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$520,000
3 Beds 3 Baths COMING SOON Status 24203910 MLS
The tax record may say 1935, but this is far from your typical 1935 home. The original footprint represents just a small portion of the home you see today, thoughtfully renovated and expanded over the decades by its builder-owner to create a home designed for the way we live now. The spacious kitchen features a center island, abundant cabinetry, pantry and breakfast area, flowing easily into the dining room and inviting living spaces. A true standout is the impressive family room addition with vaulted ceiling, walls of windows, its own front entrance and access to the deck, creating flexible space for entertaining, relaxing, a game room, studio or whatever fits your lifestyle. The main level offers two bedrooms and an updated full bath, while upstairs, the private primary suite features a walk-in closet and spa-like bath with freestanding soaking tub and beautifully tiled glass shower. A dedicated lower-level office provides quiet work-from-home space. Outside, enjoy multiple areas to gather and unwind, including a paver patio and a fenced-in retreat with above-ground pool, spacious deck and pool clubhouse. Located in Rockfall, you're close to Lake Beseck, Powder Ridge, Lyman Orchards and Wadsworth Falls, with convenient access to shopping and highways. 1935 may be where the story started, but this home has evolved beautifully for today's lifestyle.

12 Ross Rd, Middlefield

$749,000
4 Beds 3 Baths ACTIVE Status 24196454 MLS
Older than America, the historic Chilson Bailey House offers a rare opportunity to own a true circa 1750 center-chimney Colonial while enjoying the comfort of a thoughtfully designed 2008 addition. Offering four bedrooms in total, two bedrooms are located within the original 1750 portion of the home, which is not currently livable and requires renovation. This gives the next owner the opportunity to restore an authentic piece of Connecticut history at their own pace while enjoying comfortable living from day one. Everyday living takes place in the 2,963-square-foot addition, featuring a spacious country kitchen with an oversized island, a soaring great room with a floor-to-ceiling stone fireplace, wide-plank pine floors, a first-floor primary suite, and an expansive second-floor loft ideal for a home office, family room, or creative space. Outside, an impressive barn and detached garage offer exceptional space for car collectors, hobbyists, contractors, woodworking enthusiasts, or anyone needing room for projects, equipment, or recreational vehicles. Significant improvements have already been completed, including the addition, detached garage, septic system, 200-amp electrical service, leased solar, and new windows in the original home. For the buyer who sees possibility where others see a project, this is a chance to live comfortably today while bringing the historic heart of an extraordinary Connecticut property back to life.

19 High St, Middlefield

$749,900
4 Beds 3 Baths ACTIVE Status 24190498 MLS
Nestled in the heart of scenic Middlefield, this distinctive and beautifully maintained 4 bedroom 2.5 bathroom property offers a rare blend of classic New England character and modern flexibility. Inside on the first floor, an open-concept kitchen and dining area invite gathering and entertaining, seamlessly flowing into a sunroom-style flex space with room to grow-ideal for a home office, playroom, or reading nook. A separate living room, complete with a working fireplace, creates a cozy retreat for New England winters or days on the slopes of the nearby Powder Ridge Ski Resort. For the summer, step outside and you will find a stunning in-ground pool surrounded by a spacious brick patio, perfect for lounging and outdoor dining. An attached two-car garage adds everyday convenience and a second private driveway offers access to the rear of the property and the detached barn. The true gem is this fully renovated, detached barn-an inspired space with limitless potential. Featuring whitewashed wood walls and an airy farmhouse aesthetic, the barn offers a dramatic open-plan ground level and a second floor with three rooms and a bathroom. Off of the ground level, french doors lead to a private terrace shaded by mature grapevines, ideal for al fresco dining or sunset cocktails. Whether used as a luxurious art studio, at-home gym or work-from-home suite, this space delivers unmatched versatility with its own entrance and a beautiful walkway connection to the main home and pool.

88 Powder Hill Rd, Middlefield

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