Real Estate Investment Properties for Sale in Oregon, WI

Looking for investment property in Oregon, WI with high ROI ?

Explore a variety of short-term homes & houses in Oregon, WI. Invest wisely with VRBO & Oregon, WI 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 Oregon, WI

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
829 Foxfield Rd Oregon, WI Beautiful home on 1/2-acre lot in desirable Autumn Woods Fairway Estates! Open layout idea...	4 beds \| 3 baths \| 3,000 sq.ft.	$615,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 3.01% Airbnb Rental Income: $4275 Traditional Rental Income: $3165 Airbnb ROI: 3.37% Traditional ROI: 3.01%
195 Prairie Mound Dr Oregon, WI Welcome home to this bright and inviting 4-bedroom, 2.5-bath home in a fantastic Oregon lo...	4 beds \| 3 baths \| 2,728 sq.ft.	$599,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 2.73% Airbnb Rental Income: $4275 Traditional Rental Income: $3006 Airbnb ROI: 3.39% Traditional ROI: 2.73%
135 Johnson Street Oregon, WI Affordable homes w/ this much character, space, & outdoor potential don't come along often...	3 beds \| 2 baths \| 1,514 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $1992 Airbnb ROI: N/A Traditional ROI: 3.13%
1206 Tivoli Cir Oregon, WI Thoughtfully updated condo in a welcoming Oregon community! Vaulted ceilings and abundant ...	2 beds \| 2 baths \| 1,292 sq.ft.	$445,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 2.47% Airbnb Rental Income: $1802 Traditional Rental Income: $2252 Airbnb ROI: 0.21% Traditional ROI: 2.47%
5431 Lincoln Rd Oregon, WI Rare 20 acre development opportunity on the edge of Oregon WI. Land has access from Lincol...	N/A beds \| N/A baths \| 1,800 sq.ft.	$3,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.37% Airbnb Rental Income: $null Traditional Rental Income: $2381 Airbnb ROI: N/A Traditional ROI: -0.37%
1087 Tundra Ave Oregon, WI This Davis home features a thoughtfully designed, open-concept layout ideal for modern liv...	3 beds \| 2 baths \| 1,523 sq.ft.	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $2381 Airbnb ROI: N/A Traditional ROI: 4.77%
1257 Tivoli Cir Oregon, WI The Villas are the ultimate in peace of mind living. Located within the Highlands of Nethe...	2 beds \| 2 baths \| 1,292 sq.ft.	$441,444	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.04% Airbnb Rental Income: $1802 Traditional Rental Income: $2082 Airbnb ROI: 1.18% Traditional ROI: 3.04%
507 Janesville St Oregon, WI This beautifully updated home offers a fully remodeled main level with a modern kitchen fe...	3 beds \| 2 baths \| 1,728 sq.ft.	$377,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.8% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 4.8%
1232 Tivoli Cir Oregon, WI The Villas are the ultimate in peace of mind living. Located within the Highlands of Nethe...	2 beds \| 2 baths \| 1,292 sq.ft.	$434,900	Airbnb cash on cash: 1.23% Traditional cash on cash: 2.91% Airbnb Rental Income: $1802 Traditional Rental Income: $2000 Airbnb ROI: 1.23% Traditional ROI: 2.91%
2001 Timber Lake Rd Oregon, WI Tucked among the trees on over an acre, this private ranch-style retreat offers comfort an...	4 beds \| 3 baths \| 2,846 sq.ft.	$650,000	Airbnb cash on cash: 2.7% Traditional cash on cash: 2.17% Airbnb Rental Income: $4275 Traditional Rental Income: $3051 Airbnb ROI: 2.7% Traditional ROI: 2.17%
495 Foxfield Ct Oregon, WI This new construction ranch-style home is in its final stages and ready to welcome you hom...	4 beds \| 3 baths \| 2,764 sq.ft.	$695,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 3.02% Airbnb Rental Income: $4275 Traditional Rental Income: $2852 Airbnb ROI: 3.83% Traditional ROI: 3.02%
The Margot Plan Oregon, WI The Margot Plan, Oregon, WI 53575 \| Single Family Residential	4 beds \| 2 baths \| 2,404 sq.ft.	$569,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 0.78% Airbnb Rental Income: $4275 Traditional Rental Income: $2014 Airbnb ROI: 3.34% Traditional ROI: 0.78%
The Emerson Twin Home Plan Oregon, WI The Emerson Twin Home Plan, Oregon, WI 53575 \| Multi Family	3 beds \| 2 baths \| 1,486 sq.ft.	$388,400	Airbnb cash on cash: 6.17% Traditional cash on cash: 1.39% Airbnb Rental Income: $4275 Traditional Rental Income: $1631 Airbnb ROI: 6.17% Traditional ROI: 1.39%
The Conrad Plan Oregon, WI The Conrad Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,974 sq.ft.	$551,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.74% Airbnb Rental Income: $null Traditional Rental Income: $1939 Airbnb ROI: N/A Traditional ROI: 0.74%
The Hendrix Plan Oregon, WI The Hendrix Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,841 sq.ft.	$523,100	Airbnb cash on cash: N/A Traditional cash on cash: 0.76% Airbnb Rental Income: $null Traditional Rental Income: $1848 Airbnb ROI: N/A Traditional ROI: 0.76%
The Cooper Plan Oregon, WI The Cooper Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,764 sq.ft.	$521,500	Airbnb cash on cash: N/A Traditional cash on cash: 0.66% Airbnb Rental Income: $null Traditional Rental Income: $1797 Airbnb ROI: N/A Traditional ROI: 0.66%
The Bryant I Plan Oregon, WI The Bryant I Plan, Oregon, WI 53575 \| Single Family Residential	4 beds \| 2 baths \| 2,406 sq.ft.	$572,500	Airbnb cash on cash: 3.3% Traditional cash on cash: 0.97% Airbnb Rental Income: $4275 Traditional Rental Income: $2130 Airbnb ROI: 3.3% Traditional ROI: 0.97%
The Collette Plan Oregon, WI	2 beds \| 2 baths \| 1,206 sq.ft.	$410,200	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.09% Airbnb Rental Income: $1802 Traditional Rental Income: $1216 Airbnb ROI: 0.34% Traditional ROI: 0.09%
The Carmichael Plan Oregon, WI The Carmichael Plan, Oregon, WI 53575 \| Single Family Residential	4 beds \| 2 baths \| 2,616 sq.ft.	$594,900	Airbnb cash on cash: 3.07% Traditional cash on cash: 0.69% Airbnb Rental Income: $4275 Traditional Rental Income: $2053 Airbnb ROI: 3.07% Traditional ROI: 0.69%
The Davis Twin Home Plan Oregon, WI The Davis Twin Home Plan, Oregon, WI 53575 \| Multi Family	3 beds \| 2 baths \| 1,523 sq.ft.	$398,800	Airbnb cash on cash: 5.94% Traditional cash on cash: 1.5% Airbnb Rental Income: $4275 Traditional Rental Income: $1712 Airbnb ROI: 5.94% Traditional ROI: 1.5%
The Tribeca Plan Oregon, WI	3 beds \| 2 baths \| 1,525 sq.ft.	$415,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.5% Airbnb Rental Income: $null Traditional Rental Income: $1781 Airbnb ROI: N/A Traditional ROI: 1.5%
The Gramercy Plan Oregon, WI	3 beds \| 2 baths \| 1,615 sq.ft.	$427,500	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 1.25%
The Elaine Plan Oregon, WI The Elaine Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,482 sq.ft.	$481,100	Airbnb cash on cash: N/A Traditional cash on cash: 0.56% Airbnb Rental Income: $null Traditional Rental Income: $1621 Airbnb ROI: N/A Traditional ROI: 0.56%
The Astoria Plan Oregon, WI The Astoria Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,616 sq.ft.	$479,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.81% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 0.81%
The Harlow Plan Oregon, WI The Harlow Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,572 sq.ft.	$493,600	Airbnb cash on cash: N/A Traditional cash on cash: 0.67% Airbnb Rental Income: $null Traditional Rental Income: $1710 Airbnb ROI: N/A Traditional ROI: 0.67%
The Atwood Plan Oregon, WI	4 beds \| 2 baths \| 2,446 sq.ft.	$586,100	Airbnb cash on cash: 3.16% Traditional cash on cash: 0.72% Airbnb Rental Income: $4275 Traditional Rental Income: $2040 Airbnb ROI: 3.16% Traditional ROI: 0.72%
The Morris Plan Oregon, WI	3 beds \| 2 baths \| 1,638 sq.ft.	$439,100	Airbnb cash on cash: N/A Traditional cash on cash: 1.24% Airbnb Rental Income: $null Traditional Rental Income: $1766 Airbnb ROI: N/A Traditional ROI: 1.24%
1085 Autumn Blaze Ct Oregon, WI 1085 Autumn Blaze Ct, Oregon, WI 53575 \| Other	N/A beds \| N/A baths \| N/A	$135,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.3% Airbnb Rental Income: $null Traditional Rental Income: $496 Airbnb ROI: N/A Traditional ROI: 0.3%
The Hudson Plan Oregon, WI The Hudson Plan, Oregon, WI 53575 \| Single Family Residential	4 beds \| 2 baths \| 2,172 sq.ft.	$541,300	Airbnb cash on cash: 3.65% Traditional cash on cash: 0.93% Airbnb Rental Income: $4275 Traditional Rental Income: $1997 Airbnb ROI: 3.65% Traditional ROI: 0.93%
457 Savannah Dr Oregon, WI This Chelsea home features a thoughtfully designed, open-concept layout ideal for modern l...	3 beds \| 2 baths \| 1,528 sq.ft.	$439,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.51% Airbnb Rental Income: $null Traditional Rental Income: $2429 Airbnb ROI: N/A Traditional ROI: 4.51%
270 Brook St Oregon, WI Exceptional owner-occupy opportunity with serious income potential!! This well maintained ...	7 beds \| 4 baths \| N/A	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.03% Airbnb Rental Income: $null Traditional Rental Income: $2524 Airbnb ROI: N/A Traditional ROI: 1.03%
500 Bergamont Blvd Oregon, WI 500 Bergamont Blvd, Oregon, WI 53575 \| Other	N/A beds \| N/A baths \| N/A	$795,000	Airbnb cash on cash: N/A Traditional cash on cash: -2.17% Airbnb Rental Income: $null Traditional Rental Income: $592 Airbnb ROI: N/A Traditional ROI: -2.17%
137 Lynne Trl Oregon, WI Tucked into a quiet suburban neighborhood, 137 Lynne Trail offers green space views and th...	3 beds \| 2 baths \| 1,718 sq.ft.	$474,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $2460 Airbnb ROI: N/A Traditional ROI: 2.98%
475 Savannah Dr Oregon, WI This Morris home features a thoughtfully designed, open-concept layout ideal for modern li...	3 beds \| 2 baths \| 1,670 sq.ft.	$469,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.34% Airbnb Rental Income: $null Traditional Rental Income: $2514 Airbnb ROI: N/A Traditional ROI: 4.34%
488 New Hampton Dr Oregon, WI This Collette home features a thoughtfully designed, open-concept layout ideal for modern ...	2 beds \| 2 baths \| 1,206 sq.ft.	$434,900	Airbnb cash on cash: 1.82% Traditional cash on cash: 3.35% Airbnb Rental Income: $1802 Traditional Rental Income: $1937 Airbnb ROI: 1.82% Traditional ROI: 3.35%
1044 Autumn Blaze Ct Oregon, WI 1044 Autumn Blaze Ct, Oregon, WI 53575 \| Single Family Residential	4 beds \| 3 baths \| 2,875 sq.ft.	$749,900	Airbnb cash on cash: 1.86% Traditional cash on cash: 1.04% Airbnb Rental Income: $4275 Traditional Rental Income: $2804 Airbnb ROI: 1.86% Traditional ROI: 1.04%
456 New Hampton Dr Oregon, WI This Gramercy home features a thoughtfully designed, open-concept layout ideal for modern ...	3 beds \| 2 baths \| 1,615 sq.ft.	$464,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.2% Airbnb Rental Income: $null Traditional Rental Income: $2427 Airbnb ROI: N/A Traditional ROI: 4.2%
1035 Merri-Hill Dr Oregon, WI The Pilot Home (504 Greenview Preserve) features a thoughtfully designed, open-concept lay...	3 beds \| 2 baths \| 1,511 sq.ft.	$424,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.61% Airbnb Rental Income: $null Traditional Rental Income: $2300 Airbnb ROI: N/A Traditional ROI: 2.61%
810 Sumac St Oregon, WI Stunning Oregon home offering 4 bd, 5 baths and over 4,150 sq. ft. of beautifully finished...	4 beds \| 3 baths \| 4,150 sq.ft.	$749,900	Airbnb cash on cash: 2.14% Traditional cash on cash: 3.93% Airbnb Rental Income: $4275 Traditional Rental Income: $4619 Airbnb ROI: 2.14% Traditional ROI: 3.93%
361 Concord Dr #6 Oregon, WI 361 Concord Dr #6, Oregon, WI 53575 \| Condo/Coop	2 beds \| 3 baths \| 2,109 sq.ft.	$375,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 2.72% Airbnb Rental Income: $1802 Traditional Rental Income: $2323 Airbnb ROI: -0.15% Traditional ROI: 2.72%

Real Estate investment in Oregon, WI

There are 86 properties for sale in the city of Oregon . The median list price in Oregon is $514,692 and the average price per square foot is $244. In July 2026, the average monthly cash on cash return in Oregon is 2.00%. The average monthly rental income in Oregon is $2,323.

Oregon, WI Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 86 investment properties available for sale in Oregon.

In 2026, the best neighborhood to buy investment property is Oregon.

The ROI for Short-Term is higher than the Long-Term in Oregon with average rental income of $4,275.

Your search for investment property begins and ends here

Investment Property for Sale in Oregon, WI

829 Foxfield Rd

Oregon, WI

4 beds | 3 baths | 3,000 sq.ft.

$615,000

Airbnb cash on cash: 3.37%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $4275

Traditional Rental Income: $3165

Airbnb ROI: 3.37%

Traditional ROI: 3.01%

195 Prairie Mound Dr

Oregon, WI

4 beds | 3 baths | 2,728 sq.ft.

$599,900

Airbnb cash on cash: 3.39%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $4275

Traditional Rental Income: $3006

Airbnb ROI: 3.39%

Traditional ROI: 2.73%

135 Johnson Street

Oregon, WI

3 beds | 2 baths | 1,514 sq.ft.

$375,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.13%

Airbnb Rental Income: $null

Traditional Rental Income: $1992

Airbnb ROI: N/A

Traditional ROI: 3.13%

1206 Tivoli Cir

Oregon, WI

2 beds | 2 baths | 1,292 sq.ft.

$445,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 2.47%

Airbnb Rental Income: $1802

Traditional Rental Income: $2252

Airbnb ROI: 0.21%

Traditional ROI: 2.47%

5431 Lincoln Rd

Oregon, WI

N/A beds | N/A baths | 1,800 sq.ft.

$3,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.37%

Airbnb Rental Income: $null

Traditional Rental Income: $2381

Airbnb ROI: N/A

Traditional ROI: -0.37%

1087 Tundra Ave

Oregon, WI

3 beds | 2 baths | 1,523 sq.ft.

$409,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.77%

Airbnb Rental Income: $null

Traditional Rental Income: $2381

Airbnb ROI: N/A

Traditional ROI: 4.77%

1257 Tivoli Cir

Oregon, WI

2 beds | 2 baths | 1,292 sq.ft.

$441,444

Airbnb cash on cash: 1.18%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $1802

Traditional Rental Income: $2082

Airbnb ROI: 1.18%

Traditional ROI: 3.04%

507 Janesville St

Oregon, WI

3 beds | 2 baths | 1,728 sq.ft.

$377,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.8%

Airbnb Rental Income: $null

Traditional Rental Income: $2385

Airbnb ROI: N/A