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$349,500 Just Listed

  • For Sale
  • Active
  • Condo
  • 2 Beds
  • 1 Full Bath
  • 709 Sq. Ft.
  • Updated 1 day ago
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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!**

Full Property Details for 500 N Pennsylvania Ave #G

General

  • Price: $349,500
  • HOA FEE: $410/month
  • Taxes: $4,045 (2025)
  • Status: Active
  • Type: Condo
  • Source: MidFloridaRegionalMLS
  • MLS ID: G5117377
  • Updated: 9/3/2026
  • Added to Site: 1 day(s) ago

Rental Information

  • Min. Lease: 8-12 Months

Interior

  • Number of Rooms: 5
  • Interior Features: Ceiling Fan(s), Crown Molding, Kitchen and Family Room Combination, Living Room/Dining Room Combo, Open Floorplan, Solid Wood Cabinets, Stone Counters, Thermostat
  • Appliances: Dishwasher, Disposal, Dryer, Electric Water Heater, Microwave, Range, Refrigerator, Washer
  • Furnishings: Unfurnished
  • Flooring: Laminate

Rooms

Bathrooms

  • Total Bathrooms: 1
  • Full Bathrooms: 1

Bedrooms

  • Total Bedrooms: 2

Other Rooms

  • Laundry: Electric Dryer Hookup, Laundry Closet

Additional Information

  • Security/Safety: Smoke Detector(s)

Exterior

  • Exterior Features: Lighting, Sidewalk
  • Deck/Patio: Front Porch
  • Porch/Patio/Deck: Front Porch

Parking

  • Parking Features: Assigned, Guest

Location

  • Area: 32789 - Winter Park
  • County: Orange
  • Development Name: 32789 - Winter Park
  • Subdivision: VILLAGE CONDOS
  • Driving Directions: West on Fairbanks Ave. coming from the direction of I-4, Turn left onto S. Pennsylvania Ave continue on the Avenue until you get to 500 N. Pennsylvania Ave Unit G on the 2nd floor
  • Direction Faces: West

Community

  • Community Name: 32789 - Winter Park
  • Community Features: Sidewalks
  • Association: Yes
  • Assoc. Name: Empire Management
  • Assoc. Fees Include: Insurance, Maintenance Structure, Maintenance Grounds
  • Pet Restrictions: Buyers need to independently confirm pet restrictions haven't changed with the Condominium Owner's Association., / 25lbs.

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Central, Electric

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: BB/HS Internet Available, Cable Connected, Electricity Connected

Structural Information

  • Architectural Info: Cottage
  • Architectural Style: Cottage
  • Exterior Const.: Concrete, Stucco
  • Roof: Shingle
  • Windows: Shutters
  • Stories/Levels: One
  • Square Feet: 709
  • Sq. Ft. Source: Public Records
  • Year Built: 1981

Lot Features

  • Lot Size (Acres): 0.09
  • Lot Size (Sq. Ft.): 3,902
  • Lot Size: 3902
  • Street/Road Desc.: Asphalt

Financial Considerations

  • Association Fee: $410
  • Assoc Fee Freq.: Monthly
  • Assoc Fee Desc.: Required
  • Tax Amount: $4,045.91
  • Tax Year: 2025

Disclosures and Reports

  • Ownership: Condominium
  • Special Conditions: None
  • Legal Description: VILLAGE CONDOMINIUM 8382/3580 UNIT G
  • Flood Zone Info: X
  • APN: 62230889500070
  • Property ID: 62230889500070

Listed by Olympus Executive Realty Inc

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Listing agent

— 500 N Pennsylvania Ave #G —

  • Olympus Executive Realty Inc

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 500 N Pennsylvania Ave #G

School District:Orange County School District
NameGradesDistance
Lakemont Elementary School
901 North Lakemont Avenue, Winter Park, FL 32792
K-51.7 mi
Maitland Middle School
701 North Thistle Lane, Maitland, FL 32751
6-82.4 mi
Winter Park High School
2100 Summerfield Road, Winter Park, FL 32792
9-122.3 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 500 N Pennsylvania Ave #G Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/03/2026
Listed
$349,500
20.52%
MLS
8/27/2024
Sold
$290,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 500 N Pennsylvania Ave #G

Year
Property Taxes
Change
Tax Assessment
Change
2025
$4,046
—
$250,000
-2%
2025
$4,046
14%
$255,000
7%
2024
$3,563
15%
$237,500
22%
2023
$3,093
1%
$195,000
—
2021
$3,076
2%
$195,000
—
2022
$3,013
-2%
$195,000
6%
2021
$3,076
56%
$184,300
21%
2019
$1,967
26%
$152,400
48%
2018
$1,559
13%
$103,000
21%
2017
$1,374
13%
$85,100
18%
2016
$1,211
4%
$72,100
8%
2015
$1,168
3%
$66,877
10%
2014
$1,132
17%
$60,797
10%
2013
$969
—
$55,270
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 500 N Pennsylvania Ave #G

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Olympus Executive Realty Inc

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500 N Pennsylvania Avenue #G, Winter Park, FL 32789 (MLS# G5117377) is a Condo property with 2 bedrooms and 1 full bathroom. 500 N Pennsylvania Avenue #G is currently listed for $349,500 and was received on September 03, 2026. Want to learn more about 500 N Pennsylvania Avenue #G? Do you have questions about finding other Condo real estate for sale in Winter Park? You can browse all Winter Park real estate or contact a Coldwell Banker agent to request more information.

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