Real Estate Investment Properties for Sale in Chester, MT

Looking for investment property in Chester, MT with high ROI ?

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

Investment Property for Sale in Chester, MT

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
310 3rd St E Chester, MT Tucked behind fragrant lilac bushes and mature caraganas that offer natural privacy, a cha...	2 beds \| 1 baths \| 740 sq.ft.	$155,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.1% Airbnb Rental Income: $null Traditional Rental Income: $1634 Airbnb ROI: N/A Traditional ROI: 9.1%
164 W. Main Street Chester, MT Nestled on 7.345 acres in the quiet community of Lothair, Montana, this unique property of...	4 beds \| 2 baths \| 1,460 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.7% Airbnb Rental Income: $null Traditional Rental Income: $1536 Airbnb ROI: N/A Traditional ROI: 2.7%
Investment Properties for Sale in Other Cities of Montana
20 Wood Ridge Drive Columbia Falls , MT Mountain lodge living in Big Sky Country! Discover the perfect blend of privacy, comfort, ...	3 beds \| 4 baths \| 4,299 sq.ft.	$1,950,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 0.3% Airbnb Rental Income: $3059 Traditional Rental Income: $3018 Airbnb ROI: -0.07% Traditional ROI: 0.3%
1141 Pin Avenue Bozeman , MT This 3 bedroom, 2 bath home has all the cozy charm you want and the updates you need. Buil...	3 beds \| 2 baths \| 1,712 sq.ft.	$655,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.72% Airbnb Rental Income: $null Traditional Rental Income: $2198 Airbnb ROI: N/A Traditional ROI: 1.72%
522 E Alkali Creek Road Billings , MT Experience the ultimate Montana lifestyle in this stunning custom rancher, where wildlife ...	4 beds \| 3 baths \| 2,667 sq.ft.	$565,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.59% Airbnb Rental Income: $null Traditional Rental Income: $2978 Airbnb ROI: N/A Traditional ROI: 3.59%
8373 Goldenstein Lane Bozeman , MT Bright, airy and full of life, this Southside gem has all you need to thrive in Bozeman, w...	N/A beds \| N/A baths \| N/A	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.18% Airbnb Rental Income: $null Traditional Rental Income: $5413 Airbnb ROI: N/A Traditional ROI: 4.18%
109 Eagle Bend Drive Bigfork , MT Welcome to this extensively remodeled 3BD/4BA 4,001 SF home by Ciao Interiors & George Gib...	3 beds \| 4 baths \| 4,001 sq.ft.	$1,750,000	Airbnb cash on cash: -0.29% Traditional cash on cash: 0.93% Airbnb Rental Income: $2243 Traditional Rental Income: $3668 Airbnb ROI: -0.29% Traditional ROI: 0.93%
550 Blacktail Heights Lakeside , MT Stunning top-of-the-mountain privacy and panoramas in nearly every direction including spe...	4 beds \| 5 baths \| 5,200 sq.ft.	$2,995,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.51% Airbnb Rental Income: $946 Traditional Rental Income: $5165 Airbnb ROI: -1.13% Traditional ROI: 0.51%
25802 Old Highway 93 Dayton , MT Welcome to your dream waterfront retreat! This immaculate 4,678 sq. ft. custom home is per...	4 beds \| 4 baths \| 4,678 sq.ft.	$5,750,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.36% Airbnb Rental Income: $null Traditional Rental Income: $4447 Airbnb ROI: N/A Traditional ROI: -0.36%
160 Old Us Highway 93 S Somers , MT Perched above Somers Bay with commanding views of Flathead Lake and the Swan Range, this r...	3 beds \| 2 baths \| 2,250 sq.ft.	$759,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 2.17% Airbnb Rental Income: $2085 Traditional Rental Income: $2641 Airbnb ROI: 0.63% Traditional ROI: 2.17%
236 Antigone Drive Hamilton , MT Just on the outskirts of Hamilton, this meticulously maintained home offers a perfect blen...	3 beds \| 2 baths \| 2,172 sq.ft.	$530,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.66% Airbnb Rental Income: $2350 Traditional Rental Income: $2648 Airbnb ROI: 1.89% Traditional ROI: 3.66%
2122 Lightning Draw Trail Victor , MT Charming Log Home With A Massive Price Improvement!!! This stunning 3-bedroom, 3-bathroom ...	3 beds \| 3 baths \| 2,652 sq.ft.	$915,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.16% Airbnb Rental Income: $1208 Traditional Rental Income: $2990 Airbnb ROI: -0.39% Traditional ROI: 2.16%
1051 E 6th Avenue Helena , MT This brick Victorian charmer is located just 1 block from the State Capitol building! The ...	N/A beds \| N/A baths \| N/A	$569,000	Airbnb cash on cash: -0.85% Traditional cash on cash: 0.9% Airbnb Rental Income: $932 Traditional Rental Income: $1515 Airbnb ROI: -0.85% Traditional ROI: 0.9%
883 Lupfer Road Whitefish , MT Spread over 3.7 acres, this ranch-style home offers terrific privacy paired with the conve...	3 beds \| 3 baths \| 1,512 sq.ft.	$925,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 3% Airbnb Rental Income: $2467 Traditional Rental Income: $3734 Airbnb ROI: 0.83% Traditional ROI: 3%
17 Weber Gulch Road Thompson Falls , MT Under the shade of towering pine trees sits this single level home. On a concrete slab wit...	2 beds \| 2 baths \| 1,787 sq.ft.	$529,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 0.63% Airbnb Rental Income: $1408 Traditional Rental Income: $959 Airbnb ROI: 0.69% Traditional ROI: 0.63%
3737 Corwin Street Bozeman , MT SELLER OFFERING A $20,000 BUYERS CHOICE IN CLOSING COSTS OR CREDITS AT CLOSING WITH ACCEPT...	4 beds \| 3 baths \| 3,328 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $2903 Airbnb ROI: N/A Traditional ROI: 1.8%
114 Braziel Lake Loop Helmville , MT Wow! If peace and privacy is what you are looking for this is it! 92.5 acres of gorgeous l...	3 beds \| 4 baths \| 2,292 sq.ft.	$1,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.39% Airbnb Rental Income: $null Traditional Rental Income: $3007 Airbnb ROI: N/A Traditional ROI: 1.39%

Real Estate investment in Chester, MT

There are 2 properties for sale in the city of Chester . The median list price in Chester is $210,000 and the average price per square foot is $138. In September 2025, the average monthly cash on cash return in Chester is 9.00%. The average monthly rental income in Chester is $1,634.

Chester, MT Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Chester.

The ROI for Short-Term is higher than the Long-Term in Chester with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Chester, MT

310 3rd St E

Chester, MT

2 beds | 1 baths | 740 sq.ft.

$155,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.1%

Airbnb Rental Income: $null

Traditional Rental Income: $1634

Airbnb ROI: N/A

Traditional ROI: 9.1%

164 W. Main Street

Chester, MT

4 beds | 2 baths | 1,460 sq.ft.

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.7%

Airbnb Rental Income: $null

Traditional Rental Income: $1536

Airbnb ROI: N/A

Traditional ROI: 2.7%

Investment Properties for Sale in Other Cities of Montana

Columbia Falls , MT

3 beds | 4 baths | 4,299 sq.ft.

$1,950,000

Airbnb cash on cash: -0.07%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $3059

Traditional Rental Income: $3018

Airbnb ROI: -0.07%

Traditional ROI: 0.3%

Bozeman , MT

3 beds | 2 baths | 1,712 sq.ft.

$655,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.72%

Airbnb Rental Income: $null

Traditional Rental Income: $2198

Airbnb ROI: N/A

Traditional ROI: 1.72%

Billings , MT

4 beds | 3 baths | 2,667 sq.ft.

$565,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.59%

Airbnb Rental Income: $null

Traditional Rental Income: $2978

Airbnb ROI: N/A

Traditional ROI: 3.59%

Bozeman , MT

N/A beds | N/A baths | N/A

$995,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.18%

Airbnb Rental Income: $null

Traditional Rental Income: $5413

Airbnb ROI: N/A

Traditional ROI: 4.18%

Bigfork , MT

3 beds | 4 baths | 4,001 sq.ft.

$1,750,000

Airbnb cash on cash: -0.29%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $2243

Traditional Rental Income: $3668

Airbnb ROI: -0.29%

Traditional ROI: 0.93%

Lakeside , MT

4 beds | 5 baths | 5,200 sq.ft.

$2,995,000

Airbnb cash on cash: -1.13%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $946

Traditional Rental Income: $5165

Airbnb ROI: -1.13%

Traditional ROI: 0.51%

Dayton , MT

4 beds | 4 baths | 4,678 sq.ft.

$5,750,000

Airbnb cash on cash: N/A