A rare opportunity to acquire 102 private acres in Alton with two architect-designed residences, separate driveways and exceptional privacy between them. Together, 435 and 437 Avery Hill Road offer approximately 8,000 finished sq. ft., 7 bedrooms and 7 full baths, with a striking combination of contemporary architecture, craftsmanship and flexible living space. Approached through mature woodland, the property opens to field, forest and southwest mountain views, with memorable sunsets and approximately 1,700 feet of road frontage. The setting is private and rural, yet convenient to Alton and the Lakes Region. The two homes are distinctly different. One offers late-mid-century architectural character with an in-ground pool, barn and outbuildings; the other features substantial timber framing, dramatic interior volume, custom woodwork, a third-floor studio and extensive workshop space. Together they create unusual flexibility for a family compound, multi-generational living, guest residence, creative retreat or legacy holding. The scale of the offering also creates possibilities beyond simply occupying both homes. A buyer might choose to live in one residence while retaining, repurposing or separately planning the other portion of the property for future land-use or subdivision potential, subject to buyer due diligence, municipal approvals, zoning and all applicable requirements. Offered together at $2,650,000, giving a buyer the opportunity to control the entire 102-acre Avery Hill holding. The properties are also offered separately as 435 Avery Hill Road, MLS 5100206, and 437 Avery Hill Road, MLS 5103112.