Date
Details
Price
Change
Source
1/21/2026
Listed
$2,650
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
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$2,650
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Property Description
Historic 2-bedroom home walking distance to Park Avenue and Rollins College. This well-maintained rental features a living room fireplace, fresh interior paint, and new cordless blinds throughout. The kitchen includes stainless steel appliances and a gas stove. Enjoy a screened front porch, fully fenced yard, and ample rear parking. Prime Winter Park location with classic charm and modern updates.
Full Property Details
Full Property Details for 865 S Pennsylvania Ave
General
- Rent: $2,650
- Status: Active
- Type: Single Family
- Source: MidFloridaRegionalMLS
- MLS ID: O6375024
- Updated: 2/27/2026
- Added to Site: 37 day(s) ago
Rental Information
- Lease/Rent Term: 12 Months
- Min. Lease: No Minimum
Interior
- Number of Rooms: 2
- Interior Features: Ceiling Fan(s)
- Fireplace: Yes
- Fireplace(s): Living Room
- Appliances: Built-In Oven, Cooktop, Dishwasher, Disposal, Dryer, Electric Water Heater, Exhaust Fan, Freezer, Microwave, Refrigerator, Washer, Water Filtration System
- Furnishings: Unfurnished
Rooms
Bathrooms
- Total Bathrooms: 1
- Full Bathrooms: 1
Bedrooms
- Total Bedrooms: 2
Other Rooms
- Laundry: In Kitchen
Exterior
- Deck/Patio: Enclosed, Front Porch, Screened
- Porch/Patio/Deck: Enclosed, Front Porch, Screened
Location
- Area: 32789 - Winter Park
- County: Orange
- Development Name: 32789 - Winter Park
- Subdivision: WINTER PARK
- Driving Directions: From Fairbanks Ave, turn right onto S Pennsylvania Ave, house is on the right, directly across from the Winter Park 9th Grade Center
Community
- Community Name: 32789 - Winter Park
Heating & Cooling
- Cooling Type: Central Air
- Heating Type: Central, Electric, Natural Gas
Structural Information
- Stories/Levels: One
- Square Feet: 1,000
- Sq. Ft. Source: Owner
- Year Built: 1925
Lot Features
- Lot Size (Acres): 0.17
- Lot Size (Sq. Ft.): 7,350
- Lot Size: 7350
- Street/Road Desc.: Concrete, Dirt, Gravel
- Fencing (Description): Fenced
Financial Considerations
- Lease Price: $2,650
- Application Fee: $50
- Security Deposit: $2,650
- Pet Deposit: $500
Disclosures and Reports
- APN: 52230940099050
- Property ID: 52230940099050
Listed by Sandroni Holdings Real Estate Llc
Schools
Schools serving 865 S Pennsylvania Ave
School District:Orange County School District
| Name | Grades | Distance |
|---|---|---|
Audubon Park School 1500 Falcon Drive, Orlando, FL 32803 | PK-8 | 1.7 mi |
Winter Park High School 2100 Summerfield Road, Winter Park, FL 32792 | 9-12 | 2.1 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price History for 865 S Pennsylvania Ave
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- Single Family
- Active
- 2Beds
- 1Total Bath
- 566Sq. Ft.
Listed by Lpt Realty, Llc
- Single Family
- Active
- 2Beds
- 1Total Bath
- 1,163Sq. Ft.
Listed by Fre Associates Llc
- Single Family
- Active
- Updated 3 days ago
- 2Beds
- 1Total Bath
- 911Sq. Ft.
Listed by A+ Realty Professionals, Inc
- Single Family
- Active
- 2Beds
- 1Total Bath
- 962Sq. Ft.
Listed by Mainframe Real Estate
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![[Address not provided], Maitland, FL 32751 - Photo 1](https://m1.cbhomes.com/p/646/R4910749/A35Aa53F14b64EF/s23cc.webp)
- Single Family
- Active
- Updated 2 days ago
- 3Beds
- 2Total Baths
- 1,500Sq. Ft.
Listed by L.G. Simmonds Real Estate
- Condo
- Active
- Updated 1 hour ago
- 2Beds
- 1Total Bath
- 1,051Sq. Ft.
Listed by Mila Realty
- Condo
- Active
- Updated 1 day ago
- 1Bed
- 1Total Bath
- 612Sq. Ft.
Listed by Metro City Realty
- Single Family
- Active
- Updated 1 day ago
- 3Beds
- 3Total Baths
- 1,510Sq. Ft.
Listed by United Real Estate Preferred
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- Single Family
- Active
- Updated 2 days ago
- 1Bed
- 1Total Bath
- 759Sq. Ft.
Listed by Specialized Property Management
- Condo
- Active
- Updated 4 days ago
- 1Bed
- 1Total Bath
- 550Sq. Ft.
Listed by Cani Property Management
- Condo
- Active
- Updated 4 days ago
- 2Beds
- 2Total Baths
- 1,106Sq. Ft.
Listed by Top Orlando Realty
- Apartment
- Active
- Updated 1 day ago
- 2Beds
- 2Total Baths
- 1,080Sq. Ft.
Listed by The Apartment Brothers Llc
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- Condo
- Closed
- 2Beds
- 2Total Baths
- 1,216Sq. Ft.
Listed by Keller Williams Winter Park
Sold by Keller Williams Realty At The Parks
Sold by Keller Williams Realty At The Parks
- Single Family
- Closed
- 2Beds
- 2Total Baths
- 1,127Sq. Ft.
Listed and Sold by Lippi Realty Llc
- Townhouse
- Closed
- 2Beds
- 3Total Baths
- 1,641Sq. Ft.
Listed and Sold by Banner Int'l Real Estate
- Townhouse
- Closed
- 3Beds
- 3Total Baths
- 1,852Sq. Ft.
Listed and Sold by Hpl Realty Investments
865 S Pennsylvania Avenue, Winter Park, FL 32789 (MLS# O6375024) is a Single Family property with 2 bedrooms and 1 full bathroom. 865 S Pennsylvania Avenue is currently listed for rent at $2,650 and was received on January 21, 2026. Want to learn more about 865 S Pennsylvania Avenue? Do you have questions about finding other real estate for sale or rent in Winter Park? You can browse all Winter Park rentals or contact a Coldwell Banker agent to request more information.