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
14100 Upper Applegate Road Jacksonville, OR Experience the best of Applegate Valley living just a mile from scenic Applegate Lake! Thi...	3 beds \| 2 baths \| 1,584 sq.ft.	$325,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 9.03% Airbnb Rental Income: $1164 Traditional Rental Income: $3335 Airbnb ROI: 0.67% Traditional ROI: 9.03%
1528 Morton Way Jacksonville, OR 1528 Morton Way in Jacksonville, offers a unique secluded living experience with beautiful...	3 beds \| 2 baths \| 1,992 sq.ft.	$600,000	Airbnb cash on cash: -0.13% Traditional cash on cash: 4.2% Airbnb Rental Income: $1164 Traditional Rental Income: $3209 Airbnb ROI: -0.13% Traditional ROI: 4.2%
2354 Waters Gulch Road Jacksonville, OR Tucked away in the peaceful and private Applegate Valley, this special property offers 18 ...	3 beds \| 2 baths \| 1,475 sq.ft.	$589,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 3.3% Airbnb Rental Income: $1164 Traditional Rental Income: $2625 Airbnb ROI: -0.06% Traditional ROI: 3.3%
535 N Oregon Street Jacksonville, OR Welcome to the heart of Jacksonville, Oregon. This single-story 3-bedroom, 3-bath ranch, j...	3 beds \| 3 baths \| 1,993 sq.ft.	$749,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 3.64% Airbnb Rental Income: $1164 Traditional Rental Income: $3740 Airbnb ROI: -0.6% Traditional ROI: 3.64%
245 Jackson Creek Drive Jacksonville, OR Beautiful Custom Home in Charming Jacksonville!Welcome to this stunning 4-bedroom, 3-bathr...	4 beds \| 3 baths \| 2,862 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.34% Airbnb Rental Income: $null Traditional Rental Income: $4341 Airbnb ROI: N/A Traditional ROI: 3.34%
300 Shafer Lane #A4 Jacksonville, OR Charming 2 bed, 2 bath updated condo in the beautiful town of Jacksonville! This well-main...	2 beds \| 2 baths \| 984 sq.ft.	$305,000	Airbnb cash on cash: 1.09% Traditional cash on cash: 5.29% Airbnb Rental Income: $1487 Traditional Rental Income: $2254 Airbnb ROI: 1.09% Traditional ROI: 5.29%
345 N 5th Street Jacksonville, OR Step into the charm of historic Jacksonville with this beautifully preserved, enchanting, ...	N/A beds \| N/A baths \| N/A	$699,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 2.7% Airbnb Rental Income: $1487 Traditional Rental Income: $2786 Airbnb ROI: 0.04% Traditional ROI: 2.7%
11501 Upper Applegate Road Jacksonville, OR Tucked away on a serene knoll-top, this private retreat offers breathtaking mountain views...	3 beds \| 2 baths \| 2,160 sq.ft.	$498,000	Airbnb cash on cash: -0.31% Traditional cash on cash: 6.06% Airbnb Rental Income: $1164 Traditional Rental Income: $3744 Airbnb ROI: -0.31% Traditional ROI: 6.06%
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: -0.54% Traditional cash on cash: 4.6% Airbnb Rental Income: $1164 Traditional Rental Income: $3851 Airbnb ROI: -0.54% Traditional ROI: 4.6%
379 Squirrel Lane Jacksonville, OR This stunning 3-bedroom, 2-bath home is perfectly nestled on a 1.44-acre lot, offering you...	3 beds \| 2 baths \| 1,507 sq.ft.	$569,900	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.59% Airbnb Rental Income: $1164 Traditional Rental Income: $2294 Airbnb ROI: -0.26% Traditional ROI: 2.59%
3141 Humbug Creek Road Jacksonville, OR Applegate property w/privacy backing up to BLM land. This 2004 Custom built has 4 Bdrms + ...	4 beds \| 3 baths \| 2,857 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.11% Airbnb Rental Income: $null Traditional Rental Income: $3973 Airbnb ROI: N/A Traditional ROI: 6.11%
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.	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.85% Airbnb Rental Income: $null Traditional Rental Income: $2452 Airbnb ROI: N/A Traditional ROI: 0.85%
111 McCully Lane Jacksonville, OR This charming 2 bedroom, 3 bathroom craftsman-style townhome has been beautifully customiz...	2 beds \| 3 baths \| 1,423 sq.ft.	$365,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 6.29% Airbnb Rental Income: $1487 Traditional Rental Income: $3052 Airbnb ROI: 0.45% Traditional ROI: 6.29%
425 S 1st Street Jacksonville, OR Tucked at the end of a quiet lane in Jacksonville's historic district and set on a spaciou...	3 beds \| 2 baths \| 2,239 sq.ft.	$849,808	Airbnb cash on cash: -0.64% Traditional cash on cash: 1.23% Airbnb Rental Income: $1164 Traditional Rental Income: $2267 Airbnb ROI: -0.64% Traditional ROI: 1.23%
4000 Little Applegate Road Jacksonville, OR Discover serenity on 4.58 acres in the heart of the Applegate Valley! 3,400 sq ft custom h...	4 beds \| 3 baths \| 3,400 sq.ft.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.08% Airbnb Rental Income: $null Traditional Rental Income: $4224 Airbnb ROI: N/A Traditional ROI: 2.08%
905 Sterling Creek Road Jacksonville, OR This sprawling estate spans 89+ acres of pristine land with 18 irrigated acres, offering s...	4 beds \| 3 baths \| 5,938 sq.ft.	$1,749,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.39% Airbnb Rental Income: $null Traditional Rental Income: $3980 Airbnb ROI: N/A Traditional ROI: 0.39%
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%
8060 Upper Applegate Road Jacksonville, OR Welcome to your dream retreat in the heart of Upper Applegate! This stunning 5-acre proper...	3 beds \| 2 baths \| 2,160 sq.ft.	$494,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 2.9% Airbnb Rental Income: $1164 Traditional Rental Income: $2247 Airbnb ROI: -0.27% Traditional ROI: 2.9%
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.	$898,800	Airbnb cash on cash: -0.96% Traditional cash on cash: 2.69% Airbnb Rental Income: $1164 Traditional Rental Income: $3833 Airbnb ROI: -0.96% Traditional ROI: 2.69%
110 McCully Lane Jacksonville, OR Come tour this charming townhome in the heart of historic Jacksonville! Conveniently locat...	2 beds \| 3 baths \| 1,372 sq.ft.	$399,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.19% Airbnb Rental Income: $1487 Traditional Rental Income: $2825 Airbnb ROI: 0.45% Traditional ROI: 5.19%
931 Hogan Road Jacksonville, OR WINE COUNTRY EQUESTRIAN ESTATE! 14 Acres of EFU zoned land (low property taxes), surrounde...	3 beds \| 2 baths \| 2,382 sq.ft.	$1,395,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.62% Airbnb Rental Income: $1164 Traditional Rental Income: $3943 Airbnb ROI: -0.82% Traditional ROI: 1.62%
931 Hwy 238 Jacksonville, OR Incredible Opportunity for this Home, Property and Location!!! One Acre and just minutes f...	3 beds \| 2 baths \| 1,704 sq.ft.	$480,000	Airbnb cash on cash: 0.08% Traditional cash on cash: 6.67% Airbnb Rental Income: $1164 Traditional Rental Income: $3740 Airbnb ROI: 0.08% Traditional ROI: 6.67%
327 Laurelwood Drive Jacksonville, OR Don't miss out on this architectural masterpiece located in the heart of Jacksonville with...	2 beds \| 2 baths \| 1,544 sq.ft.	$585,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 3.45% Airbnb Rental Income: $1487 Traditional Rental Income: $3068 Airbnb ROI: -0.24% Traditional ROI: 3.45%
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: 0.94% Traditional cash on cash: 6.04% Airbnb Rental Income: $1487 Traditional Rental Income: $2796 Airbnb ROI: 0.94% Traditional ROI: 6.04%
3375 Little Applegate Road Jacksonville, OR This updated 4-bed, 3.5-bath home offers 2,907 sqft of stylish living on a peaceful 6-acre...	4 beds \| 5 baths \| 2,907 sq.ft.	$674,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.24% Airbnb Rental Income: $null Traditional Rental Income: $3826 Airbnb ROI: N/A Traditional ROI: 4.24%
300 Dunlap Road Jacksonville, OR Nestled on 28 beautiful acres in the heart of the Applegate Valley, 300 Dunlap Road in Jac...	3 beds \| 3 baths \| 2,408 sq.ft.	$785,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.79% Airbnb Rental Income: $1164 Traditional Rental Income: $3848 Airbnb ROI: -0.4% Traditional ROI: 3.79%
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: 1.85% Airbnb Rental Income: $null Traditional Rental Income: $4432 Airbnb ROI: N/A Traditional ROI: 1.85%
80 Placer Hill Drive Jacksonville, OR Whether you're looking for an exceptional home for an active family, a showplace for enter...	5 beds \| 7 baths \| 6,475 sq.ft.	$3,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.26% Airbnb Rental Income: $null Traditional Rental Income: $9096 Airbnb ROI: N/A Traditional ROI: 1.26%
430 S 5th Street Jacksonville, OR Don't miss out on this gorgeous Redwood home located just steps to the best of Jacksonvill...	3 beds \| 2 baths \| 1,622 sq.ft.	$469,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 4.37% Airbnb Rental Income: $1164 Traditional Rental Income: $2817 Airbnb ROI: -0.27% Traditional ROI: 4.37%
4848 Carberry Creek Road Jacksonville, OR Immerse yourself in nature on this amazing Creek front property. Home is completely set up...	3 beds \| 2 baths \| 1,755 sq.ft.	$440,000	Airbnb cash on cash: 0.45% Traditional cash on cash: 5.4% Airbnb Rental Income: $1164 Traditional Rental Income: $2822 Airbnb ROI: 0.45% Traditional ROI: 5.4%
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.	$599,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.61% Airbnb Rental Income: $911 Traditional Rental Income: $2341 Airbnb ROI: -0.56% Traditional ROI: 2.61%
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%
10250 Sterling Creek Road Jacksonville, OR Vineyard potential! 30 acres in spectacular Sunny Southern Oregons Applegate Valley, known...	4 beds \| 2 baths \| 2,741 sq.ft.	$925,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $3697 Airbnb ROI: N/A Traditional ROI: 2.93%
225 N Oregon Street Jacksonville, OR Experience the best of Jacksonville living in this rare property offering true flexibility...	3 beds \| 3 baths \| 1,592 sq.ft.	$748,000	Airbnb cash on cash: -0.58% Traditional cash on cash: 3.16% Airbnb Rental Income: $1164 Traditional Rental Income: $3387 Airbnb ROI: -0.58% Traditional ROI: 3.16%
645 S 5th Street Jacksonville, OR SELLER LOOKING AT ALL OFFERS! Charming Home in Beautiful Jacksonville! Welcome to this del...	3 beds \| 2 baths \| 1,284 sq.ft.	$525,000	Airbnb cash on cash: -0.16% Traditional cash on cash: 4.14% Airbnb Rental Income: $1164 Traditional Rental Income: $2888 Airbnb ROI: -0.16% Traditional ROI: 4.14%
72 Upper Applegate Road Jacksonville, OR Talk about a one-of-a-kind property! This amazing gem in the heart of the Applegate Valley...	3 beds \| 2 baths \| 2,143 sq.ft.	$729,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 3.13% Airbnb Rental Income: $1164 Traditional Rental Income: $3157 Airbnb ROI: -0.37% Traditional ROI: 3.13%
220 8th Street Jacksonville, OR One of the oldest homes in Southern Oregon, the Henry Klippel house has held just four fam...	4 beds \| 4 baths \| 3,590 sq.ft.	$900,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.66% Airbnb Rental Income: $null Traditional Rental Income: $6179 Airbnb ROI: N/A Traditional ROI: 5.66%
7630 Sterling Creek Road Jacksonville, OR SELLERS MOTIVATED. LOOKING AT ALL OFFERS! Beautifully renovated 2 bed, 2 bath home on ove...	2 beds \| 2 baths \| 1,080 sq.ft.	$450,000	Airbnb cash on cash: 0.93% Traditional cash on cash: 4.13% Airbnb Rental Income: $1487 Traditional Rental Income: $2399 Airbnb ROI: 0.93% Traditional ROI: 4.13%
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.	$689,900	Airbnb cash on cash: -0.4% Traditional cash on cash: 3.61% Airbnb Rental Income: $1164 Traditional Rental Income: $3361 Airbnb ROI: -0.4% Traditional ROI: 3.61%
443 Conestoga Circle Jacksonville, OR Motivated Sellers! Spectacular home in the Historic town of Jacksonville! Gorgeous views, ...	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%

Real Estate investment in Jacksonville, OR

There are 64 properties for sale in the city of Jacksonville . The median list price in Jacksonville is $744,000 and the average price per square foot is $298. In September 2025, the average monthly cash on cash return in Jacksonville is 3.00%. The average monthly rental income in Jacksonville is $3,583.

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

There are 64 investment properties available for sale in Jacksonville.

In 2025, the best neighborhood to buy investment property is Jacksonville.

The ROI for Short-Term is higher than the Long-Term in Jacksonville with average rental income of $1,164.

Your search for investment property begins and ends here

Investment Property for Sale in Jacksonville, OR

14100 Upper Applegate Road

Jacksonville, OR

3 beds | 2 baths | 1,584 sq.ft.

$325,000

Airbnb cash on cash: 0.67%

Traditional cash on cash: 9.03%

Airbnb Rental Income: $1164

Traditional Rental Income: $3335

Airbnb ROI: 0.67%

Traditional ROI: 9.03%

1528 Morton Way

Jacksonville, OR

3 beds | 2 baths | 1,992 sq.ft.

$600,000

Airbnb cash on cash: -0.13%

Traditional cash on cash: 4.2%

Airbnb Rental Income: $1164

Traditional Rental Income: $3209

Airbnb ROI: -0.13%

Traditional ROI: 4.2%

2354 Waters Gulch Road

Jacksonville, OR

3 beds | 2 baths | 1,475 sq.ft.

$589,000

Airbnb cash on cash: -0.06%

Traditional cash on cash: 3.3%

Airbnb Rental Income: $1164

Traditional Rental Income: $2625

Airbnb ROI: -0.06%

Traditional ROI: 3.3%

535 N Oregon Street

Jacksonville, OR

3 beds | 3 baths | 1,993 sq.ft.

$749,000

Airbnb cash on cash: -0.6%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $1164

Traditional Rental Income: $3740

Airbnb ROI: -0.6%

Traditional ROI: 3.64%

245 Jackson Creek Drive

Jacksonville, OR

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

$899,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.34%

Airbnb Rental Income: $null

Traditional Rental Income: $4341

Airbnb ROI: N/A

Traditional ROI: 3.34%

300 Shafer Lane #A4

Jacksonville, OR

2 beds | 2 baths | 984 sq.ft.

$305,000

Airbnb cash on cash: 1.09%

Traditional cash on cash: 5.29%

Airbnb Rental Income: $1487

Traditional Rental Income: $2254

Airbnb ROI: 1.09%

Traditional ROI: 5.29%

345 N 5th Street

Jacksonville, OR

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

$699,000

Airbnb cash on cash: 0.04%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $1487

Traditional Rental Income: $2786

Airbnb ROI: 0.04%

Traditional ROI: 2.7%

11501 Upper Applegate Road

Jacksonville, OR

3 beds | 2 baths | 2,160 sq.ft.

$498,000

Airbnb cash on cash: -0.31%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $1164

Traditional Rental Income: $3744

Airbnb ROI: -0.31%