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.

Single Family Homes for Sale in Ashland, OR

Search for Single Family Residential for Sale in Ashland, Oregon. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 119 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
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%
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%
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%
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%
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%
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%
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%
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%
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%
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%
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: -0.56% Traditional cash on cash: 4.34% Airbnb Rental Income: $1474 Traditional Rental Income: $2969 Airbnb ROI: -0.56% 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: 0.15% Traditional cash on cash: 3.38% Airbnb Rental Income: $1529 Traditional Rental Income: $2148 Airbnb ROI: 0.15% 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: -0.17% Traditional cash on cash: 3.64% Airbnb Rental Income: $1474 Traditional Rental Income: $2820 Airbnb ROI: -0.17% 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: -0.71% Traditional cash on cash: 0.26% Airbnb Rental Income: $1474 Traditional Rental Income: $2461 Airbnb ROI: -0.71% Traditional ROI: 0.26%
525 Ashland Loop Ashland, OR Searching for the ultimate Oregon dream home and location? This is it. Nestled near the to...	4 beds \| 3 baths \| 2,964 sq.ft.	$825,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 3.74% Airbnb Rental Income: $2995 Traditional Rental Income: $4623 Airbnb ROI: 0.73% Traditional ROI: 3.74%
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.	$799,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 5.33% Airbnb Rental Income: $1474 Traditional Rental Income: $5874 Airbnb ROI: -1.16% Traditional ROI: 5.33%
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: -0.07% Traditional cash on cash: 0.64% Airbnb Rental Income: $1529 Traditional Rental Income: $1668 Airbnb ROI: -0.07% 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 \| 3 baths \| 2,530 sq.ft.	$880,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 2.38% Airbnb Rental Income: $1474 Traditional Rental Income: $3471 Airbnb ROI: -0.58% Traditional ROI: 2.38%
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: 0.18% Traditional cash on cash: 4.91% Airbnb Rental Income: $1474 Traditional Rental Income: $4017 Airbnb ROI: 0.18% Traditional ROI: 4.91%
75 Brooks Lane Ashland, OR Move-in-ready townhome with serene views across 6.5+ acres of contiguous green space propo...	3 beds \| 3 baths \| 1,832 sq.ft.	$400,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 5.49% Airbnb Rental Income: $1474 Traditional Rental Income: $3118 Airbnb ROI: -0.06% Traditional ROI: 5.49%
8612 Hwy 66 Ashland, OR Stunning new contemporary home with mountain views on 20+ private acres! Interior highlig...	3 beds \| 4 baths \| 2,451 sq.ft.	$1,550,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.49% Airbnb Rental Income: $1474 Traditional Rental Income: $4147 Airbnb ROI: -0.66% Traditional ROI: 1.49%
307 Hillcrest Street Ashland, OR Gorgeous Custom Home and Guest Cottage, Just Steps to Downtown Ashland! This lovingly desi...	3 beds \| 3 baths \| 3,159 sq.ft.	$829,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 3.18% Airbnb Rental Income: $1474 Traditional Rental Income: $4149 Airbnb ROI: -0.84% Traditional ROI: 3.18%
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: -0.26% Traditional cash on cash: 2.59% Airbnb Rental Income: $1474 Traditional Rental Income: $3687 Airbnb ROI: -0.26% Traditional ROI: 2.59%

Your search for investment property begins and ends here

Single Family Homes for Sale in Ashland, OR

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%

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%

Traditional ROI: 1.6%

2245 Colestin Road

Ashland, OR

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

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%