Winter Park Town
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.
Photo via Stellar MLS
As of September 2026, the MLS records 7 closed sales in Winter Park Town Of in Winter Park, FL since 2007, the most recent in March 2024. 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).
Winter Park Town spans construction from 1915 through 2024, with a median build year of 1972 — a mix that puts early-to-mid-century houses alongside newer infill on the same streets. That range is the core pricing variable: condition, updates, and lot handling separate one listing from the next more than location does, since the footprint here is small and consistent.
With 452 homes in the dataset and a homestead share of 59.3%, turnover is moderate and a meaningful share of owners have settled in for the longer term. No community amenities are identified from current MLS listings, so buyers are paying for the house and its lot, not a package of shared recreation — worth confirming directly if that matters to a purchase decision.
Nearby homes for sale
No active listings inside Winter Park Town Of 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
A historic Winter Park pocket where a median living area of 1,706 square feet reflects an older, walkable housing stock rather than newer large-format construction, and where the age spread from 1915 to 2024 means every listing needs to be evaluated on its own condition and updates.
Stellar MLS sales records identify 12 homes in Winter Park Town that have changed hands since 2004, built between 1924 and 2020 (median 1952), with a median living area of about 1,241 sq ft and a typical 3-bedroom, 2-bath layout; 83% 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 Winter Park Town is best for.
Best for
- Buyers who want an established Winter Park location and are comfortable evaluating homes built across a wide range of years, from 1915 to 2024
- Buyers focused on a compact, walkable floor plan near the community's median living area rather than maximum square footage
- Buyers planning to budget for condition-based renovation work rather than expecting turnkey uniformity
Probably not for
- Buyers who want a managed community with organized shared amenities, since none are identified here
- Buyers who need a larger floor plan well above the 1,706 sq ft median as a baseline expectation
- Buyers unwilling to commission a full inspection given how much construction age varies across the community
The market around Winter Park Town
Winter Park Town 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 Winter Park Town specifically. Momentum Research analysis of MLS records.
The Winter Park Town buying strategy.
If we were buying in Winter Park Town 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 Winter Park Town.
Reading the age spread
The single most useful number in this dataset is the year-built range: 1915 to 2024. A market with that spread does not price uniformly — a home built in 1972, the community median, sits in the middle of a continuum that includes both century-old construction and recent builds. Expect systems, roofs, and finishes to vary widely from one address to the next, which is why a walkthrough matters more here than in a subdivision built in a single phase.
At 1,706 square feet median living area, this is not a large-format market. Buyers comparing square footage against other Winter Park or Orange County communities should treat that number as a baseline for older, more compact floor plans rather than an indicator of what is achievable on a given lot. With no listed community amenities, the appeal is the house and the location itself, not a shared clubhouse or recreation package.
The location and the amenities are priced into every listing in Winter Park Town. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a community with this much construction-year variance, we walk every listing with an eye toward what the age of the structure actually means for near-term costs — roof, HVAC, electrical — rather than relying on square footage or a listing photo. That diligence matters more here than in a newer-build community, and it is where we spend our time on a buyer's behalf.
Winter Park Town in 15 seconds.
HOA, CDD & Fees
- HOA status not on record. Verify any dues before you offer
- Any club/amenity membership is billed separately
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 Winter Park Town 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 Winter Park Town sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Winter Park Town, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Winter Park Town home worth?
Get a no-obligation home value based on real comparable sales in Winter Park Town, not an automated guess. Tell us about your home and we will personally prepare your numbers and a pricing strategy. No obligation, no spam.
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Should you buy in Winter Park Town?
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 14, 2026) |
| Under-contract shares | Stellar MLS records, as of 2026-09-08 |
| Historical depth | Closed-sale records back to 2007 (7 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.
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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.
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See how Winter Park Town fits the bigger picture — live prices, inventory, and Momentum Scores:
Common questions about Winter Park Town
Where is Winter Park Town?
Winter Park Town is a community in Winter Park, Orange County, Florida, ZIP 32789.
Are there homes for sale in Winter Park Town right now?
No active listings inside Winter Park Town at the last feed refresh. The nearest homes for sale, with distances from the community, are shown on this page and refreshed nightly.
Does Winter Park Town have an HOA or CDD?
No HOA is on record for Winter Park Town 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 Winter Park Town with Momentum Realty’s local guides.
Winter Park Town Of Market Scorecard
Winter Park Town Of 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: realMLS, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.