Street, Chesterton
$249,000
2 Beds ⋅ 1 Baths ⋅ 845440 MLS ⋅ 1,250 SqFt. ⋅ Marcy Norman
This charming two bedroom, one bath home is ready for its new owners. You'll love the refinished hardwood floors and wide trim that carry classic character throughout the home. Original solid wood doors with antique hardware add timeless appeal, while modern updates provide peace of mind. The home features newer windows, siding, furnace, and A/C, along with updated electrical. The kitchen and bathroom include built ins for added storage and style. Both bedrooms offer large walk in closets with lighting, a rare find in a home of this era. A perfect blend of vintage charm and thoughtful updates -- move in ready and full of personality. The attic space has the potential for future expansion and more living space. The large 2.5 car garage is truly a dream workspace. It's fully equipped with electric and even includes an A/C unit to keep you cool on hot days while tackling projects, hobbies, or storage needs. Plenty of room, plenty of comfort, and plenty of possibilities. Just minutes from major highways and next to the Duneland walking trail.

1708 Tower Street, Chesterton

Listing courtesy of Marcy Norman from Trendsetters Realty, LLC.

201 S 8th Street, Chesterton
$234,900
3 Beds ⋅ 2 Baths ⋅ 845277 MLS ⋅ 2,348 SqFt. ⋅ Wendy Hammonds
Historic Chesterton gem just steps from downtown! This solidly built 3-bedroom, 2-bath two-story home offers nearly 2900 sq. ft. of finished living space which includes a full basement. Beautiful original woodwork, doors, hardware and classic door knobs preserve the character of this special home, complemented by hardwood flooring. The bright, inviting kitchen features beautiful cabinetry and a convenient pantry. The updated main-level bathroom includes a charming clawfoot tub. Upstairs, the spacious primary bedroom offers a walk-in closet plus its own sitting area, filled with natural light. Situated on a desirable corner lot in Duneland School District and within walking distance to downtown Chesterton's shops, restaurants and amenities. Conveniently located near the beach and South Shore train station for those commuters. Historic charm, space, location and character--this is one you won't want to miss!

201 S 8th Street, Chesterton

Listing courtesy of Wendy Hammonds from Key Realty Indiana, LLC.

376 Cherry Hills Drive, Chesterton
$349,000
4 Beds ⋅ 2 Baths ⋅ 845256 MLS ⋅ 2,535 SqFt. ⋅ Villages/Sand Crk Ph 2 BLDG. ⋅ Marina Klein
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. This townhome checks all the boxes: 4 bedrooms, 2 full baths, full basement & a 2 car garage. This home has MAIN FLOOR LIVING with laundry and primary bedroom, full bathroom with double sinks, a shower and jetted tub on the main floor. The living room boasts a vaulted ceiling and fireplace, leading to the kitchen and dining room area with all stainless appliances, pantry and a nice sliding glass door that leads to the back patio. The upper level has a full bathroom and 3 large bedrooms with huge walk-in closets and there is an additional walk-in storage closet. The basement offers an additional 1,272 sq ft of space that is ready to be finished. This home is minutes from 80/94, 80/90, Coffee Creek, the Indiana Dunes State Park, downtown Chesterton shopping, restaurants, farmers markets, parks and so much more!

376 Cherry Hills Drive, Chesterton

Listing courtesy of Marina Klein from Blackrock Real Estate Services.

656 S 4th Street, Chesterton
$259,000
4 Beds ⋅ 2 Baths ⋅ 844916 MLS ⋅ 1,542 SqFt. ⋅ Jasmine Gonzalez
Price Improvement from this motivated seller! Bring an offer! Remodeled home in a highly desired location! Location is one of the key features of this home located 5 minutes from Hwy 49, the Dunes, and approximately 45 minutes from Chicago. The up and coming downtown Chesterton, YMCA, Chesterton Park, and splash pad are only 3 minutes away. Bailey Elementary & Montessori School are only a few blocks away. Featuring a spacious updated living room with a beautiful fireplace. The formal dining room is a wonderful addition to the home. The modern kitchen includes new flooring, cabinets, countertops, and bar overhang for barstools. A full bathroom was added downstairs. There is a small office and bedroom with bathroom on the main level. Upstairs you will find 2 spacious updated bedrooms. The backyard space has been transformed into a private oasis with edible grapes on the fence. The storage shed is perfect for storing outdoor equipment. The home sits on a nice size lot with additional yard space to the right of the carport. Enjoy lower taxes and a quiet neighborhood.

656 S 4th Street, Chesterton

Listing courtesy of Jasmine Gonzalez from Coldwell Banker Realty.

1622 Port Cove Drive, Chesterton
$327,500
3 Beds ⋅ 3 Baths ⋅ 840225 MLS ⋅ 3,484 SqFt. ⋅ Brian Manning
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. This residence blends functionality and relaxation in a desirable neighborhood and is ready for some fresh updates. Homeowners are motivated to sell. Step inside to find a spacious and inviting layout. The tri-level design provides excellent separation of spaces: the main level features an eat-in kitchen and living areas perfect for everyday living and entertaining, while the upper level offers private bedroom retreats, including a main bedroom with its own ensuite bathroom. Three full bathrooms ensure convenience for everyone in the household. The highlight of this home is the fenced backyard oasis. Enjoy summer days on the large deck, cool off in the above-ground pool, or gather around the fire pit for evenings under the stars. With plenty of room to play or garden, this outdoor space is ready for memories. A 2-car garage adds practical convenience for parking and storage. Located in Porter, you're just minutes from the stunning Indiana Dunes National Park and State Park, with miles of beaches, hiking trails, and Lake Michigan views. The vibrant Chesterton area offers excellent amenities including shops, restaurants, schools, and easy access to major routes -- perfect for commuters while still providing a peaceful suburban feel. This tri-level home combines comfort, outdoor enjoyment, and unbeatable location. With motivated sellers and a home ready for your personal updates, don't miss your chance to make it yours!

1622 Port Cove Drive, Chesterton

Listing courtesy of Brian Manning from Listing Leaders.

1248 Dogwood Drive, Chesterton
$325,000
3 Beds ⋅ 2 Baths ⋅ 838462 MLS ⋅ 1,419 SqFt. ⋅ Jamie Bond
Deal Fell Thru No Fault to Seller!!! Perfectly Located Just Minutes from the Indiana Dunes National Park and Lakeshore. This Classic Ranch is Nestled Among Mature Trees in a Quant Neighborhood, Offering a Rare Blend of Quality Craftsmanship and Commuter Convenience. The Open -Concept Design Features Vaulted Ceilings, Stunning Cedar Accents, and an Original 1963 Floor to Ceiling Brick Fireplace Extending to the Unfinished Basement, Serving as a Striking Mid- Century Focal Point. The Custom Kitchen Showcases Quartz Countertops and Handcrafted Cabinetry Made from a Single Tree, Offering Exceptional Character and Craftmanship. The Spacious Layout Includes 3 Bedrooms and 2 Baths, including a Private Primary Suite with Attached Bath and Your Very Own Sliding Door Leading to a secluded Patio. The Unfinished Basement Provides Endless Possibilities for Additional Living Space, Storage, or Recreation. Located in the Award -Winning Duneland School District with Convenient Access to the South Shore Train Station, Toll Road and Expressways- Perfect for Chicago Commuters.

1248 Dogwood Drive, Chesterton

Listing courtesy of Jamie Bond from Listing Leaders.

769 S Calumet Road, Chesterton
$300,000
4 Beds ⋅ 2 Baths ⋅ 838403 MLS ⋅ 2,242 SqFt. ⋅ Carla Ebert-Kienitz
Step into this FABULOUS, charming home sitting on a CORNER LOT, offering 4 bedrooms, or 3 bedrooms plus an office, with character, space, and comfort throughout! The beautiful gourmet kitchen with cabinets galore is just waiting for you to host that special dinner party. The stunning formal dining room is perfect for entertaining, while the large living room with a spectacular fireplace creates the ideal place to cozy up on cool evenings. Now wait until you see the incredible upstairs retreat, a master suite to die for! Enjoy a walk-in closet that feels like an entire extra room along with your own private getaway featuring a grand 20x14 bathroom designed for relaxation and comfort. So much in this home is brand new! Beautiful arched doorways welcome you inside, while large windows flood the home with natural light. Gorgeous plank flooring flows throughout the home, complemented by new carpet in the bedrooms. Outside, you'll love the huge corner lot, fantastic location, fully fenced backyard, and gorgeous deck where you can sit and sip your favorite beverage while enjoying your own peaceful tranquility. ROOF AND GUTTERS are less than 7 months old! A fantastic 2.5-car detached garage adds even more convenience and storage space. There's even a welcoming front porch perfect for relaxing and watching the world go by. Step into tranquility with this beauty... priced under market value! and ready to welcome you home!

769 S Calumet Road, Chesterton

Listing courtesy of Carla Ebert-Kienitz from Century 21 Circle.

1717 Crocker Street, Chesterton
$249,000
3 Beds ⋅ 2 Baths ⋅ 832918 MLS ⋅ 2,400 SqFt. ⋅ Paul Boyter
Move-in ready with built-in upside, this fully remodeled 11/2-story home offers three bedrooms and two full bathrooms. The basement bedroom and bathroom will be completed before closing. Recent improvements include new roof shingles, windows, doors, trim, abundant kitchen cabinets and countertops, whirlpool tub, waterproof vinyl plank flooring throughout, and central air conditioning. Enjoy outdoor living on the spacious new wraparound deck overlooking a large backyard, ideal for relaxing or entertaining. The home is adjacent to the Duneland Prairie Bike Trail, offering immediate access to miles of scenic recreation. The basement is fully framed and electrically roughed in for a private primary suite, including a large 17x20 bedroom, walk-in closet, full bath with double vanity, and laundry area. A new egress window is already in place, making this level bright, functional, and ready to finish with minimal additional investment. Ideally located in the award-winning Chesterton school district, near Hwy 149 and County Rd 1100, this home provides quick access to shopping, restaurants, Indiana Dunes on Lake Michigan, the South Shore Train, downtown Chesterton, and the popular European Market, with an easy 45-minute commute to Chicago. A rare opportunity for turnkey comfort with strong future value.

1717 Crocker Street, Chesterton

Listing courtesy of Paul Boyter from McColly Real Estate.

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.