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
175 Lithia Way #200 Ashland, OR Stylish corner-unit condominium on the second level of Plaza West at First Place in the he...	1 beds \| 2 baths \| 1,448 sq.ft.	$700,000	Airbnb cash on cash: -2.21% Traditional cash on cash: 0.88% Airbnb Rental Income: $1529 Traditional Rental Income: $3103 Airbnb ROI: -2.21% Traditional ROI: 0.88%
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.	$949,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 2.12% Airbnb Rental Income: $2995 Traditional Rental Income: $3579 Airbnb ROI: 0.68% Traditional ROI: 2.12%
969 Camelot Drive Ashland, OR Turn-key end unit townhome with exceptional sunsets, valley, and mountain views within a f...	3 beds \| 3 baths \| 1,808 sq.ft.	$525,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.6% Airbnb Rental Income: $1474 Traditional Rental Income: $2474 Airbnb ROI: -0.33% Traditional ROI: 2.6%
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.	$579,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.09% Airbnb Rental Income: $1474 Traditional Rental Income: $2751 Airbnb ROI: -0.08% Traditional ROI: 3.09%
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.	$1,095,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 2.28% Airbnb Rental Income: $2995 Traditional Rental Income: $4376 Airbnb ROI: 0.25% 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: -0.66% Traditional cash on cash: 3.01% Airbnb Rental Income: $1474 Traditional Rental Income: $3327 Airbnb ROI: -0.66% Traditional ROI: 3.01%
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.	$305,000	Airbnb cash on cash: 0% Traditional cash on cash: 3.21% Airbnb Rental Income: $1472 Traditional Rental Income: $1960 Airbnb ROI: 0% Traditional ROI: 3.21%
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.	$1,395,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.6% Airbnb Rental Income: $1474 Traditional Rental Income: $4192 Airbnb ROI: -0.83% Traditional ROI: 1.6%
2245 Colestin Road Ashland, OR Privacy in Southwest Oregon close to Ashland shopping, restaurants and Shakesphere. Prist...	4 beds \| 3 baths \| 1,872 sq.ft.	$789,808	Airbnb cash on cash: 1.68% Traditional cash on cash: 3.53% Airbnb Rental Income: $2995 Traditional Rental Income: $3672 Airbnb ROI: 1.68% Traditional ROI: 3.53%
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: 0.35% Traditional cash on cash: 2.56% Airbnb Rental Income: $2995 Traditional Rental Income: $5568 Airbnb ROI: 0.35% 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: 0.66% Traditional cash on cash: 7.45% Airbnb Rental Income: $3493 Traditional Rental Income: $8631 Airbnb ROI: 0.66% 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: 0.89% Traditional cash on cash: 6.22% Airbnb Rental Income: $1472 Traditional Rental Income: $2280 Airbnb ROI: 0.89% Traditional ROI: 6.22%
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: -0.01% Traditional cash on cash: 2.36% Airbnb Rental Income: $2995 Traditional Rental Income: $5279 Airbnb ROI: -0.01% Traditional ROI: 2.36%
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.	$307,500	Airbnb cash on cash: 0.38% Traditional cash on cash: 5.57% Airbnb Rental Income: $1472 Traditional Rental Income: $2541 Airbnb ROI: 0.38% Traditional ROI: 5.57%
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: -0.33% Traditional cash on cash: 4.53% Airbnb Rental Income: $1474 Traditional Rental Income: $3811 Airbnb ROI: -0.33% Traditional ROI: 4.53%
303 Palm Avenue Ashland, OR Built in 1929, this timeless Ashland cottage blends historic character with modern comfort...	3 beds \| 1 baths \| 1,270 sq.ft.	$550,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 3.02% Airbnb Rental Income: $1474 Traditional Rental Income: $2551 Airbnb ROI: 0.08% Traditional ROI: 3.02%
854 Twin Pines Circle #7 Ashland, OR BEAUTIFUL LIGHT AND BRIGHT END UNIT! Don't miss this opportunity! This 2-bedroom, 1-bath c...	2 beds \| 1 baths \| 896 sq.ft.	$265,000	Airbnb cash on cash: 0.61% Traditional cash on cash: 1.96% Airbnb Rental Income: $1472 Traditional Rental Income: $1377 Airbnb ROI: 0.61% Traditional ROI: 1.96%
4896 Highway 66 Ashland, OR 5 private estate-quality acres, masterfully landscaped with expansive emerald, green lawn ...	4 beds \| 3 baths \| 2,790 sq.ft.	$1,499,000	Airbnb cash on cash: -0.19% Traditional cash on cash: 1.17% Airbnb Rental Income: $2995 Traditional Rental Income: $4200 Airbnb ROI: -0.19% Traditional ROI: 1.17%
9412 MT ASHLAND SKI RD Ashland, OR A stunning Chalet style home sitting high atop a ridge looking west over the Siskiyou moun...	3 beds \| 2 baths \| 2,376 sq.ft.	$875,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 2.31% Airbnb Rental Income: $1474 Traditional Rental Income: $3431 Airbnb ROI: -0.63% Traditional ROI: 2.31%
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: -1.02% Traditional cash on cash: 0.15% Airbnb Rental Income: $2995 Traditional Rental Income: $6662 Airbnb ROI: -1.02% 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: -0.41% Traditional cash on cash: 5.71% Airbnb Rental Income: $1474 Traditional Rental Income: $3305 Airbnb ROI: -0.41% 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: 0.04% Traditional cash on cash: 2.84% Airbnb Rental Income: $1472 Traditional Rental Income: $2115 Airbnb ROI: 0.04% Traditional ROI: 2.84%
2275 Dollarhide Way Ashland, OR Beautifully maintained townhome with tranquil outdoor entertainment area, conveniently loc...	2 beds \| 3 baths \| 1,599 sq.ft.	$429,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.79% Airbnb Rental Income: $1472 Traditional Rental Income: $2531 Airbnb ROI: 0.07% Traditional ROI: 3.79%
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: -0.2% Traditional cash on cash: 0.99% Airbnb Rental Income: $2995 Traditional Rental Income: $3690 Airbnb ROI: -0.2% Traditional ROI: 0.99%
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	$845,000	Airbnb cash on cash: 1.42% Traditional cash on cash: 0.42% Airbnb Rental Income: $2995 Traditional Rental Income: $1518 Airbnb ROI: 1.42% Traditional ROI: 0.42%
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.	$3,900,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 0.31% Airbnb Rental Income: $2995 Traditional Rental Income: $6711 Airbnb ROI: -0.91% Traditional ROI: 0.31%
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: 0.25% Traditional cash on cash: 1.84% Airbnb Rental Income: $2995 Traditional Rental Income: $4446 Airbnb ROI: 0.25% Traditional ROI: 1.84%
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.	$1,200,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.89% Airbnb Rental Income: $1474 Traditional Rental Income: $3671 Airbnb ROI: -0.47% Traditional ROI: 1.89%
988 Dead Indian Memorial Road Ashland, OR Rare Ashland opportunity on a 5+ acre tax lot, close proximity to town and Belle Fiore Win...	4 beds \| 3 baths \| 4,668 sq.ft.	$1,475,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.87% Airbnb Rental Income: $2995 Traditional Rental Income: $3556 Airbnb ROI: -0.05% Traditional ROI: 0.87%
1475 Dead Indian Memorial Road Ashland, OR Experience the pinnacle of country living on nearly 25 private, gated acres just minutes f...	4 beds \| 4 baths \| 4,382 sq.ft.	$1,695,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 0.81% Airbnb Rental Income: $2995 Traditional Rental Income: $4142 Airbnb ROI: -0.36% Traditional ROI: 0.81%
19015 Dead Indian Memorial Road Ashland, OR Lovely home on beautiful Oregon Horse Property! 30+ acres surrounded by BLM and US Forestr...	3 beds \| 2 baths \| 2,624 sq.ft.	$975,000	Airbnb cash on cash: -0.15% Traditional cash on cash: 3.26% Airbnb Rental Income: $1474 Traditional Rental Income: $4130 Airbnb ROI: -0.15% Traditional ROI: 3.26%
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: -4.09% Traditional cash on cash: 3.63% Airbnb Rental Income: $1472 Traditional Rental Income: $3430 Airbnb ROI: -4.09% 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: -0.59% Traditional cash on cash: 1.27% Airbnb Rental Income: $2995 Traditional Rental Income: $5288 Airbnb ROI: -0.59% 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	$575,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 0.9% Airbnb Rental Income: $1472 Traditional Rental Income: $1546 Airbnb ROI: -0.05% Traditional ROI: 0.9%
2023 Siskiyou Boulevard Ashland, OR Exquisitely maintained townhome style residence in tranquil complex! Excellently designed ...	2 beds \| 2 baths \| 896 sq.ft.	$263,554	Airbnb cash on cash: 2.14% Traditional cash on cash: 7.52% Airbnb Rental Income: $1472 Traditional Rental Income: $2375 Airbnb ROI: 2.14% Traditional ROI: 7.52%
405 Wrights Creek Drive Ashland, OR Welcome to your private woodland retreat in the Ashland hills! This charming 3-bedroom, 2-...	3 beds \| 2 baths \| 1,364 sq.ft.	$450,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.68% Airbnb Rental Income: $1474 Traditional Rental Income: $2526 Airbnb ROI: 0.15% Traditional ROI: 3.68%
237 B Street Ashland, OR A rare opportunity located in Ashland's beloved Railroad District! This charming & versati...	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 1.33% Airbnb Rental Income: $1474 Traditional Rental Income: $1839 Airbnb ROI: 0.02% Traditional ROI: 1.33%
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: 0.9% Traditional cash on cash: 5.91% Airbnb Rental Income: $1472 Traditional Rental Income: $2196 Airbnb ROI: 0.9% Traditional ROI: 5.91%
1320 N Mountain Avenue Ashland, OR Dana Campbell Vineyards is a legacy wine business offering multiple avenues for growth wit...	3 beds \| 6 baths \| 3,564 sq.ft.	$2,800,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 1.4% Airbnb Rental Income: $1474 Traditional Rental Income: $7439 Airbnb ROI: -1.07% 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: -7.99% Traditional cash on cash: -0.54% Airbnb Rental Income: $1529 Traditional Rental Income: $2154 Airbnb ROI: -7.99% Traditional ROI: -0.54%

Real Estate investment in Ashland, OR

There are 152 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 $283. In October 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,291.

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

There are 152 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 $1,474.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

175 Lithia Way #200

Ashland, OR

1 beds | 2 baths | 1,448 sq.ft.

$700,000

Airbnb cash on cash: -2.21%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $1529

Traditional Rental Income: $3103

Airbnb ROI: -2.21%

Traditional ROI: 0.88%

774 Lisa Lane

Ashland, OR

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

$949,000

Airbnb cash on cash: 0.68%

Traditional cash on cash: 2.12%

Airbnb Rental Income: $2995

Traditional Rental Income: $3579

Airbnb ROI: 0.68%

Traditional ROI: 2.12%

969 Camelot Drive

Ashland, OR

3 beds | 3 baths | 1,808 sq.ft.

$525,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 2.6%

Airbnb Rental Income: $1474

Traditional Rental Income: $2474

Airbnb ROI: -0.33%

Traditional ROI: 2.6%

740 Park Street

Ashland, OR

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

$579,000

Airbnb cash on cash: -0.08%

Traditional cash on cash: 3.09%

Airbnb Rental Income: $1474

Traditional Rental Income: $2751

Airbnb ROI: -0.08%

Traditional ROI: 3.09%

1369 Tolman Creek Road

Ashland, OR

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

$1,095,000

Airbnb cash on cash: 0.25%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2995

Traditional Rental Income: $4376

Airbnb ROI: 0.25%

Traditional ROI: 2.28%

932 Morton Street

Ashland, OR

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

$668,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $1474

Traditional Rental Income: $3327

Airbnb ROI: -0.66%

Traditional ROI: 3.01%

802 Park Street

Ashland, OR

2 beds | 2 baths | 960 sq.ft.

$305,000

Airbnb cash on cash: 0%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $1472

Traditional Rental Income: $1960

Airbnb ROI: 0%

Traditional ROI: 3.21%

753 Wrights Creek Drive

Ashland, OR

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

$1,395,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 1.6%

Airbnb Rental Income: $1474

Traditional Rental Income: $4192

Airbnb ROI: -0.83%