Pleasant Park
Homes for Sale in Winter Garden, FL
All 749 homes for sale in Winter Garden, FL · median $589,900 · 706 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
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.
Figures in this note are as of July 13, 2026. The live market numbers elsewhere on this page update nightly and are newer.
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), 2,123 homes closed in the last 12 months at a median of $595K ($252/sq ft), down 0.9% year over year, with a median 37 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
Pleasant Park
Pleasant Park
Pleasant ParkPhotos 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.
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 contributors.
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.
See all homes for sale in Winter Garden →
| 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.
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.
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Winter Garden 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
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Recent Developments in Pleasant Park
Development, infrastructure, retail, and school activity affecting Pleasant Park, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Lake County approves 2,241-acre Panther Run rezoning for up to 2,624 homes near Clermont
The Lake County Commission voted 3-1 on Sept. 1 to rezone about 2,241 acres in the Wellness Way area, north of Sawgrass Bay Boulevard, for GT Homes. The planned unit development allows up to 2,624 residential units and more than 1 million square feet of non-residential space, with sites reserved for a future public high school and public safety facilities. Plans include extending County Road 455 and about 11 miles of public trails.
What it may mean for the marketThe plan adds long-term housing supply, employment space and new connector roads in south Lake County, with infrastructure planned ahead of residential growth. The site is about 12 miles southwest of Pleasant Park.
Source: Clermont Sun - August 2026Retail & Dining
Plans for Mattel indoor water park near Lake Buena Vista Factory Stores expand to 13 acres
Updated plans for the site off State Road 535 show a 95,000-square-foot indoor water park designed by Martin Aquatic, a separate 45,000-square-foot entertainment building and nearly 900 parking spaces. The tower height rises to as much as 100 feet and still needs Orange County approval. About 200 jobs are expected, and no opening date has been announced.
What it may mean for the marketThe project would add visitor attractions, dining and roughly 200 jobs near the State Road 535 corridor, with added traffic and parking demand nearby. The site is about 10 miles south of Pleasant Park.
Source: FOX 35 Orlando - July 2026Development
Orange County opens Enclave at Canopy Park with 104 affordable units
Orange County opened The Enclave at Canopy Park, a 104-unit affordable apartment community at 4440 Canopy Park Loop developed by Archway Partners. The county contributed 3 million dollars from its Affordable Housing Trust Fund. The community includes one and two bedroom homes plus a community center, fitness center, technology lab, and EV charging.
What it may mean for the marketAdds 104 income-restricted apartment homes to the local rental supply along with new community amenities and green-certified construction. The project is about 11 miles east of Pleasant Park, elsewhere in Orange County.
Source: ClickOrlando - July 2026Civic
Orange County previews new Innovation Center on West Colonial Drive
Orange County previewed its new Innovation Center at 7149 West Colonial Drive, located within the county's Multicultural Center and Senior Center complex, with an official opening set for Fall 2026. The center will offer technology programs including 3D printing and makerspace prototyping through the Orange County Library System, plus career exploration and workforce training through CareerSource Central Florida.
What it may mean for the marketAdds a county operated civic and technology facility with library and workforce programming to the West Colonial corridor. The project is about 6 miles east of Pleasant Park, elsewhere in Orange County.
Source: Orange County Newsroom - June 2026Development
Mixed-use high-rise redesigned for 924 and 934 North Magnolia Avenue
A redesigned 17-story mixed-use high-rise was proposed for 924 and 934 North Magnolia Avenue in Orlando's North Quarter district by Acram Group. The project would include 350 residential units, about 3,300 square feet of ground-floor commercial space, and a parking garage with 510 spaces, replacing two 1972 office buildings. A public plaza is planned at the corner of Magnolia and Weber Street.
What it may mean for the marketWould replace two aging office buildings with 350 residences, ground floor retail, and structured parking, adding housing density and a public plaza along the Orlando Urban Trail. The project is about 11 miles east of Pleasant Park, elsewhere in Orange County.
Source: Florida YIMBY - October 2025Retail & Dining
New Apopka complex with restaurants and offices set to open in 2026
A new commercial complex in Apopka with restaurants and office space is set to open in 2026, adding retail and workplace space in northwest metro Orlando.
What it may mean for the marketNew retail and office space in Apopka adds everyday conveniences and local jobs, amenity and employment factors that can support nearby housing demand. The project is about 10 miles north of Pleasant Park, elsewhere in Orange County.
Source: GrowthSpotter
Summaries reflect public reporting and official sources linked above as of the dates shown. Project details, timelines, and approvals can change. Commentary on potential market effects is general observation, not investment advice or a prediction for any specific property. For the freshest items across the whole region, see This Week in Northeast Florida.
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 19, 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.
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More on Pleasant Park
- Home values · What homes in Pleasant Park actually sell for
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