Search

Nearby Properties

738 S PENNSYLVANIA AVE,  WINTER PARK, FL 32789

MLS# S5151458.  3 beds.  2.0 baths.  Single Family Home.  Active

$2,730 in taxes (2025)

$735,000

 

Remarks:

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.

Quick Info:

  • Listing is courtesy Of: COMPASS FLORIDA LLC ((407-203-9441))
  • Listing Agent: Justin Jodha ((689-250-8606))
  • Days on yellowkey: 5
  • Property Type: Single Family Home
  • Beds: 3
  • Baths: 2.0
  • Living Area Square Feet: 1739
  • Built 1925
  • Taxes: $2,730 (2025)
  • 0 Days off yellowkey (back on 6/10/2026 )
  • Garage Spaces:1 ()
  • Square Feet: 2099
  • Fees: $0
  • Orange County
  • Terms: Cash, Conventional, FHA, VA Loan
  • Subdivision Info:
  • Occupancy Information: Vacant
  • Community:
  • Membership Purchase Required:
  • Development Name:
  • Subdivision Name: WINTER PARK
  • Complex Name:

Interior Details:

  • Interior Levels:
  • Stories:
  • Bedroom Description:
  • Master Bathroom Description:
  • Interior Features: Ceiling Fans(s), Walk-In Closet(s)
  • Dining Description:
  • Floor:
  • Cooling:
  • Heating:
  • Equipment/Appliances:
  • Other Rooms:
  • Windows Treatment:
  • Cable Available
  • Water Utility:

Exterior/Other Details:

  • Design:
  • Design Description:
  • Guest House Living Area:
  • Guest House Description:
  • Efficiency:
  • Unit Floor Location:
  • Guest House Description:
  • Garage Description:
  • Carport Spaces:
  • Carport Description:
  • Parking Description:
  • Pool Description:
  • Pool Dimensions:
  • Lot:
  • Front Exposure:
  • Exterior Features:
  • Roof Description:
  • Security:
  • Sprinkler:
  • Sewer Description:
  • Miscellaneous:
  • View:
  • Waterfront Front:
  • Waterfront Description:
  • Water Access:

History:

DateListing TypeDays on yellowkeyMLS#EventPrice% Chg$/sqftSource
6/10/2026Sale1S5151458Back on yellowkey$735,000-350.1667MLS
6/8/2026Sale0S5151458listed for sale$735,000-350.1667MLS




Data is updated at least once a week by Sunday nights. Some properties that appear for sale on this web site may subsequently have been sold and may no longer be available. The data relating to real estate for sale/lease on this web site come in part from a cooperative data exchange program of the multiple listing service (MLS) in which this real estate firm (Broker) participates. Data can be retrieved from any one of the following MLS’s: Greater Fort Lauderdale REALTORS®, Space Coast Association of REALTORS®, My Florida Regional MLS, Florida Gulf Coast MLS, "©2024 Northeast Florida Multiple Listing Service, Inc. All rights reserved." The properties displayed may not be all of the properties in the MLS’s database, or all of the properties listed with Brokers participating in the cooperative data exchange program. Properties listed by Brokers other than this Broker are marked with either the listing Broker’s logo or name or the MLS name or a logo provided by the MLS. Detailed information about such properties includes the name of the listing Brokers. Information provided is thought to be reliable but is not guaranteed to be accurate; you are advised to verify facts that are important to you. No warranties, expressed or implied, are provided for the data herein, or for their use or interpretation by the user. The Florida Association of Realtors® and its cooperating MLSs do not create, control or review the property data displayed herein and take no responsibility for the content of such records. Federal law prohibits discrimination on the basis of race, color, religion, sex, handicap, familial status or national origin in the sale, rental or financing of housing.