Nestled behind a private gated entry on 9.31 secluded acres, this extraordinary Connecticut River Valley estate is a rare luxury compound of architectural distinction, privacy, and resort-caliber amenities. Thoughtfully composed across five architecturally distinct structures, the property blends modern luxury, European influences, and timeless craftsmanship amid curated landscapes, stone pathways, terraces, and over 6,000 square feet of refined outdoor living space. This is a truly exceptional, once-in-a-lifetime offering.

A long private drive winds past stone walls and mature trees, gradually revealing an exclusive enclave where the outside world fades away. Stucco facades, cedar shake roofs, and copper gutters emerge in sequence, unified by professionally landscaped grounds, comprehensive irrigation, and subtle exterior lighting that enhances the estate’s serene atmosphere.

Completely rebuilt in 2012, and finished in 2015, the main residence is a masterclass in craftsmanship and livability. Rich millwork, custom cabinetry, radiant-heated hardwood floors, transom windows, and skylights define interiors that feel both elegant and inviting. A boutique-style coatroom and a jewel-box powder room finished in onyx mosaic, mother-of-pearl, and hammered copper immediately signal the home’s uncompromising level of finish.

Designed as both a culinary workspace and gathering place, the kitchen features high-gloss bespoke cabinetry, nickel hardware, and a sculptural custom range hood beneath tall ceilings accented with silver-leaf detailing. A substantial Calacatta marble island integrates a second sink, butcher block station, and concealed storage. Chef-grade appliances include SubZero, Wolf, and Miele. French doors open to a stone patio with built-in grill and views of the spring-fed pond, creating seamless indoor-outdoor living.

The living room is defined by a graceful barreled ceiling, stunning fireplace, and bay window with arched transom framing tranquil water views. A luminous sunroom with vaulted ceilings, skylights, and a built-in orchid garden offers a serene retreat immersed in landscape. The sunken dining room makes a dramatic statement with travertine floors, a coffered ceiling with gold detailing, and floor-to-ceiling windows opening to the grounds. A club-inspired bar and cocktail lounge features a cathedral ceiling with gold-foil finish, crystal chandeliers, gorgeous wet bar, and richly textured finishes—an unforgettable space for entertaining. The library is a refined private study with floor-to-ceiling built-ins, gas fireplace, granite accents, and a staircase lined with bookshelves and a window seat—an elegant blend of intellect and comfort.

The primary suite is a personal sanctuary with French doors opening to a stone terrace, lovely built-ins, automated shades, and dual walk-in closets with tailored storage and a built-in safe. Two opulent marble bathrooms include a whirlpool tub, Carrara marble shower, onyx and glass tile finishes, towel warmer, and hand-tailored vanities.

An upper loft overlooks the cocktail lounge and opens to a covered balcony, featuring vaulted gold-leaf ceilings and a hidden cedar-lined storage room. A media room above offers a cinematic retreat with paneled walls, wet bar, and access to an outdoor balcony. Upper level interiors continue on to a second bedroom suite featuring vaulted wood-paneled ceilings, skylights, built-in desk and cabinets, a cedar walk-in closet, and a refined en-suite bath, ideal for weekend visits or extended stays.

Beyond the main residence, the estate unfolds as a peaceful resort. Fully renovated, the Billiards House serves as a guest residence and entertainment pavilion with vaulted ceilings, pool table room, gas fireplace, kitchen and wet bar, private bedroom suite, den, two-car garage, mudroom/potting room, and pergola-covered flagstone patio.

On the upper tier, The Pool House offers an open studio layout with vaulted ceilings with dramatic beams, stone fireplace, well-equipped kitchen, spa-like bath, and direct access to the pool terraces. Below, a climate-controlled wine cellar features separate red wine and white wine/champagne rooms, wood-paneled walls, tasting areas, exposed rock ledge, and a dramatic spiral staircase - a hidden sanctuary for collectors and connoisseurs. 

Outdoor living is equally compelling, anchored by an in-ground heated pool and spa with waterfalls, expansive flagstone patios, fire features, a fully equipped outdoor kitchen with Viking grill and pizza oven, and a bocce court, all framed by meticulously designed landscaping.

A glass greenhouse, with radiant heated floors and vaulted ceilings, provides year-round cultivation, complemented by an adjacent potting cottage with copper sinks, built-ins, and charming architectural details.

With its own gated entrance, the Upper House, rebuilt in 2005, offers approximately 1,600 square feet of flexible living space, radiant-heated floors, open living areas, loft bedroom, and a four-car garage. Elevated and private, it presents opportunities for guests, extended family, or future potential.

Rarely does an offering of this caliber become available. More than a residence, 252 River Road is a fully realized lifestyle property designed for those for value privacy, craftsmanship, and refined living.