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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 ⋅ 4 Baths

Perfectly positioned along the fairways of Sand Creek Country Club, this beautifully updated 4-bedroom, 3.5-bath home offers timeless design, modern improvements, and exceptional golf course views. A grand foyer welcomes you into a thoughtfully designed floor plan featuring a private home office, formal dining room, and inviting living room anchored by a cozy fireplace and expansive windows overlooking the course. The remodeled kitchen is the heart of the home, showcasing quartz countertops, custom cabinetry, stainless steel appliances, a generous center island, subway tile backsplash, and a bright breakfast area that flows effortlessly into the spectacular sunroom. Bathed in natural light from soaring windows and skylights, this versatile space offers panoramic views of the backyard and golf course, making it the perfect place to relax or entertain year-round. The spacious primary suite provides a peaceful retreat with two walk-in closets and a beautifully renovated spa-inspired bath featuring a custom tiled walk-in shower, infrared sauna, and premium finishes. Upstairs, you'll find three generously sized bedrooms, including a private en-suite and a Jack-and-Jill bath, providing comfort and privacy for family and guests alike. An unfinished basement offers endless possibilities for future living space, fitness, recreation, or storage. Outside, enjoy the beautifully landscaped yard, expansive deck, and picturesque setting overlooking one of Indiana's premier golf communities. With quality updates throughout, generous living spaces, and an unbeatable location in the Sand Creek Subdivision, this is a rare opportunity to enjoy refined golf course living while having easy access to Chicago, The Dunes, Lake Michigan and more!

1591 Hogan Avenue, Chesterton

3 Beds ⋅ 1 Baths

This adorable 3 bedroom one bath home is ready for new owners. Kitchen has been updated. Quartz counter top with stainless steel sink and appliances. 1.5 car garage and storage shed as well. Yard is fenced. Duneland schools.

1025 W Porter Avenue, Chesterton

3 Beds ⋅ 2 Baths

LUXURY MEETS NATURE in this exceptional 3 bedroom, 2 bath ranch, perfectly nestled on a .92 acre wooded lot! This custom built home offers an open-concept design with soaring vaulted ceilings in the kitchen, dining, and living areas. Every detail was thoughtfully designed for comfort, including polished concrete floors with radiant in-floor heat throughout the home. The beautifully appointed kitchen features granite countertops, soft-close cabinery and energy efficient appliances. The primary suite includes direct patio access, a walk-in closet and a spa inspired bath. Two additional bedrooms offer flexibility for guests or a home office. A convenient utility room includes a stackable washer and dryer and an Energy Star rated combi boiler, offering efficiency and year round comfort. The oversized 2 car garage is eqipped with insulated walls and doors, keyless entry and pull-down attic access for abundant storage. Relax on the 15 x 12 covered patio and enjoy the peaceful wooded views. Prime Chesterton location, near the seasonal European and Farmer's Markets, the new YMCA Healthy Living Campus, shopping, dining, wineries, and Indiana Dunes. Experience the perfect balance of luxury, comfort and nature all in one exceptional home!

2645 W 1100 N, Chesterton

4 Beds ⋅ 4 Baths

First Time on the Market! Proudly offered by its original owner, this exceptional property presents a rare opportunity to own a private retreat nestled on 5 picturesque acres. You will notice quality craftsmanship & attention to detail throughout the home. Surrounded by mature trees and abundant wildlife, the property features a cleared walking trail, a dedicated hunting area, a cozy fire pit, an apple tree, and a peaceful setting you'll enjoy year-round. Designed for both everyday living and entertaining, the home offers 4 bedrooms and 4 bathrooms with generous living spaces throughout. The spacious eat-in kitchen includes a pantry, built-in space saver and room for the whole family to gather for meals. The oversized living room is highlighted by a beautiful wood-burning fireplace and a large sliding glass door that showcases the serene backdrop. Step outside onto the expansive deck overlooking the private backyard--an ideal space for morning coffee, evening sunsets, or just relaxing with friends and family. The primary suite features an updated 3/4 bath and ample closet space. Throughout the home you'll find numerous custom built-in storage solutions and spacious closets designed with organization and storage in mind. The finished lower level expands your living space with a massive family room centered around a second wood-burning fireplace, complete with a convenient exterior-access wood storage cabinet for easy restocking. The lower level also offers a spacious fourth bedroom, w/ a bonus room connected & a half bath. A full bathroom, laundry room, and a dedicated tool/workshop room, provide endless possibilities for hobbies, guests, or multi-generational living. Additional highlights include oversized 2 car garage, a metal storage shed, a buoy/storage shed. If you've been searching for privacy, nature, and a home that has been lovingly maintained by one owner, you'll want to see this one! Survey & original blueprints attached for added peace of mind.

1089 N 200 W, Chesterton

4 Beds ⋅ 5 Baths

Within the gated Sand Creek community, this beautiful custom residence blends timeless architecture with thoughtfully curated designer updates, creating a home that is both elegant and inviting. Rich hardwood flooring, extensive millwork, designer selected custom lighting, and refined finishes elevate every space while offering exceptional comfort. At the heart of the home, the fully renovated kitchen showcases custom cabinetry, quartz countertops, a designer tile backsplash, stainless steel appliances, combination microwave and double wall ovens, gas cooktop, and kitchen island. It flows seamlessly into the breakfast area, sunroom, formal dining room, and great room featuring exposed wood beams, custom built-ins, and a striking floor-to-ceiling stone fireplace, creating an open concept feel. The main-level primary suite is a true retreat with private access to the expansive deck and a stunning spa-inspired bath featuring a steam shower, oversized tile, dual sink vanity, premium fixtures, and an oversized walk-in shower with multiple shower heads along with a custom designed closet. Upstairs offers three spacious bedrooms, two full baths, and a large bonus room ideal for a home office or flexible living space. The finished daylight basement is designed for entertaining with a spacious family room, stone fireplace, custom wet bar, recreation area, full bath, and abundant storage. Outdoor living is equally impressive with an expansive deck, screened gazebo, hot tub, paver patio, mature landscaping, and irrigation system, creating a private setting for entertaining or relaxing. Additional highlights include finished three-car garage with custom storage and the close proximity to easily join Sand Creek Country Club for its exceptional amenities, including championship golf, swimming, fitness, tennis, dining, and year-round social events. Thoughtfully updated, timeless design and modern luxury, this exceptional home offers a lifestyle at an exceptional value!

1035 Kilarney Road, Chesterton

3 Beds ⋅ 3 Baths

Trade traffic for trailheads and design a home that completely reflects your soul. Tucked away on an expansive 2.03-acre wooded lot in Chesterton, this solid tri-level property is a dream canvas for the visionary buyer ready to bring a high-contrast, moody aesthetic to life. With 2,531 square feet, three bedrooms, and three bathrooms, plus a bonus room, the spacious layout features great architectural bones that practically beg for rich textures, deep color palettes, and a custom modern remodel. Location Highlights Outdoor Adventure: The Heron Rookery Trail and Dale B. Engquist Nature Preserve are practically at your doorstep. Spend your weekends exploring the Indiana Dunes State Park Nature Center or Coffee Creek Preserve. Top-Tier Education: Located within the highly desirable Duneland School Corporation boundaries. Easy Commuting: Enjoy the perfect balance of a secluded, peaceful retreat that is still highly connected--the Beverly Shores train station or by car is just a short drive away for effortless city trips. (approx. 40 minutes to the city). Outside, the massive yard is surrounded by trees, offering ultimate privacy for a stunning outdoor living area, a native garden, or quiet mornings listening to birdsong. Ample parking and a 2.5-car garage mean there's plenty of room for your weekend toys and guests. Opportunities that blend acreage, top schools, immediate trail access, and true renovation potential don't last long. Schedule your tour today. Home is being sold AS-IS.

397 E 1300 N, Chesterton

4 Beds ⋅ 2 Baths

Welcome to 3624 Fairway Drive in Chesterton's desirable Golfview Estates! Offering nearly 2,000 square feet of living space, this 4-bedroom, 2-bath quad-level home provides the room and flexibility today's buyers are looking for. The home's multi-level design creates distinct spaces for gathering, relaxing, entertaining, working from home, or simply spreading out. Step inside to vaulted ceilings, warm bamboo hardwood flooring, a welcoming fireplace, and multiple living areas filled with possibilities. Outside, the generously sized corner lot and expansive two-tier deck create an inviting setting for summer cookouts, entertaining friends and family, or enjoying a quiet evening at home. Beyond the property itself, you'll love everything this location has to offer. Golfview Estates features neighborhood walking opportunities, a playground and park, while nearby trails, the Indiana Dunes National Park, South Shore Line, shopping, dining, and major highways put recreation and everyday conveniences within easy reach. Commuters will also appreciate convenient access toward Chicago and the surrounding Northwest Indiana communities. Located within the Duneland School Corporation, 3624 Fairway Drive offers a wonderful combination of space, location, and versatility in an established Chesterton neighborhood. Come see the possibilities and imagine making this home your own!

3624 Fairway Drive, Chesterton

3 Beds ⋅ 3 Baths

Welcome to this beautifully maintained ranch home in the desirable community of Chesterton, now featuring a brand-new roof! This spacious residence offers 3 bedrooms, 3 bathrooms, and 3 inviting fireplaces, creating the perfect blend of comfort, warmth, and timeless charm. The thoughtfully designed floor plan provides generous living spaces ideal for both everyday living and entertaining guests. Enjoy the convenience of true single-level living while relaxing by one of the cozy fireplaces on cool Indiana evenings, and enjoy a nice hot soak in the new hot tub! Ideally situated just minutes from downtown Chesterton, parks, top-rated schools, shopping, restaurants, the South Shore Line, and major highways, this home offers exceptional accessibility for commuters and anyone looking to experience the best of Northwest Indiana. Don't miss your chance to own this wonderful home--schedule your private showing today!

117 Washington Avenue, Chesterton

3 Beds ⋅ 1 Baths

ENJOY PEACE, QUIET, & SERENITY from your charming 3-bedroom ranch with a detached 1.5-car garage plus off-street parking! This lovely home is set back, away from the roadway. Enjoy soothing, natural views from your back yard & screened porch. Set on a spacious landscaped lot next to a private wooded area, this unique home boasts low-maintenance exterior, spacious open living room/dining room combo (great for entertaining! And the master bedroom will accommodate your king-size bed)! Newer lighting; freshly painted in soft neutrals to match any decor! All appliances stay. Two storage sheds. Close to everything: lakes, parks, trails, shopping, restaurants! This well-maintained property is being sold as is. Schedule your showing today. Welcome home!

704 S 22nd Street, Chesterton

3 Beds ⋅ 3 Baths

Welcome to 1622 Port Cove Dr in Porter, Indiana -- a charming 3-bedroom, 3-bathroom tri-level home offering approximately 1,742 square feet of comfortable living space. This residence blends functionality and relaxation in a desirable neighborhood and is ready for some fresh updates. Homeowners are motivated to sell. Step inside to find a spacious and inviting layout. The tri-level design provides excellent separation of spaces: the main level features an eat-in kitchen and living areas perfect for everyday living and entertaining, while the upper level offers private bedroom retreats, including a main bedroom with its own ensuite bathroom. Three full bathrooms ensure convenience for everyone in the household. The highlight of this home is the fenced backyard oasis. Enjoy summer days on the large deck, cool off in the above-ground pool, or gather around the fire pit for evenings under the stars. With plenty of room to play or garden, this outdoor space is ready for memories. A 2-car garage adds practical convenience for parking and storage. Located in Porter, you're just minutes from the stunning Indiana Dunes National Park and State Park, with miles of beaches, hiking trails, and Lake Michigan views. The vibrant Chesterton area offers excellent amenities including shops, restaurants, schools, and easy access to major routes -- perfect for commuters while still providing a peaceful suburban feel. This tri-level home combines comfort, outdoor enjoyment, and unbeatable location. With motivated sellers and a home ready for your personal updates, don't miss your chance to make it yours!

1622 Port Cove Drive, Chesterton

5 Beds ⋅ 5 Baths

Highly desirable Sand Creek property!!!! Presenting this custom built, 5 bedroom, 4.5 bath home. The list of updates to this property are endless!!! New gourmet appliances, granite countertops, wood floors, carpet, new Spa like master bath, oversized heated 3 car garage, brand new finished basement, and the list goes on. Enjoy relaxing fireside at your secluded backyard oasis this home is an entertainer's dream!!!! Sand Creek is one of Northwest Indiana's premier gated subdivisions featuring 27-hole championship golf course, just steps from every amenity the country club has to offer. The Sand Creek lifestyle awaits you. Schedule your private tour today of this spectacular property within the gates of Sand Creek today!!!!!

1245 Kilarney Road, Chesterton

4 Beds ⋅ 5 Baths

Light, bright and thoughtfully designed, this custom-built brick home offers over 4,000 square feet of exceptional living space in the heart of Chesterton. The inviting main level showcases beautiful hardwood floors, a cozy fireplace an open concept living area, a separate den that could be turned into a fifth bedroom and a formal dining room. The well-appointed kitchen offers abundant cabinetry, a large pantry, center island and brand-new stove and refrigerator. Step outside to the lovely screened in porch and enjoy peaceful views of nature while listening to the birds sing. Upstairs, two bedrooms feature private en-suites while the remaining bedrooms share a convenient jack and jill bathroom. A hidden bonus room adds a touch of charm and creativity, offering the perfect space for a playroom, gaming room, office, craft room or additional den. The finished lower level is an entertainers dream, complete with a spacious rec room, pool table and wet bar. Major updates include a new roof in 2025, furnace and central air in 2022 and the peace of mind of a whole house generator. This one-of-a-kind property combines space, character, and functionality in a location you will love to call home.

543 Windridge Drive, Chesterton

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