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
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.	$899,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.27% Airbnb Rental Income: $968 Traditional Rental Income: $3579 Airbnb ROI: -1.27% Traditional ROI: 2.27%
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: -1.02% Traditional cash on cash: 3.41% Airbnb Rental Income: $873 Traditional Rental Income: $2751 Airbnb ROI: -1.02% Traditional ROI: 3.41%
58 N Mountain Avenue Ashland, OR Elegant condominium with a thoughtfully designed open-concept layout. The main living area...	3 beds \| 3 baths \| 1,510 sq.ft.	$425,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 5.54% Airbnb Rental Income: $873 Traditional Rental Income: $3102 Airbnb ROI: -0.9% Traditional ROI: 5.54%
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: -0.79% Traditional cash on cash: 2.56% Airbnb Rental Income: $968 Traditional Rental Income: $5568 Airbnb ROI: -0.79% 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: -1.8% Traditional cash on cash: 7.45% Airbnb Rental Income: $921 Traditional Rental Income: $8631 Airbnb ROI: -1.8% Traditional ROI: 7.45%
325 Taylor Street Ashland, OR Charming modern home with an open and inviting layout. The kitchen flows seamlessly into t...	3 beds \| 2 baths \| 1,205 sq.ft.	$550,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 3.37% Airbnb Rental Income: $873 Traditional Rental Income: $2840 Airbnb ROI: -1.11% Traditional ROI: 3.37%
295 Tolman Creek Road unit: #1 Ashland, OR Well-maintained, ground-level, accessible Ashland condominium offering a convenient locati...	2 beds \| 2 baths \| 988 sq.ft.	$299,500	Airbnb cash on cash: -0.9% Traditional cash on cash: 5.74% Airbnb Rental Income: $1028 Traditional Rental Income: $2541 Airbnb ROI: -0.9% Traditional ROI: 5.74%
10 Velna Way Ashland, OR Single-level home on private acreage with mature oaks and seasonal creek, located in a pri...	3 beds \| 2 baths \| 1,860 sq.ft.	$715,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 3.13% Airbnb Rental Income: $873 Traditional Rental Income: $3265 Airbnb ROI: -0.96% Traditional ROI: 3.13%
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: -0.99% Traditional cash on cash: 3.47% Airbnb Rental Income: $873 Traditional Rental Income: $3654 Airbnb ROI: -0.99% Traditional ROI: 3.47%
854 Twin Pines Circle unit: 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: -0.87% Traditional cash on cash: 2.14% Airbnb Rental Income: $1028 Traditional Rental Income: $1377 Airbnb ROI: -0.87% Traditional ROI: 2.14%
138 Clear Creek Drive Ashland, OR Prime location is Ashland's highly desirable Railroad District/Spur Rail Subdivision. Fant...	2 beds \| 4 baths \| 3,070 sq.ft.	$1,466,000	Airbnb cash on cash: -0.88% Traditional cash on cash: 0.52% Airbnb Rental Income: $1028 Traditional Rental Income: $2565 Airbnb ROI: -0.88% Traditional ROI: 0.52%
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: -0.79% Traditional cash on cash: 0.38% Airbnb Rental Income: $932 Traditional Rental Income: $1518 Airbnb ROI: -0.79% Traditional ROI: 0.38%
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: -1.49% Traditional cash on cash: 0.53% Airbnb Rental Income: $968 Traditional Rental Income: $6711 Airbnb ROI: -1.49% Traditional ROI: 0.53%
988 Dead Indian Memorial Road Ashland, OR Nestled on 5.35 acres, this gorgeous Tuscan-style home offers stunning scenery and peacefu...	3 beds \| 3 baths \| 4,668 sq.ft.	$1,495,000	Airbnb cash on cash: -1.37% Traditional cash on cash: 0.8% Airbnb Rental Income: $873 Traditional Rental Income: $3556 Airbnb ROI: -1.37% Traditional ROI: 0.8%
2299 Siskiyou Boulevard Ashland, OR Charming and conveniently located home just steps from Creekside Cottages community acreag...	1 beds \| 1 baths \| 983 sq.ft.	$350,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 3.35% Airbnb Rental Income: $807 Traditional Rental Income: $2148 Airbnb ROI: -1.71% Traditional ROI: 3.35%
2809 DEAD INDIAN MEMORIAL Rd Ashland, OR Experience refined country living on just over 23 acres of rolling green hills, and panora...	3 beds \| 3 baths \| 2,530 sq.ft.	$850,000	Airbnb cash on cash: -1.22% Traditional cash on cash: 2.49% Airbnb Rental Income: $873 Traditional Rental Income: $3471 Airbnb ROI: -1.22% Traditional ROI: 2.49%
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.	$949,900	Airbnb cash on cash: -0.78% Traditional cash on cash: 2.78% Airbnb Rental Income: $873 Traditional Rental Income: $3687 Airbnb ROI: -0.78% Traditional ROI: 2.78%
30 Steinman Drive Ashland, OR Peaceful mountain retreat with sweeping views and abundant natural light from expansive pi...	3 beds \| 3 baths \| 2,639 sq.ft.	$595,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 5.09% Airbnb Rental Income: $873 Traditional Rental Income: $4090 Airbnb ROI: -1.3% Traditional ROI: 5.09%
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: -0.71% Traditional cash on cash: 3.94% Airbnb Rental Income: $873 Traditional Rental Income: $2605 Airbnb ROI: -0.71% 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: -0.61% Traditional cash on cash: 2.73% Airbnb Rental Income: $1028 Traditional Rental Income: $2321 Airbnb ROI: -0.61% Traditional ROI: 2.73%
583 Coffee Lane Ashland, OR Discover the beauty of simple, sustainable living w/smart investment potential in this mod...	2 beds \| 1 baths \| 752 sq.ft.	$404,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.24% Airbnb Rental Income: $1028 Traditional Rental Income: $2116 Airbnb ROI: -0.58% Traditional ROI: 3.24%
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.	$1,900,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 2.23% Airbnb Rental Income: $921 Traditional Rental Income: $8347 Airbnb ROI: -2.18% Traditional ROI: 2.23%
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.	$575,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 5.03% Airbnb Rental Income: $968 Traditional Rental Income: $3827 Airbnb ROI: -0.95% Traditional ROI: 5.03%
571 S Mountain Avenue Ashland, OR Perched above the university in a prime central location, this bright and inviting 3 bedro...	3 beds \| 2 baths \| 2,052 sq.ft.	$589,900	Airbnb cash on cash: -1.12% Traditional cash on cash: 3.9% Airbnb Rental Income: $873 Traditional Rental Income: $3305 Airbnb ROI: -1.12% Traditional ROI: 3.9%
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.	$4,400,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.34% Airbnb Rental Income: $921 Traditional Rental Income: $7515 Airbnb ROI: -1.36% Traditional ROI: 0.34%
185 Almond Street Ashland, OR Spacious, inviting home in the heart of Ashland on peaceful Almond Street, less than a hal...	4 beds \| 4 baths \| 2,698 sq.ft.	$775,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 4.52% Airbnb Rental Income: $968 Traditional Rental Income: $4770 Airbnb ROI: -1.23% Traditional ROI: 4.52%
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.	$535,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 3.3% Airbnb Rental Income: $1028 Traditional Rental Income: $2685 Airbnb ROI: -0.74% Traditional ROI: 3.3%
1015 Oneida Circle Ashland, OR Charming home with treehouse-like feel on a spacious corner lot with mature trees in a des...	3 beds \| 2 baths \| 1,590 sq.ft.	$500,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 4.51% Airbnb Rental Income: $873 Traditional Rental Income: $3182 Airbnb ROI: -1.14% Traditional ROI: 4.51%
1259 Hagen Way Ashland, OR 1259 Hagen is the kind of home that just makes sense, modern, efficient, and designed for ...	3 beds \| 2 baths \| 1,526 sq.ft.	$725,000	Airbnb cash on cash: -1.52% Traditional cash on cash: 2.48% Airbnb Rental Income: $873 Traditional Rental Income: $3242 Airbnb ROI: -1.52% Traditional ROI: 2.48%
794 Park Street Ashland, OR Comfortable living in this single level, stand-alone cottage style home. Built in 2002, th...	2 beds \| 2 baths \| 1,003 sq.ft.	$354,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 4.99% Airbnb Rental Income: $1028 Traditional Rental Income: $2713 Airbnb ROI: -1.16% Traditional ROI: 4.99%
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: -1.43% Traditional cash on cash: 3.46% Airbnb Rental Income: $921 Traditional Rental Income: $6917 Airbnb ROI: -1.43% Traditional ROI: 3.46%
391 Clinton Street unit: 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: -0.78% Traditional cash on cash: 2.47% Airbnb Rental Income: $873 Traditional Rental Income: $3907 Airbnb ROI: -0.78% Traditional ROI: 2.47%
381 Clinton Street unit: 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: -0.75% Traditional cash on cash: 2.9% Airbnb Rental Income: $873 Traditional Rental Income: $3907 Airbnb ROI: -0.75% 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: -1.53% Traditional cash on cash: 3.62% Airbnb Rental Income: $873 Traditional Rental Income: $3423 Airbnb ROI: -1.53% Traditional ROI: 3.62%
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.	$815,000	Airbnb cash on cash: -1.42% Traditional cash on cash: 6.07% Airbnb Rental Income: $968 Traditional Rental Income: $6309 Airbnb ROI: -1.42% Traditional ROI: 6.07%
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: -1.11% Traditional cash on cash: 0.93% Airbnb Rental Income: $1028 Traditional Rental Income: $1984 Airbnb ROI: -1.11% 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.	$744,000	Airbnb cash on cash: -1.05% Traditional cash on cash: 3.95% Airbnb Rental Income: $968 Traditional Rental Income: $4082 Airbnb ROI: -1.05% Traditional ROI: 3.95%
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: -0.79% Traditional cash on cash: 0.66% Airbnb Rental Income: $932 Traditional Rental Income: $1742 Airbnb ROI: -0.79% 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.	$600,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 5.55% Airbnb Rental Income: $873 Traditional Rental Income: $4187 Airbnb ROI: -0.96% Traditional ROI: 5.55%
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: -1.04% Traditional cash on cash: 3.56% Airbnb Rental Income: $873 Traditional Rental Income: $3486 Airbnb ROI: -1.04% Traditional ROI: 3.56%

Real Estate investment in Ashland, OR

There are 101 properties for sale in the city of Ashland . The median list price in Ashland is $599,900 and the average price per square foot is $291. In April 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,120.

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

There are 101 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 $3,120.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

774 Lisa Lane

Ashland, OR

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

$899,000

Airbnb cash on cash: -1.27%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $968

Traditional Rental Income: $3579

Airbnb ROI: -1.27%

Traditional ROI: 2.27%

740 Park Street

Ashland, OR

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

$534,000

Airbnb cash on cash: -1.02%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $873

Traditional Rental Income: $2751

Airbnb ROI: -1.02%

Traditional ROI: 3.41%

58 N Mountain Avenue

Ashland, OR

3 beds | 3 baths | 1,510 sq.ft.

$425,000

Airbnb cash on cash: -0.9%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $873

Traditional Rental Income: $3102

Airbnb ROI: -0.9%

Traditional ROI: 5.54%

271 Cove Road

Ashland, OR

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

$1,590,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: 2.56%

Airbnb Rental Income: $968

Traditional Rental Income: $5568

Airbnb ROI: -0.79%

Traditional ROI: 2.56%

496 Beach Street

Ashland, OR

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

$935,000

Airbnb cash on cash: -1.8%

Traditional cash on cash: 7.45%

Airbnb Rental Income: $921

Traditional Rental Income: $8631

Airbnb ROI: -1.8%

Traditional ROI: 7.45%

325 Taylor Street

Ashland, OR

3 beds | 2 baths | 1,205 sq.ft.

$550,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 3.37%

Airbnb Rental Income: $873

Traditional Rental Income: $2840

Airbnb ROI: -1.11%

Traditional ROI: 3.37%

295 Tolman Creek Road unit: #1

Ashland, OR

2 beds | 2 baths | 988 sq.ft.

$299,500

Airbnb cash on cash: -0.9%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $1028

Traditional Rental Income: $2541

Airbnb ROI: -0.9%

Traditional ROI: 5.74%

10 Velna Way

Ashland, OR

3 beds | 2 baths | 1,860 sq.ft.

$715,000

Airbnb cash on cash: -0.96%

Traditional cash on cash: 3.13%

Airbnb Rental Income: $873

Traditional Rental Income: $3265

Airbnb ROI: -0.96%