500 PENNSYLVANIA AVENUE
WINTER PARK, FL 32789
Location
About this home
Virtually Staged. **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**
Facts & features
Interior
- Bedrooms
- 2
- Bathrooms
- 1
- Living area
- 709 sqft
- Heating
- Central, Electric
- Cooling
- Central Air
- Flooring
- Laminate
- Stories
- 2
- Features
- Ceiling Fans(s), Crown Molding, Kitchen/Family Room Combo, Living Room/Dining Room Combo, Open Floorplan, Solid Wood Cabinets…
- Appliances
- Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range…
Exterior & lot
- Lot size
- 3,902 sqft (0.09 ac)
- Roof
- Shingle
- Construction
- Concrete, Stucco
- Exterior
- Lighting, Sidewalk
Financial
- HOA dues
- $410 / monthly
- Annual tax
- $4,046 (2025)
- Price / sqft
- $493/sqft
Utilities
- Water
- Public
- Sewer
- Public Sewer
- Utilities
- BB/HS Internet Available, Cable Connected, Electricity Connected
Property
- Property type
- Condo
- Year built
- 1981
- Subdivision
- VILLAGE CONDOS
- County
- Orange
Listing
- Status
- Active
- Days on market
- 1 day
- MLS #
- MFR804694580
- Source
- Stellar MLS
Listed by Jen Gotlewski · OLYMPUS EXECUTIVE REALTY INC
Listing data provided by Stellar MLS. Information deemed reliable but not guaranteed.
Estimate your monthly cost
PITI + HOA- Principal & interest
- $1,767/mo
- Property tax
- $337/mo
- Home insurance
- Left out until you enter a quote
- HOA dues
- $410/mo
Opens at 20% down over 30 years at 6.5%, the same assumptions as the answers below. Property tax is this listing's own 2025 bill. Insurance is left out until you enter a quote, because Florida premiums turn on roof age, elevation and carrier. Every field is editable.
Ask about this property
Answered from this listing’s own figures and the sales around it.
Similar homes nearby
Homes for sale in WINTER PARK within the same price band.
Price history
From the property’s MLS record.
| Date | Event | Price | Change |
|---|---|---|---|
| Sep 3, 2026 | Listed | $349,500 | — |
Neighbourhood
The schools below come from the MLS record for this home. Walking, transit and cycling figures for WINTER PARK, FL are not connected yet, so this page does not show them.
