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Single Family Homes for Sale in Chesterton, IN

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Welcome to your dedicated resource for single family homes for sale in Chesterton, IN. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As a local Chesterton, IN agent, Listing Leaders specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Chesterton, IN

4 Beds ⋅ 3 Baths

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

4 Beds ⋅ 3 Baths

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

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

4 Beds ⋅ 3 Baths

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

3 Beds ⋅ 3 Baths

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

3 Beds ⋅ 3 Baths

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

4 Beds ⋅ 3 Baths

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

4 Beds ⋅ 3 Baths

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

3 Beds ⋅ 3 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 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

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

3 Beds ⋅ 3 Baths

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

3 Beds ⋅ 2 Baths

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

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