1021 Pennsylvania Avenue, FL1021 Pennsylvania Avenue, FL1021 Pennsylvania Avenue, FL
Stellar MLS
1 / 7

$1,295,000

1021 Pennsylvania Avenue

Winter Park, FL 32789

Listing updated: September 2, 2026 at 8:17 PM ET

Active
Stellar MLSListing courtesy of Premier Sotheby'S Intl. Realty · Mick Night · MLS #O6429124 · Active · 407-644-3295
0
Baths
0.51
Acres
$58/sqft360° tour
Land

Property type

22,198 sqft

Lot size

$58

Price / sq ft

No HOA

HOA dues

0

Days on market

X

Flood zone

About this home

A rare opportunity to build your custom dream home on a cleared homesite spanning more than one-half acre in a prime Winter Park location. Large, buildable parcels of this size are becoming increasingly difficult to find, making this an exceptional offering for those seeking space, flexibility and the freedom to create a truly custom residence. Located along Pennsylvania Avenue, this expansive homesite is ready for construction, with no HOA, allowing you to bring your own builder and vision to life (Building: 35% FAR apprx 7,800sf + excluded porches SF - all calculations to be confirmed with your architect & City of WP Building Dept). The generous dimensions easily accommodate a substantial residence with room for a resort-style pool, expansive outdoor living areas, guest house or other amenities, creating endless possibilities. Enjoy an exceptional lifestyle just minutes from many of Winter Park's most popular destinations. Walk, bike or take a golf cart ride to the historic Winter Park 9 Golf Course, the boutiques, award-winning restaurants and sidewalk cafés of Park Avenue, the vibrant dining scene of Hannibal Square, Winter Park Village, Mead Botanical Garden and numerous parks, cultural attractions and community events. This central location also offers convenient access to Rollins College, Valencia College, highly regarded public and private schools, downtown Orlando, major hospitals, Orlando Executive Airport, Orlando International Airport and Central Florida's major roadways. Whether your vision is a timeless estate, a contemporary architectural masterpiece or a private retreat with exceptional outdoor living, this oversized homesite provides the rare canvas to bring it to life. Opportunities to purchase a cleared, build-ready parcel of more than one-half acre in Winter Park are few and far between—making this an outstanding opportunity to create a one-of-a-kind residence in one of Central Florida's most established communities.

Estimated monthly payment

Principal & interest$6,548
Property taxes$451
Home insurance (est.)$594

Estimate only. Taxes use the listing's reported amount where available; insurance is a Florida-average estimate. Your actual payment will vary — run a full calculation or talk to a lender.

Price & listing history0 days on market

  1. Status: Active
    Sep 2, 2026
  2. Listed$1,295,000
    Sep 2, 2026
  3. Price increased$1,295,000

Facts & features

Property type
Land
Status
Active
Days on market
0
Subdivision
Winter Park Oasis
County
Orange
Price/sq ft
$58
Lot size
22,198 sq ft
Lot category
1/2 to less than 1
Flood zone
X (12095C0255F)
Annual taxes
$5,407 (2025)
Parcel #
06-22-30-9662-00-190
Zoning
R-1A
MLS #
O6429124

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Interior Details

Direction faces
East

HOA & Financial

Total monthly fees
$0/mo
Total annual fees
$0
CDD
No
Ownership
Fee Simple

Exterior & Construction

Road surface
Paved

Utilities

Sewer
Public Sewer
Water source
Public
Utilities
BB/HS Internet Available, Cable Available, Sewer Available, Water Available

Community

Pets allowed
Yes

Schools

ElementaryBLakemont ElemGreatSchools ↗
MiddleBMaitland MiddleGreatSchools ↗
High SchoolAWinter Park HighGreatSchools ↗

Letter grades: Florida DOE 2024–25 school grades (Orange, Seminole, Lake, Osceola, Brevard). Assigned schools from the listing agent — verify enrollment with the district.

Listing Details

Listing date
2026-08-03
On market date
2026-09-02
Original list price
$1,295,000
MLS area
32789 - Winter Park
Listing AOR
Orlando Regional
Status changed
2026-09-02
Tax legal description
WINTER PARK OASIS Z/135 LOTS 19 & 20

Flood risk

Minimal riskFEMA Zone XPanel 12095C0255F

Minimal-risk area outside the mapped floodplain. Flood insurance is optional and typically low-cost.

Source: FEMA flood zone reported on the listing. Confirm current designation at FEMA Flood Map Service Center.

Location

Directions

From N Park Avenue and N Pennsylvania Ave, travel south on N Pennsylvania Ave. Property will be on the right.

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MLS GRID

Listings courtesy of Stellar MLS as distributed by MLS GRID

IDX information is provided exclusively for consumers’ personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Based on information submitted to the MLS GRID as of September 2, 2026 at 8:17 PM ET. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.

All or a portion of the multiple listing information is provided by Stellar MLS, from a copyrighted compilation of listings. The compilation of listings and each individual listing are © 2026 Stellar MLS. All rights reserved.

Ryan Solberg, Broker · MaxLife Realty LLC · FL License #BK3354351 · Equal Housing Opportunity · Full disclaimer · DMCA