Pleasantville

Welcome to Pleasantville

Pleasantville blends historic small-town charm with modern conveniences, offering scenic streets, strong schools, and a close-knit community. Residents enjoy a walkable downtown, cultural amenities, and abundant green spaces, creating a comfortable and refined lifestyle.

Overview

Located in northern Westchester County, Pleasantville provides a quintessential suburban experience with easy access to New York City via Metro-North. The village’s historic architecture, tree-lined streets, and active community make it highly desirable for families and professionals alike.

• Grand Central: ~50 min by train
• Airports: Westchester County ~25 min, LaGuardia ~35 min, JFK ~50 min
• Population: ~7,000 residents
• Community Character: Walkable downtown, boutique shops, vibrant dining, and strong neighborhood cohesion

Neighborhoods & Lifestyle

Pleasantville’s neighborhoods feature a mix of historic homes, mid-century houses, and newer developments, providing options for various tastes and family sizes:

• Downtown Village – Pedestrian-friendly with boutique shopping, cafés, and restaurants
• Residential Streets – Tree-lined avenues with charming single-family homes and well-maintained yards
• Suburban Periphery – Larger lots, quiet streets, and proximity to parks and nature preserves

The village fosters community engagement, with residents participating in local festivals, farmers’ markets, and cultural events throughout the year.

Schools

Education is a cornerstone of Pleasantville life. The Pleasantville Union Free School District is highly regarded for its academics, extracurricular programs, and community involvement:

• Pleasantville High School & Middle School – Strong academic performance, athletics, and arts programs
• Elementary Schools – Focused on small class sizes and individualized attention
• Community Advantage: Family-oriented environment with active parent participation

Families often consider school proximity and district reputation when selecting homes in Pleasantville.

Dining, Culture, & Entertainment

Pleasantville offers a vibrant cultural scene for a village of its size:

• Jacob Burns Film Center – Independent and international cinema with educational programs
• Pleasantville Music Festival – Annual event featuring renowned artists and live performances
• Pleasantville Farmers Market – Year-round market with over 50 vendors, local produce, and live music
• Dining – Mix of casual cafés, bistros, and fine dining that reflects the village’s diverse culinary offerings

Cultural and social events make community life dynamic and engaging, appealing to residents who enjoy arts and entertainment close to home.

Outdoor Recreation

For nature and outdoor enthusiasts, Pleasantville provides ample green spaces and recreational opportunities:

• Parks and Trails – Hiking, picnicking, and open fields for sports and relaxation
• Village Green Spaces – Accessible areas for community gatherings, play, and leisure
• Nearby Natural Attractions – Proximity to Westchester County preserves and trails

Outdoor activities complement the village’s cultural and social offerings, supporting a balanced, active lifestyle year-round.

You’ll Fall in Love With

The balance of small-town charm, cultural richness, and excellent schools. Pleasantville is perfect for families and professionals seeking a tight-knit, active, and scenic community with easy access to NYC.

Market Snapshot

• Average Home Price: ~$600K–$1.2M (varies by lot size, style, and proximity to downtown)

• Market Characteristics:

  • Strong demand for homes near the downtown village or top-rated schools
  • Historic homes and tree-lined streets command a premium
  • Limited inventory in sought-after neighborhoods often leads to competitive bidding
  • Buyers prioritize walkability, school access, and community amenities

Buyer Tips

• School district focus: Confirm elementary/middle/high school catchment for properties.
• Walkability: Downtown proximity affects lifestyle and property value.
• Historic homes: Older houses may require modernization or maintenance.
• Parks & recreation: Assess proximity to green spaces for lifestyle fit.
• Community involvement: Local festivals, markets, and events enhance neighborhood experience.
• Commuting: Consider Metro-North station access for NYC travel convenience.

In Summary

Pleasantville combines historic charm, excellent schools, cultural vitality, and abundant green space. Its walkable downtown, vibrant community events, and scenic neighborhoods make it an ideal location for families and professionals seeking a balanced, enriching lifestyle in Westchester County.