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Winchester, VA Short Term Rental Properties for Sale

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Turnkey Winchester Triplex Investment Opportunity
$605,000
4,396 SF

Turnkey Winchester Triplex Investment Opportunity

540 MONTICELLO Street, Winchester, VA 22601

Triplex in downtown Winchester with strong cash flow potential.

  • Turnkey triplex investment property with all units currently leased, providing immediate and reliable income.
  • Prime downtown Winchester location, offering convenience and commuter access to I‑81, I‑66, and Northern Virginia.
  • Diverse unit mix: two 2‑bedroom units with updated kitchens, laundry rooms, and a large 5‑bedroom unit with a unique two‑level layout, private patio, and deck.
  • Recent renovations including LVP flooring, fresh paint, updated kitchens and baths, and newer appliances in each unit.
  • Newer roof (less than 3 years old) and new HVAC system (installed in 2025).
Updated: Feb 17
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Based on your search, we've compiled 5 Potential Opportunities for your consideration. Besides 1 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities

Explore Opportunities in Nearby Cities

Here are 4 Similar properties we found in Nearby Locations for your consideration.

Furnished Cabins with Mountain Views
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Furnished Cabins with Mountain Views

Two fully furnished cabins on 9.5 acres with mountain views.

2225 & 2319 VALLEY BURG Rd, Luray, VA 22835
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Triplex in Prime DC Location
$955,000
2,788 SF

Triplex in Prime DC Location

Triplex with mixed-use zoning in a sought-after neighborhood.

5135 MacArthur Boulevard Northwest, Washington, DC 20016
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Student Housing Multifamily Asset
Contact for pricing
44,190 SF

Student Housing Multifamily Asset

Class A multifamily property near Woodley Park Metro station.

2807 Connecticut Ave NW, Washington, DC 20008
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Boutique Hotel Investment Opportunity
$1,999,000
11,000 SF

Boutique Hotel Investment Opportunity

Hospitality property with 12 boutique rooms in Luray, Virginia.

2 S Court St, Luray, VA 22835
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Winchester, VA Short Term Rental Properties Investment Opportunities Market Analysis

Explore 1 short term rental properties for sale in Winchester, VA on our real estate platform. These investment opportunities span a total of 0 square feet of properties for sale, with an estimated market value of $0.00.

Sale prices for short term rental properties in Winchester, VA start at $0.00, averaging $0.00, and reaching up to $0.00 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

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