738 S Pennsylvania Avenue, Winter Park, FL 32789

$735,000
3
BD
2
BA
1,739
SqFt

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Sold Price
$735,000
List Price
$735,000
Status
Sold
Days on Market
2
Closing Date
Jun 30, 2026
MLS#
S5151458
Property Style
Single Family
Architectural Style
Cottage, Historic
Year Built
1925
Bedrooms
3
Bathrooms
2
Living Area
1,739
Lot Size
9,525
Acres
0.22
Total Acreage
0 to less than 1/4
Legal Subdivision Name
Winter Park
MLS Area Major
Winter Park

Property Description

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.

Additional Information

Taxes
$2730
Minimum Lease
8-12 Months
Location
Historic District
Community Features
No Deed Restriction
Property Description
One Story
Zoning
R-2
Interior Layout
Ceiling Fans(s), Walk-In Closet(s)
Interior Features
Ceiling Fans(s), Walk-In Closet(s)
Floor
Wood
Appliances
Dishwasher, Gas Water Heater, Range, Refrigerator
Utilities
Cable Available, Electricity Available, Natural Gas Available, Sewer Available, Water Available
Heating
Natural Gas
Air Conditioning
Central Air
Fireplace Description
Wood Burning
Exterior Construction
Vinyl Siding, Frame
Roof
Shingle
Foundation
Crawlspace
Pool
No Pool
Garage Carport
1 Car Garage
Garage Spaces
1
Elementary School
Audubon Park K8
Middle School
Glenridge Middle
High School
Winter Park High
Flood Zone Code
X
Parcel ID
05-22-30-9400-96-070
Legal Description
TOWN OF WINTER PARK A/67 & B/86 & MISC BOOK 3/220 LOT 7 BLK 96

Listing courtesy of COMPASS FLORIDA LLC. 407-203-9441

Selling Office: MAINFRAME REAL ESTATE.

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