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!

3 Beds ⋅ 2 Baths

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

$875,000

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.

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

$699,000

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.

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

$859,900

This exceptional all-brick ranch offers over 4,200 finished square feet of thoughtfully designed living space. A traditional floor plan welcomes you with a gracious foyer, rich Cherry hardwood floors, and crown molding that flow throughout the main living areas. The library/office--originally designed as a third main-floor bedroom--offers flexibility for work or additional guest accommodations. Formal living with elegant fireplace and dining room with convenient service bar, create an inviting setting for entertaining. The kitchen is appointed with stainless steel appliances and an island workspace and opens seamlessly to the breakfast room with access to the screened porch and adjoining keeping room featuring a slanted ceiling and bay windows that fill the space with natural light. Privately situated on the opposite side of the home, the bedroom wing includes a spacious primary suite with tiled shower, dual vanities, and walk-in closet, along with a guest bedroom featuring its own full ensuite bath. The walk-out lower level expands the home's versatility with a large great room anchored by a double-sided fireplace, wet bar with granite countertops, family room, game room, private bedroom suite, and a dedicated workroom ideal for planting, painting, crafts, or woodworking. Completing the property are a two-car garage and separate golf cart garage, perfectly suited for an active lifestyle. Enjoy the ease of a low-maintenance lifestyle while retaining the spacious feel and individuality of a traditional residence. The association provides lawn care and fertilization, irrigation, snow removal, and maintenance of common areas--allowing more time to enjoy life and less time worrying about exterior upkeep.

3 Beds ⋅ 4 Baths

This exceptional all-brick ranch offers over 4,200 finished square feet of thoughtfully designed living space. A traditional floor plan welcomes you with a gracious foyer, rich Cherry hardwood floors, and crown molding that flow throughout the main living areas. The library/office--originally designed as a third main-floor bedroom--offers flexibility for work or additional guest accommodations. Formal living with elegant fireplace and dining room with convenient service bar, create an inviting setting for entertaining. The kitchen is appointed with stainless steel appliances and an island workspace and opens seamlessly to the breakfast room with access to the screened porch and adjoining keeping room featuring a slanted ceiling and bay windows that fill the space with natural light. Privately situated on the opposite side of the home, the bedroom wing includes a spacious primary suite with tiled shower, dual vanities, and walk-in closet, along with a guest bedroom featuring its own full ensuite bath. The walk-out lower level expands the home's versatility with a large great room anchored by a double-sided fireplace, wet bar with granite countertops, family room, game room, private bedroom suite, and a dedicated workroom ideal for planting, painting, crafts, or woodworking. Completing the property are a two-car garage and separate golf cart garage, perfectly suited for an active lifestyle. Enjoy the ease of a low-maintenance lifestyle while retaining the spacious feel and individuality of a traditional residence. The association provides lawn care and fertilization, irrigation, snow removal, and maintenance of common areas--allowing more time to enjoy life and less time worrying about exterior upkeep.

1340 Cantigny Court, Chesterton

$399,999

Looking for a place in Chesterton where you can actually breathe? This peaceful 2.2-acre country retreat offers the perfect balance of wide-open green space and a home designed for everyone to have their own corner. The main house features airy vaulted ceilings, a large country kitchen with stainless steel appliances, and oversized bedrooms with deep closets, plus extra attic storage in both garages. A standout feature is the clever "related living" setup: just close the French doors to create a fully private apartment complete with its own kitchen, laundry, and appliances. You can soak up the views year-round from the heated sunroom, which overlooks an above-ground pool with a wrap-around sun deck, or choose between the large party-sized fire pit and the smaller, cozy one for quieter nights. To top it all off, the property includes a massive 40' x 60' fully insulated pole barn with concrete floors, electric, and even a built-in bedroom and bathroom. With double barn doors and a drive-through exit for easy rear parking, this is the ultimate setup for hobbies, guests, or just enjoying the quiet life. Located in the award-winning Chesterton/Duneland School District, convenient to all major highways, don't wait - schedule your showing today!

3 Beds ⋅ 2 Baths

Looking for a place in Chesterton where you can actually breathe? This peaceful 2.2-acre country retreat offers the perfect balance of wide-open green space and a home designed for everyone to have their own corner. The main house features airy vaulted ceilings, a large country kitchen with stainless steel appliances, and oversized bedrooms with deep closets, plus extra attic storage in both garages. A standout feature is the clever "related living" setup: just close the French doors to create a fully private apartment complete with its own kitchen, laundry, and appliances. You can soak up the views year-round from the heated sunroom, which overlooks an above-ground pool with a wrap-around sun deck, or choose between the large party-sized fire pit and the smaller, cozy one for quieter nights. To top it all off, the property includes a massive 40' x 60' fully insulated pole barn with concrete floors, electric, and even a built-in bedroom and bathroom. With double barn doors and a drive-through exit for easy rear parking, this is the ultimate setup for hobbies, guests, or just enjoying the quiet life. Located in the award-winning Chesterton/Duneland School District, convenient to all major highways, don't wait - schedule your showing today!

141 W 900 N, Chesterton

$899,999

The sought-after Madeleine Model is now available and MOVE IN READY! One of our most desirable floorplans and on one of the largest lots of the community, this home combines thoughtful design with high-end finishes throughout. Step inside to a grand foyer with wainscoting and stunning two-story views. The main level offers a private primary suite, tucked away from the main living areas, complete with a spa-inspired ensuite featuring a soaking tub, tiled shower, dual vanity, and a walk-in closet with customized storage. The open-concept great room boasts 11-foot ceilings, a cozy gas fireplace, and access to the expansive 20x16 covered patio--perfect for entertaining. At the heart of the home, the chef's kitchen showcases an oversized island, wine and coffee bar, upgraded stainless steel Frigidaire Professional appliances, built-in gas cooktop with custom wood range hood, double wall ovens, ceiling-height backsplash, and a spacious walk-in pantry. Upstairs, find two additional bedrooms, a loft, and an oversized bonus room. Throughout the home you'll notice luxury upgrades like engineered hardwood, Delta faucets, Quorum lighting, custom wall accents, and oversized 7 A1/4' baseboards. Additional features include: Main floor laundry with drop zone off the 3-car garage Full unfinished basement with 9-ft ceilings, ready to expand This home blends style, function, and comfort at every turn!

4 Beds ⋅ 3 Baths

The sought-after Madeleine Model is now available and MOVE IN READY! One of our most desirable floorplans and on one of the largest lots of the community, this home combines thoughtful design with high-end finishes throughout. Step inside to a grand foyer with wainscoting and stunning two-story views. The main level offers a private primary suite, tucked away from the main living areas, complete with a spa-inspired ensuite featuring a soaking tub, tiled shower, dual vanity, and a walk-in closet with customized storage. The open-concept great room boasts 11-foot ceilings, a cozy gas fireplace, and access to the expansive 20x16 covered patio--perfect for entertaining. At the heart of the home, the chef's kitchen showcases an oversized island, wine and coffee bar, upgraded stainless steel Frigidaire Professional appliances, built-in gas cooktop with custom wood range hood, double wall ovens, ceiling-height backsplash, and a spacious walk-in pantry. Upstairs, find two additional bedrooms, a loft, and an oversized bonus room. Throughout the home you'll notice luxury upgrades like engineered hardwood, Delta faucets, Quorum lighting, custom wall accents, and oversized 7 A1/4' baseboards. Additional features include: Main floor laundry with drop zone off the 3-car garage Full unfinished basement with 9-ft ceilings, ready to expand This home blends style, function, and comfort at every turn!

2179 W 1100 N, Chesterton

$689,000

Style & grace refined in this magnificently outfitted home in Chesterton's Easton Park. The custom wainscotting, the wide plank engineered hardwood, the tasteful cabinet finishes adorned by quartz countertops, and the light fixtures all speak to timeless natural warmth, comfort and quality. French doors lead to front den with beautifully-crafted waffle ceiling. Generous windows throughout the home, providing brilliant light especially in the living room, with built-in shelving and cabinets surrounding a safe touch electric fireplace with elegant crown moulding mantle. High end remote control blinds, with auto end of day closure. Stainless appliances stay in the well apportioned kitchen, including the 5 burner gas range. Upstairs find wood floors, starting with the loft with rich wainscotting. Next are 3 bedrooms, anchored by the primary suite with stylish & symmetrical wainscotting, tile shower with glass doors, soaker tub, twin vanities, and smart room-sized walk-in closet. Giant laundry room with laundry sink, thoughtful and generous cabinets and counters with backsplash, and front loaders that stay. Finished basement with Rec Room serves the purpose as play, escape, or workout zone. Zoned HVAC has sanitizing ultraviolet light plus humidifier. WHOLE HOUSE generator, oversized with 28 kw. RO in kitchen. Epoxy garage floor. One of the larger, more private yards with southern exposure and well-placed mature shade trees.

3 Beds ⋅ 3 Baths

Style & grace refined in this magnificently outfitted home in Chesterton's Easton Park. The custom wainscotting, the wide plank engineered hardwood, the tasteful cabinet finishes adorned by quartz countertops, and the light fixtures all speak to timeless natural warmth, comfort and quality. French doors lead to front den with beautifully-crafted waffle ceiling. Generous windows throughout the home, providing brilliant light especially in the living room, with built-in shelving and cabinets surrounding a safe touch electric fireplace with elegant crown moulding mantle. High end remote control blinds, with auto end of day closure. Stainless appliances stay in the well apportioned kitchen, including the 5 burner gas range. Upstairs find wood floors, starting with the loft with rich wainscotting. Next are 3 bedrooms, anchored by the primary suite with stylish & symmetrical wainscotting, tile shower with glass doors, soaker tub, twin vanities, and smart room-sized walk-in closet. Giant laundry room with laundry sink, thoughtful and generous cabinets and counters with backsplash, and front loaders that stay. Finished basement with Rec Room serves the purpose as play, escape, or workout zone. Zoned HVAC has sanitizing ultraviolet light plus humidifier. WHOLE HOUSE generator, oversized with 28 kw. RO in kitchen. Epoxy garage floor. One of the larger, more private yards with southern exposure and well-placed mature shade trees.

2017 Wildwood Court, Chesterton

$1,199,900

Perfectly positioned along the fairway in the gated Sand Creek community, this impressive custom residence blends grand scale living with thoughtful design and exceptional versatility. From the moment you enter, a dramatic two-story foyer sets the tone, opening to inviting living spaces and a sweeping catwalk overlooking the heart of the home. The two-story great room is anchored by a striking stone fireplace and windows framing picturesque golf course views. Designed for gathering, the kitchen offers premium appliances, a center island, walk-in pantry, and butler's pantry, all seamlessly connected to casual dining and living areas. Dual staircases provide both functionality and architectural interest throughout the home. The main-level primary suite offers a private retreat complete with a spa-inspired bath, steam shower, soaking tub, dual vanities, and walk-in closets. A home office or study with French doors is also located on the main. Upstairs, 3 spacious bedrooms each feature access to full baths, while a large bonus room offers endless possibilities as an additional bedroom, playroom, media lounge, creative studio, home office, fitness area, or hobby space -- truly adaptable to fit your lifestyle. Outdoor living shines with a 900-sq ft deck overlooking the large backyard and sweeping fairway views, creating the perfect setting for entertaining or quiet evenings at home. The finished daylight basement is designed with entertainment in mind, featuring a large recreation area, custom bar, theatre room, and hidden rooms cleverly tucked behind built-in shelving for a unique and memorable experience. The basement easily functions as a guest retreat or extended living quarters. Additional highlights include a heated 3-car garage, abundant storage throughout, and incredible flexibility to create anything you desire for your new home. Experience elevated living-where grand entertaining, everyday comfort, and breathtaking views create a truly unforgettable home.

5 Beds ⋅ 6 Baths

Perfectly positioned along the fairway in the gated Sand Creek community, this impressive custom residence blends grand scale living with thoughtful design and exceptional versatility. From the moment you enter, a dramatic two-story foyer sets the tone, opening to inviting living spaces and a sweeping catwalk overlooking the heart of the home. The two-story great room is anchored by a striking stone fireplace and windows framing picturesque golf course views. Designed for gathering, the kitchen offers premium appliances, a center island, walk-in pantry, and butler's pantry, all seamlessly connected to casual dining and living areas. Dual staircases provide both functionality and architectural interest throughout the home. The main-level primary suite offers a private retreat complete with a spa-inspired bath, steam shower, soaking tub, dual vanities, and walk-in closets. A home office or study with French doors is also located on the main. Upstairs, 3 spacious bedrooms each feature access to full baths, while a large bonus room offers endless possibilities as an additional bedroom, playroom, media lounge, creative studio, home office, fitness area, or hobby space -- truly adaptable to fit your lifestyle. Outdoor living shines with a 900-sq ft deck overlooking the large backyard and sweeping fairway views, creating the perfect setting for entertaining or quiet evenings at home. The finished daylight basement is designed with entertainment in mind, featuring a large recreation area, custom bar, theatre room, and hidden rooms cleverly tucked behind built-in shelving for a unique and memorable experience. The basement easily functions as a guest retreat or extended living quarters. Additional highlights include a heated 3-car garage, abundant storage throughout, and incredible flexibility to create anything you desire for your new home. Experience elevated living-where grand entertaining, everyday comfort, and breathtaking views create a truly unforgettable home.

1240 Ryder Road, Chesterton

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