5 Sold New England Estates from Fairfield to Douglas

Along Fairfield’s Beach neighborhood, arrival is framed by blooming gardens and privacy trees that lend a quiet sense of retreat. Inside, architecturally gorgeous lines and brilliant craftsmanship unfold across 12 rooms and three levels, with an elevator servicing every floor for effortless day-to-day living. Four spacious en-suite bedrooms offer comfort and separation, while thoughtful detailing ties the interiors together: wide-plank hardwood floors underfoot, custom millwork, and built-ins that bring both function and a tailored look. With 9-foot-plus ceilings and elegant finishes throughout, the home balances scale with warmth, creating spaces that feel refined yet easy to live in. From curbside welcome to the top floor, it’s a coastal setting designed for unhurried, beautifully organized living.

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Within the gated community of The Ridge in Fairfield, 212 Fence Row Drive sits on over two private acres, pairing modern comfort with timeless design. A soaring vaulted foyer sets a gracious tone, unfolding into a sun-filled living room framed by a dramatic wall of windows. Entertaining feels effortless here: the formal dining room is finished with tray ceilings and bay windows that keep the atmosphere bright and open. Beyond the front door, everyday life extends into a resort-style setting, with access to a clubhouse, pool, tennis courts, playground, basketball court, and private recreation facilities, all supported by 24/7 gate security. From quiet mornings at home to active afternoons in the community, the experience is equal parts ease and escape.

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Along the edge of Milford’s Great River Estates, this upgraded Colonial pairs a bright, classic layout with views of the Great River Golf Course and partial views of the Housatonic River. A dramatic two-story foyer opens to light-filled rooms finished with hardwood floors, crown molding, fresh paint, and high ceilings. The formal living room and dining room set an easy entertaining flow, while the renovated kitchen brings granite counters, white cabinetry, an oversized sink, a center island, and an eat-in area with sliders to a deck. A family room with a wood-burning fireplace connects to a second deck, and the main level also includes an office, half bath, and laundry room. Upstairs, the expansive primary suite offers its own fireplace, walk-in closet, balcony, remodeled bath, and attached bonus room. A versatile lower level adds space for in-law or au pair living, complemented by an outdoor basketball court and attached two-car garage.

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Set on 1.53 beautifully landscaped acres in Woodbridge’s estate area, this contemporary residence balances privacy with an easy sense of neighborhood charm. A stone wall frames the approach, while a large, open backyard extends the outdoor living—with a new fence installed in 2024 creating a clean, finished edge to the landscape. Inside, the heart of the home is a 2025 remodeled gourmet kitchen designed for everyday rhythm and weekend hosting alike. KraftMaid cabinetry pairs with premium Cambria quartz countertops, and Thermador appliances elevate the experience, including a French door refrigerator and double oven. A dedicated coffee bar, complete with beverage drawers, adds a thoughtful layer of convenience. It’s a setting made for quiet mornings, effortless entertaining, and unhurried time at home.

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Set on nearly three acres in Douglas, this brand-new Colonial channels farmhouse character with modern finishes and careful craftsmanship. White LP Smart Siding sets a crisp exterior tone, while inside, wide-plank white oak flooring runs through more than 2,000 square feet of comfortable living space. The kitchen anchors daily life with quartz countertops, custom hickory cabinetry, stainless steel appliances, floating oak shelves, a wine fridge, and a generous center island designed for easy gatherings. An open-concept layout connects to a bright dining area and inviting family room, complemented by a separate dining room and pantry. Upstairs, the primary suite feels like a retreat, featuring a spa-inspired bath with a soaking tub and walk-in shower. A walkout basement adds flexibility, and country views stretch into a private backyard—peaceful, yet about three miles from Badluck Lake and Whitin Reservoir.

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