5 Distinctive New England Estates with Acreage, Waterfront, and Income Potential

Set on 5.68 acres in Putney, this one-of-a-kind Vermont property pairs two dwellings and a yurt studio with a clear connection to the landscape. In the main house, an open layout is finished with handcrafted details, including a kitchen with soapstone countertops and custom cherry cabinetry. A wood-fired masonry heater anchors the living space, while a spacious covered porch overlooks the gardens. Two sun-filled bedrooms and an office round out the plan. Nearby, a beautifully renovated one-bedroom cottage adds flexibility for guests or continued short-term rental use, complete with a deck and outdoor tub. Across the landscaped grounds, the yurt studio offers a quiet, distinctive space with its own outdoor soaking tub. Mature perennial, vegetable, and medicinal plant gardens, plus a 3-stall horse barn, support homesteading or small-scale farming in daily rhythm.

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Down a private drive in Bedford, this residential retreat unfolds as a true private oasis on 6.18 acres. An open floor plan supports easy first-floor living, while a four-season sun room extends the day in every season and opens directly to the deck and hot tub area for effortless indoor-outdoor flow. With four bedrooms, the layout also includes in-law potential in the walkout lower level—ideal for flexible living across generations or for hosting with a bit more separation. Outside, recreation takes center stage with a full-sized tennis court, and the four garages add welcome capacity for vehicles, gear, or weekend projects. The setting invites an unhurried rhythm: morning light in the sun room, afternoons on the court, and evenings easing into the hot tub before turning in.

Along the water’s edge in New Portland, this rare five-property investment portfolio blends residential, commercial, and waterfront income in one diversified holding. Approximately 280 feet of owned waterfront traces Lemon Stream, creating a natural backdrop for daily life and long-term value. Current rents total $9,150 per month, with upside noted to $12,035 per month. The mix includes a Main Street commercial property in Kingfield, multiple residential units—many recently renovated—and the potential for two ground-floor commercial businesses on River Road. Expansion possibilities are built in, with additional buildable lots offering room to grow over time. Set near Farmington and Sugarloaf, the portfolio supports a flexible live/work rhythm today while positioning for meaningful future upside.

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Along the water’s edge in Waldoboro, Waldoberry Farm unfolds with a sense of quiet continuity—each season arriving with its own calm. Spanning almost 8 acres of mixed waterfront and gardens, the land is carefully tended by current stewards who have planted and pruned hundreds of berry trees and bushes. The result is a robust, certified organic berry farm with Aronia, Elderberry, Raspberry, and Cherry harvests, among others, creating a landscape that shifts from bloom to bounty. Beyond the flowering trees, a natural path leads to a scenic Medomak River waterfront point on Dutch Neck, where the setting feels distinctly removed. Completing the experience is a private off-grid cabin, offering a simple retreat at the river’s edge as days slow down and the shoreline becomes part of everyday life.

Set on a private corner lot in one of Tuftonboro’s most peaceful communities, this custom-built modern farmhouse channels a quiet, refined take on New Hampshire’s Lakes Region living. Inside, vaulted ceilings and white oak floors lend a sense of volume and warmth, while quartz surfaces and an expansive gathering kitchen create an easy cadence for everyday meals and unhurried weekends. A floor-to-ceiling stone fireplace anchors the main living space, and a screened porch extends the experience outdoors, keeping you connected to the natural landscape in every season. Just moments away, Lower Beech Pond brings private association beaches and on-the-water days—boating and kayaking in warmer months, with year-round recreation that includes fall foliage and winter skiing. Life here feels both private and beautifully connected.