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1954 David Drive, Chesterton
$168,000
1 Beds ⋅ 1 Baths ⋅ 845895 MLS ⋅ ACTIVE Status ⋅ Providence Community Assn Inc BLDG.
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
429-431 Woodlawn Avenue, Chesterton
$347,900
4 Beds ⋅ 4 Baths ⋅ 845634 MLS ⋅ ACTIVE Status
Profitable duplex located less than 1 hour from Chicago, 10min to the South Shore Train, & 5min to I-94. Gross over 26,000 per year or live on one side & have your mortgage covered by passive income. You'll love this recently updated property with spacious rear yard, raised decks & 2 storage sheds. Loads of parking with an oversized driveway creating loads of space. Tenants pay utilities making for easy management & maximizing your bottom line. Management companies available as well. Weather you are starting your investment portfolio or looking to expand, this property will be a great asset to have.

429-431 Woodlawn Avenue, Chesterton
2555 Springdale Street, Chesterton
$329,900
3 Beds ⋅ 2 Baths ⋅ 845617 MLS ⋅ ACTIVE Status ⋅ Springdale Ph 3 BLDG.
Step into this nearly new Move-In ready 3- Bedroom, Maintenance-Free Ranch Duplex in Springdale! Open Concept layout with lots of natural light and beautiful Vinyl flooring. Enjoy a cozy night by the fireplace in the Great Room while making dinner or watching a movie. Kitchen has Maple cabinets, granite countertops and stainless steel appliances. The Master has an en suite with a double vanity and spacious walk-in closet. Sliding doors in the Kitchen lead to a covered patio. The neutral palette throughout this immaculate home will make moving in feel effortless!

2555 Springdale Street, Chesterton
1708 Tower Street, Chesterton
$239,900
2 Beds ⋅ 1 Baths ⋅ 845440 MLS ⋅ ACTIVE Status
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
2941 Nautica Drive, Chesterton
$585,000
5 Beds ⋅ 5 Baths ⋅ 845429 MLS ⋅ ACTIVE Status
Welcome Home to space, comfort, and community await you at 2941 Nautica Drive. This exceptional 5-6 Bedroom, 4 bathroom, single-family home features over 4,500 square feet of functional living space designed for a modern lifestyle. A massive kitchen, oversized island, dining area, living room with fireplace and 2 bedrooms on the main level. 2nd level offers oversized main bedroom suite with Full bathroom and walk-in closets and 3 additional bedrooms. 3rd level offers a bonus room (currently used as a bedroom suite). Finished basement offers so much more living space. 2 family room areas, Open Concept, 3/4 bath with walk-in shower, another bedroom/office area, storage and more. Enjoy a large 0.44 acre yard perfect for outdoor fun and your very own basektball court, attached 3 car garage with extra storage area. Nestled within a highly desired neighborhood, this home is a rare find. Here is an added bonus, this home was custom built with it's own Storm Shelter Room in the basement, Priced Below Market value. Call today for a private showing and make this your new home tomorrow!

2941 Nautica Drive, Chesterton
201 S 8th Street, Chesterton
$229,900
3 Beds ⋅ 2 Baths ⋅ 845277 MLS ⋅ ACTIVE Status
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
376 Cherry Hills Drive, Chesterton
$339,000
4 Beds ⋅ 2 Baths ⋅ 845256 MLS ⋅ ACTIVE Status ⋅ Villages/Sand Crk Ph 2 BLDG.
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
1063 Frontage Road, Chesterton
$199,900
3 Beds ⋅ 2 Baths ⋅ 845153 MLS ⋅ ACTIVE Status
Welcome to your new warm and cozy home! You'll enjoy the fireplaces, solid hardwood floors and privacy from your back yard. The home is situated on over 4 acres and is adjacent to protected wetlands. It is also close to shopping, expressways and the Indiana Dunes. The windows, furnace, air conditioner and hot water heater are newer. Come take a look!

1063 Frontage Road, Chesterton
1430 N Veden Road, Chesterton
$349,900
3 Beds ⋅ 2 Baths ⋅ 845085 MLS ⋅ ACTIVE Status
Welcome to this beautifully updated and thoughtfully maintained 3-bedroom, 1.5-bath home, perfectly situated on an expansive .48-acre lot within the highly sought-after Duneland School Corporation. With approximately 1,400 square feet of comfortable living space, this home offers the ideal blend of modern updates, functionality, and peaceful outdoor space. The home was completely taken down to the studs and renovated approximately five years ago, providing an impressive list of major improvements including new windows, roof, siding, furnace, air conditioning, vinyl flooring, well, septic system, and a newly paved driveway. The thoughtful updates continue with new storm doors in 2025 and, in 2026, a new shower with warranty, new shed, owned water softener, and new sump pump with a battery backup system. The stainless-steel appliances are included, and the versatile mudroom adds even more functionality with the flexibility to serve as a home office, den, or additional everyday living space. Step outside and enjoy the beauty and privacy of nearly half an acre. The spacious, well-maintained yard provides plenty of room for entertaining, gardening, pets, play, or simply enjoying your own outdoor retreat. With extensive updates, major systems already addressed, a beautiful lot, and the advantage of Chesterton schools, this is a home that offers both comfort and peace of mind. A wonderful opportunity to enjoy a move-in-ready property with nothing left to do but make it your own!

1430 N Veden Road, Chesterton
1227 W Porter Avenue Unit #1217, Chesterton
$869,000
845034 MLS ⋅ ACTIVE Status
Six-unit multifamily property in Chesterton, built in 1999 and masonry-framed over two stories: four two-bedroom, one-bath units and two one-bedroom, one-bath units across 4,952 SF, averaging 825 SF per unit on a 0.27-acre parcel with 16 off-street parking spaces. Address range 1217 to 1227 W Porter Ave. Unit finish is unusually strong for the price point. Every unit carries its own forced-air furnace, central air conditioning and water heater, and the county record card values in-unit fireplaces at 30,200 dollars. Tenants pay their own gas, electric and in-unit water, leaving ownership responsible only for common-area electric, water and sewer, trash and grounds. That structure holds the current expense load to 36.8 percent of collected income and produces in-place NOI of 52,281 dollars, a going-in cap rate of 6.02 percent at the offering price. The value-add case is the rent roll. In-place rents average 1,158 dollars per unit against ownership pro forma of 1,528, roughly 32 percent of embedded upside, with two units already on month-to-month terms and a third rolling in January 2027. Marked to those levels the property produces pro forma NOI of 69,515 dollars, a cap rate of 8.00 percent at the offering price, with no change to the physical plant. Chesterton sits inside the Duneland School Corporation, minutes from I-94, US-20 and the Dune Park South Shore station, and adjacent to Indiana Dunes National Park.

1227 W Porter Avenue Unit #1217, Chesterton
656 S 4th Street, Chesterton
$248,000
3 Beds ⋅ 2 Baths ⋅ 844916 MLS ⋅ ACTIVE Status
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
2332 Dakota Street, Chesterton
$425,000
3 Beds ⋅ 3 Baths ⋅ 844895 MLS ⋅ ACTIVE Status
SELLER OFFERING RATE BUY DOWN!! 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
1000 Preserve Lane, Chesterton
$58,000
844741 MLS ⋅ ACTIVE Status
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
1927 Cory Lane, Chesterton
$388,000
4 Beds ⋅ 3 Baths ⋅ 844671 MLS ⋅ ACTIVE Status
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
40 Karner Blue Court, Chesterton
$399,900
4 Beds ⋅ 3 Baths ⋅ 844618 MLS ⋅ ACTIVE Status
New construction home including irrigation, hydroseed and professional landscape package in 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 HERS Rating Certificate and Energy Smart Flyer for details. Home includes a 10-year structural warranty, offering lasting peace of mind.

40 Karner Blue Court, Chesterton
1910 Catkin Circle, Chesterton
$599,000
3 Beds ⋅ 3 Baths ⋅ 844240 MLS ⋅ ACTIVE Status
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
37 Karner Blue Court, Chesterton
$58,000
843917 MLS ⋅ ACTIVE Status
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
1036 Preserve Lane, Chesterton
$529,900
3 Beds ⋅ 3 Baths ⋅ 842683 MLS ⋅ ACTIVE Status
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
1002 Preserve Lane, Chesterton
$525,500
3 Beds ⋅ 2 Baths ⋅ 842682 MLS ⋅ ACTIVE Status
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
1003 Preserve Lane, Chesterton
$519,900
3 Beds ⋅ 2 Baths ⋅ 842680 MLS ⋅ ACTIVE Status
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
1100 Saratoga Lane, Chesterton
$167,000
2 Beds ⋅ 1 Baths ⋅ 843607 MLS ⋅ ACTIVE Status ⋅ Westchester Village BLDG.
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
1429 Calais Court, Chesterton
$649,500
3 Beds ⋅ 4 Baths ⋅ 843487 MLS ⋅ ACTIVE Status ⋅ Chateaux Du Chamborde Condos BLDG.
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
2342 Westwood Lane, Chesterton
$349,900
4 Beds ⋅ 2 Baths ⋅ 843482 MLS ⋅ ACTIVE Status
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
455 Woodlawn Avenue, Chesterton
$385,000
4 Beds ⋅ 4 Baths ⋅ 843317 MLS ⋅ ACTIVE Status
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
W 1050 N, Chesterton
$675,000
843301 MLS ⋅ ACTIVE Status
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
1913 David Drive, Chesterton
$179,999
2 Beds ⋅ 2 Baths ⋅ 843092 MLS ⋅ ACTIVE Status ⋅ Westchester Village Condo BLDG.
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
1065 N 50 W, Chesterton
$242,900
843035 MLS ⋅ ACTIVE Status
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
321 Broadway Avenue, Chesterton
$459,000
842974 MLS ⋅ ACTIVE Status
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
515 S Park Drive, Chesterton
$259,900
2 Beds ⋅ 1 Baths ⋅ 842889 MLS ⋅ ACTIVE Status

515 S Park Drive, Chesterton
229 E Morgan Avenue, Chesterton
$875,000
5 Beds ⋅ 5 Baths ⋅ 842756 MLS ⋅ ACTIVE Status
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

Updated . Information deemed reliable but not guaranteed.

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