Real Estate Investment Properties for Sale in Winchester, VA

Looking for investment property in Winchester, VA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
219 MILAM Drive Winchester, VA Welcome to 219 Milam Drive, a spacious and updated all-brick rancher tucked in a quiet nei...	4 beds \| 3 baths \| 2,654 sq.ft.	$468,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.45% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 5.45%
226 TAGGART Drive Winchester, VA Welcome to 226 Taggart Drive - a sunlit Colonial in the heart of Winchester's sought-after...	4 beds \| 4 baths \| 4,411 sq.ft.	$689,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.84% Airbnb Rental Income: $null Traditional Rental Income: $3501 Airbnb ROI: N/A Traditional ROI: 3.84%
316 VIRGINIA Avenue Winchester, VA Well maintained Colonial offering timeless character and modern potential in the heart of ...	3 beds \| 2 baths \| 1,192 sq.ft.	$338,000	Airbnb cash on cash: 6.73% Traditional cash on cash: 4.14% Airbnb Rental Income: $3402 Traditional Rental Income: $1825 Airbnb ROI: 6.73% Traditional ROI: 4.14%
2321 STONERIDGE Road Winchester, VA Must see colonial in Harvest Ridge on just over 0 .4 acre in the city of Winchester. The o...	4 beds \| 3 baths \| 3,512 sq.ft.	$625,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2979 Airbnb ROI: N/A Traditional ROI: 3.14%
109 SHELBY Court Winchester, VA Welcome to this beautiful colonial home in the sought-after Chapel Hill community. Set on ...	3 beds \| 3 baths \| 2,412 sq.ft.	$489,999	Airbnb cash on cash: 4.12% Traditional cash on cash: 4.28% Airbnb Rental Income: $3402 Traditional Rental Income: $2721 Airbnb ROI: 4.12% Traditional ROI: 4.28%
320 LINDEN DR Winchester, VA Experience generational refined living in this stunning luxury home just minutes from Winc...	4 beds \| 3 baths \| N/A	$628,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.5% Airbnb Rental Income: $null Traditional Rental Income: $2624 Airbnb ROI: N/A Traditional ROI: 2.5%
105 BUCKWOOD Lane Winchester, VA Enjoy the ease of one-level living in this spacious 2-bedroom, 2-bath home located in a we...	2 beds \| 2 baths \| 1,584 sq.ft.	$375,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 3.94% Airbnb Rental Income: $2499 Traditional Rental Income: $2189 Airbnb ROI: 3.1% Traditional ROI: 3.94%
1332 RAMSEUR Lane Winchester, VA Welcome home to a rare find in the Mews of Meadow Branch - this exceptional all-brick exte...	3 beds \| 2 baths \| 2,648 sq.ft.	$459,000	Airbnb cash on cash: 4.09% Traditional cash on cash: 4% Airbnb Rental Income: $3402 Traditional Rental Income: $2609 Airbnb ROI: 4.09% Traditional ROI: 4%
127 KINROSS Drive Winchester, VA Welcome to 127 Kinross Dr in Winchester, VA! This spacious 5-bedroom, 3.5-bath home offers...	5 beds \| 4 baths \| 3,494 sq.ft.	$620,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.91% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 4.91%
106 FOXGLOVE Drive Winchester, VA This 3BD/3.5BA Colonial combines modern upgrades with a versatile layout. The upper level ...	3 beds \| 4 baths \| 2,686 sq.ft.	$459,900	Airbnb cash on cash: 4.46% Traditional cash on cash: 5.13% Airbnb Rental Income: $3402 Traditional Rental Income: $2935 Airbnb ROI: 4.46% Traditional ROI: 5.13%
137 STONEBROOK Road Winchester, VA Perched on an elevated lot, this handsome Colonial provides panoramic views from the spaci...	4 beds \| 4 baths \| 3,783 sq.ft.	$789,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $3385 Airbnb ROI: N/A Traditional ROI: 3.07%
107 OKEEFE Drive Winchester, VA Carpeting has been replaced with rich hardwood flooring on main level. 2020 New HVAC & Roo...	4 beds \| 5 baths \| 3,076 sq.ft.	$569,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.12% Airbnb Rental Income: $null Traditional Rental Income: $4129 Airbnb ROI: N/A Traditional ROI: 6.12%
369 CHARLES Street Winchester, VA This two-story home offers classic charm with a covered front porch, fenced backyard, and ...	3 beds \| 2 baths \| 1,526 sq.ft.	$285,000	Airbnb cash on cash: 7.81% Traditional cash on cash: 6.19% Airbnb Rental Income: $3402 Traditional Rental Income: $2212 Airbnb ROI: 7.81% Traditional ROI: 6.19%
1950 MELVOR Lane Winchester, VA <html> <head> <title>1950 Melvor Ln</title> <style> body { font-family: sans-serif; margin...	4 beds \| 3 baths \| 3,108 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.47% Airbnb Rental Income: $null Traditional Rental Income: $2732 Airbnb ROI: N/A Traditional ROI: 2.47%
3980 MIDDLE Road Winchester, VA Custom, all-brick white rambler with a French Country ambience, enjoys boundaries of a lov...	4 beds \| 4 baths \| 3,504 sq.ft.	$765,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.26% Airbnb Rental Income: $null Traditional Rental Income: $3466 Airbnb ROI: N/A Traditional ROI: 3.26%
580 N BRADDOCK Street Winchester, VA Now $450,000 - Motivated Sellers + Huge Monthly Savings with 2-1 Rate Buydown! Step inside...	4 beds \| 2 baths \| 2,200 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.6% Airbnb Rental Income: $null Traditional Rental Income: $2538 Airbnb ROI: N/A Traditional ROI: 3.6%
275 GREENWOOD Road Winchester, VA Charming split-foyer home situated on a generous 13,000 sq. ft. lot with convenient access...	3 beds \| 3 baths \| 1,732 sq.ft.	$439,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 4.69% Airbnb Rental Income: $3402 Traditional Rental Income: $2611 Airbnb ROI: 4.77% Traditional ROI: 4.69%
1709 REAVES Street Winchester, VA Please take off shoes and give feedback. Step into this beautifully cared-for home featuri...	4 beds \| 2 baths \| 1,092 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.7% Airbnb Rental Income: $null Traditional Rental Income: $2341 Airbnb ROI: N/A Traditional ROI: 3.7%
147 HARVEST RIDGE Drive Winchester, VA Welcome to this meticulously cared for home in the sought-after 55+ community The Village ...	3 beds \| 3 baths \| 3,153 sq.ft.	$655,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 2.56% Airbnb Rental Income: $3402 Traditional Rental Income: $2734 Airbnb ROI: 2.41% Traditional ROI: 2.56%
125 CHESHIRE Court Winchester, VA Beautiful and well-maintained 4 bedroom, 3.5 bath townhouse at the end of a quiet cul-de-s...	4 beds \| 4 baths \| 2,261 sq.ft.	$410,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $2534 Airbnb ROI: N/A Traditional ROI: 4.67%
242 FOOTSTONE Lane Winchester, VA Peaceful Country Retreat on 4.7 Acres - Minutes from Winchester This private country home ...	1 beds \| 1 baths \| 1,348 sq.ft.	$329,900	Airbnb cash on cash: 3.67% Traditional cash on cash: 3.7% Airbnb Rental Income: $2220 Traditional Rental Income: $1669 Airbnb ROI: 3.67% Traditional ROI: 3.7%
510 N LOUDOUN Street Winchester, VA All brick 3 unit complex with off street parking and near Old Town Mall..2nd floor has 2BD...	N/A beds \| N/A baths \| 2,376 sq.ft.	$450,000	Airbnb cash on cash: 1.52% Traditional cash on cash: 1.63% Airbnb Rental Income: $1906 Traditional Rental Income: $1444 Airbnb ROI: 1.52% Traditional ROI: 1.63%
107 LACOSTA Court Winchester, VA 107 Lacosta - Private Retreat in Sought-After Ross Common Nestled on over 2 acres. This st...	4 beds \| 4 baths \| 3,888 sq.ft.	$1,175,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.69% Airbnb Rental Income: $null Traditional Rental Income: $3424 Airbnb ROI: N/A Traditional ROI: 1.69%
2623 MIDDLE Road Winchester, VA Welcome home to 2623 Middle Rd! Now with a Virtual Tour of this beautiful home! Located ne...	3 beds \| 3 baths \| 1,984 sq.ft.	$515,000	Airbnb cash on cash: 3.54% Traditional cash on cash: 3.68% Airbnb Rental Income: $3402 Traditional Rental Income: $2715 Airbnb ROI: 3.54% Traditional ROI: 3.68%
608 GREEN Street Winchester, VA Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 renovated full ba...	3 beds \| 1 baths \| 1,040 sq.ft.	$289,999	Airbnb cash on cash: 7.7% Traditional cash on cash: 4.37% Airbnb Rental Income: $3402 Traditional Rental Income: $1737 Airbnb ROI: 7.7% Traditional ROI: 4.37%
2225 HARRISON Street Winchester, VA 2225 Harrison Street located in Winchester, VA. One level living in a home remodeled in th...	3 beds \| 2 baths \| 1,300 sq.ft.	$334,900	Airbnb cash on cash: 6.46% Traditional cash on cash: 4.02% Airbnb Rental Income: $3402 Traditional Rental Income: $1880 Airbnb ROI: 6.46% Traditional ROI: 4.02%
201 PARKWAY Street Winchester, VA Freshly Renovated Charmer in Winchester! Welcome to 201 Parkway Street, a freshly updated ...	4 beds \| 4 baths \| 1,627 sq.ft.	$475,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.57% Airbnb Rental Income: $null Traditional Rental Income: $1877 Airbnb ROI: N/A Traditional ROI: 2.57%
511 GROUSE Drive Winchester, VA This is a fantastic opportunity to purchase a new construction home and have the ability t...	3 beds \| 2 baths \| 1,333 sq.ft.	$319,000	Airbnb cash on cash: 6.51% Traditional cash on cash: 3.4% Airbnb Rental Income: $3402 Traditional Rental Income: $1713 Airbnb ROI: 6.51% Traditional ROI: 3.4%
939 WOODLAND AVE Winchester, VA Price Reduced!!! Need your Own Space? or you're looking to Downsize or Just Starting Out, ...	2 beds \| 2 baths \| N/A	$287,500	Airbnb cash on cash: 5.05% Traditional cash on cash: 2.85% Airbnb Rental Income: $2499 Traditional Rental Income: $1298 Airbnb ROI: 5.05% Traditional ROI: 2.85%
100 MAURY Way Winchester, VA Welcome to this Former Model Home for the Grand Nassau Cove model by Ryan Homes - once the...	3 beds \| 3 baths \| 1,678 sq.ft.	$399,990	Airbnb cash on cash: 5% Traditional cash on cash: 3.89% Airbnb Rental Income: $3402 Traditional Rental Income: $2231 Airbnb ROI: 5% Traditional ROI: 3.89%
513 VAN FOSSEN Street Winchester, VA Welcome to 513 Van Fossen St, a beautifully updated 4-bedroom, 2.5-bathroom brick ranch co...	4 beds \| 3 baths \| 2,804 sq.ft.	$360,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $2218 Airbnb ROI: N/A Traditional ROI: 4.64%
101 DELAWARE Trail Winchester, VA Huge Price Reduction! Motivated Seller. Fabulous remodel featuring the finest materials fr...	3 beds \| 2 baths \| 2,302 sq.ft.	$489,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 3.02% Airbnb Rental Income: $3402 Traditional Rental Income: $2053 Airbnb ROI: 4.32% Traditional ROI: 3.02%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$494,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.32%
3336 HUNTING RIDGE Road Winchester, VA IMPROVED PRICE! Come home to this beautifully designed POOL HOUSE featuring 4-bedrooms, 3-...	4 beds \| 3 baths \| 3,036 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.62% Airbnb Rental Income: $null Traditional Rental Income: $3308 Airbnb ROI: N/A Traditional ROI: 4.62%
1460 PITCOCK Lane Winchester, VA Escape to Your Private Retreat - Just 10 Minutes from Winchester! Don't miss the 3D tour a...	4 beds \| 4 baths \| 4,949 sq.ft.	$1,095,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.92% Airbnb Rental Income: $null Traditional Rental Income: $3425 Airbnb ROI: N/A Traditional ROI: 1.92%
129 INDIANA Winchester, VA I am done! Large lot on private street with valley views and private. HW floors entire mai...	3 beds \| 3 baths \| 1,660 sq.ft.	$389,900	Airbnb cash on cash: 5.17% Traditional cash on cash: 4.46% Airbnb Rental Income: $3402 Traditional Rental Income: $2388 Airbnb ROI: 5.17% Traditional ROI: 4.46%
221 CRESTWOOD Lane Winchester, VA Charming well maintained corner lot unit in desirable Woodbrook Village 55 and over commun...	2 beds \| 2 baths \| 1,384 sq.ft.	$389,900	Airbnb cash on cash: 2.88% Traditional cash on cash: 2.78% Airbnb Rental Income: $2499 Traditional Rental Income: $1856 Airbnb ROI: 2.88% Traditional ROI: 2.78%
126 ARMSTRONG Place Winchester, VA All brick ranch home with 4 bedrooms close to town and a short walk to the golf course! Ma...	4 beds \| 3 baths \| 1,617 sq.ft.	$399,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.27% Airbnb Rental Income: $null Traditional Rental Income: $2603 Airbnb ROI: N/A Traditional ROI: 5.27%
540 MONTICELLO Street Winchester, VA Welcome to 540 Monticello Street, a turnkey Multi-Unit Investment Opportunity in Prime Dow...	N/A beds \| N/A baths \| 4,396 sq.ft.	$615,000	Airbnb cash on cash: 0.68% Traditional cash on cash: 0.91% Airbnb Rental Income: $1906 Traditional Rental Income: $1529 Airbnb ROI: 0.68% Traditional ROI: 0.91%
121 SWEETBRIAR Lane Winchester, VA "Private haven Rancher" on 13 plus acres with 4 Bedrooms and 3 full baths. Hardwood floors...	4 beds \| 3 baths \| 3,442 sq.ft.	$644,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.18% Airbnb Rental Income: $null Traditional Rental Income: $2788 Airbnb ROI: N/A Traditional ROI: 3.18%

Real Estate investment in Winchester, VA

There are 141 properties for sale in the city of Winchester . The median list price in Winchester is $449,950 and the average price per square foot is $187. In October 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,528.

Winchester, VA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 141 investment properties available for sale in Winchester.

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

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $3,402.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

219 MILAM Drive

Winchester, VA

4 beds | 3 baths | 2,654 sq.ft.

$468,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3073

Airbnb ROI: N/A

Traditional ROI: 5.45%

226 TAGGART Drive

Winchester, VA

4 beds | 4 baths | 4,411 sq.ft.

$689,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3501

Airbnb ROI: N/A

Traditional ROI: 3.84%

316 VIRGINIA Avenue

Winchester, VA

3 beds | 2 baths | 1,192 sq.ft.

$338,000

Airbnb cash on cash: 6.73%

Traditional cash on cash: 4.14%

Airbnb Rental Income: $3402

Traditional Rental Income: $1825

Airbnb ROI: 6.73%

Traditional ROI: 4.14%

2321 STONERIDGE Road

Winchester, VA

4 beds | 3 baths | 3,512 sq.ft.

$625,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2979

Airbnb ROI: N/A

Traditional ROI: 3.14%

109 SHELBY Court

Winchester, VA

3 beds | 3 baths | 2,412 sq.ft.

$489,999

Airbnb cash on cash: 4.12%

Traditional cash on cash: 4.28%

Airbnb Rental Income: $3402

Traditional Rental Income: $2721

Airbnb ROI: 4.12%

Traditional ROI: 4.28%

320 LINDEN DR

Winchester, VA

4 beds | 3 baths | N/A

$628,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.5%

Airbnb Rental Income: $null

Traditional Rental Income: $2624

Airbnb ROI: N/A

Traditional ROI: 2.5%

105 BUCKWOOD Lane

Winchester, VA

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

$375,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 3.94%

Airbnb Rental Income: $2499

Traditional Rental Income: $2189

Airbnb ROI: 3.1%

Traditional ROI: 3.94%

1332 RAMSEUR Lane

Winchester, VA

3 beds | 2 baths | 2,648 sq.ft.

$459,000

Airbnb cash on cash: 4.09%

Traditional cash on cash: 4%

Airbnb Rental Income: $3402

Traditional Rental Income: $2609

Airbnb ROI: 4.09%