68 Hilltop Drive, Windham

Welcome to The Hill, a private enclave of high-end homes tucked away in the scenic hamlet of Maplecrest, just minutes from Windham Mountain Club and CD Lane Park. Perched on 6 peaceful acres at the end of a quiet cul-de-sac, this 3,500+ sq ft custom contemporary blends crisp architectural design with warm rustic touches for the ultimate Catskills retreat.

Built by renowned Hitchcock Builders, this home is a testament to quality and craftsmanship. The current owner has lovingly maintained the property, acting as a true steward of the home—ensuring it has been thoughtfully updated over time. Recent upgrades include a brand-new roof, freshly painted exterior, central air conditioning, water filtration, and security systems for peace of mind.

One of the home's showstoppers is the expansive 1,500 sq ft Trex deck, perfect for outdoor dining, relaxing, and entertaining—complete with stunning views, lush lawns, and visits from local wildlife.

Inside, the main level features a vaulted great room with a dramatic bluestone fireplace and a wall of glass that brings in natural light and sweeping mountain views. The spacious eat-in kitchen includes granite counters, a center island, and an adjacent dining area—an ideal spot to sip morning coffee while soaking in the views. Off the kitchen, a cozy den with rustic pine walls and a pocket door provides a quiet space for reading, crafting, or game nights.

The main-floor primary suite offers views of the surrounding peaks and a renovated bathroom with a walk-in shower. A welcoming foyer and powder room add practicality and flow.

Upstairs, a guest wing with full bath offers privacy for overnight visitors. The lower level is made for recreation and relaxation, featuring a second living room with woodstove, game area, glass doors leading to a patio, outdoor hot tub, and firepit. Two additional ensuite bedrooms—each with their own renovated bathrooms—make hosting everyone effortless.

A spotless two-car garage includes cubbies for skis, bikes, and outdoor gear, plus a utility sink and mechanical room with a brand-new, high-efficiency heating system.

Impeccably landscaped and perfectly positioned in the highly desirable Maplecrest Valley, 68 Hilltop Drive offers rare privacy and panoramic views—all in a location that rarely becomes available. Move-in ready and being sold fully furnished, this cherished mountain home is a turn-key treasure.

Properties for Sale Similar to 68 Hilltop Drive, Windham, NY

New Listing

205 Nauvoo Road Road, Windham

$827,000 - 4 Beds, 2 Baths, 2,200 Sf

MLS® # 20253309

5320 Route 23, Windham

$850,000 - 8 Beds, 8 Baths, 3,712 Sf

MLS® # 20252750

490 Mill Street, Windham

$1,200,000 - 4 Beds, 4 Baths, 2,928 Sf

MLS® # 20252409