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
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: -1.63% Traditional cash on cash: 1.36% Airbnb Rental Income: $1256 Traditional Rental Income: $4331 Airbnb ROI: -1.63% Traditional ROI: 1.36%
610 Orchard Street Ashland, OR Enchanting oasis property, 1/2 acre of lush landscaping, abundant flora waterfalls and swi...	5 beds \| 3 baths \| 3,458 sq.ft.	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.21% Airbnb Rental Income: $null Traditional Rental Income: $4953 Airbnb ROI: N/A Traditional ROI: 3.21%
740 Park Street Ashland, OR Single-level home with a warm and vibrant feel. The open floor plan with vaulted ceilings,...	3 beds \| 2 baths \| 1,406 sq.ft.	$534,000	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.41% Airbnb Rental Income: $1256 Traditional Rental Income: $2751 Airbnb ROI: -0.38% Traditional ROI: 3.41%
271 Cove Road Ashland, OR Stunning brand new custom to-be-built home, by well known builder Lewis Homes LLC. Enjoy 3...	4 beds \| 4 baths \| 3,299 sq.ft.	$1,590,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 2.56% Airbnb Rental Income: $2938 Traditional Rental Income: $5568 Airbnb ROI: 0.32% Traditional ROI: 2.56%
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.	$935,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.45% Airbnb Rental Income: $null Traditional Rental Income: $8631 Airbnb ROI: N/A Traditional ROI: 7.45%
1084 E Main Street Ashland, OR This charming townhome is in Phillip's Corner- an amazing urban center within walking dist...	3 beds \| 2 baths \| 1,286 sq.ft.	$500,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 3.7% Airbnb Rental Income: $1256 Traditional Rental Income: $2793 Airbnb ROI: -0.44% Traditional ROI: 3.7%
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: -1.03% Traditional cash on cash: 2.17% Airbnb Rental Income: $1256 Traditional Rental Income: $4254 Airbnb ROI: -1.03% 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: -0.65% Traditional cash on cash: 4.64% Airbnb Rental Income: $1256 Traditional Rental Income: $3811 Airbnb ROI: -0.65% Traditional ROI: 4.64%
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.	$399,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 5.51% Airbnb Rental Income: $1256 Traditional Rental Income: $3184 Airbnb ROI: -0.71% Traditional ROI: 5.51%
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.	$750,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.47% Airbnb Rental Income: $1256 Traditional Rental Income: $3654 Airbnb ROI: -0.53% Traditional ROI: 3.47%
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.	$322,500	Airbnb cash on cash: -0.24% Traditional cash on cash: 5.7% Airbnb Rental Income: $1200 Traditional Rental Income: $2614 Airbnb ROI: -0.24% Traditional ROI: 5.7%
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.	$249,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.14% Airbnb Rental Income: $1200 Traditional Rental Income: $1377 Airbnb ROI: -0.26% Traditional ROI: 2.14%
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: -0.77% Traditional cash on cash: 0.52% Airbnb Rental Income: $1200 Traditional Rental Income: $2565 Airbnb ROI: -0.77% Traditional ROI: 0.52%
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.	$975,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.09% Airbnb Rental Income: $1256 Traditional Rental Income: $2905 Airbnb ROI: -1.16% Traditional ROI: 1.09%
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: -0.67% Traditional cash on cash: 0.38% Airbnb Rental Income: $1045 Traditional Rental Income: $1518 Airbnb ROI: -0.67% 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.	$889,000	Airbnb cash on cash: 1.23% Traditional cash on cash: 1.88% Airbnb Rental Income: $2938 Traditional Rental Income: $2803 Airbnb ROI: 1.23% Traditional ROI: 1.88%
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: -0.95% Traditional cash on cash: 0.53% Airbnb Rental Income: $2938 Traditional Rental Income: $6711 Airbnb ROI: -0.95% Traditional ROI: 0.53%
495 Chestnut Street #19 Ashland, OR Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping...	2 beds \| 2 baths \| 832 sq.ft.	$229,900	Airbnb cash on cash: -0.55% Traditional cash on cash: 5.81% Airbnb Rental Income: $1200 Traditional Rental Income: $2196 Airbnb ROI: -0.55% Traditional ROI: 5.81%
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: -0.43% Traditional cash on cash: 1.11% Airbnb Rental Income: $1051 Traditional Rental Income: $1668 Airbnb ROI: -0.43% Traditional ROI: 1.11%
3060 Ashland Mine Road Ashland, OR Modern luxury meets privacy in this 2025 custom home by Suncrest Homes, a trusted builder ...	3 beds \| 2 baths \| 1,996 sq.ft.	$889,900	Airbnb cash on cash: -0.38% Traditional cash on cash: 3.03% Airbnb Rental Income: $1256 Traditional Rental Income: $3687 Airbnb ROI: -0.38% Traditional ROI: 3.03%
30 Steinman Drive Ashland, OR $35,000 Price Reduction!!! Peaceful mountain retreat with sweeping views and abundant natu...	3 beds \| 3 baths \| 2,639 sq.ft.	$550,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 5.58% Airbnb Rental Income: $1256 Traditional Rental Income: $4090 Airbnb ROI: -0.7% Traditional ROI: 5.58%
1040 E Main Street Ashland, OR This versatile property offers a range of living options: enjoy it as a single-family home...	3 beds \| 2 baths \| 1,266 sq.ft.	$475,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 3.94% Airbnb Rental Income: $1256 Traditional Rental Income: $2605 Airbnb ROI: 0.01% Traditional ROI: 3.94%
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.	$529,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.73% Airbnb Rental Income: $1200 Traditional Rental Income: $2321 Airbnb ROI: -0.32% Traditional ROI: 2.73%
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: N/A Traditional cash on cash: 2.71% Airbnb Rental Income: $null Traditional Rental Income: $8347 Airbnb ROI: N/A 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: 2.32% Traditional cash on cash: 5.43% Airbnb Rental Income: $2938 Traditional Rental Income: $3827 Airbnb ROI: 2.32% 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: N/A Traditional cash on cash: 1.49% Airbnb Rental Income: $null Traditional Rental Income: $8403 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.44% Airbnb Rental Income: $null Traditional Rental Income: $7515 Airbnb ROI: N/A 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: -2.28% Traditional cash on cash: -1.54% Airbnb Rental Income: $1045 Traditional Rental Income: $2223 Airbnb ROI: -2.28% Traditional ROI: -1.54%
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: -0.44% Traditional cash on cash: 3.38% Airbnb Rental Income: $1200 Traditional Rental Income: $2685 Airbnb ROI: -0.44% Traditional ROI: 3.38%
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.	$1,395,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $6917 Airbnb ROI: N/A Traditional ROI: 3.46%
391 Clinton Street #5200 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: -0.47% Traditional cash on cash: 2.47% Airbnb Rental Income: $1256 Traditional Rental Income: $3907 Airbnb ROI: -0.47% Traditional ROI: 2.47%
381 Clinton Street #5200 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: -0.41% Traditional cash on cash: 2.9% Airbnb Rental Income: $1256 Traditional Rental Income: $3907 Airbnb ROI: -0.41% 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.	$599,900	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.62% Airbnb Rental Income: $1256 Traditional Rental Income: $3423 Airbnb ROI: -0.96% Traditional ROI: 3.62%
545 A Street Ashland, OR Versatile mixed-use commercial and residential building with strong rental history in Ashl...	N/A beds \| N/A baths \| 4,950 sq.ft.	$1,250,000	Airbnb cash on cash: -1.56% Traditional cash on cash: -0.73% Airbnb Rental Income: $1045 Traditional Rental Income: $1639 Airbnb ROI: -1.56% Traditional ROI: -0.73%
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: 0.8% Traditional cash on cash: 6.34% Airbnb Rental Income: $2938 Traditional Rental Income: $6309 Airbnb ROI: 0.8% 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: -0.89% Traditional cash on cash: 0.93% Airbnb Rental Income: $1200 Traditional Rental Income: $1984 Airbnb ROI: -0.89% 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: 1.41% Traditional cash on cash: 4.14% Airbnb Rental Income: $2938 Traditional Rental Income: $4082 Airbnb ROI: 1.41% Traditional ROI: 4.14%
36 Dewey Street Ashland, OR Don't miss out on owning an amazing investment property in Ashland, Oregon. This 6-unit pr...	N/A beds \| N/A baths \| 2,416 sq.ft.	$849,900	Airbnb cash on cash: -0.68% Traditional cash on cash: 0.66% Airbnb Rental Income: $1045 Traditional Rental Income: $1742 Airbnb ROI: -0.68% Traditional ROI: 0.66%
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: -0.37% Traditional cash on cash: 5.83% Airbnb Rental Income: $1256 Traditional Rental Income: $4187 Airbnb ROI: -0.37% Traditional ROI: 5.83%
270 Morton Street Ashland, OR Set on a private corner lot just minutes from downtown Ashland, this unique property offer...	3 beds \| 3 baths \| 1,715 sq.ft.	$688,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 3.56% Airbnb Rental Income: $1256 Traditional Rental Income: $3486 Airbnb ROI: -0.54% Traditional ROI: 3.56%

Real Estate investment in Ashland, OR

There are 102 properties for sale in the city of Ashland . The median list price in Ashland is $620,000 and the average price per square foot is $278. In June 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,096.

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

There are 102 investment properties available for sale in Ashland.

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

The ROI for Short-Term is higher than the Long-Term in Ashland with average rental income of $1,256.

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: -1.63%

Traditional cash on cash: 1.36%

Airbnb Rental Income: $1256

Traditional Rental Income: $4331

Airbnb ROI: -1.63%

Traditional ROI: 1.36%

610 Orchard Street

Ashland, OR

5 beds | 3 baths | 3,458 sq.ft.

$989,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.21%

Airbnb Rental Income: $null

Traditional Rental Income: $4953

Airbnb ROI: N/A

Traditional ROI: 3.21%

740 Park Street

Ashland, OR

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

$534,000

Airbnb cash on cash: -0.38%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $1256

Traditional Rental Income: $2751

Airbnb ROI: -0.38%

Traditional ROI: 3.41%

271 Cove Road

Ashland, OR

4 beds | 4 baths | 3,299 sq.ft.

$1,590,000

Airbnb cash on cash: 0.32%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $2938

Traditional Rental Income: $5568

Airbnb ROI: 0.32%

Traditional ROI: 2.56%

496 Beach Street

Ashland, OR

5 beds | 6 baths | 3,647 sq.ft.

$935,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.45%

Airbnb Rental Income: $null

Traditional Rental Income: $8631

Airbnb ROI: N/A

Traditional ROI: 7.45%

1084 E Main Street

Ashland, OR

3 beds | 2 baths | 1,286 sq.ft.

$500,000

Airbnb cash on cash: -0.44%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1256

Traditional Rental Income: $2793

Airbnb ROI: -0.44%

Traditional ROI: 3.7%

7130 Highway 66

Ashland, OR

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

$1,140,000

Airbnb cash on cash: -1.03%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $1256

Traditional Rental Income: $4254

Airbnb ROI: -1.03%

Traditional ROI: 2.17%

694 Timberlake Drive

Ashland, OR

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

$599,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 4.64%

Airbnb Rental Income: $1256

Traditional Rental Income: $3811

Airbnb ROI: -0.65%