Pennsylvania Place
Homes for Sale in Winter Park, FL
All 337 homes for sale in WINTER PARK, FL · median $664,900 · 150 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of September 2026, the MLS records 10 closed sales in Pennsylvania Place Rep in Winter Park, FL since 2012, the most recent in August 2025. Across Winter Park as a whole, 494 homes closed in the last 12 months at a median of $459,450, 34 median days on market, with 124 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $7,660 ($6,990 with the full homestead exemption).
Pennsylvania Place's pricing story is really a condition-and-vintage story. With homes built anywhere from 1918 to 2021 and a median build year of 1999, buyers are choosing between early-century character and homes built closer to the turn of the millennium, and that spread does more to set value than any single market metric.
With just one active listing against 134 homes in the community, current supply is thin, and the 12-month supply figure signals a market that currently favors buyers who are patient enough to wait for the right listing rather than one where multiple options are competing for attention at once.
Nearby homes for sale
No active listings inside Pennsylvania Place Rep right now. These are the 6 closest homes on the market, by straight-line distance from the community's center; some may sit just outside its boundary.
Listing data from the MLS feeds named on each listing page; deemed reliable but not guaranteed. Refreshed nightly.
The 60-Second Overview
Pennsylvania Place sits in Winter Park within Orange County, pairing a long build history with a median living area of 2,325 square feet and a majority-homestead base of owners, both signs of a community built for longer-term occupancy rather than rapid turnover.
Stellar MLS sales records identify 21 homes in Pennsylvania Place that have changed hands since 2005, built between 1999 and 2007 (median 2002), with a median living area of about 3,356 sq ft and a typical 4-bedroom, 3.5-bath layout; 100% are single-family homes. Source: Stellar MLS closed-sale history compiled by Momentum Research; counts reflect homes with a recorded MLS sale, not every home in the community.
Pre-construction details are compiled from public records, builder announcements and builder listings, and are subject to change without notice; figures are deemed reliable but not guaranteed. Momentum Research figures are our own analysis. This page describes homes, pricing and community attributes, not residents.
Who Pennsylvania Place is best for.
Best for
- Buyers targeting a specific Winter Park location who are willing to wait for the right listing to surface
- Buyers comfortable evaluating a home individually given the wide build-year range rather than expecting a uniform product
- Buyers who value deed-restricted structure and park access as part of the community setup
Probably not for
- Buyers who want several active listings to compare before making a decision
- Buyers seeking a quick close in a high-inventory, fast-turnover market
- Buyers who prefer a single, consistent build era rather than a mix spanning over a century
The market around Pennsylvania Place
Pennsylvania Place is too small for its own price trend, so here is the market around it.
In ZIP 32789, 244 homes are on the market and 25% are under contract — a steady corner of Winter Park.
Across Orange County, 5,909 homes are active and 1,877 pending (24% under contract).
In ZIP 32789 (WINTER PARK), 394 homes closed in the last 12 months at a median of $635K ($396/sq ft), up 7.4% year over year, with a median 40 days on market. Right now 88 active and 21 pending listings put supply at about 4.9 months - a balanced market. See the live ZIP 32789 housing market and the Orange County market.
ZIP and county figures describe the wider market, not Pennsylvania Place specifically. Momentum Research analysis of MLS records.
Life at Pennsylvania Place
- Park · reported on 2 of 2 listings
- Deed Restrictions · reported on 1 of 2 listings
Community amenities as reported across Stellar MLS listings in this community; deemed reliable but not guaranteed. Verify current amenities and access with the HOA.
The Pennsylvania Place buying strategy.
If we were buying in Pennsylvania Place today, this is the order of operations we would run for our clients.
Underwrite the condition first. Price the roof, HVAC, and systems honestly before judging any list price; condition swings value here more than square footage alone.
Match the home to real comps. Recent sales of similar condition and lot, not the asking price, tell you what a home is worth.
Move deliberately, not desperately. Neither side has a decisive edge, so a well-prepared, fairly-priced offer wins without overpaying.
Line up financing and inspection early. A pre-approval and an inspection plan let you act fast and negotiate from evidence.
Keep an agent in your corner. The listing agent works for the seller; we represent you and prepare a hand-built valuation before any offer in Pennsylvania Place.
A century of builds, one listing at a time
The build range here, 1918 to 2021, means Pennsylvania Place isn't a single-era community. A median year built of 1999 puts the typical home at a point where original systems and finishes have likely already seen at least one update cycle, but individual homes closer to either end of that range will vary widely in what condition and mechanicals a buyer can expect.
At 134 total homes and just one active listing, this is a low-volume market where each sale carries more weight than in a larger subdivision. The 12-month supply figure reflects that thinness as much as it reflects demand, so buyers and sellers should read it as a signal of limited inventory rather than a broad market cooling.
The location and the amenities are priced into every listing in Pennsylvania Place. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with only one home currently active out of 134, timing and access matter more than usual. We track listings here closely so buyers are not relying on stale portal data, and we help sellers price against a build range and square footage profile that varies enough to require a genuine comparable analysis rather than a formula.
Pennsylvania Place in 15 seconds.
HOA, CDD & Fees
- HOA dues reported around $222/month (about $2,664/yr) · median of 3 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $222 per month ($2,664 a year) - the median AssociationFee across 3 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-09.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Tools for a Pennsylvania Place buy.
Free calculators to pressure-test the real cost before you tour.
Selling here is won on condition and pricing to real comps, not an automated estimate. The right number comes from closed Pennsylvania Place sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Pennsylvania Place, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Pennsylvania Place home worth?
Get a no-obligation home value based on real comparable sales in Pennsylvania Place, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
See all homes for sale in Winter Park →
Should you buy in Pennsylvania Place?
An honest fit check. We will tell you when it is not your community.
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: September 12, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2012 (10 transactions analyzed) |
Verify the primary sources yourself: Florida DOR · U.S. Census · FEMA flood maps · Citizens Property Insurance.
Momentum Research figures are our own analysis of Stellar MLS records; MLS data is deemed reliable but not guaranteed. Methodology: how Momentum market scores are computed. Market metrics describe homes for sale and recent sales, not residents.
Own a home here?
You just read the data. Now see what your home is worth.
The numbers on this page move markets in the aggregate. The number that matters to you is what a buyer pays for your address. Momentum sells for 1.25% above the Stellar MLS member average and 8 days faster, and we’ll price yours against live local comps.
Looking to buy here? Search homes for sale →
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A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Pennsylvania Place fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Pennsylvania Place
Where is Pennsylvania Place?
Pennsylvania Place is a community in WINTER PARK, Orange County, Florida, ZIP 32789.
Are there homes for sale in Pennsylvania Place right now?
No active listings inside Pennsylvania Place at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Pennsylvania Place have an HOA or CDD?
No HOA is on record for Pennsylvania Place in our data. Verify dues, what they cover, and any special assessment for a specific address before you offer.
Answers are generated from county property records, MLS feeds and the figures on this page, as of the page date; deemed reliable but not guaranteed.
Nearby Communities
Explore more neighborhoods near Pennsylvania Place with Momentum Realty’s local guides.
The real cost & risk here
Before the list price, the Florida math the portals skip. These are Orange County typicals — your exact home, flood zone, and insurance quote will vary, so verify each before you offer.
Check it for your address: look up your flood zone (FEMA) · insurance by county · true-cost calculator · Orange County scorecard.
County typicals from Momentum’s Florida housing data (Zillow & Realtor.com aggregates, Census, FRED), updated monthly; insurance modeled. Flood zone is property-specific — always confirm via FEMA.
PENNSYLVANIA PLACE REP Market Scorecard
PENNSYLVANIA PLACE REP is currently a no active listings market. Limited supply, a median asking price of n/a.
Typical home value in the 32789 ZIP is $809,773, about 61.9% above the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.