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.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $2751 Airbnb ROI: N/A Traditional ROI: 3.29%
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%
753 Wrights Creek Drive Ashland, OR Gorgeous, architecturally designed contemporary home nestled in the hills of Ashland, Oreg...	3 beds \| 3 baths \| 3,011 sq.ft.	$1,295,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.8% Airbnb Rental Income: $null Traditional Rental Income: $4192 Airbnb ROI: N/A Traditional ROI: 1.8%
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%
490 Conifer Way Ashland, OR This SINGLE LEVEL 1,864 sq. ft. home offers everything you need plus Breathtaking Mountain...	3 beds \| 2 baths \| 1,864 sq.ft.	$585,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $3049 Airbnb ROI: N/A Traditional ROI: 3.6%
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%
694 Timberlake Drive Ashland, OR Enjoy the peace and privacy of a rural retreat with the conveniences of close proximity to...	3 beds \| 3 baths \| 2,184 sq.ft.	$610,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $3811 Airbnb ROI: N/A Traditional ROI: 4.53%
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%
99 Granite Street Ashland, OR Exceptionally refined Craftsman home with unparalleled amenities - just steps from Lithia ...	4 beds \| 9 baths \| 6,903 sq.ft.	$4,000,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.15% Airbnb Rental Income: $null Traditional Rental Income: $6662 Airbnb ROI: N/A Traditional ROI: 0.15%
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%
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	$569,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $1546 Airbnb ROI: N/A Traditional ROI: 0.92%
1320 N Mountain Avenue Ashland, OR New lease-option and seller-carried financing terms available! Dana Campbell Vineyards is ...	3 beds \| 6 baths \| 3,564 sq.ft.	$2,800,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.4% Airbnb Rental Income: $null Traditional Rental Income: $7439 Airbnb ROI: N/A Traditional ROI: 1.4%
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: -0.54% Airbnb Rental Income: $null Traditional Rental Income: $2154 Airbnb ROI: N/A Traditional ROI: -0.54%
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: 2.38% Airbnb Rental Income: $null Traditional Rental Income: $3471 Airbnb ROI: N/A Traditional ROI: 2.38%
411 N Mountain Avenue Ashland, OR Nestled in the picturesque town of Ashland, this exceptional two-story townhouse offers a ...	3 beds \| 3 baths \| 1,479 sq.ft.	$350,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2729 Airbnb ROI: N/A Traditional ROI: 4.37%
750 Park Street Ashland, OR Welcome to your private retreat in the heart of Ashland! This spacious 4-bedroom, 3-bathro...	4 beds \| 3 baths \| 2,558 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.66% Airbnb Rental Income: $null Traditional Rental Income: $4318 Airbnb ROI: N/A Traditional ROI: 4.66%
700 Clay Street Ashland, OR Thoroughly updated view home with private park-like organic gardens near The Siskiyou Scho...	4 beds \| 3 baths \| 2,186 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.77% Airbnb Rental Income: $null Traditional Rental Income: $3826 Airbnb ROI: N/A Traditional ROI: 3.77%
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%
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%
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.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.25% Airbnb Rental Income: $null Traditional Rental Income: $3182 Airbnb ROI: N/A Traditional ROI: 4.25%
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 Nicely updated historic home located within three blocks of Ashland's downtown plaza and L...	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.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.44% Airbnb Rental Income: $null Traditional Rental Income: $4314 Airbnb ROI: N/A Traditional ROI: 1.44%
311 Glenn Street Ashland, OR Excellent proximity to The Plaza and downtown from this move-in-ready condo! Recent update...	2 beds \| 2 baths \| 952 sq.ft.	$235,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.43% Airbnb Rental Income: $null Traditional Rental Income: $2445 Airbnb ROI: N/A Traditional ROI: 7.43%
355 Granite Street Ashland, OR This storybook home blends timeless charm w/thoughtful updates in a private setting across...	3 beds \| 2 baths \| 2,015 sq.ft.	$859,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.04% Airbnb Rental Income: $null Traditional Rental Income: $3277 Airbnb ROI: N/A Traditional ROI: 2.04%
330 High Street #1-4 Ashland, OR Excellent investment opportunity near downtown Ashland! This fully rented 4-plex is nestle...	N/A beds \| N/A baths \| 4,032 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.4% Airbnb Rental Income: $null Traditional Rental Income: $1669 Airbnb ROI: N/A Traditional ROI: 0.4%
3721 SISKIYOU Hwy Ashland, OR Operated as a successful Airbnb, this 80-acre villa overlooks the valley & Emigrant Lake w...	4 beds \| 5 baths \| 4,793 sq.ft.	$1,724,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.94% Airbnb Rental Income: $null Traditional Rental Income: $7955 Airbnb ROI: N/A Traditional ROI: 2.94%
269 Idaho Street Ashland, OR Well maintained home with a desirable location, just blocks from beautiful downtown Ashlan...	3 beds \| 2 baths \| 1,667 sq.ft.	$649,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3119 Airbnb ROI: N/A Traditional ROI: 3.26%
224 Alicia Street Ashland, OR Welcome to an exceptional opportunity in Ashland, where comfort and flexible living come t...	5 beds \| 5 baths \| 3,207 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.4% Airbnb Rental Income: $null Traditional Rental Income: $6688 Airbnb ROI: N/A Traditional ROI: 4.4%
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%

Real Estate investment in Ashland, OR

There are 72 properties for sale in the city of Ashland . The median list price in Ashland is $672,000 and the average price per square foot is $313. In January 2026, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $2,816.

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

There are 72 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.

$549,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.29%

Airbnb Rental Income: $null

Traditional Rental Income: $2751

Airbnb ROI: N/A

Traditional ROI: 3.29%

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%

753 Wrights Creek Drive

Ashland, OR

3 beds | 3 baths | 3,011 sq.ft.

$1,295,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.8%

Airbnb Rental Income: $null

Traditional Rental Income: $4192

Airbnb ROI: N/A

Traditional ROI: 1.8%

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%

490 Conifer Way

Ashland, OR

3 beds | 2 baths | 1,864 sq.ft.

$585,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.6%

Airbnb Rental Income: $null

Traditional Rental Income: $3049

Airbnb ROI: N/A