Real Estate Investment Properties for Sale in Sherwood, OR

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
30525 NE CANTER Ln Sherwood, OR A rare opportunity for multigenerational living with flexibility for up to three private q...	4 beds \| 4 baths \| 4,839 sq.ft.	$1,675,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.75% Airbnb Rental Income: $1279 Traditional Rental Income: $7095 Airbnb ROI: -1.25% Traditional ROI: 2.75%
23798 SW HERON LAKES Dr Sherwood, OR A rare find in Sherwood's desirable Woodhaven area-with no HOA in this Pinehurst Estates n...	4 beds \| 2 baths \| 2,673 sq.ft.	$724,900	Airbnb cash on cash: -0.92% Traditional cash on cash: 3.83% Airbnb Rental Income: $1279 Traditional Rental Income: $4088 Airbnb ROI: -0.92% Traditional ROI: 3.83%
21467 SW FALLOW Ter Sherwood, OR Beautifully updated and move-in ready, this two-level detached home features brand-new flo...	3 beds \| 2 baths \| 1,684 sq.ft.	$475,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 5.69% Airbnb Rental Income: $1333 Traditional Rental Income: $3681 Airbnb ROI: -0.52% Traditional ROI: 5.69%
21281 SW SIMON Ter Sherwood, OR HUGE PRICE IMPROVEMENT! Over $200K in custom renovations and upgrades-this home is for the...	5 beds \| 3 baths \| 3,130 sq.ft.	$829,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $4421 Airbnb ROI: N/A Traditional ROI: 3.3%
13254 SW AUBERGINE Ter Sherwood, OR Bring your personal touches and style to this LIGHT and BRIGHT end-unit townhouse in River...	2 beds \| 2 baths \| 1,429 sq.ft.	$429,000	Airbnb cash on cash: -1.55% Traditional cash on cash: 3.4% Airbnb Rental Income: $991 Traditional Rental Income: $2626 Airbnb ROI: -1.55% Traditional ROI: 3.4%
15262 SW WILLAMETTE St Sherwood, OR Welcome to this modern and cozy single-level home in the heart of Old Town Sherwood. This ...	3 beds \| 1 baths \| 1,112 sq.ft.	$452,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 3.89% Airbnb Rental Income: $1333 Traditional Rental Income: $2539 Airbnb ROI: 0.07% Traditional ROI: 3.89%
21069 SW MADEIRA Ter Sherwood, OR Bright & Spacious Townhome in Prime Sherwood Location! Tucked into the quiet and walkable ...	3 beds \| 2 baths \| 1,388 sq.ft.	$364,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 4.13% Airbnb Rental Income: $1333 Traditional Rental Income: $2557 Airbnb ROI: -0.66% Traditional ROI: 4.13%
23899 SW DUTSON Dr Sherwood, OR Move-In Ready 3 bed, 2 bath home on 4.43 acres in Sherwood! Vaulted ceilings through-out, ...	3 beds \| 2 baths \| 1,296 sq.ft.	$599,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.93% Airbnb Rental Income: $1333 Traditional Rental Income: $2620 Airbnb ROI: -0.11% Traditional ROI: 2.93%
22692 SW HIGHLAND Dr Sherwood, OR Beautifully remodeled single-story home located near Old Town Sherwood with BRAND NEW BACK...	3 beds \| 2 baths \| 1,616 sq.ft.	$525,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 4.61% Airbnb Rental Income: $1333 Traditional Rental Income: $3214 Airbnb ROI: -0.06% Traditional ROI: 4.61%
13552 SW BEACH PLUM Ter Sherwood, OR LIGHT and BRIGHT end-unit. townhouse in River Terrace with open floor plan and beautiful t...	2 beds \| 2 baths \| 1,429 sq.ft.	$439,900	Airbnb cash on cash: -1.5% Traditional cash on cash: 4.41% Airbnb Rental Income: $991 Traditional Rental Income: $3073 Airbnb ROI: -1.5% Traditional ROI: 4.41%
22754 SW Highland Dr Sherwood, OR *Check out the value here--best price per sqft in the area of all actives, pendings and so...	3 beds \| 1 baths \| 2,061 sq.ft.	$599,900	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.94% Airbnb Rental Income: $1333 Traditional Rental Income: $2162 Airbnb ROI: -0.28% Traditional ROI: 1.94%
21501 SW NICHOLAS VIEW Dr Sherwood, OR A custom-crafted escape with unmatched charm and potential! 2014 Craftsman-style home, set...	4 beds \| 3 baths \| 3,117 sq.ft.	$2,175,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 1.16% Airbnb Rental Income: $1279 Traditional Rental Income: $5204 Airbnb ROI: -0.98% Traditional ROI: 1.16%
24400 SW BAKER Rd Sherwood, OR This stunning,move-in-ready estate offers the perfect blend of natural splendor,functional...	3 beds \| 2 baths \| 3,360 sq.ft.	$1,725,000	Airbnb cash on cash: -1.03% Traditional cash on cash: -0.02% Airbnb Rental Income: $1333 Traditional Rental Income: $2534 Airbnb ROI: -1.03% Traditional ROI: -0.02%
22802 SW FOREST CREEK Dr unit: 200 #200 Sherwood, OR Live in the heart of Sherwood-where small-town charm meets everyday convenience. Located i...	3 beds \| 2 baths \| 1,416 sq.ft.	$325,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.94% Airbnb Rental Income: $1333 Traditional Rental Income: $2200 Airbnb ROI: -1.25% Traditional ROI: 2.94%
16738 SW GLENEAGLE Dr unit: 44G #44G Sherwood, OR **REDUCED PRICE reflects the potential future special assessment for plumbing replacement....	2 beds \| 2 baths \| 970 sq.ft.	$185,000	Airbnb cash on cash: -2.56% Traditional cash on cash: 6.88% Airbnb Rental Income: $991 Traditional Rental Income: $2297 Airbnb ROI: -2.56% Traditional ROI: 6.88%
23141 SW Curry Ridge Dr Sherwood, OR Discover your dream home in Denali Summit, crafted by JT Roth Construction, the 2023 Build...	5 beds \| 3 baths \| 5,050 sq.ft.	$2,147,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $4547 Airbnb ROI: N/A Traditional ROI: 0.27%
20875 SW CHAPMAN Rd Sherwood, OR Experience luxury living in the heart of Oregon wine country. Nestled on 20 serene acres i...	3 beds \| 2 baths \| 3,024 sq.ft.	$3,995,000	Airbnb cash on cash: -1.07% Traditional cash on cash: -0.36% Airbnb Rental Income: $1333 Traditional Rental Income: $3563 Airbnb ROI: -1.07% Traditional ROI: -0.36%
22864 SW FOREST CREEK Dr unit: 200 #200 Sherwood, OR Welcome to this beautifully maintained 3-bedroom, 2.5-bath condo offering 1,416 square fee...	3 beds \| 2 baths \| 1,416 sq.ft.	$299,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 3.91% Airbnb Rental Income: $1333 Traditional Rental Income: $2434 Airbnb ROI: -1.47% Traditional ROI: 3.91%
21698 SW BERKSHIRE Ter Sherwood, OR Motivated sellers-ask about possible seller concessions. Sale failed due to buyer financin...	3 beds \| 2 baths \| 1,529 sq.ft.	$420,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 4.72% Airbnb Rental Income: $1333 Traditional Rental Income: $2937 Airbnb ROI: -0.4% Traditional ROI: 4.72%
16645 NE LEANDER Dr Sherwood, OR Are you ready for fall in wine country? Experience the best of Oregon's wine country in th...	4 beds \| 3 baths \| 4,781 sq.ft.	$1,100,000	Airbnb cash on cash: -1% Traditional cash on cash: 2.51% Airbnb Rental Income: $1279 Traditional Rental Income: $4470 Airbnb ROI: -1% Traditional ROI: 2.51%
31430 NE Canter Ln Sherwood, OR Some homes have a feeling you just can't capture in photos. This is one of those rare find...	4 beds \| 3 baths \| 2,474 sq.ft.	$1,145,000	Airbnb cash on cash: -0.9% Traditional cash on cash: 1.88% Airbnb Rental Income: $1279 Traditional Rental Income: $3829 Airbnb ROI: -0.9% Traditional ROI: 1.88%
20498 SW ARNOLD Pl Sherwood, OR Do not miss taking advantage of the huge price reduction and a great price per square foot...	5 beds \| 2 baths \| 2,989 sq.ft.	$690,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $3896 Airbnb ROI: N/A Traditional ROI: 3.76%
22805 SW HIGHLAND Dr Sherwood, OR Versatile Two-Level Layout Near Parks and Old Town! Located in a prime Sherwood setting ne...	3 beds \| 2 baths \| 1,719 sq.ft.	$509,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.26% Airbnb Rental Income: $1333 Traditional Rental Income: $2982 Airbnb ROI: -0.07% Traditional ROI: 4.26%
18533 SW COLFELT Ln Sherwood, OR Welcome to 18533 SW Colfelt Lane a charming two-story Craftsman nestled at the edge of She...	3 beds \| 2 baths \| 1,396 sq.ft.	$549,500	Airbnb cash on cash: -0.2% Traditional cash on cash: 3.14% Airbnb Rental Income: $1333 Traditional Rental Income: $2636 Airbnb ROI: -0.2% Traditional ROI: 3.14%
23037 SW Curry Ridge Dr Sherwood, OR This is your opportunity to make this home your own and customize the finishes. Constructi...	4 beds \| 3 baths \| 3,444 sq.ft.	$1,550,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 1.68% Airbnb Rental Income: $1279 Traditional Rental Income: $4239 Airbnb ROI: -0.66% Traditional ROI: 1.68%
22754 SW Martin Ct Sherwood, OR A Bumpable Offer has Been Accepted. Nestled on a cul-de-sac in Sherwoodâs coveted Archer...	3 beds \| 3 baths \| 1,722 sq.ft.	$559,000	Airbnb cash on cash: -0.48% Traditional cash on cash: 3.75% Airbnb Rental Income: $1333 Traditional Rental Income: $3128 Airbnb ROI: -0.48% Traditional ROI: 3.75%
23484 SW Pine St Sherwood, OR SUPER CUTE!!! PHOTOS DON'T DO IT JUSTICE, this is a must see!!! One-level living with a mo...	3 beds \| 1 baths \| 1,056 sq.ft.	$439,990	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.95% Airbnb Rental Income: $1333 Traditional Rental Income: $2606 Airbnb ROI: -0.14% Traditional ROI: 3.95%
20830 SW TRAILBLAZER Pl Sherwood, OR Comfort, charm and convenience meet in this well-designed, fully applianced, and updated 4...	4 beds \| 2 baths \| 1,835 sq.ft.	$560,000	Airbnb cash on cash: -0.54% Traditional cash on cash: 4.12% Airbnb Rental Income: $1279 Traditional Rental Income: $3317 Airbnb ROI: -0.54% Traditional ROI: 4.12%
15781 SW HIGHPOINT Dr Sherwood, OR Impeccably maintained by its original owner, this 3,648 sq. ft. home is nestled on a spaci...	4 beds \| 3 baths \| 3,648 sq.ft.	$949,900	Airbnb cash on cash: -1.05% Traditional cash on cash: 4.21% Airbnb Rental Income: $1279 Traditional Rental Income: $5526 Airbnb ROI: -1.05% Traditional ROI: 4.21%
20508 SW ROY ROGERS Rd unit: 324 #324 Sherwood, OR Secure, low-maintenance living, this one-level top-floor 2 bed, 2 bath condo is located in...	2 beds \| 2 baths \| 1,292 sq.ft.	$364,900	Airbnb cash on cash: -1.88% Traditional cash on cash: 3.38% Airbnb Rental Income: $991 Traditional Rental Income: $2437 Airbnb ROI: -1.88% Traditional ROI: 3.38%
23427 SW GREENGATE Pl Sherwood, OR NEW ROOF as of November 2025! Timeless design meets everyday comfort in this Renaissance h...	4 beds \| 2 baths \| 2,489 sq.ft.	$749,900	Airbnb cash on cash: -1.16% Traditional cash on cash: 3.01% Airbnb Rental Income: $1279 Traditional Rental Income: $3794 Airbnb ROI: -1.16% Traditional ROI: 3.01%
16718 SW GLENEAGLE Dr unit: H57 #H57 Sherwood, OR Bargain Fixer Condo in Prime Sherwood Location! Condo might* finance-check with your lende...	2 beds \| 2 baths \| 970 sq.ft.	$149,999	Airbnb cash on cash: -2.94% Traditional cash on cash: 8.75% Airbnb Rental Income: $991 Traditional Rental Income: $2314 Airbnb ROI: -2.94% Traditional ROI: 8.75%
20445 SW ARNOLD Pl Sherwood, OR Beautifully remodeled home with quality finishes and thoughtful updates throughout. Main l...	5 beds \| 2 baths \| 2,822 sq.ft.	$700,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $4157 Airbnb ROI: N/A Traditional ROI: 3.88%
23608 SW EUCALYPTUS Ter Sherwood, OR NEW PRICE! Extremely well maintained one level 3 bed, 2 bath home. NEW interior paint, new...	3 beds \| 2 baths \| 1,430 sq.ft.	$518,900	Airbnb cash on cash: -0.14% Traditional cash on cash: 3.65% Airbnb Rental Income: $1333 Traditional Rental Income: $2764 Airbnb ROI: -0.14% Traditional ROI: 3.65%
22848 SW FOREST CREEK Dr unit: 200 #200 Sherwood, OR Bright and spacious corner-unit condo spanning two levels with an open-concept layout and ...	3 beds \| 2 baths \| 1,567 sq.ft.	$289,900	Airbnb cash on cash: -1.48% Traditional cash on cash: 5.37% Airbnb Rental Income: $1333 Traditional Rental Income: $2792 Airbnb ROI: -1.48% Traditional ROI: 5.37%
17000 SW BROOKMAN Rd Sherwood, OR Tucked away in a peaceful 2-acre setting surrounded by pristine farmland, this spacious mi...	4 beds \| 2 baths \| 2,664 sq.ft.	$729,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 4.7% Airbnb Rental Income: $1279 Traditional Rental Income: $4475 Airbnb ROI: -0.6% Traditional ROI: 4.7%
12925 SW BELL Rd Sherwood, OR Beautiful custom built home with spacious great room floor plan with Brazilian walnut hard...	4 beds \| 2 baths \| 3,560 sq.ft.	$1,039,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 2.67% Airbnb Rental Income: $1279 Traditional Rental Income: $4544 Airbnb ROI: -1.13% Traditional ROI: 2.67%
15416 SW DARLA KAY Ct Sherwood, OR Tucked away in a peaceful cul-de-sac and just a short stroll from downtown Sherwood, this ...	4 beds \| 3 baths \| 2,434 sq.ft.	$662,800	Airbnb cash on cash: -0.74% Traditional cash on cash: 4.11% Airbnb Rental Income: $1279 Traditional Rental Income: $3879 Airbnb ROI: -0.74% Traditional ROI: 4.11%
16045 SW RED CLOVER Ln Sherwood, OR Location is everything with this Sherwood Village home! Backing directly to Langer Park, t...	3 beds \| 2 baths \| 1,815 sq.ft.	$580,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 3.79% Airbnb Rental Income: $1333 Traditional Rental Income: $3241 Airbnb ROI: -0.49% Traditional ROI: 3.79%
23144 SW CINNAMON HILL Pl Sherwood, OR Welcome to this beautifully updated traditional home in one of Sherwood's most desirable a...	4 beds \| 2 baths \| 1,885 sq.ft.	$585,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 4.17% Airbnb Rental Income: $1279 Traditional Rental Income: $3476 Airbnb ROI: -0.59% Traditional ROI: 4.17%

Real Estate investment in Sherwood, OR

There are 46 properties for sale in the city of Sherwood . The median list price in Sherwood is $599,000 and the average price per square foot is $260. In December 2025, the average monthly cash on cash return in Sherwood is 4.00%. The average monthly rental income in Sherwood is $3,317.

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

There are 46 investment properties available for sale in Sherwood.

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

The ROI for Long-Term is higher than the Short-Term in Sherwood with average rental income of $3,317.

Your search for investment property begins and ends here

Investment Property for Sale in Sherwood, OR

30525 NE CANTER Ln

Sherwood, OR

4 beds | 4 baths | 4,839 sq.ft.

$1,675,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $1279

Traditional Rental Income: $7095

Airbnb ROI: -1.25%

Traditional ROI: 2.75%

23798 SW HERON LAKES Dr

Sherwood, OR

4 beds | 2 baths | 2,673 sq.ft.

$724,900

Airbnb cash on cash: -0.92%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $1279

Traditional Rental Income: $4088

Airbnb ROI: -0.92%

Traditional ROI: 3.83%

21467 SW FALLOW Ter

Sherwood, OR

3 beds | 2 baths | 1,684 sq.ft.

$475,000

Airbnb cash on cash: -0.52%

Traditional cash on cash: 5.69%

Airbnb Rental Income: $1333

Traditional Rental Income: $3681

Airbnb ROI: -0.52%

Traditional ROI: 5.69%

21281 SW SIMON Ter

Sherwood, OR

5 beds | 3 baths | 3,130 sq.ft.

$829,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.3%

Airbnb Rental Income: $null

Traditional Rental Income: $4421

Airbnb ROI: N/A

Traditional ROI: 3.3%

13254 SW AUBERGINE Ter

Sherwood, OR

2 beds | 2 baths | 1,429 sq.ft.

$429,000

Airbnb cash on cash: -1.55%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $991

Traditional Rental Income: $2626

Airbnb ROI: -1.55%

Traditional ROI: 3.4%

15262 SW WILLAMETTE St

Sherwood, OR

3 beds | 1 baths | 1,112 sq.ft.

$452,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $1333

Traditional Rental Income: $2539

Airbnb ROI: 0.07%

Traditional ROI: 3.89%

21069 SW MADEIRA Ter

Sherwood, OR

3 beds | 2 baths | 1,388 sq.ft.

$364,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $1333

Traditional Rental Income: $2557

Airbnb ROI: -0.66%

Traditional ROI: 4.13%

23899 SW DUTSON Dr

Sherwood, OR

3 beds | 2 baths | 1,296 sq.ft.

$599,000

Airbnb cash on cash: -0.11%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $1333

Traditional Rental Income: $2620

Airbnb ROI: -0.11%