5 Distinctive New England Estates and Investments in Four States

Beyond a private gated road, an elegant shingle-style estate unfolds across 20+ secluded acres in Connecticut’s Litchfield Hills, with views that stretch for miles. Designed as a true compound, the property pairs a four-bedroom, five-and-a-half-bath main residence with an in-ground heated Gunite pool, tennis court, greenhouse, a one-bedroom caretaker’s apartment over a 3-bay garage, and a separate two-bedroom guest apartment. Inside, a dramatic two-story foyer highlighted by judges paneling sets a refined tone, while public rooms with extra-tall ceilings, tall windows, and detailed moldings welcome larger evenings. For everyday ease, the sunny great room blends an updated kitchen with dining and a fireside sitting area framed by floor-to-ceiling bookshelves, opening via French doors to a deck. A main-floor primary suite adds a fireplace, brick-terrace access, and a sauna, inviting unhurried mornings and long-view sunsets.

In the heart of Ellsworth’s commercial hub, this well-maintained 17-unit office building pairs strong visibility with everyday accessibility. A consistent rental history underscores its appeal for investors and owner-occupants, while recent capital improvements—including a newer roof and upgraded heating systems—help reduce near-term maintenance concerns. Positioned along one of Downeast Maine’s most active business corridors, the property benefits from Ellsworth’s role as the regional service center for Hancock County, with proximity to Bangor, Bar Harbor, Bucksport, and surrounding coastal communities. Tenants enjoy convenient access to restaurants, professional services, retail, and major routes, supporting a wide range of business uses. The result is a stabilized commercial asset in a high-demand market, shaped for steady performance and long-term growth.

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Set on 260+/- acres in Wilmington, Vermont, historic Wheeler Farm offers a quiet immersion in the state’s rural rhythms. At its center is a 6-bedroom farmhouse that embraces classic farmhouse charm, with the land unfolding as much of the experience as the house itself. Open meadows and green hay fields create long, pastoral sightlines and a sense of space that feels increasingly rare. Come spring, the sugarhouse adds its own signature moment—steam rising on cool days, a small ritual that hints at the property’s working-land heritage and seasonal cadence. With so much acreage under your care, daily life here naturally orbits outdoors, from morning walks across the fields to unhurried afternoons spent taking in the changing light.

Set on 2.7 acres along Wolfeboro’s North Main Street, this 1895 Victorian residence reads as an in-town estate, offering rare privacy within walking distance to the village and Lake Winnipesaukee. Inside, original woodwork and oversized windows preserve the home’s historic character, while five fireplaces add warmth and a sense of occasion. Thoughtful renovations bring contemporary comfort without losing the spirit of the era. The designer kitchen is appointed with Miele, Bosch, and Wolf appliances, custom cabinetry, and a butler’s pantry featuring a copper sink—spaces designed for both everyday rhythm and easy entertaining. With 7 bedrooms and 5 baths, there’s room to host family and guests with ease. Meticulously maintained and lovingly restored, it’s a graceful balance of heritage, artistry, and modern living.

Set on 18 acres along Washington Woodbury Road in Roxbury, this European-style residence pairs privacy and nature with a richly detailed interior and seasonal views. The eat-in kitchen is designed for serious cooking, featuring Sub-Zero refrigeration, a Dacor range, granite countertops, a double farm sink, and a separate pantry. Nearby, a cozy sitting area with fireplace keeps conversation close, while a quiet den offers another fireplace for slower moments. Living and dining unfold in a dramatic, firelit room with French doors opening to an outdoor entertainment area and a Gunite pool. High ceilings and quarter sawn oak floors underscore the home’s sense of ease. Three guest bedrooms sit on the main level, including an en-suite with a marble bath, separate shower and tub, and double vanity. Upstairs, the primary suite features a fireplace, beams, an 18-foot vaulted ceiling, and a balcony.