Chesterton, IN Homes for Sale

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  /24

  $439,000

  • 4 Beds
  • 3.5 Baths
  • 2,992 Sq Ft

  2131 Pepperbush Ave, Chesterton, IN 46304

  Desirable Westwood Manor Subdivision in Chesterton!Located in the award-winning Duneland School District, this meticulously maintained and move-in-ready home offers 4 bedrooms, 4 bathrooms, a loft office area, and a finished basement with a flex room that could serve as a 5th bedroom, office, or game room.The main level features a spacious eat-in kitchen with a generous pantry and sliding doors

  

  Jason Moon

  Trueblood Real Estate, LLC

  (219) 348-8090

  2131 Pepperbush Ave, Chesterton, IN 46304
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  /65

  $1,199,999

  • 6 Beds
  • 5.5 Baths
  • 7,047 Sq Ft

  1458 Spyglass Cir, Chesterton, IN 46304

  Exquisite Golf Course Estate in the Gated Sand Creek CommunityWelcome to luxury living in the prestigious, gated Sand Creek community. This custom-built home is perfectly positioned on the Tee Box of Lake Hole 1, offering panoramic golf course views and a short walk to the clubhouse and its upscale amenities.With over 7,000 square feet of timeless design, this 6-bedroom, 6-bath estate blends

  

  Jason Moon

  Trueblood Real Estate, LLC

  (219) 912-2020

  1458 Spyglass Cir, Chesterton, IN 46304
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  /46

  $599,000

  • 4 Beds
  • 3 Baths
  • 3,066 Sq Ft

  1650 Hogan Ave, Chesterton, IN 46304

  Located in the desirable Sand Creek community, this stunning 4-bedroom, 3-bath home seamlessly blends luxury, comfort, and modern updates. The home features LED lighting throughout, hardwood floors, crown molding, and a stone fireplace just five years old. The main floor and upper level both include convenient laundry areas, while the huge primary suite offers a tray ceiling, brand-new carpet,

  

  Paul Boyter

  McColly Real Estate

  (219) 342-2742

  1650 Hogan Ave, Chesterton, IN 46304
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  /29

  $294,900

  • 3 Beds
  • 2 Baths
  • 1,680 Sq Ft

  327 S 18th St, Chesterton, IN 46304

  Discover your dream home in Chesterton, just minutes from the scenic Indiana Dunes! This expansive tri-level residence boasts 3 generous bedrooms and 2 updated bathrooms. Enjoy two large living areas, perfect for entertaining or relaxing. The home features fresh flooring and new countertops throughout, adding a modern touch. Outside, a spacious fenced-in yard offers ample room for equipment

  

  Jeff McCormick

  McCormick Real Estate, Inc.

  (219) 506-3994

  327 S 18th St, Chesterton, IN 46304
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  /31

  $480,000

  • 4 Beds
  • 2.5 Baths
  • 2,261 Sq Ft

  544 Windridge Dr, Chesterton, IN 46304

  Welcome to your dream home in the heart of downtown Chesterton, Indiana! This spacious and custom-designed residence offers four bedrooms, two and a half baths, and a generous 2,261 square feet of luxury living space as well as an 1160 sq ft unfinished basement. Built with 2 x 6 construction, this home features impressive 9-foot ceilings throughout, with a soaring 11-foot ceiling in the family

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 946-4396

  544 Windridge Dr, Chesterton, IN 46304
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  /59

  $1,159,999

  • 3 Beds
  • 3 Baths
  • 4,964 Sq Ft

  1040 Country Creek Ln, Chesterton, IN 46304

  Make this detailed custom architect, designer, builders Lodge YOURS. Come home, relax, and enjoy every day. Experience the pleasure of true country living on this 4.46-acre retreat with a meandering creek, fruit trees, and fenced pasture. Each and every detail of this 5,000 sf country lodge smart home has been meticulously chosen, from the welcoming wrap-around porch and solid hickory front door,

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 544-5367

  1040 Country Creek Ln, Chesterton, IN 46304
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  /40

  $544,900

  • 4 Beds
  • 2.5 Baths
  • 2,444 Sq Ft

  2592 Ritter St, Chesterton, IN 46304

  WELCOME HOME to this Like New 2-Story Beauty! Ready and Waiting just for you to move right in! Set on a desirable corner lot towards the back of the subdivision, this home features 4 spacious bedrooms, 2.5 bathrooms, and a 3-Car garage equipped with an [TESLA Electric car charging dock]. A welcoming front porch ushers you into a grand foyer that leads to the stunning 2-story great room, complete

  

  David Taylor

  McColly Real Estate

  (219) 400-3758

  2592 Ritter St, Chesterton, IN 46304
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  /63

  $1,149,999

  • 3 Beds
  • 3.5 Baths
  • 5,608 Sq Ft

  1108 N 350 E, Chesterton, IN 46304

  Discover your dream retreat with this exquisite ranch home, perfectly situated on 10 ACRES of stunning natural beauty. This property includes a 3-bedroom, 3.5-bath layout that epitomizes modern comfort and country charm. As you explore the grounds, you'll find a huge, spring-fed pond that brings lots of wildlife, offering an idyllic setting for serene sunset views.Inside, the gourmet chef's

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 992-4187

  1108 N 350 E, Chesterton, IN 46304
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  /35

  $660,000

  • 8 Beds
  • 8 Baths
  • 2,512 Sq Ft

  103-117 Jeffrey St, Chesterton, IN 46304

  INCREDIBLE investment opportunity less than 1 hour from Chicago. Take a look at these fully rented and well maintained duplexes in the highly desirable town of Chesterton. Easy commute to I-94, Indiana Toll Road, and the South Shore Train line. A/C and Floors updated and these are turn-key rentals ready to start earning you revenue. Great possibility to grow your portfolio or live in one side

  

  Nick Scalise

  Listing Leaders

  (219) 327-8192

  103-117 Jeffrey St, Chesterton, IN 46304
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  /34

  $495,000

  • 6 Beds
  • 6 Baths
  • 1,884 Sq Ft

  106 Jeffrey St, Chesterton, IN 46304

  3 unit investment opportunity less than 1 hour from Chicago. Take a look at these fully rented and well maintained duplexes in the highly desirable town of Chesterton with Award winning Duneland Schools. Easy commute to I-94, Indiana Toll Road, and the South Shore Train line. A/C and Floors updated and these are turn-key rentals ready to start earning you revenue. Great possibility to grow your

  

  Nick Scalise

  Listing Leaders

  (219) 300-6812

  106 Jeffrey St, Chesterton, IN 46304
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  /28

  $375,000

  • 4 Beds
  • 2 Baths
  • 1,872 Sq Ft

  200 Ivy St, Chesterton, IN 46304

  Welcome to this beautifully fully renovated home in the heart of downtown Chesterton! Featuring two separate units with private entrances, this home is currently being enjoyed as a spacious single family residence with a versatile related living space on the lower level. Each level is equipped with its own furnace, air conditioning, and water heater, offering comfort and efficiency throughout.

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 336-0887

  200 Ivy St, Chesterton, IN 46304
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  /9

  $90,000

  • Land
  • 1.46 Acres
  • $61,644 per Acre

  000 Pinneys Ct, Chesterton, IN 46304

  Build your dream home on this rare 1.46 acre wooded corner lot with public utilities and the peaceful Coffee Creek running through the property. Located just a hop, skip, and a jump from everything Chesterton has to offer including the highly sought after Duneland School District, the charming downtown area and Dunes National Lakeshore! Whether you're heading to the city for work or play,

  

  Lisa Gaff

  White Hat Realty Group, LLC

  (219) 266-7620

  000 Pinneys Ct, Chesterton, IN 46304
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  /24

  $335,900

  • 4 Beds
  • 2.5 Baths
  • 2,148 Sq Ft

  606 S 18th St, Chesterton, IN 46304

  Endless Possibilities Await - Bring your creative vision to life in this 4-bedroom, 2.5-bath residence situated in the highly sought-after Duneland School District! This home offers a remarkable chance to infuse your personal style and complete any pending projects. With a touch of care, it can become the ideal family haven! Nestled on just under half an acre, the property features a private,

  Crystal Soliday @properties/Christie's Intl RE

  606 S 18th St, Chesterton, IN 46304
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  /29

  $429,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,393 Sq Ft

  24 Karner Blue Ct, Chesterton, IN 46034

  New construction home in The Preserve, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! Welcome home to over 2300 sq. ft. of open floor plan. The front entry greets guests and leads past a den, which will have French doors, and a powder bath, into a large great room, open to dining nook and kitchen. Dining

  

  Allen Edwin Homes

  Builder

  24 Karner Blue Ct, Chesterton, IN 46034
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  /21

  $414,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  26 Karner Blue Ct, Chesterton, IN 46304

  New construction home in The Preserve Indiana, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! With over 2,200 sq ft of living space this floorplan is sure to please with its convenience & style! The main floor welcomes into the foyer, with a convenient powder bath tucked away, and past a den that

  

  Allen Edwin Homes

  Builder

  26 Karner Blue Ct, Chesterton, IN 46304
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  /40

  $399,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  22 Karner Blue Ct, Chesterton, IN 46304

  New construction home in The Preserve Indiana, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! With over 2,200 sq ft of living space this floorplan is sure to please with its convenience & style! The main floor welcomes into the foyer, with a convenient powder bath tucked away, and past a den that

  

  Allen Edwin Homes

  Builder

  22 Karner Blue Ct, Chesterton, IN 46304
• 

  

  /21

  $390,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,276 Sq Ft

  Integrity 2280 Plan at The Preserve Indiana, Chesterton, IN

  The Integrity 2280 is a traditional 2-story floor plan with a footprint designed for optimal and inclusive living & storage.

  

  Allen Edwin Homes

  Builder

  0 the Preserve Indiana St Unit 36494274, Chesterton, IN
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  /12

  $400,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,246 Sq Ft

  Elements 2200 Plan at The Preserve Indiana - Elements, Chesterton, IN

  The Elements 2200 is a traditional 2-story floor plan with a footprint designed for optimal and inclusive living & storage.

  

  Allen Edwin Homes

  Builder

  0 Elements St Unit 36474152, Chesterton, IN
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  /29

  $411,900 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,393 Sq Ft

  Elements 2390 Plan at The Preserve Indiana - Elements, Chesterton, IN

  The Elements 2390 is a traditional 2-story floor plan with a footprint designed for optimal and inclusive living & storage.

  

  Allen Edwin Homes

  Builder

  0 Elements St Unit 36474213, Chesterton, IN
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  /4

  $437,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  Elements 2700 Plan at The Preserve Indiana - Elements, Chesterton, IN

  The Elements 2700 is a traditional 2-story floor plan with a footprint designed for optimal and inclusive living & storage.

  

  Allen Edwin Homes

  Builder

  0 Elements St Unit 36503155, Chesterton, IN
• 

  $494,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,735 Sq Ft

  28 Karner Blue Ct, Chesterton, IN 46304

  New construction home in The Preserve, located in Duneland School Corp. RESNET energy smart construction will save owner over 1K yearly plus home has 10-year structural warranty! Welcome home, to over 2,700 sq. ft. of living space that seamlessly blends space with style. The large two-story foyer greets you and leads past a den or study continuing into the expansive great room and large dining

  

  Allen Edwin Homes

  Builder

  28 Karner Blue Ct, Chesterton, IN 46304
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  /23

  $199,900

  • Land
  • 12 Acres
  • $16,658 per Acre

  W 1000 N, Valparaiso, IN 46385

  12 Acre Vacant Land Lot Prime R1 Zoning Porter County, INDiscover the perfect blend of space, location, and opportunity with this expansive 12 acre parcel situated in the desirable R1 zoning districtideal for low-density, single-family residential development. Whether you're envisioning a private estate surrounded by nature or planning a thoughtfully designed subdivision, this property

  Heath Brunton

  W 1000 N, Valparaiso, IN 46385
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  /21

  $599,900

  • 3 Beds
  • 2 Baths
  • 2,417 Sq Ft

  359 E Burdick Rd, Chesterton, IN 46304

  Welcome home to this attractive, well maintained 3 BR/2BA Chalet style home in Jackson Township. This property features a detached garage with a 2 Bedroom upper level apartment that currently rents for 1,250 per month thru 9/30/25. The apartment has seperate utilities and it's own well and septic system. The home exterior boasts over 700 sq.ft. of decking, 4.35 acres of land and includes a

  Cheryl Bonin CHERYL Real Estate Services, L

  359 E Burdick Rd, Chesterton, IN 46304
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  /42

  $549,000

  • 4 Beds
  • 2.5 Baths
  • 2,476 Sq Ft

  2011 Timberwood Ln, Chesterton, IN 46304

  Step inside to discover light-toned engineered hardwood floors and upscale details throughout. The formal dining room is elevated with classic wainscoting, adding timeless charm to the contemporary design.At the heart of the home, the gourmet kitchen is a chef's dream--equipped with 42-inch upper cabinets, quartz countertops, roll-out shelving, and premium appliances. A spacious walk-in pantry

  Stefanie Neal BHHS Executive Group RE

  2011 Timberwood Ln, Chesterton, IN 46304
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  /13

  $529,900

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  2009 Timberwood Ln, Chesterton, IN 46304

  Come view this open concept ranch located in the highly sought after Easton Park subdivision. Upon entrance you are greeted with large vaulted ceilings, beautiful engineered wood floors and a stoned gas fireplace. Kitchen features vaulted ceilings, custom cabinetry with all quartz tops, oversized island, tile backsplash and all stainless steel appliances. Attached you will find the breakfast

  Jennifer Beauchamp Crown Executive Realty

  2009 Timberwood Ln, Chesterton, IN 46304
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  /54

  $650,000

  • 6 Beds
  • 3 Baths
  • 3,993 Sq Ft

  808 Waverly Rd, Chesterton, IN 46304

  The 1916 brick Craftsman home is an exquisite blend of historical charm and modern comfort. With five bedrooms and three bathrooms, it offers ample space for family living and entertaining guests. The entire home boasts original oak and walnut finishes, showcasing the craftsmanship and attention to detail typical of the era. These timeless features contribute to the home's warm and inviting

  Katie Kupsik Keller Williams Realty SWM

  808 Waverly Rd, Chesterton, IN 46304
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  /35

  $478,500

  • 9 Beds
  • 3.5 Baths
  • 4,200 Sq Ft

  501 Wabash Ave, Chesterton, IN 46304

  Right here, This Is The One! 501 Wabash Ave is a truly remarkableproperty in the heart of Chesterton, Indiana. Optionsabound...Generational living? Check. Income-producing property? Check.Beautiful open concept home with an apartment and guest suite forvisiting family and friends? Check. Boasting 4,200 square feet of livingspace, this property is as versatile as it is unique. The main area of

  Elizabeth Deutscher Listing Leaders

  501 Wabash Ave, Chesterton, IN 46304
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  /36

  $610,000

  • 4 Beds
  • 3 Baths
  • 3,269 Sq Ft

  263 E Paul Revere Ct, Chesterton, IN 46304

  Set on a full acre in one of Chesterton's most desirable neighborhoods--with no HOA--this 4-bed, 3-bath beauty offers over 3,200 square feet of well-planned living space, a 3-car garage and room to breathe both inside and out.Inside, you'll find the kind of layout buyers love: a sunlit living room with a two-sided fireplace that flows into a cozy family room with built-ins, a granite kitchen with

  Danek Znika Brokerworks Group

  263 E Paul Revere Ct, Chesterton, IN 46304
• 

  

  /31

  $489,900

  • 4 Beds
  • 2.5 Baths
  • 2,272 Sq Ft

  1471 Delos Marr Ave, Chesterton, IN 46304

  Completed in July 2017 by Oltof Homes this property offers 0.17 acres (7,541 sq. ft.) of space, including a lush lawn with professionally installed sod, a deck (added in 2018), and a pergola (installed in 2020) for outdoor relaxation. Inside, the 4-bedroom, 2.5-bathroom home features a thoughtfully designed open kitchen with high ceilings, high cabinets with molding, a marble countertop, and

  Ryan Peters StreetFront, LLC

  1471 Delos Marr Ave, Chesterton, IN 46304
• 

  

  /21

  $487,500

  • 4 Beds
  • 3.5 Baths
  • 3,917 Sq Ft

  378 Lake Vista Ct, Chesterton, IN 46304

  This home is priced to move. Sunlight floods this home which boasts 3,917 finished square feet of living space on a quiet cul-de-sac. Lake Pratt, a small lake for fishing is right outside the back yard of the home. The home site includes a wooded area that abuts a Shirley Heinz conservation area. The main floor primary bedroom with access to a full bathroom has views of the wooded area and

  Mary K. Kaczka RE/MAX Lifestyles

  378 Lake Vista Ct, Chesterton, IN 46304
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  /41

  $438,500

  • 4 Beds
  • 2 Baths
  • 2,450 Sq Ft

  333 Mount Jackson Ave, Chesterton, IN 46304

  Enjoy the best of both worlds on your one+ acre peaceful homestead in highly coveted Porter County! Centrally located, experience that country feel on a quiet wooded cul-de-sac just outside the outskirts of Valpo & Chesterton city limits! Possible related living in this spacious 4 bedroom brick & vinyl oasis with two separate living levels! Less than a 10-minute drive to Lake Michigan's sandy

  Lauren Defauw McColly Real Estate

  333 Mount Jackson Ave, Chesterton, IN 46304
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  /43

  $469,900

  • 4 Beds
  • 3 Baths
  • 3,382 Sq Ft

  4120 Abercrombie Dr, Chesterton, IN 46304

  SELLER IS MOTIVATED AND READY TO SELL!! Nestled in the desirable Abercrombie Woods, this stunning 1.5 story brick home offers a perfect blend of elegance and functionality. The kitchen, main floor bathrooms and the laundry room have been beautifully updated with new quartz countertops. Enjoy enhanced privacy with custom wood blinds throughout, and peace of mind with a Guardian backup generator.

  Kayla Jones Listing Leaders

  4120 Abercrombie Dr, Chesterton, IN 46304
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  /44

  $479,999

  • 3 Beds
  • 2 Baths
  • 1,827 Sq Ft

  2029 Timberwood Ln, Chesterton, IN 46304

  Step into this stunning 3-bedroom, 2-bath ranch home in the sought-after Easton Park subdivision of Chesterton. Built in 2021, this home offers all the benefits of new construction without the wait!Enjoy an open-concept design with vaulted ceilings, engineered hardwood floors, and a cozy gas fireplace in the living room. The custom kitchen is a chef's dream, featuring upgraded professional

  Jamie Crisman-Garcia Realty Executives Premier

  2029 Timberwood Ln, Chesterton, IN 46304
• 

  

  /20

  $449,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  499 Magnolia Ln, Chesterton, IN 46304

  New construction ranch home with a full basement-ready for your instant enjoyment! The newest phase of Easton Park is a quiet retreat located within minutes of award-winning schools, commuter expressways, and the IN Dunes National Lakeshore. The Zachary floor plan offers an almost 1,600 sq. ft. ranch floor plan plus a full basement! Upon entrance you'll find the expansive kitchen where you'll

  Michelle Renninger Better Homes and Gardens Real

  499 Magnolia Ln, Chesterton, IN 46304
• 

  /2

  $494,900 New Construction

  • 3 Beds
  • 2 Baths
  • 1,800 Sq Ft

  2420 Pradera Trail, Chesterton, IN 46304

  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

  Madison Young Brokerworks Group

  2420 Pradera Trail, Chesterton, IN 46304
• 

  

  /20

  $439,900 Open Sat 12PM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,590 Sq Ft

  2310 Redwood Ln, Chesterton, IN 46304

  New construction ranch home with a full basement-ready for your enjoyment June 2025! The newest phase of Easton Park is a quiet retreat located within minutes of award-winning schools, commuter expressways, and the IN Dunes National Lakeshore. The Zachary floor plan offers an almost 1,600 sq. ft. ranch floor plan plus a full basement! Upon entrance you'll find the expansive kitchen where

  Michelle Renninger Better Homes and Gardens Real

  2310 Redwood Ln, Chesterton, IN 46304
• 

  

  /21

  $459,900 Open Sat 12PM - 5PM

  • 3 Beds
  • 2 Baths
  • 1,710 Sq Ft

  490 Magnolia Ln, Chesterton, IN 46304

  Now building Easton Park Villa Homes Phase 2! The newest phase of Easton Park is a quiet retreat located within minutes of award-winning schools, commuter expressways, and the IN Dunes National Lakeshore. The brand new Gail floor plan offers 1,710 sq. ft. ranch floor plan plus a full basement, now with a relaxing covered rear patio! Upon entrance you'll find the expansive kitchen where you'll

  Michelle Renninger Better Homes and Gardens Real

  490 Magnolia Ln, Chesterton, IN 46304
• 

  

  /19

  $479,900 Open Sat 12PM - 5PM

  • 4 Beds
  • 2.5 Baths
  • 2,215 Sq Ft

  810 Idlewild Ln, Chesterton, IN 46385

  Now beginning construction-hurry to make your own custom selections! Completion August 2025! The Joey floor plan boasts 4 bedrooms, 2.5 baths and an unfinished basement for plenty of room to grow!. The charming front porch ushers you in to the foyer and flex room that's perfect for work or play needs! The kitchen offers an abundance of soft-close cabinetry with 42' uppers, center island, and

  Michelle Renninger Better Homes and Gardens Real

  810 Idlewild Ln, Chesterton, IN 46385
• 

  

  /52

  $925,000

  • 4 Beds
  • 3 Baths
  • 4,546 Sq Ft

  1116 N 350 E, Chesterton, IN 46304

  Welcome to this one-of-a-kind estate nestled on 10 serene acres in highly desirable Jackson Township. This exceptional property combines modern luxury, rustic elegance, and purpose-driven living, currently serving as both a private residence and a 501(c)(3) nonprofit animal rescue for abused, handicapped, and senior dogs. Whether you're seeking a private sanctuary, mini-farm, income property, or

  Jennifer Colvin Boulder Bay Realty Group

  1116 N 350 E, Chesterton, IN 46304
• 

  

  /31

  $300,000

  • 3 Beds
  • 2 Baths
  • 1,046 Sq Ft

  399 Conestoga Dr, Chesterton, IN 46304

  This charming 3-bedroom, 2-bathroom home in the conveniently located Olde Towne Subdivision is waiting for you! Step inside and be greeted by an open living area featuring vaulted ceilings and a cozy gas fireplace, perfect for relaxing evenings.The kitchen comes fully equipped with all appliances included, making your move-in seamless. Just off the back of the house, a lovely wood deck overlooks

  Vince Kisala Coldwell Banker Real Estate Gr

  399 Conestoga Dr, Chesterton, IN 46304

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