271 N Pennsylvania Avenue — Winter Park, FL
Class-B, Newly Renovated Office or Retail Space in the Heart of Winter Park
Available for lease is a freestanding, two-story Class-B office building, currently under going renovations - offering a rare opportunity to establish your business in one of Central Florida's most sought-after and prestigious submarkets. Built in 2014 with a contemporary Winter Park aesthetic — crisp white façade and signature black-and-white awnings — the building delivers 4,868 SF of flexible office or retail space with suites ranging from 1,148 to 2,440 SF, ideal for professional service firms, boutique retailers, creative studios, medical/wellness users, or a single-tenant headquarters.
Positioned just one block off Park Avenue, tenants step directly into the energy of Winter Park's premier dining, shopping, and cultural corridor. The location blends the walkability and charm of a nationally recognized main street with the practicality of abundant on-site parking — a combination that's genuinely scarce in the Park Avenue trade area, where surface parking is at a premium. Contemporary interior and exterior finishes mean tenants inherit a polished, move-in-ready image without the cost or delay of a heavy build-out.
Why This Location Stands Out
Winter Park is one of the most affluent and stable submarkets in the Orlando MSA, anchored by high household incomes, strong daytime population, Rollins College, and a walkable, tourist-and-local destination district. Fronting Pennsylvania Avenue one block west of Park Avenue, the property captures both the professional office demand of the Central Business District and the foot traffic and prestige that draw boutique retail and service tenants.
Location & Connectivity
Park Avenue — 1 block east / ~0.1 mi (dining, shopping, Central Park, farmers market)
Hannibal Square & Winter Park Village — walkable
Winter Park SunRail Station — ~0.3 mi (walkable commuter rail to Downtown Orlando)
US-17-92 (Orlando Ave) — ~0.5 mi
SR 426 / Aloma Ave — ~1 mi
I-4 (Exit 87, Fairbanks Ave) — ~2.3 mi
Downtown Orlando — ~6 mi
Orlando Executive Airport — ~5 mi
Orlando International Airport (MCO) — ~14 mi
Jonathan Temple
McCraney Property Company
