$735,000
Off-Market Date: 06/10/2026738 S Pennsylvania Avenue Winter Park, FL 32789
Pending MLS# S5151458
3 beds 2 baths 1,739 sq ft Single Family
Details for 738 S Pennsylvania Avenue
MLS# S5151458
Description for 738 S Pennsylvania Avenue, Winter Park, FL, 32789
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 Information
Property Type: Residential, Single Family Residence
Status: Pending
Bedrooms: 3
Bathrooms: 2
Lot Size: 0.22 Acres
Square Feet: 1,739 sq ft
Year Built: 1925
Garage: Yes
Stories: 1 Story
Construction: Vinyl Siding,Wood Frame
Subdivision: Winter Park
Foundation: Crawlspace
County: Orange
School Information
Elementary: Audubon Park K8
Middle: Glenridge Middle
High: Winter Park High
Room Information
Main Floor
Dining Room: 5x10
Primary Bedroom: 16x12
Kitchen: 12x12
Living Room: 20x14
Bathrooms
Full Baths: 2
Additonal Room Information
Laundry: Inside
Interior Features
Appliances: Gas Water Heater, Dishwasher, Range, Refrigerator
Flooring: Wood
Basement: Crawl Space
Doors/Windows: ENERGY STAR Qualified Windows
Fireplaces: Wood Burning
Additional Interior Features: Ceiling Fan(s), Walk-In Closet(s), Attic
Utilities
Sewer: Public Sewer
Other Utilities: Cable Available,Electricity Available,Natural Gas Available,Sewer Available,Water Available,Water Not Available
Cooling: Ceiling Fan(s), Central Air
Heating: Natural Gas
Exterior / Lot Features
Garage Spaces: 1
Roof: Shingle
Additional Exterior/Lot Features: Sprinkler/Irrigation, Front Porch, Enclosed, Historic District
Driving 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
Financial Considerations
Terms: Cash,Conventional,FHA,VA Loan
Tax/Property ID: 05-22-30-9400-96-070
Tax Amount: 2730.14
Tax Year: 2025
A broker reciprocity listing courtesy: COMPASS FLORIDA LLC
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Sales History & Tax Summary for 738 S Pennsylvania Avenue
Sales History
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Tax Summary
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Schools
Schools nearby 738 S Pennsylvania Avenue
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Data powered by ATTOM Data Solutions. Copyright© 2026. Information deemed reliable but not guaranteed.
The schools shown represent both the assigned schools and schools by distance based on local school and district attendance boundaries. Attendance boundaries change based on various factors and proximity does not guarantee enrollment eligibility. Please consult your real estate agent and/or the school district to confirm the schools this property is zoned to attend. Information is deemed reliable but not guaranteed.
SchoolDigger ® Rating
The SchoolDigger rating system is a 1-5 scale with 5 as the highest rating. SchoolDigger ranks schools based on test scores supplied by each state's Department of Education. They calculate an average standard score by normalizing and averaging each school's test scores across all tests and grades.
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