September - June 2025: $2,000 plus utilities per month. Featured in CTC & G January 2024 Issue! Striking Modern Renovation of Artist's home in private, much sought after location in the rural Litchfield Hills. On a quiet country road, surrounded by woodlands, this 1 bedroom/1 bath apartment, is located beneath the main house and may be rented with the Main House or completely closed off on its own with own laundry room. Ideally situated for hiking and birding in the thousands of acres of Roxbury Land Trust & Steep Rock Preserves. Lake activities and near by the Shepaug River, local farmstands, local fairs, antiquing, cultural venues...

Extra special and super sleek Mid-Century modern in a convenient Roxbury location. Cool mad-men vibe with floor to ceiling windows, exposed beams, vaulted ceilings, stone and wood floors, and wood paneling. Throughout the house the many windows pour natural light in and give fabulous views over the private and manicured grounds. The single-level home has multiple versatile rooms giving a choice of lay-out to fit your needs. The formal living room with fireplace includes the dining space and overlooks the granite patio and Scott inground gunite pool. The updated kitchen with stainless steel appliances boasts a stone floor and charming...

Serenity Now! Total Privacy on 250+ Acres. Accessed Down Long Private Driveway, this 2 Bed, 2.5 Bath Modern Retreat is Set in the Midst of 250+ Acres of Light Woods. Easy Living with a Modern Edge in the 3,100 Square Foot Residence with Open Floor Plan & High Ceilings. Main Level Primary with Full Bath & Woodstove. Large Screened Porch. Separate Barn. Small Pond. 6-Separate Parcels Abutting Land...

Built ca 1788, this petite and cozy antique boasts two original fireplaces on the main level and wide board wood floors on the second level. Loved by the current owner for the past 25 years, the home is charming and comfortable. The living room is flanked by built-in bookcases and has a Vermont Casting wood stove that warms the original section of the home. The eat-in kitchen is nicely sized with a fireplace and beehive oven. The addition includes the family room with oak floors, bath with shower and laundry. Upstairs is the primary bedroom with original floors and two large closets, second bedroom and bath with tub. The barn/garage with...

Set on 14 private and fully fenced acres, this truly spectacular property, once owned by Walter Matthau and his wife Carol Grace, is surrounded by the Matthau Land Trust. The newly built main house was conceived by Geoff Fairbairn, a well-known Litchfield builder, with the current owners adding more features and square footage to the compound, with an eye for detail and enchanting style. The two original cottages have been updated, keeping the historic touches, and are currently used as a guest house and an extensive gym and office area. Among the many things that make this property so special are an attached five-car garage, a pool with spa...

Beautiful Building Lot with Full Approvals in Area of Fine Homes. Premium location midway between Roxbury and Washington centers. Driveway Roughed In leads up toward perfect natural building site set well back from road. Seller had to refocus elsewhere, and leaves additional research results to you, which will facilitate YOUR project! This lot has personality, Antique Stone Wall Feature, Rolling Terrain, Mature Hardwood Trees, Beautiful Ledge Outcroppings and...

Family compound on 30+/- high acres with long driveway to 7-bedroom, 4 1/2 bathroom contemporary main house with easy indoor/outdoor living. Vaulted living/dining with fireplace & sliders to deck. Eat-in Kitchen. First floor primary bedroom suite with fireplace & sliders to deck. Den with fireplace & sliders. Vaulted family room with fireplace. Game room. 3-car attached garage. Separate 2-bedroom, 1-bathroom guest house, swimming pool, tennis court & pond offering total privacy and long western views. Level lawns. 3 parcels. Must...

Mint/Move-in Condition! Meander down the most scenic of Roxbury dirt roads to reach this private colonial with all year heated spa swimming pool on 3.1 +/-acres tucked between the Shepaug River, historic woods, Judd's Bridge and Judd's Bridge Farm and 1000 acres of Steep Rock Land Trust with endless hiking trails. Pristine renovated private country home with 3 bedrooms/2.5 baths and an ample home office. Open floorplan Living/Eat-in Kitchen/Family Room with wood burning fireplace and sliders to a year-round 8'x 16' spa pool and patio. Dine or relax on the granite terrace or covered front porch surrounded by mature woods and amazing rock...

Pristine St. Barth-Style bungalow with two-car garage. Single-level living surrounded by Roxbury's best historic estate neighborhood, farms and homes of artists, actors and writers. Magnificent open floor plan with 2-3 bedrooms, 2 fireplaces, new eat-in kitchen, vaulted living room, den and screened porch. Dine or relax on the flagstone terrace next to the heated gunite pool. Mature gardens with climbing roses, lavender and blue...

Utterly Private Country Estate. Expansive 4+ bedroom meticulously maintained, classically-designed house set high up a long tree-lined driveway w/distant southern & western/sunset views on 24+ secluded acres of verdant lawn, beautiful perennial gardens, ancient trees and a serene pond. Grand room dimensions, high ceilings, solid wide-board pine floors & windows designed to maximize the stunning views throughout. Formal center hall. Elegant living room w/wood-burning fireplace. Stately dining room. Fabulous great room/kitchen w/vaulted ceiling, large stone fireplace, over-sized windows & access to a mahogany deck & lovely...

Roxbury Hill. Pack your bags & move right into this splendid home on 4.43 acres w/ 3 bedrooms & 2 full baths in immaculate condition. A winding new asphalt driveway leads by the pond to the fairy tale house w/ attached 2-car garage. Enter through a sun-filled room currently used as an office & make your way through French doors to the living room w/ gas fireplace. The formal dining room also has French doors to the back deck. The chef's kitchen w/ high-end appliances (Viking, Miele, Subzero & Jenn Air) has the perfect sized center island, granite countertops and loads of storage making this a dream kitchen for friends &...

Pristine and private Modern Farmhouse with magnificent design, vaulted ceilings, 2 fireplaces, over-sized living room, dining room for 10, chef's kitchen, 3 bedrooms. Beautifully sited heated pool surrounded by endless summer hydrangea and 8 +/- acres of lawns, pond, and fields. Ideal for walking, jogging and biking. Perfect location, minutes from the centers of Roxbury and...