Real Estate Investment Properties for Sale in Chesterton, IN

Looking for investment property in Chesterton, IN with high ROI ?

Explore a variety of short-term homes & houses in Chesterton, IN. Invest wisely with VRBO & Chesterton, IN Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Golden Highlands Investment Property for Sale in Chesterton, IN

Search for Golden Highlands Investment Property for Sale in Chesterton, Indiana. Browse all of Mashvisor’s Golden Highlands Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 125 Golden Highlands Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1452 Gossett Mill Ave Chesterton, IN Welcome to this beautiful 2-story home in Chesterton, IN! Built in 2017, this 4 bedroom, 3...	4 beds \| 2 baths \| 2,031 sq.ft.	$444,900	Airbnb cash on cash: 2.24% Traditional cash on cash: 4.47% Airbnb Rental Income: $2464 Traditional Rental Income: $2794 Airbnb ROI: 2.24% Traditional ROI: 4.47%
1123 Waverly Rd Chesterton, IN Updated 2 Story 3 Bedroom 2 Bath Home located minutes from the Indiana Dunes National Lake...	3 beds \| 1 baths \| 2,184 sq.ft.	$339,900	Airbnb cash on cash: 0.21% Traditional cash on cash: 5.32% Airbnb Rental Income: $1152 Traditional Rental Income: $2402 Airbnb ROI: 0.21% Traditional ROI: 5.32%
2011 Timberwood Lane Chesterton, IN Step inside and fall in love! This Easton Park home delivers all the charm, function, and ...	4 beds \| 3 baths \| 2,476 sq.ft.	$539,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.78% Airbnb Rental Income: $2464 Traditional Rental Income: $3030 Airbnb ROI: 1.47% Traditional ROI: 3.78%
656 S 4th St Chesterton, IN Motivated seller! Completely remodeled home in a desirable location! Location is one of th...	3 beds \| 2 baths \| 1,542 sq.ft.	$335,000	Airbnb cash on cash: 0.78% Traditional cash on cash: 3.5% Airbnb Rental Income: $1152 Traditional Rental Income: $1625 Airbnb ROI: 0.78% Traditional ROI: 3.5%
2221 Easton Park Dr Chesterton, IN Hurry now to make your own selections! The ever-popular Melanie floor plan offers all of t...	4 beds \| 2 baths \| 2,348 sq.ft.	$549,900	Airbnb cash on cash: 1.57% Traditional cash on cash: 3.06% Airbnb Rental Income: $2464 Traditional Rental Income: $2630 Airbnb ROI: 1.57% Traditional ROI: 3.06%
1163 Burns Blvd Chesterton, IN Welcome to this charming half duplex in the Village of Burns Harbor, located within the hi...	4 beds \| 2 baths \| 2,594 sq.ft.	$314,500	Airbnb cash on cash: 4.79% Traditional cash on cash: 6.53% Airbnb Rental Income: $2716 Traditional Rental Income: $2589 Airbnb ROI: 4.79% Traditional ROI: 6.53%
801 Idlewild Ln Chesterton, IN Brand New & Move-In Ready! No Waiting, No Unfinished Details! Welcome to this beautifully ...	4 beds \| 3 baths \| 2,271 sq.ft.	$624,900	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.93% Airbnb Rental Income: $2464 Traditional Rental Income: $2891 Airbnb ROI: 1.17% Traditional ROI: 2.93%
2121 Tupelo Ln Chesterton, IN Move-in ready, maintenance-free main-floor condo with a 1-car garage! A bright, open-conce...	2 beds \| 1 baths \| 1,228 sq.ft.	$169,999	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.78% Airbnb Rental Income: $1311 Traditional Rental Income: $1499 Airbnb ROI: 1.11% Traditional ROI: 4.78%
2230 Redwood Ln Chesterton, IN UNDER CONSTRUCTION...COMPLETION DATE ESTIMATED MID APRIL 2026. The Acadia in Easton Park! ...	4 beds \| 2 baths \| 2,281 sq.ft.	$599,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 3.19% Airbnb Rental Income: $2464 Traditional Rental Income: $2932 Airbnb ROI: 1.28% Traditional ROI: 3.19%
2131 Pepperbush Avenue Chesterton, IN Move-In Ready in Westwood Manor - Chesterton's desired Subdivision! Nestled in the award-w...	4 beds \| 4 baths \| 2,992 sq.ft.	$419,999	Airbnb cash on cash: 2.61% Traditional cash on cash: 6.23% Airbnb Rental Income: $2464 Traditional Rental Income: $3291 Airbnb ROI: 2.61% Traditional ROI: 6.23%
706 Idlewild Lane Chesterton, IN Welcome to Easton Park! The popular Michael floor plan offers all of the spaces that you n...	4 beds \| 3 baths \| 2,472 sq.ft.	$580,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.41% Airbnb Rental Income: $2464 Traditional Rental Income: $2419 Airbnb ROI: 1.39% Traditional ROI: 2.41%
1700 Littler Drive Chesterton, IN Experience Unparalleled Luxury in This 17,178 Sq. Ft. Sand Creek Estate Sophistication, cr...	5 beds \| 10 baths \| 17,178 sq.ft.	$2,500,000	Airbnb cash on cash: -2.09% Traditional cash on cash: -0.19% Airbnb Rental Income: $2433 Traditional Rental Income: $6257 Airbnb ROI: -2.09% Traditional ROI: -0.19%
613 Idlewild Lane Chesterton, IN You're going to love the Charlie ranch floor plan! Upon entrance you'll be in awe of the g...	3 beds \| 3 baths \| 2,208 sq.ft.	$597,377	Airbnb cash on cash: -0.66% Traditional cash on cash: 3.03% Airbnb Rental Income: $1152 Traditional Rental Income: $2830 Airbnb ROI: -0.66% Traditional ROI: 3.03%
1198 N Babcock Rd Chesterton, IN Escape to your own 1.7-acre private retreat just minutes from Lake Michigan and the Indian...	2 beds \| 1 baths \| 1,860 sq.ft.	$230,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 6.01% Airbnb Rental Income: $1311 Traditional Rental Income: $1780 Airbnb ROI: 1.98% Traditional ROI: 6.01%
810 Ashwood Lane Chesterton, IN Introducing the expanded Michelle floor plan-now offering 2 master suites-perfect for rela...	5 beds \| 4 baths \| 2,554 sq.ft.	$622,600	Airbnb cash on cash: 1.16% Traditional cash on cash: 3.44% Airbnb Rental Income: $2433 Traditional Rental Income: $3162 Airbnb ROI: 1.16% Traditional ROI: 3.44%
1251 N Mineral Springs Rd Chesterton, IN Welcome to your dream retreat! This all-brick, one-owner home sits on 6 spacious acres and...	3 beds \| 2 baths \| 2,617 sq.ft.	$749,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 1.86% Airbnb Rental Income: $1532 Traditional Rental Income: $2748 Airbnb ROI: -0.52% Traditional ROI: 1.86%
2215 Easton Park Drive Chesterton, IN Construction beginning September-completion February 2026! Introducing The Carmela floor p...	4 beds \| 3 baths \| 2,241 sq.ft.	$529,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 2.37% Airbnb Rental Income: $2464 Traditional Rental Income: $2201 Airbnb ROI: 1.7% Traditional ROI: 2.37%
498 Magnolia Lane Chesterton, IN Weclome to the maintenance-free lifestyle! Nestled amongst the serene nature preserve, the...	3 beds \| 2 baths \| 1,710 sq.ft.	$492,800	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.15% Airbnb Rental Income: $1152 Traditional Rental Income: $2394 Airbnb ROI: -0.37% Traditional ROI: 3.15%
1125 In-49 Chesterton, IN Unbeatable Location Near the Stunning Shores and Trails of the Indiana Dunes National Park...	3 beds \| 1 baths \| 1,472 sq.ft.	$259,900	Airbnb cash on cash: 1.48% Traditional cash on cash: 4.54% Airbnb Rental Income: $1152 Traditional Rental Income: $1521 Airbnb ROI: 1.48% Traditional ROI: 4.54%
103 Michigan St Chesterton, IN Completely remodeled 3-bedroom, 1.5 bath home in the heart of Porter, just minutes from La...	3 beds \| 1 baths \| 1,560 sq.ft.	$314,900	Airbnb cash on cash: 0.79% Traditional cash on cash: 4.14% Airbnb Rental Income: $1152 Traditional Rental Income: $1763 Airbnb ROI: 0.79% Traditional ROI: 4.14%
1995 Texas Street Chesterton, IN Welcome to this well-maintained one-level 3-bedroom, 1.5-bath half duplex in the Parkview ...	3 beds \| 2 baths \| 1,602 sq.ft.	$253,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 4.66% Airbnb Rental Income: $1152 Traditional Rental Income: $1873 Airbnb ROI: 0.05% Traditional ROI: 4.66%
1040 Kilarney Rd Chesterton, IN Buyers won't believe the endless opportunities and space in this home! A stunning corner l...	5 beds \| 5 baths \| 7,047 sq.ft.	$974,900	Airbnb cash on cash: -0.11% Traditional cash on cash: 3.31% Airbnb Rental Income: $2433 Traditional Rental Income: $4936 Airbnb ROI: -0.11% Traditional ROI: 3.31%
1240 Ryder Rd Chesterton, IN Perfectly positioned along the fairway in the gated Sand Creek community, this impressive ...	5 beds \| 4 baths \| 7,084 sq.ft.	$1,289,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 3.8% Airbnb Rental Income: $2433 Traditional Rental Income: $7051 Airbnb ROI: -0.55% Traditional ROI: 3.8%
270 Woodlawn Ave Chesterton, IN Welcome to 270 Woodlawn Ave in Chesterton. This beautifully remodeled 3-bedroom home offer...	3 beds \| 1 baths \| 1,183 sq.ft.	$249,900	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.11% Airbnb Rental Income: $1152 Traditional Rental Income: $1432 Airbnb ROI: 1.31% Traditional ROI: 4.11%
2152 Redwood Ln Chesterton, IN Construction beginning March 2026-ready for move-in late summer! Introducing The Carmela f...	4 beds \| 2 baths \| 2,241 sq.ft.	$529,900	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.43% Airbnb Rental Income: $2464 Traditional Rental Income: $2725 Airbnb ROI: 1.7% Traditional ROI: 3.43%
2316 Redwood Ln Chesterton, IN Enjoy the maintenance-free lifestyle in the newest phase of Easton Park-a quiet retreat lo...	3 beds \| 2 baths \| 1,676 sq.ft.	$459,900	Airbnb cash on cash: -0.79% Traditional cash on cash: 2.3% Airbnb Rental Income: $1152 Traditional Rental Income: $2098 Airbnb ROI: -0.79% Traditional ROI: 2.3%
0-2 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Experience the PAXTON model the perfect blend of space, style, a...	5 beds \| 5 baths \| 4,398 sq.ft.	$1,245,000	Airbnb cash on cash: 0.5% Traditional cash on cash: 3.21% Airbnb Rental Income: $2433 Traditional Rental Income: $4969 Airbnb ROI: 0.5% Traditional ROI: 3.21%
0-1 E 1050 N Chesterton, IN PROPOSED CONSTRUCTION Introducing The Ozark Ranch, a thoughtfully designed proposed c...	3 beds \| 3 baths \| 2,446 sq.ft.	$849,500	Airbnb cash on cash: -0.16% Traditional cash on cash: 2.4% Airbnb Rental Income: $1152 Traditional Rental Income: $2794 Airbnb ROI: -0.16% Traditional ROI: 2.4%
529 Windridge Dr Chesterton, IN Beautifully updated two story home tucked into a quiet cul de sac in one of Chesterton's m...	4 beds \| 3 baths \| 3,346 sq.ft.	$449,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 6.27% Airbnb Rental Income: $2464 Traditional Rental Income: $3518 Airbnb ROI: 2.33% Traditional ROI: 6.27%
1510 Ash Street Chesterton, IN Welcome to this beautifully maintained 3-bedroom, 2 full bathroom home in pristine conditi...	3 beds \| 2 baths \| 1,632 sq.ft.	$325,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 4.49% Airbnb Rental Income: $1152 Traditional Rental Income: $2060 Airbnb ROI: 0.27% Traditional ROI: 4.49%
2323 Legend Circle E Chesterton, IN Lovely maintenance free living in Chesterton's Coffee Creek! This well thought out floorpl...	3 beds \| 3 baths \| 2,607 sq.ft.	$475,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 4.25% Airbnb Rental Income: $1152 Traditional Rental Income: $2731 Airbnb ROI: -0.16% Traditional ROI: 4.25%
901 Bernie Court Chesterton, IN Charming 3-bedroom, 3-bathroom home in the Duneland School District sits on a serene 1.2-a...	3 beds \| 3 baths \| 1,959 sq.ft.	$399,999	Airbnb cash on cash: 0.17% Traditional cash on cash: 4.73% Airbnb Rental Income: $1152 Traditional Rental Income: $2483 Airbnb ROI: 0.17% Traditional ROI: 4.73%
1031 N 350 E Chesterton, IN Country Living Meets Modern Comfort. The perfect blend of peace, privacy, and premium amen...	3 beds \| 2 baths \| 2,100 sq.ft.	$460,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 3.58% Airbnb Rental Income: $1152 Traditional Rental Income: $2299 Airbnb ROI: 0.03% Traditional ROI: 3.58%
1040 Preserve Ln Chesterton, IN Located in The Preserve in Chesterton, this thoughtfully upgraded home offers comfort, eff...	4 beds \| 2 baths \| 2,312 sq.ft.	$459,900	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.77% Airbnb Rental Income: $2464 Traditional Rental Income: $2862 Airbnb ROI: 2.45% Traditional ROI: 4.77%
494 Magnolia Lane Chesterton, IN Last wooded homesite in Phase 2 of the villas in Easton Park! The newest phase of Easton P...	3 beds \| 2 baths \| 1,590 sq.ft.	$464,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 3.01% Airbnb Rental Income: $1152 Traditional Rental Income: $2206 Airbnb ROI: -0.28% Traditional ROI: 3.01%
2017 Wildwood Ct Chesterton, IN Style & grace refined in this magnificently outfitted home in Chesterton's Easton Park. Th...	3 beds \| 2 baths \| 2,866 sq.ft.	$700,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 2.4% Airbnb Rental Income: $1152 Traditional Rental Income: $2946 Airbnb ROI: -0.93% Traditional ROI: 2.4%
893 Pearson Road Chesterton, IN Set on over 3.5 acres, this beautifully maintained 3,000 square foot home offers the space...	4 beds \| 3 baths \| 2,912 sq.ft.	$499,000	Airbnb cash on cash: 1.77% Traditional cash on cash: 3.89% Airbnb Rental Income: $2464 Traditional Rental Income: $2856 Airbnb ROI: 1.77% Traditional ROI: 3.89%
708 Idlewild Lane Chesterton, IN Hurry now to choose your own selections on the show-stopping Allison floor plan that inclu...	4 beds \| 3 baths \| 2,415 sq.ft.	$569,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 3.23% Airbnb Rental Income: $2464 Traditional Rental Income: $2819 Airbnb ROI: 1.44% Traditional ROI: 3.23%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Chesterton, IN

1452 Gossett Mill Ave

Chesterton, IN

4 beds | 2 baths | 2,031 sq.ft.

$444,900

Airbnb cash on cash: 2.24%

Traditional cash on cash: 4.47%

Airbnb Rental Income: $2464

Traditional Rental Income: $2794

Airbnb ROI: 2.24%

Traditional ROI: 4.47%

1123 Waverly Rd

Chesterton, IN

3 beds | 1 baths | 2,184 sq.ft.

$339,900

Airbnb cash on cash: 0.21%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $1152

Traditional Rental Income: $2402

Airbnb ROI: 0.21%

Traditional ROI: 5.32%

2011 Timberwood Lane

Chesterton, IN

4 beds | 3 baths | 2,476 sq.ft.

$539,900

Airbnb cash on cash: 1.47%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $2464

Traditional Rental Income: $3030

Airbnb ROI: 1.47%

Traditional ROI: 3.78%

656 S 4th St

Chesterton, IN

3 beds | 2 baths | 1,542 sq.ft.

$335,000

Airbnb cash on cash: 0.78%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $1152

Traditional Rental Income: $1625

Airbnb ROI: 0.78%

Traditional ROI: 3.5%

2221 Easton Park Dr

Chesterton, IN

4 beds | 2 baths | 2,348 sq.ft.

$549,900

Airbnb cash on cash: 1.57%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $2464

Traditional Rental Income: $2630

Airbnb ROI: 1.57%

Traditional ROI: 3.06%

1163 Burns Blvd

Chesterton, IN

4 beds | 2 baths | 2,594 sq.ft.

$314,500

Airbnb cash on cash: 4.79%

Traditional cash on cash: 6.53%

Airbnb Rental Income: $2716

Traditional Rental Income: $2589

Airbnb ROI: 4.79%

Traditional ROI: 6.53%

801 Idlewild Ln

Chesterton, IN

4 beds | 3 baths | 2,271 sq.ft.

$624,900

Airbnb cash on cash: 1.17%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $2464

Traditional Rental Income: $2891

Airbnb ROI: 1.17%

Traditional ROI: 2.93%

2121 Tupelo Ln

Chesterton, IN

2 beds | 1 baths | 1,228 sq.ft.

$169,999

Airbnb cash on cash: 1.11%

Traditional cash on cash: 4.78%

Airbnb Rental Income: $1311

Traditional Rental Income: $1499

Airbnb ROI: 1.11%