738 S PENNSYLVANIA AVENUE Winter Park, FL $ 735,000
738 S PENNSYLVANIA AVENUE
$ 735,000
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738 S PENNSYLVANIA AVENUE

Winter Park, FL, 32789
$ 735,000
Bedrooms3 Baths2.0 Sq 1,739

Monthly Estimate*

$ 4,526

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Single Family Home for sale in Winter Park, FL

for $735,000 with 3 bedrooms and 2 full baths. This 1,739 square foot home was built in 1925 on a lot size of 0.22.

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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Single Family Pending

Price

$ 735,000

Bedrooms

3

Full Bath

2

Property Type

Single Family

Taxes

$ 2,730

Style

Cottage Historical

Lot Size

0.22

Year Built

1925

Town/City

Winter Park

County/Region

Orange

MLS | Web ID

S5151458

Features
General
Sewer Public Sewer
Heating Natural Gas
Cooling Central Air
Utilities Cable Available Electricity Available Natural Gas Available Sewer Available Water Available
Roof Shingle
Appliances Dishwasher Gas Water Heater Range Refrigerator
Zoning R-2
Garage Spaces 1
Patio/Porch Features Enclosed Front Porch
Architectural Style Cottage Historical
Construction Materials Vinyl Siding Wood Frame
Year Built 1925
Levels One
Property Subtype Single Family Residence
Tax Year 2025
Ownership Fee Simple
County Orange
New Construction false
Property Type Residential
Attached Garage false
Subdivision Name WINTER PARK
Facing Direction West
Garage Y/N true
Total Rooms 4
Full Baths 2
Status Pending
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
High School Winter Park High
City WINTER PARK
Senior Community Y/N false
MLS Area 32789 - Winter Park
Lot Size Units Square Feet
Lot Size Square Feet 9525
Carport Y/N false
Listing Terms Cash Conventional FHA VA Loan
Elementary School Audubon Park K8
Land Lease Y/N false
Tax Annual Amount 2730.14
Middle/Junior High School Glenridge Middle
Additional Parcels Y/N false
Lease Considered Y/N true
Virtual Tour https://www.propertypanorama.com/instaview/stellar/S5151458
Building Area Units Square Feet
Living Area Units Square Feet
Standard Status Pending
Occupancy Type Vacant
Tax Lot 7
Legal Description TOWN OF WINTER PARK A/67 & B/86 & MISC BOOK 3/220 LOT 7 BLK 96
Minimum Lease 8-12 Months
Water Access Y/N false
Additional Rooms Attic Bonus Room
Water View Y/N false
Flood Zone Code X
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Interior
Interior Amenities Ceiling Fan(s) Walk-In Closet(s)
Flooring Hardwood
Furnished Y/N Unfurnished
Fireplace Features Wood Burning
Total Stories 1
Air Conditioning Y/N true
Heating Y/N true
Window Features ENERGY STAR Qualified Windows
Fireplace Y/N true
Half Baths 0
Laundry Features Inside
Total Bedrooms 3
Total Baths 2
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Exterior
Exterior Amenities Irrigation System
Lot Features Historic District
Water Source None
Lot Size Area 9525
Foundation Details Crawlspace
Building Area Total 2099
Lot Size Acres 0.22
Road Surface Type Asphalt
Private Pool false
Waterfront Y/N false
Covered Spaces 1
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* Excluded Features
List By
Compass Florida Llc

Broker

justin.jodha@compass.com

Email

Affordability Calculator

$4,753
Per Month
95%
5%
0%
Monthly Principal & Interest
$4,526
Monthly Property Taxes
$228
Monthly Home Insurance
--
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
0 Elementary School
0 Middle School
Winter Park High High School High School
Pricing History
DatePricePrice ChangeDescription
6/8/2026$735,000 Listed Price

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738 S PENNSYLVANIA AVENUE, Winter Park, FL, 32789 is a Single Family Home for sale at $735,000 with 1,739 sqft and a lot size of 0.22. 738 S PENNSYLVANIA AVENUE has 3 bedrooms, 2.0 baths, and was built in 1925. The property's zip code is 32789 which is in Winter Park, FL