Pennsylvania Place
Homes for Sale in Winter Park, FL
All 394 homes for sale in Winter Park, FL · median $636,250 · 169 homes for sale in 32789 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of November 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, 887 homes closed in the last 12 months at a median of $499,000, 37 median days on market, with 326 homes for sale today. At that median and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $8,320 ($7,650 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.
Figures in this note are as of July 21, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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.
County records show 17 qualified sales in Pennsylvania Place across 2024 - 2025 (12 in 2024, 5 in 2025), median $792,500 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
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, 239 homes are on the market and 23% are under contract — a steady corner of Winter Park.
Across Orange County, 5,774 homes are active and 1,755 pending (23% under contract).
In ZIP 32789 (Winter Park), 111 homes closed in the last 12 months at a median of $627K ($396/sq ft), down 21.6% year over year, with a median 42 days on market. Right now 34 active and 4 pending listings put supply at about 3.7 months - a buyer's 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.
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 →
Recently off market in Pennsylvania Place Rep
Homes in Pennsylvania Place Rep that recently left the market. Each address opens its public-record profile: county-recorded value, property taxes, the last recorded sale, community sales history, and what is for sale nearby now. 1 on record.
- 622 Penn Place · off market
| Location | Winter Park, Orange County, FL · ZIP 32789 |
|---|---|
| Homes in the community | 134 (FL DOR 2025 assessment roll) |
| Years built | 1918–2021 (median 1999) |
| Typical living area | 2,325 sq ft (median) |
| Amenities listed by sellers | Park |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 57% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2012 through 2025; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Pennsylvania Place key facts,” movewithmomentum.com/neighborhoods/pennsylvania-place-rep-winter-park, data as of September 20, 2026.
Housing distress & ownership in Pennsylvania Place Rep, Winter Park
Who owns here, how much is not owner-occupied, and how much for-sale inventory is under distress.
Source: Momentum Realty Research. Ownership & parcels from the FL DOR 2025 tax roll; distress from MLS active-listing status/remarks; price from MLS closed sales. Based on Stellar MLS data distributed by MLS GRID for the period November 2026 through November 2026. Deemed reliable but not guaranteed.
More Winter Park home searches
- All homes for sale in Winter Park, FL
- Homes for sale in Orange County, FL
- Gated communities in Winter Park
- Homes under $300K in Winter Park
- 4-bedroom homes for sale in Winter Park
- Winter Park home values: what is my house worth?
- ZIP 32789 housing scorecard
Winter Park guides & data
- Market data
- Cost of living
- Best neighborhoods
- Flood zones
- Property taxes (Orange County)
- Homestead exemption (Orange County)
- Home insurance cost
- New construction
Florida buyer guides
- Florida home insurance rates by county
- Florida property tax by county
- Florida property tax calculator
- What flood zone X means
- The 4-point inspection, explained
- Florida flood insurance calculator
- Florida housing market map
- Interactive housing market map (county, ZIP and community)
- Save Our Homes tax estimator
- How to stop a foreclosure in Florida
- Florida documentary stamp tax, explained
- Cheapest places to live in Florida
Real estate agent in Winter Park? Join Momentum in Winter Park: 100% commission, one $12K cap.
Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- N Pennsylvania Avenue (2 homes on record)
- N Pennsylvania Avenue (2 homes on record)
Email me new listings in Pennsylvania Place
One e-mail a day, only when a home lists here, with price, beds, baths and a link to every listing. Straight from the MLS feed; no account needed.
Ask an agent about Pennsylvania Place
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Pennsylvania Place will answer, and the answer is published on this page for the next buyer.
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.
Frequently Asked Questions
How many homes are in Pennsylvania Place?
What share of Pennsylvania Place is owner-occupied?
When were the homes in Pennsylvania Place built?
Who is the best real estate agent for Pennsylvania Place?
How do I find a top Winter Park real estate agent who knows Pennsylvania Place?
Can Momentum Realty connect me with an agent for Pennsylvania Place?
Where is Pennsylvania Place, and what county is it in?
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 16, 2026) |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (2 streets, ZIP 32789)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| 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. A Momentum agent can price yours against live local comps.
Looking to buy here? Search homes for sale →
What’s your home worth in your area?
A real valuation with real comps from a local listing agent, not an instant algorithm. Response within one business day.
See how Pennsylvania Place Rep fits the bigger picture — live prices, inventory, and Momentum Scores: