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
128 PIONEERS Road Winchester, VA Previous buyers financing fell through! Back on Market! This one went under contract right...	4 beds \| 2 baths \| 2,048 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.87% Airbnb Rental Income: $null Traditional Rental Income: $2519 Airbnb ROI: N/A Traditional ROI: 4.87%
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.	$467,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.46% Airbnb Rental Income: $null Traditional Rental Income: $3073 Airbnb ROI: N/A Traditional ROI: 5.46%
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.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.98% Airbnb Rental Income: $null Traditional Rental Income: $3501 Airbnb ROI: N/A Traditional ROI: 3.98%
133 CARDINAL Lane Winchester, VA Welcome to this well maintained and fully remodeled split foyer, tucked away in a private ...	4 beds \| 2 baths \| 1,920 sq.ft.	$430,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.6% Airbnb Rental Income: $null Traditional Rental Income: $2490 Airbnb ROI: N/A Traditional ROI: 4.6%
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: 0.15% Traditional cash on cash: 4% Airbnb Rental Income: $1372 Traditional Rental Income: $2609 Airbnb ROI: 0.15% 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.	$600,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.1% Airbnb Rental Income: $null Traditional Rental Income: $3737 Airbnb ROI: N/A Traditional ROI: 5.1%
106 FOXGLOVE Drive Winchester, VA This home is back on the market through no fault of the seller. This spacious 3BD/3.5BA Co...	3 beds \| 4 baths \| 2,686 sq.ft.	$447,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 5.3% Airbnb Rental Income: $1372 Traditional Rental Income: $2935 Airbnb ROI: 0.57% Traditional ROI: 5.3%
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.	$710,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $3385 Airbnb ROI: N/A Traditional ROI: 3.53%
105 W OATES Avenue Winchester, VA This beautifully updated and lovingly maintained home is located in the much loved heart o...	3 beds \| 2 baths \| 1,066 sq.ft.	$345,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 4.57% Airbnb Rental Income: $1372 Traditional Rental Income: $2075 Airbnb ROI: 1.11% Traditional ROI: 4.57%
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.	$555,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.3% Airbnb Rental Income: $null Traditional Rental Income: $4129 Airbnb ROI: N/A Traditional ROI: 6.3%
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.	$245,000	Airbnb cash on cash: 1.91% Traditional cash on cash: 7.34% Airbnb Rental Income: $1372 Traditional Rental Income: $2212 Airbnb ROI: 1.91% Traditional ROI: 7.34%
1950 MELVOR Lane Winchester, VA Step into this meticulously maintained colonial home, a testament to quality craftsmanship...	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%
608 KERNSTOWN Court Winchester, VA Discover the charm and serenity of suburban living at 608 Kernstown Court, nestled in the ...	4 beds \| 4 baths \| 4,101 sq.ft.	$660,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3785 Airbnb ROI: N/A Traditional ROI: 4.32%
163 DENNY Lane Winchester, VA Open House, Sunday, November 23rd 11:00am - 1:00pm. Excellent outdoor workspace and storag...	3 beds \| 2 baths \| 1,152 sq.ft.	$350,000	Airbnb cash on cash: 1.26% Traditional cash on cash: 4.97% Airbnb Rental Income: $1372 Traditional Rental Income: $2173 Airbnb ROI: 1.26% Traditional ROI: 4.97%
815 PHEASANT Drive Winchester, VA Affordable and move-in ready ranch-style home on a little more than a half acre. The matur...	2 beds \| 1 baths \| 960 sq.ft.	$245,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 4.3% Airbnb Rental Income: $1121 Traditional Rental Income: $1452 Airbnb ROI: 1.25% Traditional ROI: 4.3%
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.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2341 Airbnb ROI: N/A Traditional ROI: 3.83%
147 HARVEST RIDGE Drive Winchester, VA Active pending release-previous buyers could not sell their home. Welcome to this meticulo...	3 beds \| 3 baths \| 3,153 sq.ft.	$655,000	Airbnb cash on cash: -0.36% Traditional cash on cash: 2.56% Airbnb Rental Income: $1372 Traditional Rental Income: $2734 Airbnb ROI: -0.36% 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.	$319,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 3.86% Airbnb Rental Income: $1487 Traditional Rental Income: $1669 Airbnb ROI: 1.8% Traditional ROI: 3.86%
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.	$449,900	Airbnb cash on cash: 0.64% Traditional cash on cash: 1.63% Airbnb Rental Income: $1459 Traditional Rental Income: $1444 Airbnb ROI: 0.64% Traditional ROI: 1.63%
162 JANES Way Winchester, VA Discover this beautifully updated home on 5 private acres in the sought-after Brookneill S...	4 beds \| 4 baths \| 4,461 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.99% Airbnb Rental Income: $null Traditional Rental Income: $3435 Airbnb ROI: N/A Traditional ROI: 2.99%
222 CRESTWOOD Lane Winchester, VA Welcome home to easy, maintenance-free living in the sought-after 55+ community of Woodbro...	2 beds \| 2 baths \| 1,260 sq.ft.	$379,000	Airbnb cash on cash: -0.17% Traditional cash on cash: 3.56% Airbnb Rental Income: $1121 Traditional Rental Income: $2074 Airbnb ROI: -0.17% Traditional ROI: 3.56%
236 MILLER Street Winchester, VA Charming 3 Bedroom, 2.5 Bath Colonial just blocks from Old Town Winchester, offering easy ...	3 beds \| 3 baths \| 1,978 sq.ft.	$514,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 3.52% Airbnb Rental Income: $1372 Traditional Rental Income: $2602 Airbnb ROI: 0.09% Traditional ROI: 3.52%
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: 0.02% Traditional cash on cash: 3.68% Airbnb Rental Income: $1372 Traditional Rental Income: $2715 Airbnb ROI: 0.02% Traditional ROI: 3.68%
423 HIGHLAND Avenue Winchester, VA Charming Winchester Home - Don't Let This One Slip Away! Welcome to this beautifully refre...	3 beds \| 2 baths \| 1,300 sq.ft.	$269,000	Airbnb cash on cash: 1.88% Traditional cash on cash: 4.83% Airbnb Rental Income: $1372 Traditional Rental Income: $1701 Airbnb ROI: 1.88% Traditional ROI: 4.83%
608 GREEN Street Winchester, VA Welcome to 608 Green Street. Come make this your own space. 3-Bedroom, 1 full bath. Hardwo...	3 beds \| 1 baths \| 1,040 sq.ft.	$284,999	Airbnb cash on cash: 1.55% Traditional cash on cash: 4.46% Airbnb Rental Income: $1372 Traditional Rental Income: $1737 Airbnb ROI: 1.55% Traditional ROI: 4.46%
132 AMHERST Street Winchester, VA Price Improvement to make this Yours! Step back in time with this Beautifully preserved VI...	4 beds \| 4 baths \| 3,475 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.51% Airbnb Rental Income: $null Traditional Rental Income: $2922 Airbnb ROI: N/A Traditional ROI: 2.51%
519 FAWN Drive Winchester, VA Priced to sell! Country living at its best ! This Split foyer home offers 3 bedrooms, 3 ba...	3 beds \| 3 baths \| 2,578 sq.ft.	$304,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 7.01% Airbnb Rental Income: $1372 Traditional Rental Income: $2559 Airbnb ROI: 1.41% Traditional ROI: 7.01%
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.	$474,500	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.	$309,900	Airbnb cash on cash: 0.95% Traditional cash on cash: 3.55% Airbnb Rental Income: $1372 Traditional Rental Income: $1713 Airbnb ROI: 0.95% Traditional ROI: 3.55%
939 WOODLAND AVE Winchester, VA Motivated sellers, Price Reduced!!! Don't Miss The Boat...Need your Own Space? or you're l...	2 beds \| 2 baths \| N/A	$274,900	Airbnb cash on cash: 0.89% Traditional cash on cash: 3.02% Airbnb Rental Income: $1121 Traditional Rental Income: $1298 Airbnb ROI: 0.89% Traditional ROI: 3.02%
100 MAURY Way Winchester, VA Welcome to this Former Model Home for the Grand Nassau model by Ryan Homes - once the Winc...	3 beds \| 3 baths \| 1,678 sq.ft.	$385,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.08% Airbnb Rental Income: $1372 Traditional Rental Income: $2231 Airbnb ROI: 0.55% Traditional ROI: 4.08%
1006 S CAMERON Street Winchester, VA Welcome home to this charming 4-bedroom, 1-bath colonial perfectly situated with walking d...	4 beds \| 1 baths \| 1,732 sq.ft.	$289,500	Airbnb cash on cash: N/A Traditional cash on cash: 3.11% Airbnb Rental Income: $null Traditional Rental Income: $1414 Airbnb ROI: N/A Traditional ROI: 3.11%
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.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.72% Airbnb Rental Income: $null Traditional Rental Income: $2218 Airbnb ROI: N/A Traditional ROI: 4.72%
121 POE Drive Winchester, VA Discover this stunning and truly one-of-a-kind home, thoughtfully designed for modern livi...	4 beds \| 3 baths \| 3,514 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $2836 Airbnb ROI: N/A Traditional ROI: 2.9%
681 HILLMAN Drive Winchester, VA No HOA! Only 2 years young! Main floor bedroom + full bath! Thoughtfully designed and meti...	5 beds \| 4 baths \| 3,550 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.56% Airbnb Rental Income: $null Traditional Rental Income: $3163 Airbnb ROI: N/A Traditional ROI: 3.56%
100 WINNS Circle Winchester, VA Welcome home to Winns Circle! This lovely home is well maintained and ideally located on a...	4 beds \| 3 baths \| 2,636 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.36% Airbnb Rental Income: $null Traditional Rental Income: $3058 Airbnb ROI: N/A Traditional ROI: 6.36%
101 DELAWARE Trail Winchester, VA Looking for a vacation home? Massive Price Reduction! Fabulous remodel featuring the fines...	3 beds \| 2 baths \| 2,302 sq.ft.	$469,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.19% Airbnb Rental Income: $1372 Traditional Rental Income: $2053 Airbnb ROI: 0.69% Traditional ROI: 3.19%
110 CARTER PL Winchester, VA Contract fell through! Interest rates have gone down! Extensive Renovations: The home ha...	5 beds \| 3 baths \| N/A	$489,970	Airbnb cash on cash: N/A Traditional cash on cash: 4.37% Airbnb Rental Income: $null Traditional Rental Income: $2719 Airbnb ROI: N/A Traditional ROI: 4.37%
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%

Real Estate investment in Winchester, VA

There are 151 properties for sale in the city of Winchester . The median list price in Winchester is $422,539 and the average price per square foot is $181. In December 2025, the average monthly cash on cash return in Winchester is 4.00%. The average monthly rental income in Winchester is $2,430.

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

There are 151 investment properties available for sale in Winchester.

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

The ROI for Long-Term is higher than the Short-Term in Winchester with average rental income of $2,430.

Your search for investment property begins and ends here

Investment Property for Sale in Winchester, VA

128 PIONEERS Road

Winchester, VA

4 beds | 2 baths | 2,048 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.87%

Airbnb Rental Income: $null

Traditional Rental Income: $2519

Airbnb ROI: N/A

Traditional ROI: 4.87%

219 MILAM Drive

Winchester, VA

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

$467,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.46%

Airbnb Rental Income: $null

Traditional Rental Income: $3073

Airbnb ROI: N/A

Traditional ROI: 5.46%

226 TAGGART Drive

Winchester, VA

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

$669,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.98%

Airbnb Rental Income: $null

Traditional Rental Income: $3501

Airbnb ROI: N/A

Traditional ROI: 3.98%

133 CARDINAL Lane

Winchester, VA

4 beds | 2 baths | 1,920 sq.ft.

$430,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2490

Airbnb ROI: N/A

Traditional ROI: 4.6%

1332 RAMSEUR Lane

Winchester, VA

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

$459,000

Airbnb cash on cash: 0.15%

Traditional cash on cash: 4%

Airbnb Rental Income: $1372

Traditional Rental Income: $2609

Airbnb ROI: 0.15%

Traditional ROI: 4%

127 KINROSS Drive

Winchester, VA

5 beds | 4 baths | 3,494 sq.ft.

$600,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.1%

Airbnb Rental Income: $null

Traditional Rental Income: $3737

Airbnb ROI: N/A

Traditional ROI: 5.1%

106 FOXGLOVE Drive

Winchester, VA

3 beds | 4 baths | 2,686 sq.ft.

$447,900

Airbnb cash on cash: 0.57%

Traditional cash on cash: 5.3%

Airbnb Rental Income: $1372

Traditional Rental Income: $2935

Airbnb ROI: 0.57%

Traditional ROI: 5.3%

137 STONEBROOK Road

Winchester, VA

4 beds | 4 baths | 3,783 sq.ft.

$710,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3385

Airbnb ROI: N/A