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%
932 Morton Street Ashland, OR Peace, Beauty Rogue Valley Views Trailheads. In Town. Fall in love with this Upper Diamo...	3 beds \| 2 baths \| 2,332 sq.ft.	$668,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.01% Airbnb Rental Income: $null Traditional Rental Income: $3327 Airbnb ROI: N/A Traditional ROI: 3.01%
288 Maywood Way Ashland, OR Stunning single-level contemporary home on 6.81 irrigated acres just minutes from downtown...	4 beds \| 2 baths \| 2,070 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.27% Airbnb Rental Income: $null Traditional Rental Income: $3558 Airbnb ROI: N/A Traditional ROI: 2.27%
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%
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 remodeled Victorian blends historic charm withmodern luxury in the heart of Ash...	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%
495 Chestnut Street #6 Ashland, OR Located just minutes from downtown Ashland and Southern Oregon University, this heartwarmi...	2 beds \| 2 baths \| 832 sq.ft.	$246,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.75% Airbnb Rental Income: $null Traditional Rental Income: $2280 Airbnb ROI: N/A Traditional ROI: 5.75%
767 Oak Street Ashland, OR This charming and modernized Victorian has it all! Very close to Ashland's downtown, the h...	4 beds \| 5 baths \| 3,590 sq.ft.	$1,350,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.36% Airbnb Rental Income: $null Traditional Rental Income: $5279 Airbnb ROI: N/A Traditional ROI: 2.36%
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%
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%
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%
166 Mountain View Drive Ashland, OR Part of Ashland Garden Cottages and beautifully designed for sustainable living, distincti...	2 beds \| 1 baths \| 768 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $2115 Airbnb ROI: N/A Traditional ROI: 2.85%
1999 Tolman Creek Road Ashland, OR Custom-built in 1986, this meticulously maintained home blends superior craftsmanship with...	4 beds \| 4 baths \| 4,189 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.99% Airbnb Rental Income: $null Traditional Rental Income: $3690 Airbnb ROI: N/A Traditional ROI: 0.99%
451 E Ashland Lane Ashland, OR Your Dream Country Escape Awaits!Have you ever dreamed of country living? Your very own ''...	4 beds \| 4 baths \| 4,071 sq.ft.	$1,449,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.84% Airbnb Rental Income: $null Traditional Rental Income: $4446 Airbnb ROI: N/A Traditional ROI: 1.84%
597 Mariposa Court Ashland, OR Lovely single-level condo in Ashland's premier 55+ Mountain Meadows community. This beauti...	2 beds \| 2 baths \| 1,513 sq.ft.	$329,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.63% Airbnb Rental Income: $null Traditional Rental Income: $3430 Airbnb ROI: N/A Traditional ROI: 3.63%
3721 Old Hwy 99 Ashland, OR Currently operated as a successful Airbnb, this 80-acre villa overlooks the valley and Emi...	4 beds \| 6 baths \| 4,793 sq.ft.	$1,724,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.27% Airbnb Rental Income: $null Traditional Rental Income: $5288 Airbnb ROI: N/A Traditional ROI: 1.27%
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%
495 Chestnut Street #19 Ashland, OR Charming Ashland Condo in Prime Location! Conveniently situated near restaurants, shopping...	2 beds \| 2 baths \| 832 sq.ft.	$245,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.43% Airbnb Rental Income: $null Traditional Rental Income: $2196 Airbnb ROI: N/A Traditional ROI: 5.43%
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%
802 Beach Street Ashland, OR Beautifully remodeled and furnished, this Ashland retreat offers modern comfort. Thoughtfu...	4 beds \| 2 baths \| 1,616 sq.ft.	$675,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.49% Airbnb Rental Income: $null Traditional Rental Income: $3350 Airbnb ROI: N/A Traditional ROI: 3.49%
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%
967 Golden Aspen Place Ashland, OR Staged and ready for you to call home. Sweet one bedroom unit with office and extra room o...	1 beds \| 2 baths \| 1,186 sq.ft.	$249,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $2485 Airbnb ROI: N/A Traditional ROI: 3.24%
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%
500 Allison Street Ashland, OR This updated duplex offers an ideal blend of comfort, convenience, and potential. Centrall...	N/A beds \| N/A baths \| N/A	$530,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.84% Airbnb Rental Income: $null Traditional Rental Income: $1729 Airbnb ROI: N/A Traditional ROI: 1.84%
3060 Ashland Mine Road Ashland, OR Luxury meets efficiency & privacy in this 2025 custom home, designed to capture truly stun...	3 beds \| 2 baths \| 1,996 sq.ft.	$998,500	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3687 Airbnb ROI: N/A Traditional ROI: 2.59%
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%
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%
242 Grant Street Ashland, OR Ground-level condominium in a well-maintained development near parks, downtown entertainme...	2 beds \| 1 baths \| 1,174 sq.ft.	$300,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.11% Airbnb Rental Income: $null Traditional Rental Income: $2447 Airbnb ROI: N/A Traditional ROI: 5.11%
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.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.59% Airbnb Rental Income: $null Traditional Rental Income: $4318 Airbnb ROI: N/A Traditional ROI: 4.59%
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%
681 Liberty Street Ashland, OR Beautiful mountain views from this hillside home. This charming 1947 home offers classic ...	3 beds \| 2 baths \| 2,139 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $3378 Airbnb ROI: N/A Traditional ROI: 4.87%
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%

Real Estate investment in Ashland, OR

There are 103 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 $295. In December 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,245.

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

There are 103 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 $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%

932 Morton Street

Ashland, OR

3 beds | 2 baths | 2,332 sq.ft.

$668,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.01%

Airbnb Rental Income: $null

Traditional Rental Income: $3327

Airbnb ROI: N/A

Traditional ROI: 3.01%

288 Maywood Way

Ashland, OR

4 beds | 2 baths | 2,070 sq.ft.

$925,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.27%

Airbnb Rental Income: $null

Traditional Rental Income: $3558

Airbnb ROI: N/A

Traditional ROI: 2.27%

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%

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