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.	$1,395,808	Airbnb cash on cash: N/A Traditional cash on cash: 1.12% Airbnb Rental Income: $null Traditional Rental Income: $4331 Airbnb ROI: N/A Traditional ROI: 1.12%
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 \| 2,944 sq.ft.	$929,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.17% Airbnb Rental Income: $null Traditional Rental Income: $3579 Airbnb ROI: N/A Traditional ROI: 2.17%
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.	$544,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.33% Airbnb Rental Income: $null Traditional Rental Income: $2751 Airbnb ROI: N/A Traditional ROI: 3.33%
1369 Tolman Creek Road Ashland, OR Style meets sophistication with this stunning contemporary style home on a private shared ...	4 beds \| 3 baths \| 2,720 sq.ft.	$1,089,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $4376 Airbnb ROI: N/A Traditional ROI: 2.28%
802 Park Street Ashland, OR Fantastic opportunity to enjoy the Ashland lifestyle at an affordable price! This quiet co...	2 beds \| 2 baths \| 960 sq.ft.	$299,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $1960 Airbnb ROI: N/A Traditional ROI: 3.28%
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: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $5568 Airbnb ROI: N/A 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%
295 Tolman Creek Road #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: N/A Traditional cash on cash: 5.74% Airbnb Rental Income: $null Traditional Rental Income: $2541 Airbnb ROI: N/A 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.	$720,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.1% Airbnb Rental Income: $null Traditional Rental Income: $3265 Airbnb ROI: N/A Traditional ROI: 3.1%
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.	$265,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $1377 Airbnb ROI: N/A Traditional ROI: 1.96%
2130 Siskiyou Boulevard Ashland, OR Desirable end unit and great location, as well as being in a well-maintained community at ...	3 beds \| 3 baths \| 1,633 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.71% Airbnb Rental Income: $null Traditional Rental Income: $3305 Airbnb ROI: N/A Traditional ROI: 5.71%
2101 Dead Indian Memorial Road Ashland, OR Experience the ultimate Ashland lifestyle at this remarkable 5-acre estate, located just t...	5 beds \| 4 baths \| 3,018 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $4362 Airbnb ROI: N/A Traditional ROI: 3.49%
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.	$3,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.53% Airbnb Rental Income: $null Traditional Rental Income: $6711 Airbnb ROI: N/A Traditional ROI: 0.53%
1475 Dead Indian Memorial Road Ashland, OR Discover refined country living on nearly 25 private, gated acres just minutes from downto...	4 beds \| 4 baths \| 4,382 sq.ft.	$1,595,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.9% Airbnb Rental Income: $null Traditional Rental Income: $4142 Airbnb ROI: N/A Traditional ROI: 0.9%
124 Morton Street Ashland, OR Discover timeless charm in this historic and fully furnished two-unit farmhouse, completed...	N/A beds \| N/A baths \| N/A	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.98% Airbnb Rental Income: $null Traditional Rental Income: $1546 Airbnb ROI: N/A Traditional ROI: 0.98%
923 Mountain Meadows Circle Ashland, OR Beautifully maintained ground-level Parkside Condominium with abundant natural light near ...	1 beds \| 1 baths \| 731 sq.ft.	$150,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.04% Airbnb Rental Income: $null Traditional Rental Income: $2154 Airbnb ROI: N/A Traditional ROI: -0.04%
2299 Siskiyou Boulevard Ashland, OR Charming and conveniently located home just steps from Creekside Cottages community acreag...	1 beds \| 1 baths \| 882 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $2148 Airbnb ROI: N/A Traditional ROI: 3.38%
1620 Butler Creek Road Ashland, OR East Ashland hills dream! This 3-bed, 2-bath home set on 62.19 acres of irrigated land is ...	3 beds \| 2 baths \| 1,298 sq.ft.	$1,569,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.26% Airbnb Rental Income: $null Traditional Rental Income: $2461 Airbnb ROI: N/A Traditional ROI: 0.26%
2000 Colestin Road Ashland, OR Beautiful Colestin property on 189 acres with 5 separate lots combined, seasonal creek run...	1 beds \| 2 baths \| 460 sq.ft.	$875,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.64% Airbnb Rental Income: $null Traditional Rental Income: $1668 Airbnb ROI: N/A Traditional ROI: 0.64%
2809 DEAD INDIAN MEMORIAL Rd Ashland, OR Experience refined country living on just over 23 acres of rolling green hills, and panora...	3 beds \| 2 baths \| 2,530 sq.ft.	$880,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.37% Airbnb Rental Income: $null Traditional Rental Income: $3471 Airbnb ROI: N/A Traditional ROI: 2.37%
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: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $2605 Airbnb ROI: N/A 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.	$550,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $2321 Airbnb ROI: N/A Traditional ROI: 2.59%
5560 E Hyatt Lake Road #Cabin 2A Ashland, OR Imagine warm summer afternoons on the shores of Hyatt Lake, the water gently lapping at yo...	1 beds \| N/A baths \| 452 sq.ft.	$225,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $1776 Airbnb ROI: N/A Traditional ROI: 6.3%
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.	$409,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $2116 Airbnb ROI: N/A Traditional ROI: 3.19%
309 GRANITE St Ashland, OR Addressed as 309 and 311 Granite Street, this exceptional estate is tucked above Lithia Pa...	5 beds \| 3 baths \| 5,488 sq.ft.	$1,900,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.23% Airbnb Rental Income: $null Traditional Rental Income: $8347 Airbnb ROI: N/A Traditional ROI: 2.23%
759 S Mountain Avenue Ashland, OR A rare opportunity in one of Ashland's most sought-after neighborhoods! Just above Souther...	2 beds \| 1 baths \| 900 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $2211 Airbnb ROI: N/A Traditional ROI: 3.28%
376 Crowson Road Ashland, OR This is your opportunity to own a Multi Family income property on 4.13 acres! This versati...	3 beds \| 2 baths \| 2,574 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $4283 Airbnb ROI: N/A Traditional ROI: 4.4%
5010 Old Hwy 99 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: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2685 Airbnb ROI: N/A Traditional ROI: 3.3%
753 Siskiyou Boulevard Ashland, OR Historic home on a spacious lot with ~121 feet of alley access -- centrally located across...	4 beds \| 1 baths \| 1,380 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.5% Airbnb Rental Income: $null Traditional Rental Income: $2384 Airbnb ROI: N/A Traditional ROI: 3.5%
117 High Street Ashland, OR Extensively updated historic home located within three blocks of Ashland's downtown plaza ...	3 beds \| 2 baths \| 2,499 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.4% Airbnb Rental Income: $null Traditional Rental Income: $3554 Airbnb ROI: N/A Traditional ROI: 2.4%
551 Strawberry Lane Ashland, OR French provincial-inspired custom home located directly above Hald-Strawberry Park, just f...	3 beds \| 4 baths \| 4,435 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $4314 Airbnb ROI: N/A Traditional ROI: 1.55%
738 Fairway Court Ashland, OR Here is your chance to own one of the first homes built on the Oak Knoll golf course over ...	3 beds \| 3 baths \| 1,995 sq.ft.	$840,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.67% Airbnb Rental Income: $null Traditional Rental Income: $3659 Airbnb ROI: N/A Traditional ROI: 2.67%
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.	$369,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.75% Airbnb Rental Income: $null Traditional Rental Income: $2713 Airbnb ROI: N/A Traditional ROI: 4.75%
391 Clinton Street #5200 Ashland, OR Stunning new construction in Ashland's Magnolia Meadows! This exceptional 3-bedroom home ...	3 beds \| 3 baths \| 2,360 sq.ft.	$1,111,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $3907 Airbnb ROI: N/A Traditional ROI: 2.47%
94 N 3rd Street Ashland, OR Fantastic downtown Ashland location with curb appeal! This 2- bedroom, w/den-office & one...	2 beds \| 1 baths \| 1,248 sq.ft.	$509,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $2481 Airbnb ROI: N/A Traditional ROI: 2.84%
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: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $3907 Airbnb ROI: N/A 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.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.44% Airbnb Rental Income: $null Traditional Rental Income: $3423 Airbnb ROI: N/A Traditional ROI: 3.44%
3152 Siskiyou Boulevard Ashland, OR Imagine creating your dream farm on 28+ acres of EFU farmland, surrounded by breathtaking ...	2 beds \| 3 baths \| 2,007 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $3931 Airbnb ROI: N/A Traditional ROI: 3.3%
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: N/A Traditional cash on cash: 6.07% Airbnb Rental Income: $null Traditional Rental Income: $6309 Airbnb ROI: N/A 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.	$769,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.74% Airbnb Rental Income: $null Traditional Rental Income: $1984 Airbnb ROI: N/A Traditional ROI: 0.74%

Real Estate investment in Ashland, OR

There are 90 properties for sale in the city of Ashland . The median list price in Ashland is $615,000 and the average price per square foot is $309. In March 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,001.

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

There are 90 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 $N/A.

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.

$1,395,808

Airbnb cash on cash: N/A

Traditional cash on cash: 1.12%

Airbnb Rental Income: $null

Traditional Rental Income: $4331

Airbnb ROI: N/A

Traditional ROI: 1.12%

774 Lisa Lane

Ashland, OR

4 beds | 4 baths | 2,944 sq.ft.

$929,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.17%

Airbnb Rental Income: $null

Traditional Rental Income: $3579

Airbnb ROI: N/A

Traditional ROI: 2.17%

740 Park Street

Ashland, OR

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

$544,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.33%

Airbnb Rental Income: $null

Traditional Rental Income: $2751

Airbnb ROI: N/A

Traditional ROI: 3.33%

1369 Tolman Creek Road

Ashland, OR

4 beds | 3 baths | 2,720 sq.ft.

$1,089,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.28%

Airbnb Rental Income: $null

Traditional Rental Income: $4376

Airbnb ROI: N/A

Traditional ROI: 2.28%

802 Park Street

Ashland, OR

2 beds | 2 baths | 960 sq.ft.

$299,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.28%

Airbnb Rental Income: $null

Traditional Rental Income: $1960

Airbnb ROI: N/A

Traditional ROI: 3.28%

271 Cove Road

Ashland, OR

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

$1,590,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.56%

Airbnb Rental Income: $null

Traditional Rental Income: $5568

Airbnb ROI: N/A

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%

295 Tolman Creek Road #1

Ashland, OR

2 beds | 2 baths | 988 sq.ft.

$299,500

Airbnb cash on cash: N/A

Traditional cash on cash: 5.74%

Airbnb Rental Income: $null

Traditional Rental Income: $2541

Airbnb ROI: N/A