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
435 Friendship Street Ashland, OR Located at the end of a peaceful cul-de-sac in the Ashland Hills, this 4 bedroom, 3 bathr...	4 beds \| 3 baths \| 2,496 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $3964 Airbnb ROI: N/A Traditional ROI: 4.62%
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.	$500,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.39% Airbnb Rental Income: $null Traditional Rental Income: $2930 Airbnb ROI: N/A Traditional ROI: 4.39%
481 Lindsay Lane Ashland, OR This Billings Ranch Home welcomes you with oversized windows and stunning chestnut wood fl...	3 beds \| 3 baths \| 2,783 sq.ft.	$800,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $4090 Airbnb ROI: N/A Traditional ROI: 3.29%
49 N Mountain Avenue Ashland, OR Exquisitely maintained, lightly lived in townhome with high end features including SS appl...	3 beds \| 2 baths \| 1,335 sq.ft.	$465,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.06% Airbnb Rental Income: $null Traditional Rental Income: $2986 Airbnb ROI: N/A Traditional ROI: 4.06%
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: N/A Traditional cash on cash: 4.89% Airbnb Rental Income: $null Traditional Rental Income: $4227 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.75% Airbnb Rental Income: $null Traditional Rental Income: $3722 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $3602 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.02% Airbnb Rental Income: $null Traditional Rental Income: $2354 Airbnb ROI: N/A Traditional ROI: 2.02%
767 Oak Street Ashland, OR This charming, modernized Victorian has it all! Close range to Ashland's downtown w/shoppi...	4 beds \| 5 baths \| 3,590 sq.ft.	$1,425,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.18% Airbnb Rental Income: $null Traditional Rental Income: $5279 Airbnb ROI: N/A Traditional ROI: 2.18%
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: N/A Traditional cash on cash: 6.44% Airbnb Rental Income: $null Traditional Rental Income: $2347 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 4.26% Airbnb Rental Income: $null Traditional Rental Income: $3194 Airbnb ROI: N/A Traditional ROI: 4.26%
270 N First Street Ashland, OR Located in the sought-after Railroad District and completely move in ready. This hard-to-f...	2 beds \| 3 baths \| 1,345 sq.ft.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3089 Airbnb ROI: N/A Traditional ROI: 3.75%
341 Meadow Drive Ashland, OR Check out this great house in a wonderful neighborhood! Features a generous kitchen, 4 bed...	4 beds \| 3 baths \| 2,038 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.44% Airbnb Rental Income: $null Traditional Rental Income: $3686 Airbnb ROI: N/A Traditional ROI: 4.44%
752 Terrace Street Ashland, OR Immaculate & Beautiful contemporary Northwest home 4 bdrm, 3 full baths. Many lg windows, ...	4 beds \| 3 baths \| 2,624 sq.ft.	$779,808	Airbnb cash on cash: N/A Traditional cash on cash: 3.45% Airbnb Rental Income: $null Traditional Rental Income: $4190 Airbnb ROI: N/A Traditional ROI: 3.45%
1900 Ashland Mine Road Ashland, OR A custom-built home with top-of-the-line systems and amenities, no expense was spared or d...	4 beds \| 5 baths \| 4,776 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $7416 Airbnb ROI: N/A Traditional ROI: 3.9%
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: N/A Traditional cash on cash: 0.75% Airbnb Rental Income: $null Traditional Rental Income: $4200 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 0.21% Airbnb Rental Income: $null Traditional Rental Income: $6662 Airbnb ROI: N/A Traditional ROI: 0.21%
5831 Old Highway 99 Ashland, OR Discover your dream property in the Siskiyou Mountains! Minutes to Mt. Ashland Ski Area, E...	3 beds \| 4 baths \| 2,953 sq.ft.	$1,217,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.81% Airbnb Rental Income: $null Traditional Rental Income: $3816 Airbnb ROI: N/A Traditional ROI: 1.81%
333 Granite Street Ashland, OR Located in prime neighborhood, 3/4 mile through adjacent Lithia Park to downtown restauran...	4 beds \| 4 baths \| 3,029 sq.ft.	$2,800,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.12% Airbnb Rental Income: $null Traditional Rental Income: $4243 Airbnb ROI: N/A Traditional ROI: 0.12%
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: N/A Traditional cash on cash: 1.7% Airbnb Rental Income: $null Traditional Rental Income: $4132 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $4262 Airbnb ROI: N/A 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.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.62% Airbnb Rental Income: $null Traditional Rental Income: $2825 Airbnb ROI: N/A Traditional ROI: 1.62%
3500 Siskiyou Boulevard Ashland, OR The location for this home is the best of both worlds with over 10 acres, privacy, 5 acres...	5 beds \| 3 baths \| 2,838 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.7% Airbnb Rental Income: $null Traditional Rental Income: $4166 Airbnb ROI: N/A Traditional ROI: 4.7%
965 Pinecrest Terrace Ashland, OR This elegant and modern home offers breathtaking views from above the boulevard yet is jus...	3 beds \| 3 baths \| 3,002 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.52% Airbnb Rental Income: $null Traditional Rental Income: $2627 Airbnb ROI: N/A Traditional ROI: 0.52%
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: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $2516 Airbnb ROI: N/A Traditional ROI: 1.86%
760 Creek Stone Way Ashland, OR This home is located in Ashland, OR's sought-after 55+ Mountain Meadows community, named t...	2 beds \| 2 baths \| 1,481 sq.ft.	$469,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.54% Airbnb Rental Income: $null Traditional Rental Income: $3044 Airbnb ROI: N/A Traditional ROI: 2.54%
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: N/A Traditional cash on cash: 2.82% Airbnb Rental Income: $null Traditional Rental Income: $3743 Airbnb ROI: N/A 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.	$539,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $3819 Airbnb ROI: N/A Traditional ROI: 5.1%
725 Clay Street Ashland, OR Beautiful Contemporary Stucco & Wood Home down a private paved lane with All City Services...	4 beds \| 3 baths \| 2,616 sq.ft.	$669,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.55% Airbnb Rental Income: $null Traditional Rental Income: $4207 Airbnb ROI: N/A Traditional ROI: 4.55%
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: N/A Traditional cash on cash: 0.4% Airbnb Rental Income: $null Traditional Rental Income: $1518 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2948 Airbnb ROI: N/A Traditional ROI: 3.3%
11266 Mt Ashland Ski Road Ashland, OR Location, location, location! Looking for a large home close to Mt Ashland? If so, this is...	4 beds \| 3 baths \| 2,446 sq.ft.	$535,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.94% Airbnb Rental Income: $null Traditional Rental Income: $3949 Airbnb ROI: N/A Traditional ROI: 5.94%
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: N/A Traditional cash on cash: 3.42% Airbnb Rental Income: $null Traditional Rental Income: $3066 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 7.12% Airbnb Rental Income: $null Traditional Rental Income: $3006 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 2.69% Airbnb Rental Income: $null Traditional Rental Income: $3253 Airbnb ROI: N/A Traditional ROI: 2.69%
682 Chestnut Street Ashland, OR Awesome income property just got better! A legal Duplex with 2 bedrooms each with approxim...	N/A beds \| N/A baths \| N/A	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.71% Airbnb Rental Income: $null Traditional Rental Income: $1515 Airbnb ROI: N/A Traditional ROI: 0.71%
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: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $3928 Airbnb ROI: N/A 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: N/A Traditional cash on cash: 6.87% Airbnb Rental Income: $null Traditional Rental Income: $3370 Airbnb ROI: N/A Traditional ROI: 6.87%
2101 Dead Indian Memorial Road Ashland, OR Located just three miles from downtown Ashland and below the snowline, you'll find this on...	5 beds \| 4 baths \| 3,378 sq.ft.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $4362 Airbnb ROI: N/A Traditional ROI: 2.51%
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: N/A Traditional cash on cash: 0.13% Airbnb Rental Income: $null Traditional Rental Income: $6711 Airbnb ROI: N/A Traditional ROI: 0.13%

Real Estate investment in Ashland, OR

There are 88 properties for sale in the city of Ashland . The median list price in Ashland is $650,000 and the average price per square foot is $263. In November 2024, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,591.

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

There are 88 investment properties available for sale in Ashland.

In 2024, 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 $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

435 Friendship Street

Ashland, OR

4 beds | 3 baths | 2,496 sq.ft.

$625,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3964

Airbnb ROI: N/A

Traditional ROI: 4.62%

354 Garfield Street

Ashland, OR

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

$500,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.39%

Airbnb Rental Income: $null

Traditional Rental Income: $2930

Airbnb ROI: N/A

Traditional ROI: 4.39%

481 Lindsay Lane

Ashland, OR

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

$800,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.29%

Airbnb Rental Income: $null

Traditional Rental Income: $4090

Airbnb ROI: N/A

Traditional ROI: 3.29%

49 N Mountain Avenue

Ashland, OR

3 beds | 2 baths | 1,335 sq.ft.

$465,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.06%

Airbnb Rental Income: $null

Traditional Rental Income: $2986

Airbnb ROI: N/A

Traditional ROI: 4.06%

839 Roca Street

Ashland, OR

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

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.89%

Airbnb Rental Income: $null

Traditional Rental Income: $4227

Airbnb ROI: N/A

Traditional ROI: 4.89%

970 Elkader Street

Ashland, OR

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

$850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.75%

Airbnb Rental Income: $null

Traditional Rental Income: $3722

Airbnb ROI: N/A

Traditional ROI: 2.75%

908 Mountain Meadows Circle

Ashland, OR

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

$350,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.33%

Airbnb Rental Income: $null

Traditional Rental Income: $3602

Airbnb ROI: N/A

Traditional ROI: 3.33%

690 Spring Creek Drive

Ashland, OR

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

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.02%

Airbnb Rental Income: $null

Traditional Rental Income: $2354

Airbnb ROI: N/A