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
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: -0.4% Traditional cash on cash: 2.31% Airbnb Rental Income: $1692 Traditional Rental Income: $3431 Airbnb ROI: -0.4% Traditional ROI: 2.31%
2809 DEAD INDIAN MEMORIAL RD Ashland, OR Experience refined country living on just over 23 acres of rolling green hills, and panora...	3 beds \| 3 baths \| 2,530 sq.ft.	$880,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.38% Airbnb Rental Income: $1692 Traditional Rental Income: $3471 Airbnb ROI: -0.36% Traditional ROI: 2.38%
3729 OLD HIGHWAY 99 Ashland, OR Stunning luxury estate with 3BD/3.5BA on 32.44 acres with breathtaking views of Emigrant L...	3 beds \| 4 baths \| 7,426 sq.ft.	$875,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 4.79% Airbnb Rental Income: $1692 Traditional Rental Income: $5874 Airbnb ROI: -0.92% Traditional ROI: 4.79%
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: 0.21% Traditional cash on cash: 0.42% Airbnb Rental Income: $1853 Traditional Rental Income: $1518 Airbnb ROI: 0.21% 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: -1.18% Traditional cash on cash: 0.31% Airbnb Rental Income: $1853 Traditional Rental Income: $6711 Airbnb ROI: -1.18% Traditional ROI: 0.31%
30-36 Dewey Street Ashland, OR Don't miss out on owning an amazing investment property in Ashland, Oregon. This 6-unit pr...	N/A beds \| N/A baths \| N/A	$849,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 0.3% Airbnb Rental Income: $1692 Traditional Rental Income: $1440 Airbnb ROI: 0.03% Traditional ROI: 0.3%
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: -0.46% Traditional cash on cash: 1.84% Airbnb Rental Income: $1853 Traditional Rental Income: $4446 Airbnb ROI: -0.46% Traditional ROI: 1.84%
970 Elkader Street Ashland, OR Enchanting custom home on rare private acreage within city limits - centrally located abov...	3 beds \| 2 baths \| 2,096 sq.ft.	$750,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 3.25% Airbnb Rental Income: $1692 Traditional Rental Income: $3722 Airbnb ROI: -0.33% Traditional ROI: 3.25%
597 Mariposa Court Ashland, OR Lovely Single-Level Mountain Meadows Condominium Home. Nestled in the heart of Ashland's r...	2 beds \| 2 baths \| 1,513 sq.ft.	$354,500	Airbnb cash on cash: -3.49% Traditional cash on cash: 3.31% Airbnb Rental Income: $1626 Traditional Rental Income: $3430 Airbnb ROI: -3.49% Traditional ROI: 3.31%
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	$585,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 0.87% Airbnb Rental Income: $1626 Traditional Rental Income: $1546 Airbnb ROI: 0.17% Traditional ROI: 0.87%
1035 N Main Street Ashland, OR Nestled above the boulevard, minutes from downtown, this historic 1920's cottage exudes ti...	3 beds \| 3 baths \| 1,442 sq.ft.	$450,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 5.65% Airbnb Rental Income: $1692 Traditional Rental Income: $3234 Airbnb ROI: 0.87% Traditional ROI: 5.65%
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.	$499,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.22% Airbnb Rental Income: $1692 Traditional Rental Income: $2526 Airbnb ROI: 0.43% Traditional ROI: 3.22%
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: 0.38% Traditional cash on cash: 3.53% Airbnb Rental Income: $1853 Traditional Rental Income: $3672 Airbnb ROI: 0.38% Traditional ROI: 3.53%
1288 Calypso Court Ashland, OR GARDENER'S DELIGHT, CORNER VIEW, EXCEPTIONAL UPGRADES Beautifully upgraded co-housing in t...	1 beds \| 2 baths \| 646 sq.ft.	$319,900	Airbnb cash on cash: 1.33% Traditional cash on cash: 4.58% Airbnb Rental Income: $1721 Traditional Rental Income: $2224 Airbnb ROI: 1.33% Traditional ROI: 4.58%
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: 1.46% Traditional cash on cash: 5.91% Airbnb Rental Income: $1626 Traditional Rental Income: $2196 Airbnb ROI: 1.46% 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% Traditional cash on cash: 1.4% Airbnb Rental Income: $1692 Traditional Rental Income: $7439 Airbnb ROI: -1% Traditional ROI: 1.4%
913 Bellview Avenue Ashland, OR Charming Ashland townhome with easy access to shopping, schools, I-5 and bus lines. This 2...	3 beds \| 3 baths \| 1,628 sq.ft.	$399,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 6.21% Airbnb Rental Income: $1692 Traditional Rental Income: $3319 Airbnb ROI: 0.62% Traditional ROI: 6.21%
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: -0.37% Traditional cash on cash: 3.01% Airbnb Rental Income: $1692 Traditional Rental Income: $3327 Airbnb ROI: -0.37% Traditional ROI: 3.01%
805 Oak Knoll Drive Ashland, OR Nestled in a prime Ashland location, this charming home is just minutes from the Oregon Sh...	3 beds \| 2 baths \| 1,709 sq.ft.	$485,000	Airbnb cash on cash: 0.49% Traditional cash on cash: 4.97% Airbnb Rental Income: $1692 Traditional Rental Income: $3252 Airbnb ROI: 0.49% Traditional ROI: 4.97%
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: 0.37% Traditional cash on cash: 2.84% Airbnb Rental Income: $1626 Traditional Rental Income: $2115 Airbnb ROI: 0.37% Traditional ROI: 2.84%
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.	$425,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 4.34% Airbnb Rental Income: $1692 Traditional Rental Income: $2969 Airbnb ROI: -0.05% Traditional ROI: 4.34%
1525 Baldy Creek Road Ashland, OR Secluded Ashland Retreat with Breathtaking Views. Escape to 80.8 acres of pristine natural...	1 beds \| 2 baths \| 1,246 sq.ft.	$595,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.57% Airbnb Rental Income: $1721 Traditional Rental Income: $2329 Airbnb ROI: 0.62% Traditional ROI: 2.57%
574 E Main Street Ashland, OR This property is ideally located in a prime commercial district, just a few blocks from As...	N/A beds \| N/A baths \| N/A	$1,050,500	Airbnb cash on cash: -0.22% Traditional cash on cash: 0.31% Airbnb Rental Income: $1853 Traditional Rental Income: $1873 Airbnb ROI: -0.22% Traditional ROI: 0.31%
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: -0.74% Traditional cash on cash: 0.87% Airbnb Rental Income: $1853 Traditional Rental Income: $3556 Airbnb ROI: -0.74% Traditional ROI: 0.87%
967 Golden Aspen Place Ashland, OR You wont want to miss this ''ready to move in'' turn key 55+ community Condo in a very des...	1 beds \| 2 baths \| 1,186 sq.ft.	$288,700	Airbnb cash on cash: -1.98% Traditional cash on cash: 2.57% Airbnb Rental Income: $1721 Traditional Rental Income: $2485 Airbnb ROI: -1.98% Traditional ROI: 2.57%
2299 Siskiyou Boulevard Ashland, OR Charming and conveniently located home just steps from Creekside Cottages community acreag...	1 beds \| 1 baths \| 882 sq.ft.	$365,000	Airbnb cash on cash: 0.57% Traditional cash on cash: 3.2% Airbnb Rental Income: $1721 Traditional Rental Income: $2148 Airbnb ROI: 0.57% Traditional ROI: 3.2%
343 Dead Indian Memorial Road Ashland, OR Rare Ashland Multifamily opportunity w/ TWO homes on two separate 5+ acre tax lots, near t...	4 beds \| 3 baths \| 5,800 sq.ft.	$1,850,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 0.67% Airbnb Rental Income: $1853 Traditional Rental Income: $4288 Airbnb ROI: -1.04% Traditional ROI: 0.67%
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: 0.15% Traditional cash on cash: 3.57% Airbnb Rental Income: $1692 Traditional Rental Income: $2820 Airbnb ROI: 0.15% Traditional ROI: 3.57%
1620 Butler Creek Road Ashland, OR East Ashland hills dream! This 3-bed, 2-bath home set on 6.52 acres of irrigated land is a...	3 beds \| 2 baths \| 1,298 sq.ft.	$595,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 2.34% Airbnb Rental Income: $1692 Traditional Rental Income: $2461 Airbnb ROI: 0.11% Traditional ROI: 2.34%
130 Westwood Street Ashland, OR Quality custom-built home on a large lot within the west hills of beautiful Ashland, Orego...	3 beds \| 3 baths \| 2,811 sq.ft.	$849,000	Airbnb cash on cash: -0.42% Traditional cash on cash: 3.37% Airbnb Rental Income: $1692 Traditional Rental Income: $4221 Airbnb ROI: -0.42% Traditional ROI: 3.37%
525 Ashland Loop Ashland, OR Searching for the Ultimate Oregon Dream Home & Location? This is it! Meander to the top of...	4 beds \| 3 baths \| 2,964 sq.ft.	$860,000	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.55% Airbnb Rental Income: $1853 Traditional Rental Income: $4623 Airbnb ROI: -0.53% Traditional ROI: 3.55%
586 B Street Ashland, OR 1910 Craftsman Style home in the Railroad District of Ashland, Oregon. This incredible pro...	4 beds \| 6 baths \| 4,584 sq.ft.	$1,975,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 2.64% Airbnb Rental Income: $1853 Traditional Rental Income: $8636 Airbnb ROI: -1.33% Traditional ROI: 2.64%
346 Stoneridge Avenue Ashland, OR Wonderful 4 bedroom, 2.5 bath home in the highly desirable Kestrel Park neighborhood. This...	4 beds \| 3 baths \| 1,929 sq.ft.	$599,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 4.44% Airbnb Rental Income: $1853 Traditional Rental Income: $3735 Airbnb ROI: 0.19% Traditional ROI: 4.44%
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: 0.12% Traditional cash on cash: 0.64% Airbnb Rental Income: $1721 Traditional Rental Income: $1668 Airbnb ROI: 0.12% Traditional ROI: 0.64%
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: -0.87% Traditional cash on cash: 1.17% Airbnb Rental Income: $1853 Traditional Rental Income: $4200 Airbnb ROI: -0.87% Traditional ROI: 1.17%
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: 0.05% Traditional cash on cash: 3.26% Airbnb Rental Income: $1692 Traditional Rental Income: $4130 Airbnb ROI: 0.05% Traditional ROI: 3.26%
7515 Hyatt Prairie Road Ashland, OR Tucked into nature's embrace, this charming cabin offers rare peace, privacy, and sweeping...	1 beds \| 1 baths \| 1,024 sq.ft.	$412,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 4.04% Airbnb Rental Income: $1721 Traditional Rental Income: $2148 Airbnb ROI: 1.71% Traditional ROI: 4.04%
5631 Old Highway 99 Ashland, OR This meticulously maintained private 20.9 acre estate features an elegant main house with ...	4 beds \| 4 baths \| 4,332 sq.ft.	$1,300,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.5% Airbnb Rental Income: $1853 Traditional Rental Income: $6292 Airbnb ROI: -0.58% Traditional ROI: 3.5%
7874 Hyatt Prairie Road Ashland, OR Wanting to get away from it all? Well, this is it, across the hwy from Hyatt Lake and minu...	3 beds \| 4 baths \| 1,990 sq.ft.	$675,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 4.91% Airbnb Rental Income: $1692 Traditional Rental Income: $4017 Airbnb ROI: 0.47% Traditional ROI: 4.91%
55 N Mountain Avenue Ashland, OR Stylish Ashland home in Ridgeview Place!Tucked in a highly desirable community just minute...	3 beds \| 2 baths \| 1,331 sq.ft.	$447,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 2.31% Airbnb Rental Income: $1692 Traditional Rental Income: $2179 Airbnb ROI: 0.02% Traditional ROI: 2.31%

Real Estate investment in Ashland, OR

There are 134 properties for sale in the city of Ashland . The median list price in Ashland is $600,000 and the average price per square foot is $266. In September 2025, the average monthly cash on cash return in Ashland is 3.00%. The average monthly rental income in Ashland is $3,298.

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

There are 134 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 $1,692.

Your search for investment property begins and ends here

Investment Property for Sale in Ashland, OR

9412 MT ASHLAND SKI RD

Ashland, OR

3 beds | 2 baths | 2,376 sq.ft.

$875,000

Airbnb cash on cash: -0.4%

Traditional cash on cash: 2.31%

Airbnb Rental Income: $1692

Traditional Rental Income: $3431

Airbnb ROI: -0.4%

Traditional ROI: 2.31%

2809 DEAD INDIAN MEMORIAL RD

Ashland, OR

3 beds | 3 baths | 2,530 sq.ft.

$880,000

Airbnb cash on cash: -0.36%

Traditional cash on cash: 2.38%

Airbnb Rental Income: $1692

Traditional Rental Income: $3471

Airbnb ROI: -0.36%

Traditional ROI: 2.38%

3729 OLD HIGHWAY 99

Ashland, OR

3 beds | 4 baths | 7,426 sq.ft.

$875,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $1692

Traditional Rental Income: $5874

Airbnb ROI: -0.92%

Traditional ROI: 4.79%

128 S Mountain Avenue

Ashland, OR

N/A beds | N/A baths | N/A

$845,000

Airbnb cash on cash: 0.21%

Traditional cash on cash: 0.42%

Airbnb Rental Income: $1853

Traditional Rental Income: $1518

Airbnb ROI: 0.21%

Traditional ROI: 0.42%

786 Pompadour Drive

Ashland, OR

4 beds | 6 baths | 5,233 sq.ft.

$3,900,000

Airbnb cash on cash: -1.18%

Traditional cash on cash: 0.31%

Airbnb Rental Income: $1853

Traditional Rental Income: $6711

Airbnb ROI: -1.18%

Traditional ROI: 0.31%

30-36 Dewey Street

Ashland, OR

N/A beds | N/A baths | N/A

$849,000

Airbnb cash on cash: 0.03%

Traditional cash on cash: 0.3%

Airbnb Rental Income: $1692

Traditional Rental Income: $1440

Airbnb ROI: 0.03%

Traditional ROI: 0.3%

451 E Ashland Lane

Ashland, OR

4 beds | 4 baths | 4,071 sq.ft.

$1,449,999

Airbnb cash on cash: -0.46%

Traditional cash on cash: 1.84%

Airbnb Rental Income: $1853

Traditional Rental Income: $4446

Airbnb ROI: -0.46%

Traditional ROI: 1.84%

970 Elkader Street

Ashland, OR

3 beds | 2 baths | 2,096 sq.ft.

$750,000

Airbnb cash on cash: -0.33%

Traditional cash on cash: 3.25%

Airbnb Rental Income: $1692

Traditional Rental Income: $3722

Airbnb ROI: -0.33%