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Winchester, VA Multifamily Properties for Sale

8 results
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Winchester Multifamily Investment Opportunity
$475,000
2,736 SF

Winchester Multifamily Investment Opportunity

386 Round Hill Rd, Winchester, VA 22602

Two adjacent Winchester properties totaling 1.91 acres, offered together.

  • Two adjacent income‑producing properties being sold together on 1.91 acres.
  • Proven history of positive cash flow.
  • All units are currently rented with tenants who wish to stay.
  • Each unit is separately metered, and each parcel has its own well and septic system.
  • Located minutes from Valley Health Campus, shopping, restaurants, and Rt. 37.
Updated: Dec 14, 2025
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Turnkey Winchester Duplex Opportunity
$435,000
2,152 SF

Turnkey Winchester Duplex Opportunity

26-A Jackson Ave, Winchester, VA 22601

Updated duplex in Winchester with income potential and private yards.

  • Turnkey duplex: Vacant and updated, ready for immediate occupancy or tenant placement
  • Two spacious units: Each with 2 bedrooms, 1.5 bathrooms, laundry rooms with washer and dryer hookups, and private fenced backyards
  • Strong income potential: Projected rents of approximately $1,600 per month per unit
  • Desirable location: Convenient to downtown Winchester, shopping, restaurants, and major commuter routes
  • Low maintenance: Well‑maintained property with updated interiors
Updated: Dec 14, 2025
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Winchester Multifamily Building Near Mall
$1,800,000

Winchester Multifamily Building Near Mall

14-unit apartment building near Old Town Winchester walking mall.

406 N Loudoun St, Winchester, VA 22601
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Gray Ave Apartments: Winchester, VA
$3,150,000
11,000 SF

Gray Ave Apartments: Winchester, VA

12-unit apartment building, high occupancy.

525-527 Gray Ave, Winchester, VA 22601
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Rehabilitated Multifamily Property For Sale
$334,000

Rehabilitated Multifamily Property For Sale

Recently renovated multifamily property with secure parking and included appliances.

553 Highland Ave, Winchester, VA 22601
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Winchester Multifamily Investment Opportunity
$2,490,000

Winchester Multifamily Investment Opportunity

16-unit apartment building near community park, 100% occupied.

600 Smithfield Ave, Winchester, VA 22601
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Remodeled Multi-Unit Property with Income
$1,899,000

Remodeled Multi-Unit Property with Income

Completely remodeled multi-unit property with significant rental income potential.

908 Cedar Creek Grade, Winchester, VA 22601
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New Townhome with Modern Features
$419,990

New Townhome with Modern Features

4-bedroom townhome with granite countertops and stainless steel appliances.

187 Sioux Loop, Winchester, VA 22602
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Based on your search, we've compiled 505 Potential Opportunities for your consideration. Besides 8 Active listings in Winchester, VA, we suggest exploring several alternatives: 4 properties in Nearby Cities, and similar 493 Off-Market properties to explore as potential leads

Explore Opportunities in Nearby Cities

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

Inviting Duplex in Quiet Cul-de-Sac
$269,900

Inviting Duplex in Quiet Cul-de-Sac

Duplex with spacious master, decks, and open eat-in kitchen.

129 Woodridge Ct, Stephens City, VA 22655
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Charming Condo with Nature Views
$219,900

Charming Condo with Nature Views

Spacious 2-bedroom condo with balcony, trail to lake.

114 Timberlake Ter, Stephens City, VA 22655
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Approved Site for Mixed-Use Building
$359,900

Approved Site for Mixed-Use Building

Approved site for mixed-use building in growing Inwood area.

7639 Winchester Ave, Inwood, WV 25428
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Inwood Multi-Family Development Opportunity
$359,900
6,000 SF

Inwood Multi-Family Development Opportunity

Prime Inwood location, approved plans, ready to build.

7639 Winchester Ave, Inwood, WV 25428
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Explore Off-Market Properties in Winchester, VA

Consider similar Off-Market properties in Winchester, VA. You may contact the owners directly to inquire about their potential intentions to sell. To help you make a strong first impression, we can assist by reaching out to these owners with compelling proposals created using our AI tool.

525-527 Gray Ave

525-527 Gray Ave

Multifamily properties • 11,000 SF
Value Estimation by Request
525-527 Gray Ave, Winchester, VA 22601
View details
120 Cork St

120 Cork St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,474 SF
Value Estimation
$290,000
120 Cork St, Winchester, VA 22601-5023
View details
801 Braddock St

801 Braddock St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,126 SF
Value Estimation
$215,000
801 Braddock St, Winchester, VA 22601-4054
View details
601 Woodstock Ln

601 Woodstock Ln

APARTMENT HOUSE (UNDER 5 UNITS) • 2,040 SF
Value Estimation
$365,000
601 Woodstock Ln, Winchester, VA 22601-5560
View details
23 Bond St

23 Bond St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,318 SF
Value Estimation
$410,000
23 Bond St, Winchester, VA 22601-4501
View details
1001 Franklin St

1001 Franklin St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,460 SF
Value Estimation
$350,000
1001 Franklin St, Winchester, VA 22601-5811
View details
108 Leicester St

108 Leicester St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,337 SF
Value Estimation
$335,000
108 Leicester St, Winchester, VA 22601-4616
View details
550 12th N Kent St

550 12th N Kent St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,936 SF
Value Estimation
$415,000
550 12th N Kent St, Winchester, VA 22601-5346
View details
120 Leicester St

120 Leicester St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,646 SF
Value Estimation
$370,000
120 Leicester St, Winchester, VA 22601-4616
View details
511 Loudoun St

511 Loudoun St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,738 SF
Value Estimation
$365,000
511 Loudoun St, Winchester, VA 22601-4641
View details
228 Kern St

228 Kern St

APARTMENT HOUSE (UNDER 5 UNITS) • 2,037 SF
Value Estimation
$320,000
228 Kern St, Winchester, VA 22601-5067
View details
348 Piccadilly St

348 Piccadilly St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,668 SF
Value Estimation
$265,000
348 Piccadilly St, Winchester, VA 22601-5217
View details
24 Oates Ave

24 Oates Ave

APARTMENT HOUSE (UNDER 5 UNITS) • 1,728 SF
Value Estimation
$340,000
24 Oates Ave, Winchester, VA 22601-4914
View details
446 Loudoun St

446 Loudoun St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,948 SF
Value Estimation
$155,000
446 Loudoun St, Winchester, VA 22601-4853
View details
807 Woodland Ave

807 Woodland Ave

APARTMENT HOUSE (UNDER 5 UNITS) • 1,516 SF
Value Estimation
$360,000
807 Woodland Ave, Winchester, VA 22601-5618
View details
721 Kent St

721 Kent St

APARTMENT HOUSE (UNDER 5 UNITS) • 1,768 SF
Value Estimation
$505,000
721 Kent St, Winchester, VA 22601-4665
View details

Winchester, VA Multifamily Properties Investment Opportunities Market Analysis

Explore 501 multifamily properties for sale in Winchester, VA, showcased through 8 active listings on our real estate platform. These investment opportunities span a total of 3,139,222 square feet of properties for sale, with an estimated market value of $147,060,000.

Prices for multifamily properties in Winchester, VA start at $95,000, averaging $351,818, and reaching up to $19,195,000 — offering options for a variety of budgets and business needs. Daily updated analytics ensure you have the most current data.

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