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
377 Concord Dr Oregon, WI Move in ready! Come and enjoy the ease and convenience of condo living with this private ...	2 beds \| 2 baths \| 1,406 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.55% Airbnb Rental Income: $null Traditional Rental Income: $1866 Airbnb ROI: N/A Traditional ROI: 2.55%
530 Lexington Dr Oregon, WI Gorgeous stand-alone condominium home in Oregonâs desirable Hawthorne Parks neighborhood...	3 beds \| 2 baths \| 1,824 sq.ft.	$379,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $1929 Airbnb ROI: N/A Traditional ROI: 3.22%
145 Dewey St Oregon, WI No showings 'til Open 11/19. This home has endless character! Beautiful hardwood floors, t...	4 beds \| 2 baths \| 2,410 sq.ft.	$425,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 3.38% Airbnb Rental Income: $3023 Traditional Rental Income: $2166 Airbnb ROI: 3.79% Traditional ROI: 3.38%
1370 Connemara Ln Oregon, WI Stunning & impeccably maintained 4 bedroom/3 bath custom ranch home in desirable Hampton H...	4 beds \| 3 baths \| 3,700 sq.ft.	$749,900	Airbnb cash on cash: 1.22% Traditional cash on cash: 1.98% Airbnb Rental Income: $3023 Traditional Rental Income: $2860 Airbnb ROI: 1.22% Traditional ROI: 1.98%
748 Dunn Ave Oregon, WI Check out the virtual tour! Unpack your things and move right in!! This quaint, convenient...	2 beds \| 2 baths \| 1,318 sq.ft.	$269,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.71% Airbnb Rental Income: $null Traditional Rental Income: $1837 Airbnb ROI: N/A Traditional ROI: 3.71%
136 Alpine Meadows Ct Oregon, WI No showings until open house 3/8/20. Don't miss this first floor, barrier free ranch style...	3 beds \| 3 baths \| 2,268 sq.ft.	$372,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $2560 Airbnb ROI: N/A Traditional ROI: 3.96%
118 Elliott Ln Oregon, WI Priced to move. Spacious 3 bedroom, 2.5 bathroom townhouse with room to expand. Brand new ...	3 beds \| 2 baths \| 1,464 sq.ft.	$297,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.42% Airbnb Rental Income: $null Traditional Rental Income: $1968 Airbnb ROI: N/A Traditional ROI: 3.42%
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: 1.55% Traditional cash on cash: 3.01% Airbnb Rental Income: $3023 Traditional Rental Income: $3165 Airbnb ROI: 1.55% Traditional ROI: 3.01%
4805 Schneider Dr Oregon, WI Two homes on 4 private acres just minutes to the Beltline and downtown Madison! Beautiful ...	4 beds \| 3 baths \| 2,288 sq.ft.	$799,900	Airbnb cash on cash: 0.54% Traditional cash on cash: 1.35% Airbnb Rental Income: $3023 Traditional Rental Income: $2937 Airbnb ROI: 0.54% Traditional ROI: 1.35%
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.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $2252 Airbnb ROI: N/A Traditional ROI: 2.67%
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.	$2,999,999	Airbnb cash on cash: N/A Traditional cash on cash: -0.27% Airbnb Rental Income: $null Traditional Rental Income: $2381 Airbnb ROI: N/A Traditional ROI: -0.27%
187 Sterling Dr Oregon, WI This one has all the check boxes. Huge, flat yard. Three car tandem garage, NEWER theatre...	3 beds \| 2 baths \| 1,613 sq.ft.	$414,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.35% Airbnb Rental Income: $null Traditional Rental Income: $2280 Airbnb ROI: N/A Traditional ROI: 3.35%
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.	$399,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $2381 Airbnb ROI: N/A Traditional ROI: 4.91%
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: N/A Traditional cash on cash: 3.04% Airbnb Rental Income: $null Traditional Rental Income: $2082 Airbnb ROI: N/A 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.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.99% Airbnb Rental Income: $null Traditional Rental Income: $2385 Airbnb ROI: N/A Traditional ROI: 4.99%
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: N/A Traditional cash on cash: 2.91% Airbnb Rental Income: $null Traditional Rental Income: $2000 Airbnb ROI: N/A Traditional ROI: 2.91%
255-259 Park St Oregon, WI Calling all investors!! Ranch~style side~by~side duplex in the heart of downtown Oregon. ...	6 beds \| 2 baths \| N/A	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $2587 Airbnb ROI: N/A Traditional ROI: 2.59%
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.	$625,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 2.29% Airbnb Rental Income: $3023 Traditional Rental Income: $3051 Airbnb ROI: 1.06% Traditional ROI: 2.29%
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: 2.22% Traditional cash on cash: 3.02% Airbnb Rental Income: $3023 Traditional Rental Income: $2852 Airbnb ROI: 2.22% Traditional ROI: 3.02%
2395 White Oak Trl Oregon, WI 2395 White Oak Trl, Oregon, WI 53575 \| Single Family Residential	4 beds \| 4 baths \| 5,263 sq.ft.	$1,599,999	Airbnb cash on cash: -1.34% Traditional cash on cash: -0.83% Airbnb Rental Income: $3023 Traditional Rental Income: $3086 Airbnb ROI: -1.34% Traditional ROI: -0.83%
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: 1.37% Traditional cash on cash: 0.78% Airbnb Rental Income: $3023 Traditional Rental Income: $2014 Airbnb ROI: 1.37% 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: 3.31% Traditional cash on cash: 1.39% Airbnb Rental Income: $3023 Traditional Rental Income: $1631 Airbnb ROI: 3.31% 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 Olivia Plan Oregon, WI The Olivia Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,516 sq.ft.	$493,400	Airbnb cash on cash: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $1698 Airbnb ROI: N/A Traditional ROI: 0.64%
The Sawyer Plan Oregon, WI The Sawyer Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,879 sq.ft.	$502,900	Airbnb cash on cash: N/A Traditional cash on cash: 0.96% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 0.96%
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: 1.35% Traditional cash on cash: 0.97% Airbnb Rental Income: $3023 Traditional Rental Income: $2130 Airbnb ROI: 1.35% Traditional ROI: 0.97%
The Collette Plan Oregon, WI	2 beds \| 2 baths \| 1,206 sq.ft.	$410,200	Airbnb cash on cash: N/A Traditional cash on cash: 0.09% Airbnb Rental Income: $null Traditional Rental Income: $1216 Airbnb ROI: N/A Traditional ROI: 0.09%
The Stewart Plan Oregon, WI	4 beds \| 2 baths \| 2,061 sq.ft.	$474,800	Airbnb cash on cash: 2.2% Traditional cash on cash: 1.4% Airbnb Rental Income: $3023 Traditional Rental Income: $1976 Airbnb ROI: 2.2% Traditional ROI: 1.4%
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: 1.19% Traditional cash on cash: 0.69% Airbnb Rental Income: $3023 Traditional Rental Income: $2053 Airbnb ROI: 1.19% 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: 3.15% Traditional cash on cash: 1.5% Airbnb Rental Income: $3023 Traditional Rental Income: $1712 Airbnb ROI: 3.15% Traditional ROI: 1.5%
The Jade Plan Oregon, WI The Jade Plan, Oregon, WI 53575 \| Single Family Residential	3 beds \| 2 baths \| 1,520 sq.ft.	$419,300	Airbnb cash on cash: N/A Traditional cash on cash: 1.25% Airbnb Rental Income: $null Traditional Rental Income: $1698 Airbnb ROI: N/A Traditional ROI: 1.25%
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 Costello Plan Oregon, WI	3 beds \| 2 baths \| 1,860 sq.ft.	$452,600	Airbnb cash on cash: N/A Traditional cash on cash: 1.32% Airbnb Rental Income: $null Traditional Rental Income: $1855 Airbnb ROI: N/A Traditional ROI: 1.32%
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.	$481,600	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 Hoffman Plan Oregon, WI The Hoffman Plan, Oregon, WI 53575 \| Single Family Residential	4 beds \| 2 baths \| 2,045 sq.ft.	$548,400	Airbnb cash on cash: 1.53% Traditional cash on cash: 0.84% Airbnb Rental Income: $3023 Traditional Rental Income: $1976 Airbnb ROI: 1.53% Traditional ROI: 0.84%

Real Estate investment in Oregon, WI

There are 149 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 $237. In October 2026, the average monthly cash on cash return in Oregon is 1.00%. The average monthly rental income in Oregon is $2,164.

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

There are 149 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 $3,023.

Your search for investment property begins and ends here

Investment Property for Sale in Oregon, WI

377 Concord Dr

Oregon, WI

2 beds | 2 baths | 1,406 sq.ft.

$365,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.55%

Airbnb Rental Income: $null

Traditional Rental Income: $1866

Airbnb ROI: N/A

Traditional ROI: 2.55%

530 Lexington Dr

Oregon, WI

3 beds | 2 baths | 1,824 sq.ft.

$379,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.22%

Airbnb Rental Income: $null

Traditional Rental Income: $1929

Airbnb ROI: N/A

Traditional ROI: 3.22%

145 Dewey St

Oregon, WI

4 beds | 2 baths | 2,410 sq.ft.

$425,000

Airbnb cash on cash: 3.79%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $3023

Traditional Rental Income: $2166

Airbnb ROI: 3.79%

Traditional ROI: 3.38%

1370 Connemara Ln

Oregon, WI

4 beds | 3 baths | 3,700 sq.ft.

$749,900

Airbnb cash on cash: 1.22%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $3023

Traditional Rental Income: $2860

Airbnb ROI: 1.22%

Traditional ROI: 1.98%

748 Dunn Ave

Oregon, WI

2 beds | 2 baths | 1,318 sq.ft.

$269,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.71%

Airbnb Rental Income: $null

Traditional Rental Income: $1837

Airbnb ROI: N/A

Traditional ROI: 3.71%

136 Alpine Meadows Ct

Oregon, WI

3 beds | 3 baths | 2,268 sq.ft.

$372,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.96%

Airbnb Rental Income: $null

Traditional Rental Income: $2560

Airbnb ROI: N/A

Traditional ROI: 3.96%

118 Elliott Ln

Oregon, WI

3 beds | 2 baths | 1,464 sq.ft.

$297,500

Airbnb cash on cash: N/A

Traditional cash on cash: 3.42%

Airbnb Rental Income: $null

Traditional Rental Income: $1968

Airbnb ROI: N/A

Traditional ROI: 3.42%

829 Foxfield Rd

Oregon, WI

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

$615,000

Airbnb cash on cash: 1.55%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $3023

Traditional Rental Income: $3165

Airbnb ROI: 1.55%