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: -2.46% Traditional cash on cash: 0.88% Airbnb Rental Income: $1335 Traditional Rental Income: $3103 Airbnb ROI: -2.46% Traditional ROI: 0.88%
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: -1.47% Traditional cash on cash: 1.12% Airbnb Rental Income: $1405 Traditional Rental Income: $4331 Airbnb ROI: -1.47% 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: 0.04% Traditional cash on cash: 2.17% Airbnb Rental Income: $2316 Traditional Rental Income: $3579 Airbnb ROI: 0.04% 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: -0.16% Traditional cash on cash: 3.29% Airbnb Rental Income: $1405 Traditional Rental Income: $2751 Airbnb ROI: -0.16% 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: -0.32% Traditional cash on cash: 2.28% Airbnb Rental Income: $2316 Traditional Rental Income: $4376 Airbnb ROI: -0.32% 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: -0.75% Traditional cash on cash: 3.01% Airbnb Rental Income: $1405 Traditional Rental Income: $3327 Airbnb ROI: -0.75% 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: 0.16% Traditional cash on cash: 2.27% Airbnb Rental Income: $2316 Traditional Rental Income: $3558 Airbnb ROI: 0.16% 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: -0.42% Traditional cash on cash: 3.28% Airbnb Rental Income: $1324 Traditional Rental Income: $1960 Airbnb ROI: -0.42% 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: -0.87% Traditional cash on cash: 1.8% Airbnb Rental Income: $1405 Traditional Rental Income: $4192 Airbnb ROI: -0.87% 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: -0.03% Traditional cash on cash: 2.56% Airbnb Rental Income: $2316 Traditional Rental Income: $5568 Airbnb ROI: -0.03% 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: -0.21% Traditional cash on cash: 7.45% Airbnb Rental Income: $2584 Traditional Rental Income: $8631 Airbnb ROI: -0.21% Traditional ROI: 7.45%
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: -0.43% Traditional cash on cash: 2.02% Airbnb Rental Income: $1405 Traditional Rental Income: $2354 Airbnb ROI: -0.43% Traditional ROI: 2.02%
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: 0.36% Traditional cash on cash: 6.22% Airbnb Rental Income: $1324 Traditional Rental Income: $2280 Airbnb ROI: 0.36% 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: -0.46% Traditional cash on cash: 2.36% Airbnb Rental Income: $2316 Traditional Rental Income: $5279 Airbnb ROI: -0.46% 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.	$595,000	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.53% Airbnb Rental Income: $1405 Traditional Rental Income: $3049 Airbnb ROI: -0.2% Traditional ROI: 3.53%
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: -0.43% Traditional cash on cash: 4.53% Airbnb Rental Income: $1405 Traditional Rental Income: $3811 Airbnb ROI: -0.43% Traditional ROI: 4.53%
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: 0.11% Traditional cash on cash: 1.96% Airbnb Rental Income: $1324 Traditional Rental Income: $1377 Airbnb ROI: 0.11% 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: -1.18% Traditional cash on cash: 0.15% Airbnb Rental Income: $2316 Traditional Rental Income: $6662 Airbnb ROI: -1.18% 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: -0.56% Traditional cash on cash: 5.71% Airbnb Rental Income: $1405 Traditional Rental Income: $3305 Airbnb ROI: -0.56% 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: -0.28% Traditional cash on cash: 2.85% Airbnb Rental Income: $1324 Traditional Rental Income: $2115 Airbnb ROI: -0.28% Traditional ROI: 2.85%
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: -1% Traditional cash on cash: 1.7% Airbnb Rental Income: $1405 Traditional Rental Income: $4132 Airbnb ROI: -1% Traditional ROI: 1.7%
347 Ravenwood Place Ashland, OR Nestled just blocks away from charming downtown Ashland, the Ravenwood Townhouses boast an...	2 beds \| 3 baths \| 1,400 sq.ft.	$433,500	Airbnb cash on cash: -0.84% Traditional cash on cash: 4.04% Airbnb Rental Income: $1324 Traditional Rental Income: $2895 Airbnb ROI: -0.84% Traditional ROI: 4.04%
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: -0.68% Traditional cash on cash: 0.99% Airbnb Rental Income: $2316 Traditional Rental Income: $3690 Airbnb ROI: -0.68% 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: -0.17% Traditional cash on cash: 1.84% Airbnb Rental Income: $2316 Traditional Rental Income: $4446 Airbnb ROI: -0.17% 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: -4.49% Traditional cash on cash: 3.63% Airbnb Rental Income: $1324 Traditional Rental Income: $3430 Airbnb ROI: -4.49% Traditional ROI: 3.63%
933 Bellview Avenue #1 Ashland, OR Build your Ashland dream home on a private serene lot with creek frontage! This contempora...	3 beds \| 2 baths \| 1,629 sq.ft.	$749,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 3.51% Airbnb Rental Income: $1405 Traditional Rental Income: $3591 Airbnb ROI: -0.23% Traditional ROI: 3.51%
933 Bellview Avenue #2 Ashland, OR Build your Ashland dream home on a private serene lot with creek frontage! This contempora...	2 beds \| 2 baths \| 1,405 sq.ft.	$669,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.67% Airbnb Rental Income: $1324 Traditional Rental Income: $3354 Airbnb ROI: -0.24% Traditional ROI: 3.67%
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: -0.94% Traditional cash on cash: 1.27% Airbnb Rental Income: $2316 Traditional Rental Income: $5288 Airbnb ROI: -0.94% 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: 1.29% Traditional cash on cash: 0.92% Airbnb Rental Income: $2316 Traditional Rental Income: $1546 Airbnb ROI: 1.29% Traditional ROI: 0.92%
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: 1.64% Traditional cash on cash: 7.52% Airbnb Rental Income: $1324 Traditional Rental Income: $2375 Airbnb ROI: 1.64% Traditional ROI: 7.52%
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: 0.37% Traditional cash on cash: 5.91% Airbnb Rental Income: $1324 Traditional Rental Income: $2196 Airbnb ROI: 0.37% Traditional ROI: 5.91%
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: -1.09% Traditional cash on cash: 1.4% Airbnb Rental Income: $1405 Traditional Rental Income: $7439 Airbnb ROI: -1.09% 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: 0.93% Traditional cash on cash: 3.49% Airbnb Rental Income: $2316 Traditional Rental Income: $3350 Airbnb ROI: 0.93% 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: -9.11% Traditional cash on cash: -0.54% Airbnb Rental Income: $1335 Traditional Rental Income: $2154 Airbnb ROI: -9.11% Traditional ROI: -0.54%
339 Ravenwood Place Ashland, OR True Craftsman's Renovation in this Ravenwood Townhome, just steps to renowned Downtown As...	3 beds \| 3 baths \| 1,392 sq.ft.	$420,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 4.34% Airbnb Rental Income: $1405 Traditional Rental Income: $2969 Airbnb ROI: -0.71% Traditional ROI: 4.34%
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: -0.34% Traditional cash on cash: 3.38% Airbnb Rental Income: $1335 Traditional Rental Income: $2148 Airbnb ROI: -0.34% Traditional ROI: 3.38%
700 Neil Creek Road Ashland, OR Stunning mountain and lake views from this log home with detached artist studio just 10 mi...	3 beds \| 2 baths \| 1,759 sq.ft.	$499,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.64% Airbnb Rental Income: $1405 Traditional Rental Income: $2820 Airbnb ROI: -0.29% Traditional ROI: 3.64%
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: -0.75% Traditional cash on cash: 0.26% Airbnb Rental Income: $1405 Traditional Rental Income: $2461 Airbnb ROI: -0.75% 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: -0.27% Traditional cash on cash: 0.64% Airbnb Rental Income: $1335 Traditional Rental Income: $1668 Airbnb ROI: -0.27% Traditional ROI: 0.64%
1694 Old Siskiyou Highway Ashland, OR Just a short drive south of Ashland, Oregon, lies this private 22-acre retreat. This priva...	4 beds \| 4 baths \| 3,206 sq.ft.	$1,299,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 2.37% Airbnb Rental Income: $2316 Traditional Rental Income: $5075 Airbnb ROI: -0.39% Traditional ROI: 2.37%

Real Estate investment in Ashland, OR

There are 102 properties for sale in the city of Ashland . The median list price in Ashland is $659,000 and the average price per square foot is $304. In December 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,212.

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

There are 102 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 $1,405.

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: -2.46%

Traditional cash on cash: 0.88%

Airbnb Rental Income: $1335

Traditional Rental Income: $3103

Airbnb ROI: -2.46%

Traditional ROI: 0.88%

545 Ashland Creek Drive

Ashland, OR

3 beds | 3 baths | 3,108 sq.ft.

$1,395,808

Airbnb cash on cash: -1.47%

Traditional cash on cash: 1.12%

Airbnb Rental Income: $1405

Traditional Rental Income: $4331

Airbnb ROI: -1.47%

Traditional ROI: 1.12%

774 Lisa Lane

Ashland, OR

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

$929,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 2.17%

Airbnb Rental Income: $2316

Traditional Rental Income: $3579

Airbnb ROI: 0.04%

Traditional ROI: 2.17%

740 Park Street

Ashland, OR

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

$549,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $1405

Traditional Rental Income: $2751

Airbnb ROI: -0.16%

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: -0.32%

Traditional cash on cash: 2.28%

Airbnb Rental Income: $2316

Traditional Rental Income: $4376

Airbnb ROI: -0.32%

Traditional ROI: 2.28%

932 Morton Street

Ashland, OR

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

$668,000

Airbnb cash on cash: -0.75%

Traditional cash on cash: 3.01%

Airbnb Rental Income: $1405

Traditional Rental Income: $3327

Airbnb ROI: -0.75%

Traditional ROI: 3.01%

288 Maywood Way

Ashland, OR

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

$925,000

Airbnb cash on cash: 0.16%

Traditional cash on cash: 2.27%

Airbnb Rental Income: $2316

Traditional Rental Income: $3558

Airbnb ROI: 0.16%

Traditional ROI: 2.27%

802 Park Street

Ashland, OR

2 beds | 2 baths | 960 sq.ft.

$299,900

Airbnb cash on cash: -0.42%

Traditional cash on cash: 3.28%

Airbnb Rental Income: $1324

Traditional Rental Income: $1960

Airbnb ROI: -0.42%