1021 N PENNSYLVANIA AVENUE, Winter Park, FL 32789

Property Description

A rare opportunity to build your custom dream home on a cleared homesite spanning more than one-half acre in a prime Winter Park location. Large, buildable parcels of this size are becoming increasingly difficult to find, making this an exceptional offering for those seeking space, flexibility and freedom to create a custom residence. Along Pennsylvania Avenue, this expansive homesite is ready for construction, with no HOA, allowing you to bring your builder and vision to life (Building: 35% FAR approximately 7,800 square feet + excluded porches square feet, all calculations to be confirmed with your architect and City of WP Building Dept). The generous dimensions easily accommodate a substantial residence with room for a resort-style pool, expansive outdoor living areas, guest house or other amenities, creating endless possibilities. Enjoy an exceptional lifestyle just minutes from many of Winter Park's most popular destinations. Go to, bike or take a golf cart ride to the historic Winter Park 9 Golf Course, the boutiques, award-winning restaurants and sidewalk cafés of Park Avenue, the vibrant dining scene of Hannibal Square, Winter Park Village, Mead Botanical Garden and numerous parks, cultural attractions and community events. This central location also offers convenient access to Rollins College, Valencia College, highly regarded public and private schools, downtown Orlando, major hospitals, Orlando Executive Airport, Orlando International Airport and Central Florida's major roadways. Whether your vision is a timeless estate, a contemporary architectural masterpiece or a private retreat with exceptional outdoor living, this oversized homesite provides the rare canvas to bring it to life. Opportunities to purchase a cleared, build-ready parcel of more than one-half acre in Winter Park are few and far between, making this an outstanding opportunity to create a one-of-a-kind residence in one of Central Florida's established communities.

Listing Status:

Active

Date Added:

September 2, 2026

Data Last Updated:

September 28, 2026 at 7:21AM

Listing Office:

PREMIER SOTHEBY'S INTL. REALTY : 407-644-3295

Listing Agent:

Mick Night : 407-629-4446

Contact:

407-644-3295

MLS ID:

O6429124

Location

• Road/Access: City Street
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-1AWINTER PARK OASIS Z/135 LOTS 19 & 2006-22-30-9662-00-190
• Fencing: Masonry
• Current Use: Residential

Utilities

• Utilities: BB/HS Internet AvailableCable AvailableSewer AvailableWater Available
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple