Wintermere Pointe

Explore Winter Garden Real Estate at Wintermere Pointe. With its palm tree-lined gated entrance and proximity to a multitude of shops and restaurants at Winter Garden Village, Wintermere Pointe, is located off Winter Garden Vineland Road and Wintermere Pointe Drive or Tilden Road and Rockrose Drive. 

Wintermere Pointe Homes for Sale

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New
Timberlane Road, LAKE WALES

$215,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448344
New
Timberlane Road, LAKE WALES

$269,000

Timberlane Road, LAKE WALES

0 Beds 0 Baths 0 SqFt Land MLS® # O6448343
New Open House
20 Walden, ORMOND BEACH

$349,900

20 Walden, ORMOND BEACH

3 Beds 2 Baths 1,874 SqFt Residential
Sat, Oct 10th, 2026 @ 12pm - 3pm
MLS® # V4951731
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447200
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447201
New
Green Lake Drive, EUSTIS

$75,000

Green Lake Drive, EUSTIS

0 Beds 0 Baths 0 SqFt Land MLS® # O6447198
Pending
1624 Sterns Drive, LEESBURG

$285,000

1624 Sterns Drive, LEESBURG

4 Beds 2 Baths 2,936 SqFt Residential MLS® # O6425853
New
3110 Emerald Acres Lane, SANFORD

$374,500

3110 Emerald Acres Lane, SANFORD

3 Beds 3 Baths 1,682 SqFt Residential MLS® # S5159186
New
5714 Cattle Ranch Drive, ST CLOUD

$3,095

5714 Cattle Ranch Drive, ST CLOUD

4 Beds 4 Baths 3,058 SqFt Residential MLS® # O6448300
1211 Nixonton Street, DELTONA

$440,000

1211 Nixonton Street, DELTONA

3 Beds 3 Baths 2,208 SqFt Residential MLS® # V4951068
New
140 Bombay Avenue, WINTER SPRINGS

$355,000

140 Bombay Avenue, WINTER SPRINGS

3 Beds 2 Baths 1,373 SqFt Residential MLS® # O6448262
New
31744 Boadwater Ave, LEESBURG

$369,900

31744 Boadwater Ave, LEESBURG

4 Beds 3 Baths 2,626 SqFt Residential MLS® # O6447594
New
5381 Maddie Drive, HAINES CITY

$399,900

5381 Maddie Drive, HAINES CITY

5 Beds 3 Baths 3,011 SqFt Residential MLS® # O6446669
New Open House
1249 Waterwitch Cove Circle, ORLANDO

$874,900

1249 Waterwitch Cove Circle, ORLANDO

3 Beds 3 Baths 2,715 SqFt Residential
Sat, Oct 10th, 2026 @ 1pm - 4pm
MLS® # O6446291
New
1881 Red Canyon Drive, KISSIMMEE

$310,000

1881 Red Canyon Drive, KISSIMMEE

3 Beds 3 Baths 1,624 SqFt Residential MLS® # O6448530

Sold Homes in Wintermere Pointe Winter Garden

Wintermere Pointe Real Estate Market Statistics

Average Price $837K
Lowest Price $790K
Highest Price $925K
Total Listings 3
Avg. Days On Market 58
Avg. Price/SQFT $243
List to Sell Price Percentage 99 %

Property Types (active listings)

Winter Garden Communities

Built in 1999 through 2004, this well-established community offers a variety of spacious homes that range in size between approximately 1,800 square feet to over 4,200 square feet and provide between 4 and 5 bedrooms, 2 to 4 baths, and 2 to 3 car garages. Some homes boast peaceful conservation views, and others offer lovely pond views. Many homes feature screen lanais and offer private pools. A community tennis court is located centrally, perfect to gather with fellow neighbors for a friendly match.

While the community is nicely tucked away, it is convenient to one of the premiere shopping complexes in the area – Winter Garden Village – is a major draw. With 92 shops and restaurants, the complex, which is just 2 miles away, has something for everyone, from big box stores to eclectic boutiques and trendy clothing shops, and from fast food chains to casual dining experiences. There’s also a Publix Grocery Store just 3.5 miles away and a Walmart Supercenter just 5 miles away. Also just 5 miles away is charming Winter Garden Village, which offers visitors a wide variety of restaurants and bars, a live performance theater, an art gallery, a local museum, and a weekly Farmers Market.

When it’s time for fresh air and recreation, there are multiple options within just a few miles. West Orange Trail offers visitors a scenic, 22-mile-long trail that passes through downtown Winter Garden, Oakland, and Apopka. Nearby, West Orange Country Club provides golfers with challenging holes and scenic views. Theme park enthusiasts will love Wintermere Pointe, as Walt Disney World Resort is a short 6-mile drive away.

Call us today to find out more about Wintermere Pointe.

Wintermere Pointe Community Information

  • Location: Winter Garden Vineland Road and Wintermere Pointe Drive or Tilden Road and Rockrose Drive
  • Year Built: 1999 - 2004
  • Number of Homesites: 204 single-family homesites
  • HOA: Yes

Orange County Area Schools

  • Lake Whitney Elementary School: Grades 1st – 5th Distance: 3 miles
  • Sunridge Middle School: Grades 6th – 8th Distance: 5 miles
  • West Orange High School: Grades 9th - 12th Distance: 3 miles

Dining and Shopping

  • Winter Garden Village – Distance: 2 miles
  • Windermere Village – Distance: 2.5 miles
  • Stoneybrook with Publix Grocery Store – Distance: 3 miles
  • Lake Burden Shops – Distance: 4 miles
  • Shoppes at Belmere – Distance: 4.5 miles
  • Winter Garden Regional Shopping Center – Distance: 4.5 miles
  • Meadow Ridge Mall – Distance: 4.5 miles
  • Shoppes of Winter Garden – Distance: 5 miles
  • Walmart Supercenter – Distance: 5 miles
  • Winter Garden Plaza – Distance: 6 miles
  • Downtown Orlando – Distance - Distance: 16 miles

Parks and Recreation

  • West Orange Country Club – Distance: 1 mile
  • Dr. Bradford Memorial Park – Distance: 1 mile
  • Windermere Recreation Area – Distance: 3 miles
  • George Bailey Park – Distance: 3.5 miles
  • VanderLey Park – Distance: 4 miles
  • Tucker Ranch Recreation and Nature Complex – Distance: 4 miles
  • Johns Lake Preserve – Distance: 4.5 miles
  • West Orange Park – Distance: 4.5 miles
  • Johns Lake Preserve – Distance: 5 miles
  • West Orange Trail Park – Distance: 5 miles
  • Maple Street Park – Distance: 5 miles
  • Tildenview Park – Distance: 6 miles
  • Newton Park – Distance: 6 miles
  • Dr. Bradford Memorial Park – Distance: 6 miles
  • Zander’s Park and Bouler Pool – Distance: 7 miles
  • Palm Park – Distance: 7.5 miles
  • Chapin Station – Distance: 8 miles
  • Speer Park – Distance: 8 miles
  • Amway Center – Distance: 16 miles

Theme Parks

  • Walt Disney World Resort – Magic Kingdom – Distance: 6.5 miles
  • Universal Studios – Distance: 15.5 miles
  • SeaWorld – Distance: 20 miles

Hospitals

  • AdventHealth Winter Garden Hospital – Distance: 2 miles

*Distances are approximately measured from Wintermere Pointe community entrance.

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