738 S PENNSYLVANIA AVE Winter Park, FL 32789 Pending
UPDATED: 06/10/2026 08:00 PM ON MARKET: 7 days on market
$735,000
3 Beds2 Baths1,739 SqFt
Key Details
Property Type Single Family Home
Sub Type Single Family Residence
Listing Status Pending
Purchase Type For Sale
Square Footage 1,739 sqft
Price per Sqft $422
Subdivision Winter Park
MLS Listing ID S5151458
Bedrooms 3
Full Baths 2
HOA Y/N No
Year Built 1925
Annual Tax Amount $2,730
Lot Size 9,583 Sqft
Acres 0.22
Property Sub-Type Single Family Residence
Source Stellar MLS
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.
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