Wesmere Homes for Sale
Gated 1990s community with waterfront ponds, resort amenities near Winter Garden.
Inside Wesmere
Wesmere is a gated residential community in southern Ocoee, Florida, developed between 1991 and 1999 primarily by Calton Homes of Florida, with some homes built by Beazer Homes and Arvida. The subdivision encompasses single-family homes ranging from 1,300 to over 3,700 square feet, situated on the south side of Maguire Road and Roberson Road, approximately 9.5 miles west of downtown Orlando. The community’s defining feature is its collection of nearly 100 waterfront homes with views of decorative ponds and fountains, complemented by 16 cul-de-sacs that reduce through-traffic and provide larger lot sizes.
The gated community features comprehensive amenities designed for active living and family recreation. A resort-style pool and clubhouse form the social hub, while additional facilities include three tennis courts, four pickleball courts, basketball court, playground, fitness center, and fishing areas. All homes in Wesmere are subject to mandatory HOA fees ranging from $112 to $755 monthly, which cover common area maintenance, road upkeep, pool and clubhouse operations, security, 24-hour guards, cable television, internet, utilities, and waste removal. The variation in HOA fees reflects differences in home size and amenity access within the community.
Wesmere sits within Orange County Public Schools, with the assigned elementary campus about one mile out, the middle school at 2.5 miles, and the high school around seven miles away. Zoning is assigned by address rather than by subdivision, so check the specific property with the district. The community enjoys convenient access to shopping and dining at nearby Plantation Grove with Publix, Winter Garden Village retail complex, and downtown Windermere boutiques. Highway access is excellent, with the 408 and 429 expressways, Florida Turnpike, and Highway 50 all readily accessible, making commuting to Disney World, Universal Orlando, and downtown Orlando straightforward.
As of February 2026, the market for Wesmere homes remained active, with an average asking price of $558,494 and average selling price of $550,747 over the previous year. Homes typically sold within 45 days, reflecting strong buyer interest in the community. The list-to-sell ratio of 99 percent and price per square foot of $187 indicate a balanced market. Buyers seeking a gated community with established amenities, waterfront appeal, and proximity to both shopping and theme park attractions should contact a Market Connect Realty agent for current inventory and market analysis.
The facts
Frequently asked
What is the price range for homes in Wesmere?
Homes in Wesmere are priced between $460,000 and $649,000, with an average selling price of approximately $550,747 as of early 2026. Homes range from 1,300 to over 3,700 square feet. For the most current listings and pricing, contact a Market Connect Realty agent serving Ocoee.
Is Wesmere a gated community?
Yes, Wesmere is a fully gated community with two main entrances on Maguire Road and Roberson Road. The gates provide 24-hour security with a resident guard. All homes are within the gated boundaries and subject to mandatory HOA rules and fees.
What schools are zoned for Wesmere?
Wesmere's assigned elementary school is roughly 1 mile from the community, with the middle school 2.5 miles out and the high school 7 miles away, all under Orange County Public Schools. Zoning is assigned by address rather than by subdivision, so check the specific property with the district. All schools are part of the Orange County Public Schools system. Confirm current school assignments with the county, as boundaries occasionally change.
What are the HOA fees in Wesmere?
HOA fees in Wesmere range from $112 to $755 monthly depending on home size and location. Fees include common area maintenance, road upkeep, pool and clubhouse operations, 24-hour security, cable TV, internet, utilities, and trash removal. HOA fees vary among homes in the community.
What amenities does Wesmere offer?
Wesmere offers a resort-style pool, clubhouse, three tennis courts, four pickleball courts, basketball court, playground, fitness center, parks, and fishing areas. The community features decorative ponds with fountains and walking trails. Nearly 100 homes offer waterfront views.
How many homes are in Wesmere?
The exact number of homes in Wesmere is not officially published, but approximately 30-35 homes sell annually. The community is one of the larger subdivisions in southern Ocoee. Contact a Market Connect Realty agent for precise current inventory.
Is short-term rental allowed in Wesmere?
Short-term rental policies for Wesmere have not been verified in available sources. Rental restrictions vary by property within the community. Buyers interested in rental income should contact the HOA directly or consult a Market Connect Realty agent for current rules.
What year was Wesmere developed?
Wesmere was developed between 1991 and 1999, primarily by Calton Homes of Florida, with some homes built by Beazer Homes and Arvida. Most homes date to the 1990s, though some were constructed after 2000, making it an established community with mature landscaping.