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
23104 SW CINNAMON HILL PL Sherwood, OR Fresh Interior Paint. Nestled on a quiet cul-de-sac, this beautiful home offers elevated l...	4 beds \| 3 baths \| 1,733 sq.ft.	$539,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.93% Airbnb Rental Income: $2297 Traditional Rental Income: $3097 Airbnb ROI: 1.2% Traditional ROI: 3.93%
30525 NE CANTER LN Sherwood, OR A rare opportunity for multigenerational living with flexibility for up to three private q...	4 beds \| 5 baths \| 4,839 sq.ft.	$1,675,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.75% Airbnb Rental Income: $2297 Traditional Rental Income: $7095 Airbnb ROI: -0.71% Traditional ROI: 2.75%
23798 SW HERON LAKES DR Sherwood, OR A rare find in Sherwoodâs desirable Woodhaven areaâwith no HOA in this Pinehurst Estat...	4 beds \| 3 baths \| 2,673 sq.ft.	$724,900	Airbnb cash on cash: 0.34% Traditional cash on cash: 3.83% Airbnb Rental Income: $2297 Traditional Rental Income: $4088 Airbnb ROI: 0.34% Traditional ROI: 3.83%
21281 SW SIMON TER Sherwood, OR HUGE PRICE IMPROVEMENT! Over $200K in custom renovations and upgradesâthis home is for t...	5 beds \| 3 baths \| 3,130 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.2% Airbnb Rental Income: $null Traditional Rental Income: $4421 Airbnb ROI: N/A Traditional ROI: 3.2%
13254 SW AUBERGINE TER Sherwood, OR LIGHT and BRIGHT end-unit townhouse in River Terrace with open floor plan and beautiful to...	2 beds \| 3 baths \| 1,429 sq.ft.	$429,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 3.4% Airbnb Rental Income: $1594 Traditional Rental Income: $2626 Airbnb ROI: -0.3% 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.	$469,900	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.71% Airbnb Rental Income: $1629 Traditional Rental Income: $2539 Airbnb ROI: 0.6% Traditional ROI: 3.71%
21069 SW MADEIRA TER Sherwood, OR Bright & Spacious Townhome in Prime Sherwood Location! Tucked into the quiet and walkable ...	3 beds \| 3 baths \| 1,388 sq.ft.	$364,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.13% Airbnb Rental Income: $1629 Traditional Rental Income: $2557 Airbnb ROI: 0.06% 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: 0.33% Traditional cash on cash: 2.93% Airbnb Rental Income: $1629 Traditional Rental Income: $2620 Airbnb ROI: 0.33% Traditional ROI: 2.93%
22692 SW HIGHLAND DR Sherwood, OR Project currently underway to remodel the backyard by removing the pool and landscaping a ...	3 beds \| 2 baths \| 1,616 sq.ft.	$525,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 4.61% Airbnb Rental Income: $1629 Traditional Rental Income: $3214 Airbnb ROI: 0.44% Traditional ROI: 4.61%
17261 SW GREENGATE DR Sherwood, OR Welcome to Your Sherwood Dream Home! This beautifully updated, turn-key single-level home ...	3 beds \| 2 baths \| 1,619 sq.ft.	$575,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 4.1% Airbnb Rental Income: $1629 Traditional Rental Income: $3337 Airbnb ROI: 0.06% Traditional ROI: 4.1%
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 \| 3 baths \| 1,429 sq.ft.	$439,900	Airbnb cash on cash: -0.07% Traditional cash on cash: 4.63% Airbnb Rental Income: $1594 Traditional Rental Income: $3073 Airbnb ROI: -0.07% Traditional ROI: 4.63%
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 \| 2 baths \| 2,061 sq.ft.	$599,900	Airbnb cash on cash: 0.17% Traditional cash on cash: 1.94% Airbnb Rental Income: $1629 Traditional Rental Income: $2162 Airbnb ROI: 0.17% Traditional ROI: 1.94%
22219 SW ORLAND ST Sherwood, OR Welcome to your dream home! This stunning brand-new manufactured home offers 3 bedrooms an...	3 beds \| 2 baths \| 1,512 sq.ft.	$400,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 5.64% Airbnb Rental Income: $1629 Traditional Rental Income: $2844 Airbnb ROI: 1.17% Traditional ROI: 5.64%
21501 SW NICHOLAS VIEW DR Sherwood, OR A custom-crafted escape with unmatched charm and potential! 2014 Craftsman-style home, set...	4 beds \| 4 baths \| 3,117 sq.ft.	$2,175,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 1.16% Airbnb Rental Income: $2297 Traditional Rental Income: $5204 Airbnb ROI: -0.56% 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 \| 3 baths \| 3,360 sq.ft.	$1,725,000	Airbnb cash on cash: -0.88% Traditional cash on cash: -0.02% Airbnb Rental Income: $1629 Traditional Rental Income: $2534 Airbnb ROI: -0.88% Traditional ROI: -0.02%
22802 SW FOREST CREEK DR #200 Sherwood, OR Live in the heart of Sherwoodâwhere small-town charm meets everyday convenience. Located...	3 beds \| 3 baths \| 1,416 sq.ft.	$325,000	Airbnb cash on cash: -0.44% Traditional cash on cash: 2.94% Airbnb Rental Income: $1629 Traditional Rental Income: $2200 Airbnb ROI: -0.44% Traditional ROI: 2.94%
16738 SW GLENEAGLE DR #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: 0.3% Traditional cash on cash: 6.88% Airbnb Rental Income: $1594 Traditional Rental Income: $2297 Airbnb ROI: 0.3% 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%
16725 NE MOUNTAIN HOME RD Sherwood, OR Take a deep breath and relax in your wine country oasis and feel like you are on vacation ...	4 beds \| 5 baths \| 6,714 sq.ft.	$3,995,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.36% Airbnb Rental Income: $2297 Traditional Rental Income: $6664 Airbnb ROI: -0.97% Traditional ROI: 0.36%
22802 SW FOREST CREEK DR #101 Sherwood, OR Not going to beat this price! Motivated Seller! Please excuse the construction work from ...	1 beds \| 1 baths \| 749 sq.ft.	$200,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 6.16% Airbnb Rental Income: $1001 Traditional Rental Income: $1977 Airbnb ROI: -0.86% Traditional ROI: 6.16%
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% Traditional cash on cash: -0.36% Airbnb Rental Income: $1629 Traditional Rental Income: $3563 Airbnb ROI: -1% Traditional ROI: -0.36%
22864 SW FOREST CREEK DR #200 Sherwood, OR Welcome to this beautifully maintained 3-bedroom, 2.5-bath condo offering 1,416 square fee...	3 beds \| 3 baths \| 1,416 sq.ft.	$299,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 3.91% Airbnb Rental Income: $1629 Traditional Rental Income: $2434 Airbnb ROI: -0.59% Traditional ROI: 3.91%
23072 SW MANSFIELD ST Sherwood, OR Custom built home in 2018 w/ dual living( separate entrance & 2 kitchens) - Seller has app...	3 beds \| 3 baths \| 3,349 sq.ft.	$779,900	Airbnb cash on cash: -0.53% Traditional cash on cash: 3.51% Airbnb Rental Income: $1629 Traditional Rental Income: $4105 Airbnb ROI: -0.53% Traditional ROI: 3.51%
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: -0.17% Traditional cash on cash: 2.51% Airbnb Rental Income: $2297 Traditional Rental Income: $4470 Airbnb ROI: -0.17% Traditional ROI: 2.51%
17215 SW ROOSEVELT ST Sherwood, OR Welcome to this beautifully maintained 2,357 sq. ft. home nestled in one of Sherwoodâs m...	4 beds \| 3 baths \| 2,357 sq.ft.	$649,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 3.78% Airbnb Rental Income: $2297 Traditional Rental Income: $3757 Airbnb ROI: 0.43% Traditional ROI: 3.78%
21615 SW DERBY TER Sherwood, OR WOW- check out this price per square feet- amazing value! OPEN HOUSE 11-1 SATURDAY 11/8. E...	5 beds \| 3 baths \| 3,288 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.13% Airbnb Rental Income: $null Traditional Rental Income: $4285 Airbnb ROI: N/A Traditional ROI: 4.13%
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: -0.1% Traditional cash on cash: 1.88% Airbnb Rental Income: $2297 Traditional Rental Income: $3829 Airbnb ROI: -0.1% 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 \| 3 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: 0.45% Traditional cash on cash: 4.26% Airbnb Rental Income: $1629 Traditional Rental Income: $2982 Airbnb ROI: 0.45% 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 \| 3 baths \| 1,396 sq.ft.	$549,500	Airbnb cash on cash: 0.28% Traditional cash on cash: 3.14% Airbnb Rental Income: $1629 Traditional Rental Income: $2636 Airbnb ROI: 0.28% Traditional ROI: 3.14%
22320 SW MOUNTAIN HOME RD Sherwood, OR A rare find at the corner of Mountain Home and Kruger, this 4.6-acre property offers a pea...	5 beds \| 3 baths \| 1,840 sq.ft.	$745,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.38% Airbnb Rental Income: $null Traditional Rental Income: $3701 Airbnb ROI: N/A Traditional ROI: 3.38%
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: -0.07% Traditional cash on cash: 1.68% Airbnb Rental Income: $2297 Traditional Rental Income: $4239 Airbnb ROI: -0.07% Traditional ROI: 1.68%
22754 SW Martin Ct Sherwood, OR Nestled on a cul-de-sac in Sherwoodâs coveted Archerâs Ridge, this 3-bed, 2.5-bath hom...	3 beds \| 3 baths \| 1,722 sq.ft.	$559,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 3.75% Airbnb Rental Income: $1629 Traditional Rental Income: $3128 Airbnb ROI: -0.01% Traditional ROI: 3.75%
23484 SW Pine ST Sherwood, OR One-level living with a modern vibe ON the Snyder Park block (dog park, tennis/pickleball/...	3 beds \| 1 baths \| 1,056 sq.ft.	$444,990	Airbnb cash on cash: 0.54% Traditional cash on cash: 3.99% Airbnb Rental Income: $1629 Traditional Rental Income: $2606 Airbnb ROI: 0.54% Traditional ROI: 3.99%
20830 SW TRAILBLAZER PL Sherwood, OR Comfort, charm and convenience meet in this well-designed, fully applianced, and updated 4...	4 beds \| 3 baths \| 1,835 sq.ft.	$560,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 4.12% Airbnb Rental Income: $2297 Traditional Rental Income: $3317 Airbnb ROI: 1.08% Traditional ROI: 4.12%
15781 SW HIGHPOINT DR Sherwood, OR Open Sun 11/16 1-4pm Impeccably maintained by its original owner, this 3,648 sq. ft. home...	4 beds \| 4 baths \| 3,648 sq.ft.	$949,900	Airbnb cash on cash: -0.09% Traditional cash on cash: 4.21% Airbnb Rental Income: $2297 Traditional Rental Income: $5526 Airbnb ROI: -0.09% Traditional ROI: 4.21%
20508 SW ROY ROGERS RD #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: -0.41% Traditional cash on cash: 3.38% Airbnb Rental Income: $1594 Traditional Rental Income: $2437 Airbnb ROI: -0.41% Traditional ROI: 3.38%
23427 SW GREENGATE PL Sherwood, OR Timeless design meets everyday comfort in this Renaissance home on sought-after Greengate....	4 beds \| 3 baths \| 2,489 sq.ft.	$749,900	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.05% Airbnb Rental Income: $2297 Traditional Rental Income: $3794 Airbnb ROI: 0.09% Traditional ROI: 3.05%
16718 SW GLENEAGLE DR #H57 Sherwood, OR Bargain Fixer Condo in Prime Sherwood Location! CASH ONLY - Sold AS-IS. This condo is pric...	2 beds \| 2 baths \| 970 sq.ft.	$149,999	Airbnb cash on cash: 0.57% Traditional cash on cash: 8.75% Airbnb Rental Income: $1594 Traditional Rental Income: $2314 Airbnb ROI: 0.57% Traditional ROI: 8.75%
22836 SW FOREST CREEK DR #201 Sherwood, OR Beautifully Maintained Townhome in Prime Location! This 3-bedroom, 2.5-bath home offers an...	3 beds \| 3 baths \| 1,550 sq.ft.	$300,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 4.8% Airbnb Rental Income: $1629 Traditional Rental Income: $2715 Airbnb ROI: -0.67% Traditional ROI: 4.8%

Real Estate investment in Sherwood, OR

There are 52 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 $257. In November 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 52 investment properties available for sale in Sherwood.

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

The ROI for Short-Term is higher than the Long-Term in Sherwood with average rental income of $1,629.

Your search for investment property begins and ends here

Investment Property for Sale in Sherwood, OR

23104 SW CINNAMON HILL PL

Sherwood, OR

4 beds | 3 baths | 1,733 sq.ft.

$539,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.93%

Airbnb Rental Income: $2297

Traditional Rental Income: $3097

Airbnb ROI: 1.2%

Traditional ROI: 3.93%

30525 NE CANTER LN

Sherwood, OR

4 beds | 5 baths | 4,839 sq.ft.

$1,675,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 2.75%

Airbnb Rental Income: $2297

Traditional Rental Income: $7095

Airbnb ROI: -0.71%

Traditional ROI: 2.75%

23798 SW HERON LAKES DR

Sherwood, OR

4 beds | 3 baths | 2,673 sq.ft.

$724,900

Airbnb cash on cash: 0.34%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $2297

Traditional Rental Income: $4088

Airbnb ROI: 0.34%

Traditional ROI: 3.83%

21281 SW SIMON TER

Sherwood, OR

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

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.2%

Airbnb Rental Income: $null

Traditional Rental Income: $4421

Airbnb ROI: N/A

Traditional ROI: 3.2%

13254 SW AUBERGINE TER

Sherwood, OR

2 beds | 3 baths | 1,429 sq.ft.

$429,000

Airbnb cash on cash: -0.3%

Traditional cash on cash: 3.4%

Airbnb Rental Income: $1594

Traditional Rental Income: $2626

Airbnb ROI: -0.3%

Traditional ROI: 3.4%

15262 SW WILLAMETTE ST

Sherwood, OR

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

$469,900

Airbnb cash on cash: 0.6%

Traditional cash on cash: 3.71%

Airbnb Rental Income: $1629

Traditional Rental Income: $2539

Airbnb ROI: 0.6%

Traditional ROI: 3.71%

21069 SW MADEIRA TER

Sherwood, OR

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

$364,000

Airbnb cash on cash: 0.06%

Traditional cash on cash: 4.13%

Airbnb Rental Income: $1629

Traditional Rental Income: $2557

Airbnb ROI: 0.06%

Traditional ROI: 4.13%

23899 SW DUTSON DR

Sherwood, OR

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

$599,000

Airbnb cash on cash: 0.33%

Traditional cash on cash: 2.93%

Airbnb Rental Income: $1629

Traditional Rental Income: $2620

Airbnb ROI: 0.33%