Real Estate Investment Properties for Sale in Jacksonville, OR

Looking for investment property in Jacksonville, OR with high ROI ?

Explore a variety of short-term homes & houses in Jacksonville, OR. Invest wisely with VRBO & Jacksonville, 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 Jacksonville, OR

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1979 Upper Applegate Road Jacksonville, OR We have cherished our time in the heart of Applegate Valley & this home has been the backd...	4 beds \| 3 baths \| 3,796 sq.ft.	$680,000	Airbnb cash on cash: N/A Traditional cash on cash: 2% Airbnb Rental Income: $null Traditional Rental Income: $2632 Airbnb ROI: N/A Traditional ROI: 2%
4460 Highway 238 Jacksonville, OR Experience the best of Jacksonville living! Just 7 minutes from historic downtown, the Bri...	2 beds \| 2 baths \| 2,244 sq.ft.	$450,000	Airbnb cash on cash: 0.02% Traditional cash on cash: 5.72% Airbnb Rental Income: $1171 Traditional Rental Income: $3191 Airbnb ROI: 0.02% Traditional ROI: 5.72%
245 Jackson Creek Drive Jacksonville, OR Welcome to your dream home in the desirable Nunan Square of Jacksonville! This 4 bedroom 3...	4 beds \| 3 baths \| 2,862 sq.ft.	$830,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $4341 Airbnb ROI: N/A Traditional ROI: 3.7%
535 Scenic Drive Jacksonville, OR Views of the City lights and mountains beyond from this large lot in the heart of Jacksonv...	3 beds \| 2 baths \| 2,339 sq.ft.	$640,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 4.6% Airbnb Rental Income: $885 Traditional Rental Income: $3851 Airbnb ROI: -0.93% Traditional ROI: 4.6%
13719 Highway 238 Jacksonville, OR Amazing Applegate River frontage for fishing, kayaking, or tubing w/private park-like grou...	4 beds \| 2 baths \| 3,056 sq.ft.	$1,075,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.89% Airbnb Rental Income: $null Traditional Rental Income: $2452 Airbnb ROI: N/A Traditional ROI: 0.89%
9395 Highway 238 Jacksonville, OR Southern Oregon mini farm offering an exceptional blend of privacy, functionality, and com...	2 beds \| 2 baths \| 1,328 sq.ft.	$375,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 3.57% Airbnb Rental Income: $1171 Traditional Rental Income: $1993 Airbnb ROI: 0.15% Traditional ROI: 3.57%
11777 Highway 238 Jacksonville, OR Welcome to Red Lily Vineyards, one of the most acclaimed vineyards in the esteemed Applega...	4 beds \| 3 baths \| 4,527 sq.ft.	$8,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.66% Airbnb Rental Income: $null Traditional Rental Income: $4104 Airbnb ROI: N/A Traditional ROI: -0.66%
4456 Highway 238 Jacksonville, OR Unique Multi Generational Jacksonville Opportunity! 2 Homes on Separate Parcels!Just 7 min...	5 beds \| 5 baths \| 4,568 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $4571 Airbnb ROI: N/A Traditional ROI: 3.46%
415 E C Street Jacksonville, OR Location, Location Location! Discover this rare piece of Southern Oregon history in this N...	3 beds \| 1 baths \| 1,021 sq.ft.	$599,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.2% Airbnb Rental Income: $885 Traditional Rental Income: $1535 Airbnb ROI: -0.56% Traditional ROI: 1.2%
1514 Sterling Creek Road Jacksonville, OR Pictures can't fully capture the beauty of this exceptionally maintained one-owner home. T...	3 beds \| 3 baths \| 2,470 sq.ft.	$885,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 1.76% Airbnb Rental Income: $885 Traditional Rental Income: $2793 Airbnb ROI: -0.96% Traditional ROI: 1.76%
7813 Upper Applegate Road Jacksonville, OR Luxurious Pagnini Custom Home on the Applegate River. Situated Far from the Road for Opti...	3 beds \| 4 baths \| 3,218 sq.ft.	$850,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.9% Airbnb Rental Income: $885 Traditional Rental Income: $3833 Airbnb ROI: -1.25% Traditional ROI: 2.9%
3361 Little Applegate Road Jacksonville, OR Handyman Special! Discover the charm and potential of this peaceful 4.77-acre property, fe...	2 beds \| 2 baths \| 1,264 sq.ft.	$365,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 6.04% Airbnb Rental Income: $1171 Traditional Rental Income: $2796 Airbnb ROI: 0.17% Traditional ROI: 6.04%
855 Wells Fargo Loop Jacksonville, OR Tucked behind an elegant, gated entryway this exquisite private estate is surrounded by th...	4 beds \| 3 baths \| 4,689 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.98% Airbnb Rental Income: $null Traditional Rental Income: $4432 Airbnb ROI: N/A Traditional ROI: 1.98%
7537 Sterling Creek Road Jacksonville, OR Owner will Carry! Privacy awaits, 20 plus acres of a nice mix of open and forested land wi...	1 beds \| 1 baths \| 1,030 sq.ft.	$550,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 2.92% Airbnb Rental Income: $574 Traditional Rental Income: $2341 Airbnb ROI: -1.07% Traditional ROI: 2.92%
4955 Sterling Creek Road Jacksonville, OR Discover this move-in ready custom home bordering BLM land, under 15 minutes from historic...	3 beds \| 2 baths \| 1,813 sq.ft.	$650,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 3.89% Airbnb Rental Income: $885 Traditional Rental Income: $3361 Airbnb ROI: -0.75% Traditional ROI: 3.89%
443 Conestoga Circle Jacksonville, OR Situated in the lovely Stagecoach Hills neighborhood, this multi-level residence embodies ...	4 beds \| 3 baths \| 3,277 sq.ft.	$1,000,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.98% Airbnb Rental Income: $null Traditional Rental Income: $4473 Airbnb ROI: N/A Traditional ROI: 2.98%
6041 Sterling Creek Road Jacksonville, OR Experience the serenity of country living in this charming two-story home set on 3.24 acre...	3 beds \| 2 baths \| 1,650 sq.ft.	$455,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.66% Airbnb Rental Income: $885 Traditional Rental Income: $2787 Airbnb ROI: -0.59% Traditional ROI: 4.66%
321 Pair A Dice Ranch Road Jacksonville, OR Masterpiece of Art in Southern Oregon, 1st time on the market! Overlooking Jacksonville Mt...	4 beds \| 6 baths \| 9,904 sq.ft.	$5,300,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.19% Airbnb Rental Income: $null Traditional Rental Income: $8367 Airbnb ROI: N/A Traditional ROI: 0.19%
913 Granite Ridge Circle Jacksonville, OR Welcome to your dream home in Jacksonville's Granite Ridge; modern luxury meets timeless c...	3 beds \| 3 baths \| 2,460 sq.ft.	$948,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 2.76% Airbnb Rental Income: $885 Traditional Rental Income: $3892 Airbnb ROI: -1.03% Traditional ROI: 2.76%
2389 Upper Applegate Road Jacksonville, OR PRICED TO SELL! Beautiful 5-acre Jacksonville retreat.Private paved drive leads to a 3-bed...	3 beds \| 3 baths \| 2,624 sq.ft.	$689,900	Airbnb cash on cash: -0.88% Traditional cash on cash: 4.85% Airbnb Rental Income: $885 Traditional Rental Income: $4236 Airbnb ROI: -0.88% Traditional ROI: 4.85%
2527 Sterling Creek Rd Jacksonville, OR 2527 Sterling Creek Rd, Jacksonville, OR 97530 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.72% Airbnb Rental Income: $792 Traditional Rental Income: $788 Airbnb ROI: -0.5% Traditional ROI: 0.72%
2541 Sterling Creek Rd Jacksonville, OR 2541 Sterling Creek Rd, Jacksonville, OR 97530 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.72% Airbnb Rental Income: $792 Traditional Rental Income: $788 Airbnb ROI: -0.5% Traditional ROI: 0.72%
238 Juanita Way Jacksonville, OR 238 Juanita Way, Jacksonville, OR 97530 \| Other	N/A beds \| N/A baths \| N/A	$139,000	Airbnb cash on cash: 0.88% Traditional cash on cash: 3.27% Airbnb Rental Income: $792 Traditional Rental Income: $789 Airbnb ROI: 0.88% Traditional ROI: 3.27%
11677 Hwy 238 Jacksonville, OR Rare RIVERFRONT SANCTUARY in Southern Oregon Wine Country - Turnkey bed & breakfast estate...	2 beds \| 2 baths \| 3,696 sq.ft.	$2,395,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 0.12% Airbnb Rental Income: $1171 Traditional Rental Income: $2870 Airbnb ROI: -0.82% Traditional ROI: 0.12%
791 OR-238 Jacksonville, OR Attractive rural property less than a mile from downtown Jacksonville with city water. Thi...	5 beds \| 4 baths \| 3,428 sq.ft.	$640,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.23% Airbnb Rental Income: $null Traditional Rental Income: $6627 Airbnb ROI: N/A Traditional ROI: 9.23%
1661 OR-238 Highway Jacksonville, OR Just 2 miles from Jacksonville, this stunning hilltop estate blends elegance, privacy, and...	4 beds \| 4 baths \| 5,759 sq.ft.	$1,525,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.41% Airbnb Rental Income: $null Traditional Rental Income: $6235 Airbnb ROI: N/A Traditional ROI: 2.41%
560 Woodberry Lane Jacksonville, OR Charming storybook home on a quiet street just a few blocks from historic downtown Jackson...	4 beds \| 2 baths \| 1,901 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $3547 Airbnb ROI: N/A Traditional ROI: 4.62%
11655 Highway 238 Jacksonville, OR Discover Applegate River Retreat, a turnkey bed & breakfast estate spanning +/-104 acres w...	2 beds \| 2 baths \| 1,806 sq.ft.	$2,995,000	Airbnb cash on cash: -0.99% Traditional cash on cash: -0.16% Airbnb Rental Income: $1171 Traditional Rental Income: $3101 Airbnb ROI: -0.99% Traditional ROI: -0.16%
126 Haven Road Jacksonville, OR This is a wonderful opportunity to own a private sanctuary so close to town! It is a beaut...	3 beds \| 2 baths \| 1,982 sq.ft.	$269,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 11.52% Airbnb Rental Income: $885 Traditional Rental Income: $3462 Airbnb ROI: 0.04% Traditional ROI: 11.52%
465 S 3rd Street Jacksonville, OR JACKSONVILLE LIFESTYLE & VALUE-ADD POTENTIAL! Welcome to the heart of historic Jacksonvill...	2 beds \| 2 baths \| 1,014 sq.ft.	$500,000	Airbnb cash on cash: -0.12% Traditional cash on cash: 3.36% Airbnb Rental Income: $1171 Traditional Rental Income: $2412 Airbnb ROI: -0.12% Traditional ROI: 3.36%
5400 Hwy 238 Jacksonville, OR Welcome to 5400 Hwy 238 - Country Living with Endless Possibilities!Nestled on 2.79 acres ...	3 beds \| 1 baths \| 1,502 sq.ft.	$425,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 3.68% Airbnb Rental Income: $885 Traditional Rental Income: $2310 Airbnb ROI: -0.74% Traditional ROI: 3.68%
75 Anna Laura Road Jacksonville, OR Nestled in the heart of the Applegate, this well-maintained manufactured home offers room ...	3 beds \| 2 baths \| 1,620 sq.ft.	$425,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 5.72% Airbnb Rental Income: $885 Traditional Rental Income: $2979 Airbnb ROI: -0.39% Traditional ROI: 5.72%
675 S 4th Street Jacksonville, OR This is the reason why people want to live in historic Jacksonville; this comfortable home...	3 beds \| 3 baths \| 3,237 sq.ft.	$659,000	Airbnb cash on cash: -1.04% Traditional cash on cash: 4.53% Airbnb Rental Income: $885 Traditional Rental Income: $3977 Airbnb ROI: -1.04% Traditional ROI: 4.53%
325 Jackson Creek Drive Jacksonville, OR Nunan Square in Jacksonville is a delightful community to call home, and this home has muc...	4 beds \| 4 baths \| 3,279 sq.ft.	$945,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.26% Airbnb Rental Income: $null Traditional Rental Income: $6152 Airbnb ROI: N/A Traditional ROI: 5.26%
205 Oak Knoll Way Jacksonville, OR Open main living areas feature engineered wood floors, a gas f/p and a chef's kitchen equi...	4 beds \| 3 baths \| 1,978 sq.ft.	$659,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.6% Airbnb Rental Income: $null Traditional Rental Income: $3985 Airbnb ROI: N/A Traditional ROI: 4.6%
7388 Upper Applegate Road Jacksonville, OR Soaring vaulted ceilings and floor-to-ceiling windows create a dramatic entrance to this c...	3 beds \| 3 baths \| 2,588 sq.ft.	$603,000	Airbnb cash on cash: -0.91% Traditional cash on cash: 4.95% Airbnb Rental Income: $885 Traditional Rental Income: $3851 Airbnb ROI: -0.91% Traditional ROI: 4.95%
115 Wells Fargo Drive Jacksonville, OR Just minutes from downtown Jacksonville, this custom Ray Williams-built home captures pano...	3 beds \| 3 baths \| 3,309 sq.ft.	$1,250,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 1.52% Airbnb Rental Income: $885 Traditional Rental Income: $3929 Airbnb ROI: -1.39% Traditional ROI: 1.52%
11609 Highway 238 Jacksonville, OR Set on 4.55+/- acres along the Applegate River, this park-like retreat features level lawn...	3 beds \| 2 baths \| 3,171 sq.ft.	$1,199,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 2.1% Airbnb Rental Income: $885 Traditional Rental Income: $4103 Airbnb ROI: -1.09% Traditional ROI: 2.1%
909 Upper Applegate Road Jacksonville, OR Fall in Love with this beautiful Modern Farmhouse. True to its 1976 character yet complete...	2 beds \| 3 baths \| 2,052 sq.ft.	$575,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 3.78% Airbnb Rental Income: $1171 Traditional Rental Income: $3062 Airbnb ROI: -0.45% Traditional ROI: 3.78%
6333 Sterling Creek Road Jacksonville, OR Welcome to your private country retreat! Custom W.L. Moore home offers 3 bedrooms, 2 baths...	3 beds \| 2 baths \| 2,205 sq.ft.	$560,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 4.86% Airbnb Rental Income: $885 Traditional Rental Income: $3494 Airbnb ROI: -0.77% Traditional ROI: 4.86%

Real Estate investment in Jacksonville, OR

There are 40 properties for sale in the city of Jacksonville . The median list price in Jacksonville is $654,500 and the average price per square foot is $231. In January 2026, the average monthly cash on cash return in Jacksonville is 3.00%. The average monthly rental income in Jacksonville is $2,833.

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

There are 40 investment properties available for sale in Jacksonville.

In 2026, the best neighborhood to buy investment property is Jacksonville.

The ROI for Long-Term is higher than the Short-Term in Jacksonville with average rental income of $2,833.

Your search for investment property begins and ends here

Investment Property for Sale in Jacksonville, OR

1979 Upper Applegate Road

Jacksonville, OR

4 beds | 3 baths | 3,796 sq.ft.

$680,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2%

Airbnb Rental Income: $null

Traditional Rental Income: $2632

Airbnb ROI: N/A

Traditional ROI: 2%

4460 Highway 238

Jacksonville, OR

2 beds | 2 baths | 2,244 sq.ft.

$450,000

Airbnb cash on cash: 0.02%

Traditional cash on cash: 5.72%

Airbnb Rental Income: $1171

Traditional Rental Income: $3191

Airbnb ROI: 0.02%

Traditional ROI: 5.72%

245 Jackson Creek Drive

Jacksonville, OR

4 beds | 3 baths | 2,862 sq.ft.

$830,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.7%

Airbnb Rental Income: $null

Traditional Rental Income: $4341

Airbnb ROI: N/A

Traditional ROI: 3.7%

535 Scenic Drive

Jacksonville, OR

3 beds | 2 baths | 2,339 sq.ft.

$640,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $885

Traditional Rental Income: $3851

Airbnb ROI: -0.93%

Traditional ROI: 4.6%

13719 Highway 238

Jacksonville, OR

4 beds | 2 baths | 3,056 sq.ft.

$1,075,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.89%

Airbnb Rental Income: $null

Traditional Rental Income: $2452

Airbnb ROI: N/A

Traditional ROI: 0.89%

9395 Highway 238

Jacksonville, OR

2 beds | 2 baths | 1,328 sq.ft.

$375,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $1171

Traditional Rental Income: $1993

Airbnb ROI: 0.15%

Traditional ROI: 3.57%

11777 Highway 238

Jacksonville, OR

4 beds | 3 baths | 4,527 sq.ft.

$8,500,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.66%

Airbnb Rental Income: $null

Traditional Rental Income: $4104

Airbnb ROI: N/A

Traditional ROI: -0.66%

4456 Highway 238

Jacksonville, OR

5 beds | 5 baths | 4,568 sq.ft.

$925,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.46%

Airbnb Rental Income: $null

Traditional Rental Income: $4571

Airbnb ROI: N/A