$735,000

738 S PENNSYLVANIA AVE, Winter Park, FL 32789

Active
3
Beds
2
Baths
1,739
Sq Ft
$422
Per Sq Ft
1925
Built
0
Days Listed

About This Property

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.

Property Details

TypeSingle Family Residence
Garage1 spaces
Lot0.22 ac
Stories1
PoolNo
WaterfrontNo
SubdivisionWINTER PARK
HOANo
Tax/yr$2,730
HeatingNatural Gas
CoolingCentral Air
FlooringWood
RoofShingle

Schools

ElementaryAudubon Park K8
MiddleGlenridge Middle
High SchoolWinter Park High

Listed by COMPASS FLORIDA LLC · MLS# MFRS5151458

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Listing information © 2026 My Florida Regional MLS DBA Stellar MLS. All Rights Reserved. Data deemed reliable but not guaranteed. Last updated: 2026-06-08.
IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
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Rise Team · LPT Realty, LLC
Mike Valdes
Mike Valdes
Rise Team · LPT Realty
(813) 548-5618
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