738 S PENNSYLVANIA AVENUE, Winter Park, FL 32789

• 3 beds |
• 2 baths |
• 1,739 sqft

Property Description

Under contract-accepting backup offers. Experience the pinnacle of the Winter Park lifestyle in this enchanting historic cottage, offering an unbeatable, highly walkable location just a 2-minute stroll from the pristine campus of Rollins College, a 4-minute walk to the neighborhood coffee shop, and approximately 11 minutes on foot to the boutique shops, world-class dining, and scenic shores of the Winter Park Chain of Lakes along Park Avenue. Families will secure unparalleled long-term educational value with zoning for highly rated schools including Audubon Park K-8 and Winter Park High School. Stepping inside, the home's authentic character is immediately felt, anchored by beautiful real heart of pine wood flooring that flows seamlessly throughout the entire 1,739-square-foot livable layout. The private primary suite serves as a true retreat, complete with a walk-in closet and a sunlit office/flex space ideal for a remote work setup. The home also features an indoor wood-burning fire pit, adding warmth and character to the living space. Natural gas is available on-site, adding efficiency and flexibility for future upgrades, and the home benefits from a new roof installed in 2023. Situated on a rare, sweeping 9,525-square-foot lot that holds substantial land value on its own, the property offers a massive backyard oasis with ample space for a future pool and endless possibilities for outdoor living. A detached garage provides valuable storage and presents excellent potential for conversion into an accessory dwelling unit (ADU), guest house, home office, or income-producing space, subject to buyer verification and local regulations. Adding even more flexibility, an incredible attic space/storage within the home offers the opportunity to create a unique bonus room, studio, office, or creative retreat. Whether you're seeking a charming historic residence, a highly walkable lifestyle, or a property with exceptional long-term upside, this rare Winter Park offering combines character, location, land value, and future potential in a way that is increasingly difficult to find.

Listing Status:

Pending

Date Added:

June 8, 2026

Data Last Updated:

June 24, 2026 at 7:21AM

Listing Office:

COMPASS FLORIDA LLC : 407-203-9441

Listing Agent:

Justin Jodha : 689-250-8606

MLS ID:

S5151458

Interior

• General: Ceiling Fans(s)Walk-In Closet(s)
• Rooms: AtticBonus Room
• Appliances: DishwasherGas Water HeaterRangeRefrigerator
• Laundry: Inside
• Flooring: Wood
• A/C: Central Air
• Heating: Natural Gas
• Fireplace: Wood BurningFireplace

Exterior

• Style: CottageHistoric
• Other Structures: EnclosedFront Porch

Construction

• Roofing: Shingle
• Windows: ENERGY STAR Qualified Windows
• General: Vinyl SidingFrameOneCrawlspace

Location

• Road/Access: Asphalt
• Originating MLS: Stellar MLS
• County: Orange

Lot

• Zoning: R-2TOWN OF WINTER PARK A/67 & B/86 & MISC BOOK 3/220 LOT 7 BLK 9605-22-30-9400-96-070

Utilities

• Utilities: Cable AvailableElectricity AvailableNatural Gas AvailableSewer AvailableWater Available
• Water: None
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple