Chesterton, IN Homes for Sale

Completely 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

$389,000

Welcome to this 4 bedroom, 3 bath, 2-story home located in desirable Villages of Sand Creek. Main level offers a Formal Living Room as well as a Formal Dining, spacious Eat-in Kitchen which is open to the Family Room, and the Laundry Room. Upstairs you will find all 4 bedrooms freshly painted with newer carpet. The Primary Suite has an attached full bath with separate shower and tub and large walk-in closet. This home is situated on a cul-de-sac with a lovely view of the pond located across the walking path. This neighborhood is only 3 miles from the Indiana Dunes & Lake Michigan, close to restaurants, shopping, golf courses, and is an easy commute to Chicago.

378 Ballenisle Court, Chesterton

$349,900

Charming 2-Story in Chesterton -- Priced to Sell! Welcome home to this adorable two-story gem, where soaring cathedral ceilings create an airy, light-filled feel from the moment you walk in. The heart of the home is a brand-new kitchen outfitted with all-new appliances -- move-in ready and waiting for your first meal. Don't miss the sunroom, featuring its own vaulted ceilings -- the perfect spot for morning coffee or curling up with a good book. Many major updates have already been done for you: new flooring in kitchen and living room, a new hot water heater, and a new furnace, so you can settle in worry-free. Outside, you'll fall in love with the picture-perfect lot -- mature trees, a fully fenced yard, and that classic Chesterton charm on a quiet, welcoming street. Homes like this don't last. Schedule your showing today!

801 S 19th Street, Chesterton

$455,000

Welcome to 2332 Dakota Street--a beautifully **FULLY RENOVATED Cape Cod** in the highly sought-after **Duneland School District!** Nearly 3,000 sq. ft. of finished living space has been thoughtfully updated from top to bottom, offering the charm of an established home with the finishes, comfort, and peace of mind of something new. Major upgrades include a **NEW ROOF, NEW FURNACE, NEW CENTRAL A/C, and a WHOLE-HOME GENERATOR**--making this home truly move-in ready. Inside, you'll find 3 spacious bedrooms, 2.5 beautifully updated baths, TWO separate living areas, an eat-in kitchen with stone countertops and stainless steel appliances, high ceilings, recessed lighting, a main-level primary bedroom, and convenient main-level laundry. The upper level offers two generously sized bedrooms plus a large loft, providing plenty of flexibility for an office, playroom, additional lounge, or guest space. Outside, enjoy a private, landscaped **0.54-acre lot**, rear deck, storage shed, and attached 2-car garage with NO HOA. With virtually everything already upgraded, all that's left to do is move in and enjoy this stunning Chesterton home!

2332 Dakota Street, Chesterton

$455,000

This sweet villa home has everything you need--without the worry of exterior maintenance! Conveniently located on the near east side of Chesterton, you'll enjoy easy access to shopping, expressways, the train station, and one of the area's greatest attractions, Indiana Dunes National Park. More than cute and gently lived in, this charming three-bedroom, two-bath, 1,700-square-foot ranch is sure to impress. The open floor plan is perfect for entertaining, with a cozy fireplace to warm you in the winter and a large patio with a retractable sunshade to enjoy during the summer. Luxury vinyl flooring runs throughout the home, with tile flooring in the bathrooms. The primary bedroom is privately situated on one side of the home, while the other two bedrooms are located on the opposite side. The primary bath features a tiled shower with a frameless glass door, double sinks, a walk-in closet with organizers, and a linen closet. The kitchen features a large island that provides additional seating, along with a beverage refrigerator, newer stainless steel appliances, and a pantry. The laundry/mudroom offers a convenient place to sit and remove your shoes, along with space for coats and keys, a storage closet, plenty of cabinetry, a washer and dryer, and a laundry sink. The slightly oversized two-car garage provides plenty of additional storage along both sides. The home's mechanicals are conveniently housed in a large garage closet, and pull-down attic stairs provide access to even more floored storage above the garage. The maintenance package makes life easy and includes lawn mowing, snow removal up to your door and driveway, trimming, fertilizing, and spring and fall sprinkler-system maintenance. Comfortable, convenient, and easy to maintain--come see this one soon! .

472 Cypress Lane, Chesterton

$58,000

Phase 3 is now open and ready for building. Lot 65 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.

1000 Preserve Lane, Chesterton

$459,000

Built in 2025 and practically brand new, this beautiful 4-bedroom, 2.5-bath home offers modern finishes, a functional layout, and plenty of room to grow! The open-concept main level is designed for both everyday living and entertaining, featuring a spacious kitchen with quartz countertops, abundant counter and cabinet space, and a large center island. The kitchen flows seamlessly into the inviting living room and out to the deck, creating a great space for gatherings or relaxing outdoors. A private office and convenient half bath complete the main level. Upstairs, you'll find all four bedrooms, including a spacious primary suite with a private ensuite bath and an impressively large walk-in closet. The unfinished daylight basement provides excellent potential for additional living space, a recreation room, home gym, or whatever fits your needs. Outside, enjoy the convenience of an irrigation system and a newer home without the wait of new construction. Ideally located near downtown Chesterton with easy access to local restaurants, shops, parks, and highly regarded schools. Move right in and enjoy everything this nearly new home has to offer!

29 Karner Blue Court, Chesterton

$405,000

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 spacious primary suite features a vaulted ceiling, walk-in closet, and private full bath with a double vanity and a relaxing whirlpool tub. The new updated kitchen offers quartz counter tops, new dishwasher, abundant cabinetry, generous counter space, and a large pantry for added convenience. The huge lower-level rec room with a cozy gas fireplace provides the perfect space for entertaining or relaxing. The main level flooring has been updated with waterproof, scratch resistant, realistic wood grain LVP flooring, and outlets have been strategically installed higher on the walls in the bedrooms and rec room for easy TV mounting and setup. Enjoy the backyard with storage shed and plenty of room for outdoor activities. The exterior also features all season Govee lighting to really give your home that pop all year round. Frontier fiber optic cable has also been recently ran underground. A must-see home that combines quality craftsmanship, thoughtful updates, and functional living space.

1927 Cory Lane, Chesterton

$314,900

Great location right in the heart of Duneland, near the new YMCA Healthy Living Campus! This move-in ready ranch features 4 bedrooms, 2.5 baths, a brand-new roof, and new gutters for total peace of mind. Step inside to a bright, inviting living room with oversized windows that flood the space with natural light and highlight the newly refinished wood floors flowing into the office area. The entire home is freshly painted and welcoming. The highly functional kitchen boasts a center island, abundant cabinet space, and generous countertops. Just off the kitchen, the spacious dining room easily accommodates all your entertaining needs, while a versatile flex room makes a perfect home office or playroom. Cozy up in the expansive great room featuring a custom-built fireplace--ideal for cool winter nights. As an added perk, you'll find a cable-ready bonus room above the garage, offering the ultimate media room, teen hangout, or secluded retreat!

419 S 9th Street, Chesterton

$419,900

Construction Complete - July! MOVE IN READY! The Preserve in the Duneland School Corp. This 2,735 square foot home makes an unforgettable impression. Off the foyer, a private den with French doors offers a quiet, refined space for a home office or study, while a discreetly placed powder room at the front of the home adds convenience without interrupting the flow. The heart of the home unfolds into a spacious great room filled with natural light and inviting views of the backyard. A dedicated dining nook bridges the great room and kitchen, with sliding glass doors that extend gatherings outdoors. The kitchen is both expansive and elegant, anchored by a striking 72-inch island with pendant lighting and an extended edge for barstool seating. Quartz countertops, a tile backsplash, and stainless steel range, dishwasher, and microwave complement the modern, open layout, while a large pantry adds impressive built-in storage. The mudroom connects seamlessly to the attached garage and includes a built-in bench and oversized walk-in closet, creating an organized landing zone for everyday living. Upstairs, four bedrooms each feature their own walk-in closet, offering exceptional storage and personal space, along with a well-appointed full bath that serves the secondary bedrooms with comfort and convenience. A conveniently located laundry room on this level adds everyday ease right where it's needed most. The primary suite stands out as a true retreat, complete with a private bath and an oversized walk-in closet designed to impress. Blending dramatic architectural elements with thoughtful functionality, this home delivers the kind of space, style, and presence that leaves a lasting impact. RESNET energy smart construction will save an estimated 1,699 annually. Actual savings may vary; see HERSA(r) Rating Certificate and Energy Smart Flyer for details. Home includes a 10-year structural warranty, offering lasting peace of mind. Contact our team to schedule your private tour today!

40 Karner Blue Court, Chesterton

$539,900

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 extending throughout the main level, featuring a formal dining room. French doors from a den/office and flow into the family room, highlighted by a gas-start fireplace and a wall of windows showcasing the woods. The open-concept layout effortlessly connects the family room, eating area, and peninsula counter kitchen, which boasts painted oak cabinets, solid surface countertops, and recessed lighting. The rear hallway leads to the laundry room, a 3-car garage, and a vaulted ceiling screen porch with skylights. Step outside to a private, professionally designed outdoor oasis featuring a paver patio, a granite gas grill island with bar seating, a 55" outdoor TV in a storm box, a wood-burning fireplace, and a 4-person hot tub. Upstairs, the primary suite offers vaulted ceilings, a walk-in closet, a double vanity, a soaking tub, and separate shower, alongside three additional bedrooms and a full bath. The garage features a walk-up attic stairwell for easy storage or potential expansion with access through the 4th bedroom too. Complete with zoned 2010 Lennox HVAC and city utilities, this property offers quick access to Highways 49, I-90, and I-94 and near the Indiana Dunes National Park.

131 Beverly Drive, Chesterton

$749,700

3 Beds ⋅ 4 Baths

Welcome to 1909 Catkin Circle, an impressive fully updated Modern Farmhouse located in the highly desirable Tamarack Subdivision of Chesterton. Situated on nearly half an acre with beautiful pond views, this 4,284 sq. ft. home offers exceptional indoor and outdoor living with mature landscaping surrounding the property and an expansive wraparound porch. Inside, you'll find 3 bedrooms and 3.5 bathrooms with a thoughtfully designed layout featuring an enlarged, vaulted primary suite, a spacious butler's pantry, and inviting living and entertaining spaces throughout. Three fireplaces add warmth and character, while a whole-house entertainment speaker system makes the home ideal for both everyday living and hosting. The Modern Farmhouse design carries throughout the home, combining updated finishes with comfortable, functional spaces. Step outside to enjoy the wraparound porch, professionally landscaped grounds, and peaceful pond setting that make this property stand out within Tamarack. With 4,284 square feet of living space, a premium pond-side lot, extensive updates, and a combination of luxury, privacy, and character, 1909 Catkin Circle offers a rare opportunity in one of Chesterton's desirable residential communities.

1909 Catkin Circle, Chesterton

$419,900

This meticulously updated four-bedroom, three-bathroom residence is situated in a prime Chesterton location. The interior features a thoughtfully redesigned kitchen equipped with custom hickory cabinetry, granite countertops, and premium stainless-steel appliances. Abundant natural light fills the living room through a newly installed expansive window, flowing seamlessly into a spacious dining area and a comfortable sunroom - perfect for morning coffee and evening relaxing. The home offers four generously proportioned bedrooms, including two en-suite bathrooms located on the upper and lower levels respectively, all complemented by new modern vanities and fixtures. Fresh interior paint, new lighting, and a combination of new carpeting and new luxury vinyl plank flooring complete the refined interior. Additional versatility is provided by lower-level bonus spaces suitable for a recreation room, home gym, or multi-generational living arrangements. The attached garage features all-new shelving and a new insulated overhead door with new quiet, side-mount opener. Exterior improvements include a new roof installed in 2025, upgraded gutters, fascia, soffit, exterior doors, and a newly constructed composite front porch. Conveniently positioned on a dead-end, cul-de-sac street, the property offers exceptional proximity to schools, parks, shopping, commuter transit, major interstates, and the Indiana Dunes National Park. Schedule your showing today!

762 Dunewood Drive, Chesterton

$649,900

Rarely available home in the sought after Tamarack subdivision. Elegant custom-built brick ranch with impressive curb appeal, lush landscaping, and a grand columned entry. Soaring ceilings, arched openings, abundant natural light, and hardwood floors create an inviting interior, while the spacious living room features a fireplace and flows easily into the formal dining room and breakfast area. The kitchen offers rich wood cabinetry, generous counter space, stainless steel appliances, a center island, and a built-in oven and microwave installed in 2022. The primary suite includes vaulted ceilings, plantation shutters, dual vanities, a walk-in tub, separate shower, and walk-in closets. Highlights include main-level laundry, furnace and central air replaced in 2020, a 2026 garage door opener, exterior railings, a huge unfinished basement with an egress window and flexible studio, recreation, hobby, and storage space. Enjoy the resurfaced covered patio, colorful gardens, and private tree-lined backyard.

1910 Catkin Circle, Chesterton

$399,500

Bring your offer!!! Calling all buyers, contractors, and investors who see potential where others see projects. Some pictures are AI generated. See what the potential is when changing out the paint, carpet, laundry room flooring and stainless appliances. This 3-bed, 3-bath ranch home on a 0.77 acre lot in Chesterton is a rare chance to build instant equity in one of Northwest Indiana's most sought-after school districts. The roof is only 1 year old -- one of the biggest-ticket items already handled for you. Beneath the cosmetic wear is a home with genuinely good bones: a solid layout, real square footage (2232= 1st floor + 2232 =unfinished basement), and a floor plan worth restoring rather than replacing. Yes, it needs work -- this is NOT a move-in-ready listing, and it's priced accordingly. But for the right buyer, that's exactly the point. Bring your contractor, your vision, or your renovation loan, and turn this into serious equity in a market where finished homes are commanding a premium. In-ground pool, expansive decking, additional 2 car detached garage at the back of the property. Located minutes from downtown Chesterton, the South Shore Line, and the Indiana Dunes, with access to Duneland Schools -- this is a location buyers don't want to miss, at a price point that leaves room to make it your own.

1776 Indian Boundary Road, Chesterton

$714,900

Welcome Home to the Ruby on Lot 12 in 1100 Woods! This new build is on one of the last tree lined lots left and features 4 generous sized bedrooms upstairs including a primary ensuite with walk in shower and soaking tub and walk in closet with additional den/office on main level. Open concept living room and island and pantry in kitchen. Price includes lot cost and lookout basement option, 9 foot ceilings on main floor, upgraded black windows, upgraded cabinet package, basement bath rough in for future bathroom, and a 12x14 composite rear deck. Full unfinished basement with lookout windows to your beautiful backyard trees! AND in addition to the 2 car garage it had a 5 foot garage bump out for added storage. This community is located just across the street from Dogwood Park and walking distance to the Prairie Duneland trail! This home is under construction with a spring move in date and you can stop by 2179 W 1100 to see our model home and the finishes selected for this build!

2519 Pradera Trail, Chesterton

$360,000

Welcome to this beautifully maintained 3-bedroom, 2.5-bath home in desirable Olde Towne Square! This spacious 2-story home offers an open-concept main level with a generous kitchen featuring ample cabinet and counter space, newer stove, and easy flow into the dining and living areas. The upper level features a large primary suite with walk-in closet and private bath, along with two additional bedrooms and a full bath. Enjoy the convenience of an attached 2-car garage with extra 8' x 8' storage/workspace in the back, providing additional room beyond the standard garage footprint. The home also features a furnace that is approximately 1 year old and gas piping already in place for a future fireplace, offering the opportunity to add a fireplace down the road. Finished basement space provides even more flexibility for a recreation room, home office, or additional living space. Conveniently located near shopping, dining, schools, parks, major highways, and train transportation to Chicago, making commuting to the city a breeze. Schedule your showing today!

803 Olde Towne Square, Chesterton

$699,900

Welcome to one of out most desirable floorplans in 1100 Woods! This is PROPOSED CONSTRUCTION and we invite you to visit 2179 W 1100 which is the model home for this listing. The Madeleine features a primary ensuite on the main level, a large office/den, a 20 ft foyer and great room and an oversized chefs kitchen with walk in pantry. Upstairs you will find 2 additional bedrooms, full bathroom and loft. A large bonus room also doubles as a 4th bedroom.

1719 S 23rd Street, Chesterton

$614,900

Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Duneland trail. The Bassett Grove is PROPOSED CONSTRUCTION on LOT 30.. A 2 story with primary en suite on main level and 2 separate guest bedrooms upstairs with full bathroom. Standard finished include Luxury vinyl Plank flooring, quartz or granite countertops, custom cabinets and a spa like primary ensuite. Numerous options to choose from and we invite you to visit the design center at 2179 W 1100 to start your new build!

2274 Pradera Trail, Chesterton

$599,900

4 Beds ⋅ 2 Baths

Welcome to 1100 woods! A beautiful community of 35 homes located in the heart of Chesterton and across the street from Dogwood Park and walking distance to the Prairie Duneland trail. The Windmill model is PROPOSED CONSTRUCTION on Lot 30. A sprawling ranch with an impressive great room and boasts 4 bedrooms and a full unfinished basement to give you 4,000 sqft of potential living space. Standard finished include Luxury vinyl Plank flooring, quartz or granite countertops, custom cabinets and a spa like primary ensuite. Numerous options to choose from and we invite you to visit the design center at 2179 W 1100 to start your new build!

2246 Pradera Trail, Chesterton

$58,000

Phase 3 is now open and ready for building. Lot 91 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 You Neighbor.

37 Karner Blue Court, Chesterton

$529,900

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, this premium homesite is uniquely positioned with protected wetlands bordering one side and extending behind the backyard, creating exceptional privacy and picturesque year-round views. The open-concept floor plan seamlessly connects the kitchen, dining area, and great room, creating an inviting space for everyday living and entertaining. A covered rear porch extends the living space outdoors, providing the perfect spot to enjoy morning coffee or unwind while overlooking the natural landscape. At the heart of the home, the kitchen features classic shaker cabinetry, stainless steel appliances, a generous pantry, large island, and abundant counter space, blending timeless style with everyday functionality. The main-level primary suite offers the ease of first-floor living with a spacious retreat featuring a dual-sink vanity, soaking tub, tiled walk-in shower, and oversized walk-in closet. A powder room, laundry/mudroom, and attached two-car garage complete the main level. Upstairs, two additional bedrooms, a full bath, and a versatile loft provide flexible space for a home office, media room, playroom, fitness area, or additional lounge. Premium features include 42-inch soft-close cabinetry, luxury vinyl plank flooring throughout the main living areas, a fireplace, Andersen windows, a high-efficiency HVAC system, professionally designed landscaping, and a finished two-car garage. Buyers also have the opportunity to personalize select interior finishes during construction. Located within The Preserve, a thoughtfully planned community spanning more than 90 acres of protected natural landscape, residents enjoy privacy, scenic beauty, and everyday convenience just 40 miles SE of Chicago, with easy access to shopping, dining, highly rated schools, commuter routes, the South Shore Line and Indiana Dunes.

1036 Preserve Lane, Chesterton

$525,500

Beautiful new construction ranch, offering nearly 1,900 square feet of thoughtfully designed living space in The Preserve. Situated on a premium homesite bordering protected wetlands, this home offers serene views, added privacy, and a peaceful natural setting. The open-concept floor plan seamlessly connects the kitchen, dining area, and great room, extending to a private rear deck perfect for outdoor dining, relaxing, or entertaining. Large Andersen windows and elevated ceilings fill the home with natural light, creating a bright atmosphere. The well-designed layout includes three bedrooms plus a dedicated office, providing flexibility for remote work, guests, or additional living space. The kitchen blends timeless style and everyday functionality with classic shaker cabinetry, stainless steel appliances, a generous pantry, large island, and abundant counter space. The spacious primary suite offers a private retreat with a dual-sink vanity, beautifully tiled walk-in shower, expansive walk-in closet, and an additional oversized closet for exceptional storage. A standout feature is the unfinished daylight basement overlooking the protected wetlands, complete with full-size windows that provide abundant natural light. Future expansion offers endless possibilities for a recreation room, home gym, media room, guest suite, home office, or additional bedrooms. Plumbing is already roughed in for a future full bathroom, making it easy to customize as your needs evolve. Premium features include 42-inch soft-close cabinetry, LVP flooring throughout the main living areas, Andersen windows, a high-efficiency HVAC system, professionally designed landscaping, and a two-car garage. Located within The Preserve, a thoughtfully planned community spanning 90 acres of protected natural landscape, residents enjoy privacy and convenience just 40 miles SE of Chicago, with easy access to shopping, dining, highly rated schools, commuter routes, the South Shore Line, and Indiana Dunes.

1002 Preserve Lane, Chesterton

$519,900

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 natural buffer, this home offers peaceful views and a tranquil setting. The open-concept floor plan seamlessly connects the kitchen, dining area, and living room, extending to a private rear deck overlooking the wooded backdrop, perfect for relaxing or entertaining. Large Andersen windows and elevated ceilings fill the home with natural light, creating a bright, airy atmosphere throughout. Designed for both style and functionality, the kitchen features classic shaker cabinetry, stainless steel appliances, a generous pantry, large island, and abundant counter space for everyday living and entertaining. The spacious primary suite offers a private retreat with a dual-sink vanity, tiled walk-in shower, expansive walk-in closet, and an additional oversized closet for exceptional storage. A standout feature is the unfinished daylight basement overlooking the natural wetlands, complete with full-size windows that provide abundant natural light. Designed for future expansion, the lower level can easily become a recreation room, home gym, media room, guest suite, home office, or additional bedrooms. Plumbing is already roughed in for a future full bathroom, providing even more flexibility to customize the space. Premium features include 42-inch soft-close cabinetry, LVP throughout the main living areas, fireplace, Andersen windows, a high-efficiency HVAC system, professionally designed landscaping, and a finished two-car garage. Buyers also have the opportunity to personalize select interior finishes during construction. Located within The Preserve, a thoughtfully planned community spanning 90 acres of protected natural landscape, enjoy privacy and convenience just 40 miles SE of Chicago, with easy access to shopping, dining, highly rated schools, commuter routes, the South Shore Line, and Indiana Dunes.

1003 Preserve Lane, Chesterton

$167,000

2 Beds ⋅ 1 Baths

Maintenance-Free Living at Its Best! Welcome home to this beautifully maintained main-level ranch-style condominium offering comfort, convenience, and an unbeatable location. This inviting home features 2 bedrooms and 1 beautifully remodeled bathroom, along with a warm and welcoming living room highlighted by a cozy fireplace and sliding glass doors leading to the patio--perfect for relaxing or enjoying your morning coffee. The updated kitchen showcases newer soft-close cabinetry, a convenient pass-through opening to the living room that enhances the open feel, and all appliances are included--including the stackable washer and dryer. A smart thermostat adds modern convenience and energy efficiency. Ideally situated in the highly sought-after Duneland School District, this home is just minutes from the Indiana Dunes State Park and Indiana Dunes National Park, offering endless opportunities for hiking, beaches, and outdoor recreation. Commuters will appreciate the easy access to major highways, the Indiana Toll Road, and the South Shore Line, providing convenient service to both Chicago and South Bend. Enjoy the ease of maintenance-free living in a fantastic location close to shopping, dining, recreation, and transportation. Don't miss this wonderful opportunity! HOA fees are 332 per month with an additional 120 special assessment for 5 more payments,.

1100 Saratoga Lane, Chesterton

$649,500

3 Beds ⋅ 4 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. Offering the perfect blend of comfort, convenience, and low-maintenance living, this home is ideal for anyone looking to enjoy a relaxed lifestyle in one of Northwest Indiana's premier neighborhoods. Step inside to find a bright, inviting floor plan with spacious living areas, abundant natural light, and a layout designed for both everyday living and entertaining. The well-appointed kitchen flows seamlessly into the dining and living spaces, creating a warm and welcoming atmosphere. The generous primary suite provides a private retreat, while additional living space offers flexibility for guests, a home office, or hobbies. Enjoy your morning coffee or unwind in the evening on your private patio while taking in the peaceful surroundings. Located within the prestigious Sand Creek community, you'll appreciate easy access to golf, walking paths, shopping, dining, top-rated Duneland schools, and the beautiful Indiana Dunes National Park and Lake Michigan shoreline. With convenient access to major highways and the South Shore Line, commuting to Chicago is also within easy reach.

1429 Calais Court, Chesterton

$359,900

4 Beds ⋅ 2 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 Duneland School District, you'll enjoy being just minutes from downtown Chesterton, the Indiana Dunes National Park, Lake Michigan beaches, the South Shore Line, Coffee Creek Preserve, shopping, dining, and major commuter routes. Inside, the sunny living room welcomes you with fresh paint & neutral decor The country kitchen features brand-new quartz countertops, a pantry, a full appliance package, and sliding door access to the backyard--perfect for everyday living and entertaining. The lower level adds valuable flexible space with brand-new carpet, a cozy brick fireplace, a fourth bedroom, a 3/4 bath, dedicated laundry room, and plenty of storage. Upstairs, retreat to a spacious primary bedroom along with two additional bedrooms and an updated full bath featuring new quartz countertops. Step outside to enjoy the freshly painted deck with a Sunsetter shade, a storage shed, and a generous backyard with room for gardening, pets, play, or outdoor gatherings. The heated 2.5-car garage provides ample space for vehicles, hobbies, and extra storage. Recent updates include new paint, new carpet, new quartz countertops in the kitchen and bathrooms, updated fixtures, and a new HVAC system (2022), making this home truly move-in ready. Schedule your private showing today!

2342 Westwood Lane, Chesterton

$395,000

4 Beds ⋅ 4 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 rental unit helping offset your monthly mortgage payment. The spacious owner's residence features 2 bedrooms, 2 bathrooms, and a finished basement that provides plenty of additional living and entertaining space. The adjoining rental unit, now vacant, includes 2 bedrooms and 2 bathrooms, allowing you to choose the tenants and rents. The 455 side has a brand new air conditioner and new appliances last year. New windows were installed in 2025. Both units enjoy large, private backyards perfect for relaxing, entertaining, or gardening. Conveniently located just minutes from the beautiful beaches of Lake Michigan, charming downtown Chesterton, and the renowned European Market, this property also offers an easy commute with quick access to the South Shore Line and I-94, putting downtown Chicago within approximately 45 minutes. Whether you're looking to reduce your housing costs or expand your investment portfolio, this property offers the perfect combination of comfort, convenience, and income potential.

455 Woodlawn Avenue, Chesterton

$675,000

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. frontage on 150W. Zoned R-1 Residential. Property is currently farmed and is subject to crop rights. Located minutes from access to commuter expressways, South Shore train station, Lake Michigan and the Indiana Dunes National Lakeshore, award-winning schools, and the vibrant Chesterton downtown district for all of your shopping, entertainment, and recreation!

W 1050 N, Chesterton

$679,000

Only 3 years young- this new construction build was completed by one of NWI's most prestigious builders in the desirable Preserve neighborhood known for its thick tree lines of protected land! A backyard oasis is already complete for you and makes this home the best value you could be looking for in Chesterton! It's not everyday you see a backyard like this - inground pool with automatic safety cover, putting green and large stamped concrete patio for backyard dinners. Beautiful mature landscaping and surrounded by trees on 2 sides. The home sits on a quiet cul de sac and is a show stopper with high end finishes. A 2 story foyer greets you and welcomes you into the 2 story great room with a gas fireplace at the heart. A bright kitchen overlooking your backyard oasis and featuring quartz countertops with a six drawer island, walk in pantry with built in shelving and including a mini fridge. Off kitchen dining for casual family dinners and a formal dining for entertaining. An office, half bath and bedroom finish the main level living with mudroom access from the garage to kitchen. Upstairs you will find a beutifully appointed primary en suite with wainscotting, walk in closet with custom built in organizers, walk in tiled shower with frameless glass doors, and double vanity. 2 other bedrooms complete the upstairs along with UPSTAIRS LAUNDRY for added convenience. And last but not least a full unfinished basement of additional 1300 potential living space with 9 ft ceilings for future expansion and includes egress window for future 5th bedroom and rough in plumbing for future 4th bathroom. This home has everything you are looking for and is 15 mins from train station for easy to commute to Chicago, 10 mins from Chesterton downtown with local restaurants, coffee shops and the famous European farmers market! Award winning Duneland School system with the high school and the popular Dogwood park only 4 minutes! Taxes will be lower with new owners homestead exemption!

18 Blue Grass Way, Chesterton

$186,500

2 Beds ⋅ 2 Baths

Welcome Home! This 2 Bedroom 1.75 Bath main floor condo, has been meticulous updated and is ready for a new owner. Inside you will find newer flooring, kitchen cabinets, countertops, bathrooms, as well as newer stainless steel kitchen appliances. Main floor living at its finest! Outside you will find a patio that overlooks a large pond. This home is complete with a 1 car garage , with shelving for your storage needs. No need to worry about the exterior maintenance, grass cutting, snow removal, water and sewer bills. Those are all taken care for you through the Association. Just move right in!

1913 David Drive, Chesterton

$74,000

A unique opportunity awaits in the gated Sand Creek community, where very few vacant lots remain! Bring your own builder and create the home you've been dreaming of. Thanks to the lot's unique layout, it offers exciting design possibilities within one of Northwest Indiana's most sought-after neighborhoods. Ideally located just one hour from downtown Chicago, Sand Creek offers the perfect balance of luxury living and convenience. The South Shore Line commuter rail is just minutes away, making travel to and from Chicago effortless. Residents also enjoy being only minutes from the breathtaking shores of Lake Michigan, the nationally renowned Indiana Dunes National Park, miles of scenic hiking and biking trails, charming downtown Chesterton, and an abundance of local dining and shopping. Residents also have the opportunity to join the private Sand Creek Country Club, located just a golf cart ride away. Membership offers exceptional amenities, including championship golf, a golf simulator, swimming, tennis, fitness facilities, private dining, a pub, and a vibrant calendar of social events. Don't miss this rare opportunity to build your custom home in one of Northwest Indiana's premier gated communities with limited homesites remaining.

1800 Bramble Trace, Chesterton

$309,000

Welcome to this 4-bedroom, 3-bathroom tri-level home located in the Porter Cove neighborhood of Chesterton. The upper level features three bedrooms, including the primary suite with its own private ensuite bathroom, while the lower level offers a fourth bedroom, an additional living room, and a newly finished third bathroom with a walk-in shower and glass doors, creating a flexible space for guests, related living, or a home office. New carpet adds a fresh update, and the attached garage provides everyday convenience. Step outside to a large patio overlooking the fenced backyard, complete with a storage shed for additional storage. Conveniently located near the Duneland Prairie Bike Trail, Indiana Dunes National Park, and the beaches of Lake Michigan, this home offers easy access to outdoor recreation year-round. Commuters will appreciate the close proximity to the South Shore Line, I-94, and the Indiana Toll Road, making travel to Chicago and surrounding communities simple and convenient. Offering a functional layout, recent updates, and a location close to both nature and commuter routes, this home is ready for its next owner.

1412 Essex Drive, Chesterton

$242,900

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

$559,900

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

$519,900

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

$569,900

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

$475,000

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

$269,900

2 Beds ⋅ 1 Baths

515 S Park Drive, Chesterton

$97,500

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! This vacant lot backs directly to the golf course, 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

$97,500

Build your dream home on this exceptional golf course homesite in the prestigious Sand Creek Country Club community! This vacant lot backs directly to the golf course, 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.

1180 Monterey Drive, Chesterton

$875,000

5 Beds ⋅ 5 Baths

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

$449,900

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

$449,900

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

$799,000

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

$125,000

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.

898 Lot 131 Michael Drive, Chesterton

$529,900