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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$1,250,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.36% Airbnb Rental Income: $2249 Traditional Rental Income: $4331 Airbnb ROI: -0.92% 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.	$875,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 2.36% Airbnb Rental Income: $3583 Traditional Rental Income: $3579 Airbnb ROI: 1.4% Traditional ROI: 2.36%
2277 Siskiyou Boulevard Ashland, OR Welcome to this charming cottage in the peaceful Creekside Cottages of Ashland, where matu...	1 beds \| 1 baths \| 861 sq.ft.	$405,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.8% Airbnb Rental Income: $1319 Traditional Rental Income: $2122 Airbnb ROI: -0.39% Traditional ROI: 2.8%
150 Crocker Street Ashland, OR If you've dreamed of calling Ashland home this may be the opportunity you've been waiting ...	3 beds \| 3 baths \| 1,361 sq.ft.	$360,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 5.68% Airbnb Rental Income: $2249 Traditional Rental Income: $2920 Airbnb ROI: 2.03% Traditional ROI: 5.68%
167 Tessa Lane Ashland, OR Modern Mediterranean style custom-built home on nearly 1 acre, just minutes from downtown ...	4 beds \| 5 baths \| 4,039 sq.ft.	$1,600,000	Airbnb cash on cash: -0.02% Traditional cash on cash: -0.02% Airbnb Rental Income: $3583 Traditional Rental Income: $2798 Airbnb ROI: -0.02% Traditional ROI: -0.02%
7130 Highway 66 Ashland, OR Set privately back on 5+ acres in the Sunny Oaks community, this custom 3 bed + office, 2....	3 beds \| 3 baths \| 2,644 sq.ft.	$1,140,000	Airbnb cash on cash: -0.25% Traditional cash on cash: 2.17% Airbnb Rental Income: $2249 Traditional Rental Income: $4254 Airbnb ROI: -0.25% Traditional ROI: 2.17%
694 Timberlake Drive Ashland, OR Back on market no fault of property! Peaceful, private rural retreat in excellent conditio...	3 beds \| 3 baths \| 2,184 sq.ft.	$599,000	Airbnb cash on cash: 0.83% Traditional cash on cash: 4.64% Airbnb Rental Income: $2249 Traditional Rental Income: $3811 Airbnb ROI: 0.83% Traditional ROI: 4.64%
329 N Main Street #8 Ashland, OR Sought after home close to DOWNTOWN Ashland! This charming 2 bed, 1.5 bath townhome is an ...	2 beds \| 2 baths \| 952 sq.ft.	$289,000	Airbnb cash on cash: 1.5% Traditional cash on cash: 5.13% Airbnb Rental Income: $1671 Traditional Rental Income: $2192 Airbnb ROI: 1.5% Traditional ROI: 5.13%
1423 E Main Street Ashland, OR Charming Ashland home tucked behind a solar-powered privacy gate + fully fenced front & ba...	3 beds \| 2 baths \| 1,576 sq.ft.	$548,000	Airbnb cash on cash: 1.48% Traditional cash on cash: 3.97% Airbnb Rental Income: $2249 Traditional Rental Income: $2961 Airbnb ROI: 1.48% Traditional ROI: 3.97%
62 N Mountain Avenue Ashland, OR Stylish turn-key condominium with an excellent central location in beautiful Ashland, OR. ...	3 beds \| 3 baths \| 1,528 sq.ft.	$395,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 5.57% Airbnb Rental Income: $2249 Traditional Rental Income: $3184 Airbnb ROI: 1.52% Traditional ROI: 5.57%
255 Scenic Drive Ashland, OR This beautifully designed and built custom Victorian by Carlos Reichenshammer sits just bl...	4 beds \| 3 baths \| 4,141 sq.ft.	$1,300,000	Airbnb cash on cash: 0.21% Traditional cash on cash: 1.3% Airbnb Rental Income: $3583 Traditional Rental Income: $4109 Airbnb ROI: 0.21% Traditional ROI: 1.3%
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: 0.68% Traditional cash on cash: 3.56% Airbnb Rental Income: $2249 Traditional Rental Income: $3654 Airbnb ROI: 0.68% 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: 1.07% Traditional cash on cash: 5.76% Airbnb Rental Income: $1671 Traditional Rental Income: $2614 Airbnb ROI: 1.07% Traditional ROI: 5.76%
215 PIEDMONT Dr Ashland, OR Perched above the boulevard in an upscale neighborhood of high-end homes, this picturesque...	3 beds \| 3 baths \| 2,120 sq.ft.	$775,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 1.43% Airbnb Rental Income: $2249 Traditional Rental Income: $2520 Airbnb ROI: 0.27% Traditional ROI: 1.43%
854 Twin Pines Circle #7 Ashland, OR BEAUTIFUL LIGHT AND BRIGHT END UNIT with views of the golf course. Don't miss this opportu...	2 beds \| 1 baths \| 896 sq.ft.	$239,900	Airbnb cash on cash: 1.5% Traditional cash on cash: 2.27% Airbnb Rental Income: $1671 Traditional Rental Income: $1377 Airbnb ROI: 1.5% Traditional ROI: 2.27%
138 Clear Creek Drive Ashland, OR You'll be in a prime spot right in Ashland's Railroad District/Spur Rail Subdivision, a su...	2 beds \| 4 baths \| 3,070 sq.ft.	$1,466,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 0.52% Airbnb Rental Income: $1671 Traditional Rental Income: $2565 Airbnb ROI: -0.48% Traditional ROI: 0.52%
492 Herbert Street Ashland, OR Charming and tastefully updated 1965 Ashland bungalow with exceptional curb appeal. Though...	3 beds \| 2 baths \| 1,418 sq.ft.	$568,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 3.45% Airbnb Rental Income: $2249 Traditional Rental Income: $2897 Airbnb ROI: 1.17% Traditional ROI: 3.45%
290 Skycrest Drive Ashland, OR This view property will not disappoint. Perfect wood window placement throughout takes in ...	3 beds \| 3 baths \| 2,943 sq.ft.	$950,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.15% Airbnb Rental Income: $2249 Traditional Rental Income: $2905 Airbnb ROI: -0.23% Traditional ROI: 1.15%
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: -0.28% Traditional cash on cash: 0.38% Airbnb Rental Income: $1416 Traditional Rental Income: $1518 Airbnb ROI: -0.28% Traditional ROI: 0.38%
2140 N Valley View Road Ashland, OR Idyllic Ashland rural sanctuary with stunning valley views and easy access to downtown. En...	4 beds \| 3 baths \| 2,189 sq.ft.	$875,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 1.93% Airbnb Rental Income: $3583 Traditional Rental Income: $2803 Airbnb ROI: 1.92% Traditional ROI: 1.93%
786 Pompadour Drive Ashland, OR Paradox Vineyard Estate is uniquely defined by elements of water, air, the natural light a...	4 beds \| 5 baths \| 5,233 sq.ft.	$3,250,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.53% Airbnb Rental Income: $3583 Traditional Rental Income: $6711 Airbnb ROI: -0.77% Traditional ROI: 0.53%
500 Mt Ashland Ski Road Ashland, OR Tranquil & pristine Mountain oasis on over 121 acres with a campground, marketable timber,...	3 beds \| 3 baths \| 2,145 sq.ft.	$1,049,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 2.29% Airbnb Rental Income: $2249 Traditional Rental Income: $3671 Airbnb ROI: 0.26% Traditional ROI: 2.29%
495 Chestnut Street #19 Ashland, OR Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping...	2 beds \| 2 baths \| 832 sq.ft.	$215,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 6.27% Airbnb Rental Income: $1671 Traditional Rental Income: $2196 Airbnb ROI: 1.4% Traditional ROI: 6.27%
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: -0.08% Traditional cash on cash: 1.11% Airbnb Rental Income: $1319 Traditional Rental Income: $1668 Airbnb ROI: -0.08% 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.	$800,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 3.33% Airbnb Rental Income: $3583 Traditional Rental Income: $4149 Airbnb ROI: 1.52% Traditional ROI: 3.33%
3060 Ashland Mine Road Ashland, OR GREAT OPPORTUNITY! Amazing Price. Earth Advantage certified, 2025 custom home by well-resp...	3 beds \| 2 baths \| 1,996 sq.ft.	$850,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.22% Airbnb Rental Income: $2249 Traditional Rental Income: $3687 Airbnb ROI: 0.69% Traditional ROI: 3.22%
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.	$515,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 2.83% Airbnb Rental Income: $1671 Traditional Rental Income: $2321 Airbnb ROI: 0.51% Traditional ROI: 2.83%
309 GRANITE St Ashland, OR Addressed as 309 and 311 Granite Street, this exceptional estate is tucked above Lithia Pa...	5 beds \| 4 baths \| 5,488 sq.ft.	$1,650,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 2.71% Airbnb Rental Income: $2727 Traditional Rental Income: $8347 Airbnb ROI: -1.37% Traditional ROI: 2.71%
1059 Terra Avenue Ashland, OR Set on a private corner lot above the boulevard, this 4-bedroom, 2.5-bath home offers a ve...	4 beds \| 3 baths \| 1,794 sq.ft.	$539,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 5.43% Airbnb Rental Income: $3583 Traditional Rental Income: $3827 Airbnb ROI: 3.38% Traditional ROI: 5.43%
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: -1.23% Traditional cash on cash: 1.49% Airbnb Rental Income: $2727 Traditional Rental Income: $8403 Airbnb ROI: -1.23% Traditional ROI: 1.49%
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.	$4,100,000	Airbnb cash on cash: -0.99% Traditional cash on cash: 0.44% Airbnb Rental Income: $2727 Traditional Rental Income: $7515 Airbnb ROI: -0.99% Traditional ROI: 0.44%
230 Grant Street Ashland, OR Rare 10-unit investment opportunity in Ashland's Hillview Condominiums -- close to Scenic ...	N/A beds \| N/A baths \| 11,208 sq.ft.	$2,250,000	Airbnb cash on cash: -2.13% Traditional cash on cash: -1.54% Airbnb Rental Income: $1416 Traditional Rental Income: $2223 Airbnb ROI: -2.13% Traditional ROI: -1.54%
345 Fair Oaks Ave Ashland, OR Built in 2007, this inviting 4 bedroom, 2.5 bath home offers 2,170 SF of thoughtfully desi...	4 beds \| 3 baths \| 2,170 sq.ft.	$699,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 3.54% Airbnb Rental Income: $3583 Traditional Rental Income: $3629 Airbnb ROI: 2.26% Traditional ROI: 3.54%
5010 Old Hwy 99 S Ashland, OR A perfect blend of rural serenity & functional living awaits on this 6.65-acre property ju...	2 beds \| 2 baths \| 1,650 sq.ft.	$525,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 3.38% Airbnb Rental Income: $1671 Traditional Rental Income: $2685 Airbnb ROI: 0.36% Traditional ROI: 3.38%
738 Fairway Court Ashland, OR Enjoy expansive views of the 9th fairway at Oak Knoll Golf Course, Grizzly Peak, and surro...	3 beds \| 3 baths \| 1,995 sq.ft.	$795,000	Airbnb cash on cash: 0.2% Traditional cash on cash: 2.86% Airbnb Rental Income: $2249 Traditional Rental Income: $3659 Airbnb ROI: 0.2% Traditional ROI: 2.86%
500 Pompadour Drive Ashland, OR Incredibly desirable Ashland setting--private, quiet & close to town yet distinctly rural....	5 beds \| 5 baths \| 3,566 sq.ft.	$1,250,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.98% Airbnb Rental Income: $2727 Traditional Rental Income: $6917 Airbnb ROI: -0.18% Traditional ROI: 3.98%
391 Clinton Street Ashland, OR Stunning new construction in Ashland's Magnolia Meadows! This exceptional 3-bedroom home f...	3 beds \| 3 baths \| 2,360 sq.ft.	$1,111,500	Airbnb cash on cash: 0.33% Traditional cash on cash: 2.47% Airbnb Rental Income: $2249 Traditional Rental Income: $3907 Airbnb ROI: 0.33% Traditional ROI: 2.47%
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: 0.49% Traditional cash on cash: 2.9% Airbnb Rental Income: $2249 Traditional Rental Income: $3907 Airbnb ROI: 0.49% 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.	$564,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 3.91% Airbnb Rental Income: $2249 Traditional Rental Income: $3423 Airbnb ROI: 0.61% Traditional ROI: 3.91%
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.	$785,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 6.34% Airbnb Rental Income: $3583 Traditional Rental Income: $6309 Airbnb ROI: 1.54% Traditional ROI: 6.34%

Real Estate investment in Ashland, OR

There are 109 properties for sale in the city of Ashland . The median list price in Ashland is $564,662 and the average price per square foot is $243. In July 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,031.

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

There are 109 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 $3,031.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

545 Ashland Creek Drive

Ashland, OR

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

$1,250,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $2249

Traditional Rental Income: $4331

Airbnb ROI: -0.92%

Traditional ROI: 1.36%

774 Lisa Lane

Ashland, OR

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

$875,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $3583

Traditional Rental Income: $3579

Airbnb ROI: 1.4%

Traditional ROI: 2.36%

2277 Siskiyou Boulevard

Ashland, OR

1 beds | 1 baths | 861 sq.ft.

$405,000

Airbnb cash on cash: -0.39%

Traditional cash on cash: 2.8%

Airbnb Rental Income: $1319

Traditional Rental Income: $2122

Airbnb ROI: -0.39%

Traditional ROI: 2.8%

150 Crocker Street

Ashland, OR

3 beds | 3 baths | 1,361 sq.ft.

$360,000

Airbnb cash on cash: 2.03%

Traditional cash on cash: 5.68%

Airbnb Rental Income: $2249

Traditional Rental Income: $2920

Airbnb ROI: 2.03%

Traditional ROI: 5.68%

167 Tessa Lane

Ashland, OR

4 beds | 5 baths | 4,039 sq.ft.

$1,600,000

Airbnb cash on cash: -0.02%

Traditional cash on cash: -0.02%

Airbnb Rental Income: $3583

Traditional Rental Income: $2798

Airbnb ROI: -0.02%

Traditional ROI: -0.02%

7130 Highway 66

Ashland, OR

3 beds | 3 baths | 2,644 sq.ft.

$1,140,000

Airbnb cash on cash: -0.25%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2249

Traditional Rental Income: $4254

Airbnb ROI: -0.25%

Traditional ROI: 2.17%

694 Timberlake Drive

Ashland, OR

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

$599,000

Airbnb cash on cash: 0.83%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $2249

Traditional Rental Income: $3811

Airbnb ROI: 0.83%

Traditional ROI: 4.64%

329 N Main Street #8

Ashland, OR

2 beds | 2 baths | 952 sq.ft.

$289,000

Airbnb cash on cash: 1.5%

Traditional cash on cash: 5.13%

Airbnb Rental Income: $1671

Traditional Rental Income: $2192

Airbnb ROI: 1.5%