Real Estate Investment Properties for Sale in Ashland, OR

Looking for investment property in Ashland, OR with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
175 Lithia Way #200 Ashland, OR A second story corner residence in the A LEED-certified Plaza West Building with a flowing...	1 beds \| 2 baths \| 1,448 sq.ft.	$710,000	Airbnb cash on cash: -2.48% Traditional cash on cash: 0.82% Airbnb Rental Income: $1330 Traditional Rental Income: $3103 Airbnb ROI: -2.48% Traditional ROI: 0.82%
545 Ashland Creek Drive Ashland, OR Private tranquility in the treetops 4 min. to downtown Ashland. Views of Lithia Park w/soo...	3 beds \| 3 baths \| 3,108 sq.ft.	$1,195,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.36% Airbnb Rental Income: $2615 Traditional Rental Income: $4331 Airbnb ROI: -0.75% Traditional ROI: 1.36%
774 Lisa Lane Ashland, OR Quality built contemporary home placed among the madrone and pine trees in the hills of be...	4 beds \| 4 baths \| 2,981 sq.ft.	$850,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 2.43% Airbnb Rental Income: $3174 Traditional Rental Income: $3579 Airbnb ROI: 1.01% Traditional ROI: 2.43%
1750 Crestview Drive Ashland, OR Impeccable views and quality updated home is ready to go! Step outside directly onto hikin...	3 beds \| 3 baths \| 2,103 sq.ft.	$735,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.23% Airbnb Rental Income: $2615 Traditional Rental Income: $2372 Airbnb ROI: 0.68% Traditional ROI: 1.23%
3729 Old Highway 99 S Ashland, OR Enjoy spectacular views of Emigrant Lake & the surrounding mountains from this exceptional...	3 beds \| 4 baths \| 3,713 sq.ft.	$889,000	Airbnb cash on cash: -0.04% Traditional cash on cash: 3.74% Airbnb Rental Income: $2615 Traditional Rental Income: $5122 Airbnb ROI: -0.04% Traditional ROI: 3.74%
853 Pavilion Place Ashland, OR Location, location, location! Located in the fabulous 55+ Mountain Meadows Community, this...	1 beds \| 1 baths \| 872 sq.ft.	$190,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 6.76% Airbnb Rental Income: $1330 Traditional Rental Income: $1739 Airbnb ROI: 2.22% Traditional ROI: 6.76%
524 W Nevada Street Ashland, OR Desirable end-unit townhome with quality finishes and abundant natural light, directly adj...	3 beds \| 3 baths \| 2,106 sq.ft.	$475,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 5.77% Airbnb Rental Income: $2615 Traditional Rental Income: $3663 Airbnb ROI: 2.01% Traditional ROI: 5.77%
2140 Birchwood Lane Ashland, OR This inviting, move-in-ready home is filled with natural light and offers a functional, co...	2 beds \| 2 baths \| 1,359 sq.ft.	$410,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 2% Airbnb Rental Income: $1891 Traditional Rental Income: $1702 Airbnb ROI: 1.18% Traditional ROI: 2%
496 Beach Street Ashland, OR Gorgeously renovated Victorian blends historic charm with modern luxury in the heart of As...	5 beds \| 6 baths \| 3,647 sq.ft.	$845,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 8.29% Airbnb Rental Income: $3704 Traditional Rental Income: $8631 Airbnb ROI: 1.01% Traditional ROI: 8.29%
197 Timberlake Drive Ashland, OR Private 5.5-acre mountain retreat with stunning views, gated entry, asphalt drive, and exp...	4 beds \| 4 baths \| 2,700 sq.ft.	$725,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 1.86% Airbnb Rental Income: $3174 Traditional Rental Income: $2798 Airbnb ROI: 1.35% Traditional ROI: 1.86%
1650 Neil Creek Road Ashland, OR OWNER CARRY AVAILABLE! GOURMET KITCHEN. EMIGRANT LAKE VIEWS. 22 ACRES OF PRIVACY. This upd...	5 beds \| 4 baths \| 3,270 sq.ft.	$1,175,000	Airbnb cash on cash: 0.94% Traditional cash on cash: N/A Airbnb Rental Income: $3704 Traditional Rental Income: $0 Airbnb ROI: 0.94% Traditional ROI: N/A
2260 Old Highway 99 S Ashland, OR Welcome to PrayerFarm, a unique oasis for multi-generational living, community, homesteadi...	4 beds \| 3 baths \| 2,847 sq.ft.	$900,000	Airbnb cash on cash: 0.99% Traditional cash on cash: 1.28% Airbnb Rental Income: $3174 Traditional Rental Income: $2699 Airbnb ROI: 0.99% Traditional ROI: 1.28%
593 Crowson Road Ashland, OR Fully renovated home by Coleman Creek Construction with detached studio and garage on rare...	3 beds \| 3 baths \| 2,101 sq.ft.	$735,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.56% Airbnb Rental Income: $2615 Traditional Rental Income: $3654 Airbnb ROI: 1.13% Traditional ROI: 3.56%
2214 McCall Drive Ashland, OR Light and bright upstairs condo in the McCall Drive Condominium subdivision. This well-mai...	2 beds \| 2 baths \| 1,005 sq.ft.	$319,500	Airbnb cash on cash: 1.65% Traditional cash on cash: 5.74% Airbnb Rental Income: $1891 Traditional Rental Income: $2614 Airbnb ROI: 1.65% Traditional ROI: 5.74%
965 Golden Aspen Place Ashland, OR Enter this freshly painted 2-bedroom, 1.5-bath condo with patio access to the beautiful co...	2 beds \| 2 baths \| 1,078 sq.ft.	$323,000	Airbnb cash on cash: -2.08% Traditional cash on cash: 1.63% Airbnb Rental Income: $1891 Traditional Rental Income: $2514 Airbnb ROI: -2.08% Traditional ROI: 1.63%
5831 OLD HIGHWAY 99 Ashland, OR Set among more than 37 private acres in the beautiful Siskiyou Mountains, this remarkable ...	3 beds \| 5 baths \| 3,572 sq.ft.	$950,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 2.55% Airbnb Rental Income: $2615 Traditional Rental Income: $3816 Airbnb ROI: 0.49% Traditional ROI: 2.55%
738 Normal Avenue Ashland, OR Tucked away from the main road yet just a short distance to Southern Oregon University, th...	2 beds \| 3 baths \| 1,128 sq.ft.	$322,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.72% Airbnb Rental Income: $1891 Traditional Rental Income: $2393 Airbnb ROI: 1.4% Traditional ROI: 4.72%
128 S Mountain Avenue Ashland, OR Prime Investment & Development Opportunity in Ashland. Well-maintained duplex located clos...	N/A beds \| N/A baths \| 1,440 sq.ft.	$855,000	Airbnb cash on cash: 0.22% Traditional cash on cash: 0.38% Airbnb Rental Income: $1891 Traditional Rental Income: $1518 Airbnb ROI: 0.22% Traditional ROI: 0.38%
800 Park Street Ashland, OR Light-filled and thoughtfully updated, this home offers comfortable living in a quiet neig...	2 beds \| 2 baths \| 960 sq.ft.	$315,000	Airbnb cash on cash: 1.43% Traditional cash on cash: 2.62% Airbnb Rental Income: $1891 Traditional Rental Income: $1739 Airbnb ROI: 1.43% Traditional ROI: 2.62%
786 Pompadour Drive Ashland, OR Seller financing now available! Paradox Vineyard Estate is uniquely defined by elements of...	4 beds \| 5 baths \| 5,233 sq.ft.	$3,250,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.53% Airbnb Rental Income: $3174 Traditional Rental Income: $6711 Airbnb ROI: -0.88% Traditional ROI: 0.53%
500 Mt Ashland Ski Road Ashland, OR Priced to sell & Owner will carry! Tranquil mountain oasis on 121+ acres featuring a campg...	3 beds \| 3 baths \| 2,145 sq.ft.	$825,000	Airbnb cash on cash: 1.03% Traditional cash on cash: 3.21% Airbnb Rental Income: $2615 Traditional Rental Income: $3671 Airbnb ROI: 1.03% Traditional ROI: 3.21%
1320 N Mountain Avenue Ashland, OR Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth wit...	3 beds \| 5 baths \| 2,892 sq.ft.	$2,800,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.39% Airbnb Rental Income: $2615 Traditional Rental Income: $7439 Airbnb ROI: -0.71% Traditional ROI: 1.39%
2000 Colestin Road Ashland, OR Beautiful Colestin property on 159 acres with 5 separate lots combined, seasonal creek run...	1 beds \| 1 baths \| 460 sq.ft.	$680,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.11% Airbnb Rental Income: $1330 Traditional Rental Income: $1668 Airbnb ROI: -0.07% Traditional ROI: 1.11%
307 Hillcrest Street Ashland, OR Custom view home with charming detached guest cottage located just above downtown between ...	4 beds \| 4 baths \| 3,159 sq.ft.	$750,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.62% Airbnb Rental Income: $3174 Traditional Rental Income: $4149 Airbnb ROI: 1.2% Traditional ROI: 3.62%
220 Nutley Street Ashland, OR Stunning 2022 transformation of a classic 1920s single-level cottage situated on a spaciou...	2 beds \| 2 baths \| 913 sq.ft.	$500,000	Airbnb cash on cash: 0.95% Traditional cash on cash: 2.94% Airbnb Rental Income: $1891 Traditional Rental Income: $2321 Airbnb ROI: 0.95% Traditional ROI: 2.94%
583 Coffee Lane Ashland, OR Built in 2022 with an emphasis on efficiency, simplicity, and modern design, this Earth Ad...	2 beds \| 1 baths \| 752 sq.ft.	$379,900	Airbnb cash on cash: 1.47% Traditional cash on cash: 3.51% Airbnb Rental Income: $1891 Traditional Rental Income: $2116 Airbnb ROI: 1.47% Traditional ROI: 3.51%
500 Ashland Loop Road Ashland, OR Discover this extraordinary Southern Oregon Luxury 2 acre estate perched above downtown As...	5 beds \| 6 baths \| 6,033 sq.ft.	$2,500,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.46% Airbnb Rental Income: $3704 Traditional Rental Income: $8403 Airbnb ROI: -0.92% Traditional ROI: 1.46%
1440 E Nevada Street Ashland, OR A private retreat setting where nature meets luxurious living. The 5BR/5BA Contemporary ho...	5 beds \| 5 baths \| 5,002 sq.ft.	$3,750,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.56% Airbnb Rental Income: $3704 Traditional Rental Income: $7515 Airbnb ROI: -0.77% Traditional ROI: 0.56%
5010 Old Highway 99 S Ashland, OR Peaceful country living opportunity on 6.65 acres nestled amongst the madrones, not far fr...	2 beds \| 2 baths \| 1,750 sq.ft.	$399,000	Airbnb cash on cash: 1.21% Traditional cash on cash: 4.68% Airbnb Rental Income: $1891 Traditional Rental Income: $2685 Airbnb ROI: 1.21% Traditional ROI: 4.68%
381 Clinton Street Ashland, OR Stunning new construction in Ashland's Magnolia Meadows! This exceptional 3-bedroom home f...	3 beds \| 3 baths \| 2,092 sq.ft.	$991,800	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.9% Airbnb Rental Income: $2615 Traditional Rental Income: $3907 Airbnb ROI: 0.82% Traditional ROI: 2.9%
938 Cypress Point Loop Ashland, OR Gracious, single-level 3 bed, 2 bath home located in the charming and peaceful Oak Knoll S...	3 beds \| 2 baths \| 2,351 sq.ft.	$525,000	Airbnb cash on cash: 1.31% Traditional cash on cash: 4.23% Airbnb Rental Income: $2615 Traditional Rental Income: $3423 Airbnb ROI: 1.31% Traditional ROI: 4.23%
461 Waterline Road Ashland, OR Tucked away on a quiet, tree-lined street, this beautiful home strikes the perfect balance...	4 beds \| 4 baths \| 3,404 sq.ft.	$766,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 6.49% Airbnb Rental Income: $3174 Traditional Rental Income: $6309 Airbnb ROI: 1.09% Traditional ROI: 6.49%
527 Chestnut Street Ashland, OR Freshly renovated turn of the century home set on over a third of an acre lot with views a...	4 beds \| 4 baths \| 2,032 sq.ft.	$699,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.14% Airbnb Rental Income: $3174 Traditional Rental Income: $4082 Airbnb ROI: 1.64% Traditional ROI: 4.14%
369 Alta Avenue Ashland, OR Built in 1996, this Ashland property features a 1,910 square foot main residence and a per...	3 beds \| 4 baths \| 2,854 sq.ft.	$649,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 0.9% Airbnb Rental Income: $2615 Traditional Rental Income: $2131 Airbnb ROI: 0.67% Traditional ROI: 0.9%
4201 Highway 66 Ashland, OR Rare opportunity to own 71.51 acres just right outside city limits of Ashland! LOCATION IS...	1 beds \| 1 baths \| 513 sq.ft.	$595,808	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.89% Airbnb Rental Income: $1330 Traditional Rental Income: $1974 Airbnb ROI: -0.01% Traditional ROI: 1.89%
7979 Hyatt Prairie Road #45 Ashland, OR Own a charming lakeside retreat at Hyatt Lake Resort, where adventure and relaxation await...	1 beds \| 1 baths \| 399 sq.ft.	$250,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 4.78% Airbnb Rental Income: $1330 Traditional Rental Income: $1685 Airbnb ROI: 1.54% Traditional ROI: 4.78%
7979 Hyatt Prairie Road #46 Ashland, OR Escape to nature with this cozy and fully furnished mountain cabin nestled in the Hyatt La...	2 beds \| 1 baths \| 399 sq.ft.	$175,000	Airbnb cash on cash: 5.81% Traditional cash on cash: 7.89% Airbnb Rental Income: $1891 Traditional Rental Income: $1734 Airbnb ROI: 5.81% Traditional ROI: 7.89%
211 Glenview Drive Ashland, OR Panoramic valley views, seconds from Downtown Ashland & Lithia Park - a rare combination o...	4 beds \| 3 baths \| 2,711 sq.ft.	$625,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 5.18% Airbnb Rental Income: $3174 Traditional Rental Income: $4388 Airbnb ROI: 1.87% Traditional ROI: 5.18%
8612 OR-66 Ashland, OR Stunning new contemporary home with mountain views on 20+ private acres! Interior highligh...	3 beds \| 4 baths \| 2,451 sq.ft.	$999,999	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.61% Airbnb Rental Income: $2615 Traditional Rental Income: $4209 Airbnb ROI: 0.23% Traditional ROI: 2.61%
852 Oak Street Ashland, OR Platinum Earth Advantage home just minutes from downtown, offering 2,750 sq ft of thoughtf...	4 beds \| 3 baths \| 2,750 sq.ft.	$1,295,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 2.21% Airbnb Rental Income: $3174 Traditional Rental Income: $4310 Airbnb ROI: 0.67% Traditional ROI: 2.21%

Real Estate investment in Ashland, OR

There are 104 properties for sale in the city of Ashland . The median list price in Ashland is $551,737 and the average price per square foot is $250. In November 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $2,699.

Ashland, OR Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 104 investment properties available for sale in Ashland.

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

The ROI for Long-Term is higher than the Short-Term in Ashland with average rental income of $2,699.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

175 Lithia Way #200

Ashland, OR

1 beds | 2 baths | 1,448 sq.ft.

$710,000

Airbnb cash on cash: -2.48%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $1330

Traditional Rental Income: $3103

Airbnb ROI: -2.48%

Traditional ROI: 0.82%

545 Ashland Creek Drive

Ashland, OR

3 beds | 3 baths | 3,108 sq.ft.

$1,195,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $2615

Traditional Rental Income: $4331

Airbnb ROI: -0.75%

Traditional ROI: 1.36%

774 Lisa Lane

Ashland, OR

4 beds | 4 baths | 2,981 sq.ft.

$850,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 2.43%

Airbnb Rental Income: $3174

Traditional Rental Income: $3579

Airbnb ROI: 1.01%

Traditional ROI: 2.43%

1750 Crestview Drive

Ashland, OR

3 beds | 3 baths | 2,103 sq.ft.

$735,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $2615

Traditional Rental Income: $2372

Airbnb ROI: 0.68%

Traditional ROI: 1.23%

3729 Old Highway 99 S

Ashland, OR

3 beds | 4 baths | 3,713 sq.ft.

$889,000

Airbnb cash on cash: -0.04%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $2615

Traditional Rental Income: $5122

Airbnb ROI: -0.04%

Traditional ROI: 3.74%

853 Pavilion Place

Ashland, OR

1 beds | 1 baths | 872 sq.ft.

$190,000

Airbnb cash on cash: 2.22%

Traditional cash on cash: 6.76%

Airbnb Rental Income: $1330

Traditional Rental Income: $1739

Airbnb ROI: 2.22%

Traditional ROI: 6.76%

524 W Nevada Street

Ashland, OR

3 beds | 3 baths | 2,106 sq.ft.

$475,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 5.77%

Airbnb Rental Income: $2615

Traditional Rental Income: $3663

Airbnb ROI: 2.01%

Traditional ROI: 5.77%

2140 Birchwood Lane

Ashland, OR

2 beds | 2 baths | 1,359 sq.ft.

$410,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 2%

Airbnb Rental Income: $1891

Traditional Rental Income: $1702

Airbnb ROI: 1.18%