Winchester Retail for Sale - Winchester City
1019 Berryville Ave • Winchester, VA
Turnkey Triplex Investment — “The Queen of Winchester”
Fully Renovated • Top-Performing Airbnb • Mixed-Use Cash Cow
Offered is one of Winchester’s most iconic and profitable small multifamily assets.
1019 Berryville Ave is a fully renovated triplex featuring three distinct, income-generating units: The Queen of Winchester, Sean’s Bar, and the Juliana Suite. These units operate with extremely strong occupancy and have grossed over $5,000 per month, with peak periods even higher.
Ideal for investors seeking turnkey STR performance, stable long-term rental cash flow, or a hybrid model that maximizes NOI from day one.
PROPERTY HIGHLIGHTS
Triplex — fully renovated inside and out
Two brand-new walk-in tile showers
Updated kitchens, new flooring, modern lighting, premium finishes
Strong curb appeal and excellent visibility
Private entrances for each unit
Off-street parking
City utilities; low maintenance
Zoned for multi-unit rental use
Located minutes from Old Town Winchester, Shenandoah University, and major travel corridors
UNIT BREAKDOWN
1. The Queen of Winchester – Top-Performing Airbnb
A proven short-term rental with outstanding reviews, repeat bookings, and strong occupancy.
Features include:
Renovated interior with elegant design
New walk-in shower
Full kitchen
High nightly rates during events, weekends, and peak season
Historically one of the best-performing small STRs in Winchester
2. Sean’s Bar – Stylish & Versatile Space
A unique, professionally designed suite that functions as an STR, LTR, or creative mixed-use rental.
Custom bar build-out
Premium flooring and lighting
Updated bath
Extremely marketable aesthetic for photoshoots, extended stays, or executive rental use
3. The Juliana Suite – Modern Long-Term or STR Option
Another fully updated, turn-key unit ideal for either standard rental or Airbnb.
Renovated kitchen
New walk-in shower
Great natural light and efficient layout
Strong long-term rent potential
FINANCIAL PERFORMANCE
Grosses $5,000+ per month at times (documented STR history)
Hybrid model (Airbnb + LTR) produces consistent monthly income
Opportunity to push income further with full STR optimization
Low operating expenses due to recent renovations
WHY THIS PROPERTY WORKS
Rare, true turnkey triplex with character + modernization
Irreplaceable location with constant demand
Multiple pathways to maximize NOI
Ideal for out-of-state investors needing reliable, automated cash flow
Winchester continues to grow, driven by tourism, healthcare, and university demand
