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
1070 Emma Street Ashland, OR Nestled in the trees above SOU, this home has the grace of large trees and mature landscap...	5 beds \| 5 baths \| 2,839 sq.ft.	$775,000	Airbnb cash on cash: 4.84% Traditional cash on cash: 6.34% Airbnb Rental Income: $6259 Traditional Rental Income: $6108 Airbnb ROI: 4.84% Traditional ROI: 6.34%
354 Garfield Street Ashland, OR Charming single-level midcentury bungalow on a spacious and centrally located R-2 zoned lo...	3 beds \| 2 baths \| 1,168 sq.ft.	$450,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.98% Airbnb Rental Income: $3917 Traditional Rental Income: $2930 Airbnb ROI: 5.33% Traditional ROI: 4.98%
481 Lindsay Lane Ashland, OR Lindsay Lane warms your heart on cool December evenings with a gorgeous gas fireplace and ...	3 beds \| 3 baths \| 2,783 sq.ft.	$800,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 3.29% Airbnb Rental Income: $3917 Traditional Rental Income: $4090 Airbnb ROI: 1.93% Traditional ROI: 3.29%
839 Roca Street Ashland, OR Wonderful mid-century modern home featuring a tiled entryway, panoramic-like windows, and ...	3 beds \| 3 baths \| 2,485 sq.ft.	$650,000	Airbnb cash on cash: 2.99% Traditional cash on cash: 4.89% Airbnb Rental Income: $3917 Traditional Rental Income: $4227 Airbnb ROI: 2.99% Traditional ROI: 4.89%
970 Elkader Street Ashland, OR Enchanting custom home on rare private acreage within city limits - centrally located abov...	3 beds \| 2 baths \| 2,096 sq.ft.	$850,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 2.75% Airbnb Rental Income: $3917 Traditional Rental Income: $3722 Airbnb ROI: 1.94% Traditional ROI: 2.75%
908 Mountain Meadows Circle Ashland, OR Experience the best of Ashland living in this light, bright, well-maintained home in South...	3 beds \| 2 baths \| 1,634 sq.ft.	$350,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 3.33% Airbnb Rental Income: $3917 Traditional Rental Income: $3602 Airbnb ROI: 1.73% Traditional ROI: 3.33%
690 Spring Creek Drive Ashland, OR Discover tranquility at 690 Spring Creek! Situated on 1.4 acres within city limits, this c...	3 beds \| 2 baths \| 1,842 sq.ft.	$600,000	Airbnb cash on cash: 3.3% Traditional cash on cash: 2.02% Airbnb Rental Income: $3917 Traditional Rental Income: $2354 Airbnb ROI: 3.3% Traditional ROI: 2.02%
495 Chestnut Street #4 Ashland, OR Low-maintenance condominium across from Asante Ashland Community Hospital, less than three...	2 beds \| 2 baths \| 832 sq.ft.	$250,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 6.44% Airbnb Rental Income: $3602 Traditional Rental Income: $2347 Airbnb ROI: 8.41% Traditional ROI: 6.44%
508 N Main Street Ashland, OR LOOKING FOR POSSIBILITIES?... CLASSIC VICTORIAN AS UNIQUE AS ASHLAND. This charming home o...	3 beds \| 2 baths \| 1,498 sq.ft.	$529,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 4.26% Airbnb Rental Income: $3917 Traditional Rental Income: $3194 Airbnb ROI: 4.02% Traditional ROI: 4.26%
4896 Highway 66 Ashland, OR Located on 5 acres, this home is constructed to the highest standards. There is simply no ...	4 beds \| 3 baths \| 3,361 sq.ft.	$1,850,000	Airbnb cash on cash: 3.06% Traditional cash on cash: 0.75% Airbnb Rental Income: $10022 Traditional Rental Income: $4200 Airbnb ROI: 3.06% Traditional ROI: 0.75%
99 Granite Street Ashland, OR This extraordinary Greene and Greene inspired Craftsman home will not disappoint. No expen...	4 beds \| 9 baths \| 6,903 sq.ft.	$3,800,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 0.21% Airbnb Rental Income: $10022 Traditional Rental Income: $6662 Airbnb ROI: 0.64% Traditional ROI: 0.21%
720 Salishan Court Ashland, OR Looking for a conveniently located home in a secluded cul-de-sac and vibrant community? Th...	3 beds \| 2 baths \| 1,331 sq.ft.	$465,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 4.17% Airbnb Rental Income: $3917 Traditional Rental Income: $2804 Airbnb ROI: 4.79% Traditional ROI: 4.17%
1501 Jackson Road Ashland, OR Welcome to your dream horse property! Step onto the property and be taken away by breathta...	3 beds \| 3 baths \| 3,904 sq.ft.	$1,257,500	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.7% Airbnb Rental Income: $3917 Traditional Rental Income: $4132 Airbnb ROI: 0.79% Traditional ROI: 1.7%
3403 N Valley View Road Ashland, OR Own a piece of Ashland hillside paradise! 139 acres zoned EFU, with sweeping views of the...	3 beds \| 3 baths \| 3,624 sq.ft.	$849,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.93% Airbnb Rental Income: $3917 Traditional Rental Income: $4262 Airbnb ROI: 2.43% Traditional ROI: 3.93%
1249 N Valley View Road Ashland, OR Beautiful property in Ashland with Panoramic views! 3 Tax Lots total 13.39 acres, all wit...	2 beds \| 2 baths \| 1,160 sq.ft.	$925,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 1.76% Airbnb Rental Income: $3602 Traditional Rental Income: $2825 Airbnb ROI: 1.74% Traditional ROI: 1.76%
135 Maywood Way Ashland, OR Beautifully remodeled like-new Craftsman farmhouse with separate buildable tax lot just mi...	4 beds \| 3 baths \| 2,008 sq.ft.	$775,000	Airbnb cash on cash: 9.67% Traditional cash on cash: 1.86% Airbnb Rental Income: $10022 Traditional Rental Income: $2516 Airbnb ROI: 9.67% Traditional ROI: 1.86%
961 Pinecrest Terrace Ashland, OR New single-level Earth Advantage certified home in the Ashland hills. This contemporary ho...	4 beds \| 2 baths \| 2,005 sq.ft.	$969,000	Airbnb cash on cash: 7.72% Traditional cash on cash: 2.82% Airbnb Rental Income: $10022 Traditional Rental Income: $3743 Airbnb ROI: 7.72% Traditional ROI: 2.82%
2086 Creek Drive Ashland, OR One of the highlights of the property is the stunning panoramic meadow views that can be e...	3 beds \| 3 baths \| 1,973 sq.ft.	$515,000	Airbnb cash on cash: 3.84% Traditional cash on cash: 5.39% Airbnb Rental Income: $3917 Traditional Rental Income: $3819 Airbnb ROI: 3.84% Traditional ROI: 5.39%
128 S Mountain Avenue Ashland, OR Great Investment Opportunity located close to downtown Ashland. Nicely maintained duplex w...	N/A beds \| N/A baths \| N/A	$855,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 0.4% Airbnb Rental Income: $3917 Traditional Rental Income: $1518 Airbnb ROI: 2.36% Traditional ROI: 0.4%
933 Mountain Meadows Circle Ashland, OR Looking for a carefree lifestyle? Welcome to the Mountain Meadows 55+ community! This 2 b...	2 beds \| 2 baths \| 1,278 sq.ft.	$224,900	Airbnb cash on cash: 2.67% Traditional cash on cash: 3.3% Airbnb Rental Income: $3602 Traditional Rental Income: $2948 Airbnb ROI: 2.67% Traditional ROI: 3.3%
813 Boulder Creek Lane Ashland, OR Don't miss this fantastic opportunity to own an end-unit, single-level condo in the highly...	2 beds \| 2 baths \| 1,431 sq.ft.	$305,000	Airbnb cash on cash: 2.54% Traditional cash on cash: 3.42% Airbnb Rental Income: $3602 Traditional Rental Income: $3066 Airbnb ROI: 2.54% Traditional ROI: 3.42%
1720 Colestin Road Ashland, OR Location, location, location! Looking for a move-in ready home close to Mt. Ashland? If so...	2 beds \| 2 baths \| 1,368 sq.ft.	$350,000	Airbnb cash on cash: 6.53% Traditional cash on cash: 7.12% Airbnb Rental Income: $3602 Traditional Rental Income: $3006 Airbnb ROI: 6.53% Traditional ROI: 7.12%
1283 Hagen Way #Lot 9 Ashland, OR New single-level Earth Advantage certified home in Ashland's new railroad district subdivi...	3 beds \| 2 baths \| 1,572 sq.ft.	$729,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 2.69% Airbnb Rental Income: $3917 Traditional Rental Income: $3253 Airbnb ROI: 2.43% Traditional ROI: 2.69%
1024 Pinecrest Terrace Ashland, OR Your Dream Life Awaits! Imagine waking up to breathtaking views, with each day beginning ...	3 beds \| 2 baths \| 3,142 sq.ft.	$850,000	Airbnb cash on cash: 1.87% Traditional cash on cash: 2.94% Airbnb Rental Income: $3917 Traditional Rental Income: $3928 Airbnb ROI: 1.87% Traditional ROI: 2.94%
575 Scenic Drive Ashland, OR This Ashland condominium has great mountain views, a couple of blocks to Ashland Hospital ...	3 beds \| 3 baths \| 1,660 sq.ft.	$349,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 6.87% Airbnb Rental Income: $3917 Traditional Rental Income: $3370 Airbnb ROI: 5.97% Traditional ROI: 6.87%
786 Pompadour Drive Ashland, OR Paradox Vineyard Estate is uniquely defined by elements of water, air, the natural light a...	4 beds \| 6 baths \| 5,233 sq.ft.	$4,500,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.13% Airbnb Rental Income: $10022 Traditional Rental Income: $6711 Airbnb ROI: 0.48% Traditional ROI: 0.13%
765 Reiten Drive Ashland, OR Bring your kids, animals, & even the in-laws to enjoy country living just 10 minutes from ...	3 beds \| 3 baths \| 4,338 sq.ft.	$699,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 3.13% Airbnb Rental Income: $3917 Traditional Rental Income: $3547 Airbnb ROI: 2.41% Traditional ROI: 3.13%
704 Elkader Street Ashland, OR Incomparable Value above the Boulevard! Come experience this 5 bed, 3 bath pool home with ...	5 beds \| 3 baths \| 2,842 sq.ft.	$495,000	Airbnb cash on cash: 8.27% Traditional cash on cash: 5.43% Airbnb Rental Income: $6259 Traditional Rental Income: $3716 Airbnb ROI: 8.27% Traditional ROI: 5.43%
451 E Ashland Lane Ashland, OR Sought after 4100 sq.ft single level, country home on approx. 5 level irrigated acres with...	4 beds \| 4 baths \| 4,071 sq.ft.	$1,525,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 1.7% Airbnb Rental Income: $10022 Traditional Rental Income: $4446 Airbnb ROI: 4.32% Traditional ROI: 1.7%
349 Ravenwood Place Ashland, OR Welcome to this stunning split-level condo offering 1,392 square feet of modern living spa...	2 beds \| 2 baths \| 1,392 sq.ft.	$429,900	Airbnb cash on cash: 3.93% Traditional cash on cash: 4.27% Airbnb Rental Income: $3602 Traditional Rental Income: $2950 Airbnb ROI: 3.93% Traditional ROI: 4.27%
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.	$1,695,108	Airbnb cash on cash: 0.68% Traditional cash on cash: 1.06% Airbnb Rental Income: $3917 Traditional Rental Income: $3671 Airbnb ROI: 0.68% Traditional ROI: 1.06%
520 Helman Street Ashland, OR Immerse yourself in the Lithia Creekfront lifestyle. This 2,244SF single level home featur...	4 beds \| 2 baths \| 2,244 sq.ft.	$997,000	Airbnb cash on cash: 7.27% Traditional cash on cash: 2.06% Airbnb Rental Income: $10022 Traditional Rental Income: $3322 Airbnb ROI: 7.27% Traditional ROI: 2.06%
988 Dead Indian Memorial Road Ashland, OR Rare Ashland opportunity on a 5+ acre tax lot, close proximity to town, only 2 miles up DI...	4 beds \| 3 baths \| 4,668 sq.ft.	$1,500,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 0.81% Airbnb Rental Income: $10022 Traditional Rental Income: $3556 Airbnb ROI: 4.12% Traditional ROI: 0.81%
1388 Mill Pond Road Ashland, OR Cozy Ashland Craftsman-style cottage in the well-loved Mill Pond community. Walk to the gr...	3 beds \| 2 baths \| 1,100 sq.ft.	$519,000	Airbnb cash on cash: 4.44% Traditional cash on cash: 4.28% Airbnb Rental Income: $3917 Traditional Rental Income: $2994 Airbnb ROI: 4.44% Traditional ROI: 4.28%
1475 Dead Indian Memorial Road Ashland, OR Custom prairie style in a sought-after location just a mile outside of town. Gated entranc...	4 beds \| 4 baths \| 4,382 sq.ft.	$1,750,000	Airbnb cash on cash: 3.24% Traditional cash on cash: 0.76% Airbnb Rental Income: $10022 Traditional Rental Income: $4142 Airbnb ROI: 3.24% Traditional ROI: 0.76%
19015 Dead Indian Memorial Road Ashland, OR Lovely Oregon Horse Property! 30+ acres surrounded by BLM and US Forestry land giving you ...	3 beds \| 2 baths \| 2,624 sq.ft.	$975,000	Airbnb cash on cash: 2.1% Traditional cash on cash: 3.26% Airbnb Rental Income: $3917 Traditional Rental Income: $4130 Airbnb ROI: 2.1% Traditional ROI: 3.26%
721 N Main Street Ashland, OR Great investment opportunity. 12-plex - all two-bedroom one bath units. Solid build. Downs...	N/A beds \| N/A baths \| 9,480 sq.ft.	$1,800,000	Airbnb cash on cash: 2.95% Traditional cash on cash: -0.98% Airbnb Rental Income: $10022 Traditional Rental Income: $1609 Airbnb ROI: 2.95% Traditional ROI: -0.98%
597 Mariposa Court Ashland, OR Lovely Single-Level Mountain Meadows Condominium Home. Nestled in the heart of Ashland's r...	2 beds \| 2 baths \| 1,513 sq.ft.	$369,500	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.31% Airbnb Rental Income: $3602 Traditional Rental Income: $3430 Airbnb ROI: 1.53% Traditional ROI: 3.31%
565 Ashland Street Ashland, OR A unique opportunity with two seperate homes on one tax lot. The primary home is a well-a...	3 beds \| 2 baths \| 2,562 sq.ft.	$900,000	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.83% Airbnb Rental Income: $3917 Traditional Rental Income: $4039 Airbnb ROI: 1.68% Traditional ROI: 2.83%
256 Wimer Street Ashland, OR Discover the perfect blend of breathtaking views and serene privacy in this stunning home,...	4 beds \| 3 baths \| 2,608 sq.ft.	$869,000	Airbnb cash on cash: 8.01% Traditional cash on cash: 3.04% Airbnb Rental Income: $10022 Traditional Rental Income: $4140 Airbnb ROI: 8.01% Traditional ROI: 3.04%

Real Estate investment in Ashland, OR

There are 54 properties for sale in the city of Ashland . The median list price in Ashland is $637,500 and the average price per square foot is $257. In January 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,552.

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

There are 54 investment properties available for sale in Ashland.

In 2025, 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 $3,917.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

1070 Emma Street

Ashland, OR

5 beds | 5 baths | 2,839 sq.ft.

$775,000

Airbnb cash on cash: 4.84%

Traditional cash on cash: 6.34%

Airbnb Rental Income: $6259

Traditional Rental Income: $6108

Airbnb ROI: 4.84%

Traditional ROI: 6.34%

354 Garfield Street

Ashland, OR

3 beds | 2 baths | 1,168 sq.ft.

$450,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $3917

Traditional Rental Income: $2930

Airbnb ROI: 5.33%

Traditional ROI: 4.98%

481 Lindsay Lane

Ashland, OR

3 beds | 3 baths | 2,783 sq.ft.

$800,000

Airbnb cash on cash: 1.93%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $3917

Traditional Rental Income: $4090

Airbnb ROI: 1.93%

Traditional ROI: 3.29%

839 Roca Street

Ashland, OR

3 beds | 3 baths | 2,485 sq.ft.

$650,000

Airbnb cash on cash: 2.99%

Traditional cash on cash: 4.89%

Airbnb Rental Income: $3917

Traditional Rental Income: $4227

Airbnb ROI: 2.99%

Traditional ROI: 4.89%

970 Elkader Street

Ashland, OR

3 beds | 2 baths | 2,096 sq.ft.

$850,000

Airbnb cash on cash: 1.94%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $3917

Traditional Rental Income: $3722

Airbnb ROI: 1.94%

Traditional ROI: 2.75%

908 Mountain Meadows Circle

Ashland, OR

3 beds | 2 baths | 1,634 sq.ft.

$350,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 3.33%

Airbnb Rental Income: $3917

Traditional Rental Income: $3602

Airbnb ROI: 1.73%

Traditional ROI: 3.33%

690 Spring Creek Drive

Ashland, OR

3 beds | 2 baths | 1,842 sq.ft.

$600,000

Airbnb cash on cash: 3.3%

Traditional cash on cash: 2.02%

Airbnb Rental Income: $3917

Traditional Rental Income: $2354

Airbnb ROI: 3.3%

Traditional ROI: 2.02%

495 Chestnut Street #4

Ashland, OR

2 beds | 2 baths | 832 sq.ft.

$250,000

Airbnb cash on cash: 8.41%

Traditional cash on cash: 6.44%

Airbnb Rental Income: $3602

Traditional Rental Income: $2347

Airbnb ROI: 8.41%