Wintermere Pointe
Homes for Sale in Winter Garden, FL
All 750 homes for sale in Winter Garden, FL · median $585,000 · 679 homes for sale in 34787 · Orange County homes for sale
True comps, carrying-cost math, and listings before the portals.
As of October 2026, wintermere pointe in Winter Garden, FL has 2 homes for sale. Over the 12 months ending 2026-09-20, 8 recorded sales closed at a median of $559,950, $243 per square foot, a median 15 days on market, sellers accepting 98% of original asking (-19% versus the prior year). Homes listed or recently sold were built 1999 - 2001; 12 of 12 report an HOA (median $90/mo); none of the 12 geocoded homes sit in a FEMA special flood hazard zone (median elevation 114 ft). At the median price and Orange County's FY2025-26 rate of 16.67 mills, annual property tax runs about $9,340 ($8,660 with the full homestead exemption).
Last 30 days in Wintermere Pointe: 1 new listing (median asking $790,000), 1 closed sale (median $550,000). As of October 14, 2026, Listings courtesy of Stellar MLS as distributed by MLS GRID.
Wintermere Pointe right now
🟡 Balanced market. 2.7 months of supply and 33% of the inventory already under contract put buyers and sellers on roughly even footing.Why it matters: months of supply is how long today's inventory would last at today's sales pace; under-contract share is the portion of homes for sale that already have a buyer.Momentum Research analysis of Stellar MLS records, as of September 20, 2026. Confidence: Medium (3 active and pending listings, 8 closed sales in 12 months).
🔴 Off the recent peak. The trailing-12-month median ($560K) is down 18.6% from the prior 12 months ($688K). With about 3 sales a year, a single closing can swing this number, so read the level and the decade, not one year's move.Momentum Research, record-level Stellar MLS closed sales, 12-month windows ending September 20. Confidence: Low (8 and 4 sales in the two windows).
Jump to: Price history & scorecard · Homes for sale · Schools · FAQ
· Updated October 15, 2026 · Live data: Stellar MLS, refreshed twice daily · MLS facts carry their source; interpretation lines are Momentum Research · Data sources & freshness
The 60-Second Overview
Wintermere Pointe market snapshot (as of September 20, 2026): the median sale price is about $560K ($243 per sq ft over the trailing 12 months of closed sales), a median 16 days on market for closed sales, and 2.7 months of supply, a balanced market. The trailing-12-month median is down 19% from the prior 12 months, computed from record-level Stellar MLS closed sales (8 closings in the current window).
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 11 qualified sales in wintermere pointe across 2024 - 2025 (5 in 2024, 6 in 2025), median $660,000 - the last recorded sale per parcel on the Florida DOR 2025 assessment roll, independent of the MLS.
Flood zones in Wintermere Pointe: of 10 listing addresses checked against the FEMA National Flood Hazard Layer, 100% sit outside the FEMA Special Flood Hazard Area (Zone X). Individual parcels vary - verify any specific address at msc.fema.gov. See flood zones by neighborhood in Winter Garden.
Wintermere Pointe is a community of 202 homes in Winter Garden, Orange County, built between 1999 and 2005 (median 2002), with a median living area of about 2,901 square feet. 81% of parcels are homesteaded, the owner-occupancy proxy in the Florida DOR assessment roll (2025 roll, public records).
The setting & the homes.
Aerial and on-site photos of Wintermere Pointe. Swipe to explore the community.
Swipe or use the arrows → tap any photo to enlarge
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Wintermere PointePhotos from Stellar MLS listings in Wintermere Pointe; content deemed reliable but not guaranteed.
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 ($560K) IS the median in the snapshot above, and the move from 2025 ($688K) IS the -18.6% one-year change.
Windows contain 0 to 8 sales each (8 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 2005 through 2026. Deemed reliable but not guaranteed.
31% 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 (2026-10-15).
WINTERMERE POINTE Market Scorecard
WINTERMERE POINTE is currently a strong seller's market. About 2.4 months of supply, a median asking price of $777,500, and homes go under contract in about 32 days.
Typical home value in the 34787 ZIP is $570,875, right around the Florida norm (Zillow Home Value Index).
Go deeper: ZIP market scorecard · county scorecard · true cost calculator · affordability calculator.
Live data: Stellar MLS, distributed by MLS GRID, refreshed twice daily. Typical value: Zillow Research. Market metrics only; these describe homes for sale and recent sales, not residents.
Homes For Sale Right Now in Wintermere Pointe
Live MLS inventory for Wintermere Pointe. Every active listing, what is under contract right now, and the last 12 months of closed sales, refreshed twice a day. Closed comps beat an algorithm's guess every time.
Active and pending Wintermere Pointe listings as of 2026-10-14, priced high to low. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026. Tap any home to ask about it.
Wintermere Pointe 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.
Life at Wintermere Pointe
- Playground · reported on 7 of 10 listings
- Gated Community - No Guard · reported on 7 of 10 listings
- Tennis Court(s) · reported on 6 of 10 listings
- Gated · reported on 5 of 10 listings
- Gated Community · reported on 5 of 10 listings
- Deed Restrictions · reported on 4 of 10 listings
- Pickleball Court(s) · reported on 2 of 10 listings
- Association Recreation - Owned · reported on 1 of 10 listings
- Security Lights · reported on 1 of 10 listings
- Fence Restrictions · reported on 1 of 10 listings
- Park · reported on 1 of 10 listings
- Vehicle Restrictions · reported on 1 of 10 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.
Recent Developments in Wintermere Pointe
Development, infrastructure, retail, and school activity affecting Wintermere Pointe, tracked by our team and summarized from public reporting and official sources, with links to the original coverage. Last updated October 2026.
- September 2026Development
Orange County commissioners approve Tuscana land use plan in Shingle Creek Basin on 4-3 vote
Commissioners voted 4-3 to approve the Tuscana land use application from Shingle Creek Co-Owners LLC and Geyer Development, reversing a unanimous rejection in May 2025. The plan includes more than 1,000 hotel rooms, about 4,000 apartments and commercial buildings, with conditions for a raised road, flood mitigation and wetland protection. The developer projects thousands of jobs at full build-out.
What it may mean for the marketThe approval could add substantial rental housing, hotel capacity and commercial space in the Shingle Creek area, while flood-mitigation conditions will shape how and when it is built. The project is about 11 miles southeast of Wintermere Pointe, elsewhere in Orange County.
Source: Spectrum News 13 - 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 9 miles southwest of Wintermere Pointe.
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 9 miles southeast of Wintermere Pointe.
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 12 miles east of Wintermere Pointe, 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 8 miles northeast of Wintermere Pointe, elsewhere in Orange County.
Source: Orange County Newsroom - 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 13 miles north of Wintermere Pointe, 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 the Orlando Metro.
The Wintermere Pointe buying strategy.
If we were buying in Wintermere Pointe 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 Wintermere Pointe.
A closer look at the Wintermere Pointe market
At a median of $243 per square foot, Wintermere Pointe prices sit in a fairly defined band, so condition and updates — more than the list price — tend to separate one home from the next.
Inventory runs at 2.7 months of supply, a balanced market and the trailing-12-month median down 19% year over year. Homes that do trade take a median 16 days on market, useful leverage on any listing that has lingered.
The housing stock is 202 homes built between 1999 and 2005, and 81% of parcels are homesteaded — the owner-occupancy proxy in the Florida DOR assessment roll.
The location and the amenities are priced into every listing in Wintermere Pointe. The deal is won or lost on condition, the comps, and the renovation math.
Momentum Buy Score.
Our proprietary 0 to 10 read across the factors that decide how a home in Wintermere Pointe buys, holds, and resells. Momentum Research; not an appraisal.
Momentum Intelligence Scores are our proprietary, qualitative assessment on a 0 to 10 scale, built from the record-level market data on this page. They are a framework for comparing communities, not a guarantee of future value and not advice on a specific home; unlike an automated value estimate they do not price your home, they grade the community on evidence you can inspect. Composite is the plain average of the 4 factors (6.3). Basis: Recent Direction -18.6% year-over-year; Liquidity & Demand 2.7 months of supply; Owner Commitment 81% owner-occupied; Pricing Power 97.5% sale-to-list. Refreshed with each data update.
What it really costs to own in Wintermere Pointe
The parts of the monthly number a mortgage calculator leaves out, from the tax roll, the MLS, Citizens and FEMA. Property facts only.
| HOA dues | Median $90/month across 363 MLS listings (most billed annually; 2026-10-15). Dues cover what the documents say they cover; ask for the budget and reserve study. |
|---|---|
| Home and flood insurance | The average Citizens Property Insurance premium in Orange County is $1,409/yr (4,204 policies, Citizens detail by county, April 2026); private-market quotes depend on roof age, wind mitigation and construction. Flood: of 10 listing addresses checked against the FEMA flood map, 100% sit outside the high-risk zone. Statewide, a Zone X flood policy runs about $500-$700/yr and a high-risk zone $1,200-$2,500/yr (FEMA Risk Rating 2.0 averages, not quotes). |
| Roof and age | Median build year 2000 across 12 listings. An original roof here would be about 26 years old; under Florida's 2022 reform (SB 2-D) carriers may require an inspection past 15 years, so budget for a roof report, and for replacement where it fails. |
Email me new listings in Wintermere Pointe
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 Wintermere Pointe
Have a question about the homes, fees, rules or commute here? A Momentum agent who works Wintermere Pointe will answer, and the answer is published on this page for the next buyer.
HOA, CDD & Fees
- HOA dues reported around $90/month (about $1,080/yr) · median of 363 MLS listings, most billed annually
- Any club/amenity membership is billed separately
Listings in this community report association dues of about $90 per month ($1,080 a year) - the median AssociationFee across 363 MLS records, normalised to a monthly figure; most are billed annually. Dues change with budgets and can differ by section or product type; confirm the current figure with the association before you offer. Source: MLS listing records, 2026-10.
Confirm the current HOA dues, exactly what they cover, and any CDD bond or special assessment for a specific address before you offer.
Flood & Insurance Context
Of 10 sampled listing addresses in this community: 100% outside the FEMA Special Flood Hazard Area (Zone X/B/C).
Address-sampled; individual parcels vary - verify any specific address at msc.fema.gov. Check any address at FEMA's Flood Map Service Center, and see average home-insurance costs by Florida county.
Source: FEMA National Flood Hazard Layer, address-level lookups (n=10) · as of 2026-10
Tools for a Wintermere Pointe 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 Wintermere Pointe sales matched to your home.
Price it to the comps and condition, not an automated estimate.
If you are thinking about selling in Wintermere Pointe, the right list price comes from recent comparable sales matched to your home's condition and location, not an automated estimate.
What is your Wintermere Pointe home worth?
Get a no-obligation home value based on real comparable sales in Wintermere Pointe, 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 →
Recently off market in wintermere pointe
Homes in wintermere pointe 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. 3 on record.
- 2006 Wintermere Pointe Drive · off market
- 2025 Wintermere Pointe Drive · off market
- 2031 Wintermere Pointe Drive · off market
| Location | Winter Garden, Orange County, FL · ZIP 34787 |
|---|---|
| Homes in the community | 202 (FL DOR 2025 assessment roll) |
| Years built | 1999–2005 (median 2002) |
| Typical living area | 2,901 sq ft (median) |
| Home types (current listings and sales) | single-family 100% |
| Amenities listed by sellers | Gated, Playground, Tennis Court(s), Gated Community - No Guard, Deed Restrictions, Gated Community |
| Sale prices, last 12 months | $559,950 median across 8 closed sales · $243 per sq ft · -18.6% vs the prior 12 months |
| Days on market (closed sales) | 15 median |
| For sale right now | 2 active, 1 pending · median asking $792,500 · 2.7 months of supply |
| Owner-occupied (homestead) share | 81% |
Data as of September 20, 2026. Based on Stellar MLS data distributed by MLS GRID for the period 2005 through 2026; housing-stock figures from Florida Department of Revenue public records. Market figures describe homes, not residents. Cite as: Momentum Realty, “Wintermere Pointe key facts,” movewithmomentum.com/neighborhoods/wintermere-pointe-winter-garden, data as of September 20, 2026.
Housing distress & ownership in wintermere pointe, 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 October 2026 through October 2026. Deemed reliable but not guaranteed.
Just listed in Wintermere Pointe
The newest homes for sale in Wintermere Pointe right now, newest first. Each link opens the full listing with every photo, the price history and a tour request.
- 2242 Wintermere Pointe Drive $790,000 · 5 bd · 4 ba · 3,381 sq ft · 14 days on market Courtesy of NEXTHOME BEST RESULTS REAL ESTATE
- 2157 Wintermere Pointe Drive $765,000 · 5 bd · 3.5 ba · 3,197 sq ft · 50 days on market Courtesy of SOUTH EARTH REALTY LLC
Checked against the MLS Oct 15, 2026. All new listings in this market.
Every Home for Sale in Wintermere Pointe Winter Garden Right Now (2)
All 2 active and pending Wintermere Pointe Winter Garden listings with a detail page, newest first, refreshed twice a day from the MLS.
- 2242 Wintermere Pointe Drive · $790,000 · 5 bd / 4 ba · listed Sep 14, 2026 · listed by Nexthome Best Results Real Estate
- 2157 Wintermere Pointe Drive · $765,000 · 5 bd / 3.5 ba · listed Sep 1, 2026 · listed by South Earth Realty Llc
Recently sold in Wintermere Pointe Winter Garden
- 2031 Wintermere Pointe Drive · sold $550,000
- 2025 Wintermere Pointe Drive · sold $715,000
- 2006 Wintermere Pointe Drive · sold $740,000
- 2031 Wintermere Pointe Drive · sold $469,000
Closed sales from the MLS; each page shows the sold price, taxes and value history.
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Streets in this community
Street-level pages: every home on record, what sold and what is for sale on each street.
- Wintermere Pointe Drive (36 homes on record)
- Prairie View Drive (16 homes on record)
- Wintermere Pointe Drive (6 homes on record)
- Prairie View Drive (5 homes on record)
- Wintermere Pointe Drive (3 homes on record)
- Wintermere Pointe Drive (3 homes on record)
- Wintermere Pointe Drive (2 homes on record)
- Wintermere Pointe Drive (2 homes on record)
- Prairie View Drive (2 homes on record)
- Prairie View Drive (2 homes on record)
- Wintermere Pointe Drive (1 homes on record)
- Prairie View Drive (1 homes on record)
Frequently Asked Questions
What is the median home price in Wintermere Pointe?
How long do homes in Wintermere Pointe take to sell?
Is Wintermere Pointe a buyer's or seller's market right now?
How many homes are in Wintermere Pointe?
What share of Wintermere Pointe is owner-occupied?
When were the homes in Wintermere Pointe built?
Who is the best real estate agent for Wintermere Pointe?
How do I find a top Winter Garden real estate agent who knows Wintermere Pointe?
Can Momentum Realty connect me with an agent for Wintermere Pointe?
Where is Wintermere Pointe, and what county is it in?
Is Wintermere Pointe in a flood zone?
Is Wintermere Pointe a good place to live?
Data sources & freshness
| Live listings | Stellar MLS, refreshed twice daily (last: October 14, 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 (8 streets, ZIP 34787)) |
| Under-contract shares | Stellar MLS records, as of 2026-09-20 |
| Historical depth | Closed-sale records back to 2005 (46 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 Wintermere Pointe
- Home values · What homes in Wintermere Pointe actually sell for
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