Winter Garden, FL - West Orange County
Winter Garden is one of the fastest-moving markets in the Orlando metro, with median home prices at $560,500 and homes going under contract in 32 days. SERHANT. Orlando closes deals here every week with cinematic marketing, rigorous pricing strategy, and 40 agents who know every street in West Orange County.
Median Sale Price: $560,500. Median Days on Market: 32. Price per Sq Ft: $249. Active Listings: 480+.
Winter Garden posted a median sale price of $560,500 in early 2026, up roughly 4% year over year. Homes spend a median of 32 days on the market before going under contract. Inventory has risen to over 480 active listings as new-construction deliveries from Pulte, Meritage, and Taylor Morrison continue feeding the pipeline.
Hamlin. Master-planned community with single-family homes ($500K to $800K), townhomes, and a retail village. Two community pools, trail systems, and Hamlin Town Center.
Lakeshore. Pulte flagship Winter Garden community. Homes from the mid-$400Ks to mid-$700Ks with a lakefront amenity center and resort pool.
Crestview at Johns Lake. Established community with larger lot sizes. Homes range from $600K to $1.2M.
Oakland Park. New-construction homes from $400K to $700K with a small-town downtown and charter school.
Windermere Trails.​​​​​​​ On the Winter Garden-Windermere border. Homes from $500K to $900K.
Winter Garden falls within the Orange County Public Schools district, which is the eighth-largest school district in the United States.
Bridgewater Middle School (Rated A) in Horizon West
Windermere High School (Rated A) serving most of western Winter Garden
West Orange High School (Rated B+) serving central and northern Winter Garden
Independence Elementary (Rated A) in Hamlin
Sunridge Elementary (Rated A) in Horizon West
Families relocating from out of state: Orange County offers open enrollment, meaning you can apply to magnet and specialty programs across the district regardless of your home address.
Winter Garden is one of the top new-construction markets in the entire Orlando metro. Active builders include:
Pulte Homes at Lakeshore, starting mid-$400Ks
Meritage Homes at Orchard Park, starting low $500Ks
Taylor Morrison at Waterside, starting low $300Ks (townhomes) to mid-$500Ks (single-family)
Toll Brothers at Lakeside Preserve, starting upper $600Ks
Dream Finders at multiple Horizon West sites
New construction in Winter Garden typically takes 6 to 10 months from contract to closing. Buyers should budget for design center upgrades (usually 8% to 15% above base price), lot premiums ($10K to $50K for lakefront or conservation views), and CDD assessments ($1,500 to $3,500/year).
SERHANT. Orlando represents buyers on new-construction purchases at no cost. Builder sales agents work for the builder. Our job is to negotiate upgrades, protect your inspection rights, and make sure the contract terms work in your favor.
383 transactions closed in 2025 across the Orlando metro
$184.1M in total sales volume
40 licensed agents covering every neighborhood in West Orange County
Cinematic marketing powered by SERHANT. Studios for every listing over $500K
Pricing strategy built on real-time MLS analytics, not gut feeling
Mark Raumaker leads SERHANT. Orlando as Regional Operator. Before launching the Orlando office, Mark built a career in New York City spanning Broadway, the Metropolitan Opera, and luxury real estate. That background in performance, negotiation, and client service translates directly into how SERHANT. Orlando operates: every listing gets a strategy, every buyer gets an advocate, and every deal gets closed with precision.
Whether you are listing a home, comparing communities, or evaluating a new construction contract, our Winter Garden specialists are ready to talk. No obligation, no pressure, just straight answers from agents who close here every week.