Engelwood Park vs Winter Park Pines
Two Orange communities, compared on the numbers that decide it — price, pace, and supply — from live MLS data as of 2026-10-12.
| Metric | Engelwood Park | Winter Park Pines |
|---|---|---|
| Median sale price | $331K | $610K |
| Price per sq ft | $262 | $327 |
| Avg days on market | 176 days | 68 days |
| Months of supply | 0.9 mo | 3.4 mo |
| Market | Seller's Market | Balanced Market |
| 1-year price change | False | False |
| Recent closings | 39 | 32 |
The verdict
Winter Park Pines carries the higher median price — about 84% above Engelwood Park. Homes in Winter Park Pines sell faster (68 days on market vs 176). Engelwood Park is the tighter market on inventory (0.9 months of supply).
Where each one is
Engelwood Park and Winter Park Pines are about 4 miles apart (straight-line, center to center) and share Orange County.
| Engelwood Park | Winter Park Pines | |
|---|---|---|
| County | Orange County, FL | Orange County, FL |
| City / area | Orlando | Winter Park |
| ZIP | 32807 | 32792 |
| FEMA flood zones (sampled parcels) | all 15 sampled homes outside a flood zone | all 20 sampled homes outside a flood zone |
Distances are straight-line; driving distance is usually 15 to 30 percent more. Flood-zone shares come from FEMA flood maps matched to sampled parcels; always check the exact address before you close.
What is for sale today
| Engelwood Park | Winter Park Pines | |
|---|---|---|
| Homes for sale now | 3 | 9 |
| Under contract | 3 | 3 |
| Asking prices today | $320K to $365K | $495K to $798K |
| Property types listed | Single Family Residence | Single Family Residence |
Live MLS counts, refreshed with every listing pull. Browse them: Engelwood Park homes for sale · Winter Park Pines homes for sale.
The homes themselves
| Engelwood Park | Winter Park Pines | |
|---|---|---|
| Homes (parcels) | 418 | 289 |
| Built | 1952–1983 (median 1958) | 1960–2007 (median 1965) |
| Typical living area | 1,272 sq ft | 1,813 sq ft |
| Homesteaded (owner-occupied) share | 65% | 79% |
Housing-stock figures from the Florida Department of Revenue 2025 assessment roll (public records).
Price history, year by year
| Year | Engelwood Park median | Winter Park Pines median |
|---|---|---|
| 2012 | $72K (21 sales) | $164K (17 sales) |
| 2013 | $94K (23 sales) | $255K (10 sales) |
| 2014 | $108K (40 sales) | $262K (28 sales) |
| 2015 | $116K (34 sales) | $254K (42 sales) |
| 2016 | $136K (46 sales) | $299K (28 sales) |
| 2017 | $168K (48 sales) | $335K (36 sales) |
| 2018 | $170K (10 sales) | $337K (12 sales) |
| 2019 | $205K (5 sales) | $363K (10 sales) |
| 2021 | $264K (4 sales) | $420K (8 sales) |
| 2022 | $289K (47 sales) | $492K (44 sales) |
| 2023 | $310K (13 sales) | $515K (12 sales) |
| 2024 | $347K (36 sales) | $580K (24 sales) |
| 2025 | $330K (32 sales) | $530K (29 sales) |
| 2026 | $340K (35 sales) | $600K (23 sales) |
Since 2012, Engelwood Park's median sale price is +372% and Winter Park Pines's is +265% — Engelwood Park has appreciated faster over that stretch.
How each one trades
| Engelwood Park | Winter Park Pines | |
|---|---|---|
| Sale-to-original-list | 97.4% | 97.6% |
| New-construction share of sales | 0% | 0% |
| Typical sold home | 1,267 sq ft | 1,829 sq ft |
| Momentum market-heat score | 41 (normal) | 63 (hot) |
Last 12 months of recorded closings; sale-to-original-list is the share of the first asking price sellers actually got.
Schools the listings are zoned for
| Engelwood Park | Winter Park Pines | |
|---|---|---|
| Elementary | Engelwood Elementary | Aloma Elem |
| Middle | Roberto Clemente Middle | Glenridge Middle |
| High school | Colonial High | Winter Park High |
The school most often recorded on each community's MLS listings. Always confirm a specific address with the district.
Which one fits
On budget alone, Engelwood Park is the lower entry point (median $331K vs $610K). Buyers who want newer construction (fewer near-term roof, HVAC and re-plumb items, and easier insurance quotes in Florida) will find it in Winter Park Pines; Engelwood Park trades that for a more established street and, typically, larger lots. Sellers get a faster sale in Winter Park Pines (68 days on market on average); buyers get more negotiating room where homes sit longer.
Neither number set decides it: drive both on a weekday evening, check the HOA documents and the flood zone for the exact street, and price the insurance before you write an offer. A Momentum agent who works both communities can pull the comparable sales for any two specific homes.
Questions people ask
Is Winter Park Pines more expensive than Engelwood Park?
Yes, on recent sales: the median sale price in Winter Park Pines is $610,000 versus $331,000 in Engelwood Park, about 84% higher.
How far apart are Engelwood Park and Winter Park Pines?
About 4 miles straight-line, center to center, both in Orange County; driving distance is usually 15 to 30 percent more.
Which has newer homes, Engelwood Park or Winter Park Pines?
Winter Park Pines: its homes were built 1960–2007 with a median year of 1965, versus a median of 1958 in Engelwood Park (Florida DOR assessment roll).
Which has bigger homes?
Winter Park Pines. The typical home there is 1,813 sq ft of living area, versus 1,272 sq ft in Engelwood Park.
Which has appreciated more, Engelwood Park or Winter Park Pines?
From 2012 to 2026 the median sale price rose 372% in Engelwood Park and 265% in Winter Park Pines (recorded MLS closings by calendar year).
What high schools serve Engelwood Park and Winter Park Pines?
Listings in Engelwood Park most often report Colonial High; listings in Winter Park Pines report Winter Park High. Zoning is set by the district and can change - verify by address.
Go deeper on each: Engelwood Park homes, photos & schools · Winter Park Pines homes, photos & schools
Figures are aggregates from realMLS / DBAAR, updated regularly. Thinking about either? Talk to Momentum Realty.