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$3,995,000
5 Beds ⋅ 6 Baths ⋅ 24177581 MLS
A breathtaking country estate nestled in the picturesque town of Roxbury, Connecticut, boasts a guest cottage and an in-ground Gunite pool. Encompassing 8.03 acres, the property is surrounded by Jack's Brook and a land trust on two sides, providing a serene and secluded environment. The primary residence, meticulously updated, features exquisitely proportioned rooms. It comprises five bedrooms and five full bathrooms and one powder room. A grand living room, complete with a two-story fireplace and windows on three sides, opens to two decks overlooking the rear yard. The spacious formal dining room, equipped with a gas fireplace and soft indirect lighting, is ideal for hosting formal gatherings. The chef's-eat-in kitchen, generously furnished with ample cabinetry, marble countertops, connects to a large deck and a granite patio, facilitating seamless outdoor dining. The primary level's main suite features French doors to the gardens, a luxurious bath, two walk-in closets, and a private sitting room. Three additional ensuite bedrooms complete the main level. The lower level offers a media room, a game room, a bunk room with built-in beds, a spa bath, and a laundry facility. A separate guest cottage provides a cozy retreat with two bedrooms, two bathrooms, a vaulted great room, a kitchenette, a fireplace, and a wrap-around deck. A must see!

47 Squire Rd, Roxbury
$3,950,000
4 Beds ⋅ 7 Baths ⋅ 24192621 MLS
Uber chic shingle-style in A+ location offering magnificent long distant views overlooking the famed Alexander Calder estate. Formal parking courtyard leads to the gracious double height entrance foyer. Mesmerizing views from almost every room. Grand Living Room with high coffered ceilings, gas fireplace, wood paneling & French door to balconies. Library with built-in bookcases. Powder room. First floor primary bedroom suite with Waterworks bathroom, soaking tub, two walk-in closets, balcony & home Office. Intimate Dining Room with large picture window. Eat-in country Kitchen with beamed ceiling and large picture window. Family Room with fireplace & wet bar. Screened porch with bluestone floor & electric stove. Laundry Room. 3 guest bedrooms en suite on the 2nd floor. Recreation Room over the 3-car attached garage. Walk-out lower level includes a gym, wine cellar, full bath & second laundry. Gracious long driveway affording total privacy amidst park-like grounds with beautiful perennial gardens, swimming pool, fire pit, mature plantings & forever views. Hardwood floors & high ceilings throughout. Lutron lighting. Central AC. Backup generator.

297 Painter Hill Rd, Roxbury
$3,600,000
5 Beds ⋅ 5 Baths ⋅ 24183686 MLS
Quintessential Litchfield County Estate on 41+/- acres. Restored 1850's Colonial. Set in private, park-like grounds, overlooking spring-fed pond & meadows w/ views and mature trees. 5-bedrooms, 4.5 bathrooms, eat-in kitchen w/ fp, great room w/ fp and dining room with French doors, family room w/ fp, sunroom with wet bar, library, office, media room, recreational room, porch, 3-car garage, gunite pool, pool house, 4-stall horse barn, tennis court. Riding ring, fenced pastures, wooded trails for hiking etc. Perennial gardens. Property abuts conservation land. Complete privacy. Rare opportunity. Property has only been on the market twice before in past 100 years.

268 South St, Roxbury
$3,495,000
4 Beds ⋅ 5 Baths ⋅ 24201025 MLS
Subtle Sophistication in A++ Roxbury Locale. Perfectly sited in an estate area of Roxbury on a quiet country road, this renovated country cottage exudes understated elegance & modern comfort. Main house offers one-level living & turn-key perfection, w/chic kitchen featuring custom cabinetry, stainless steel appliances, it flows seamlessly into the dining room. Dramatic great room w/floor-to-ceiling glass & fireplace anchors the living spaces, opening directly to large deck for effortless outdoor entertaining & picturesque views of the grounds. There are 4 ensuite bdrms, incl a stunning 1st-flr primary suite w/sitting room, gas fireplace, 2 fully built-out walk-in closets, & French doors leading to a private terrace with outdoor fireplace. Cozy library/den with built-ins and a versatile lower-level bonus space are ideal for an art studio or private home office. Add'l highlights incl a steam shower, smart-home features, radiant heat w/hydro-air backup, 2 washers & dryers. Dramatic post-and-beam guest house w/ vaulted ceiling, balcony, & full kitchen sits above a 2 car garage and prep kitchen, offering a private retreat complete w/its own washer/dryer. The grounds are exceptional-mature trees, stone walls, a pond, sweeping lawns, and lush gardens surrounding a heated gunite pool. Expansive porches and terraces provide seamless indoor-outdoor living, ensuring total privacy. Minutes from The Mayflower Inn, town center and close to acres of Roxbury Land Trust. 90 min to NYC.

35 Schoolhouse Rd, Roxbury
$3,200,000
3 Beds ⋅ 2 Baths ⋅ 24186522 MLS
Exceptional equestrian estate featuring a fully equipped horse facility and charming Cape-style home. Ideal for equestrians, trainers, or boarding professionals, the property offers 16 rubber-matted stalls, a large well-lit indoor arena, and a second-floor viewing lounge with kitchen amenities-perfect for lessons, clinics, and entertaining. The barn includes a wash stall, feed room, hay storage, boarder tack lockers, laundry area, and full bath. Safety is enhanced by a commercial sprinkler system. Owned pole-mounted solar panels are installed but are not currently operational. Outside, expansive grass paddocks and a large sand/stone dust outdoor arena provide ample space for training and turnout. Bordering Land Trust property with a river and miles of trails, you can horseback ride or hike directly from your back door. "The Shepaug is one of those rivers that looks like it was painted by someone who had too much talent and not enough canvas." written by Charles Hayes. The Cape-style home features 3 bedrooms and 2 full baths, blending classic New England character with modern comfort. A 2-car attached garage is complemented by a detached 4-car garage, plus an additional detached 3-car garage with a second-floor apartment-ideal for guests, staff, rental income, or a home office.

124 Botsford Hill Rd, Roxbury

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