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Active · Condo

500 PENNSYLVANIA AVENUE

WINTER PARK, FL 32789

Beds
2 beds
Baths
1 bath
Area
709 sqft
CondoBuilt 19813,902 sqft lotCentral, ElectricCentral Air$493/sqft1 day on market

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
Estimated monthly payment$2,514/mo
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.

2122 RIDGE DRIVEActive
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2122 RIDGE DRIVE
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7506 CRANES CREEK COURTActive
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7506 CRANES CREEK COURT, 30
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1484 VIBURNUM LANEActive
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3 beds2 baths1,363 sqft

Price history

From the property’s MLS record.

DateEventPriceChange
Sep 3, 2026Listed$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.

Elementary school
Not listed
Not named in the MLS record for this home
Middle school
Not listed
Not named in the MLS record for this home
High school
Not listed
Not named in the MLS record for this home