$735,000.00
738 S PENNSYLVANIA AVENUE, WINTER PARK, FL - 32789
3 beds
2.0 baths
1,739 sqft
$735,000.00
738 S PENNSYLVANIA AVENUE, WINTER PARK, FL - 32789
Jessica Giraldo
$735,000.00
3 beds
2.0 baths
1,739 sqft
738 S PENNSYLVANIA AVENUE, WINTER PARK, FL - 32789
For Sale
Photo 1
  • Built in 1925
  • 1 garage space
  • $422.66/sqft
  • Lot size: 9,525 sqft
  • 2 days on market

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.

  • Directions: Take I-4 to Exit 87 (Fairbanks Ave). Head east on W Fairbanks Ave. Turn right onto S Orlando Ave (US-17-92 S), take an immediate left onto W Comstock Ave, then turn right onto S Pennsylvania Ave. Property is on the righ
  • County: Orange
  • Geo subdivision: WINTER PARK

Nearby Schools

Audubon Park K8

Glenridge Middle

Winter Park High

Features

Financial

Let's get in touch!

Jessica Giraldo

Jessica Giraldo

Realtor®

See also

For Sale
2418 EUSTON ROAD, WINTER PARK, FL - 32789
$724,000.00
3 bds
2.5 ba
2,228 sqft
2418 EUSTON ROAD, WINTER PARK, FL - 32789
For Sale
1036 COURTLAND STREET, ORLANDO, FL - 32804
$739,400.00
4 bds
3.0 ba
1,875 sqft
1036 COURTLAND STREET, ORLANDO, FL - 32804
For Sale
703 NICOMA TRAIL, MAITLAND, FL - 32751
$735,000.00
3 bds
2.0 ba
1,842 sqft
703 NICOMA TRAIL, MAITLAND, FL - 32751
Stellar MLS
  • Source: Stellar MLS
  • MLS #: S5151458
Listing updated: June 9, 2026 at 3:30PM
Listing provided by: Justin Jodha, COMPASS FLORIDA LLC
Last checked 8 hours ago
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