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268 South St, 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
35 Schoolhouse Rd, Roxbury
$3,250,000
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
220 Painter Hill Rd, Roxbury
$2,750,000
4 Beds ⋅ 5 Baths ⋅ 24167130 MLS
Perched atop Painter Hill-Roxbury's highest elevation and one of its most coveted addresses-this newly renovated residence offers breathtaking, year-round Sunrise and Sunset views. Spanning over 4,500 sq ft, featuring 4-5 bedrooms and is thoughtfully designed for both comfort and entertaining, complete with a three-story elevator & dedicated game/media room. The chef's kitchen is a showpiece, appointed with premium appliances, a walk-in pantry, oversized island, and stylish bar. It opens seamlessly to a spacious screened porch with inviting dining and lounge areas. Outdoor living is elevated by an expansive ipe deck that functions as a true open-air great room-ideal for al fresco gatherings. The dining room extends to a charming sunset porch adorned with a pergola and irrigated herb garden. The grounds are equally impressive, with professionally designed landscaping that includes an apple orchard, restored stone walls, and a picturesque pond with cascading waterfall. A striking custom pool features a lap lane, lounging platform, and firepit with integrated stone seating, creating a private resort-like setting. Addl highlights include a 3,000-bottle wine cellar, heated garage, pergola-covered carport, and a newly finished oil-and-stone driveway. Ideally located just minutes from the chic shops & fine dining of Washington and Woodbury. Nearby land trust trails offer plentiful hiking. This turnkey property offers easy access to the very best of Litchfield County! Agent Owner.

220 Painter Hill Rd, Roxbury
51 Rocky Mountain Rd, Roxbury
$1,895,000
4 Beds ⋅ 5 Baths ⋅ 24210985 MLS
Charming Country Home with Exceptional Barn-Inspired Great Room Located on a quiet dead end road in central Roxbury, this charming home is enhanced by a spectacular great room addition crafted by master barn builder Ed Cady, creating a warm & distinctive gathering space with extraordinary character. The great room features an enormous walk-in stone fireplace w/ propane starter, soaring ceilings w/ hand-hewn beams, & beautiful wide-board floors. The inviting kitchen opens to a cozy sitting room & addl dining area, creating an easy flow for everyday living & entertaining. Upstairs, the spacious primary suite is a private retreat, complete with vaulted ceilings, a generous walk-in closet, & a beautifully appointed bath. A Juliet walkway overlooks the great room seating area, adding architectural interest & a wonderful sense of connection between the spaces. On the opposite side of the home are 3 additional bedrooms one with ensuite and 2 sharing a hall bath, offering comfortable accommodations for family & guests. The lower level offers abundant potential for a playroom or recreation space, complete w/ a convenient half bath. A 3 car garage provides plenty of parking & storage and connects directly to a practical mudroom w/ sink. With its exceptional craftsmanship, thoughtful floor plan, and inviting blend of rustic character and comfortable living spaces, this is a truly special country home. Walk to the town park w/ playground, baseball, soccer, basketball running traca

51 Rocky Mountain Rd, Roxbury
1030 Washington Woodbury Rd, Roxbury
$1,795,000
4 Beds ⋅ 5 Baths ⋅ 24146457 MLS
NEW PRICE - Privately set on 18.62 acres, this substantial Roxbury country estate offers scale, privacy, and the relaxed elegance that defines Litchfield County living. Designed for both comfortable daily living and effortless entertaining, the home opens to expansive grounds, a pool, and a setting defined by natural beauty and understated presence. With generously proportioned rooms and a strong indoor-outdoor flow, the property offers immediate enjoyment and the flexibility to personalize over time. Now offered at a compelling new price, this is an exceptional opportunity to acquire a significant Roxbury estate with outstanding value in today's market.

1030 Washington Woodbury Rd, Roxbury

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