Wintermere Pointe Homes for Sale
Winter Garden 34787 · Tilden Road
Wintermere Pointe Homes for Sale in Winter Garden, FL
A gated Winter Garden neighborhood of larger single-family homes built around 2000 by Cambridge Homes, at Tilden Road and Winter Garden Vineland Road, with a tennis court, playground, interior ponds, and SR 429 less than a mile away.
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Live listings
Current Wintermere Pointe homes on the market.
$580,000Median sold price (12 months · 13 sales)
37 daysMedian days on market (CDOM)
2000 to 2001Typical year built (middle 50% of sales)
Stellar MLS sold data, closings Oct 3, 2025 through Oct 2, 2026.
| Fact | Figure |
|---|---|
| Closed sales (last 12 months) | 13 |
| Median sold price (last 12 months) | $580,000 (13 sales) |
| Median price per sq ft | $239 |
| Median days on market | 37 days (CDOM) |
| Single-family median (sold) | $580,000 (13 sales) |
| Typical year-built range | 2000 to 2001 (middle 50% of sales) |
| Legal subdivision names | Wintermere Pointe, Wintermere Pointe Ph 02 46/141, Wintermere Pointe Phase 2 |
| ZIP | 34787 |
Sources: Stellar MLS (sold closings 2025-10-03 to 2026-10-02); Stellar MLS listing records for Wintermere Pointe (community features and association, Oct 2026).
Where is Wintermere Pointe in Winter Garden?
Wintermere Pointe sits at the northeast corner of Tilden Road and Winter Garden Vineland Road (CR 535), with its gated entry on Tilden Road. SR 429 is less than a mile north, Florida’s Turnpike is a few miles east, and Winter Garden Village and Hamlin are both a short drive away. Streets inside the gate include Wintermere Pointe Drive, Prairie View Drive, Grove View Drive, and Tall Oak Drive.
Location snapshot
- ZIP: 34787
- City: Winter Garden, Orange County
- Roads: Tilden Road, Winter Garden Vineland Road (CR 535)
- Highways: SR 429, Florida’s Turnpike
- Entry: gated, no guard
What’s around
- Mall: Winter Garden Village
- Retail and dining: Hamlin
- Downtown: Plant Street, Winter Garden
- Theme parks: via SR 429
- Schools: check Orange County Find My School by address
What amenities does Wintermere Pointe include?
Wintermere Pointe is a gated community with no guard and a mandatory HOA. Listing records describe a tennis court, a playground, a park, sidewalks, and private roads maintained by the association, and some homes back to the community’s interior ponds. There is no community pool in the listing records, and many homes have their own. Ask us for the current HOA dues on any address you like.
Gated entryGated community, no guard
TennisCommunity tennis court
Parks & playPark and playground
PondsInterior ponds; water views on select lots
Private roadsMaintained by the association
HOAMandatory HOA; we pull current dues per address
What do Wintermere Pointe homes typically look like?
Wintermere Pointe is all single-family homes built by Cambridge Homes, and the 13 sales in the last 12 months were built from 1999 to 2003. Heated living areas in that sample ran from 1,950 to 3,741 square feet with 4 or 5 bedrooms, and 7 of the 13 sales recorded a private pool. Sold prices ranged from $469,000 to $880,000, with the larger 5-bedroom homes at the top of that range. Treat these figures as a guide to the sample, not a promise for a specific listing.
How does Wintermere Pointe compare to nearby Winter Garden options?
Buyers who like Wintermere Pointe often compare it with other established Winter Garden communities near SR 429 rather than the newer Horizon West villages. For another established option nearby, see Stoneybrook West homes for sale. When you are budgeting a move, Winter Garden Property Taxes Explained (2026) covers what to expect on the tax bill. Then use this page for active Wintermere Pointe inventory.
Frequently asked questions
Where is Wintermere Pointe located?
Wintermere Pointe is in Winter Garden, ZIP 34787, at the northeast corner of Tilden Road and Winter Garden Vineland Road (CR 535). The gated entry is on Tilden Road, and SR 429 is less than a mile north.
What do Wintermere Pointe homes sell for?
Across 13 closed sales from October 3, 2025 through October 2, 2026, the median sold price was $580,000, or $239 per square foot, with a median of 37 days on market. Sold prices ranged from $469,000 to $880,000.
Is Wintermere Pointe gated, and what amenities does it have?
Yes, it is gated with no guard. Listing records describe a tennis court, playground, park, sidewalks, and association-maintained private roads, plus interior ponds. There is no community pool in the listing records.
Who built Wintermere Pointe, and how old are the homes?
Cambridge Homes built Wintermere Pointe. Homes sold in the last 12 months were built from 1999 to 2003, and the middle 50% were built in 2000 to 2001. All were single-family homes with 4 or 5 bedrooms.
How do I see current Wintermere Pointe homes for sale?
Use the live listings block on this page for active inventory, or call or text the Jared Jones Team at 407-706-5000. We can also set a custom alert for new Wintermere Pointe and nearby Winter Garden listings that match your budget and must-haves.
Sources
- Stellar MLS: Wintermere Pointe sold closings, 2025-10-03 to 2026-10-02 (13 sales; median $580,000; $239/sf; 37 CDOM)
- Stellar MLS listing records: Wintermere Pointe community features and association (Oct 2026)
- Orange County Public Schools Find My School: school assignment by address
Browse nearby
Thinking about a home in Wintermere Pointe?
Call or text the Jared Jones Team at 407-706-5000. We will pull current comps, get HOA details on the homes you like, and set up showings.