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.

Single Family Homes for Sale in Ashland, OR

Search for Single Family Residential for Sale in Ashland, Oregon. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 89 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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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%
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%
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%
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%
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%
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 Rd 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%
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%
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%
770 Elkader Street Ashland, OR First time on the market in over 50 years! Mid-century cottage overlooking a large .67 of ...	2 beds \| 1 baths \| 1,855 sq.ft.	$690,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.93% Airbnb Rental Income: $1671 Traditional Rental Income: $1984 Airbnb ROI: -0.28% Traditional ROI: 0.93%
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.	$715,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 4.14% Airbnb Rental Income: $3583 Traditional Rental Income: $4082 Airbnb ROI: 2.22% Traditional ROI: 4.14%
827 Tyler Creek Road Ashland, OR Versatile, spacious, and thoroughly updated home on private wooded acreage in the Cascade-...	3 beds \| 3 baths \| 2,833 sq.ft.	$575,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 5.83% Airbnb Rental Income: $2249 Traditional Rental Income: $4187 Airbnb ROI: 1.18% Traditional ROI: 5.83%
1087 Oak Knoll Drive Ashland, OR Light-filled & well-maintained 2-story home in the desirable Oak Knoll Meadows, ideally lo...	3 beds \| 3 baths \| 1,753 sq.ft.	$499,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 4.86% Airbnb Rental Income: $2249 Traditional Rental Income: $3399 Airbnb ROI: 1.19% Traditional ROI: 4.86%
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.	$725,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 4.33% Airbnb Rental Income: $3583 Traditional Rental Income: $4388 Airbnb ROI: 1.98% Traditional ROI: 4.33%
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.	$1,350,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 1.68% Airbnb Rental Income: $2249 Traditional Rental Income: $4209 Airbnb ROI: -0.33% Traditional ROI: 1.68%
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: 0.95% Traditional cash on cash: 2.21% Airbnb Rental Income: $3583 Traditional Rental Income: $4310 Airbnb ROI: 0.95% Traditional ROI: 2.21%
5293 Highway 66 Ashland, OR Located just outside Ashland, this property offers a rare blend of natural beauty, water, ...	4 beds \| 4 baths \| 4,977 sq.ft.	$2,195,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 1.2% Airbnb Rental Income: $3583 Traditional Rental Income: $5427 Airbnb ROI: -0.1% Traditional ROI: 1.2%
480 Harrison Street Ashland, OR Charming single-level cottage in one of Ashland's most desirable locations, with stunning ...	2 beds \| 1 baths \| 886 sq.ft.	$385,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 3.66% Airbnb Rental Income: $1671 Traditional Rental Income: $2146 Airbnb ROI: 1.05% Traditional ROI: 3.66%
7550 Hyatt Prairie Road Ashland, OR Attention investors!! If you're looking for a cozy getaway close to all the recreational a...	2 beds \| 2 baths \| 1,472 sq.ft.	$494,000	Airbnb cash on cash: 0.74% Traditional cash on cash: 3.78% Airbnb Rental Income: $1671 Traditional Rental Income: $2605 Airbnb ROI: 0.74% Traditional ROI: 3.78%
602 Ashland Street Ashland, OR Quality custom view home in a private natural setting above the boulevard, just six minute...	3 beds \| 3 baths \| 3,161 sq.ft.	$1,000,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 2.15% Airbnb Rental Income: $2249 Traditional Rental Income: $4080 Airbnb ROI: -0.43% Traditional ROI: 2.15%

Your search for investment property begins and ends here

Single Family Homes 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%

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%

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%

255 Scenic Drive

Ashland, OR

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

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

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

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%