Pleasant Park
Homes for Sale in Winter Garden, FL
All 701 homes for sale in Winter Garden, FL · median $585,000 · 645 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
Photo via Stellar MLS
Over the 12 months ending 2026-09-20, 3 recorded sales closed at a median of $550,000, $393 per square foot, a median 154 days on market, sellers accepting 89% of original asking. Homes listed or recently sold were built 1928–2006; none of the 3 geocoded homes sit in a FEMA special flood hazard zone (median elevation 122 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,170 ($8,500 with the full homestead exemption).
Sections of Pleasant Park in the MLS
Pleasant Park in Winter Garden, FL is recorded as 2 separate subdivisions/phases in the MLS; 1 home is for sale across them today. Each section has its own page:
- Rep Pt Pleasant Park Sub · 1 for sale
- Replat Pt Pleasant Park Sub
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 350 (FL DOR 2025 assessment roll) |
| Years built | 1909–2024 (median 1954) |
| Typical living area | 1,530 sq ft (median) |
| Amenities listed by sellers | Golf Carts OK |
| Sale prices, last 12 months | $550,000 median across 3 closed sales · $393 per sq ft |
| Days on market (closed sales) | 154 median |
| For sale right now | 0 active, 0 pending |
| Owner-occupied (homestead) share | 55% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Pleasant Park key facts,” movewithmomentum.com/neighborhoods/pleasant-park, data as of September 20, 2026.
Price here is driven by condition and lot, not by a uniform product. With a median year built of 1955 and a range that runs from 1909 all the way to 2024, Pleasant Park is a genuine mix of older homes, updated older homes, and newer infill. That spread is why two homes on the same street can be worlds apart on price. The median living area of roughly 1,500 square feet tells you this is a smaller-footprint market by today's standards, so square footage and any thoughtful expansion carry real weight.
For a buyer, the work is in the walk-through: you are pricing renovation status, not just an address. For a seller, condition is your lever — an updated home reads very differently here than a tired one of the same vintage. With only a couple of closings in the recent window, comps are thin, so pricing leans on interpretation rather than a fat stack of recent sales. That cuts both ways and rewards a careful hand on both sides.
Nearby homes for sale
No active listings inside Pleasant ParkHomes for Sale in Winter Garden, FL 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
Pleasant Park market snapshot (as of September 20, 2026): the median sale price is about $550K ($393 per sq ft over the trailing 12 months of closed sales), and a median 154 days on market for closed sales.
In ZIP 34787 (Winter Garden), 2,147 homes closed in the last 12 months at a median of $598K ($252/sq ft), down 0.8% year over year, with a median 36 days on market. Right now 352 active and 181 pending listings put supply at about 3.7 months — a balanced market. See the live ZIP 34787 housing market and the Orange County market.
County records show 29 qualified sales in Pleasant Park across 2024–2025 (15 in 2024, 14 in 2025), median $550,000 — the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Pleasant Park is a community of 350 homes in Winter Garden, Orange County, built between 1909 and 2024 (median 1954), with a median living area of about 1,530 square feet. 55% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
Pleasant Park is a 392-home pocket of Winter Garden where the housing stock spans more than a century, so it lives less like a subdivision and more like an established, evolving neighborhood. With homesteads at just over half the homes, it reads as a place people settle into rather than churn through.
The setting & the homes.
Aerial and on-site photos of Pleasant Park. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
Photos from Stellar MLS listings in Pleasant Park; content deemed reliable but not guaranteed.
Who Pleasant Park is best for.
Best for
- Buyers targeting an established Winter Garden address who will price a home on its own condition
- Renovation-minded buyers who see upside in a compact original footprint
- Long-hold owner-occupants who value a settled, low-churn setting
Probably not for
- Buyers who want new, uniform construction with matching comps
- Investors leaning on a deep stack of recent sales to model returns
- Buyers needing large square footage without doing an addition or rebuild
Price History: What Homes Here Have Actually Sold For
Median sale price over the trailing 12 months ending September 20 of each year, from record-level Stellar MLS closed sales. Same methodology as every appreciation figure on this page: the 2026 point ($550K) IS the median in the snapshot above.
Windows contain 0 to 4 sales each (3 in the current window); every figure carries its sample size, and thin markets swing on single closings. Based on Stellar MLS data distributed by MLS GRID for the period 2004 through 2026. Deemed reliable but not guaranteed.
29% of homes for sale in ZIP 34787 are already under contract (under contract ÷ under contract + active listings) — a read on how much of the available inventory buyers have already claimed. Source: MLS data (2026-09-20).
Pleasant Park Market Scorecard
Pleasant Park is currently a balanced market..
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, refreshed twice daily. Market metrics only; these describe homes for sale and recent sales, not residents.
Housing distress & ownership in Pleasant Park, Winter Garden
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 September 2026 through September 2026. Deemed reliable but not guaranteed.
Pleasant Park on the map.
Every active, pending, and recently sold home, plotted. Toggle the layers and tap a home for the details.
Listing locations from Stellar MLS. Map data © OpenStreetMap, tiles © CARTO.
The Pleasant Park buying strategy.
If we were buying in Pleasant Park 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 Pleasant Park.
A neighborhood of vintages, not a single product
The defining fact here is age diversity. A build range from 1909 to 2024 around a 1955 median means you will find early-century character homes, mid-century cottages, and recent construction sometimes within the same few blocks. There is no single floor plan or era to anchor to, which is exactly why generalizations about 'the Pleasant Park home' fall apart. You buy the specific house.
That variety shows up in size, too. A median around 1,500 square feet points to compact original footprints, and in a market like this the additions, rebuilds, and gut renovations are what separate the numbers. Roughly half the homes carry a homestead, which supports a settled, owner-occupied tone rather than a heavy investor rotation.
The location and the amenities are priced into every listing in Pleasant Park. The deal is won or lost on condition, the comps, and the renovation math.
Why work with Momentum here
In a neighborhood this varied, with a thin recent-sales window, the price signal is easy to misread. We underwrite each home on its own vintage, footprint, and condition instead of leaning on a blunt neighborhood average, and we will tell you plainly when an asking price is fighting the fundamentals.
Pleasant Park 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 Pleasant Park 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 Pleasant Park sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Pleasant Park, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Pleasant Park home worth?
Get a no-obligation home value based on real comparable sales in Pleasant Park, 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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Frequently Asked Questions
What is the median home price in Pleasant Park?
How long do homes in Pleasant Park take to sell?
How many homes are in Pleasant Park?
What share of Pleasant Park is owner-occupied?
When were the homes in Pleasant Park built?
Who is the best real estate agent for Pleasant Park?
How do I find a top Winter Garden real estate agent who knows Pleasant Park?
Can Momentum Realty connect me with an agent for Pleasant Park?
Where is Pleasant Park, and what county is it in?
Should you buy in Pleasant Park?
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: October 1, 2026) |
| Community market stats | Stellar MLS closed sales, 12-month windows ending September 20, 2026 |
| Housing stock & ownership | Florida DOR assessment roll (street-list match (7 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2004 (29 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?
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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 Pleasant Park fits the bigger picture — live prices, inventory, and Momentum Scores:
More on Pleasant Park
- Home values · What homes in Pleasant Park actually sell for
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