For Sale
  • For Sale
  • For Lease
  • Recently Sold
  • Property Lookup
  • Brokers
Specialty
1
  • Retail
  • Office
  • Residential Income
  • Restaurants
  • Industrial
  • Mixed-Use
  • Hospitality
  • Health Care
  • Sports & Entertainment
  • Land
  • Agricultural
  • Specialty
Price
Price range
$
$
Size
Property size / sq.ft.

Winchester, VA Specialty Properties for Sale

69 results
List
Map
Downtown Winchester Triplex Investment Opportunity
$605,000
4,396 SF

Downtown Winchester Triplex Investment Opportunity

540 Monticello St, Winchester, VA 22601

Turnkey triplex in downtown Winchester with strong cash flow.

  • Turnkey triplex investment property with all units currently leased, providing immediate and reliable income.
  • Prime downtown Winchester location, commuter‑friendly with easy access to I‑81 and I‑66, and proximity to Northern Virginia.
  • Diverse unit mix: two 2‑bedroom units with updated finishes and laundry, plus a large 5‑bedroom unit with a unique two‑level layout and private outdoor space.
  • 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 2025), minimizing immediate maintenance concerns.
Updated: Feb 17
View details
Land For Sale Winchester, VA
Contact for pricing

Land For Sale Winchester, VA

Winchester, VA 22602

Land available for purchase in Winchester, Virginia.

  • Location: -78.11546, 39.17063
Updated: Oct 17, 2025
View details
Winchester Investment Property Near I-81
$1,500,000

Winchester Investment Property Near I-81

Excellent investment opportunity with a long-term tenant in Winchester, VA.

1359 Berryville Ave, Winchester, VA 22601
View details
Specialty Property for Sale
$524,000

Specialty Property for Sale

Specialty property available for purchase.

129 Old Wagon Rd, Winchester, VA 22602
View details
Winchester Specialty Property For Sale
$489,999

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

109 Shelby Ct, Winchester, VA 22602
View details
FROG HOLLOW Rd, Winchester, VA
$760,000

FROG HOLLOW Rd, Winchester, VA

Property for sale at 442 FROG HOLLOW Rd, Winchester, VA

442 Frog Hollow Rd, Winchester, VA 22603
View details
Specialty Property for Sale
$420,000

Specialty Property for Sale

Specialty property available for purchase.

103 Blue Ridge Ln, Winchester, VA 22602
View details
Webster Court Specialty Property
$549,990

Webster Court Specialty Property

Specialty property available for sale in Winchester, Virginia.

120 Webster Ct, Winchester, VA 22603
View details
Specialty Property in Winchester, VA
$369,990

Specialty Property in Winchester, VA

Specialty property available for sale in Winchester, Virginia.

106 Pomo Ln, Winchester, VA 22602
View details
Winchester Specialty Property For Sale
$795,600

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

111 Babbs Mountain Rd, Winchester, VA 22603
View details
Specialty Property For Sale
$409,900

Specialty Property For Sale

Specialty property available for purchase.

117 Tye Ct, Winchester, VA 22602
View details
Winchester Specialty Property For Sale
$815,000

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

162 Janes Way, Winchester, VA 22602
View details
Specialty Property for Sale
$300,000

Specialty Property for Sale

Specialty property available for purchase.

621 Butler Ave, Winchester, VA 22601
View details
Winchester Specialty Property For Sale
$599,990

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

121 Mascouten St, Winchester, VA 22602
View details
Alliance Court Specialty Property
$445,000

Alliance Court Specialty Property

Specialty property for sale in Winchester, Virginia.

125 Alliance Ct, Winchester, VA 22602
View details
Winchester Specialty Property For Sale
$415,000

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

290 Green St, Winchester, VA 22601
View details
Winchester Specialty Property For Sale
$1,115,000

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

207 WEST Vw Dr Dr, Winchester, VA 22603
View details
Winchester Specialty Property For Sale
$370,000

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

2431 Cedar Crk, Winchester, VA 22602
View details
Specialty Property for Sale
$430,000

Specialty Property for Sale

Specialty property available for purchase.

133 Cardinal Ln, Winchester, VA 22602
View details
Specialty Property for Sale
$1,175,000

Specialty Property for Sale

Specialty property available for purchase.

107 La Costa Ct, Winchester, VA 22602
View details
Winchester Specialty Property For Sale
$549,900

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

128 Teaberry Dr, Winchester, VA 22602
View details
Harvest Ridge Specialty Property
$649,500

Harvest Ridge Specialty Property

Specialty property available for sale in Winchester, Virginia.

150 Harvest Ridge Dr, Winchester, VA 22601
View details
Winchester Specialty Property For Sale
$960,000

Winchester Specialty Property For Sale

Specialty property available for purchase in Winchester, Virginia.

150 Ewell Dr, Winchester, VA 22602
View details
Specialty Property for Sale
$575,000

Specialty Property for Sale

Specialty property available for purchase.

1039 Hiatt Rd, Winchester, VA 22603
View details

Winchester, VA Specialty Properties Investment Opportunities Market Analysis

Explore 79 specialty properties for sale in Winchester, VA, showcased through 69 active listings on our real estate platform. These investment opportunities span a total of 5,406,998 square feet of properties for sale, with an estimated market value of $14,680,000.

Sale prices for properties in Winchester, VA start at $245,000, averaging $1,835,000, and reaching up to $9,180,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you stay ahead with the latest data and market trends.

List
Map